Book Osterville Bed & Breakfast

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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

B&B in Osterville

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. "
$221 nightly
The price is $253
Aug 26 - Aug 27
Total includes taxes and fees
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!"
$524 nightly
The price is $585
Sep 1 - Sep 2
Total includes taxes and fees
The Christopher, The Edgartown Collection
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, (47)
"Loved this B&B very comfortable and the staff was so nice and helpful! "
$190 nightly
The price is $217
Sep 1 - Sep 2
Total includes taxes and fees
An English Garden Bed & Breakfast
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"
$369 nightly
The price is $422
Sep 8 - Sep 9
Total includes taxes and fees
Inn on the Sound
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."
$394 nightly
The price is $451
Aug 11 - Aug 12
Total includes taxes and fees
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, (233)
"We loved this B&B it was so quaint and beautiful. Loved our room and the breakfast. The staff was amazing! "
$279 nightly
The price is $319
Aug 14 - Aug 15
Total includes taxes and fees
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"
$341 nightly
The price is $390
Aug 27 - Aug 28
Total includes taxes and fees
The Inn at Yarmouth Port
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
Mulberry Bed & Breakfast
Surrounded by a beautiful garden, this charming bed and breakfast features a traditional pitched roof and a cozy chimney.

Mulberry Bed & Breakfast

2.5 star property
9.2 out of 10, Wonderful, (63)
"Restful stay, close to the beach & restaurants. Lovely breakfasts & kind host."
Mulberry Bed & Breakfast
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. "
$379 nightly
The price is $434
Sep 4 - Sep 5
Total includes taxes and fees
The Inn At Cape Cod
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"
$359 nightly
The price is $411
Sep 1 - Sep 2
Total includes taxes and fees
The Palmer House 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, (134)
"Stunning bed and breakfast. Amazing owners and a experience you won’t forget."
$341 nightly
The price is $390
Sep 4 - Sep 5
Total includes taxes and fees
Candleberry Inn on Cape Cod
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!"
$315 nightly
The price is $360
Aug 10 - Aug 11
Total includes taxes and fees
Isaiah Hall Bed & Breakfast Inn
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
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, (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."
$312 nightly
The price is $357
Sep 1 - Sep 2
Total includes taxes and fees
Inn on Main
Brewster by the Sea Inn
Enjoy a romantic meal under the stars with a beautifully set table and serene surroundings.

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. "
$336 nightly
The price is $384
Aug 28 - Aug 29
Total includes taxes and fees
Brewster by the Sea 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!"
$327 nightly
The price is $374
Aug 17 - Aug 18
Total includes taxes and fees
Liberty Hill 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, (247)
"The Old Manse Inn is amazing and everything they advertise! "
$326 nightly
The price is $373
Aug 26 - Aug 27
Total includes taxes and fees
The Old Manse Inn
Sea Street Inn
Relax in comfort with a large bed, television, and artwork in this stylish room.

Sea Street Inn

4.0 star property
10.0 out of 10, Exceptional, (41)
"Very nicely renovated small property with a fantastic breakfast."
$431 nightly
The price is $494
Aug 10 - Aug 11
Total includes taxes and fees
Sea Street 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
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
"Beautiful location. Clean, tidy, comfortable rooms. Excellent facilities. Good customer service with helpful and friendly staff. Very good breakfast options. Would recommend."
Steven Antony 7-night trip
Posted 9 hours ago
Bayside Resort Hotel

Frequently asked questions

What is the nightly rate for a Bed and Breakfast in Osterville?
Prices for B&Bs in Osterville often vary, but you can find a great deal from $217 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.
When is the best time to book a Bed & Breakfast in Osterville?
The best time to book a B&B in Osterville is during the summer months, particularly in July. This peak season attracts visitors seeking sunny days and vibrant coastal activities, with plenty of opportunities to enjoy the charming beaches and quaint local shops. Travelers will appreciate the lively atmosphere, as families and friends gather for outdoor picnics, boating, and leisurely strolls along the picturesque waterfront.

With average temperatures ranging from the mid-60s to the low 80s Fahrenheit, July offers a comfortable climate for outdoor adventures. Whether you're exploring the scenic Cape Cod National Seashore or indulging in fresh seafood at local eateries, the weather is great for making the most of your visit.

For those looking for a more budget-friendly option, consider planning your trip in October. This month features stunning fall foliage, providing a beautiful backdrop for walks along the coast or visits to nearby cranberry bogs. The serene ambiance and fewer crowds allow for a more relaxed experience while still enjoying the area's natural beauty.
What is the difference between a Osterville B&B 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.