Book Osterville Bed & Breakfast

Start date: Check-in selected.
To Date
End date: Check-out
    bundle and save illustration

    Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals
    one key illustration

    OneKeyCash

    Earn OneKeyCash on all your eligible bookings
    ftc illustration

    Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

Next weekend
Oct 3 - Oct 5
In two weeks
Oct 10 - Oct 12
In one month
Oct 24 - Oct 26
In two months
Nov 21 - Nov 23

B&B in Osterville

The Christopher, The Edgartown Collection
Front of property

The Christopher, The Edgartown Collection

3.0 star property
9.8 out of 10, Exceptional, (235)
"Great location, fantastic room, friendly staff and local dining options"
$277 nightly
The price is $310
Oct 23 - Oct 24
Total with 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, (288)
"Jeanette was great. Continental breakfast was excellent. Enjoyed the free bikes with the convenient trail behind the property. "
$208 nightly
The price is $238
Oct 13 - Oct 14
Total with 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, (244)
"beautiful property in a great location! the breakfast was delicious everyday! we would definitely come back! "
$211 nightly
The price is $241
Oct 19 - Oct 20
Total with taxes and fees
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, (56)
"A charming hotel a block away from a nice sandy beach, loved a stay there."
$190 nightly
The price is $217
Oct 12 - Oct 13
Total with taxes and fees
An English Garden Bed & Breakfast
Sea Meadow Inn
Exterior

Sea Meadow Inn

3.5 star property
10.0 out of 10, Exceptional, (8)
"Wonderful stay! Great breakfast options with kitchen made fresh savory/sweet breakfast."
$233 nightly
The price is $267
Sep 29 - Sep 30
Total with taxes and fees
Sea Meadow Inn
Inn on the Sound
Exterior

Inn on the Sound

3.5 star property
9.8 out of 10, Exceptional, (209)
"Quiet, charming, nice breakfast, right across from beach"
$269 nightly
The price is $308
Sep 28 - Sep 29
Total with taxes and fees
Inn on the Sound
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, (89)
"I thought the property was one of the best on the Cape having stayed in many. Service was great and room was wonderful."
$346 nightly
The price is $396
Sep 28 - Sep 29
Total with taxes and fees
The Inn At Cape Cod
Inn on Main
Outdoor dining

Inn on Main

3.5 star property
10.0 out of 10, Exceptional, (71)
"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."
$299 nightly
The price is $342
Oct 12 - Oct 13
Total with taxes and fees
Inn on Main
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, (139)
"Stunning bed and breakfast. Amazing owners and a experience you won’t forget."
$368 nightly
The price is $421
Sep 28 - Sep 29
Total with taxes and fees
Candleberry Inn on Cape Cod
Mulberry Bed & Breakfast
Front of property

Mulberry Bed & Breakfast

2.5 star property
9.2 out of 10, Wonderful, (68)
"We like the host, Frances. She was nice and incredibly kind, and made me feel right at home when we arrived. We loved the homemade breakfast."
Mulberry Bed & Breakfast
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, (229)
"Amazing stay. Very respectful hosts. "
The Tern Inn Bed & Breakfast and Cottages
The Inn at Yarmouth Port
View from room

The Inn at Yarmouth Port

4.0 star property
9.6 out of 10, Exceptional, (119)
"We liked everything, the hosts were amazing and helpful, breakfasts top-notch, great climate control in the room, modern comfort in historic setting"
$359 nightly
The price is $411
Sep 28 - Sep 29
Total with taxes and fees
The Inn at Yarmouth Port
Belfry Inn & Bistro
3 bars/lounges

Belfry Inn & Bistro

3.5 star property
9.0 out of 10, Wonderful, (189)
"Our first time in the sandwich area for our anniversary. Room was adorable and a beautiful area for walking around to the views, food and shopping"
Belfry Inn & Bistro
Winstead Beach Resort
Front of property

Winstead Beach Resort

4.0 star property
9.2 out of 10, Wonderful, (59)
"Very nice hotel, staff. Great location for relaxing visit to the mountains. "
$231 nightly
The price is $264
Sep 29 - Sep 30
Total with taxes and fees
Winstead Beach Resort
The Palmer House Inn
Beach nearby

The Palmer House Inn

3.5 star property
9.6 out of 10, Exceptional, (175)
"Nice place to stay"
$311 nightly
The price is $356
Oct 12 - Oct 13
Total with taxes and fees
The Palmer House Inn
Isaiah Hall Bed & Breakfast Inn
Front of property

Isaiah Hall Bed & Breakfast Inn

3.0 star property
9.6 out of 10, Exceptional, (122)
"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!"
$315 nightly
The price is $360
Sep 28 - Sep 29
Total with taxes and fees
Isaiah Hall Bed & Breakfast Inn
The Old Manse Inn
View from property

The Old Manse Inn

4.5 star property
9.8 out of 10, Exceptional, (250)
"The Old Manse Inn is amazing and everything they advertise! "
$281 nightly
The price is $321
Oct 5 - Oct 6
Total with taxes and fees
The Old Manse Inn
The Village Inn Cape Cod
Garden

The Village Inn Cape Cod

3.5 star property
10.0 out of 10, Exceptional, (221)
"Jennifer is a wonderful host! Breakfast on the back porch was delicious and a great start to the day. Rooms are comfortable and the back of the house where we were was, is quiet. Highly recommend. "
The Village Inn Cape Cod
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, (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
Oct 14 - Oct 15
Total with taxes and fees
Liberty Hill Inn
Sea Street Inn
Luxury King Room | Egyptian cotton sheets, premium bedding, individually decorated

Sea Street Inn

4.0 star property
9.8 out of 10, Exceptional, (45)
"Very nicely renovated small property with a fantastic breakfast."
$259 nightly
The price is $296
Oct 26 - Oct 27
Total with taxes and fees
Sea Street 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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Osterville Hotel Reviews

Aiden by Best Western Cape Cod - West Yarmouth

Aiden by Best Western Cape Cod - West Yarmouth

10/10 Excellent
"I have stayed here before and looks like they have done some renovations to the property. nice and clean and very comfortable"
stephen 2-night trip
Posted 1 day ago
Aiden by Best Western Cape Cod - West Yarmouth

Find out more about Osterville

Find out more about Osterville

Osterville B&B information

Number of reviews
2,858
Accommodation
46 B&B
Lowest Price
$217
Highest Price
$421

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.

Explore a world of travel with Expedia

Explore a world of travel with Expedia