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Compare 471 Cottages in Osterville with updated reviews, rates, and availability.

Cape Cod Holiday Estates, a VRI resort
Property grounds

Cape Cod Holiday Estates, a VRI resort

3.0 star property
9.6 out of 10, Exceptional, (120)
"Nice & clean. The only complaint Would be that the pool closed at 6 PM because they were low on staff so by the time we got back from sightseeing, we weren’t able to get in the pool"
Cape Cod Holiday Estates, a VRI resort
Martha's Vineyard Getaway Cottage
Exterior

Martha's Vineyard Getaway Cottage

10.0 out of 10, Exceptional, (2)
"Bright, open, clean & cozy. Will return and love the year round option."
Martha's Vineyard Getaway Cottage
Steps to the beach with an ocean view,
Keyes Beach, 120 steps from the deck.

Steps to the beach with an ocean view,

10.0 out of 10, Exceptional, (109)
"We came to visit Nantucket and Martha’s Vineyard and one of the best parts of our trip is this gem. It was the perfect size for 4 of us. Close to the beach and the seashell collecting was amazing. Lots of shops and restaurants close by. We had some questions and the owner was very responsive. We would stay here again!"
Steps to the beach with an ocean view,
Cape Cod/Oceanfront on Nantucket Sound w/ Private Beach & Deck, Free Kayaks
True Oceanfront Gem! Private beach, deck, kayaks. 51 South Shore Dr, Yarmouth,

Cape Cod/Oceanfront on Nantucket Sound w/ Private Beach & Deck, Free Kayaks

9.8 out of 10, Exceptional, (166)
"Beautiful, well-equipped house right on the beach, convenient to Hyannis port and all the Cape has to offer. "
Cape Cod/Oceanfront on Nantucket Sound w/ Private Beach & Deck, Free Kayaks
Steps to the Ocean! Perfect Location!!!
Charming Cape Cod cottage just steps to the beach.

Steps to the Ocean! Perfect Location!!!

10.0 out of 10, Exceptional, (195)
"I spent the weekend in this adorable cottage after waking up in 5 different states 5 days in a row for a work trip. The location is perfect and the sunrise and sunsets from the beach were some of the most vibrant and colorful I have ever seen. I’m sure this is an amazing place to vacation in the summer but the quiet and solitude of November was its own treasure. And I was able to visit Walden Pond on my way to Boston Airport—-just a quick 30 minute detour and well worth the visit. "
Steps to the Ocean! Perfect Location!!!
⭐️FABULOUS-WATERFRONT⭐️3bdrm 2bth. Kayaks & Firepit⭐️
Waterfront on Follins Bay. Sit back on this beautiful stone patio and enjoy!

⭐️FABULOUS-WATERFRONT⭐️3bdrm 2bth. Kayaks & Firepit⭐️

10.0 out of 10, Exceptional, (86)
"Quiet, cozy, well-stocked house. Perfect summer hang. Conveniently located. "
⭐️FABULOUS-WATERFRONT⭐️3bdrm 2bth. Kayaks & Firepit⭐️
12 VINEYARD VIEW - FULLY RENOVATED
Exterior

12 VINEYARD VIEW - FULLY RENOVATED

9.8 out of 10, Exceptional, (39)
"We had such an amazing time staying here! The location is perfect and has amazing ocean views right from the house. Everything was super clean and well maintained. We will definitely be coming back! "
12 VINEYARD VIEW - FULLY RENOVATED
Cozy beachfront cottage at Chases Ocean Grove
Exterior

Cozy beachfront cottage at Chases Ocean Grove

9.8 out of 10, Exceptional, (24)
"Enjoyed coffee on the enclosed porch overlooking ocean. Great communication with owner. Bathroom nicely done. Very clean, cute, well setup for a cottage. "
Cozy beachfront cottage at Chases Ocean Grove
Lovely Cape Cottage 2 bedroom with private beach and central air.
Modern, clean living room.

Lovely Cape Cottage 2 bedroom with private beach and central air.

