Brewster Vacation Rentals

176 properties
Brewster Guide

Brewster vacation rentals that sleep 15

Brewster Summer Cottage
Brewster
ID 18622
  • 5 BR
  • 3 baths
  • Sleeps 15

Brewster Summer Cottage

Distance to beach: 0.1 miles, 2 minute walk
5.04 reviews

Summer:

$5,250 - $6,750/wk

$20,000/mo

Off Season:

$200 - $600/night

$2,250 - $6,250/wk

$3,000 - $20,000/mo

2
Rented! 4 Boats-Isolated 3 Acre Waterfront Private Beach
Brewster
ID 17772
  • 5 BR
  • 3 baths
  • Sleeps 15

Rented! 4 Boats-Isolated 3 Acre Waterfront Private Beach

Distance to beach: Directly on two ponds: Canoe Pond and Upper Mill Pond and bay beach is 3 miles away on Linnell Landing
5.027 reviews

Summer:

$13,450/wk

Off Season:

$8,850 - $110,450/wk

3

Brewster vacation rentals that sleep 14

Waterfront with private beach, perfect for family vacation
Brewster
ID 34024
  • 6 BR
  • 4 baths
  • Sleeps 14

Waterfront with private beach, perfect for family vacation

Distance to beach: Sandy beach on property Sheep Pond and Private beach directly on Sheep Pond
5.09 reviews

Summer:

$10,000 - $11,500/wk

Off Season:

$775 - $1,525/night

$5,000 - $11,500/wk

$10,000 - $15,000/mo

5
Bayview Home: Walk to Association Pond and CCRT!
Brewster
ID 39089
  • 6 BR
  • 3 baths
  • Sleeps 14

Bayview Home: Walk to Association Pond and CCRT!

Distance to beach: Walk to Assoc. Pond, 1.7 mi to Linnell Landing
5.06 reviews

Off Season:

$600 - $700/night

$5,125 - $5,625/wk

3

Brewster vacation rentals that sleep 12

Beautiful Family Compound located in the Heart of Brewster
Brewster
ID 23093
  • 5 BR
  • 3 baths
  • Sleeps 12

Beautiful Family Compound located in the Heart of Brewster

Distance to beach: 5/10 of a mile to Bay beach. Point of Rocks Beach
4.622 reviews

Summer:

$3,700 - $4,000/wk

Off Season:

$1,000 - $3,600/wk

2
Spacious Brewster Cape Cod | Heated Pool, AC, Family Fun!
Brewster
ID 36424
  • 5 BR
  • 3 baths
  • Sleeps 12

Spacious Brewster Cape Cod | Heated Pool, AC, Family Fun!

Distance to beach: 2.7 mi to Paine's Creek
5.022 reviews

Summer:

$7,850 - $10,300/wk

Off Season:

$625 - $929/night

$4,000 - $6,500/wk

$12,000 - $20,000/mo

4
Stunning Views and Water Access; Kayaks & SUP
Brewster
ID 40977
  • 5 BR
  • 2 baths
  • Sleeps 12

Stunning Views and Water Access; Kayaks & SUP

Distance to beach: 500ft to Association Beach;3mi to Breakwater Beach

Summer:

$5,125/wk

Off Season:

$249 - $549/night

$2,325 - $5,125/wk

2
Renovated Brewster Beach House + Cottage Near Bay Beaches
Brewster
ID 33519
  • 4 BR
  • 3 baths
  • Sleeps 12

Renovated Brewster Beach House + Cottage Near Bay Beaches

Distance to beach: 8/10 mi to Point of Rocks Beach
5.010 reviews

Summer:

$7,150 - $7,350/wk

Off Season:

$250 - $750/night

$5,350 - $6,950/wk

$3,000 - $12,000/mo

7

Brewster vacation rentals that sleep 11

Brewster vacation rentals that sleep 10

Private 5 BR mini-estate for your family's dream vacation
Brewster
ID 9406
  • 5 BR
  • 2 baths
  • Sleeps 10

Private 5 BR mini-estate for your family's dream vacation

Distance to beach: 1.4 miles to Crosby Landing
4.917 reviews

Summer:

$5,000 - $8,300/wk

Off Season:

$600/night

$3,500 - $5,000/wk

5
Upper Mill Pond Waterfront Compound Pet Friendly 2 Units
Upper Mill Pond
ID 41616
  • 5 BR
  • 5 baths
  • Sleeps 10

Upper Mill Pond Waterfront Compound Pet Friendly 2 Units

Distance to beach: On Private Beach
1 review

Summer:

$12,535 - $14,535/wk

Off Season:

$750 - $1,000/night

$7,535 - $12,535/wk

4
Charming Home on Lower Mill Pond in West Brewster
Brewster
ID 15471
  • 4 BR
  • 3 baths
  • Sleeps 10

Charming Home on Lower Mill Pond in West Brewster

Distance to beach: 2 miles to Brewster bayside beaches
5.021 reviews

Summer:

$4,250 - $4,450/wk

Off Season:

$200 - $300/night

$3,350 - $4,050/wk

6
 1/10 of a mile to Saints Landing Beach!
Brewster
ID 19037
  • 4 BR
  • 2 baths
  • Sleeps 10

1/10 of a mile to Saints Landing Beach!

