A house by a lake with boats.

Bed and Breakfast in Osterville

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Check prices for these dates

Next weekend
30 Oct - 1 Nov
In two weeks
6 Nov - 8 Nov
In one month
20 Nov - 22 Nov
In two months
18 Dec - 20 Dec

Our top choices for Osterville bed & breakfast

A neatly arranged bedroom with a large bed, a bedside table, a chair, a TV mounted on the wall, and a window with blinds.

1. Sea Street Inn

Sea Street Inn
4.0 star property
Hyannis
9.8 out of 10, Exceptional, (47 reviews)
"Wonderful stay. Great communication. Outstanding breakfast."
United States
John
The price is NZ$531
includes taxes & fees
1 Nov - 2 Nov
Sea Street Inn
A window with a view of a house and trees, a vase with white roses, a stack of books, and a white mug on a small table.

2. The Village Inn Cape Cod

The Village Inn Cape Cod
3.5 star property
Yarmouth Port
10.0 out of 10, Exceptional, (233 reviews)
"Fantastic place!"
United States
Patti
The price is NZ$492
includes taxes & fees
9 Nov - 10 Nov
The Village Inn Cape Cod
A two-story house with a stone facade, a balcony, and a well-maintained garden.

3. Frederick William House

Frederick William House
3.5 star property
Falmouth
9.6 out of 10, Exceptional, (330 reviews)
"Loved the property and our room!"
United States
Kathy
The price is NZ$318
includes taxes & fees
1 Nov - 2 Nov
Frederick William House
A cozy room with wicker furniture, a stone fireplace, and a view of the ocean.

4. Inn on the Sound

Inn on the Sound
3.5 star property
Falmouth Heights
9.8 out of 10, Exceptional, (232 reviews)
"It was a great place to stay!"
United States
Dustin
The price is NZ$681
includes taxes & fees
25 Oct - 26 Oct
Inn on the Sound
A balcony with a view of a beach, a table with a vase of flowers, and a chair.

5. Winstead Beach Resort

Winstead Beach Resort
4.0 star property
Harwich Port
9.2 out of 10, Wonderful, (67 reviews)
"The whole stay including breakfast was fabulous"
United States
William
Winstead Beach Resort
A two-story house with a white picket fence, a blue door, and a porch with white railings.

6. An English Garden Bed & Breakfast

An English Garden Bed & Breakfast
3.0 star property
Dennis Port
9.0 out of 10, Wonderful, (102 reviews)
"Wonderful stay!"
United States
Donna M.
The price is NZ$437
includes taxes & fees
6 Nov - 7 Nov
An English Garden Bed & Breakfast
A large, two-story house with a grand entrance, large columns, and a balcony.

7. The Inn At Cape Cod

The Inn At Cape Cod
4.0 star property
Yarmouth Port
9.6 out of 10, Exceptional, (97 reviews)
"Amazing inn and the owners are great!"
United States
Harini
The Inn At Cape Cod
A bar area with shelves of liquor bottles, a wine cooler, and hanging wine glasses.

8. Belfry Inn & Bistro

Belfry Inn & Bistro
3.5 star property
Sandwich
9.2 out of 10, Wonderful, (217 reviews)
"We loved this place! The owner and staff were incredible and friendly. We stayed in the Barbi Suite and it was gorgeous. They had a nice breakfast as well. Will definitely go back again."
United States
Jennifer
The price is NZ$553
includes taxes & fees
25 Oct - 26 Oct
Belfry Inn & Bistro
A two-story house with a porch, surrounded by well-maintained gardens and trees.

9. The Captain Farris House B&B

The Captain Farris House B&B
3.5 star property
Bass River
9.8 out of 10, Exceptional, (283 reviews)
"We loved our stay at captain farris. Delicious breakfast, lovely staff that was so helpful and kind, and the comfiest bed we’ve ever slept in! 10/10."
United States
Ruth Ann
The price is NZ$507
includes taxes & fees
26 Oct - 27 Oct
The Captain Farris House B&B
An outdoor patio with a fire table, seating, and a table set for a meal.

10. The Palmer House Inn

The Palmer House Inn
3.5 star property
Falmouth
9.8 out of 10, Exceptional, (178 reviews)
"Quiet and charming B&B. The rooms are great, staff is nice and owners and their dog are great! Walking distance to the Main Street with coffee, restaurants and shops. We stayed a few days with a quick day trip to Martha’s (which we walked to the ferry)"
United States
Jordi
The price is NZ$504
includes taxes & fees
1 Nov - 2 Nov
The Palmer House Inn
A two-story house with a porch, a star decoration, and outdoor seating.