10.0 out of 10, Exceptional, (44)
"Such a cute and comfortable place. We enjoyed the neighborhood and the beach down the street. Owner was really responsive if we needed anything "
Lovely Cape Cottage 2 bedroom with private beach and central air.
THE BOAT HOUSE LOFT ~ PRIVATE WATERFRONT "BEACH HOUSE" ~ SHORT & LONG TERM STAYS
Ten windows in the spectacular "Ship's Bridge" veranda. Surrounded by water!

THE BOAT HOUSE LOFT ~ PRIVATE WATERFRONT "BEACH HOUSE" ~ SHORT & LONG TERM STAYS

9.4 out of 10, Exceptional, (107)
"Wonderful stay. Wish we had an additional week! The “loft” views of Swan Pond, with the breezes filtering in, made even our simplest of meals an experience! Whether using the complementary watercraft on the Pond or sitting and reading (or napping) by the pond, the salt air relaxed the soul. Even a rainy day in that “loft” made one feel like a kid in a tree house. Laurence is a Primo host!! Five Star! So knowledgeable and friendly, not at all intrusive, but so helpful. Our elderly canine...
THE BOAT HOUSE LOFT ~ PRIVATE WATERFRONT "BEACH HOUSE" ~ SHORT & LONG TERM STAYS
Charming Beach Cottage, Steps To Beach; Ocean Views, Reasonably Priced
Just steps from path down to the beach. Can easily go back and forth for baby's naps and lunch

Charming Beach Cottage, Steps To Beach; Ocean Views, Reasonably Priced

8.6 out of 10, Excellent, (79)
"Great location but the place was dirty. Need a better cleaning service. "
Charming Beach Cottage, Steps To Beach; Ocean Views, Reasonably Priced
Cozy cottage w/ remodeled kitchen - less than a mile from Woods Hole Ferry

Cozy cottage w/ remodeled kitchen - less than a mile from Woods Hole Ferry

7.8 out of 10, Good, (26)
" Affordable, clean, enjoyable experience "
The price is SAR 451
SAR 1,427 total
includes taxes & fees
23 Nov - 24 Nov
Cozy cottage w/ remodeled kitchen - less than a mile from Woods Hole Ferry
Adorable cottage on Cape Cod's historic Rt 6A
Seating area

Adorable cottage on Cape Cod's historic Rt 6A

10.0 out of 10, Exceptional, (134)
"Wonderful time at this beautifully decorated cottage. Great central location on the Cape. "
Adorable cottage on Cape Cod's historic Rt 6A
Oceanside Cottage condo next to beach 2bedroom 1bath for 4-6 people
Beach

Oceanside Cottage condo next to beach 2bedroom 1bath for 4-6 people

8.8 out of 10, Excellent, (26)
"The property was great and walkable to the beach, but needs a few upgrades. "
Oceanside Cottage condo next to beach 2bedroom 1bath for 4-6 people
Private condo in Maushop. Steps to beach, ocean, Popponesset Inn and Marketplace
Exterior

Private condo in Maushop. Steps to beach, ocean, Popponesset Inn and Marketplace

9.6 out of 10, Exceptional, (64)
"Great property in great location on Cape Cod. 30 min drive for ferry to Nantucket. 2 minute walk to Beach within neighborhood. Cozy and quiet. Would not hesitate to stay again. "
Private condo in Maushop. Steps to beach, ocean, Popponesset Inn and Marketplace
Adorable Cape Escape W/ Private Beach Access, Full Kitchen, & Perfect Location

Adorable Cape Escape W/ Private Beach Access, Full Kitchen, & Perfect Location

8.8 out of 10, Excellent, (17)
"This is a beautiful cozy cottage, perfect for a small family. Centrally located on the Cape close to a lot of sights and attractions. There is a beach and restaurant within walking distance. My granddaughters and I had a great stay this summer."
Adorable Cape Escape W/ Private Beach Access, Full Kitchen, & Perfect Location
Charming Antique Boathouse Located Directly On Long Pond.
.

Charming Antique Boathouse Located Directly On Long Pond.

9.8 out of 10, Exceptional, (93)
"The boat house was wonderful. It was perfect for me, right on Long Pond, everything I needed, within distance of all the places I went, the fall foliage was lovely and Lynn was fabulous. "
Charming Antique Boathouse Located Directly On Long Pond.
New Rental - 2 bedrooms, 1.5 baths, with magnificent views.
4 Race Point-Maushop Village

New Rental - 2 bedrooms, 1.5 baths, with magnificent views.

