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Compare 2950 Vacation Homes in Osterville with updated reviews, rates, and availability.

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

10.0 out of 10, Exceptional, (96)
"We had a wonderful stay- very comfortable, relaxing, and beautiful ocean view! Hosts Mike and Judy were the best, providing everything needed and more."
The price is AED 731
AED 1,161 total
includes taxes & fees
28 Apr - 29 Apr
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

10.0 out of 10, Exceptional, (84)
"House was just as it looked in pictures. Great yard and hot tub. Close to all the cape has to offer. Will stay again !"
The price is AED 1,102
AED 2,623 total
includes taxes & fees
26 May - 27 May
WATERFRONT w/Kayaks & SUP’s ★ Pet friendly ★ HOT TUB★Firepit & FPL★Deck & Patio

Cape Cod cottage

9.6 out of 10, Exceptional, (100)
"The hosts are lovely and left us some suggestions for our visit since it was our first time on the cape. Everything they suggested was a hit with the family. The house was easy to find and clean. Great stop for a quick trip. "
Cape Cod cottage

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

10.0 out of 10, Exceptional, (78)
"We were three generations, ages 1 to 74, who enjoyed the house and its broad views across the water. The property was clean, well-maintained, thoughtfully designed and furnished, and comfortable, with ample room for all six of us. The owner, Scott, was easy to communicate with. The neighborhood is quiet, with a community beach close by. Overall, as all the other reviewers have commented, this easily earns a five star rating."
The price is AED 2,568
AED 5,255 total
includes taxes & fees
18 May - 19 May
Coastal chic meets French Provençal in this newly renovated oceanfront home.

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

10.0 out of 10, Exceptional, (103)
"Host was always responsive. Property was even better than listing pictures. Location cannot be beat. The perfect gathering place for our Fall Friends Getaway. Already booked for next year! "
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

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

9.6 out of 10, Exceptional, (49)
"We had a wonderful time. The home is clean, comfortable, well furnished, and extremely well stocked. Plenty of dish detergent, paper towels, soap, etc. and they even provided travel size containers of shampoo and conditioner. Great location within walking distance to the beach. Would definitely stay here again."
Charming cottage with deck, yard, & AC - walk to beach, Main Street, & ferry

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

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

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

9.0 out of 10, Wonderful, (2)
"The location worked perfectly for us. Thanks, Ed! "
The price is AED 367
AED 1,080 total
includes taxes & fees
4 May - 5 May
Oldest Town of Cape Cod In The Historic District

Stunning Oceanfront Home With Amazing Views ~ Private Beach - capeoceanvista

9.6 out of 10, Exceptional, (109)
"Absolutely gorgeous location with amazing views and lots of privacy in the winter. Will stay again!"
Stunning Oceanfront Home With Amazing Views ~ Private Beach - capeoceanvista

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

9.6 out of 10, Exceptional, (15)
"We were in town for a family wedding, and our group had all adults. The dining room is a nice space. The kitchen is a bit small. Overall, the house was clean and perfectly located. There were a few aspects that were less convenient . We would have liked to the ootion of having a full coffee pot. Atrash cans "
Charming coastal home with large yard, firepit, & grill - pool and beach access

Cozy Yarmouth Cottage

9.6 out of 10, Exceptional, (5)
"Beautiful and comfortable space perfect for our family of four. "
The price is AED 441
AED 1,059 total
includes taxes & fees
5 May - 6 May
Cozy Yarmouth Cottage

Close to Bike Path 1 Mile to Beaches!

9.6 out of 10, Exceptional, (16)
"Great place to use as a base to explore Cape Cod. Well stocked, clean, and quiet. Had some problem with the TV, but the company responded quickly and had someone out to fix it right away. "
Close to Bike Path 1 Mile to Beaches!

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

10.0 out of 10, Exceptional, (5)
"Wonderful Location, close to the ferry at Hyannis. Centrally located on the Cape. The view over Brewster Pond is amazing. House is wonderfully done and furnished. "
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

10.0 out of 10, Exceptional, (167)
"Great location and host was easy to talk to. The house was nice and plenty spacious enough for 2 families. Great central location to beaches and restaurants. "
Falmouth Cape - Walk to Island Queen ferry to Martha's Vineyard, Beach, Downtown

Hot Tub, 200 ft to Beach!

9.8 out of 10, Exceptional, (8)
"Very nice and clean. Good location and food in the area is delicious. Great spot to rest and recharge on a short getaway with friends. Hot tub was a great addition to our trip. Thanks!"
Hot Tub, 200 ft to Beach!

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

10.0 out of 10, Exceptional, (145)
"Property was exactly as expected. Not only pet friendly, but catered to our pet. Was the cleanest place I have ever stayed that allowed pets. Communication was outstanding."
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

3.5 star property
8.8 out of 10, Excellent, (267)
"I love staying here "
The price is AED 663
AED 759 total
includes taxes & fees
8 May - 9 May
Edgewater Beach Resort, a VRI resort

InnSeason Resorts Captain's Quarters

3.5 star property
9.8 out of 10, Exceptional, (167)
"Enjoyed walking on the beach across the street from the property."
InnSeason Resorts Captain's Quarters

The Cove At Yarmouth

3.0 star property
9.2 out of 10, Wonderful, (234)
"Great stay "
The price is AED 502
AED 575 total
includes taxes & fees
29 Apr - 30 Apr
The Cove At Yarmouth
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.