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Orleans Vacation Rentals

170 properties
Orleans Guide

Orleans vacation rentals that sleep 20

Private estate with 2 homes, new pool/outdoor area.
East Orleans
ID 35619
  • 11 BR
  • 8 baths
  • Sleeps 20

Private estate with 2 homes, new pool/outdoor area.

Distance to beach: 2.0 mi to Nauset Beach
5.03 reviews

Summer:

$24,500/wk

Off Season:

$1,500 - $2,800/night

$13,000 - $24,500/wk

2

Orleans vacation rentals that sleep 19

Waterfront Estate with Private Beach & Brand New Pool
Orleans
ID 19054
  • 9 BR
  • 5 baths
  • Sleeps 19

Waterfront Estate with Private Beach & Brand New Pool

Distance to beach: short path leads down the bluff to private beach
5.036 reviews

Summer:

$3,000 - $31,000/wk

Off Season:

$4,000/night

$20,000 - $28,000/wk

3

Orleans vacation rentals that sleep 18

Orleans vacation rentals that sleep 16

Executive Waterfront Luxury Estate; Heated Pool; 6000 Sq.ft.
East Orleans
ID 14224
  • 4 BR
  • 6 baths
  • Sleeps 16

Executive Waterfront Luxury Estate; Heated Pool; 6000 Sq.ft.

Distance to beach: Beachfront with Private Inlet Beach
5.011 reviews
OWNER SPECIAL:

Experience Cape Cod at this Luxury estate in 2027, Inquire now to get a quote with SPECIAL RATES!

Summer:

$20,780 - $27,780/wk

$120,000/mo

Off Season:

$11,780 - $15,780/wk

$60,000 - $120,000/mo

5

Orleans vacation rentals that sleep 15

Parsons Beach Retreat,Fully Renovated,Hot Tub, Bike to Beach
East Orleans
ID 36765
  • 7 BR
  • 8 baths
  • Sleeps 15

Parsons Beach Retreat,Fully Renovated,Hot Tub, Bike to Beach

Distance to beach: 1.5 mi to Nauset Beach and 1.2 mi to Crystal Lake

Summer:

$10,549 - $13,549/wk

Off Season:

$10,500 - $11,349/wk

5

Orleans vacation rentals that sleep 14

Private Beach 6 Bedroom Newly Renovated
Orleans
ID 21276
  • 6 BR
  • 6 baths
  • Sleeps 14

Private Beach 6 Bedroom Newly Renovated

Distance to beach: 150' walk to Little Pleasant Bay Beach
4.54 reviews

Summer:

$12,200/wk

Off Season:

$11,200/wk

3

Orleans vacation rentals that sleep 12

Nauset Beach Retreat- location! walk to beach
Orleans
ID 21847
  • 5 BR
  • 4 baths
  • Sleeps 12

Nauset Beach Retreat- location! walk to beach

Distance to beach: Sandy Walking Path to Nauset Beach
5.08 reviews

Summer:

$12,000 - $13,000/wk

4
Privacy. Comfort. Style. Unique Property w Resort Amenities!
East Orleans
ID 32168
  • 5 BR
  • 5 baths
  • Sleeps 12

Privacy. Comfort. Style. Unique Property w Resort Amenities!

Distance to beach: 2 miles Nauset Beach and Nauset Inlet w/ sandy beach is steps away & lovely
5.026 reviews

Summer:

$14,000 - $16,000/wk

Off Season:

$13,500 - $15,500/wk

6
Nauset Beach House - Big, Beautiful, Views, Walk To Beach!
Nauset Heights
ID 29075
  • 4 BR
  • 4 baths
  • Sleeps 12

Nauset Beach House - Big, Beautiful, Views, Walk To Beach!

Distance to beach: Nauset Beach and Nauset Inlet Nauset Beach
5.025 reviews

Summer:

$8,350 - $9,350/wk

$33,500 - $40,500/mo

Off Season:

$3,350 - $7,850/wk

$3,000 - $29,000/mo

10
Heated Pool~1 mile to Nauset Beach/Dogs Welcome!
Orleans
ID 38175
  • 4 BR
  • 2 baths
  • Sleeps 12

Heated Pool~1 mile to Nauset Beach/Dogs Welcome!

Distance to beach: 1.6 mi to Nauset Beach
5.04 reviews

Summer:

$5,900 - $7,650/wk

Off Season:

$2,900 - $5,900/wk

4
E Orleans classic w boat house & heated pool. Walk to water
East Orleans, Mill Pond
ID 29199
  • 4 BR
  • 3 baths
  • Sleeps 12

E Orleans classic w boat house & heated pool. Walk to water

Distance to beach: 2.4 miles Nauset Beach and 1/10 miles Robert's Cove/Mill Pond
5.01 review

Off Season:

$4,500 - $9,500/wk

8

Orleans vacation rentals that sleep 11

East Orleans Elegance!
East Orleans
ID 36762
  • 5 BR
  • 3 baths
  • Sleeps 11

East Orleans Elegance!

