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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.

13 Vacation Properties in Osterville
sleeping

Osterville vacation rentals that sleep 10

Osterville
ID 28467
4 BR
4 baths
Sleeps 10
Luxury Home with Central AC & Pool
Distance to beach: 1+ mile to Dowses Beach
Description
New weekly summer rental listing! This elegant home boasts great entertaining space inside & out! The 1st floor features a lovely eat-in kitchen, formal dining, sunroom, a large family room, den, and ... read more
Key amenities
deck/porch/patio, pool, central A/C, washer&dryer, dishwasher, linens included, cable TV, wireless or wired internet
Time active on this website
2 months
Property ID 28467 listed by: Amanda, Realtor
Summer:
$600 - $800/night
$4,500 - $6,000/wk
$23,000 - $24,000/mo
Off Season:
$400 - $800/night
$4,500 - $6,000/wk
$13,000 - $23,000/mo

Osterville vacation rentals that sleep 9

Osterville
ID 27473
4 BR
2 baths
Sleeps 9
Recently renovated home, steps to Osterville Village!
Distance to beach: 1 mile to Dowses Beach - beach sticker included
2 reviews read reviews
Description
This beautiful home is located within walking distance of Osterville Village and Joshua's Pond for fresh water swimming and kayaking and is a mile to the spectacular Dowses ocean beach. Relax at the ... read more
Key amenities
deck/porch/patio, outdoor shower, central A/C, washer&dryer, dishwasher, linens included, cable TV, DVD or VCR, fireplace, wireless or wired internet, handicap accessibility
Time active on this website
6 months
Property ID 27473 listed by: Ralph
Summer:
$2,800/wk
$9,500/mo
Off Season:
$1,800 - $2,700/wk
$5,000 - $7,800/mo
Osterville
ID 28557
4 BR
3 baths
Sleeps 9
Osterville Waterfront with Spectacular Views
Distance to beach: Dowses Beach 1.5 miles
Description
Spend your next vacation at this beautiful waterfront property located on spectacular West Bay in Osterville. Enjoy the views from the expansive deck or stroll your own stretch of pristine shoreline. ... read more
Key amenities
on salt water, deck/porch/patio, outdoor shower, central A/C, washer&dryer, dishwasher, linens included, cable TV, wireless or wired internet, pet-friendly
Time active on this website
1 month
Property ID 28557 listed by: Ellen Valentgas, Sotheby's International Realty
Summer:
$7,500 - $10,000/wk
Off Season:
$4,900 - $10,000/wk

Osterville vacation rentals that sleep 8

Osterville
ID 11042
4 BR
2 ½ baths
Sleeps 8
Beautiful & Spacious Cape Cod Home
Distance to beach: approx. 1 mile to Dowses Beach
1 review read review
Description
This charming home sits on top of hill on Historic Main Street in the village of Osterville. This newly renovated home features 4 bedrooms, 2.5 bathrooms, a kitchen any chef would enjoy, and a large f... read more
Key amenities
screened porch, deck/porch/patio, central A/C, washer&dryer, dishwasher, linens included, cable TV, DVD or VCR, fireplace, wireless or wired internet
Time active on this website
10 years, 10 months
Property ID 11042 listed by: Peter or Shannon
Summer:
$2,700/wk
Off Season:
$1,100 - $2,700/wk
Osterville
ID 14924
4 BR
2 ½ baths
Sleeps 8
Charming, Fully-Appointed 4 Bedroom Home, Minutes from Beach
Distance to beach: 2 miles to Dowses Beach- beach sticker included
5 reviews read reviews
Description
This family friendly Cape Cod home is a perfect spot for your vacation! The home is spacious, and offers four bedrooms perfectly configured for privacy and comfort, with spacious back yard and outside... read more
Key amenities
deck/porch/patio, outdoor shower, washer&dryer, dishwasher, linens included, cable TV, DVD or VCR, fireplace, wireless or wired internet, pet-friendly, handicap accessibility
Time active on this website
2 years, 8 months
Property ID 14924 listed by: Sharon
Summer:
$500/night
$3,000/wk
Off Season:
$500/night
$3,000/wk
Osterville
ID 23877
4 BR
3 baths
Sleeps 8
Immaculate vacation home - Quiet Osterville neighborhood
Distance to beach: 2 mi to Dowses Beach and Craigville Beach
5 reviews read reviews
Description
Enjoy this clean, well maintained vacation home 2 miles from Dowses and Craigville beaches in a quiet residential neighborhood south of route 28, great for walks and bike rides. The 4 bedrooms sleep 9... read more
Key amenities
deck/porch/patio, outdoor shower, A/C unit(s), washer&dryer, dishwasher, linens included, cable TV, DVD or VCR, fireplace, wireless or wired internet
Time active on this website
1 year, 11 months
Property ID 23877 listed by: Rob
Summer:
$2,100 - $2,300/wk
Off Season:
$1,000 - $2,100/wk
Osterville
ID 27235
4 BR
2 baths
Sleeps 8
Great home for multi-families! Central AC, Near Dowses Beach
Distance to beach: 1 mile to Dowses Beach
Description
Location! Location! Location! Conveniently located in prestigious Oyster Hills, this picturesque 4 bedroom, 2 full bath, completely renovated home is waiting for you to enjoy the vacation of a lifetim... read more
Key amenities
deck/porch/patio, outdoor shower, central A/C, washer&dryer, dishwasher, linens included, cable TV, DVD or VCR, fireplace, wireless or wired internet
Time active on this website
7 months
Property ID 27235 listed by: Charlene Flynn
Summer:
$2,800 - $3,300/wk
Off Season:
$400 - $500/night
$2,500 - $2,800/wk
Osterville
ID 5286
3 BR
2 baths
Sleeps 8
Osterville Escape
Distance to beach: 4/10 mile to ponds, less than 2 miles to Dowses
1 review read review
Description
Relax in comfort in this welcoming, clean, open Cape home in Osterville. This attractive home is located in a quiet neighborhood within walking distance to several ponds and the village center, and a ... read more
Key amenities
walk to a fresh water beach, deck/porch/patio, outdoor shower, central A/C, washer&dryer, dishwasher, linens included, cable TV, DVD or VCR, wireless or wired internet
Time active on this website
13 years
Property ID 5286 listed by: Steve Webb
Summer:
$1,800/wk
Off Season:
$1,500 - $1,800/wk
Osterville
ID 28403
3 BR
1 ½ bath
Sleeps 8
Osterville 3BR, Barnstable Beach pass included WR#134586
Distance to beach: over 1 mile to Dowses Beach
Description
Newly remodeled Open Concept three bedroom, 1.5 bath ranch with central A/C and a beautifully appointed new kitchen that includes a large breakfast bar, dining area with slider to sundeck, and a spaci... read more
Key amenities
deck/porch/patio, outdoor shower, central A/C, washer&dryer, dishwasher, cable TV, DVD or VCR, wireless or wired internet
Time active on this website
2 months
Property ID 28403 listed by: William Raveis The Rental Company
Summer:
$1,495/wk
Off Season:
$1,300 - $1,395/wk

