27,207 properties available

Located in Oak Bluffs, Massachusetts, United States. Beautiful home with pool in great location- close to everything! 2 bedroom home with 2 big full bathrooms. Walk to ferry and town center. One of the bathrooms include a jacuzzi tub and stand up shower. Bedroom upstairs is large to sleep 4. Walking distance to all amenities. Beautiful pool and 2 decks that are suitable for entertaining and enjoying meals and time outside. Great front porch with a swing and parking space in front of the house. House has a wonderful living space with high ceilings and open kitchen floor plan. Walk to East Chop and enjoy the beautiful Cliff Views in 5 minutes.

Located in Oak Bluffs, Massachusetts, United States. Beautiful and Renovated House near center Welcome to this beautiful and pristine 3 bedroom 1 1/2 bath home located in Oak Bluffs, Marthas Vineyard in a peaceful neighborhood. This property is conveniently located close to the beach as well as the city center and popular restaurants. This home shows pride in the well manicured yard and spacious back porch. Highlights include a large kitchen with gadgets great for cooking. Ample rooms with lots of space and natural light. Living room with comfortable sofas, tv and wifi throughout house.Huge backyard with grill, hammock, large table and chairs and green grass for activities. Great for relaxing, reading a book or having a nice BBQ with friends and family. Backyard is fenced for privacy. Large enclosed and open garage for rental cars. Bicycles are available upon request for guests to use on their stay. Modern and cozy feel for anyone of all agesThe basement is a separate, occupied unit with its own private driveway, entrance, and yard. Only

Located in Oak Bluffs, Massachusetts, United States. Oceanview East Chop Beach House - 4 Bed/2 Bath - 5 min walk to beach The perfect vacation awaits you at Frog Prince Cottage in beautiful East Chop, the finest neighborhood in Oak Bluffs. Our fully renovated Victorian beach house seamlessly blends the charm of the island with modern amenities. Wake up to panoramic water views from your bedroom; sip your morning coffee as you watch the ships sail by; bike to the shops on Circuit Avenue and the beauty of Inkwell Beach; or take a 5-minute stroll to Jetty Beach for a relaxing swim. Your night ends in serenity, away from the crowds, with only the sound of ocean waves hitting the shore outside your window.Our home features a wraparound front porch, as well as a private back deck with a new Weber grill, which is ideal for dining al fresco. A chef's kitchen, cozy dining room, and spacious living room are suited for family gatherings. An outdoor shower, professionally landscaped yard, and private parking are at your disposal. Our home is availab

Located in Oak Bluffs, Massachusetts, United States. Spacious family-friendly home with fast WiFi, beach access, & washer/dryer Nautical DazeOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Simply filled with coastal charm, this lovely home will be an amazing jumping-off point for your next vacation to Oak Bluffs! Just down the road from beautiful beaches, this home is perfect for you and your loved ones to enjoy the ultimate east coast getaway. Take a ride on the Oak Bluffs Ferry, spend your day at the quaint fishing bridge, or tour the coastal town to find unique shops, local eateries, arts, entertainment, and an array of family-friendly attractions.Inside you'll be met with a bright interior and a warm feeling of welcome throughout the space. The living area invites you in to lounge about the plush furniture, while the kitchen invites hobby chefs to create culinary charms on the stainless steel appliances. Three bedrooms are comfortable and spacious

Located in Oak Bluffs, Massachusetts, United States. Last minute cancelation! August price reduced! Large, Renovated, Walk to Beach! Last minute cancelation on August week! Big Price reduction!This charming Vineyard home just completed a large renovation including all new bathrooms and a new bunk room and first floor master! It sleeps 12 in a perfect East Chop location! In minutes you can be on the beach or into town! It boasts 6 bedrooms, three full newly renovated bathrooms, one half bathroom and has a lovely private outdoor shower! The recently renovated kitchen is perfect for cooking and gathering around the large custom farmhouse table. It's the perfect home for a long family stay on the Island to soak up some time with friends and family. Beautiful front porch with plenty of seating for all. Views of the sound and harbor. Back patio with plenty of seating to eat outdoors with grill as well as large side yard.There is a spacious cozy living room and seating area for family gatherings. The first floor has a large brand new master bed