Distance to beach: 1.2 mi to Nauset Beach
1 review

Off Season:

$5,000/wk

Bright waterfront haven with AC and heavenly 100° views
Grandview
ID 31120
  • 4 BR
  • 3 baths
  • Sleeps 11

Bright waterfront haven with AC and heavenly 100° views

Distance to beach: 0.8 miles to Nauset Beach and 4.6 miles to Skaket Beach
5.053 reviews

Summer:

$7,950/wk

Off Season:

$357 - $1,136/night

$2,400 - $7,950/wk

8

Orleans vacation rentals that sleep 10

Large Classic Cape House with private beach
East Orleans
ID 25613
  • 6 BR
  • 3 baths
  • Sleeps 10

Large Classic Cape House with private beach

Distance to beach: 9 minute drive to Nauset Beach and 13 minute drive to Skaket Beach
5.015 reviews

Summer:

$5,900 - $6,000/wk

Off Season:

$5,600 - $5,900/wk

2
Private Waterfront on Pleasant Bay
Orleans
ID 19102
  • 5 BR
  • 3 baths
  • Sleeps 10

Private Waterfront on Pleasant Bay

Distance to beach: right out front
5.025 reviews

Summer:

$7,500 - $10,500/wk

Off Season:

$2,000/night

$5,000 - $7,000/wk

2
Nauset Heights Waterfront!
East Orleans
ID 34325
  • 5 BR
  • 2 baths
  • Sleeps 10

Nauset Heights Waterfront!

Distance to beach: Private Stairway to Nauset Beach
2 reviews

Summer:

$6,300/wk

Off Season:

$3,300 - $5,300/wk

5BR Retreat w/ Hot Tub, Firepit, Near Beaches, Dining, Golf!
Orleans
ID 40785
  • 5 BR
  • 2 baths
  • Sleeps 10

5BR Retreat w/ Hot Tub, Firepit, Near Beaches, Dining, Golf!

Distance to beach: 3.6 Nauset Beach and 1.7 Skaket Beach
19 reviews
OWNER SPECIAL:

10% Off Bookings with from We Need a Vacation.

Summer:

$4,795 - $9,395/wk

$25,000 - $30,000/mo

Off Season:

$200 - $500/night

$2,395 - $6,395/wk

$3,000 - $20,000/mo

12
Pochet Retreat — Private Nauset Beach Access
Orleans
ID 41535
  • 5 BR
  • 3 baths
  • Sleeps 10

Pochet Retreat — Private Nauset Beach Access

Distance to beach: 0.5 mi to Pochet Association at Nauset Beach
5.01 review

Off Season:

$4,200/wk

8
1.6 acres w/ private fresh & salt water access and rec room
Mayflower Point
ID 7598
  • 4 BR
  • 2 baths
  • Sleeps 10

1.6 acres w/ private fresh & salt water access and rec room

Distance to beach: 3.8 mi.10 min. Nauset Beach and 4.2 mi. 14 min. Skaket Beach
5.022 reviews
OWNER SPECIAL:

Check out our off season availability & pricing!

Summer:

$4,200/wk

$13,000 - $15,000/mo

Off Season:

$3,900 - $4,200/wk

$13,000 - $15,000/mo

3
California Contemporary, Walk to Beach, 1.3 Wooded Acres
South Orleans
ID 23766
  • 4 BR
  • 2 baths
  • Sleeps 10

California Contemporary, Walk to Beach, 1.3 Wooded Acres

Distance to beach: 3 houses away Quanset Harbor Club Beach and 3 houses from private assn beach on Pleasant Bay
5.060 reviews

Summer:

$4,950/wk

Off Season:

$495 - $695/night

$3,464 - $4,950/wk

9
Nauset Lookout - 4 Minute walk to Nauset Beach, Ocean View
East Orleans
ID 22357
  • 4 BR
  • 2 baths
  • Sleeps 10

Nauset Lookout - 4 Minute walk to Nauset Beach, Ocean View

Distance to beach: 2/10 of a mile to Nauset Beach
4.915 reviews

Summer:

$6,389 - $9,571/wk

Off Season:

$3,168 - $7,485/wk

5
Spacious Modern, Stylish 5-Star Retreat
Orleans
ID 32188
  • 4 BR
  • 3 baths
  • Sleeps 10

Spacious Modern, Stylish 5-Star Retreat

Distance to beach: ~ 2 miles to Skaket Beach and ~ 2 miles to Nauset Beach
5.022 reviews

Summer:

$7,000 - $7,100/wk

Off Season:

$5,300 - $7,000/wk

5
Poolside Oasis
Orleans
ID 37246
  • 4 BR
  • 2 baths
  • Sleeps 10

Poolside Oasis

Distance to beach: 2.3 mi to Crystal Lake

Summer:

$6,456 - $10,560/wk

Off Season:

$3,338 - $6,279/wk

Endless Summer with Kayaks, Bikes, and Private Yard
Orleans
ID 37150
  • 4 BR
  • 3 baths
  • Sleeps 10

Endless Summer with Kayaks, Bikes, and Private Yard

Distance to beach: 0.7 mi to Little Pleasant Bay Beach and 7 minute drive Skaket Beach
5.02 reviews

Off Season:

