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Mid Cape Cod Vacation Rentals

Osterville Vacation Rentals

Osterville is an exclusive seaside community on Nantucket Sound. Elegant waterfront homes, many of which were built in the 19th century, line the main streets.

Osterville Travel Guide

33 Vacation Properties in Osterville

Sleeps

Osterville vacation rentals that sleep 14

Osterville

ID 37315

7 BR

5 ½ baths

Sleeps 14

Impressive Osterville Residence - w/Guest House

Distance to beach:

Summer:
$17,000/wk

Off Season:
$9,500 - $17,000/wk

Osterville vacation rentals that sleep 12

Osterville

ID 38649

6 BR

8 baths

Sleeps 12

*New 2024* Osterville Seaside Estate

Distance to beach:

Summer:
$26,297/wk

Osterville

ID 36579

5 BR

4 ½ baths

Sleeps 12

Wianno Ave Home With Pool

Distance to beach: 0.6 mi to Dowses and Sea View Beach

Summer:
$27,000/wk

Off Season:
$18,000 - $27,000/wk

Osterville vacation rentals that sleep 10

Osterville

ID 33824

5 BR

2 ½ baths

Sleeps 10

5 Bedroom home w/Central AC one mile to Dowses Beach

Distance to beach: 1.2 mi to Dowses

Summer:
$4,500/wk

Off Season:
$4,500/wk

Osterville

ID 35972

4 BR

2 ½ baths

Sleeps 10

Osterville Retreat- minutes to Village and beach!

Distance to beach: 2.4 mi to Dowses

7 reviews read reviews

Summer:
$4,950/wk

Off Season:
$350 - $450/night
$3,000 - $4,950/wk
$3,000 - $4,000/mo

Osterville

ID 37082

4 BR

3 ½ baths

Sleeps 10

Newly renovated home all ready for Christmas

Distance to beach: 1/2 mi to Joshua Pond and 2 mi to Dowses

4 reviews read reviews

OWNER SPECIAL:

Seasons by the Sea is ready for all the Seasons!

Summer:
$7,500/wk

Off Season:
$7,500/wk

Osterville

ID 37723

4 BR

3 ½ baths

Sleeps 10

Spacious Osterville Retreat/Hot Tub/Beach Pass Provided

Distance to beach: 1.4 mi to Dowses

Summer:
$700 - $850/night
$5,075 - $6,099/wk

Off Season:
$700 - $850/night
$5,075/wk

Osterville

ID 37549

4 BR

2 baths

Sleeps 10

Spacious Home, Quiet Neighborhood, Great for Families

Distance to beach: .8 miles Joshua Pond and 2.1 mi to Dowses

12 reviews read reviews

Summer:
$3,000/wk

Off Season:
$200 - $450/night
$2,000 - $3,000/wk
$3,500 - $5,000/mo

Osterville

ID 38533

4 BR

3 ½ baths

Sleeps 10

ID# 156358 Walk to Osterville Center in this Stunning Home

Distance to beach: 2.2 mi to Dowses

Summer:
$6,500/wk

Off Season:
$929/night
$6,500/wk

Osterville

ID 37314

4 BR

4 ½ baths

Sleeps 10

Sea View Ave - New Construction - Pool Hot Tub Tennis Court

Distance to beach: 0.25 mi to Dowses

Summer:
$35,000/wk

Off Season:
$22,000 - $35,000/wk

Osterville vacation rentals that sleep 9

Osterville

ID 38500

4 BR

3 ½ baths

Sleeps 9

Osterville Home Walking Distance to French Bakery

Distance to beach: .7 mi to Joshua Pond and 2.9 Craigville Beach

Summer:
$4,000 - $6,500/wk

Off Season:
$500 - $600/night
$2,000 - $5,500/wk

Osterville

ID 38820

4 BR

3 ½ baths

Sleeps 9

032-Ov Updated with Pool in Charming Osterville Village

Distance to beach: 1.9 mi to Dowses

OWNER SPECIAL:

Rates shown reflect a rate reduction of 10%!

Summer:
$6,890 - $7,650/wk

Off Season:
$551 - $980/night
$3,440 - $6,120/wk

Osterville - Barnstable

ID 36837

3 BR

2 baths

Sleeps 9

Cape Escape - Minutes to Beaches w Barnstable Beach Pass

Distance to beach: 1/2 mile Joshua Pond and 2 miles Dowses

4 reviews read reviews

Summer:
$2,500 - $3,200/wk
$12,000 - $14,000/mo

Off Season:
$300 - $350/night
$1,500 - $2,500/wk
$5,000 - $9,000/mo

Osterville vacation rentals that sleep 8

Osterville

ID 27473

4 BR

2 baths

Sleeps 8

Close to Osterville Village!