Distance to beach: 2 1/2 minute (pretty) walk from house to beach
4.52 reviews

Summer:

$3,940 - $5,040/wk

Off Season:

$371 - $571/night

$3,445 - $5,040/wk

Antique Cape Cod Charm in Brewster <1 mile to beach
Brewster
ID 34925
  • 4 BR
  • 3 baths
  • Sleeps 10

Antique Cape Cod Charm in Brewster <1 mile to beach

Distance to beach: 8/10 mi to Saints Landing and 1 mile Paine's Creek
5.05 reviews

Summer:

$5,550/wk

Off Season:

$3,800 - $4,800/wk

2
Large Family Home w/ Spacious Yard - Walk to Nickerson Park
Brewster
ID 39859
  • 4 BR
  • 3 baths
  • Sleeps 10

Large Family Home w/ Spacious Yard - Walk to Nickerson Park

Distance to beach: 1.2 Cliff Pond and 2.8 to Linnell Landing Beach
5.06 reviews

Summer:

$4,400 - $4,900/wk

Off Season:

$315 - $650/night

$2,800 - $4,000/wk

3
Hydrangea House with Vegetable Garden Near Seymour Pond
Brewster, The Highlands
ID 8727
  • 4 BR
  • 3 baths
  • Sleeps 10

Hydrangea House with Vegetable Garden Near Seymour Pond

Distance to beach: 2 miles Breakwater Beach and 1/2 mile to Seymour Pond
4.920 reviews

Off Season:

$3,800/wk

8
Linnell Landing, 2 Master Suites & Steps to Private Beach
Brewster
ID 23594
  • 4 BR
  • 4 baths
  • Sleeps 10

Linnell Landing, 2 Master Suites & Steps to Private Beach

Distance to beach: 1/10 mile to a private community Bay beach
5.07 reviews

Off Season:

$715 - $1,125/night

$4,000 - $5,000/wk

4
Gorgeous 4 Bedroom, 3.5 Bath Home w/AC in Brewster
Brewster
ID 33835
  • 4 BR
  • 3 baths
  • Sleeps 10

Gorgeous 4 Bedroom, 3.5 Bath Home w/AC in Brewster

Distance to beach: 4 miles to Paine's Creek
5.04 reviews

Summer:

$4,950/wk

Off Season:

$1,950 - $4,450/wk

$4,000 - $10,000/mo

2
Family Retreat w/ Direct Nickerson State Park Access
Brewster
ID 41109
  • 4 BR
  • 2 baths
  • Sleeps 10

Family Retreat w/ Direct Nickerson State Park Access

Distance to beach: 2 mi to Crosby Landing and .8 mi to Cliff Pond
7 reviews
OWNER SPECIAL:

Fall Weekends in Brewster — 2 Nights $595 / 3 Nights $795 — Pet-Friendly 4BR in the Woods.

Summer:

$4,050/wk

Off Season:

$325 - $550/night

$2,950 - $4,050/wk

$3,400/mo

4
Luxury near Paine's Creek Beach
Brewster
ID 22720
  • 3 BR
  • 3 baths
  • Sleeps 10

Luxury near Paine's Creek Beach

Distance to beach: 1/2 mile to Paine's Creek Beach.
5.010 reviews

Summer:

$4,125/wk

Off Season:

$500/night

$3,700 - $4,125/wk

$10,000/mo

4
Charming Cottage and Glamping Bunkhouse Steps From The Beach
Brewster
ID 31348
  • 3 BR
  • 1 bath
  • Sleeps 10

Charming Cottage and Glamping Bunkhouse Steps From The Beach

Distance to beach: 2/10 mile Paine's Creek and Easy walk to Mant's Landing from Paine's Creek
4.918 reviews
OWNER SPECIAL:

Fall Rental Rate Discount-Stunning Sunsets a Short Stroll Away.

Summer:

$3,530 - $3,630/wk

$2,000 - $2,800/mo

Off Season:

$250 - $300/night

$930 - $1,430/wk

$2,000 - $2,800/mo

5
Waterfront 3 Bedroom  with A/C - WIFI on Upper Mill Pond
Brewster
ID 34366
  • 3 BR
  • 3 baths
  • Sleeps 10

Waterfront 3 Bedroom with A/C - WIFI on Upper Mill Pond

Distance to beach: Directly on Upper Mill Pond Upper Mill Pond
5.025 reviews

Summer:

$5,000 - $5,700/wk

Off Season:

$4,000 - $4,500/wk

6

Brewster vacation rentals that sleep 9

The Mink Shell - 5 Min Walk to TWO Bay Beaches!!
Brewster
ID 5843
  • 3 BR
  • 2 baths
  • Sleeps 9

The Mink Shell - 5 Min Walk to TWO Bay Beaches!!

Distance to beach: +/- 400 yards Saints Landing and 2/10 of a mile to Saints Landing & Manse Beaches
4.113 reviews
OWNER SPECIAL:

$1500 - $2500 per Month Rental plus utilities from October - June 2027!

Summer:

$3,200 - $3,400/wk

$12,500/mo

Off Season:

$400 - $800/night

$1,500 - $2,900/wk

$1,500 - $12,500/mo

3
Renovated Coastal Farmhouse at Greenland Pond
At Greenland Pond
ID 35643
  • 3 BR
  • 2 baths
  • Sleeps 9

Renovated Coastal Farmhouse at Greenland Pond

Distance to beach: Greenland Pond - 2/10 of mile
5.06 reviews

Summer:

$5,105 - $5,505/wk

Off Season:

$225 - $800/night

$4,305 - $4,905/wk

$3,800 - $8,000/mo

5
Close to 4 bay beaches, plus loads of space and privacy
Brewster
ID 36297
  • 3 BR
  • 2 baths
  • Sleeps 9

Close to 4 bay beaches, plus loads of space and privacy

Distance to beach: 0.7 mi to Saints Landing and 1 mi to Robbin's Hill Beach
5.07 reviews

Summer:

$3,900 - $4,100/wk

Off Season:

$335 - $395/night

2
PET FRIENDLY! NewlyRenovated~Private Sheep Pond Beach Access
Sheep Pond Estates, Brewster
ID 37957
  • 3 BR
  • 3 baths
  • Sleeps 9

PET FRIENDLY! NewlyRenovated~Private Sheep Pond Beach Access

Distance to beach: 1/2 mile to Sheep Pond and 2 miles Crosby Landing
5.014 reviews
OWNER SPECIAL:

Booking for 2027 . Dogs allowed.Quiet cut de sac in Sheep Pond Estates. Private beach , Hidden gem!

