Bed and breakfast vacation rentals in Oak Bluffs

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Top-rated bed and breakfast rentals in Oak Bluffs

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

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Guest favorite

A spacious wooden deck is featured, surrounded by tall trees and greenery. Outdoor furniture, including a table with chairs and a large umbrella for shade, is arranged neatly. The deck provides ample room for relaxation and outdoor dining.

Private room in North Falmouth

4.81 out of 5 average rating, 643 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

A pathway lined with green shrubs leads towards an open view of a lively scene, where vehicles, trees, and buildings are visible against a clear blue sky. The sunlight brightens the surroundings, enhancing the coastal ambiance.

Private room in Oak Bluffs

4.88 out of 5 average rating, 72 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!

Top guest favorite

The charming house is nestled among lush trees, showcasing a welcoming porch with white railings. A well-maintained garden is visible in the foreground, complemented by vibrant greenery. The structure features a gabled roof and a skylight, blending harmoniously with the serene surroundings.

Private room in Bourne

4.94 out of 5 average rating, 266 reviews

Lovely Farmhouse 2 private rooms & artisanal food

Filled with art and feng shui, our beautifully appointed home is tucked amidst vegetable gardens and flower patches. Outside you'll enjoy nature walks and beaches. Afterwards, you'll retire to a cozy bedroom, private bathroom, and leisure room with skylights, TV, and sofa to relax in. For breakfast you'll savor local specialty foods such as gourmet granola, artisan bread, steel-cut oats, and more. If you like basking on a deck or chilling on a porch, then this is where you'll want to call home.

Top guest favorite

Private room in North Falmouth

4.91 out of 5 average rating, 235 reviews

North Falmouth Suite 'downstairs suite'

This gueen-bed suite has a private entrance, a living room with wifi/tv, and a small, private bath, on a beautifully maintained property on 28A in N. Falmouth. Enjoy easy access to beaches & the bike path is across the street. The suite is priced based on two people, additional people - older kids, friends, are $40/night more; two twin blow-ups can be set up in living room. You must list the total amount of guests when booking. This house is not well suited to toddlers & young children.

A cozy loft bedroom features a pitched wooden ceiling, creating an intimate atmosphere. A spacious bed is adorned with decorative pillows in a circular pattern. Natural light filters through a small window, complemented by bamboo shades, while bedside tables with lamps are positioned on either side.

Hotel room in Tisbury

4.88 out of 5 average rating, 26 reviews

2Bdm Guesthouse at Luxury B&B -Kitchen & Living Ro

This is a two-bedroom unit with one of the bedrooms in a partial standup loft. This loft is only accessible by a library ladder. My place is close to the beach and restaurants and shops. My place is good for couples, solo adventurers, and business travelers. Limited maid service - we provide breakfast served at the poolside and bikes for your entire stay. We also provide beach towels and chairs! We welcome guests aged 12 and older. For special weekly winter rates, please contact us.

Superhost

A serene outdoor seating area is positioned along the water's edge, featuring two bright purple adirondack chairs, a small table, and a long bench with decorative pillows. A fire pit sits on gravel, surrounded by lush greenery and views of the river.

Private room in Barnstable

4.91 out of 5 average rating, 90 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.

Guest favorite

A stone staircase adorned with greenery leads to the private entrance of the suite. Flower pots in various colors enhance the inviting atmosphere, while shrubs frame the path. The surrounding area features a mix of plants and pebbled ground, creating a tranquil outdoor space.

Private room in Pocasset

4.93 out of 5 average rating, 225 reviews

Cape Cod/Bourne: Cape Escape Suite

Quiet, fully Private suite in my non-smoking, post and beam home. A sitting area with light cooking access available. Private entrance and bath. Wood floors throughout. Guests say the space is larger than photos reveal. Hiking trails and quiet cove with beautiful sunsets are a 5 min walk away. Close to Bike path to Woods Hole and along the canal. Cape Flyer stop near by. A Pick up is available. Recommend a 3 night stay in order to fully explore the Cape and an island.

Top guest favorite

A clear blue swimming pool is surrounded by a textured pool deck, with lounge chairs positioned nearby. Lush green trees and the home’s exterior are visible in the background, offering a serene outdoor space for relaxation.

Private room in Falmouth

4.96 out of 5 average rating, 244 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 winding pea stone driveway is flanked by natural landscaping, leading to a charming beach house surrounded by trees. Soft sunlight filters through the foliage, creating dappled shadows along the path. The house's inviting entrance is visible in the distance.

Private room in West Tisbury

4.96 out of 5 average rating, 28 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.

Guest favorite

The exterior of the post and beam structure features a wraparound porch adorned with flower boxes and views of the surrounding greenery. A fenced yard is visible, complemented by a grassy lawn and mature trees, creating a serene outdoor space.

Private room in Tisbury

4.96 out of 5 average rating, 129 reviews

Spacious 1850s rustic meets modern walkout studio

Located on 1.6 acres, just a 6 minute drive from Vineyard Haven town center, this lovely post and beam walk out basement apartment is the perfect home base to explore the island. Although the home was built in 2000 and has all the modern amenities you could hope for, its structure, reclaimed from a Connecticut dairy barn built in 1852 brings old world charm to this stunning space. Please note that our family of 5 lives upstairs so there is potential for noise.

Guest favorite

A tranquil garden area features relaxing lawn chairs positioned on lush green grass. The entrance of the Inn is visible, framed by vibrant flowers and foliage. A rustic wooden table is set nearby, enhancing the serene outdoor setting.

Private room in Vineyard Haven

4.88 out of 5 average rating, 51 reviews

The Look Inn/Parrish Room

The Look Inn is a licensed bed and breakfast Inn by the Town of Tisbury/Vineyard Haven celebrating our 30th year of operation. The Parrish and Blue and Look Out Rooms have a queen size bed and can sleep one or two people. The rooms shares a full bath with the rooms that each have sinks with hot/cold water and the common spaces of living room with tv and screened porch. There are relaxing lawn chairs that view the many gardens of flowers and vegetables.

Superhost

An outdoor area features a combination of seating arrangements with vibrant blue chairs and picnic tables among various trees displaying autumn foliage. A firepit and grill are situated in the space, surrounded by well-maintained landscaping and a swing set, offering a peaceful retreat.

Private room in Forestdale

4.86 out of 5 average rating, 276 reviews

CENTRAL CAPE COD LOCATION QUIET, CLEAN, PRIVATE.

It's a beautiful home, bright cozy bedroom, w/coffee maker, micro, refrigerator/freezer, toaster oven, coffee, tea, creamer, bottle water, soda water, and snacks. Beautiful covered deck over looking tranquil yard you may use. Whole house water filtration system. Ceiling fan, table top fan, window fan, AC, heater, beach umbrella, chairs, towels & blanket. Firepit area, outdoor grill, sitting areas in yard. Everything you need for a great get away.