27,207 properties available

Located in Oak Bluffs, Massachusetts, United States. Comfortable Island Home, Easy Access to Beaches and Town Salt Box style Log Home with open floor plan built by my family with a country feel, located on a wooded lot in the down island town of Oak Bluffs. Central Air and easy walk to local beach that is used by families of the Lagoon Heights area. Beautiful town and state beaches close by. Charter fishing, golf, great restaurants and ample shopping for the occasional rainy day. Many local attractions to visit, gingerbread homes, tabernacle, oldest functioning carrousel, walking/ bike trails and nature preserves to keep one busy while enjoying the the Vineyard's laid back, casual nature. First floor bedroom has queen bed, upstairs has the full bed. Loft area has three twin beds. Screened porch has wicker furniture, two couches and two comfortable chairs. The home provides a comfortable retreat for those that prefer to be away from crowds, yet only a short trip to town and the beaches.*If not able to bring your own linens, they

Located in Oak Bluffs, Massachusetts, United States. Fully Renovated & Spacious home walking distance to downtown Oak Bluffs/Beaches Newly renovated three-level home with 3 bedrooms 2 bathrooms within walking distance to the heart of Downtown Oak Bluffs and beaches. This location allows you to be at the center of activity from Fourth of July fireworks to Illumination but a quick escape into the quiet neighborhood of The Highlands. Walking distance from Oak Bluffs Town Beach (Inkwell) and ferry station. A bright spacious fully renovated and well-appointed must-see home that you won’t want to leave. Comfortable living spaces for 6 people to relax and socialize. Open kitchen with new appliances and all the cooking tools necessary to whip up a pot of chowda or to have guests over to enjoy a lobster bake. Beautiful rooftop deck with a view of the Harbor and lake or a great place to listen to the morning chirping of birds. Two Bedrooms on the second floor- one with a comfortable Queen bed and the other with 2 twin beds. Master bedroom with b

Located in Vineyard Haven, Massachusetts, United States. Your Summer Home - Close to Beach, Shops, Cafes, & Ferry! 50+ ⭐️⭐️⭐️⭐️⭐️ Reviews With more than Fifty, 5-STAR REVIEWS, you can book with confidence. This beautifully appointed home features luxe furnishings throughout the house. Three generous bedrooms including a first floor master bedroom, 2 and a half bathrooms, large livingroom with bright sunroom, kitchen, with dining area, and beautiful large deck for relaxing and dining. AC, Wifi, Satellite TV all included. A short 5-10 minute stroll to local beaches, and a15-20 minute walk to all of the shopping of charming downtown Vineyard Haven.

Located in Vineyard Haven, Massachusetts, United States. Walk-up apartment with deck & grill - walk to beach & town Everyday is SaturdayOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Find yourself within easy reach of the best Martha's Vineyard offers with this cozy walk-up apartment. Just a short walk from the Steamship Authority Terminal and downtown Vineyard Haven, the home is also close to local town beaches. Golfers in the group will appreciate a convenient location close to Mink Meadows Golf Club. Walking trails from the home offer a three-mile loop to and from the scenic West Chop, offering some of the finest sunset views on the island. Beach chairs and various board games and playing cards are also provided for family fun and convenience. At home, you can enjoy outdoor living on the private deck and fire up the gas grill for summertime barbecues in the backyard.The sunny interior comes well-appointed for home comfort. The tidy kitchen area has a

Located in Oak Bluffs, Massachusetts, United States. Spacious 4 BR Home, Steps to Lagoon, Minutes to Downtown Oak Bluffs and Beaches! Spacious two-level four-bedroom house within steps to lagoon located in Oak Bluffs and within minutes to Downtown and beaches! Features both a separate living room and family room, two full bathrooms, a fully-equipped kitchen, and as a bonus has a screened-in porch to enjoy your morning coffee! This lovely home also has a large front and back yard, as well as a separate driveway. As another bonus, it comes with two cars for additional rental! Great for families. Sorry, no pets allowed. We have had many satisfied, repeat visitors!