Summer:

$3,496 - $3,796/wk

Off Season:

$295/night

$1,001 - $3,296/wk

$8,000/mo

Quiet Cape Retreat with AC; Walk to Rail Trail and Nickerson
Brewster
ID 38124
  • 3 BR
  • 2 baths
  • Sleeps 9

Quiet Cape Retreat with AC; Walk to Rail Trail and Nickerson

Distance to beach: 1.3 mi to Linnell Landing and 1.8 mi to Crosby Landing
5.014 reviews

Summer:

$3,275/wk

Off Season:

$1,940/wk

6
Slate & Salt | Renovated Cape · Beach & Kids Ready
Brewster
ID 41803
  • 3 BR
  • 2 baths
  • Sleeps 9

Slate & Salt | Renovated Cape · Beach & Kids Ready

Distance to beach: 0.8 miles to Point of Rocks Beach and 1.3 miles to Breakwater Beach

Summer:

$5,799/wk

Off Season:

$399 - $849/night

$3,299/wk

2

Brewster vacation rentals that sleep 8

200 Steps to our Private Beach. Lots of room & Central AC!
Sea Pines
ID 27199
  • 4 BR
  • 4 baths
  • Sleeps 8

200 Steps to our Private Beach. Lots of room & Central AC!

Distance to beach: 1/10 mile to private association Sea Pines Beach
5.024 reviews

Summer:

$4,500 - $5,500/wk

Off Season:

$3,300 - $3,600/wk

$10,700 - $11,000/mo

2
Lovely 4 BR Cottage - Near Nickerson Park and Bay Beaches
Brewster
ID 32760
  • 4 BR
  • 2 baths
  • Sleeps 8

Lovely 4 BR Cottage - Near Nickerson Park and Bay Beaches

Distance to beach: 1.7 miles to Crosby Landing and 4.9 Nauset Beach
5.03 reviews

Summer:

$2,325 - $2,725/wk

Off Season:

$1,425 - $2,225/wk

3
Access to Upper Mill Pond-Kayaks, Canoe, SUP's Included
Brewster
ID 37988
  • 4 BR
  • 2 baths
  • Sleeps 8

Access to Upper Mill Pond-Kayaks, Canoe, SUP's Included

Distance to beach: 600ft to Upper Mill Pond; 1mi Paine's Creek Beach
5.02 reviews

Summer:

$3,200 - $3,500/wk

Off Season:

$350 - $400/night

$2,000 - $3,500/wk

2
Short Walk to Beach w/ Fire Pit & Outdoor Shower
Brewster
ID 35390
  • 4 BR
  • 1 bath
  • Sleeps 8

Short Walk to Beach w/ Fire Pit & Outdoor Shower

Distance to beach: 0.6 mi to Point of Rocks Beach and 0.1 miles to Sea Pines Association Beach

Summer:

$357 - $471/night

$2,843 - $3,687/wk

Off Season:

$214 - $357/night

$1,788 - $2,843/wk

2
Modern Home - Private Lake Access - Rail Trail
Brewster
ID 38589
  • 4 BR
  • 2 baths
  • Sleeps 8

Modern Home - Private Lake Access - Rail Trail

Distance to beach: 1 block to Seymour Pond
5.02 reviews

Summer:

$3,460 - $4,230/wk

Off Season:

$300 - $425/night

$2,760 - $3,215/wk

5
Bayfront Beach Cottage
Brewster
ID 16812
  • 4 BR
  • 1 bath
  • Sleeps 8

Bayfront Beach Cottage

Distance to beach: Private beach on the Bay (the Brewster Flats).
1 review

Off Season:

$3,385/wk

4
Family Friendly Home at Cobbs Pond/Cape Cod Bay in Brewster
Brewster
ID 19423
  • 4 BR
  • 3 baths
  • Sleeps 8

Family Friendly Home at Cobbs Pond/Cape Cod Bay in Brewster

Distance to beach: 100 yards Breakwater Beach and 15ft to freshwater swimming and 1/10 mile to beach
4.915 reviews

Off Season:

$300/night

$2,200 - $4,200/wk

5
Charming 4 Bedroom Home near Breakwater Beach
Brewster
ID 23161
  • 4 BR
  • 2 baths
  • Sleeps 8

Charming 4 Bedroom Home near Breakwater Beach

Distance to beach: Less than 1 mile to Breakwater Beach

Summer:

$3,120 - $3,320/wk

$11,000 - $12,000/mo

Off Season:

$1,820 - $3,020/wk

$4,000 - $10,000/mo

Updated, Comfortable and Family Friendly with Full AC
Brewster
ID 31031
  • 4 BR
  • 2 baths
  • Sleeps 8

Updated, Comfortable and Family Friendly with Full AC

Distance to beach: 3.6 miles to Linnell Landing
5.03 reviews

Off Season:

$350 - $600/night

$2,700/wk

7
Beautiful - July and August weeks
Brewster
ID 33965
  • 4 BR
  • 2 baths
  • Sleeps 8

Beautiful - July and August weeks

Distance to beach: 2.5 mi to Linnell Landing and a short walk or drive to a small swimming beach at
5.03 reviews

Off Season:

$500 - $700/night

$3,750 - $4,250/wk

3
Newly renovated, 2 minute walk to freshwater pond.
Brewster
ID 34341
  • 4 BR
  • 2 baths
  • Sleeps 8

Newly renovated, 2 minute walk to freshwater pond.

