Find a Bed and Breakfast in Osterville from CA $227

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Check prices for these dates

Next weekend
Aug 22 - Aug 24
In two weeks
Aug 29 - Aug 31
In one month
Sep 12 - Sep 14
In two months
Oct 10 - Oct 12

Browse Select Osterville B&B

Frederick William House
Dining

Frederick William House

3.5 star property
9.6 out of 10, Exceptional, (279)
"Wonderful stay! Close to access Main Street and other things we wanted to do. "
The price is CA $305
CA $349 total
includes taxes & fees
Aug 18 - Aug 19
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, (221)
"Charming, chic, centrally located, and clean B&B with a thoughtful breakfast (i.e., vegan options). I very much enjoyed my stay. The staff is fantastic--both helpful and friendly. I would stay again."
The price is CA $680
CA $760 total
includes taxes & fees
Sep 9 - Sep 10
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, (47)
"Loved this B&B very comfortable and the staff was so nice and helpful! "
The price is CA $227
CA $299 total
includes taxes & fees
Sep 1 - Sep 2
An English Garden Bed & Breakfast
Inn on the Sound
Exterior

Inn on the Sound

3.5 star property
9.8 out of 10, Exceptional, (205)
"Quiet, charming, nice breakfast, right across from beach"
The price is CA $604
CA $692 total
includes taxes & fees
Sep 8 - Sep 9
Inn on the Sound
Winstead Beach Resort
Front of property

Winstead Beach Resort

4.0 star property
9.2 out of 10, Wonderful, (54)
"Wonderful location! Excellent service from the time of arrival including departure 5 days later. All staff provided a relaxing stay. Amenities were top notch including a wonderful variety of food for breakfast. Will definitely return next July."
The price is CA $540
CA $655 total
includes taxes & fees
Aug 14 - Aug 15
Winstead Beach Resort
The Captain Farris House B&B
Exterior

The Captain Farris House B&B

3.5 star property
9.8 out of 10, Exceptional, (233)
"We loved this B&B it was so quaint and beautiful. Loved our room and the breakfast. The staff was amazing! "
The price is CA $309
CA $353 total
includes taxes & fees
Sep 3 - Sep 4
The Captain Farris House B&B
The Inn at Yarmouth Port
View from room

The Inn at Yarmouth Port

4.0 star property
9.6 out of 10, Exceptional, (114)
"We liked everything, the hosts were amazing and helpful, breakfasts top-notch, great climate control in the room, modern comfort in historic setting"
The price is CA $432
CA $495 total
includes taxes & fees
Sep 12 - Sep 13
The Inn at Yarmouth Port
Belfry Inn & Bistro
3 bars/lounges

Belfry Inn & Bistro

3.5 star property
9.0 out of 10, Wonderful, (186)
"X"
Belfry Inn & Bistro
Mulberry Bed & Breakfast
Front of property

Mulberry Bed & Breakfast

2.5 star property
9.2 out of 10, Wonderful, (64)
"Restful stay, close to the beach & restaurants. Lovely breakfasts & kind host."
Mulberry Bed & Breakfast
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, (86)
"We absolutely loved our stay at the Inn at Cape Cod. The owners were very friendly & make you feel right at home. Our room was comfortable and breakfast was great! I would definitely recommend to any visitors. "
The price is CA $522
CA $597 total
includes taxes & fees
Sep 4 - Sep 5
The Inn At Cape Cod
The Palmer House Inn
Beach nearby

The Palmer House Inn

3.5 star property
9.6 out of 10, Exceptional, (175)
"Superb staff and bkfsts Wonderful porch"
The price is CA $494
CA $565 total
includes taxes & fees
Sep 1 - Sep 2
The Palmer House Inn
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, (134)
"Stunning bed and breakfast. Amazing owners and a experience you won’t forget."
The price is CA $470
CA $537 total
includes taxes & fees
Sep 4 - Sep 5
Candleberry Inn on Cape Cod
Isaiah Hall Bed & Breakfast Inn
Front of property