$250 - $479/night

$1,600/wk

2
East Orleans Waterfront Vacation Haven, Sleeps 10
East Orleans
ID 39511
  • 4 BR
  • 2 baths
  • Sleeps 10

East Orleans Waterfront Vacation Haven, Sleeps 10

Distance to beach: 1.7 mi to Nauset Beach and 4 mi to Skaket Beach
5.03 reviews

Summer:

$8,000 - $8,500/wk

Off Season:

$650 - $850/night

$4,000 - $8,000/wk

$8,000/mo

6
Near Crystal Lake
Orleans
ID 36102
  • 4 BR
  • 3 baths
  • Sleeps 10

Near Crystal Lake

Distance to beach: .8 mi to Crystal Lake

Summer:

$4,300/wk

No Regrets - A Cozy Cape Cod Beach House in Orleans
Orleans
ID 41659
  • 4 BR
  • 3 baths
  • Sleeps 10

No Regrets - A Cozy Cape Cod Beach House in Orleans

Distance to beach: 4.8 mi to Nauset Beach and 0.9 mi to Skaket Beach

Summer:

$6,000/wk

Off Season:

$857/night

$6,000/wk

8
Charming Cape Home - Ideal for 2 Families
South Orleans
ID 33497
  • 4 BR
  • 2 baths
  • Sleeps 10

Charming Cape Home - Ideal for 2 Families

Distance to beach: 3 miles to Nauset Beach and 3 miles to Skaket Beach
5.05 reviews

Summer:

$4,000 - $5,000/wk

Off Season:

$4,000/wk

5
CLEAN and spacious home for families and well-behaving dogs!
East Orleans
ID 19116
  • 3 BR
  • 2 baths
  • Sleeps 10

CLEAN and spacious home for families and well-behaving dogs!

Distance to beach: 1/2 mile walk to Nauset Beach
5.08 reviews

Summer:

$3,100 - $3,500/wk

Off Season:

$1,500 - $3,100/wk

4
Water views, private waterfront, 2.7 mi. to Nauset Beach!
Orleans
ID 20703
  • 3 BR
  • 2 baths
  • Sleeps 10

Water views, private waterfront, 2.7 mi. to Nauset Beach!

Distance to beach: 100 ft. to small, private beach on Town Cove
4.828 reviews

Summer:

$4,400 - $4,900/wk

Off Season:

$300 - $700/night

$2,100 - $4,400/wk

3

Orleans vacation rentals that sleep 9

Orleans Waterview 4 bedroom with private beach access
Pochet community, East Orleans
ID 29730
  • 4 BR
  • 2 baths
  • Sleeps 9

Orleans Waterview 4 bedroom with private beach access

Distance to beach: 4/10 mile to private section of Nauset Beach
5.01 review

Off Season:

$3,850 - $4,550/wk

4

Orleans vacation rentals that sleep 8

Water Views, Walk to Nauset Beach, 3 King Master Suites
East Orleans
ID 1164
  • 4 BR
  • 3 baths
  • Sleeps 8

Water Views, Walk to Nauset Beach, 3 King Master Suites

5.033 reviews

Summer:

$8,250/wk

Off Season:

$4,750/wk

8
A Tranquil, Convenient Location in South Orleans
Orleans
ID 21116
  • 4 BR
  • 2 baths
  • Sleeps 8

A Tranquil, Convenient Location in South Orleans

Distance to beach: 4 miles Skaket Beach and 4 miles Nauset Beach
4.936 reviews

Summer:

$3,100/wk

2
Charming Home, Great for families, Easy walk to Nauset Beach
East Orleans
ID 25043
  • 4 BR
  • 2 baths
  • Sleeps 8

Charming Home, Great for families, Easy walk to Nauset Beach

Distance to beach: 1/3 mile from Nauset Beach
5.028 reviews

Summer:

$3,575 - $3,975/wk

Off Season:

$470 - $490/night

$3,575/wk

4
Bay Front, Gorgeous views, Private Beach Access
Orleans
ID 28723
  • 4 BR
  • 2 baths
  • Sleeps 8

Bay Front, Gorgeous views, Private Beach Access

Distance to beach: 1/2 mile to Skaket Beach and 4.5 miles Nauset Beach
4.920 reviews

Off Season:

$650 - $850/night

$4,125 - $5,925/wk

3
Waterfront, Four Bedroom Classic Cape With Private Beach
Orleans
ID 33258
  • 4 BR
  • 3 baths
  • Sleeps 8

Waterfront, Four Bedroom Classic Cape With Private Beach

Distance to beach: Private beach on Little Pleasant Bay
5.03 reviews

Summer:

$6,500 - $7,800/wk

Off Season:

$4,000 - $7,000/wk

6
RENOVATED Beautiful Home-Dog Friendly! NEW KITCHEN!
Orleans
ID 35920
  • 4 BR
  • 2 baths
  • Sleeps 8

RENOVATED Beautiful Home-Dog Friendly! NEW KITCHEN!