Distance to beach: walk to pond, Mayflower 6 mi, Paine's Creek 4 mi
4.923 reviews

Off Season:

$350 - $450/night

$1,250 - $2,750/wk

4
4 Bedroom House w/ Deeded Rights to Upper Mill Pond
Upper Mill Pond
ID 35648
  • 4 BR
  • 2 baths
  • Sleeps 8

4 Bedroom House w/ Deeded Rights to Upper Mill Pond

Distance to beach: 100 yds to Upper Mill Pond
5.01 review

Off Season:

$350 - $450/night

$2,150 - $3,350/wk

3
Private Brewster/South Orleans Cape
Brewster
ID 20786
  • 3 BR
  • 2 baths
  • Sleeps 8

Private Brewster/South Orleans Cape

Distance to beach: 1 mile Pleasant Rd Beach and Less than one mile to Pleasant Bay beaches
4.922 reviews

Summer:

$1,600 - $2,400/wk

Off Season:

$300 - $350/night

$1,200 - $2,000/wk

3
Great Location!!  Close to Rail Trail Bike Trail
Brewster
ID 22099
  • 3 BR
  • 2 baths
  • Sleeps 8

Great Location!! Close to Rail Trail Bike Trail

Distance to beach: 2.0 miles Point of Rocks Beach and 2.4 miles Ellis Landing Beach
4.925 reviews
8
Bayside House, Brewster/Orleans, 3 BR, 2 Bath, Central AC
Brewster
ID 20190
  • 3 BR
  • 2 baths
  • Sleeps 8

Bayside House, Brewster/Orleans, 3 BR, 2 Bath, Central AC

Distance to beach: 1.5 miles to Crosby Landing
5.07 reviews

Summer:

$3,205/wk

Off Season:

$1,705 - $3,205/wk

7
Luxury Waterfront Oasis on Private Sunset Beach
Brewster
ID 33328
  • 3 BR
  • 2 baths
  • Sleeps 8

Luxury Waterfront Oasis on Private Sunset Beach

Distance to beach: Waterfront on private, white sandy Sunset Beach
5.041 reviews
OWNER SPECIAL:

2027 Season is now open and off-season is still available. ON THE BAY & private beach, fully A/C.

Summer:

$9,250 - $13,250/wk

$1,000 - $30,000/mo

Off Season:

$2,250 - $8,250/wk

$1,000 - $20,000/mo

7
Blue Sheep Cottage w/ Sheep Pond Private Beach Access
Brewster
ID 39888
  • 3 BR
  • 1 bath
  • Sleeps 8

Blue Sheep Cottage w/ Sheep Pond Private Beach Access

Distance to beach: < 1/2 mi to Sheep Pond and < 3 mi to Crosby Landing
4.911 reviews

Summer:

$2,800 - $3,400/wk

Off Season:

$250 - $400/night

$1,900 - $3,050/wk

7
Private Retreat on 2 Acres; Walk/Bike to 3 Brewster Beaches
Brewster
ID 40197
  • 3 BR
  • 2 baths
  • Sleeps 8

Private Retreat on 2 Acres; Walk/Bike to 3 Brewster Beaches

Distance to beach: 0.9 mi to Saints Landing
5.09 reviews

Summer:

$3,535 - $4,165/wk

Off Season:

$320 - $450/night

$2,485 - $3,535/wk

$8,000 - $10,000/mo

3
Dog-Friendly Home with Deeded Pond Access
Brewster
ID 40748
  • 3 BR
  • 2 baths
  • Sleeps 8

Dog-Friendly Home with Deeded Pond Access

Distance to beach: 3/10 mi to Upper Mill Pond and 3.7 mi to Paine's Creek

Off Season:

$250 - $450/night

$1,680 - $2,080/wk

2
Ideal Fun Family Retreat; Bikes, Arcade, Steps to Playground
Brewster
ID 41928
  • 3 BR
  • 2 baths
  • Sleeps 8

Ideal Fun Family Retreat; Bikes, Arcade, Steps to Playground

Distance to beach: 1.8 mi to Breakwater Beach
5.04 reviews

Summer:

$2,800/wk

Off Season:

$220 - $270/night

$1,800 - $2,800/wk

6
Beautiful Bayside Home Short Walk to Crosby Landing Beach
Brewster
ID 12683
  • 3 BR
  • 2 baths
  • Sleeps 8

Beautiful Bayside Home Short Walk to Crosby Landing Beach

Distance to beach: 3 miles Coastguard Beach and 0-.1 Crosby Landing
4.910 reviews

Summer:

$6,320/wk

Off Season:

$450 - $650/night

$4,775 - $6,250/wk

$3,570 - $4,250/mo

3
Serene Pondfront Retreat with Central AC
Brewster
ID 34964
  • 3 BR
  • 2 baths
  • Sleeps 8

Serene Pondfront Retreat with Central AC

Distance to beach: 1.2 mile walk to Cliff Pond and 1.8 miles to Linnell Landing
4.52 reviews

Summer:

$4,850/wk

Off Season:

$2,850 - $4,350/wk

8
Classic Cape Cod Charm with Modern Comforts
Brewster
ID 40688
  • 3 BR
  • 2 baths
  • Sleeps 8

Classic Cape Cod Charm with Modern Comforts

Distance to beach: 0.9 mi to Point of Rocks Beach
5.09 reviews

Summer:

$4,050 - $4,750/wk

Off Season:

$400/night

$2,750 - $4,050/wk

5
HGTV-Featured Renovated Cape w/ Sunroom, Firepit
Brewster
ID 40941
  • 3 BR
  • 2 baths
  • Sleeps 8

HGTV-Featured Renovated Cape w/ Sunroom, Firepit

Distance to beach: 0.9 mi to Little Pleasant Bay Beach

Off Season:

$500 - $750/night

$2,950/wk

$2,000 - $3,500/mo

3
Single Level, Sun Filled, Family Retreat - 4 Seasons
Brewster
ID 33496
  • 3 BR
  • 2 baths
  • Sleeps 8

Single Level, Sun Filled, Family Retreat - 4 Seasons

Distance to beach: 1.8 mi to Ellis Landing Beach and 2.1 mi to Breakwater Beach
5.013 reviews

Summer:

