Find a Bed and Breakfast in Oak Bluffs

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Find properties with these dates

Tonight
May 10 - May 11
Tomorrow
May 11 - May 12
This weekend
May 10 - May 12

Browse Select Oak Bluffs B&B

Luxury King Room
Sea Street Inn
4.0 star property
10.0 out of 10, Exceptional, (34)
"Beautiful property owner very accommodating. The only negative the detergent they used had a terrible scent. They should use sent free."
The price is CA $377
CA $432 total
includes taxes & fees
May 16 - May 17
Sea Street Inn
Garden
Captain David Kelley House Bed & Breakfast
3.5 star property
10.0 out of 10, Exceptional, (32)
"Are stay was amazing we had such a great time."
Captain David Kelley House Bed & Breakfast
Exterior
Woods Hole Inn
3.5 star property
10.0 out of 10, Exceptional, (1)
"So welcoming and felt like home. From warm breakfast and great coffee, to super comfortable bed and a great nights sleep. Staff was absolutely friendly and helpful in answering our questions and giving guidance and recommendations for our trip into Martha’s Vineyard. I’m sure we’ll be back! "
Woods Hole Inn
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Lobby sitting area
The Christopher, The Edgartown Collection
3.0 star property
9.8 out of 10, Exceptional, (149)
"The Christopher is in the heart of Edgartown…Ellen is so personable and professional! The property and our room were beautiful! I highly recommend this Inn… "
The price is CA $394
CA $432 total
includes taxes & fees
May 12 - May 13
The Christopher, The Edgartown Collection
Exterior
Inn on the Sound
3.5 star property
9.8 out of 10, Exceptional, (165)
"We had a lovely stay at Inn on the Sound! The owners went above and beyond to make our stay memorable and even surprised up with a room upgrade! Being on the ocean is glorious - having coffee from a balcony room overlooking the ocean is idyllic. Breakfast at the inn was delicious. The location is perfect- right on the water, so you have easy access to the beach as well as the shining sea bike trail. It’s also very close to town so getting to dinner was a very quick commute. Highly recommend...
The price is CA $422
CA $484 total
includes taxes & fees
May 12 - May 13
Inn on the Sound
Beach nearby
Frederick William House
3.5 star property
9.6 out of 10, Exceptional, (212)
"Jeanette is a wonderful host. Friendly and welcoming. Delicious continental breakfast. Beautiful rooms. The room had a gas fireplace as well as a skylight in the bathroom. Close to downtown and the ferry. Looking forward to returning there again. "
The price is CA $233
CA $266 total
includes taxes & fees
May 12 - May 13
Frederick William House
Porch
The Palmer House Inn
3.5 star property
9.6 out of 10, Exceptional, (152)
"Beautiful property, great weekend stay. "
The price is CA $338
CA $387 total
includes taxes & fees
May 12 - May 13
The Palmer House Inn
Exterior
Wood Duck Inn
3.0 star property
9.6 out of 10, Exceptional, (5)
"The Innkeeper was a gem! The place needs a very good cleaning and I would rent a car the next time I stay there. You are about 2-3 miles from any restaurants, groceries etc"
Wood Duck Inn
Exterior
Long Dell Inn
3.5 star property
9.4 out of 10, Exceptional, (177)
"Wonderful hosts! Offered everything to their guests to feel welcomed and comfortable. We stayed in The Captains Room. Excellent sheets!! Centrally located between Osterville and Hyannis. Centerville is a beautiful little town. A great stay. "
The price is CA $286
CA $327 total
includes taxes & fees
May 15 - May 16
Long Dell Inn
Exterior
Narragansett House
2.5 star property
8.8 out of 10, Excellent, (47)
"very clean and very helpful staff. breakfast only continental not very good for celiacs. stairs not good for older people"
Narragansett House
Beach nearby
Captain Lawrence Inn
3.5 star property
8.8 out of 10, Excellent, (64)
"We arrived at the inn at 5pm and were told there was no electricity due to the storm the day before. The power had been off for 14 hours at that time. We came back after dinner and there was still no power. I'm sympathetic to their plight, but If the owners had told us about this many hours sooner we would have had time to find another place to stay, but by then we stopped at two places that were fully booked and finally decided to drive back to our home in Boston."
Captain Lawrence Inn
Children's area
The 1720 House
2.5 star property
6.8 out of 10, (41)
"Overpriced dirty rundown great location"
The 1720 House
Aerial view
Simmons Homestead Inn
3.5 star property
6.6 out of 10, (15)
"Innkeeper-of-sorts Bill is the sort of host all innkeepers and hoteliers should aspire to be. Encyclopedically knowledgeable about all things Hyannis AND Cape Cod, he provides invaluable guidance on how to best spend one’s time. The setting is also superb, in a quiet enclave away from the teeming town."
Simmons Homestead Inn
Deluxe Single Room
The Dexter
3.0 star property
The Dexter
Fridge, microwave, oven, stovetop
welcome home with pool in centerville!
welcome home with pool in centerville!
Deluxe Room, 1 King Bed
Crocker Inn
3.0 star property
Crocker Inn
Free daily self-serve breakfast
The Little B&B in Aquinnah
2.0 star property
The Little B&B in Aquinnah
Don't see what you're looking for?
See all available properties in Oak Bluffs
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.