Distance to beach: 4 miles Nauset Beach and 2 miles Skaket Beach
5.027 reviews

Summer:

$3,750 - $5,000/wk

Off Season:

$350 - $500/night

$1,750 - $3,000/wk

6
A Nauset Heights Gem / Walk to Nauset Beach
East Orleans
ID 38255
  • 4 BR
  • 3 baths
  • Sleeps 8

A Nauset Heights Gem / Walk to Nauset Beach

Distance to beach: .3mi Private Area of Nauset Beach; .6mi to Nauset
5.022 reviews

Summer:

$6,300 - $7,300/wk

Off Season:

$3,800 - $5,800/wk

3
Central AC, Spacious Home, Walk to Lake, Near Nauset
Orleans
ID 38681
  • 4 BR
  • 2 baths
  • Sleeps 8

Central AC, Spacious Home, Walk to Lake, Near Nauset

Distance to beach: 3 mi to Nauset Beach and 3/10 mi to Crystal Lake
5.027 reviews

Off Season:

$1,800 - $3,400/wk

2
Fantastic Home Open Floor Plan Walk to Cove Easy Kayaking
East Orleans
ID 5445
  • 4 BR
  • 3 baths
  • Sleeps 8

Fantastic Home Open Floor Plan Walk to Cove Easy Kayaking

Distance to beach: 2.5 miles Nauset Beach and Short 200 yd wk to Nauset Inlet on Roberts Cove
4.98 reviews
9
WiWaSa (Wind, Water, Sand)
Orleans
ID 10909
  • 4 BR
  • 2 baths
  • Sleeps 8

WiWaSa (Wind, Water, Sand)

Distance to beach: 1/20 mile to Town Landing
4.01 review

Off Season:

$2,600 - $2,700/wk

4
Waterview Sunsets from Deck--Spacious Lakefront in Orleans
Orleans
ID 21757
  • 4 BR
  • 3 baths
  • Sleeps 8

Waterview Sunsets from Deck--Spacious Lakefront in Orleans

Distance to beach: less than 4 miles to Nauset Beach
4.65 reviews

Off Season:

$2,700 - $3,000/wk

5
Waterfront Paradise~Panoramic Water Views, Dock, AC & Kayaks
East Orleans
ID 16949
  • 4 BR
  • 2 baths
  • Sleeps 8

Waterfront Paradise~Panoramic Water Views, Dock, AC & Kayaks

Distance to beach: 1.5 miles to Orleans main ocean beach, Nauset Nauset Beach and Directly on Meeting House Pond; 5min drive, Nauset
5.012 reviews

Summer:

$1,071/night

$7,497/wk

Off Season:

$6,497 - $7,497/wk

3
MacLean Studio
Orleans
ID 41931
  • 4 BR
  • 2 baths
  • Sleeps 8

MacLean Studio

Distance to beach: 2 miles Nauset Beach and 3 miles Skaket Beach

Summer:

$4,575/wk

Off Season:

$400/night

$3,075/wk

On the Bike Path, Near Skaket Beach, A/C
Orleans
ID 18653
  • 3 BR
  • 3 baths
  • Sleeps 8

On the Bike Path, Near Skaket Beach, A/C

Distance to beach: 9/10 mi. to Skaket Beach and 4 mi. to Nauset Beach
5.023 reviews

Summer:

$425 - $450/night

$3,135 - $3,335/wk

Off Season:

$225 - $365/night

$1,735 - $3,235/wk

5
Available: June 12-19; June 19-26 & Aug 28-Sept 4
9 R Pond Road, Orleans
ID 19124
  • 3 BR
  • 3 baths
  • Sleeps 8

Available: June 12-19; June 19-26 & Aug 28-Sept 4

Distance to beach: Crystal Lake Access at end of our path Crystal Lake and 2 miles Nauset Beach
5.022 reviews

Off Season:

$4,400/wk

$5,200/mo

9
Fits 2 Families, 3 bedroom, Kid & Dog Friendly, Charming
Orleans
ID 29389
  • 3 BR
  • 2 baths
  • Sleeps 8

Fits 2 Families, 3 bedroom, Kid & Dog Friendly, Charming

Distance to beach: 3.4 mi Skaket Beach and 4.1 mi Nauset Beach
5.018 reviews
OWNER SPECIAL:

Two hot summer weeks still available, book now before they are gone!!!

Summer:

$715 - $875/night

$5,300 - $6,000/wk

$6,000 - $20,000/mo

Off Season:

$300 - $700/night

$2,300 - $4,800/wk

$2,000 - $7,000/mo

8
Spacious Town Cove Beauty with AC & Cove Views
East Orleans
ID 32571
  • 3 BR
  • 3 baths
  • Sleeps 8

Spacious Town Cove Beauty with AC & Cove Views

Distance to beach: 3 miles Nauset Beach and 3.5 miles Skaket Beach
4.99 reviews

Summer:

$4,200 - $4,600/wk

Off Season:

$400 - $500/night

$2,700 - $4,200/wk

Reconstructed History
Orleans
ID 29810
  • 3 BR
  • 2 baths
  • Sleeps 8

Reconstructed History

Distance to beach: 2.6 miles to Nauset Beach

Summer:

$6,930/wk

Off Season:

$6,930/wk

Upscale East Orleans Home- 5 minutes to Nauset Beach!
East Orleans
ID 33655
  • 3 BR
  • 2 baths
  • Sleeps 8

Upscale East Orleans Home- 5 minutes to Nauset Beach!