$4,350/wk

$8,000 - $18,600/mo

Off Season:

$600 - $650/night

$1,650 - $4,350/wk

$3,000 - $15,000/mo

7
Comfy Cape House
6A Brewster
ID 34801
  • 2 BR
  • 2 baths
  • Sleeps 8

Comfy Cape House

Distance to beach: 1.9 mi to Paine's Creek
4.914 reviews

Off Season:

$200 - $325/night

$1,700 - $1,900/wk

4

Brewster vacation rentals that sleep 7

4 Bdrm Home with HEATED Private POOL  &  Pond BEACH
The Highlands on Seymours Pond
ID 21981
  • 4 BR
  • 2 baths
  • Sleeps 7

4 Bdrm Home with HEATED Private POOL & Pond BEACH

Distance to beach: 3.2 Miles Breakwater Beach and 4/10 mile to Seymour Pond Beach
4.916 reviews

Summer:

$3,650/wk

Off Season:

$3,000 - $3,200/wk

4
Ideal Location! Relaxing Setting, Stroll to Bayside Beach
Brewster
ID 8567
  • 3 BR
  • 2 baths
  • Sleeps 7

Ideal Location! Relaxing Setting, Stroll to Bayside Beach

Distance to beach: 4/10 mile to Pineland Park private bayside beach
5.015 reviews

Summer:

$3,165 - $3,365/wk

Off Season:

$1,965 - $3,165/wk

6
Getaway to Trails, Beaches, Shopping and Exploring + Pets
Brewster
ID 34031
  • 3 BR
  • 2 baths
  • Sleeps 7

Getaway to Trails, Beaches, Shopping and Exploring + Pets

Distance to beach: 1.3 mi to Breakwater Beach and 1.3 Sheep Pond
4.924 reviews

Summer:

$2,480 - $3,680/wk

Off Season:

$260 - $325/night

$1,345 - $2,980/wk

7
Charming Brewster farmhouse - ''Vermont by the Sea''
Brewster
ID 36282
  • 3 BR
  • 1 bath
  • Sleeps 7

Charming Brewster farmhouse - ''Vermont by the Sea''

Distance to beach: 1.3 mi to Breakwater Beach and 1.5 mi to Sheep Pond
5.06 reviews
OWNER SPECIAL:

Seasonal rental available 12/1/26-5/31/27. $2250/mo. includes electric/wifi//trash removal.

Summer:

$3,000 - $3,200/wk

4
Ocean Edge Bayside Townhouse; Walk to Beach, Pool and Tennis
Brewster, Ocean Edge Bayside
ID 35545
  • 3 BR
  • 2 baths
  • Sleeps 7

Ocean Edge Bayside Townhouse; Walk to Beach, Pool and Tennis

Distance to beach: 2/10 mile to Ocean Edge Private Beach
5.05 reviews

Off Season:

$3,600 - $4,300/wk

5
Cozy Cottage Walk to Linnell Landing Beach
Brewster
ID 36696
  • 3 BR
  • 1 bath
  • Sleeps 7

Cozy Cottage Walk to Linnell Landing Beach

Distance to beach: 3/10 mi to Linnell Landing
4.98 reviews

Summer:

$3,550 - $4,550/wk

Off Season:

$285 - $495/night

$1,200 - $3,200/wk

2
Distinctive 3 Bedroom With Expansive Screened Porch
Brewster
ID 37021
  • 3 BR
  • 2 baths
  • Sleeps 7

Distinctive 3 Bedroom With Expansive Screened Porch

Distance to beach: 1.9 mi to Saints Landing and 1.7 mi to Breakwater Beach
4.919 reviews

Summer:

$2,985 - $3,185/wk

Off Season:

$2,685 - $2,885/wk

3
Private Beach - 3 Beds, 2 Baths
Brewster
ID 39587
  • 3 BR
  • 2 baths
  • Sleeps 7

Private Beach - 3 Beds, 2 Baths

Distance to beach: 30 Yards to private Bay beach
5.04 reviews

Summer:

$3,750 - $6,800/wk

Off Season:

$1,600 - $3,750/wk

3
Steps from Private Cape Cod Bay Beach
Brewster
ID 39733
  • 3 BR
  • 2 baths
  • Sleeps 7

Steps from Private Cape Cod Bay Beach

Distance to beach: 33 Yards to Private Bay Beach
5.06 reviews

Summer:

$3,500 - $6,650/wk

Off Season:

$2,400 - $3,900/wk

3
Steps to Paine's Creek-The Perfect Vacation Home
Brewster
ID 41654
  • 3 BR
  • 3 baths
  • Sleeps 7

Steps to Paine's Creek-The Perfect Vacation Home

Distance to beach: 0.1 mi to Paine's Creek

Summer:

$7,375 - $10,125/wk

Off Season:

$300 - $650/night

$3,000 - $5,875/wk

2
Waterfront home with gorgeous views, stairs to private dock!
Brewster
ID 17579
  • 3 BR
  • 2 baths
  • Sleeps 7

Waterfront home with gorgeous views, stairs to private dock!

Distance to beach: Pond beach 5 min walk. Bay beaches 10 min drive
5.034 reviews
9
Charming Hideaway at the Lucky Lobster!
Brewster
ID 17733
  • 3 BR
  • 1 bath
  • Sleeps 7

Charming Hideaway at the Lucky Lobster!