Osterville vacation rentals that sleep 7

Osterville
ID 19650
3 BR
2 baths
Sleeps 7
Spacious Family Getaway Home
Distance to beach: 2 miles Dowses Beach
6 reviews read reviews
Description
Comfortable Family Home in a quiet Osterville neighborhood.Great for your Cape Cod summer vacation.Tastefully updated,offering a fully applianced large kitchen and dining table that will easily sit 8,... read more
Key amenities
deck/porch/patio, outdoor shower, A/C unit(s), washer&dryer, dishwasher, linens included, cable TV, DVD or VCR, fireplace, wireless or wired internet
Time active on this website
4 years, 3 months
Property ID 19650 listed by: Joanne C
Summer:
$250/night
$1,700 - $1,750/wk

Osterville vacation rentals that sleep 6

Osterville
ID 19974
3 BR
2 ½ baths
Sleeps 6
Walk to Quaint Osterville Village!
Distance to beach: 1/2 mile to Dowse's Beach
3 reviews read reviews
Description
Just turn the key and have a great vacation! This charming, fully furnished, remodeled Farmhouse-style cottage is located in the sought-after Wianno area of Osterville. The beautifully appointed hom... read more
Key amenities
walk to a salt water beach, deck/porch/patio, outdoor shower, jacuzzi, central A/C, washer&dryer, dishwasher, linens included, cable TV, DVD or VCR, fireplace, wireless or wired internet, pet-friendly, handicap accessibility
Time active on this website
6 years
Property ID 19974 listed by: Jaynie
Summer:
$2,700/wk
$10,000 - $110,000/mo
Off Season:
$2,600 - $2,700/wk
Osterville
ID 23962
3 BR
2 ½ baths
Sleeps 6
Spacious home -- immaculate and newly renovated.
Distance to beach: 1.5 miles to Dowses beach 15 min walk to pond
8 reviews read reviews
Description
This beautiful home is located in a quiet neighborhood close to town, beaches, and ponds for kayaking, hiking and swimming, and only two miles to spectacular ocean beaches. The sunroom leads to a larg... read more
Key amenities
screened porch, deck/porch/patio, A/C unit(s), washer&dryer, dishwasher, linens included, cable TV, DVD or VCR, fireplace, wireless or wired internet, handicap accessibility
Time active on this website
3 years, 4 months
Property ID 23962 listed by: Barbara
Summer:
$2,200 - $2,300/wk
Off Season:
$2,000/wk
$2,200 - $2,500/mo

Osterville vacation rentals that sleep 4

Osterville
ID 27939
2 BR
2 ½ baths
Sleeps 4
Brand new home w/AC for rent. One month or longer.
Distance to beach: Less than a mile to Dowes Beach
Description
This brand new home is stunning! Just built with luxury touches and all on one level. Large open floor plan with comfortable living room that opens to the gourmet kitchen, dining area and half bath. K... read more
Key amenities
deck/porch/patio, outdoor shower, central A/C, washer&dryer, dishwasher, linens included, cable TV, wireless or wired internet
Time active on this website
1 month
Property ID 27939 listed by: Michelle Sylvia/Realtor
Summer:
$4,000/wk
Off Season:
$4,000/wk