Distance to beach: 1.5 miles Nauset Beach and 4.5 miles Skaket Beach
5.024 reviews

Summer:

$4,350 - $5,250/wk

Off Season:

$450/night

$3,350 - $4,350/wk

7
Pleasant Bay with Private Beach Use
Orleans
ID 35950
  • 3 BR
  • 3 baths
  • Sleeps 8

Pleasant Bay with Private Beach Use

Distance to beach: 3/10 mi to Little Pleasant Bay Beach
13 reviews

Summer:

$7,400 - $8,100/wk

Off Season:

$675 - $1,000/night

$3,900 - $8,100/wk

$6,500/mo

6
Locust Retreat
Centrally Located
ID 36017
  • 3 BR
  • 2 baths
  • Sleeps 8

Locust Retreat

Distance to beach: 3.7 mi Nauset Beach and 1.7 mi to Skaket Beach
5.01 review

Off Season:

$250/night

$1,200 - $1,600/wk

3
Hydrangea Haven - Walk to Town Cove for Clamming & Kayaking
Orleans
ID 41208
  • 3 BR
  • 2 baths
  • Sleeps 8

Hydrangea Haven - Walk to Town Cove for Clamming & Kayaking

Distance to beach: 2.9 Nauset Beach and Walk to Town Cove for Kayaking
8 reviews

Off Season:

$500 - $900/night

$3,000 - $4,500/wk

$9,000 - $15,000/mo

6

Orleans vacation rentals that sleep 7

The Salty Sweet Cottage
Orleans
ID 37738
  • 4 BR
  • 1 bath
  • Sleeps 7

The Salty Sweet Cottage

Distance to beach: 4.3 miles Nauset Beach and .8 mile Skaket Beach
5.021 reviews

Summer:

$3,400 - $3,500/wk

Off Season:

$3,350 - $3,400/wk

6
East Orleans Home
East Orleans
ID 11853
  • 3 BR
  • 2 baths
  • Sleeps 7

East Orleans Home

Distance to beach: about 1.25 miles to Nauset Beach
5.06 reviews

Summer:

$1,200 - $1,700/wk

Off Season:

$1,200/wk

5
Colorful, Quiet and Convenient with A/C
Orleans
ID 14560
  • 3 BR
  • 1 bath
  • Sleeps 7

Colorful, Quiet and Convenient with A/C

Distance to beach: 2 miles Skaket Beach and 2 miles Nauset Beach
4.918 reviews

Summer:

$2,300 - $2,325/wk

Off Season:

$1,400 - $2,300/wk

6
Waterfront ''Coveside Oasis'', Spectacular Sunset Views!
Orleans
ID 20336
  • 3 BR
  • 1 bath
  • Sleeps 7

Waterfront ''Coveside Oasis'', Spectacular Sunset Views!

Distance to beach: Approx. 2 miles to Nauset Beach
4.931 reviews

Summer:

$3,950/wk

Off Season:

$3,495/wk

8
Skaket Beach at its Best--Central AC--Walk to the Beach
Orleans
ID 27952
  • 3 BR
  • 2 baths
  • Sleeps 7

Skaket Beach at its Best--Central AC--Walk to the Beach

Distance to beach: 4/10 of a mile to Skaket Beach
5.021 reviews

Summer:

$3,400 - $3,600/wk

Off Season:

$2,650 - $3,600/wk

3
Nauset Escape- Close to Ocean Beach
East Orleans
ID 34264
  • 3 BR
  • 2 baths
  • Sleeps 7

Nauset Escape- Close to Ocean Beach

Distance to beach: Less than a mile to Nauset Beach
4.919 reviews

Summer:

$3,250 - $3,950/wk

Off Season:

$2,750 - $3,250/wk

Bakers Pond Retreat (Asp-1250)
Orleans
ID 30984
  • 3 BR
  • 2 baths
  • Sleeps 7

Bakers Pond Retreat (Asp-1250)

Distance to beach: 1/10 mile to Bakers Pond
5.01 review

Summer:

$2,200/wk

Off Season:

$1,900 - $2,000/wk

2026 OPEN WEEKS: June 26-July 3 & July 3-10 Fri-Fri
9 Pond Road, Orleans
ID 14519
  • 3 BR
  • 1 bath
  • Sleeps 7

2026 OPEN WEEKS: June 26-July 3 & July 3-10 Fri-Fri

Distance to beach: Access Crystal Lake at end of our path Crystal Lake
5.023 reviews

Off Season:

$2,500 - $3,300/wk

8
East Orleans Aerie Between 2 Ocean Beaches! Dogs welcome!
East Orleans
ID 37425
  • 3 BR
  • 2 baths
  • Sleeps 7

East Orleans Aerie Between 2 Ocean Beaches! Dogs welcome!