Distance to beach: 1/4 mile walk to Cahoon Beach, Long Pond, Harwich
5.04 reviews

Summer:

$2,750 - $3,100/wk

Off Season:

$2,200 - $2,900/wk

$10,000 - $12,000/mo

5
Prime Fall Weeks • Flexible 3-Night Stays
Brewster
ID 24051
  • 2 BR
  • 2 baths
  • Sleeps 7

Prime Fall Weeks • Flexible 3-Night Stays

Distance to beach: 2/10 Saints Landing and 6/10 Robbin's Hill Beach
5.018 reviews

Off Season:

$400 - $600/night

$3,500 - $3,800/wk

7

Brewster vacation rentals that sleep 6

Birdwatcher's Delight
East Brewster
ID 12150
  • 3 BR
  • 1 bath
  • Sleeps 6

Birdwatcher's Delight

Distance to beach: 2 miles to Linnell Landing and 1.4 miles (walk or bike) to Cliff Pond
4.852 reviews

Summer:

$2,500/wk

$8,000/mo

Off Season:

$350 - $400/night

$1,800 - $2,500/wk

$4,500 - $8,000/mo

8
Cobb’s Pond Retreat, and Private Bay Beach Breakwater Acres
Brewster
ID 19784
  • 3 BR
  • 1 bath
  • Sleeps 6

Cobb’s Pond Retreat, and Private Bay Beach Breakwater Acres

Distance to beach: Private Breakwater Acres Bayside Beach )
5.019 reviews
OWNER SPECIAL:

$450 off! Now $3200 from $3500 will include linens ($150). Cleaning, trash, tax not included.

Summer:

$3,825 - $3,925/wk

Off Season:

$150 - $514/night

$1,325 - $3,525/wk

8
Charming Cottage, Walk/Cycle to Beach/Shops/Cafes
Brewster
ID 12130
  • 3 BR
  • 1 bath
  • Sleeps 6

Charming Cottage, Walk/Cycle to Beach/Shops/Cafes

Distance to beach: .7 mile Point of Rocks Beach and 2 miles Paine's Creek
4.738 reviews

Summer:

$299/night

$2,000 - $2,400/wk

Off Season:

$225/night

$1,200 - $1,900/wk

$1,900 - $3,200/mo

2
Pilgrim Pines Beach House
Brewster, North of 6A
ID 16316
  • 3 BR
  • 1 bath
  • Sleeps 6

Pilgrim Pines Beach House

Distance to beach: 200 yards to large private Pilgrim Pines Beach

Summer:

$2,900/wk

Off Season:

$2,400 - $2,950/wk

4
Brewster Home on Quiet Cul-de-Sac near Seymour Pond
Brewster
ID 24986
  • 3 BR
  • 2 baths
  • Sleeps 6

Brewster Home on Quiet Cul-de-Sac near Seymour Pond

Distance to beach: 1/4 mile to Seymour Pond, Freshwater pond
4.923 reviews

Summer:

$2,000 - $2,300/wk

Off Season:

$400 - $500/night

$1,500 - $2,000/wk

3
Newly Renovated Home Steps from Private Sunset Beach
Brewster
ID 25423
  • 3 BR
  • 1 bath
  • Sleeps 6

Newly Renovated Home Steps from Private Sunset Beach

Distance to beach: 40 steps to private, white sandy Sunset Beach
5.045 reviews
OWNER SPECIAL:

2027 is open and off-season avail. Only $1,500/week. Just 1 house off of private beach, fully A/C.

Summer:

$5,700 - $6,700/wk

$1,000 - $20,000/mo

Off Season:

$1,200 - $3,200/wk

$1,000 - $10,000/mo

6
3 Bedroom, 1 1/2 Bath Ranch House
Brewster
ID 21623
  • 3 BR
  • 1 bath
  • Sleeps 6

3 Bedroom, 1 1/2 Bath Ranch House

Distance to beach: 1/2 mile Long Pond and 2 miles Breakwater Beach
4.823 reviews

Summer:

$1,575/wk

$7,500 - $8,000/mo

Off Season:

$175 - $200/night

$1,200 - $1,550/wk

$4,000 - $6,500/mo

2
Serene Seclusion in Brewster
Brewster
ID 35460
  • 3 BR
  • 1 bath
  • Sleeps 6

Serene Seclusion in Brewster

Distance to beach: 1.3 miles Sheep Pond and 3.3 miles Point of Rocks Beach
5 reviews

Summer:

$2,400/wk

Off Season:

$275 - $300/night

$1,700/wk

Private, Pet Friendly, A/C. Close to BREWSTER Bay Beaches
Brewster
ID 38149
  • 3 BR
  • 1 bath
  • Sleeps 6

Private, Pet Friendly, A/C. Close to BREWSTER Bay Beaches

Distance to beach: 0.9 mi to Saints Landing
5.04 reviews

Summer:

$3,250 - $3,350/wk

Off Season:

$200 - $400/night

$1,650 - $3,250/wk

6
Steps from Linnell Landing Beach
Windward Cottage
ID 39445
  • 3 BR
  • 2 baths
  • Sleeps 6

Steps from Linnell Landing Beach

Distance to beach: 30 Yards to private Cape Cod Bay beach
5.03 reviews

Summer:

$4,300 - $6,800/wk

Off Season:

$1,600 - $4,900/wk

2
Peaceful and Charming Home in the Heart of Brewster!
Brewster
ID 39628
  • 3 BR
  • 1 bath
  • Sleeps 6

Peaceful and Charming Home in the Heart of Brewster!

Distance to beach: 2.1 mi to Wixon Memorial and 3 miles to Linnell Landing
5.06 reviews

Summer:

$2,300 - $2,600/wk

Off Season:

$200 - $250/night

$1,500 - $2,300/wk

6
Woodchip - Bike Trail Access, Tennis/Pickleball & AC!
Brewster
ID 40118
  • 3 BR
  • 2 baths
  • Sleeps 6

Woodchip - Bike Trail Access, Tennis/Pickleball & AC!

