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Check prices for these dates

Next weekend
6 Jun - 8 Jun
In two weeks
13 Jun - 15 Jun
In one month
27 Jun - 29 Jun
In two months
25 Jul - 27 Jul

Compare 80 B&B in Osterville with updated reviews, rates, and availability.

Frederick William House
Dining

Frederick William House

3.5 star property
9.6 out of 10, Exceptional, (259)
"A cozy place for a few nights."
The price is AED 658
AED 753 total
includes taxes & fees
1 Jun - 2 Jun
Frederick William House
The Christopher, The Edgartown Collection
Front of property

The Christopher, The Edgartown Collection

3.0 star property
9.8 out of 10, Exceptional, (198)
"Ideal location, beautiful rooms, and great shared spaces. And the staff - fantastic!"
The price is AED 1,319
AED 1,473 total
includes taxes & fees
1 Jun - 2 Jun
The Christopher, The Edgartown Collection
Mulberry Bed & Breakfast
Front of property

Mulberry Bed & Breakfast

2.5 star property
9.2 out of 10, Wonderful, (60)
"Restful stay, close to the beach & restaurants. Lovely breakfasts & kind host."
Mulberry Bed & Breakfast
Belfry Inn & Bistro
3 bars/lounges

Belfry Inn & Bistro

3.5 star property
9.0 out of 10, Wonderful, (181)
"It's always a great stay at the Belfry! The innkeeper is very friendly and helpful. I like walking down to the boardwalk and there's a few very nice shops nearby. "
Belfry Inn & Bistro
The Captain Farris House B&B
Exterior

The Captain Farris House B&B

3.5 star property
9.8 out of 10, Exceptional, (218)
"Great stay. B&B has a great location and the staff was very nice!"
The price is AED 1,061
AED 1,215 total
includes taxes & fees
5 Jun - 6 Jun
The Captain Farris House B&B
An English Garden Bed & Breakfast
Terrace/patio

An English Garden Bed & Breakfast

3.0 star property
9.0 out of 10, Wonderful, (40)
"Great B&B would definitely stay again!"
The price is AED 642
AED 840 total
includes taxes & fees
15 Jun - 16 Jun
An English Garden Bed & Breakfast
The Village Inn Cape Cod
Garden

The Village Inn Cape Cod

3.5 star property
10.0 out of 10, Exceptional, (218)
"Wonderful B&B. Robin and Claire were fantastic hosts, very knowledgeable about Cape Cod with great recommendations. Breakfast was amazing - one of the best quiches we’ve ever had!"
The Village Inn Cape Cod
Inn on the Sound
Exterior

Inn on the Sound

3.5 star property
9.8 out of 10, Exceptional, (202)
"An Absolutely Amazing bed and breakfast. "
The price is AED 1,172
AED 1,341 total
includes taxes & fees
31 May - 1 Jun
Inn on the Sound
The Old Manse Inn
View from property

The Old Manse Inn

4.5 star property
9.8 out of 10, Exceptional, (242)
"Friendly staff, Great breakfast, Treated us wonderful!!"
The price is AED 986
AED 1,128 total
includes taxes & fees
9 Jun - 10 Jun
The Old Manse Inn
Inn on Main
Outdoor dining

Inn on Main

3.5 star property
10.0 out of 10, Exceptional, (68)
"Terrific B&B on Cape Cod - super dog friendly and very hospitable! Excellent breakfasts, charming space, and wonderful hosts. It’s a very convenient mid-Cape location, you will not regret booking with them."
The price is AED 1,433
AED 1,640 total
includes taxes & fees
4 Jun - 5 Jun
Inn on Main
Brewster by the Sea Inn
Terrace/patio

Brewster by the Sea Inn

4.0 star property
9.8 out of 10, Exceptional, (167)
"Brewster By the Sea has it all - great location, amazing innkeeper, unbelievable breakfasts, and great rooms with perfect amenities. "
The price is AED 1,626
AED 1,861 total
includes taxes & fees
16 Jun - 17 Jun
Brewster by the Sea Inn
Winstead Beach Resort
Front of property

Winstead Beach Resort

4.0 star property
9.2 out of 10, Wonderful, (51)
"Fabulous location right on the beach."
The price is AED 846
AED 1,027 total
includes taxes & fees
2 Jun - 3 Jun
Winstead Beach Resort
Candleberry Inn on Cape Cod
Luxury Suite, 1 King Bed, Jetted Tub, Garden Area | Terrace/patio

Candleberry Inn on Cape Cod

4.5 star property
10.0 out of 10, Exceptional, (127)
"quaint inn"
The price is AED 1,098
AED 1,257 total
includes taxes & fees
2 Jun - 3 Jun
Candleberry Inn on Cape Cod
The Inn At Cape Cod
Front of property - evening/night

The Inn At Cape Cod

4.0 star property
9.6 out of 10, Exceptional, (83)
"Amazing inn and the owners are great!"
The Inn At Cape Cod
Isaiah Hall Bed & Breakfast Inn
Front of property

Isaiah Hall Bed & Breakfast Inn

3.0 star property
9.8 out of 10, Exceptional, (115)
"Lovely room in historic ship builder’s home, kind staff, good location amid the gardens and beach! "
The price is AED 984
AED 1,126 total
includes taxes & fees
1 Jun - 2 Jun
Isaiah Hall Bed & Breakfast Inn
Captain Freeman Inn
Outdoor pool, open 7:00 AM to 7:00 PM, pool umbrellas, sun loungers

Captain Freeman Inn

4.0 star property
10.0 out of 10, Exceptional, (70)
"The room I stayed in was gorgeous. "
The price is AED 1,304
AED 1,492 total
includes taxes & fees
9 Jun - 10 Jun
Captain Freeman Inn
The Palmer House Inn
Beach nearby

The Palmer House Inn

3.5 star property
9.6 out of 10, Exceptional, (174)
"Nice place to stay"
The price is AED 1,582
AED 1,811 total
includes taxes & fees
31 May - 1 Jun
The Palmer House Inn
Lamb and Lion Inn
Seasonal outdoor pool, open 8:00 AM to 10:00 PM, pool umbrellas

Lamb and Lion Inn

3.0 star property
9.6 out of 10, Exceptional, (24)
"Historic, rustic, Cape Cod at its best. "
Lamb and Lion Inn
The Tern Inn Bed & Breakfast and Cottages
Exterior

The Tern Inn Bed & Breakfast and Cottages

3.5 star property
9.2 out of 10, Wonderful, (224)
"The owners are amazing hosts "
The Tern Inn Bed & Breakfast and Cottages
Long Dell Inn
Exterior

Long Dell Inn

3.5 star property
9.4 out of 10, Exceptional, (179)
"Great location and awesome breakfast’s "
The price is AED 1,208
AED 1,383 total
includes taxes & fees
7 Jun - 8 Jun
Long Dell 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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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’d like to spend some time by the water during your time in Osterville, Cape Cod Beaches and Dowses Beach are worth a stop.
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 B&Bs in the surrounding area: Frederick William House: 5 rooms. 12.6 mi (20.3 km) from the downtown core. Enjoy the soaking bathtubs and deli. The Christopher, The Edgartown Collection: 15 rooms. Situated 17.8 mi (28.7 km) from the heart of Osterville. Enjoy the unique décor and patio area. 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. Belfry Inn & Bistro: 16 rooms. Located 10.6 mi (17 km) from the core of Osterville. Enjoy the onsite dining and bars.
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.