Distance to beach: 6/10 mi to Harbor Cove and 2.8 mi to Nauset Beach
5.010 reviews

Summer:

$4,500 - $5,750/wk

Off Season:

$598 - $798/night

$3,000 - $5,500/wk

4
Spacious cottage near Pleasant Bay with new outdoor sauna
South Orleans
ID 12283
  • 2 BR
  • 2 baths
  • Sleeps 7

Spacious cottage near Pleasant Bay with new outdoor sauna

Distance to beach: 5 miles Skaket Beach and 5 miles Nauset Beach
4.914 reviews

Off Season:

$1,530 - $1,730/wk

$5,500 - $6,500/mo

3

Orleans vacation rentals that sleep 6

Private fun house between Nauset and Skaket beaches
East Orleans
ID 30951
  • 4 BR
  • 3 baths
  • Sleeps 6

Private fun house between Nauset and Skaket beaches

Distance to beach: 2.5 miles Nauset Beach and 2.5 miles Skaket Beach
4.920 reviews

Summer:

$2,300/wk

Off Season:

$1,800 - $2,300/wk

2
Comfortable Cottage in Exclusive Nauset Heights
East Orleans - Nauset Heights
ID 13418
  • 3 BR
  • 1 bath
  • Sleeps 6

Comfortable Cottage in Exclusive Nauset Heights

Distance to beach: 10 Min Walk to North End of Nauset Beach and 5 Minute walk to Priscilla Landing
4.921 reviews

Off Season:

$217 - $475/night

$1,735/wk

4
Serenity: Recent addition to cottage near Nauset Beach
East Orleans
ID 27066
  • 3 BR
  • 1 bath
  • Sleeps 6

Serenity: Recent addition to cottage near Nauset Beach

Distance to beach: 1.5 miles to Nauset Beach
5.024 reviews

Summer:

$2,250 - $2,550/wk

Off Season:

$2,050/wk

4
Bayberry House - Dog Friendly, Central AC, Near Nauset Beach
Orleans
ID 26865
  • 3 BR
  • 2 baths
  • Sleeps 6

Bayberry House - Dog Friendly, Central AC, Near Nauset Beach

Distance to beach: 1/2 mile to Meetinghouse Pond!
4.65 reviews

Summer:

$3,266 - $4,876/wk

Off Season:

$2,179 - $3,266/wk

6
Charming Seaside Cottage near Skaket Beach
Orleans
ID 28026
  • 3 BR
  • 1 bath
  • Sleeps 6

Charming Seaside Cottage near Skaket Beach

Distance to beach: less than 1/10 mile to Skaket Beach
5.09 reviews

Summer:

$2,700/wk

6
Fabulous home...Mint condition...Village location!
East Orleans
ID 31054
  • 3 BR
  • 2 baths
  • Sleeps 6

Fabulous home...Mint condition...Village location!

Distance to beach: 1.5 miles to Nauset Beach
5.04 reviews

Summer:

$4,200/wk

Off Season:

$3,100 - $3,700/wk

3
East Orleans - Close to Asa's Landing (1/2 mile)
E. Orleans - Tonset Area
ID 34839
  • 3 BR
  • 2 baths
  • Sleeps 6

East Orleans - Close to Asa's Landing (1/2 mile)

Distance to beach: 2.6 mi to Nauset Beach and 4 mi to Skaket Beach
5.06 reviews

Summer:

$3,963/wk

$14,000 - $15,000/mo

Off Season:

$250 - $500/night

$1,463 - $3,463/wk

$3,750 - $7,500/mo

Walk to private beach and relax in open & updated cottage
Orleans
ID 34184
  • 3 BR
  • 2 baths
  • Sleeps 6

Walk to private beach and relax in open & updated cottage

Distance to beach: 4/10 mile Skaket Beach and Private bay beach
5.022 reviews

Summer:

$4,550/wk

Off Season:

$300 - $600/night

4
Parson's Cottage
East Orleans
ID 36644
  • 3 BR
  • 2 baths
  • Sleeps 6

Parson's Cottage

Distance to beach: 1.5 mi to Nauset Beach and 1.3 mi to Crystal Lake
3.01 review
OWNER SPECIAL:

Looking for overflow space over Thanksgiving. Consider The Parsons Cottage, call us for details.

Summer:

$3,200 - $3,995/wk

Off Season:

$385 - $585/night

$1,350 - $3,200/wk

$2,750 - $3,950/mo

4
Quintessential Cape Cottage in Nauset Heights
Nauset Heights
ID 37565
  • 3 BR
  • 1 bath
  • Sleeps 6

Quintessential Cape Cottage in Nauset Heights

Distance to beach: 1/4 mi to Nauset Beach and 2/10 mi Private North Nauset Beach
5.02 reviews

Summer:

$2,560 - $2,750/wk

Off Season:

$225 - $279/night

$1,970 - $2,465/wk

5
Dog Friendly/Centrally Located/Walk to Eldredge Park
Orleans
ID 37090
  • 3 BR
  • 1 bath
  • Sleeps 6

Dog Friendly/Centrally Located/Walk to Eldredge Park

Distance to beach: 3.2 Nauset Beach and 1.6 mi to Skaket Beach
5.01 review

Summer:

$2,350 - $3,050/wk

5
Spacious E. Orleans home by Nauset Beach, walk to pond
East Orleans
ID 39187
  • 3 BR
  • 2 baths
  • Sleeps 6

Spacious E. Orleans home by Nauset Beach, walk to pond

Distance to beach: 4.2 mi to Skaket Beach and 2.3 mi to Pochet Association at Nauset Beach
5.03 reviews