Distance to beach: 1.6 mi to Crosby Landing and 2.0 Skaket Beach
5.04 reviews

Summer:

$3,800 - $4,150/wk

Off Season:

$2,575 - $3,800/wk

3
Stone's Throw from Beautiful Bay Beach
Brewster
ID 40180
  • 3 BR
  • 2 baths
  • Sleeps 6

Stone's Throw from Beautiful Bay Beach

Distance to beach: 0.2 mi to Linnell Landing
5.03 reviews

Summer:

$3,900 - $4,650/wk

Off Season:

$425 - $550/night

$1,200 - $3,500/wk

4
Quiet, Cozy Retreat on Cape Cod Bay
Brewster
ID 22399
  • 3 BR
  • 2 baths
  • Sleeps 6

Quiet, Cozy Retreat on Cape Cod Bay

Distance to beach: Brewster: 3 miles Paine's Creek and Dennis: Sesuit Beach 1.5 mi.
4.910 reviews

Off Season:

$1,850/wk

6
Charming 3 bedroom ranch - Walk to Saints Beach
Brewster, MA
ID 21492
  • 3 BR
  • 2 baths
  • Sleeps 6

Charming 3 bedroom ranch - Walk to Saints Beach

Distance to beach: 3/10 mi to Saints Beach, 5/10 mi to Mants Beach
5.07 reviews
3
Bayfront Cottage on Private Beach
Brewster
ID 25395
  • 3 BR
  • 1 bath
  • Sleeps 6

Bayfront Cottage on Private Beach

Distance to beach: On a private Bay beach (the Brewster Flats).
5.02 reviews

Off Season:

$3,385/wk

4
Brewster Mountain Retreat  (Blueberry Pond)
Brewster (Blueberry Pond)
ID 33279
  • 3 BR
  • 2 baths
  • Sleeps 6

Brewster Mountain Retreat (Blueberry Pond)

Distance to beach: 1.6 mi to Linnell Landing and < 1/2 mile to private Blueberry Pond Beach
4.922 reviews

Off Season:

$280/night

$2,060 - $3,260/wk

8
Spacious Ocean Edge Condo Just Steps from Rail Trail!
Ocean Edge
ID 36741
  • 3 BR
  • 2 baths
  • Sleeps 6

Spacious Ocean Edge Condo Just Steps from Rail Trail!

Distance to beach: 1.1 mi to Ellis Landing Beach
5.03 reviews

Off Season:

$250 - $350/night

$2,250 - $2,600/wk

3
3 BR Home w/ Central Air - Stroll to the Brewster Bay Flats
North of 6A- Walk to Brewster
ID 35349
  • 3 BR
  • 2 baths
  • Sleeps 6

3 BR Home w/ Central Air - Stroll to the Brewster Bay Flats

Distance to beach: 5/10 mile to Saints Landing and 5/10 mile to Robbin's Hill Beach

Summer:

$4,975/wk

Off Season:

$4,975/wk

3
Remodeled Home Close to Sesuit Harbor
Brewster
ID 39000
  • 3 BR
  • 2 baths
  • Sleeps 6

Remodeled Home Close to Sesuit Harbor

Distance to beach: 3 mi to Upper Mill Pond
5.09 reviews

Off Season:

$1,650/wk

6
Charming Retreat-Walk to Beach, General Store & Bike Trail
Brewster
ID 39868
  • 3 BR
  • 1 bath
  • Sleeps 6

Charming Retreat-Walk to Beach, General Store & Bike Trail

Distance to beach: 0.5 mi to Point of Rocks Beach
5.04 reviews

Off Season:

$2,500/wk

6
Gorgeous Lower Rd. Cottage On 6 Acres. Walk to Beach&6A!
Brewster
ID 28547
  • 2 BR
  • 1 bath
  • Sleeps 6

Gorgeous Lower Rd. Cottage On 6 Acres. Walk to Beach&6A!

Distance to beach: half mile Saints Landing and 1/2 Mile to Saints Landing Beach
5.09 reviews

Summer:

$2,265/wk

Off Season:

$200/night

$1,200 - $2,265/wk

2
Seaside Serenity: Classic Cape Cottage Right Near the Beach!
Brewster
ID 33260
  • 2 BR
  • 1 bath
  • Sleeps 6

Seaside Serenity: Classic Cape Cottage Right Near the Beach!

Distance to beach: 2/10 mile to Ellis Landing Beach
4.98 reviews

Summer:

$2,200 - $2,500/wk

Off Season:

$250 - $350/night

$1,600 - $2,100/wk

4

Brewster vacation rentals that sleep 5

Private Cottage in Sheep Pond Estates
Brewster
ID 25929
  • 3 BR
  • 1 bath
  • Sleeps 5

Private Cottage in Sheep Pond Estates

Distance to beach: 500 yards Sheep Pond and Walk 500 yards to Sheep Pond, Private Beach
5.07 reviews

Summer:

$1,700 - $1,800/wk

Off Season:

$1,200 - $1,700/wk

5
New! Fab Bay View  Steps to Huge Private Beach. 5 star rated
Brewster on the beach
ID 39920
  • 3 BR
  • 1 bath
  • Sleeps 5

New! Fab Bay View Steps to Huge Private Beach. 5 star rated

Distance to beach: 0.1mi to Robbin's Hill Beach and Across the yard and down steps to your own beach
5.01 review
OWNER SPECIAL:

Amazing Views Private beach Monthly special.

