Search Vacation Homes in Osterville

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Check prices for these dates

Next weekend
16 May - 18 May
In two weeks
23 May - 25 May
In one month
6 Jun - 8 Jun
In two months
4 Jul - 6 Jul

Compare 2949 Vacation Homes in Osterville with updated reviews, rates, and availability.

Plymouth private ocean front oversized suite on the bluff of Cape Cod Bay
Beach nearby

Plymouth private ocean front oversized suite on the bluff of Cape Cod Bay

10.0 out of 10, Exceptional, (96)
"Wonderful stay at this beautiful property! Great location and everything from the check in to the views were perfect!"
The price is AED 918
AED 1,399 total
includes taxes & fees
15 May - 16 May
Plymouth private ocean front oversized suite on the bluff of Cape Cod Bay
WATERFRONT w/Kayaks & SUP’s ★ Pet friendly ★ HOT TUB★Firepit & FPL★Deck & Patio
Outdoor spa tub

WATERFRONT w/Kayaks & SUP’s ★ Pet friendly ★ HOT TUB★Firepit & FPL★Deck & Patio

10.0 out of 10, Exceptional, (86)
"Wonderful property!"
The price is AED 1,028
AED 2,497 total
includes taxes & fees
22 May - 23 May
WATERFRONT w/Kayaks & SUP’s ★ Pet friendly ★ HOT TUB★Firepit & FPL★Deck & Patio
Cape Cod cottage
Exterior

Cape Cod cottage

9.6 out of 10, Exceptional, (101)
"House was very clean. Nicely decorated. Peaceful. Has everything you may need. Check in and check out was smooth. I even walked in to a nice little surprise. Highly recommend."
Cape Cod cottage
Coastal chic meets French Provençal in this newly renovated oceanfront home.
5 bedrooms, desk, iron/ironing board, travel crib

Coastal chic meets French Provençal in this newly renovated oceanfront home.

10.0 out of 10, Exceptional, (79)
"Great stay! "
The price is AED 1,928
AED 4,418 total
includes taxes & fees
4 Jun - 5 Jun
Coastal chic meets French Provençal in this newly renovated oceanfront home.
OCEANFRONT, PRIVATE BEACH AND DECK, AMAZING VIEWS, KAYAKS, 2 Story House, 4+BR
Exterior

OCEANFRONT, PRIVATE BEACH AND DECK, AMAZING VIEWS, KAYAKS, 2 Story House, 4+BR

10.0 out of 10, Exceptional, (103)
"Fantastic location, right on the beach and convenient to restaurants and shops."
OCEANFRONT, PRIVATE BEACH AND DECK, AMAZING VIEWS, KAYAKS, 2 Story House, 4+BR
2 Bedroom, 2 Bath, 1100 sqft, sun porch, eat in kitchen, Washer/Dryer, Gas Grill
Miscellaneous

2 Bedroom, 2 Bath, 1100 sqft, sun porch, eat in kitchen, Washer/Dryer, Gas Grill

10.0 out of 10, Exceptional, (150)
"Perfect for our stay, comfortable beds, well stocked kitchen very clean, easy to communicate with owner, nice that it is pet friendly"
The price is AED 331
AED 1,156 total
includes taxes & fees
11 May - 12 May
2 Bedroom, 2 Bath, 1100 sqft, sun porch, eat in kitchen, Washer/Dryer, Gas Grill
Charming cottage with deck, yard, & AC - walk to beach, Main Street, & ferry
Fridge, microwave, oven, stovetop

Charming cottage with deck, yard, & AC - walk to beach, Main Street, & ferry

9.6 out of 10, Exceptional, (49)
"This was a lovely home in a very nice location"
Charming cottage with deck, yard, & AC - walk to beach, Main Street, & ferry
Historic Oak Bluffs home, short walk to town, beach, and harbor.
Terrace/patio

Historic Oak Bluffs home, short walk to town, beach, and harbor.

9.6 out of 10, Exceptional, (28)
"We enjoy it all. "
Historic Oak Bluffs home, short walk to town, beach, and harbor.
6 Richards Way - New Listing! East Sandwich Home with Hot Tub & Near Beach
Smart TV, fireplace, books

6 Richards Way - New Listing! East Sandwich Home with Hot Tub & Near Beach

6 Richards Way - New Listing! East Sandwich Home with Hot Tub & Near Beach
Waterfront, Incredible Views and Private Dock!
Interior

Waterfront, Incredible Views and Private Dock!