Located in Oak Bluffs, Massachusetts, United States. 4 BR/4 BA Modern Victorian: The Mack on Winemack This beautiful Victorian home has all the charm of a true Martha’s Vineyard Gingerbread cottage combined with all of the space and amenities of a large modern home. Built in 1999 and redesigned in 2020, this home has 2,400 sf of living space with 4 bedrooms and 4 bathrooms.We are just one mile from downtown Oak Bluffs, the harbor and beaches. The home is located at the very end of a quiet dead end street, offering a large well-landscaped yard that backs to beautiful trees and walking paths. A wrap-around porch with mahogany wood floors offers plenty of seating areas to enjoy the day and includes a sunroom to enjoy your morning coffee and breakfast. A grill and round fire-pit await you in a spacious back yard. First FloorThe first floor has a spacious living room accented with mahogany wood pillars, stylish furniture and a 60in. SMART TV. There is a well-appointed kitchen with a separate dining area, and counter with seating. There

Located in Oak Bluffs, Massachusetts, United States. Historic House w/ amazing rooftop deck. Dog-friendly and perfect for big groups! Welcome to your ultimate Martha's Vineyard getaway! This exquisite 6-bedroom house is the perfect destination for a luxurious and unforgettable vacation. From the moment you arrive, you'll be captivated by the stunning views of the harbor, enjoyed from the expansive roof deck. As you step inside, you'll be welcomed by a beautifully decorated living area that exudes coastal charm and elegance. The spacious open floor plan allows for easy flow between the living, dining, and kitchen areas, making it perfect for gathering with family and friends. The living room features comfortable seating and a large, flat-screen TV for your entertainment needs. The kitchen is fully equipped with state-of-the-art appliances and all the tools you need to prepare gourmet meals. Whether you're a culinary enthusiast or just want to whip up a quick breakfast before hitting the beach, you'll find everything you need here. The ad

Located in Oak Bluffs, Massachusetts, United States. Lovely vacation home within walking distance to Oak Bluffs and the beach Welcome to your summer vacation home! This is a 3 bedroom 2 1/2 bath home located less than a mile from downtown Oak Bluffs. Famous for its ice cream parlors, back door donuts, "Flying Horses" carousel, variety of cuisines, night life, and much more. The open floor plan with an attached 3 season porch is perfect for entertaining, but cozy enough to create the perfect ambiance. The master suite is on the 1st floor and the living room has a beautiful teakwood spiral staircase to the 2nd floor. The second floor has 2 bedrooms, full bath, office area and a TV room. The house sleeps 6.

Located in Oak Bluffs, Massachusetts, United States. Historic Oak Bluffs home, short walk to town, beach, and harbor. Family owned and kept charming 19th century home in Oak Bluffs highlands near Baptist Temple park. This house is about 1/2 mile walk to ferry terminals for Island Queen, Vineyard Fast Ferry, Seastreak, Hy-Line and Steamship Authority (Oak Bluffs terminal). Three bedrooms total with two queen beds and one twin bed. Full bathroom upstairs with indoor shower, half bathroom downstairs, plus an outdoor shower. Window unit A/C's provided throughout (each bedroom has one A/C). For cooler months, the heating is a working wood stove and electric space heaters which are provided. 10-12 minute walk to downtown Oak Bluffs for all needs. Private parking for up to (4) vehicles. Charming wrap around covered porch in front, small deck in back with very private yard. Wifi internet to work remotely or stream shows/movies. Windows 10 PC available to display Netflix, Hulu, sports, etc. No cable TV.

Located in Oak Bluffs, Massachusetts, United States. Perfect one bedroom garage apartment with A/C This charming one bedroom is perfect for a couple or small family looking for a great space and in a great location just a mile from Downtown Oak Bluffs. Built in 2017, this unit has great amenities including A/C and stylish wood floors. The apartment is over the garage on a property at the end of a quiet street and offers COMPLETE privacy from the main house. There are two private entrances (one from inside the garage and the second one from stairs outside) along with two designated off-street parking spaces.The bedroom has a queen bed, plenty of storage and a wall-mounted Smart TV. There is a cozy kitchen with countertop seating and plenty of space to cook any meal. The living room has a brand new queen sleeper sofa and wall-mounted Smart TV.l. There is a washer/dryer in the garage for the sole use of apartment tenants.