Located in Oak Bluffs, Massachusetts, United States. Quaint,,,Quiet..up island feel yet a short walk to to , x ,, z wn and harbor Your quintessential summer vacation starts here! The property has a combination of a strong rental history(read rental reviews) and a lot of repeat guests. the house and guesthouse will make this rental a true summer getaway - all the feature comforts both inside and out! Comfortable beds and, luxury bath towels, furnishings, built-ins, central air, lighting, rugs, art work, and more! The spacious yard will encourage plenty of lounging under the shade trees, as well as an large area designated for outdoor games. The exterior deck is large enough to host the gas grill, dining table (with umbrella), seating for 6-8, as well as a private outdoor shower. All you need to clean up after a day at the beach, enjoy a few cocktails and get your BBQ going. A short walk to town and harbor and just around the corner from the campground cottages, yet set on a very quiet street with an up-island feel !! Wifi an

Located in Oak Bluffs, Massachusetts, United States. Discover the magic of Martha’s Vineyard! NEW ! Build in 2020 ! Build in 2020 ! New lovely studio apartment.Clean, bright and comfortable.700 sq feet !Great for couples, work trips, weddings.The spaceOur new studio is located above the garage attached on the side of the main house.Private entrance.There is a small outdoor deck on top of the stairs to the studio.The interior offers high ceilings, A/C, TV, wifi, cute kitchen, and lots of light. There is a queen sized bed and sofa.•Bike to town, the harbor, restaurants, shopping, Flying Horses carousel, and the arcade•Easy drive to State Beach•10 minutes from the ferryNEIGHBORHOOD Oak Bluffs is our favorite town for families visiting the Island - offering some of the best restaurants, ice cream parlors, fun shopping, the historical gingerbread cottages and the famous Flying Horses carousel! The harbor is a great place for a stroll to look at the amazing collection of boats from the Pirate ship to private yachts, and don't miss beautiful O

Located in Oak Bluffs, Massachusetts, United States. Private Waterfront, Beachfront, and 90' Dock. Views. Newly Renovated 3Bd 2.5Bath Spectacular water views from classic Martha's Vineyard waterfront home! Perched atop a bluff overlooking the Nantucket Sound and the wide lagoon between Oak Bluffs and Vineyard Haven.Secluded and private, yet only a short distance from the two main Martha's Vineyard downtowns. Use the house as home base and a central location to explore all of the sights, shopping and seafood that Martha's Vineyard has to offer, or stay home and 'get away from it all'. Spend your time relaxing in the sun on the brick patio or the shade on the outdoor lanai while you take in the views and feel the cool breeze from over the water. Enjoy the flowering beautiful landscaped yard, or take a walk and relax on the private beach or dock.Perfect for a romantic getaway for two, or for a special family vacation.

Located in Oak Bluffs, Massachusetts, United States. "The Carousel House" - Ocean Park - Featured in New York Times This house, built in 1865, was featured in the New York Times article on Oak Bluffs, 'The President Was Here (Grant, That Is).' The article described the unique Victorian homes on Ocean Avenue as 'the Fifth Avenue of Oak Bluffs.' Our house was featured in the article, and photographed in the New York Times online slide show. It is a unique Victorian home, wonderful for family gatherings. The location is ideal - it sits at the heart of Ocean Park, with the closest access to Circuit Avenue of any of the homes on the Park. The home has been completely renovated, including central air with two zones. Chef's kitchen with granite countertops and stainless appliances, a six burner commercial oven and a wine fridge. Bathroom sinks have marble tops. Four flat screen TVs. This house has unique charm and convenience. Walk to everything - you don't need a car. The child friendly beach is just across the road, where you can make sa

Located in Oak Bluffs, Massachusetts, United States. Glorious Sunsets and Fun on Private Waterfront in Beautiful, Comfortable Home. *** One round-trip, transferable, auto reservation on the steamship authority is included for remaining August 2024 weeks***. New, solar powered, 3200 sq. ft., waterfront, 4 bedroom plus flex room (sleeps 12), 3.5 bath, central air-conditioned home, flooded with fabulous sunsets on and over the water! Private Lagoon (saltwater) beachfront. EV charger. 1200 Mbps Wi-Fi. Located in a quiet neighborhood, a 15-20 minute walk to and through the Gingerbread Cottages of the Camp Meeting Association and on into Oak Bluffs Center; an easy walk or bike ride into town. Swim, kayak, paddleboard, windsurf, sail or fish right from the beach on the Lagoon or out onto Vineyard Sound (under the drawbridge).....with the sun rising or setting all around you. The water views include glorious sunsets, the ferries and sailboats coming and going in the Lagoon, the harbor and Vineyard Sound. Bring or rent a boat- tie up at our mo