9.4 out of 10, Exceptional, (3)
"Location was great for us. Beds were very clean and comfortable and many bedrooms. Kitchen view was amazing and appliances worked well. Overall, very nice, quiet vacation home. "
Waterfront, Incredible Views and Private Dock!
Oldest Town of Cape Cod In The Historic District
Fridge, microwave, oven, stovetop

Oldest Town of Cape Cod In The Historic District

9.4 out of 10, Exceptional, (3)
"The property has a great location and was very well kept up. We were out a lot at a conference but really enjoyed the property and the owner. "
The price is AED 349
AED 1,291 total
includes taxes & fees
8 Jun - 9 Jun
Oldest Town of Cape Cod In The Historic District
Stunning Oceanfront Home With Amazing Views ~ Private Beach - capeoceanvista
Interior

Stunning Oceanfront Home With Amazing Views ~ Private Beach - capeoceanvista

9.6 out of 10, Exceptional, (109)
"Really amazing, breathtaking views, private! A great retreat for family time. "
The price is AED 2,567
AED 4,704 total
includes taxes & fees
11 May - 12 May
Stunning Oceanfront Home With Amazing Views ~ Private Beach - capeoceanvista
Gorgeous Spacious Victorian Cape Code Beach View Retreat
Beach nearby

Gorgeous Spacious Victorian Cape Code Beach View Retreat

Gorgeous Spacious Victorian Cape Code Beach View Retreat
Charming coastal home with large yard, firepit, & grill - pool and beach access
Beach

Charming coastal home with large yard, firepit, & grill - pool and beach access

9.6 out of 10, Exceptional, (15)
"Our family was so impressed with this house! Every single element was thought of- the location was perfect and it was such a lovely stay. We hope to be back!"
Charming coastal home with large yard, firepit, & grill - pool and beach access
Cozy Yarmouth Cottage
Property grounds

Cozy Yarmouth Cottage

9.6 out of 10, Exceptional, (5)
"Beautiful and comfortable space perfect for our family of four. "
Cozy Yarmouth Cottage
Close to Bike Path 1 Mile to Beaches!
Beach nearby

Close to Bike Path 1 Mile to Beaches!

9.6 out of 10, Exceptional, (16)
"Perfect little get away and quiet and private. SO close to so many attractions."
Close to Bike Path 1 Mile to Beaches!
Pond Perch: 239-B Brewster Pond Front Perfection, Walk to Private Beach
Fridge, microwave, oven, stovetop

Pond Perch: 239-B Brewster Pond Front Perfection, Walk to Private Beach

10.0 out of 10, Exceptional, (5)
"Beautiful setting"
Pond Perch: 239-B Brewster Pond Front Perfection, Walk to Private Beach
Falmouth Cape - Walk to Island Queen ferry to Martha's Vineyard, Beach, Downtown
Beach nearby, sun loungers, beach towels

Falmouth Cape - Walk to Island Queen ferry to Martha's Vineyard, Beach, Downtown

10.0 out of 10, Exceptional, (168)
"Great house and location for stay during winter hockey tournament "
Falmouth Cape - Walk to Island Queen ferry to Martha's Vineyard, Beach, Downtown
Hot Tub, 200 ft to Beach!
Outdoor dining

Hot Tub, 200 ft to Beach!

9.8 out of 10, Exceptional, (8)
"The property was beautiful and the beds were extremely comfortable. The property management was responsive and helpful."
Hot Tub, 200 ft to Beach!
Pet Friendly,Quiet family neighborhood with private fenced in yard with hot tub
Sun loungers, beach towels

Pet Friendly,Quiet family neighborhood with private fenced in yard with hot tub

10.0 out of 10, Exceptional, (147)
"Great place to stay with family and pet."
Pet Friendly,Quiet family neighborhood with private fenced in yard with hot tub
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Other property types in Osterville

Edgewater Beach Resort, a VRI resort
BBQ/picnic area

Edgewater Beach Resort, a VRI resort

3.5 star property
8.8 out of 10, Excellent, (269)
"I love staying here "
The price is AED 760
AED 870 total
includes taxes & fees
15 May - 16 May
Edgewater Beach Resort, a VRI resort
The Cove At Yarmouth
Beach nearby

The Cove At Yarmouth

3.0 star property
9.2 out of 10, Wonderful, (236)
"It is a very nice place to stay"
The price is AED 521
AED 596 total
includes taxes & fees
11 May - 12 May
The Cove At Yarmouth
The Club at New Seabury
Seasonal outdoor pool, cabanas (surcharge), pool umbrellas

The Club at New Seabury

3.5 star property
9.0 out of 10, Wonderful, (317)
"Perfect little cottage!"
The price is AED 694
AED 795 total
includes taxes & fees
11 May - 12 May
The Club at New Seabury
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.