Located in Oak Bluffs, Massachusetts, United States. Vineyard Cottage Charm, Walk to Beach, On Bike Path, Near Town Mid-century rustic cottage charm tucked on 3 acres 1 mi to Oak Bluffs and Vineyard Haven center's. Acquired in 1950 by Lisa's grandparents, the original style of this family heirloom has been lovingly preserved. Comfortable new furniture with vintage accents, lovely linens, memory foam mattresses, lots of outdoor space and privacy, and convenient location defines this property. Walk to beach and bus stop. Direct bike path access. Open living and dining area, with separate kitchen. A covered outdoor breezeway connects bedrooms, shower room and bathroom to the main living area. There's a screen porch, outdoor porch, patio, and huge yard. Property is set back 100 yards from the road. Plenty of parking. Lots of great amenities! Memory foam and coil mattresses, nice pillows, soft cotton sheets and comforters, and soft blankets make sleeping very comfortable. Lovely thick cotton towels. Smart HDTV with Roku live TV, Netflix, HBO

Located in Oak Bluffs, Massachusetts, United States. Heart of Oak Bluffs, No Car Needed! Ocean Views, Walk to Everywhere! ** All August reservations are Saturday-to-Saturday. **Welcome to “Gem of the Ocean”! Martha’s Vineyard vacationers dream! This recently updated condo with private balcony and spectacular ocean views is within walking distance to everywhere in downtown Oak Bluffs and a front row seat to all the activity and attractions around Ocean Park: Inkwell Beach, Circuit Avenue, Linda Jeans, Flying Horses, Carousel, OB ferry and harbor, Campground Cottages, Tabernacle, Illumination, shops, restaurants and more! No car needed. Beautiful second floor 2 BR/1 BA condo sleeps up to 4 guests. The master bedroom has a king bed. The second bedroom has full and twin beds, The recently updated bathroom has a tub and shower combo, new vanity and chair height toilet. Amazing location with spectacular views! Located in an historical building, you’ll enjoy this bright and airy space, with views of the ocean and Ocean Park from the private

Located in Vineyard Haven, Massachusetts, United States. Contemporary Pet-friendly Retreat Contemporary with open living/dining area, cathedral ceilings, and air conditioning throughout. Sliding and French doors lead to wrap-around decks and a screened-in porch adjacent to the dining room. Outdoor shower.Walking distance from Lake Tashmoo and Vineyard Haven. A mile and a half to beautiful Tashmoo Town Beach. Lots of amenities including fully stocked kitchen, linens, gas grill, and digital piano. Located on very quiet, dead-end street surrounded by woods. Wireless, high speed Internet. Smart TV. Washer and dryer.Green features include solar panels for electricity generation, EV charging, and mini-splits for AC and efficient room-based heating.Beds: Queen in master bedroom, twin and trundle (sleeps 3) in second bedroom, full in third bedroom, futon sleep sofa in living room. Master bedroom has private bath with luxurious walk-in shower, .and sliding doors leading out to lower deck.Kitchen and bathrooms all updated.Pet-friendly.High sp

Located in Oak Bluffs, Massachusetts, United States. Charming home with deck, W/D, & amazing location Oak Bluffs DarlingOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Located in the charming town of Oak Bluffs, MA, this house offers a cozy retreat for your Martha's Vineyard getaway. Just a short walk to the bike path on County Rd and moorings on the Lagoon Pond, this home is perfectly situated for outdoor enthusiasts. With wood floors and a quarter-acre leafy yard, this home provides a welcoming atmosphere. Relax in the hammock strung from a tree in the front yard or enjoy the spacious deck along the side and back of the house. A patio table and chairs for four with umbrella will be ready for your enjoyment. This dog-friendly property is equipped with all the amenities you need for a comfortable stay, including a high chair, Pack and Play, washer/dryer, internet, gas grill, and more. Whether you're cooking in the fully stocked kitchen or lounging in

