Bed and Breakfast in Osterville

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

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

Featured B&B in Osterville

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 NZ$425
includes taxes & fees
18 Aug - 19 Aug
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, (220)
"Lovely little place. Great location!"
The price is NZ$884
includes taxes & fees
1 Sept - 2 Sept
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 NZ$364
includes taxes & fees
1 Sept - 2 Sept
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 NZ$709
includes taxes & fees
8 Sept - 9 Sept
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 NZ$798
includes taxes & fees
14 Aug - 15 Aug
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 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 Inn at Yarmouth Port
Belfry Inn & Bistro
3 bars/lounges

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
Front of property

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
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 NZ$728
includes taxes & fees
4 Sept - 5 Sept
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 NZ$689
includes taxes & fees
1 Sept - 2 Sept
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 NZ$655
includes taxes & fees
4 Sept - 5 Sept
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, (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 NZ$544
includes taxes & fees
12 Aug - 13 Aug
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 NZ$574
includes taxes & fees
12 Aug - 13 Aug
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 NZ$645
includes taxes & fees
28 Aug - 29 Aug
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 NZ$628
includes taxes & fees
17 Aug - 18 Aug
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 NZ$626
includes taxes & fees
26 Aug - 27 Aug
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 NZ$829
includes taxes & fees
11 Aug - 12 Aug
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.
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

Red Jacket Beach Resort

Red Jacket Beach Resort

10/10 Excellent
"The hotel is great, no complaints "
dennis 2-night trip
Posted 6 hours ago
Red Jacket Beach Resort

Frequently asked questions

Searching for B&Bs in Osterville?
If you're interested in something a little quirkier than the traditional hotel experience, a stay at a bed and breakfast might be the perfect option for your getaway. If you'd like to spend some time by the water during your time in Osterville, Cape Cod Beaches and Dowses Beach are worth a stop.
Why choose a B&B over a traditional hotel room?
With attentive service, opportunities to mingle with other guests and top-rated breakfasts, B&Bs all have a truly one-of-a-kind setting.
What are the best B&Bs in Osterville?
Here are some well-liked B&Bs in the area: The Christopher, The Edgartown Collection: 15 rooms. 17.8 mi (28.7 km) from the heart of Osterville. Enjoy the unique decor and patio area. Frederick William House: 5 rooms. 12.6 mi (20.3 km) from the city centre. Enjoy the deep-soaking baths and snack bar/deli. Inn on the Sound: 10 rooms. Situated 12.4 mi (20 km) from the heart of Osterville. Enjoy the free full breakfast and library. The Palmer House Inn: 17 rooms. 13.1 mi (21 km) from the city centre. Enjoy the free full breakfast and unique decor. An English Garden Bed & Breakfast: 11 rooms. Located 13.9 mi (22.3 km) from the core of Osterville. Enjoy the free full breakfast and patio area.
When should I book my B&B in Osterville?
When you're dreaming of a trip to Osterville, year-round temperatures and rainfall may be important factors to consider. The hottest months are usually August and July, with an average temperature of 20°C, while the coldest months are February and January, with an average of 3°C. Average annual precipitation for Osterville is 1328 mm.
What is there to do in Osterville?
Spend some time exploring Cape Cod Beaches and Dowses Beach if you're hoping to see some of the area's natural features. You should put Stand Up & Paddle Cape Cod and Public Beach on your list if you want to see more of the area.
How can I get to and around Osterville?
Planning your excursions in and around Osterville is easier with these transportation options. Fly into Hyannis, MA (HYA-Barnstable Municipal), which is located 5.8 mi (9.4 km) away from the heart of the city. You can also search for flights into Vineyard Haven, MA (MVY-Martha's Vineyard), which is 20.2 mi (32.5 km) away. If you'd like to venture out around the area, you may want to rent a car for your trip.