Located in Oak Bluffs, Massachusetts, United States. Spacious Colonial Steps From Inkwell and Circuit Ave! Classic Beauty in the heart of Oak Bluffs. The Pennacook House is a year-round (heating and AC!) 6 bedroom, 2.5 bathroom home. It has a parking for 4 cars, lovely eat in kitchen, formal dining and living room with bay windows, den/study, hardwood flooring, outdoor shower, gorgeous period detail and many upgrades throughout. Some upgrades include state-of-the-art propane Hot Water Heating system and Water Heater, new Electrical Panel and Service, new Dishwasher Irrigation in the lawn and flower beds and lots of painting inside and out. The full walkout basement has laundry and plenty of storage space. Great location just a few blocks from town center, ferries, harbor and beaches!Master Bedroom 1: Queen bed (2nd floor)Guest Bedroom 2: Queen bed (2nd floor)Guest Bedroom 3: Queen bed (2nd floor)Guest Bedroom 4: Twin bunk beds (2nd floor)Guest Bedroom 5: Queen bed (3rd floor)Guest Bedroom 6: Two beds (3rd floor)

Located in Oak Bluffs, Massachusetts, United States. Peaceful Oak Bluffs home Relax and pamper yourself kin a Mid-Century Modern Split-Level home. Located on a 1/4 acre lot minutes away from town,beach, restaurants, and shops. Walk to town and beach. Public transportation right across the street. Enclosed patio and large backyard ideal for grilling, socializing and playing for the kids. Spacious driveway and front yard. Lower level: living room, dining room and fully equipped kitchen. Upper level: Master Bedroom with King size bed and private bathroom; newly renovated, 1 bedroom with Queen size bed, 1 Bedroom with twin beds and bathroom in hallway.Washer and Dryer, TV's in Living room, Master Bedroom and Twin Bedroom, Wi-Fi, DVD Player, Cable TV. No Pets. Newly renovated master bathroom.Air Conditioners in every room except basement.Smoke and Carbon Monoxide Detectors throughout house.You must supply your own linens and towels. Beach Chairs and Umbrella included. Must make your own Ferry Reservations.Enhanced Cleaning Practices be

Located in Oak Bluffs, Massachusetts, United States. Newly Renovated! Walk to Town Oak Bluffs, 4 Bedroom/3 Bath A/C This newly renovated home is approximately 2100sf with 4 bedrooms and 3 bathrooms. Furnished and decorated by award winning Martha's Vineyard interior designer at Vineyard Decorators, this home features beautiful quality furnishings. The home is bathed in tranquil colors reflective of the Vineyard and its landscape. We are a 10 minute walk distance to downtown Oak Bluffs, the harbor and beaches. The home has everything new: new furniture, new central air conditioning, new kitchen and appliances, new hardwood floors installed throughout, newly painted and remodeled. Outside you will find an inviting deck with furniture, beautiful newly landscaped yard, patio with gas grill, and a private outdoor shower.First FloorThe first floor has an open floor plan with a spacious living room with a 65" Flat Screen TV. There is a newly renovated kitchen with a separate dining area, and counter with seating. A large master bedroom with Ki

Located in Oak Bluffs, Massachusetts, United States. Oak Bluff Cottage Near Town Our lovely cottage is well maintained and great for families, couples, and groups. There's plenty of parking, a great back yard for yard games, a spacious deck, BBQ grill, and outdoor shower! The organic herb garden is yours to enjoy with lavender, lemongrass, and thyme growing this year. This is our first year renting through the season. Walking distance to town, close to the bus route and Farm Neck golf course.This House comes with 8 sets of towels, available beach chairs, umbrella, small coolers. Things to do at the house: Fire pit for s'mores, board games, bbq, yard games, watch the sunset from the backyard deck, cable TV, and internet.Beach towels and spare sheets are available (Please wash and fold if used).Each room has an air conditioning unit and ceiling fan for your comfort. The living room and kitchen do not have A/C Units however there's an amazing cross breeze through the sliding glass door!