Located in Oak Bluffs, Massachusetts, United States. Perfect location! Beach, Harbor & Town. Beautiful 1st Floor Apartment Oasis This lovely, in-town, first-floor apartment is in a renovated 1800's historic Oak Bluffs cottage with a fenced in landscaped patio. The beautiful stone patio out the kitchen door has plenty of seating, an outdoor shower, 2-person hot tub (please let us know if you think you will use it), propane bbq grill, and an outdoor designer Rais fireplace. The large and sunlit gourmet kitchen has skylights and is the heart of the home.This apartment accommodates up to 4 guests, with one very petite queen bedroom and a large living room that can be entirely closed off as a separate room, with a queen Crate and Barrel sofa bed. The room can be closed off from the rest of the apartment for privacy with glass french windows and doors and curtains, and can have a separate entrance as well. The very large country kitchen with every amenity you could hope for.There is one full bath (with tub/shower) in the apartment, and one add

Located in Oak Bluffs, Massachusetts, United States. The Nest, Comfortable, Cozy and Convenient The Nest is a private entranced guesthouse that is ideally located 2/3-1 mile walking distance to Oak Bluffs town, harbor, beaches and ferries (summer ferry service is in Oak Bluffs and Vineyard Haven, winter service is Vineyard Haven ONLY). We offer one bedroom with a queen bed and a queen sized sofa bed in the living space with a private bathroom. This newly remodeled space has a full service kitchen, air conditioning, heat, cable TV and WiFi all for your comfort and convenience. The Nest is waiting for nesters!

Located in Oak Bluffs, Massachusetts, United States. Spacious 1 Bedroom Apt - 3 min Walk to the Beach! A perfect place for 1-4 people to stay! You will have plenty of room, shared use of a grill, backyard, and outdoor dining area. Location is fantastic - it's only a 3 minute walk to the lagoon/beach, 20 minute walk to the Oak Bluffs harbor, 25 minute walk to downtown Oak Bluffs, and 7 minute drive to State Beach.We have central AC and heat to keep you comfortable no matter what the temperature is!The owners live upstairs with their two young kids (4 & 6). As such, this listing is for early-risers ready to enjoy the beauty of island mornings :)

Located in Vineyard Haven, Massachusetts, United States. Central 2nd-floor apartment with propane stove, grill, W/D, & great location Main Street UpperOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Tisbury Town Beach, Owen Park Beach, and Vineyard Haven shops, restaurants, and activities are all within a half-mile of this convenient Main Street retreat. Within walking distance of the ferry terminal and town services, this second-floor apartment also offers windows facing the harbor and Owen Park Beach. Leave the car behind while you explore around town or hop on the ferry to spend the day on Cape Cod. The sunny interior comes well-appointed for contemporary seaside living. The fully updated kitchen boasts a sparkling suite of all-new stainless steel appliances, including a dishwasher, for stress-free meal prep and planning. Plush seating, a propane stove, and a mini-split air-conditioner offer all-season comfort for group gatherings in the living room, w

Located in Vineyard Haven, Massachusetts, United States. Cozy Vineyard Haven Cottage < 1 Mi to Beach! Your next summer trip to Martha’s Vineyard starts at this vacation rental in Vineyard Haven! This 1-bedroom, 1-bathroom cottage is the ideal spot to discover all the top attractions the area has to offer. Bury your toes in the sand at Tisbury Town Beach, Oak Bluffs, or Lake Tashmoo, set out on a hike on the nearby wooded trails, and rent a bicycle to explore the island at your leisure. When the day is done, return home for a movie night before doing it all again tomorrow. The Vineyard awaits!-- THE PROPERTY --MassTaxConnect ID: C0224992960 | Near Ocean | Hiking Trail Access On-Site Bedroom: Full BedINDOOR LIVING: TV, dining table, ceiling fans, distressed wood, exposed beam ceilingsKITCHEN: Stove/oven, microwave, refrigerator, coffee maker, toaster, dishware/flatware, trash bags/paper towelsGENERAL: Free WiFi, washer/dryer, linens/towelsSUITABILITY: 2 steps required to access, single-story homeFAQ: No A/CPARKING: Driveway (1 vehicle)ADDT’L A

