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Compare 72 B&B in Osterville with updated reviews, rates, and availability.

The Christopher, The Edgartown Collection
Front of property

The Christopher, The Edgartown Collection

3.0 star property
9.8 out of 10, Exceptional, (196)
"Lovely hotel in Edgartown. Beautifully appointed rooms and common areas. Good breakfast. Walkable to nice restaurants."
The Christopher, The Edgartown Collection
An English Garden Bed & Breakfast
Terrace/patio

An English Garden Bed & Breakfast

3.0 star property
9.0 out of 10, Wonderful, (39)
"Great property very near the beach. Staff very friendly and helpful"
An English Garden Bed & Breakfast
Frederick William House
Front of property

Frederick William House

3.5 star property
9.6 out of 10, Exceptional, (244)
"It was a cute B&B. The owner was not there when we arrived but I left her a message and she called back and gave me walking directions to the ferry to Martha’s Vineyard. She also recommended a great restaurant for dinner. The dining room fir breakfast was nice and she gave us information about the house and neighborhood. The outside was nice with tables and would be nice in the summer."
The price is SAR 598
SAR 684 total
includes taxes & fees
23 Nov - 24 Nov
Frederick William House
Inn on Main
Front of property

Inn on Main

3.5 star property
10.0 out of 10, Exceptional, (63)
"The hosts Sarah and Chris were very friendly and helpful, the room was spotless and very comfortable, fabulous breakfast, would definitely stay again if I went back to Cape Cod. "
The price is SAR 681
SAR 779 total
includes taxes & fees
23 Nov - 24 Nov
Inn on Main
The Captain Farris House B&B
Exterior

The Captain Farris House B&B

3.5 star property
9.8 out of 10, Exceptional, (209)
"We had a delightful stay at Captain Farris House B&B, our room was fantastic, the hospitality first class and the breakfast was quite delicious. We cannot wait to visit again."
The price is SAR 882
SAR 1,010 total
includes taxes & fees
25 Nov - 26 Nov
The Captain Farris House B&B
Inn on the Sound
Beach

Inn on the Sound

3.5 star property
9.8 out of 10, Exceptional, (184)
"This is a perfect getaway . "
The price is SAR 1,085
SAR 1,242 total
includes taxes & fees
23 Nov - 24 Nov
Inn on the Sound
Mulberry Bed & Breakfast
Front of property

Mulberry Bed & Breakfast

2.5 star property
9.2 out of 10, Wonderful, (60)
"MS.Fran was very nice and a pleasant to talk with."
Mulberry Bed & Breakfast
Isaiah Hall Bed & Breakfast Inn
Front of property

Isaiah Hall Bed & Breakfast Inn

3.0 star property
9.8 out of 10, Exceptional, (114)
"Wonderful bed and breakfast. Friendly hosts. Homemade cranberry bread for breakfast!"
Isaiah Hall Bed & Breakfast Inn
The Inn At Cape Cod
Room

The Inn At Cape Cod

4.0 star property
9.6 out of 10, Exceptional, (83)
"The Inn itself is a National Treasure and the couple that run the Inn are an even greater treasure. Incredible experience. Thank you for the uncompromising effort. "
The Inn At Cape Cod
The Tern Inn Bed & Breakfast and Cottages
Front of property

The Tern Inn Bed & Breakfast and Cottages

3.5 star property
9.2 out of 10, Wonderful, (224)
"John and Lisa were wonderful hosts. Our room was lovely and had everything to make our stay very comfortable. "
The Tern Inn Bed & Breakfast and Cottages
The Inn at Yarmouth Port
Property entrance

The Inn at Yarmouth Port

4.0 star property
9.6 out of 10, Exceptional, (109)
"Very lovely inn and innkeepers, Debra and Rene were very welcoming. Breakfast everyday on the patio was a delight. Clean room, downstairs sitting area very comfortable and inviting. "
The Inn at Yarmouth Port
The Palmer House Inn
Exterior

The Palmer House Inn

3.5 star property
9.6 out of 10, Exceptional, (168)
"Nice place to stay"
The price is SAR 643
SAR 736 total
includes taxes & fees
9 Dec - 10 Dec
The Palmer House Inn
The Village Inn Cape Cod
Front of property

The Village Inn Cape Cod

3.5 star property
10.0 out of 10, Exceptional, (211)
"From the moment we arrived Robin and Claire made us feel so welcome. Our room was beautifully appointed, quiet, and comfortable. Every morning my husband and could not wait for the amazing breakfast prepared by Claire, her attention to detail and thoughtful touches made our stay truly special, and Robin gave us spectacular recommendations on local spots to explore. Truly the best part of our New England adventure!"
The price is SAR 634
SAR 726 total
includes taxes & fees
30 Nov - 1 Dec
The Village Inn Cape Cod
Belfry Inn & Bistro
Room