Located in Vineyard Haven, Massachusetts, United States. Captain Spring House: In Town Luxury - Water Views - Walk to Ferry! With sweeping views of Vineyard Haven Harbor, the Captain Spring House in-town luxury home combines water views with 4 levels of sophisticated and stylish living space, including two roof top decks, a home theater, tournament Pool Room, Penthouse Lounge, and more.This is the ideal luxury property to enjoy Martha's Vineyard. Our house is a short walk (2 blocks) from the ferry, town, and beach so you can really leave the traffic (and your car) behind! If you choose to bring your car there is parking for 2.The main floor of Captain Spring House features an open Great Room designed for entertaining, with living and dining areas, plus a large Gourmet Kitchen. The fully equipped Chef's Kitchen features marble countertops, grand prep island/breakfast bar with seating for eight, Wolf and Sub-Zero stainless appliances, two farmhouse sinks, double dishwashers, and a wine refrigerator. There are hardwood floors and high ceilings

Located in Oak Bluffs, Massachusetts, United States. **Vineyard Vacation Retreat** -3 BR Just a stone's throw from Oak Bluffs and it's beaches, this chic 3 bedroom home provides comfort and privacy. The large bedrooms and open concept kitchen/dining/living area accommodate up to 6 people comfortably. A place for you to put your feet up, kick away your worries, and enjoy some rest and relaxation. There is so much to do and explore. The adventure is just starting so make sure to pack up your swimmers, suntan lotion and get out the door. Kick back and relax, you're home.This delightful Cape Cod style residence in Oak Bluffs exudes warmth and charm through its inimitable French country, urban chic style. It has the added benefit of providing complete privacy by being situated at the end of a cul-de-sac opposite a wooded lot. LIVING AREA Entry to the house is via a large, sunny mudroom which leads into the open concept dining/kitchen/living space. Beautiful hardwood floors feature throughout the house. Entertainment is provided in the living

Located in Oak Bluffs, Massachusetts, United States. Home in Oak Bluffs near everything you want! Walk to Inkwell Beach in 7 min. Surround yourself with comfort and fresh furnishings! This is a beautiful four-year-old home that is stylishly furnished and comfortable inside and out. It includes space to both gather as a group and to spread out privately. In addition to open living room, dining room and kitchen, the property offers 4 bedrooms, 3 full baths (one on every floor), family room with wet bar, office, yoga/workout room (w/ mirrors and mats, no other equipment), den, two porches, deck and a back and side yard. Previous renters speak well of the amenities! If you want walking distance convenience to the Oak Bluffs ferry, beach, restaurants, grocery and convenience stores, shops, entertainment, parks (playground, baseball, basketball, pickle ball, tennis) and the bike path and still be located in a quiet residential area overlooking the beautiful Nashawena Park, THIS IS YOUR PLACE to stay! Book your 2024 rentals now for stays Ap

Located in Oak Bluffs, Massachusetts, United States. Spacious family house, short walk to the Lagoon & close to Oak Bluffs center The 'Anchor Inn' on Carole Avenue is the perfect spot for your family to relax and enjoy the Vineyard! The home is a 4 bedroom, 1970 sq ft garrison, less than 2 blocks from the Lagoon and 1.2 miles to Oak Bluffs center. A bike path that takes you to Oak Bluffs or Vineyard Haven is right at the end of the street! It takes just a few minutes to drive or bike to beaches and shops/restaurants in Oak Bluffs or Vineyard Haven. Farm Neck Golf Club is 1.5 miles away. Edgartown is 15 minutes away by car. The Lagoon is the perfect spot for kids to play in the warm, calm ocean water and beautiful sunsets are an added bonus. The house also comes with a deep water mooring to use in the Lagoon that would hold a 22 foot boat.The first floor has a large family room, a separate living room, dining room, kitchen and utility room with a washer and dryer. There are sliding glass doors from the family room to a deck with sea

Located in Oak Bluffs, Massachusetts, United States. Famous Martha’s Vineyard Gingerbread Home Seashrimp. In downtown Oak Bluffs. Year-round Oak Bluffs in-town Historical Famous Seashrimp Gingerbread House across from harbor/Nancy's all on the water restaurants. 3 Bedrooms 2.5 baths. Lovely ocean views of harbor from the rockers on porch. Fully Air Conditioned/Heated. This home is 1/2 block walking to public beaches. One street over from Circuit Ave., shops and restaurants, Flying Horses (oldest carousel in the country). Walk to Steamship Authority dock or take fast ferry from across the street to Falmouth, Nantucket. Charter many boats across the street in harbor for fishing, sunset cruises etc. Onsite parking for 1 car in private driveway. This property is part of the Martha’s Vineyard Camp Meeting Association. Renters must observe quiet hours and all rules located on our website.