Located in Vineyard Haven, Massachusetts, United States. Charming Oak Bluffs Cottage: Prime Location, Stylish Comfort & Serene Privacy Charming Cottage in Oak Bluffs: Your Perfect Island Getaway!Welcome to our cozy and comfortable cottage in the heart of Oak Bluffs, where everything you need for a memorable vacation is just a short walk or bike ride away!Features:Spacious Wrap-Around Deck: Enjoy the expansive deck, complete with outdoor furniture and a refreshing outdoor shower—perfect for rinsing off after a day at the beach.Prime Location: Stroll or bike to nearby attractions like Sunset Lake, East Chop Lighthouse, Bistro Bowling Alley, The Arts District, Oak Bluffs Harbor, Circuit Avenue, Flying Horses Carousel, Inkwell Beach, Town Beach, the historic Campground Meeting Gingerbread Houses and Tabernacle, Union Chapel, great restaurants and the Oak Bluffs Steamship Authority terminal. The island’s bus service is conveniently located just outside the door, making exploring the rest of the island easy.The Cottage:Stylish & Homey: Our cottage

Located in Vineyard Haven, Massachusetts, United States. Well-Appointed 3 bedrm 4 bathrm with AC and 50+ 5-star reviews! *** IF INTERESTED IN BOOKING, PLEASE SEND AN INQUIRY (click on ’contact host’) PRIOR TO SENDING A BOOKING REQUEST. BOOKING REQUESTS SENT WITHOUT PRIOR CONFIRMATION OF AVAILABILITY CANNOT BE ACCEPTED.This spacious, beautiful, and well-decorated home is conveniently located at the end of a quiet residential street abutting 8 acres of conservation land. The house is fully furnished & equipped, exceptionally clean, and well-maintained. The main living area consists of a bright and airy open-concept space with cathedral ceiling, multiple skylights, central AC plus a ceiling fan. There is also radiant heat throughout the house and a fireplace in the living room. The state-of-the-art, fully appointed kitchen has a large island, granite countertops and Jenn-Air stainless appliances. Home is tastefully decorated throughout with a mix of antique and modern furnishings as well as oriental rugs and original artwork. The master bedro

Located in Vineyard Haven, Massachusetts, United States. Steps to the beach - Vineyard Summer home This charming summer cottage offers the quintessential vacation experience close to Vineyard Haven center. Walk to the beach at the end of the lane in this quiet residential neighborhood in West Chop. The art collector owner provides a delightful setting for your family vacation. Large family room with gas-fired fireplace is perfect for evening gatherings. Expansive yard allows ample room for outdoor games and activities. Two bedrooms, one bath, plus sleep sofas accommodates 5-6. SATURDAY TO SATURDAY RENTAL

Located in Oak Bluffs, Massachusetts, United States. Big Beach House - Ocean Views! Original 1900 Victorian home, updated in 2006, located in the historic Copeland District just one block from the beach. Three story home boasts decks and wrap around porch with ocean views from each. Five large bedrooms, spacious living room with French doors that open to the large wrap-around porch. Enjoy relaxing meals in the formal dining room and eat-in kitchen. Rec room in basement includes stone dry bar and 55' wide screen TV. Original wood paneling throughout. Fenced in back yard for privacy, perfect for post-beach barbecues. On Waban Park. 5 minute walk to town and Back Door Donuts; 1 minute hop, skip or jump to Oak Bluffs town beach/Inkwell.

Located in Oak Bluffs, Massachusetts, United States. Coastal home with outdoor shower, grill, fireplace, central AC, & W/D Yellow Brick Road HouseOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Bright and inviting, this home provides an ideal escape for your family's next coastal vacation. Venture to nearby beaches and eclectic shops during the daytime, then return home to spend more time outdoors in your spacious backyard. Rinse off in the outdoor shower before you fire up the propane grill for a barbecue. Listen to favorite playlists on the speakers while you dine at the shaded six-person dining table. A hammock provides a convenient spot to kick back with a good book, while the front yard offers more space for lawn games.Large windows invite natural light into the living area. Cozy up by the gas fireplace while you stream favorite shows on the smart TV. Outfitted with stainless steel appliances, the modern kitchen features everything you need to wh