11. Sea Meadow Inn

Sea Meadow Inn
4.0 star property
Brewster
10.0 out of 10, Exceptional, (27 reviews)
"We've been traveling to the Cape for almost 40 years, and this is by far the best B&B we've visited. The rooms and property are lovely, the food is excellent, and the owers are welcoming."
United States
Joanne
The price is NZ$488
includes taxes & fees
26 Oct - 27 Oct
Sea Meadow Inn
A waterfront property with multiple buildings, including a large central structure with a covered porch, smaller adjacent buildings, and a beach area.

12. The Park View ROOM INSIDE "The Flamingo Social House"

The Park View ROOM INSIDE "The Flamingo Social House"
Cape Cod
2.0 out of 10, (2 reviews)
"Not at all what the pictures and . The bed took up the entire bedroom, and there was no place to move there. The bathroom is apparently a shared bathroom, which was not mentioned. There was a bunch of debris in the room as well."
United States
Mark
The price is NZ$382
includes taxes & fees
25 Oct - 26 Oct
The Park View ROOM INSIDE "The Flamingo Social House"
A pathway flanked by vibrant flowers and greenery, leading to a house with large windows.

13. The Villa Callo Inn

The Villa Callo Inn
3.0 star property
West Harwich
9.6 out of 10, Exceptional, (8 reviews)
"Really enjoyed our stay. Staff went above and beyond, breakfast was top notch and the Location was great."
United States
Shawn
The price is NZ$919
includes taxes & fees
24 Nov - 25 Nov
The Villa Callo Inn
A table set with plates, glasses, a mug, and a blue hydrangea.

14. Brewster by the Sea Inn

Brewster by the Sea Inn
4.0 star property
West Brewster
9.8 out of 10, Exceptional, (176 reviews)
"Angela was amazing and professional. I would highly recommend to anyone staying at Chatham Bars, Wequassett, or Ocean Edge to give this a visit…"
United States
louis
The price is NZ$610
includes taxes & fees
5 Nov - 6 Nov
Brewster by the Sea Inn
A two-story house with a symmetrical facade, a central entrance, and a flag.

15. Candleberry Inn on Cape Cod

Candleberry Inn on Cape Cod
4.5 star property
Brewster
10.0 out of 10, Exceptional, (152 reviews)
"The hotel is amazing. Terrific breakfast, beautiful rooms and top notch service."
United States
Dvir
The price is NZ$609
includes taxes & fees
26 Oct - 27 Oct
Candleberry Inn on Cape Cod
A historic building with a sign reading "Isaiah Hall Inn" and the year "1857" on the front.

16. Isaiah Hall Bed & Breakfast Inn

Isaiah Hall Bed & Breakfast Inn
3.0 star property
Dennis
9.6 out of 10, Exceptional, (130 reviews)
"Staff, stay, location...experience was very very nice!"
United States
Matthew
Isaiah Hall Bed & Breakfast Inn
A beach with a sunset, calm water, and rocks.

17. The Old Manse Inn

The Old Manse Inn
4.5 star property
Brewster
9.8 out of 10, Exceptional, (255 reviews)
"I highly recommend Old Manse Inn. It is charming, welcoming and every detail is accounted for. The innkeepers are very friendly and kind - and make a delicious breakfast!"
United States
Shannon
The price is NZ$523
includes taxes & fees
1 Nov - 2 Nov
The Old Manse Inn
Front of property – evening/night

18. The Christopher, The Edgartown Collection

The Christopher, The Edgartown Collection
3.0 star property
Edgartown
9.8 out of 10, Exceptional, (288 reviews)
"Friendly and helpful staff - super great location."
United States
Clayton
The Christopher, The Edgartown Collection
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

Inn on the Square

Inn on the Square

8/10 Good
"We enjoyed having a glass of wine by the fire pit in the courtyard area, and the adjoining restaurant for breakfast. Our primary interest was proximity to the Shining Sea Bikeway which was just a block away. Easy stroll to the downtown area with lots of shops and restaurants. We did not use the indoor pool as it was crowded with families which wasn’t our vibe but they were obviously having a great time on a rainy night. Free parking a plus. We would stay here again."
Laura 2-night trip
Posted 10 hours ago
Inn on the Square

Find out more about Osterville

Osterville B&B information

Number of reviews
2,009
Accommodation
45 B&B
Lowest Price
NZ$318
Highest Price
NZ$919

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: An English Garden Bed & Breakfast: 11 rooms. 13.9 mi (22.3 km) from the heart of Osterville. Enjoy the free full breakfast and patio area. The Christopher, The Edgartown Collection: 15 rooms. 17.8 mi (28.7 km) from the city centre. Enjoy the unique decor and patio area. The Captain Farris House B&B: 10 rooms. Situated 10.7 mi (17.2 km) from the heart of Osterville. Enjoy the free full breakfast and designer toiletries. Belfry Inn & Bistro: 16 rooms. 10.6 mi (17 km) from the city centre. Enjoy the on-site dining and bars. Inn on the Sound: 10 rooms. Located 12.4 mi (20 km) from the core of Osterville. Enjoy the free full breakfast and library.
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.

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