Belfry Inn & Bistro

3.5 star property
9.0 out of 10, Wonderful, (174)
"A pleasant place to stay. nice setting."
Belfry Inn & Bistro
Lamb and Lion Inn
Outdoor pool

Lamb and Lion Inn

3.0 star property
9.6 out of 10, Exceptional, (24)
"Beautiful location. We loved time at the pool and hot tub. everyone was super friendly. "
Lamb and Lion Inn
Winstead Beach Resort
Beach/ocean view

Winstead Beach Resort

4.0 star property
9.2 out of 10, Wonderful, (51)
"Chose the property for a weekend getaway. Lovely place and very nice and friendly staff."
Winstead Beach Resort
Brewster by the Sea Inn
Exterior

Brewster by the Sea Inn

4.0 star property
9.8 out of 10, Exceptional, (165)
"Amy is amazing. She makes ever effort to make everything PERFECT!"
The price is SAR 1,194
SAR 1,366 total
includes taxes & fees
3 Dec - 4 Dec
Brewster by the Sea Inn
Liberty Hill Inn
Property grounds

Liberty Hill Inn

3.5 star property
10.0 out of 10, Exceptional, (124)
"I'm not a fan of Bed and Breakfasts only because you just never know what you are going to get in terms of safety, privacy, air conditioning, room or amenities, but most are not like the Liberty Hill Inn. In fact I've never stayed in a property I've enjoyed as much as Liberty Hill Inn. You don't need me to rave about the hosts, everyone else has done that, and raves they deserve, but I will say every detail was seen to, everything exceeded my expectation, our room was pristine and appointed with...
Liberty Hill Inn
Pepper House Inn
Front of property

Pepper House Inn

3.0 star property
6.8 out of 10, (68)
"Debby was very kind. We appreciated her daily breakfasts! Definitely would recommend. "
Pepper House Inn
Captain Freeman Inn
Porch

Captain Freeman Inn

4.0 star property
10.0 out of 10, Exceptional, (70)
"The room I stayed in was gorgeous. "
Captain Freeman Inn
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

Searching for B&Bs in Osterville?
If you’re looking for something a little quirkier than your standard hotel experience, a stay at a bed and breakfast could be the perfect alternative for your getaway. If you’re hoping to spend some time walking along the water in Osterville, Cape Cod Beaches is worth a visit.
Why consider a B&B versus a traditional hotel?
With attentive service, opportunities to meet guests from other places, and of course a scrumptious breakfast, B&Bs offer a unique setting.
What are the best B&Bs in Osterville?
Here are some well-liked B&Bs in the area: Frederick William House: 6 rooms. 12.6 mi (20.3 km) from the heart of Osterville. Enjoy the soaking bathtubs and deli. Inn on the Sound: 10 rooms. 12.4 mi (20 km) from the downtown core. Enjoy the free full breakfast and library. The Captain Farris House B&B: 10 rooms. Situated 10.7 mi (17.2 km) from the heart of Osterville. Enjoy the free full breakfast and designer toiletries. An English Garden Bed & Breakfast: 11 rooms. 13.9 mi (22.3 km) from the heart of downtown. Enjoy the free full breakfast and patio area. The Christopher, The Edgartown Collection: 15 rooms. Located 17.8 mi (28.7 km) from the core of Osterville. Enjoy the unique décor and patio area.
What's the best time of year to book my B&B in Osterville?
When you’re dreaming of a stay in Osterville, year-round temperatures and rainfall may be important factors to consider. The hottest months are usually August and July with an average temp of 67°F, while the coldest months are February and January with an average of 37°F. Average annual precipitation for Osterville is 52 inches.
What is there to do in Osterville?
Spend some time exploring Cape Cod Beaches and Dowses Beach if you’re hoping to see some of the area’s natural features. You might put Stand Up & Paddle Cape Cod and Public Beach on your list if you want to see more of the area.
How can I get to and around Osterville?
You can plan your excursions in and around Osterville ahead of time with these transportation options. Fly into Hyannis, MA (HYA-Barnstable Municipal), which is located 5.8 mi (9.4 km) away from the city center. You can also search for flights into Vineyard Haven, MA (MVY-Martha’s Vineyard), which is 20.2 mi (32.5 km) away. If you’d like to venture out around the area, you may want to rent a car for your trip.