Other property types in Oak Bluffs

Interior
Walking Distance From Oak Bluffs Ferry Terminal With 180 Degree Ocean View.
9.8 out of 10, Exceptional, (69)
"The apartment was spotless! Open and airy. The host left excellent instructions, and a phone number if needed. We did and he responded immediately and problem resolved. I have only one suggestion. You need more than one mirror It’s located in the bathroom. Need another either in hall or bedroom I would recommend this apartment to anyone"
The price is CA $581
CA $951 total
includes taxes & fees
May 12 - May 13
Walking Distance From Oak Bluffs Ferry Terminal With 180 Degree Ocean View.
Iron/ironing board, WiFi, bed sheets
Romantic seaside getaway with pool & tennis courts - dog-friendly
9.8 out of 10, Exceptional, (36)
"Great location, lots of amenities - pool, fire pits, tennis courts, nearby restaurant. Communication for checking was excellent."
Romantic seaside getaway with pool & tennis courts - dog-friendly
Property grounds
Luxury home with private pool & foosball - near 3 towns & many beaches
8.6 out of 10, Excellent, (30)
"I recently stayed in this lovely OB home with my family. It was me and 9 other people, and there was plenty of room for everyone. The photos are accurate. The pool was clean and heated. The house is located in a private, wooded area but conveniently located to OB, Edgartown, the airport and beaches. The interior/furniture were so cozy. The house came equipped with enough plates, dishes, pots, pans, utensil, towels, etc. It would be helpful if the house came with a book of instructions, so we'd...
Luxury home with private pool & foosball - near 3 towns & many beaches
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.

Frequently asked questions

Searching for B&Bs in Oak Bluffs?
Whether you’re traveling with your family and want a friendly place to stay, or you’re a solo traveler hoping to make some connections, B&Bs can be a great choice for many travelers. During your time in Oak Bluffs, you might want to spend some time strolling along the water at Oak Bluffs Town Beach and Inkwell Beach.
How do you know if a B&B is the right choice for you?
Every B&B has a unique charm. Whether it’s a picturesque garden or a sunlit breakfast nook, the tiny details are what make bed and breakfasts a fun place to get away.
What are the best B&Bs in Oak Bluffs?
Below are some well-liked B&Bs in the surrounding area: Narragansett House: 19 rooms. 0.2 mi (0.4 km) from the heart of Oak Bluffs. Enjoy the local cuisine breakfast and deli. Frederick William House: 6 rooms. 8.4 mi (13.5 km) from the downtown core. Enjoy the soaking bathtubs and deli. The Christopher, The Edgartown Collection: 15 rooms. Situated 5.2 mi (8.3 km) from the heart of Oak Bluffs. Enjoy the unique décor and patio area. Inn on the Sound: 10 rooms. 6.5 mi (10.4 km) from the heart of downtown. Enjoy the free full breakfast and library. The Palmer House Inn: 17 rooms. Located 7.6 mi (12.3 km) from the core of Oak Bluffs. Enjoy the free full breakfast and unique décor.
When should I stay at a B&B in Oak Bluffs?
When you’re planning your trip to Oak Bluffs, be sure to take into account the year-round temperatures. The hottest months are usually August and July with an average temp of 68°F, while the coldest months are February and January with an average of 38°F. Average annual precipitation for Oak Bluffs is 47 inches.
What is there to do in Oak Bluffs?
Travelers enjoy Oak Bluffs for its wineries and shopping. When you want to spend some time in the great outdoors, Oak Bluffs Town Beach and Inkwell Beach are some notable spots. You might put Circuit Avenue and Oak Bluffs Harbor on your list if you want to see more of the area.
How can I get to and around Oak Bluffs?
You can map out your trip in and around Oak Bluffs ahead of time with these transportation options. Fly into Vineyard Haven, MA (MVY-Martha’s Vineyard), which is located 5.2 mi (8.3 km) away from the heart of the city. Otherwise, look for flights into Hyannis, MA (HYA-Barnstable Municipal), which is 20.5 mi (32.9 km) away. If you’d like to explore around the area, you may want a rental car for your journey.