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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.

10 Vacation Properties in Osterville
sleeping

Osterville vacation rentals that sleep 8

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
OWNER SPECIAL:
New Year's Special Getaway! Champagne & roses provided for a memorable occasion!
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
Less than a month
Property ID 27235 listed by: Charlene Flynn
Summer:
$2,800 - $3,300/wk
Off Season:
$400 - $500/night
$1,250 - $2,800/wk
Osterville
ID 25885
4 BR
5 ½ baths
Sleeps 8
Stunning & Spacious Luxury Home with HEATED POOL!
Distance to beach: Approximately 2 miles to Dowses Beach
Description
AMAZING OPPORTUNITY - NEW LISTING. Stunning Osterville Cape perfect for entertaining. This newly renovated home is sited on a large private lot with a heated pool, fire pit, and gorgeous Travertine p... read more
Key amenities
deck/porch/patio, pool, outdoor shower, central A/C, washer&dryer, dishwasher, linens included, cable TV, wireless or wired internet
Time active on this website
10 months
Property ID 25885 listed by: Amanda, Realtor
Summer:
$6,800/wk
$25,000 - $27,000/mo
Off Season:
$5,000 - $6,800/wk
$5,000 - $27,000/mo
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
12 years, 4 months
Property ID 5286 listed by: Steve Webb
Off Season:
$200 - $250/night
$1,500 - $1,750/wk
Osterville
ID 14827
3 BR
2 baths
Sleeps 8
Osterville - ''Like New'' Light, Bright & Open 3B/2B Ranch
Distance to beach: Dowses Beach - Under 2 Miles - 5 Minute Drive
7 reviews read reviews
Description
Welcome to the Cape! This Southside, fully renovated, One Level Home is Open & Airy with Vaulted Skylit Ceilings, Hardwood Floors, Bright Kitchen w/Stainless Appliances, Center Eat-Up Island & Dishwas... read more
Key amenities
deck/porch/patio, A/C unit(s), washer&dryer, dishwasher, linens included, cable TV, fireplace, wireless or wired internet, handicap accessibility
Time active on this website
6 years, 6 months
Property ID 14827 listed by: Alynn Berry, Realtor
Off Season:
$1,100 - $1,200/wk

Osterville vacation rentals that sleep 6

Osterville
ID 16112
3 BR
2 baths
Sleeps 6
Clean & Bright, walk to town, Osterville Vacation Home!
Distance to beach: 1 mile to Osterville's Dowses Beach
3 reviews read reviews
Description
Located in the convenient and sought-after neighborhood of Oyster Hills, this ranch style home has all the essentials! Professionally decorated & fully furnished in upscale comfort, this sunny home of... 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
7 years, 1 month
Property ID 16112 listed by: Lisa
Summer:
$2,500 - $2,800/wk
Off Season:
$2,000 - $2,500/wk
$2,300 - $2,500/mo
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
2 years, 8 months
Property ID 23962 listed by: Barbara
Summer:
$2,200 - $2,300/wk
Off Season:
$2,000/wk
$2,200 - $2,500/mo
Osterville
ID 26160
3 BR
1 bath
Sleeps 6
Quaint Osterville Village Cape Cod Cottage
Distance to beach: Under 1/2 mi to Joshua's Pond,1 mi to Dowses
4 reviews read reviews
Description
This quaint Cape Cod Cottage on Tower Hill Road in Osterville Village is in a quiet, family oriented neighborhood. Just a short 10 min walk to Osterville Village Main Street for shopping or ice cream ... read more
Key amenities
walk to a fresh water beach, deck/porch/patio, A/C unit(s), washer&dryer, linens included, cable TV, DVD or VCR, wireless or wired internet
Time active on this website
8 months
Property ID 26160 listed by: Daryll Brose
Summer:
$1,195/wk
Off Season:
$1,195/wk
Osterville
ID 11421
3 BR
2 baths
Sleeps 6
Deceivingly Roomy, Remodeled, Convenient to town & beach . .
Distance to beach: Dowses Beach (1 mi.) Joshua's Pond (1 mi.)
6 reviews read reviews
Description
This spacious, recently renovated and tastefully decorated Cape ranch, in a quiet neighborhood, is a short walk to charming Osterville village, and a mile from the warmish waters at Dowses Beach or th... read more
Key amenities
deck/porch/patio, outdoor shower, A/C unit(s), washer&dryer, dishwasher, linens included, cable TV, DVD or VCR, wireless or wired internet, handicap accessibility
Time active on this website
10 years, 9 months
Property ID 11421 listed by: Mary Jaros
Summer:
$2,000 - $2,100/wk
Off Season:
$2,000/wk
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
5 years, 4 months
Property ID 19974 listed by: Jaynie
Summer:
$2,700/wk
$10,000/mo
Off Season:
$2,600 - $2,700/wk
$10,000/mo

Osterville vacation rentals that sleep 5

Osterville
ID 24515
3 BR
1 bath
Sleeps 5
Osterville in the Heart of Wianno, Nantucket Style Cottage
Distance to beach: Dowses Beach 0.83 mile
3 reviews read reviews
Description
Charming Nantucket style cottage tucked away down a private lane but right in the heart of Wianno, the most prestigious section of Osterville. Just a stroll to the Village and Beach make this seasi... read more
Key amenities
deck/porch/patio, outdoor shower, central A/C, washer&dryer, linens included, cable TV, DVD or VCR, wireless or wired internet, handicap accessibility
Time active on this website
1 year, 1 month
Property ID 24515 listed by: Ginny at Oyster RE
Summer:
$2,500/wk
Off Season:
$1,800 - $2,500/wk