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

Frederick William House
Front of property

Frederick William House

3.5 star property
9.6 out of 10, Exceptional, (247)
"We had a great get away and the Frederick William Inn was so charming. Extremely clean and comfortable. Can't wait to go back! Thank you!"
Frederick William House
Inn on Main
Front of property

Inn on Main

3.5 star property
10.0 out of 10, Exceptional, (66)
"The Inn was clean, comfortably and welcoming. Owners were friendly and knowledgeable, pointing out activities close to the Inn and an online guidebook sent by SMS so we could plan our stay. Really appreciated the small touches throughout that made this place comfortable. Sarah and Chris are great hosts. "
The price is SAR 744
SAR 852 total
includes taxes & fees
12 Jan - 13 January 2025
Inn on Main
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 635
SAR 727 total
includes taxes & fees
30 Dec - 31 Dec
The Village Inn Cape Cod
The Captain Farris House B&B
Exterior

The Captain Farris House B&B

3.5 star property
9.8 out of 10, Exceptional, (210)
"Jeff and Carol are wonderful hosts, made us feel at home. Breakfast was excellent, room was immaculate and romantic, a great get away!"
The Captain Farris House B&B
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 687
SAR 786 total
includes taxes & fees
15 Jan - 16 January 2025
The Palmer House Inn
Inn on the Sound
Beach

Inn on the Sound

3.5 star property
9.8 out of 10, Exceptional, (186)
"We an amazing stay at the Inn at the Sound. I would highly recommend to anyone traveling to the area!"
The price is SAR 898
SAR 1,028 total
includes taxes & fees
15 Jan - 16 January 2025
Inn on the Sound
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
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
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
The Old Manse Inn
Room

The Old Manse Inn

4.5 star property
9.8 out of 10, Exceptional, (242)
"Lovely little B&B. Owners are delightful. 10 ish mins walk to the beach"
The Old Manse Inn
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
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 969
SAR 1,109 total
includes taxes & fees
14 Jan - 15 January 2025
Brewster by the Sea 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
Isaiah Jones Homestead Bed & Breakfast
Front of property

Isaiah Jones Homestead Bed & Breakfast

3.0 star property
9.2 out of 10, Wonderful, (271)
"Bob and Analisa were wonderful inn keepers. We felt as close to family as one could get in a few days. Adorable village"
Isaiah Jones Homestead Bed & Breakfast
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
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
Candleberry Inn on Cape Cod
Exterior detail

Candleberry Inn on Cape Cod

4.5 star property
10.0 out of 10, Exceptional, (126)
"Marco and Angelo very welcoming hosts!"
Candleberry Inn on Cape Cod
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, (307)
"accommodation was good but cleanliness could have been better. Not bad but some areas needed more attention. Good restaurant and bar service on Thursday. No restaurant available on Saturday."
The price is SAR 589
SAR 674 total
includes taxes & fees
26 Dec - 27 Dec
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, (255)
"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
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 Palmer House Inn: 17 rooms. Situated 13.1 mi (21 km) from the heart of Osterville. Enjoy the free full breakfast and unique décor. Inn on Main: 6 rooms. 8.9 mi (14.3 km) from the heart of downtown. Enjoy the free cooked breakfast and designer toiletries. 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.