Summer:

$3,270 - $3,470/wk

Off Season:

$350 - $380/night

$2,220 - $2,870/wk

$6,500/mo

Captain Seth Sparrow Main House/Salt Water Access; Kayaks
South Orleans
ID 40012
  • 3 BR
  • 2 baths
  • Sleeps 6

Captain Seth Sparrow Main House/Salt Water Access; Kayaks

Distance to beach: 350 yds to Arey's Pond,deeded;1 mi to Crystal Lake
3 reviews

Summer:

$4,030/wk

Off Season:

$2,430 - $3,630/wk

2
NEW listing: Bright & Cozy Retreat Near Nauset Beach
Orleans
ID 41624
  • 3 BR
  • 2 baths
  • Sleeps 6

NEW listing: Bright & Cozy Retreat Near Nauset Beach

Distance to beach: 2.5 mi Nauset Beach and 3 mi Skaket Beach
5.01 review

Summer:

$3,000 - $3,650/wk

Off Season:

$300 - $460/night

$2,000 - $7,750/wk

6
East Orleans Retreat w/ Wraparound Deck, 1 mi to Nauset
Orleans
ID 42075
  • 3 BR
  • 1 bath
  • Sleeps 6

East Orleans Retreat w/ Wraparound Deck, 1 mi to Nauset

Distance to beach: 1.1 mi to Nauset Beach
OWNER SPECIAL:

Just Listed **Special Winter Rates** Ideal Location Close to Nauset Beach.

Off Season:

$2,100 - $2,300/wk

$3,000 - $6,600/mo

7
Sunny Cottage near Nauset Beach
East Orleans
ID 5335
  • 3 BR
  • 1 bath
  • Sleeps 6

Sunny Cottage near Nauset Beach

Distance to beach: 1.5 miles to Nauset Beach and 3.6 miles to Skaket Beach
5.02 reviews

Off Season:

$2,200 - $2,300/wk

4
Pleasant Bay Hideaway - Charming 1870s Home, Private Beach
East Orleans
ID 13424
  • 3 BR
  • 1 bath
  • Sleeps 6

Pleasant Bay Hideaway - Charming 1870s Home, Private Beach

Distance to beach: 1/2 mile walk/drive to private Pleasant Bay beach
5.034 reviews

Summer:

$2,570/wk

Off Season:

$250 - $300/night

$1,970 - $2,570/wk

2
Skaket Beach Getaway - Sea Breeze
Orleans
ID 35278
  • 3 BR
  • 1 bath
  • Sleeps 6

Skaket Beach Getaway - Sea Breeze

Distance to beach: 2/10 mi to Skaket Beach
4.52 reviews

Off Season:

$472/night

$3,300/wk

3
Expansive Nauset Views with Beach Access
Orleans
ID 39908
  • 3 BR
  • 1 bath
  • Sleeps 6

Expansive Nauset Views with Beach Access

Distance to beach: Short walk (2/10 mile) to Nauset Beach and Direct Access to Priscilla Landing
5.03 reviews

Off Season:

$7,300 - $8,300/wk

5
Coastal Chic privacy East Orleans in Ideal Location
East Orleans
ID 36880
  • 3 BR
  • 2 baths
  • Sleeps 6

Coastal Chic privacy East Orleans in Ideal Location

Distance to beach: 1.5 mi to Nauset Beach and 2.5 mi to Skaket Beach
5.02 reviews

Summer:

$2,800 - $4,165/wk

Off Season:

$2,100 - $3,850/wk

$10,000 - $12,000/mo

6
Lakefront Retreat w/ Deck, Dock, Sandy Beach, 5 watercraft
Orleans
ID 36890
  • 2 BR
  • 1 bath
  • Sleeps 6

Lakefront Retreat w/ Deck, Dock, Sandy Beach, 5 watercraft

Distance to beach: 2.9 mi Nauset Beach and On Crystal Lake
5.029 reviews

Summer:

$4,040/wk

Off Season:

$157 - $577/night

$1,100 - $4,040/wk

9
Nauset Breeze - pet friendly
Orleans
ID 40843
  • 2 BR
  • 1 bath
  • Sleeps 6

Nauset Breeze - pet friendly

Distance to beach: 4.2 mi to Skaket Beach and 2.5 mi to Nauset Beach
5.08 reviews

Summer:

$3,400/wk

Off Season:

$400/night

$2,800 - $3,400/wk

8
Walk to Bakers Pond!
Orleans
ID 42220
  • 2 BR
  • 2 baths
  • Sleeps 6

Walk to Bakers Pond!

