Bed and breakfast vacation rentals in Oak Bluffs

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Top-rated bed and breakfast rentals in Oak Bluffs

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Guest favorite

Private room in North Falmouth

4.81 out of 5 average rating, 676 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

Private room in East Chop

4.89 out of 5 average rating, 92 reviews

Oak Bluffs/ Harbor Views/ Queen Bed/ In Town

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!

Private room in East Falmouth

5 out of 5 average rating, 5 reviews

Peace & Plenty 3 Falmouth: Private Beaches, Tennis

Peace & Plenty 3 has a queen bed with access to common areas in a spacious home in a private community (Menauhant) East Falmouth, MA. Guests walk/bike to 3 private beaches, 3 clay tennis courts, kayaks, an outdoor shower & yard games. Our Yacht Club offers group & private tennis lessons, junior sailing programs, and multiple family events (BBQs, dinner dances, game & movie nights, etc.). Guests pay a nominal Club fee based on length of stay and total people in season. Please ask for details.

Top guest favorite

Private room in West Falmouth

4.92 out of 5 average rating, 247 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.

Top guest favorite

Private room in Oak Bluffs

5 out of 5 average rating, 31 reviews

The Mary Suite- Kathleens Kottage- 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.*

The room features a king-size bed dressed in a floral green and white comforter, surrounded by multiple pillows. A wooden dresser and two bedside lamps provide soft lighting. Natural light filters through sheer curtains, enhancing the inviting atmosphere of the space.

Private room in Falmouth

Walt Whitman - Palmer House Inn

Searching for where to stay in Cape Cod MA? Our bed and breakfast in Falmouth offers a Cape Cod ADA accommodation with a separate entrance. The king-size bed can be separated into two twin beds with advance request. Please note, the king-size bed has a small ridge running down its middle, where its two halves are joined. Sitting area and writing nook with antique writing table. View our Accessibility Policy. The Walt Whitman room is also one of our five pet-friendly accommodations.

Top guest favorite

A bright living room features a beige sofa with decorative pillows and a navy throw blanket. A wooden coffee table sits in front of the sofa. Two armchairs are positioned nearby, and large windows allow natural light to enter, enhancing the inviting atmosphere.

Private room in Falmouth

4.97 out of 5 average rating, 269 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.

Private room in West Tisbury

4.89 out of 5 average rating, 27 reviews

Bright, Unique on Martha's Vineyard!

SPRING SPECIAL through June 15: Min Stay 2 nights, stay third night, get 30% rebate from hostess! A spacious room with bath in a studio behind my house, opens onto a broad meadow, abuts bike & walking trails. Serene, yet just 5-20 minutes from beaches & towns & all the lively Island happenings. If you are coming for a wedding, an anniversary, a reunion or just for the humming of nature and the sea, The Broad Meadow is for you. NO ROOM TAX - Good breakfast & beach passes!

Top guest favorite

A charming yellow farmhouse is framed by lush green trees and colorful foliage. Outdoor seating made of lawn chairs and garden benches surrounds a landscaped area, inviting relaxation. The structure features multiple windows, allowing natural light to brighten the inviting exterior.

Private room in Vineyard Haven

4.88 out of 5 average rating, 60 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 35th 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. Serving guests over 18

Guest favorite

Private room in West Tisbury

4.97 out of 5 average rating, 36 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

Private room in Tisbury

4.96 out of 5 average rating, 139 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.

A cozy bedroom features a full bed with a colorful patterned comforter. Natural light enters through a partially covered window. A wooden dresser and a small table are present, along with decorative wall art and a shelf displaying various items.

Private room in Tisbury

4.85 out of 5 average rating, 201 reviews

Cozy Room in Vineyard Haven

Enjoy this sparkling clean and cozy first floor bedroom in our Vineyard Haven home which is perfect for travelers to the Island of Martha's Vineyard. We may be hosting up to 2 additional groups of guests in our home at any given time. Please keep this in mind! A 5 minute / 10 minute drive from the ferry and airport. The bus to Edgartown stops right in front. A 20 minute stroll to downtown Vineyard Haven. Soak in the sunshine on the wraparound deck.