Summer:

$5,554 - $5,963/wk

Off Season:

$2,632 - $4,969/wk

9
Charming Historic Home, Walk to the Beach
Brewster
ID 41823
  • 3 BR
  • 1 bath
  • Sleeps 5

Charming Historic Home, Walk to the Beach

Distance to beach: 0.4 mi to Ellis Landing Beach
10 reviews

Summer:

$3,675 - $4,200/wk

$18,000/mo

Off Season:

$200 - $600/night

$1,000 - $3,500/wk

$3,500 - $15,000/mo

5
Stunning Sunsets - Steps from Beach
Brewster
ID 38392
  • 2 BR
  • 1 bath
  • Sleeps 5

Stunning Sunsets - Steps from Beach

Distance to beach: 30 ft to Linnell Landing and 30 Feet to Private Bay Beach
5.04 reviews

Summer:

$3,850 - $6,200/wk

Off Season:

$1,600 - $4,000/wk

3
Sunsets on the Beach
Brewster
ID 40878
  • 2 BR
  • 1 bath
  • Sleeps 5

Sunsets on the Beach

Distance to beach: On private beach next to Linnell Landing, Brewster
5.06 reviews

Summer:

$3,800 - $5,200/wk

Off Season:

$2,000 - $3,900/wk

3
On the Beach
Brewster
ID 41945
  • 2 BR
  • 1 bath
  • Sleeps 5

On the Beach

Distance to beach: on a private beach next to Linnell Landing Beach
5.02 reviews

Summer:

$4,300 - $4,950/wk

Off Season:

$1,650 - $3,800/wk

4

Brewster vacation rentals that sleep 4

Beachfront! Cute Cottage w/ AC on a huge Private Beach!
Brewster Beach
ID 34652
  • 2 BR
  • 1 bath
  • Sleeps 4

Beachfront! Cute Cottage w/ AC on a huge Private Beach!

Distance to beach: your private beach is just out your door. Beautif
5.01 review
OWNER SPECIAL:

Beach Front. Wide safe private beach.100+ hydrandeas!s Fab view of cape cod bay, bridge to Ptown.

Summer:

$4,835 - $5,191/wk

Off Season:

$1,503 - $4,306/wk

4
 Private Beach Wifi Bay view
Brewster
ID 34718
  • 2 BR
  • 1 bath
  • Sleeps 4

Private Beach Wifi Bay view

Distance to beach: On a Private beach. 1 min walk to beach stairs
5.02 reviews

Summer:

$4,734 - $5,111/wk

Off Season:

$1,128 - $4,236/wk

11
Private Beachfront   sunset cottage on bluff . Bay views
Brewster beachfront
ID 30177
  • 2 BR
  • 1 bath
  • Sleeps 4

Private Beachfront sunset cottage on bluff . Bay views

Distance to beach: On a 360 ft gorgeous Safe Private Beach
5.06 reviews
OWNER SPECIAL:

On a private beach. Best view on the Cape!

Summer:

$5,290 - $5,679/wk

Off Season:

$2,506 - $4,733/wk

5
Charming Beach Cottage Retreat - Walk to Paines Creek Beach
West Brewster-North of 6A
ID 36330
  • 2 BR
  • 1 bath
  • Sleeps 4

Charming Beach Cottage Retreat - Walk to Paines Creek Beach

Distance to beach: 4/10 mi to Paine's Creek
4.810 reviews

Summer:

$2,575/wk

Off Season:

$2,325 - $2,400/wk

5
Brewster Rail Trail Cottage 2 Bedrooms 1.5 Baths
Brewster
ID 33617
  • 2 BR
  • 1 bath
  • Sleeps 4

Brewster Rail Trail Cottage 2 Bedrooms 1.5 Baths

Distance to beach: 1.0 mile to Linnell Landing and 1.2 miles to Flax Pond
5.03 reviews
3
Updated With AC, King Bed, Pool Passes
Ocean Edge
ID 35649
  • 2 BR
  • 2 baths
  • Sleeps 4

Updated With AC, King Bed, Pool Passes

Distance to beach: 2.0 mi to Ellis Landing Beach
10 reviews
5
Cranberry Cottage: Cozy, Convenient, Charming, and Cool!
West Brewster
ID 41031
  • 2 BR
  • 1 bath
  • Sleeps 4

Cranberry Cottage: Cozy, Convenient, Charming, and Cool!

Distance to beach: 1.1 mi to Paine's Creek
1 review

Summer:

$2,240/wk

Off Season:

$210 - $260/night

$1,340 - $2,240/wk

$2,000 - $9,000/mo

6
Quiet Cape Getaway | Private Deck | Pet Friendly
South Orleans
ID 42038
  • 1 BR
  • 1 bath
  • Sleeps 4

Quiet Cape Getaway | Private Deck | Pet Friendly

Distance to beach: 5.8 mi Nauset Beach and 2.2 mi to Little Pleasant Bay Beach
2 reviews

Summer:

$200/night

$1,520 - $1,870/wk

Off Season:

$200/night

$1,520/wk

2

Brewster vacation rentals that sleep 3

New to Market!  Sweet 1 Bedroom Right on Cape Cod Bay Beach
Brewster
ID 41808
  • 1 BR
  • 1 bath
  • Sleeps 3

New to Market! Sweet 1 Bedroom Right on Cape Cod Bay Beach

Distance to beach: 300 ft to Linnell Landing and a few steps from Linger Longer private beach.
4.52 reviews

Summer:

$2,987 - $3,966/wk

Off Season:

$1,442 - $3,090/wk

5
Brewster Cozy 1 Bedroom Loft
Brewster
ID 41881
  • 1 BR
  • 1 bath
  • Sleeps 3

Brewster Cozy 1 Bedroom Loft

Distance to beach: 0.8 mi to Sheep Pond and 2 miles Linnell Landing

Summer:

$1,700/wk

Off Season:

$100 - $150/night

$1,200 - $1,400/wk

Brewster vacation rentals that sleep 2

Wright Studio by the Bay (Sunday to Sunday rental)
Brewster
ID 2932
  • 1 BR
  • 1 bath
  • Sleeps 2

Wright Studio by the Bay (Sunday to Sunday rental)

Distance to beach: half mile Ellis Landing Beach and less than 1/10 mile to private bay beach
4.914 reviews

Summer:

$1,400/wk

Off Season:

$150/night

$1,050/wk

4
CapeCodProperty 121
Brewster
ID 35725
  • 1 BR
  • 1 bath
  • Sleeps 2

CapeCodProperty 121

Distance to beach: 1.1 mi to Crosby Landing

Summer:

$259/night

$2,302/wk

Off Season:

$58 - $259/night

$895 - $2,302/wk

2