Distance to beach: 1.3 mi to Cliff Pond

Summer:

$2,000/wk

Off Season:

$1,800/wk

East Orleans Old Cape Vacation Cottage
East Orleans, Barley Neck Rd o
ID 9996
  • 2 BR
  • 1 bath
  • Sleeps 6

East Orleans Old Cape Vacation Cottage

Distance to beach: 2.5 miles Nauset Beach

Summer:

$3,180/wk

$10,000/mo

Off Season:

$360 - $400/night

$2,580 - $3,180/wk

$9,600 - $12,000/mo

Orleans vacation rentals that sleep 5

Easy Living in East Orleans for 2026
Orleans
ID 25978
  • 2 BR
  • 2 baths
  • Sleeps 5

Easy Living in East Orleans for 2026

Distance to beach: 2.5 miles Nauset Beach and 2.5 miles Skaket Beach
4.946 reviews

Summer:

$2,180 - $2,630/wk

Off Season:

$215 - $235/night

$1,580 - $2,180/wk

6
Welcome to our Orleans Escape!
Orleans
ID 31244
  • 2 BR
  • 1 bath
  • Sleeps 5

Welcome to our Orleans Escape!

Distance to beach: 2 miles Nauset Beach and 2 miles Skaket Beach
5.022 reviews

Summer:

$1,900 - $1,950/wk

Off Season:

$1,500 - $1,900/wk

2
The perfect getaway: Newer, pristine, and near Nauset!
Orleans
ID 35270
  • 2 BR
  • 1 bath
  • Sleeps 5

The perfect getaway: Newer, pristine, and near Nauset!

Distance to beach: 1.0 mi to Nauset Beach and 2.0 mi to Skaket Beach
5.08 reviews

Summer:

$2,200 - $2,800/wk

Off Season:

$2,100 - $2,400/wk

$3,200/mo

7

Orleans vacation rentals that sleep 4

Cute Cape Cottage
East Orleans
ID 28618
  • 2 BR
  • 1 bath
  • Sleeps 4

Cute Cape Cottage

Distance to beach: 2 miles Nauset Beach and 5 min walk to Meeting House Pond
5.09 reviews

Summer:

$1,700 - $1,999/wk

Off Season:

$210 - $320/night

$1,000 - $1,600/wk

$2,100 - $2,700/mo

4
Ellerslie Cottage/Walk to Private Association Beach
Orleans
ID 38958
  • 2 BR
  • 1 bath
  • Sleeps 4

Ellerslie Cottage/Walk to Private Association Beach

Distance to beach: 1/2 mi to East Egg Association Beach
5.09 reviews

Summer:

$1,910/wk

$7,000/mo

Off Season:

$250/night

$1,710/wk

$3,500 - $6,000/mo

2
Topside Boathouse - Swim and Fish off the Deck !
Pleasant Bay South Orleans
ID 25897
  • 2 BR
  • 1 bath
  • Sleeps 4

Topside Boathouse - Swim and Fish off the Deck !

Distance to beach: Swim off the deck or walk 1/8 mile to town beach.
5.035 reviews

Off Season:

$400/night

$1,800 - $3,000/wk

4
Charming Eco-Friendly Cape Cod Cottage
Orleans
ID 35207
  • 1 BR
  • 1 bath
  • Sleeps 4

Charming Eco-Friendly Cape Cod Cottage

Distance to beach: 0.7 mi to Crystal Lake
5.05 reviews
OWNER SPECIAL:

Next winter rental still available!!

Summer:

$10,500/wk

Off Season:

$10,000 - $10,500/wk

8

Orleans vacation rentals that sleep 2

Newly Built Guesthouse with Private Association Beach
South Orleans
ID 20417
  • 1 BR
  • 1 bath
  • Sleeps 2

Newly Built Guesthouse with Private Association Beach

Distance to beach: 1/10 mile to Private Assoc.Beach on Pleasant Bay
5.0220 reviews

Off Season:

$225 - $400/night

$1,300 - $1,700/wk

5
Adorable Updated Cottage, walk to Nauset beach
East Orleans
ID 25650
  • 1 BR
  • 1 bath
  • Sleeps 2

Adorable Updated Cottage, walk to Nauset beach

Distance to beach: 1/3 mile from Nauset Beach
4.919 reviews

Summer:

$1,735/wk

Off Season:

$185/night

$1,235 - $1,735/wk

4
Fabulous Getaway....Relax and Unwind....
East Orleans
ID 34810
  • 1 BR
  • 1 bath
  • Sleeps 2

Fabulous Getaway....Relax and Unwind....

Distance to beach: 1.6 mi to Nauset Beach
5.05 reviews

Summer:

$2,700/wk

Off Season:

$2,200 - $2,700/wk

2
Captain Seth Sparrow Cottage/Salt Water Access/Kayaks
South Orleans
ID 40290
  • 1 BR
  • 1 bath
  • Sleeps 2

Captain Seth Sparrow Cottage/Salt Water Access/Kayaks

Distance to beach: 1.0 mi to Crystal Lake and 350yd walk on deeded path to Arey's Pond for kayak

Summer:

$2,625/wk

Off Season:

$1,825 - $2,225/wk

3
Waterfront Modern Air Conditioned Cottage on Pleasant Bay
Orleans
ID 29120
  • 1 BR
  • 1 bath
  • Sleeps 2

Waterfront Modern Air Conditioned Cottage on Pleasant Bay

Distance to beach: 4 miles to Nauset; 3 miles to Skaket
5.052 reviews

Off Season:

$1,400/wk

6