Find a Bed and Breakfast in Osterville from CA $227

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Check prices for these dates

Next weekend
Aug 15 - Aug 17
In two weeks
Aug 22 - Aug 24
In one month
Sep 5 - Sep 7
In two months
Oct 3 - Oct 5

Browse Select Osterville B&B

Frederick William House
Enjoy a classic design with a view of lush greenery from the large window, a dining table, comfortable chair, and cabinet with decorative items.

Frederick William House

3.5 star property
9.6 out of 10, Exceptional, (278)
"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 26 - Aug 27
Frederick William House
The Christopher, The Edgartown Collection
Stately two-story building with a central entrance and symmetrical facade, surrounded by well-maintained landscaping.

The Christopher, The Edgartown Collection

3.0 star property
9.8 out of 10, Exceptional, (220)
"Lovely little place. Great location!"
The price is CA $650
CA $726 total
includes taxes & fees
Sep 1 - Sep 2
The Christopher, The Edgartown Collection
Inn on the Sound
Enjoy a seaside patio with ocean views, outdoor tables, and wicker chairs.

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 $646
CA $739 total
includes taxes & fees
Aug 11 - Aug 12
Inn on the Sound
An English Garden Bed & Breakfast
Relax on the spacious balcony with outdoor seating, surrounded by lush greenery and a large tree.

An English Garden Bed & Breakfast

3.0 star property
9.0 out of 10, Wonderful, (46)
"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
Winstead Beach Resort
Relax by the ocean with a tranquil view from the porch, surrounded by seating areas and a well-maintained lawn.

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 $524
CA $636 total
includes taxes & fees
Aug 12 - Aug 13
Winstead Beach Resort
The Captain Farris House B&B
Experience the charm of the Captain's House Inn, surrounded by beautifully maintained gardens and classic architecture.

The Captain Farris House B&B

3.5 star property
9.8 out of 10, Exceptional, (231)
"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 $297
CA $339 total
includes taxes & fees
Sep 3 - Sep 4
The Captain Farris House B&B
The Inn at Yarmouth Port
Relax in a serene garden setting with Adirondack chairs, a small table, and a stone bench amidst lush greenery.

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 $470
CA $538 total
includes taxes & fees
Aug 20 - Aug 21
The Inn at Yarmouth Port
Isaiah Hall Bed & Breakfast Inn
Experience the charm of the Isaiah Hall Inn, a historic building from 1857, surrounded by mature trees and a well-maintained garden.

Isaiah Hall Bed & Breakfast Inn

3.0 star property
9.6 out of 10, Exceptional, (120)
"We loved staying at the Isaiah Hall Bed & Breakfast! The host is amazing and the location is great! Highly recommend it!"
The price is CA $390
CA $447 total
includes taxes & fees
Aug 18 - Aug 19
Isaiah Hall Bed & Breakfast Inn
Belfry Inn & Bistro
Enjoy a classic bar experience with a selection of fine spirits and wine glasses at the ready.

Belfry Inn & Bistro

3.5 star property
9.0 out of 10, Wonderful, (185)
"A pleasant place to stay. nice setting."
Belfry Inn & Bistro
The Inn At Cape Cod
Stately two-story building with a central entrance and two balconies, each with a railing and small porch area.

The Inn At Cape Cod

4.0 star property
9.6 out of 10, Exceptional, (85)
"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 $577
CA $660 total
includes taxes & fees
Aug 6 - Aug 7
The Inn At Cape Cod
Inn on Main
Relax in the patio area with a fire pit, surrounded by a brick wall and a tree.

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 CA $430
CA $492 total
includes taxes & fees
Sep 1 - Sep 2
Inn on Main
The Tern Inn Bed & Breakfast and Cottages
Enjoy meals in this dining area with a long table and comfortable seating for all.

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
The Palmer House Inn
Guests can enjoy a serene beach experience with calm waters and scenic views.

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 $495
CA $566 total
includes taxes & fees
Sep 1 - Sep 2
The Palmer House Inn
The Old Manse Inn
Enjoy a serene beach experience with calm seas and vast rock formations.

The Old Manse Inn

4.5 star property
9.8 out of 10, Exceptional, (246)
"The Old Manse Inn is amazing and everything they advertise! "
The price is CA $449
CA $514 total
includes taxes & fees
Aug 26 - Aug 27
The Old Manse Inn
Liberty Hill Inn
Relax in a classic bedroom with a large bed, floral wallpaper, and a view of the outdoors.

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 $451
CA $516 total
includes taxes & fees
Aug 17 - Aug 18
Liberty Hill Inn
Captain David Kelley House Bed & Breakfast
Welcome to Captain David Kelley House, where a traditional entrance and lush greenery create a peaceful atmosphere.

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
The Village Inn Cape Cod
Relax in a serene garden setting with a charming pavilion and two Adirondack chairs.

The Village Inn Cape Cod

3.5 star property
10.0 out of 10, Exceptional, (220)
"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
Lamb and Lion Inn
Relax by the pool and unwind in the hot tub.

Lamb and Lion Inn

3.0 star property
9.6 out of 10, Exceptional, (27)
"Very nice and comfortable. It was pleasure to talk with the innkeeper Loren. She was so helpful, kind. Great location to the beach, restaurants and hiking. We really enjoyed. "
Lamb and Lion Inn
Candleberry Inn on Cape Cod
Relax in a stylish outdoor seating area with a comfortable sofa, armchair, and small table.

Candleberry Inn on Cape Cod

4.5 star property
10.0 out of 10, Exceptional, (132)
"Stunning bed and breakfast. Amazing owners and a experience you won’t forget."
The price is CA $470
CA $538 total
includes taxes & fees
Sep 4 - Sep 5
Candleberry Inn on Cape Cod
The Platinum Pebble Boutique Inn - Adults Only
Relax in a serene outdoor setting surrounded by lush greenery, with a cozy fireplace and comfortable seating for two.

The Platinum Pebble Boutique Inn - Adults Only

4.0 star property
9.8 out of 10, Exceptional, (20)
"Wonderful stay, could not recommend this B&B more! Great breakfast, beautiful room, perfect location."
The Platinum Pebble Boutique Inn - Adults Only
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

Aiden by Best Western Cape Cod - West Yarmouth

Aiden by Best Western Cape Cod - West Yarmouth

10/10 Excellent
"Great location. Looks new in and out"
SURRENDRA 1-night trip
Posted 1 day ago
Aiden by Best Western Cape Cod - West Yarmouth

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.