Bed and breakfast vacation rentals in Oak Bluffs

Find and book unique bed and breakfast rentals on Airbnb

Top-rated bed and breakfast rentals in Oak Bluffs

Guests agree: these bed and breakfast rentals are highly rated for location, cleanliness, and more.

0 of 0 items showing

1 of 3 pages

Superhost

Hotel room in Falmouth

4.85 out of 5 average rating, 47 reviews

Luxury SeaSide King Suite, Frederick William House

DonnaRating, 5 stars6 months ago

We stayed a few nights and the inn was quaint and cozy. Perfectly located to restaurants and shops. Our host Jeanette was friendly and very helpful. The continental breakfast was served in the cutest dining area and her homade coffee cake was delicious.

Top guest favorite

Private room in North Falmouth

4.91 out of 5 average rating, 235 reviews

North Falmouth Suite 'downstairs suite'

AlineRating, 5 stars9 months ago

We stayed at Wiz's place for 3 nights and felt right at home! Our stay was super pleasant, there are a lot of things to do in the area and we could have stayed a lot longer. The breakfast was such a nice little touch and the homemade goodies were very much appreciated! Thanks again for everything!!

A well-maintained garden is visible beside a shingled exterior of the property. Rounded shrubs and vibrant flowers add color and texture. Steps lead up to an entrance accented by lush greenery, providing a welcoming transition into the home.

Private room in West Tisbury

4.89 out of 5 average rating, 27 reviews

Bright, Unique on Martha's Vineyard!

DanRating, 5 stars11 months ago

Marjory is the kindest, most thoughtful host. And the studio is perfect. Quiet, and surrounded by the most peaceful West Tisbury meadows. It’s the ideal launching place for up island explorations, days at Lamberts Cove, and just generally relaxing and getting into that deep calm of rural Vineyard vibes. I’ll be back!

Guest favorite

A spacious screened porch features comfortable seating on wrought iron furniture with floral cushions. A small round table is set against the wall, while a flat surface transitions to a wooden deck visible through large screens. Soft natural light filters through the space.

Private room in North Falmouth

4.81 out of 5 average rating, 653 reviews

Cape Cod Cottage

The space is available for one to four guests in the same party. Accommodations are in a separate wing of the house. There are two bedrooms, one with a double bed and one with twin beds. There is a private bath as well as a sitting room and screen porch for the exclusive use of the guest. The house is within walking distance to a private ocean beach and within a mile of the Shinning Sea Bike Path (bike rentals are available nearby). Numerous restaurants serving traditional Cape fare are within a two mile radius, with many more in nearby Falmouth and Woods Hole. Breakfast is provided.

Superhost

Two wooden adirondack chairs are positioned in a sandy corner, surrounded by a wooden fence and tall greenery. A potted plant with red flowers sits on a small table between the chairs, creating a peaceful outdoor seating area.

Private room in Oak Bluffs

4.88 out of 5 average rating, 74 reviews

Oak Bluffs/In Town/ Harbor Views/ Queen Bed

Welcome to Watchaboat! Our family home has a comfortable, clean room available. The room has a beachy cottage feel where you'll be happy to rest at the end of a summer day. We've got a great location, overlooking Oak Bluffs harbor, a 9-minute walk to downtown OB & a quick stroll to Oak Bluffs Town Beach (.3 mile). Our bustling home has a busy business on the property, so it's fit for travelers who need to drop their bags & go enjoy the island. Please read the listing carefully before booking!

Lush greenery surrounds the historic inn, featuring mature trees and vibrant shrubs. The garden area showcases well-maintained plants, creating a serene outdoor space. The white exterior of the inn is visible in the background, harmonizing with the natural landscape.

