Search B&B in Osterville

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Check prices for these dates

Next weekend
8 Aug - 10 Aug
In two weeks
15 Aug - 17 Aug
In one month
29 Aug - 31 Aug
In two months
26 Sept - 28 Sept

Featured 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. "
The price is RM939
RM1,075 total
includes taxes & fees
26 Aug - 27 Aug
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 RM2,013
RM2,249 total
includes taxes & fees
1 Sept - 2 Sept
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 RM2,002
RM2,291 total
includes taxes & fees
11 Aug - 12 Aug
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 RM703
RM926 total
includes taxes & fees
1 Sept - 2 Sept
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, (53)
"Chose the property for a weekend getaway. Lovely place and very nice and friendly staff."
The price is RM2,035
RM2,469 total
includes taxes & fees
6 Aug - 7 Aug
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, (229)
"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
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)
"The property is so picturesque and idyllic. The staff greeted us so warmly every time we saw them. The food was really good and the chef really put her heart into it for it to taste so good. The staff is accommodating for dietary restrictions. My wife is gluten free so for breakfast, as well as the cookies they left for us in the room, it was all gluten free and so delicious. A great stay in Yarmouth. Will definitely come back and stay here if given the chance! "
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 RM1,202
RM1,376 total
includes taxes & fees
13 Aug - 14 Aug
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)
"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!"
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 RM1,789
RM2,047 total
includes taxes & fees
6 Aug - 7 Aug
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 RM1,331
RM1,524 total
includes taxes & fees
1 Sept - 2 Sept
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 RM1,532
RM1,753 total
includes taxes & fees
1 Sept - 2 Sept
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 RM1,329
RM1,521 total
includes taxes & fees
26 Aug - 27 Aug
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 RM1,823
RM2,086 total
includes taxes & fees
1 Sept - 2 Sept
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, (219)
"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 RM1,418
RM1,623 total
includes taxes & fees
1 Sept - 2 Sept
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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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. Inn on the Sound: 10 rooms. 12.4 mi (20 km) from the city centre. Enjoy the free full breakfast and library. Frederick William House: 5 rooms. Situated 12.6 mi (20.3 km) from the heart of Osterville. Enjoy the deep-soaking baths and snack bar/deli. 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.