Distance to beach: 1 mile to Dowses Beach - beach sticker included

24 reviews read reviews

Summer:
$4,000 - $4,200/wk

Off Season:
$350 - $575/night
$2,500 - $4,200/wk

Osterville

ID 36027

4 BR

2 baths

Sleeps 8

New Rates, Near Joshua Pond, Dogs OK, Central A/C, Sunroom

Distance to beach: 3/10 mi to Joshua Pond

Summer:
$3,360/wk

Off Season:
$260 - $280/night
$2,870 - $3,150/wk

Osterville

ID 34432

3 BR

2 baths

Sleeps 8

Updated 3 Bedroom with AC & Great Proximity to Summer Fun

Distance to beach: 1.2 mi to Dowses and 3.5 mi Craigville Beach

4 reviews read reviews

Summer:
$2,100 - $2,500/wk

Off Season:
$2,500/wk

Osterville

ID 35895

3 BR

2 ½ baths

Sleeps 8

Osterville- New renovation, central AC, beach pass included

Distance to beach: 3/10 mi to Joshua Pond

12 reviews read reviews

Summer:
$2,450 - $4,600/wk

Off Season:
$300 - $500/night
$2,100 - $2,700/wk
$4,000 - $6,500/mo

Osterville

ID 36324

3 BR

2 ½ baths

Sleeps 8

Osterville Village Beauty on 6 Acres of Privacy

Distance to beach: 1 mi to Joshua Pond and 1 mi to Dowses

Summer:
$500 - $750/night
$4,000 - $5,000/wk

Off Season:
$250 - $750/night
$1,750 - $4,000/wk

Osterville

ID 37412

3 BR

2 baths

Sleeps 8

Pristine Family Vacation Home/Beach Pass Included

Distance to beach: 1.8 mi to Joshua Pond and 3.2 Dowses

4 reviews read reviews

Summer:
$2,600 - $3,200/wk

Off Season:
$300 - $385/night
$2,200 - $2,500/wk
$8,500 - $10,000/mo

Osterville

ID 37316

3 BR

1 ½ bath

Sleeps 8

Osterville Village - Large Yard & Outdoor Patio

Distance to beach: 1 mile to Dowses

Summer:
$7,000/wk

Off Season:
$300 - $600/night
$3,500 - $7,000/wk

Osterville vacation rentals that sleep 7

Osterville

ID 18377

3 BR

1 ½ bath

Sleeps 7

Roomy Osterville Favorite with Private Gated Yard

Distance to beach: .7 Dowses and 2.3 Craigville Beach

Summer:
$2,395 - $2,695/wk

Off Season:
$300 - $325/night
$1,800 - $2,695/wk

Osterville

ID 23526

3 BR

2 baths

Sleeps 7

Delightful Osterville Haven. Walk to Main St. and a Swim!

Distance to beach: 3/10 mile to Joshua Pond and 1 mile to Dowses

31 reviews read reviews

Summer:
$2,650 - $3,300/wk

Off Season:
$1,750 - $2,620/wk

Osterville vacation rentals that sleep 6

Osterville

ID 38694

4 BR

3 ½ baths

Sleeps 6

Close to Beautiful Dowses Beach, Central AC, & Pet Friendly

Distance to beach: 0.9 mi to Dowses

Summer:
$6,300/wk

Off Season:
$500/night
$3,500 - $6,300/wk

Osterville Woods

ID 35272

3 BR

3 baths

Sleeps 6

Osterville Great Family Rental!

Distance to beach: 1.5 Joshua Pond and 3.0 Dowses

Summer:
$2,500 - $3,200/wk

Off Season:
$225 - $350/night
$1,800 - $2,500/wk
$3,000/mo

Osterville

ID 36955

3 BR

2 baths

Sleeps 6

Spacious Home/Walk to Town/Beach Pass & Kayaks Included

Distance to beach: 1.0 mi to Dowses and 1.0 mi to Craigville Beach

Summer:
$5,000 - $6,000/wk

Off Season:
$4,000 - $5,000/wk

Carriage House

ID 38342

3 BR

2 baths

Sleeps 6

Carriage House - Oceanfront - Overlooking Dowses Beach

Distance to beach: 5/10 to dowses Dowses and private beach off wooden walkway on the property

Summer:
$7,500/wk
$30,000 - $37,500/mo

Off Season:
$7,500/wk

Osterville

ID 38319

3 BR

2 baths

Sleeps 6

Dog Friendly Charmer - Convenient Location

Distance to beach: 1.6 miles Joshua Pond and 3.0 miles Dowses

Summer:
$2,000 - $2,100/wk

Off Season:
$175 - $215/night
$1,000 - $2,000/wk
$2,100 - $2,200/mo

Osterville

ID 38786

3 BR

2 baths

Sleeps 6

Centrally Located Family Retreat/Beach Pass Included

Distance to beach: 1.6 mi to Joshua Pond and 1.5 mi Dowses

Summer:
$3,500 - $5,600/wk

Off Season:
$350 - $650/night
$2,450 - $4,550/wk

Osterville

ID 32374

3 BR

2 ½ baths

Sleeps 6

Beautiful & Pristine Osterville Cape, walk to Village

Distance to beach: 1 3/10 miles to Craigville Beach and 1 6/10 miles to Dowses

Summer:
$4,000/wk

Off Season:
$3,500 - $4,000/wk

Osterville

ID 37313

2 BR

2 baths

Sleeps 6

Osterville Oasis

Distance to beach: 2.6 mi to Craigville Beach

Summer:
$4,025 - $4,375/wk

Off Season:
$315/night
$2,450 - $3,150/wk

Osterville vacation rentals that sleep 5

Osterville

ID 37279

3 BR

1 ½ bath

Sleeps 5

Osterville Cape Cod- 3BR & Pet Friendly

Distance to beach: 3.5 miles to Craigville Beach

Summer:
$2,093/wk

Off Season:
$230 - $255/night
$1,610 - $1,900/wk

Osterville vacation rentals that sleep 4

Osterville

ID 34848

2 BR

1 ½ bath

Sleeps 4

Enchanting Cottage - one block to Osterville Village!

Distance to beach: 0.5 mi to Joshua Pond and 1.5 mi to Dowses

5 reviews read reviews

Summer:
$2,500 - $2,950/wk

Off Season:
$2,000 - $2,950/wk
$2,500 - $3,000/mo

Osterville vacation rentals that sleep 3

Osterville

ID 37628

3 BR

3 ½ baths

Sleeps 3

Charming Osterville Home w/ Pool - Near Town

Distance to beach: 600 ft to Joshua Pond and 1.5 mi to Dowses

Summer:
$12,250/wk

Off Season:
$650 - $850/night
$6,000 - $12,250/wk