10.0 out of 10, Exceptional, (19)
"Everything was perfect. Super clean. Location was perfect. House had everything you need. The owner even made sure the weather was great. "
New Rental - 2 bedrooms, 1.5 baths, with magnificent views.
Entire cottage, walk to/from ferry & downtown, newly renovated, parking on site
Property grounds

Entire cottage, walk to/from ferry & downtown, newly renovated, parking on site

10.0 out of 10, Exceptional, (16)
"Warm and inviting property. Everything was perfect, from the solar lights on the patio to the fireplace in the living area. We enjoyed a walk to dinner. Walked to Carboat for coffee in the morning. Fun visit to Martha’s Vineyard and a pleasant stay in this house !"
Entire cottage, walk to/from ferry & downtown, newly renovated, parking on site
2bdrm Captains Cottage Steps to Beach and Downtown Edgartown with Pool!
Front view of Lighthouse Cottage

2bdrm Captains Cottage Steps to Beach and Downtown Edgartown with Pool!

9.8 out of 10, Exceptional, (7)
"Enjoyed the stay"
The price is SAR 1,901
SAR 2,806 total
includes taxes & fees
24 Nov - 25 Nov
2bdrm Captains Cottage Steps to Beach and Downtown Edgartown with Pool!
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

Dog-friendly cape home with Wifi, deck, grill, fireplace, & outdoor shower

Dog-friendly cape home with Wifi, deck, grill, fireplace, & outdoor shower

9.4 out of 10, Exceptional, (38)
"We enjoyed the time spending there. That is mostly fit us well due to the circumstance for which we were there. My wife liked every minute of it and so did I; but I simply wish there were some coffee there, along with the coffee maker. So, I wouldn’t have to go out just for that, the first night we got there. "
Dog-friendly cape home with Wifi, deck, grill, fireplace, & outdoor shower
The Club at New Seabury
Outdoor pool

The Club at New Seabury

3.5 star property
9.0 out of 10, Wonderful, (304)
"will definitely go back again .. awesome place! "
The price is SAR 554
SAR 634 total
includes taxes & fees
24 Nov - 25 Nov
The Club at New Seabury
Edgewater Beach Resort, a VRI resort
Courtyard

Edgewater Beach Resort, a VRI resort

3.5 star property
8.8 out of 10, Excellent, (254)
"This was my second stay here and it was lovely. We visited in November for a mother/daughters trip and stayed in the two bedroom suite. Rooms were very clean, had plenty of extra towels and the fireplace was lovely. We used the pool as well and walked on the beach. At sunrise on the beach we had a seal swim up and say hello. Excellent place to have a little R&R"
Edgewater Beach Resort, a VRI resort
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.

Frequently asked questions

How much do cottages in Osterville cost?
Rates for cottages in Osterville range between SAR 466 and SAR 1,901 per night. No matter your budget, you’re sure to find the perfect place to relax and reconnect with nature. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
What are the best cottages in Osterville?
Osterville has multiple cottages with a total average guest review rating of 9.5. Sun Retreats Peters Pond is a fantastic option if you love nature and an easy-breezy pace. Guests staying at this 2.5-star stay will enjoy amenities such as a barbecue grill and a swimming pool. 11 Mashpee - 2 Bedroom Cottage is another popular pick. This 3.5-star cottage has a barbecue grill and a playground.
How many cottages are there in Osterville?
Choose from 471 cottages in Osterville. Whether you’re taking a trip with the little ones or planning a weekend escape with your besties, Expedia can help you find the perfect space to enjoy the surrounding nature.
Why book your cottage in Osterville with Expedia?
Booking a cottage in Osterville is as easy as entering your travel dates and selecting your ideal place for a vacation in nature. From high-end retreats to low-cost properties and cottages that come with perks like free WiFi, Expedia has something for all traveler styles. As for the best offers around? We’ve got you covered!
How can I find cheap cottages in Osterville?
Expedia is here to help you look for cheap cottages in Osterville. To book your ideal stay in a few quick clicks, use our convenient filter tool to refine your search by star rating, budget and amenities.