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Check prices for these dates

Next weekend
Jul 4 - Jul 6
In two weeks
Jul 11 - Jul 13
In one month
Jul 25 - Jul 27
In two months
Aug 22 - Aug 24

Compare 77 B&B in Osterville with updated reviews, rates, and availability.

The Christopher, The Edgartown Collection
Front of property

The Christopher, The Edgartown Collection

3.0 star property
9.8 out of 10, Exceptional, (211)
"Lovely little place. Great location!"
$599 nightly
The price is $669
Jul 6 - Jul 7
Total includes taxes and fees
The Christopher, The Edgartown Collection
Frederick William House
Dining

Frederick William House

3.5 star property
9.6 out of 10, Exceptional, (265)
"Amazing place "
$279 nightly
The price is $319
Jul 1 - Jul 2
Total includes taxes and fees
Frederick William House
The Captain Farris House B&B
Exterior

The Captain Farris House B&B

3.5 star property
9.8 out of 10, Exceptional, (222)
"Great stay. B&B has a great location and the staff was very nice!"
$289 nightly
The price is $331
Jun 25 - Jun 26
Total includes taxes and fees
The Captain Farris House B&B
Inn on the Sound
Exterior

Inn on the Sound

3.5 star property
9.8 out of 10, Exceptional, (203)
"Beautiful location, comfort, quiet, restful, super food, extremely clean, yet very accessible to the coastal beauty and attractions."
$419 nightly
The price is $480
Jul 1 - Jul 2
Total includes taxes and fees
Inn on the Sound
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
An English Garden Bed & Breakfast
Terrace/patio

An English Garden Bed & Breakfast

3.0 star property
9.0 out of 10, Wonderful, (42)
"Great location, quaint b&b, nice owners."
$323 nightly
The price is $370
Jun 26 - Jun 27
Total includes taxes and fees
An English Garden Bed & Breakfast
Belfry Inn & Bistro
3 bars/lounges

Belfry Inn & Bistro

3.5 star property
9.0 out of 10, Wonderful, (184)
"Such a great little Inn for a quick weekend getaway. Three restaurants to chose from and great food at all. Chris and family were super friendly and accommodating . Loved it!"
$287 nightly
The price is $328
Jul 13 - Jul 14
Total includes taxes and fees
Belfry Inn & Bistro
Isaiah Hall Bed & Breakfast Inn
Front of property

Isaiah Hall Bed & Breakfast Inn

3.0 star property
9.8 out of 10, Exceptional, (116)
"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
Jun 25 - Jun 26
Total includes taxes and fees
Isaiah Hall Bed & Breakfast 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, (129)
"quaint inn"
$299 nightly
The price is $342
Jun 26 - Jun 27
Total includes taxes and fees
Candleberry Inn on Cape Cod
The Old Manse Inn
View from property

The Old Manse Inn

4.5 star property
9.8 out of 10, Exceptional, (243)
"Wonderful place... Brian and Charlie make you feel like you're at home. Breakfast was fantastic! Would highly recommend. "
$302 nightly
The price is $345
Jul 7 - Jul 8
Total includes taxes and fees
The Old Manse Inn
Winstead Beach Resort
Front of property

Winstead Beach Resort

4.0 star property
9.2 out of 10, Wonderful, (52)
"Chose the property for a weekend getaway. Lovely place and very nice and friendly staff."
$340 nightly
The price is $389
Jun 25 - Jun 26
Total includes taxes and fees
Winstead Beach Resort
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, (84)
"Beautiful property- spacious, well appointed room and wonderful breakfasts. The hosts were friendly and accessible. We had a wonderful stay and would definitely stay again "
The Inn At Cape Cod
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, (225)
"Amazing stay. Very respectful hosts. "
The Tern Inn Bed & Breakfast and Cottages
The Platinum Pebble Boutique Inn - Adults Only
BBQ/picnic area

The Platinum Pebble Boutique Inn - Adults Only

4.0 star property
9.8 out of 10, Exceptional, (18)
"Wonderful stay, could not recommend this B&B more! Great breakfast, beautiful room, perfect location."
The Platinum Pebble Boutique Inn - Adults Only
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 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
Long Dell Inn
Exterior

Long Dell Inn

3.5 star property
9.4 out of 10, Exceptional, (180)
"Great location and awesome breakfast’s "
$309 nightly
The price is $354
Jul 16 - Jul 17
Total includes taxes and fees
Long Dell 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."
$434 nightly
The price is $496
Jul 16 - Jul 17
Total includes taxes and fees
Inn on Main
Liberty Hill Inn
Normandy Room | Individually furnished, iron/ironing board, free WiFi, bed sheets

Liberty Hill Inn

3.5 star property
10.0 out of 10, Exceptional, (124)
"A superb property, a lovely room, delicious breakfasts, delightful hosts. Couldn’t be better."
$327 nightly
The price is $374
Jul 8 - Jul 9
Total includes taxes and fees
Liberty Hill 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. "
$420 nightly
The price is $481
Jul 15 - Jul 16
Total includes taxes and fees
Captain Freeman 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

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 $319 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.