Private room in Fairhaven

4.97 out of 5 average rating, 30 reviews

Warren Delano Room at the Delano Homestead B&B

Comfortable, historic inn located in the village center of a classic seaport. Walk to restaurants, fishing piers, bike path, beach, shopping. Short drive to museums, ferries, beaches, cape, Newport, Boston, etc. Breakfast included. One large room with a king-sized bed and private bath. The bath is a few feet away in private area and we provide robes. But, if you want two rooms and are comfortable sharing the bath, please let us know and we can give you a price for two rooms with shared bath.

The entrance of Kathleen's Kottage is surrounded by verdant greenery and colorful flower arrangements. A well-maintained gravel pathway leads to a welcoming porch, featuring white railings and potted plants. The cottage displays a charming shingle exterior, highlighting the friendly character of the residence.

Private room in Oak Bluffs

5 out of 5 average rating, 26 reviews

The Mary Suite - in Oak Bluffs MV

Kathleen Nasser is the owner of Kathleen's Kottage, a seasonal Host Home located in Oak Bluffs, MA. This is the Mary Suite the most private and spacious room. The suite is located on the second floor of the building adjacent to the main house. The suite has a private entrance with a lockable door. King size bed. Private bath with dual sinks. Sitting room. Cable TV, AC and Internet. Microwave, Refrigerator and Coffeemaker. Serving a light fare breakfast. We are small Pet Friendly.*

Superhost

A bright guest room features a spacious bed adorned with a textured white coverlet. Large windows invite ample natural light, complemented by a cozy window seat with decorative pillows. Floral accents enhance the room's charm. Warm tones and traditional decor create a welcoming atmosphere.

Private room in Barnstable

4.91 out of 5 average rating, 91 reviews

Retreat to Cape Cod Home on Water

Private home built in 1906. Two lovely guest rooms in an ideally Cape Cod home overlooking Nantucket Sound and the Centerville and Bumps rivers. Both rooms have window seats and provide a traditional New England style. You will love the proximity to the ferries, P-Town, Woods Hole, great beaches, lakes, restaurants, theaters, shopping and whale watching. Both rooms have AC. Sorry to say, but my listing is not suitable for children under the age of 12; because of stairs and dock.

Top guest favorite

A welcoming front porch is lined with columns and features hanging flower pots. Comfortable seating arrangements are provided, including chairs and a small table. Lush greenery surrounds the porch, enhancing the inviting outdoor space.

Private room in Falmouth

4.96 out of 5 average rating, 250 reviews

Secret Garden Suite with full breakfast

We built our home in 1997 and have shared it with our five children, grandchildren and extended family. We thought someday when the kids leave, we will make it into a Bed & Breakfast and Airbnb has made the dream simply possible. Joining Airbnb in May 2016 changed and enriched our lives by the many travelers we have hosted and friends we have made. We look forward to being your host soon. We believe that the breakfast we include with the room rate adds substantial value.

Guest favorite

A welcoming front porch is shown, featuring a series of wooden rocking chairs positioned against a backdrop of shingled siding. The stairs lead down to a well-manicured yard with newly planted flowering shrubs, framed by a neatly covered foundation.

Private room in West Tisbury

4.97 out of 5 average rating, 30 reviews

warm and spacious B and B in our Martha's Vin home

Quintessential vineyard beach house set among woods, farms, and wildlife sanctuaries. This recently built, sunny West Tisbury B and B is minutes away from beaches, including coveted Lambert's Cove beach. Sink into a comfy queen bed after a day of fun, and enjoy private bath, laundry room and separate entrance. Awake to singing birds, then explore our island after starting your day with steaming coffee/tea and pastries which can be enjoyed on the spacious front porch.

Vacation rentals for every style

Get the amount of space that is right for you

Apartments

Convenient locations with everyday essentials

Houses

A space thats all yours, with room for everyone

Hotels

Stylish accommodations and amenities

Popular amenities for Oak Bluffs bed and breakfast rentals

Kitchen

Wifi

Free parking on premises

Air conditioning

Family-friendly bed and breakfast rentals

A bright room is featured, including a queen bed with a plaid blanket and a nearby futon. A dresser is positioned against the wall, accompanied by a table lamp. Artwork decorates the walls, and natural light filters through the windows, illuminating the wooden flooring.