Isaiah Hall Bed & Breakfast Inn

3.0 star property
9.6 out of 10, Exceptional, (121)
"Cute little getaway. We were only there a night but loved it!! Hosts super nice and room was great. Great location and nice backyard area. Walking to the beach was easy (although there was no sidewalks) Would 1000% go back!"
The price is CA $390
CA $446 total
includes taxes & fees
Aug 17 - Aug 18
Isaiah Hall Bed & Breakfast Inn
The Tern Inn Bed & Breakfast and Cottages
Free daily full breakfast

The Tern Inn Bed & Breakfast and Cottages

3.5 star property
9.2 out of 10, Wonderful, (228)
"Amazing stay. Very respectful hosts. "
The Tern Inn Bed & Breakfast and Cottages
Inn on Main
Outdoor dining

Inn on Main

3.5 star property
10.0 out of 10, Exceptional, (69)
"What a great place! Central location made it super easy to get around. Hosts were fantastic- very nice, welcoming and very helpful with great restaurant, beach or visit recommendations. I highly recommend The Inn on Main."
The price is CA $411
CA $471 total
includes taxes & fees
Aug 14 - Aug 15
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 CA $462
CA $529 total
includes taxes & fees
Aug 28 - Aug 29
Brewster by the Sea Inn
Liberty Hill Inn
Normandy Room

Liberty Hill Inn

3.5 star property
10.0 out of 10, Exceptional, (125)
"5* beautiful inn with fabulous hosts! Breakfast beyond what you’d expect, hot cookies in the afternoon, spotless inside, great attention to every detail!"
The price is CA $450
CA $515 total
includes taxes & fees
Aug 17 - Aug 18
Liberty Hill Inn
The Old Manse Inn
View from property

The Old Manse Inn

4.5 star property
9.8 out of 10, Exceptional, (247)
"The Old Manse Inn is amazing and everything they advertise! "
The price is CA $448
CA $513 total
includes taxes & fees
Aug 26 - Aug 27
The Old Manse Inn
Sea Street Inn
Luxury King Room

Sea Street Inn

4.0 star property
10.0 out of 10, Exceptional, (41)
"Very nicely renovated small property with a fantastic breakfast."
The price is CA $594
CA $680 total
includes taxes & fees
Aug 14 - Aug 15
Sea Street Inn
Captain David Kelley House Bed & Breakfast
Garden

Captain David Kelley House Bed & Breakfast

3.5 star property
10.0 out of 10, Exceptional, (42)
"Outstanding room and breakfast. "
Captain David Kelley House Bed & Breakfast
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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Top Osterville Hotel Reviews

Bayside Resort Hotel

Bayside Resort Hotel

10/10 Excellent
"The staff was great and all helpful:front desk, breakfast servers, cleaners and outdoor bartender. The hotel grounds were well maintained and the back marsh was peaceful to sit at with a morning coffee or fire pit at night. The hotel was very family friendly. "
Talia 3-night trip
Posted 19 hours ago
Bayside Resort Hotel

Frequently asked questions

What is the nightly rate for a B&B in Osterville?
Prices for B&Bs in Osterville often vary, but you can find a great deal from CA $227 with Expedia. All sorts of factors affect price, such as location and the time of year. It usually costs more to stay at Osterville B&Bs over the weekend too. Travelers can find the best deals by being flexible with their dates, and by using our filters to sort prices from low to high.
What is the difference between a Osterville Bed and Breakfast and a hotel?
Every Osterville B&B has its own unique feel. Whether it's a cozy reading space or a sunlit breakfast nook to enjoy your morning cup of coffee, the quaint details are what make bed and breakfasts a home away from home. Travelers can look forward to personal touches, thoughtful amenities and of course a scrumptious breakfast at Osterville B&Bs.