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Compare 482 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, (105)
"This was a very nice, clean and comfortable place for my sister and I to stay to enjoy the Cape Cod experience We had a great stay here! It was drivable in day trips to all of the activities we wanted to do! (Nantucket, Marthas Vineyard, lighthouses, Ptown, etc.). Highly recommend! "
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, (165)
"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, (191)
"We enjoyed our stay at this cute cottage. It was clean and comfortable, with extra blankets for the chilly nights. It was nicely located to accommodate our beach hopping and to explore the many quaint towns and villages on the Cape. One drawback was the TV was a bit frustrating to use."
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, (38)
"We have stayed here 2-3 times and absolutely love this home! It's clean and very comfortable! We will return !"
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, (43)
"This was our first trip to the Cape; it will not be our last. The cottage is in great location, the listing is exactly as described. It was perfect my husband and myself and our mini doxie. Paul was great in communication and made everything so easy and enjoyable."
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)
"Nice 1-bedroom with easily accessible loft within walking distance of Woods Hole village. Very clean with a nice kitchen and bath. Needs some attention to the yard and to the sump pump. I was also disappointed that the window air conditioners had not been installed yet."
The price is AED 441
AED 1,392 total
includes taxes & fees
4 Nov 2024 - 5 Nov 2024
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, (92)
"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, (18)
"This condo was clean and perfectly situated for our long weekend on the Cape. Just steps from the private beach with great views. And the location is perfect - super easy to get to restaurants and shopping!"
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, (15)
"Beautiful place"
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 AED 1,807
AED 2,704 total
includes taxes & fees
3 Nov 2024 - 4 Nov 2024
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
9.2 out of 10, Wonderful, (36)
"Highly recommend."
Dog-friendly cape home with Wifi, deck, grill, fireplace, & outdoor shower
Edgewater Beach Resort, a VRI resort
Courtyard
Edgewater Beach Resort, a VRI resort
3.5 star property
8.8 out of 10, Excellent, (252)
"We loved our stay! The 1 bedroom was very clean fully equipped with everything we needed. All the extras like soap for dishes , dishwasher towels for the pool. Pool area very clean beautiful grounds. Friendly staff. "
Edgewater Beach Resort, a VRI resort
Oceanside 2 - SD335
Exterior
Oceanside 2 - SD335
9.8 out of 10, Exceptional, (12)
"House is set behind a dune. dune is a little steep, especially climbing back up. Kind of tough for the elderly. Set up of the house was good for 2 seniors. Many restaurants close by. Quiet area."
Oceanside 2 - SD335
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 AED 441 and AED 1,807 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?
A traveler favorite is Sun Retreats Peters Pond. Make yourself at home at this 2.5-star stay which offers a swimming pool and a barbecue grill. 11 Mashpee - 2 Bedroom Cottage is another recommended option worth shortlisting. Put your bags down at this 3.5-star cottage and take advantage of conveniences such as a barbecue grill and a nearby bay. You can pick from multiple cottages in Osterville with a total average guest review rating of 9.5.
How many cottages are there in Osterville?
Choose from 482 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.