Private room in West Tisbury

4.89 out of 5 average rating, 27 reviews

Bright, Unique on Martha's Vineyard!

DanRating, 5 stars11 months ago

Marjory is the kindest, most thoughtful host. And the studio is perfect. Quiet, and surrounded by the most peaceful West Tisbury meadows. It’s the ideal launching place for up island explorations, days at Lamberts Cove, and just generally relaxing and getting into that deep calm of rural Vineyard vibes. I’ll be back!

Superhost

A cozy bed is dressed with neutral linens and a striped blanket. A decorative pillow featuring floral motifs adds a touch of charm. A bedside lamp and a white dresser are visible, complemented by a vintage sign reading 'Nantucket Beach Haven' on the wall.

Hotel room in Falmouth

4.85 out of 5 average rating, 47 reviews

Luxury SeaSide King Suite, Frederick William House

DonnaRating, 5 stars6 months ago

We stayed a few nights and the inn was quaint and cozy. Perfectly located to restaurants and shops. Our host Jeanette was friendly and very helpful. The continental breakfast was served in the cutest dining area and her homade coffee cake was delicious.

Guest favorite

A cozy bedroom features a queen-sized bed with a light-colored quilt and decorative pillows. Natural light enters through a small window, illuminating a vintage dresser and a small desk with a chair in the corner. A standing fan and air conditioning unit provide comfort.

Private room in Fairhaven

5 out of 5 average rating, 30 reviews

Franklin Delano Room at the Delano Homestead B&B

MichelleRating, 5 stars2 months ago

Paul’s place is like a museum! So much history and he takes great pride in it! Tracey met us and gave us all the important info we needed! We got settled in and felt right at home. The bed was so comfortable and the newly refinished bathroom was large with a shower that had great pressure. The breakfast the next morning, wow! It was perfection! Thank you Tracey and Paul! We will definitely be back!

Guest favorite

A light-filled bedroom is equipped with a queen-sized bed, dressed in floral-patterned bedding, and a decorative bolster pillow. A wicker rocking chair is positioned nearby, holding a colorful blanket and folded towel. Potted flowers adorn the windowsill, complementing the hardwood flooring.

Private room in Teaticket

4.9 out of 5 average rating, 198 reviews

Two bedroom suite in Falmouth MA! Muffins too!

ShelbyRating, 5 stars1 week ago

We had the best stay! It was so cozy and clean and clear instructions all around the air BnB for the amenities. It’s a beautiful home close to the beach it a quiet charming neighborhood. 11/10 recommend!

The image features a well-maintained swimming pool surrounded by lounge chairs, offering ample seating. The two-story buildings in the background have multiple entrances, greenery is present around the area, and the space is enclosed with a white fence.

Hotel room in Teaticket

4.62 out of 5 average rating, 60 reviews

Courtyard Room

MichaelRating, 5 stars11 months ago

amazing host and location. Very communicative when we had a small hiccup due to the time I had to be at a wedding. They took care of the situation quickly

Top guest favorite

The exterior of a historic home is displayed, showcasing a well-maintained white facade with black shutters. Lush greenery surrounds the property, including colorful flowers and shrubs, along with trees providing shade. A lamp post stands to the left of the home, enhancing the inviting setting.

Private room in North Falmouth

4.91 out of 5 average rating, 235 reviews

North Falmouth Suite 'downstairs suite'

AlineRating, 5 stars9 months ago

We stayed at Wiz's place for 3 nights and felt right at home! Our stay was super pleasant, there are a lot of things to do in the area and we could have stayed a lot longer. The breakfast was such a nice little touch and the homemade goodies were very much appreciated! Thanks again for everything!!

Guest favorite

A soft, inviting bedroom is highlighted by a spacious bed dressed in white linens. Two decorative lamps with ornate bases sit on either side of the bed, illuminating plush pink pillows against a light-hued headboard. A framed mirror above the bed reflects natural light.