Located in Oak Bluffs, Massachusetts, United States. Beautiful 5 BR, 4.5 baths w/ modern conveniences We welcome you to enjoy our spacious and comfortable home. It's a beautiful 5 BR, 4.5 bath Oak Bluffs home with modern conveniences and nestled in an idyllic, secluded location. Perfect for large family gatherings. The amenities include AC, granite kitchen counter tops, breakfast bar, W/D, WiFi, five flat screen cable TVs, DVD & VHS players, gas grill, outdoor shower, hardwood floors and wood-burning fireplace for ambiance or a chilly evening. Large dining room table (comfortably seats 8) and fully equipped kitchen includes dishwasher and stock pots for steaming your crabs, clams & lobsters for that ultimate 'Vineyard experience.' The house is located on a quiet street, has a large front porch, private back yard and 2 large decks for casual dining and relaxing. Close to everything - town (5 minute drive/15 min walk) , harbor, ferry, shops, and restaurants. Sleeps maximum of 10 people. Rentals are on a weekly basis, Sunday to Sunday.

Located in Oak Bluffs, Massachusetts, United States. Luxury Loft Historic Center Oak Bluffs This is a wonderfully designed contemporary loft space that is both chic and comfortable. The couches and chairs are down-filled and the kitchen and living area is spacious and convivial. This is a great rental for large families, and couples and groups of friends on vacation.The location is just perfect! You are within steps of everything! Shops, galleries, restaurants, cinema, golf and tennis both public courts and farm neck around the corner, harbor, grocery stores, liquor store, clubs, tabernacle, union chapel, ocean park, public basketball court , walking trails, bike bath along ocean from OB to Edgartown, rentals for bikes, etc....right in town. As well you can take the ferry right to Oak Bluffs and leave your car on the other side. You can walk to this rental from the ferry or take a very short taxi ride if you packed a pair of shoes for every outfit! I'm an ex New Yorker and I love it here! I love Oak Bluffs and I love this space. I

Located in Oak Bluffs, Massachusetts, United States. Oak Bluffs Cottage - A Short Walk to the Beach! Stay in this beautiful Vineyard home and enjoy a relaxing vacation back in time!Within 5 minutes of stepping out the front door and walking down the gentle slope above Sunset Pond, you'll stroll through the enchanted Historic Campground Cottages and past the Tabernacle on your way to the bustling main street of downtown Oak Bluffs.The historic house is lovingly crafted inside and out. Bright and airy with a skylight in the dining area and slider to a private back deck complete with outdoor shower and barbeque to rinse off and relax after a perfect day at the nearby beach.Quick 15 minute walk to a salt water beach. Amenities include a classic porch, patio with BBQ-grill, outdoor shower, washer&dryer, microwave, coffeemaker, cable TV, VCR or DVD. No pets / No smoking / No linensBeds / Baths:2nd Floor- King, Queen, 2 Twin / Full bath with tub onlyMain Floor- Queen / Full bath with shower only

Located in Oak Bluffs, Massachusetts, United States. Beautiful Custom Home In Oak Bluffs Discover 4 spacious bedrooms with well planned living space with a inviting porch that wraps around 3/4 of the house is certainly an added attraction with an intimate deck ideal for entertaining, dining, or just plain relaxing. Easy bike ride to town or walk to town, Sandy Beaches, Niantic Park, Oak Bluffs Harbor, Shopping, and Restaurants.

Located in Oak Bluffs, Massachusetts, United States. Eden House: Oak Bluffs Martha's Vineyard Discover Oak Bluffs in this centrally located cozy cottage, with a charming porch, well-appointed interiors, and a private backyard. Minutes from stunning beaches and Circuit Avenue, it's your ideal Martha's Vineyard retreat. Experience island living at its finest!Oak Bluffs on Martha's Vineyard is famous for its iconic Gingerbread Cottages, Victorian-style homes painted in pastel colors. It's beautiful beaches, like Inkwell Beach, provide opportunities for sunbathing and swimming. The harbor area features marinas and waterfront dining options. Circuit Avenue is the town's bustling commercial street with shops, boutiques, and the historic Flying Horses Carousel. Oak Bluffs also hosts events, such as the Monster Shark Tournament and the African American Film Festival. Outdoor enthusiasts can enjoy hiking, biking, and water sports. The town's history is reflected in sites like the Wesleyan Grove and the Methodist Tabernacle. At night, Oak Bluffs c