Hotel room in Falmouth

4.92 out of 5 average rating, 71 reviews

Park Side Queen Room @ Frederick William House

PatriciaRating, 5 stars2 months ago

Absolutely love our stay! The white room was beautiful and exactly as described! The bed was extremely comfortable and I loved the lounging chair for reading. The outside balcony was wonderful to sit on. The bike/walking bath was very accessible and provided a great afternoon of walking. The Knob recommendation was breath taking! Thank you for your morning conversations and getting to know you!! Definitely would recommend this bed and breakfast!

Show all

Bed and breakfast rentals with breakfast

A charming bungalow features a covered front porch with white railings, surrounded by well-maintained gardens. Planters with colorful flowers are positioned along the gravel walkway leading to the entrance. Lush greenery lines the sides, creating a welcoming atmosphere.

Private room in Oak Bluffs

5 out of 5 average rating, 21 reviews

The Millie Suite - in Oak Bluffs MV

DavidRating, 5 starstoday

Kathleen & Frank were very friendly hosts. Kathleen provided all the amenities and a wonderful homemade breakfast each morning. The yard and home were very welcoming. The plantings, flowers and peaceful backyard was lovely. We would definitely return again to Kathleen’s cottage.

A sandy beach stretches along the shoreline, with gentle waves lapping at the shore. In the distance, a beach house is visible against a pastel sunset sky, while scattered rocks line the water's edge.

Private room in East Falmouth

5 out of 5 average rating, 4 reviews

Peace & Plenty 3 Falmouth: Private Beaches, Tennis

VenusRating, 5 stars34 months ago

Beautiful beach house with access to a private beach, kayaks, and the backyard. perfect for enjoying some time on the property and also touring around Falmouth and making a day trip at Martha's Vineyard. Lisa is a very warm and friendly host. You'll have a wonderful stay here!

Superhost

A compact bathroom corner features a wall-mounted sink with a modern faucet. A round mirror is positioned above the sink, while neatly hung towels are displayed on a bar. Light blue walls complement the sleek design of the space.

Private room in Woods Hole

5 out of 5 average rating, 14 reviews

Charming King Room - Woods Hole Inn

AndreaRating, 5 stars1 month ago

Charming, clean, comfortable. Great location one block from the ferry to Martha’s Vineyard and lots of shops and restaurants in town. The hosts went out of their way to help me arrange a shuttle from airport and even offered to buy a sandwich and leave it in my room since I would be arriving after all the restaurants were closed. Wonderful, very ample breakfast with lots of variety- quiche, granola, fruit, toast etc. served in the morning. The other guest were very friendly and enjoyed sharing notes on their travels. Highly recommended!

A clear glass tray is arranged on a wooden surface, displaying eight miniature bottles of toiletries. Each bottle is labeled with product names, including body lotion, conditioner, shampoo, and shower gel, all presented in uniform sizes for easy access.

Private room in Fairhaven

4.73 out of 5 average rating, 15 reviews

The Sara Delano Room at the Delano Homestead B&B

StaceyRating, 5 stars11 months ago

We had a great time! Loved the antique furniture, all the rich history. Our host (Paul) and innkeeper (Tracey) were wonderful - friendly, responsive and also very respectful of our privacy. Loved the king-size bed in the Sara Delano Room - sooooo comfortable!

Show all

Bed and breakfast rentals with a patio

A well-appointed room features a carved mahogany four-poster bed dressed in elegant bedding. Natural light pours in through multiple windows, illuminating the soft yellow walls. A cozy seating area includes a stylish armchair and a decorative side table, while a dresser adds to the inviting decor.

Private room in Falmouth

Edith Wharton - Palmer House Inn

DawnRating, 5 stars7 months ago

Our host was incredibly friendly. The communication for our late check in (after dark) was clear and easy to follow. The room was very clean. Enjoyed our stay and will consider this location again.