Vacation Rentals By Owner In Oak Bluffs, MA

$1291.39

Hideaway At Meadow View Farm/Private Tennis Courts with Spacious Bedrooms

Oak Bluffs, Massachusetts, United States

This Martha’s Vineyard Hideaway is nestled in the desirable Meadow View Farms area of Oak Bluffs, and includes access to the private association tennis courts. Three of the four bedrooms are super-spacious and have king sized beds and sitting areas.brbrThe first floor features an open layout with living, dining, and kitchen areas. The living area has sectional seating, chairs, and large screen TV. The kitchen is directly adjacent to the living area. It has a large center prep island/breakfast bar, and plenty of space for cooking. The dining area is just off the kitchen/living areas. There is a screened porch, with a couch and dining table, that is accessible through a door from the kitchen.brbrThe master bedroom, including an en suite private bath, and a bedroom with twin beds are also on the first floor, along with a private office and work area. Upstairs on the second floor, there is a large TV/family room with seating, large screen TV, desk, swivel chair and a sleeping alcove with a king-sized bed, plus a separate bedroom, and a shared bath. Both of the shared bathrooms have been re-tiled and updated.brbrThere's a porch with Adirondack chairs and benches for relaxation. The rear yard features a picnic table, gas grille and hammock and the side yard has Adirondack chairs.brbrThe Meadow View Farms Association tennis courts are just a short walk away from the house. There is a bike path is by the entryway to Meadow View, and Farm Neck Golf Club is nearby.brbrNOTE: Elevator not for tenant use.

Bed

Bath

Sleeps

$781.9

/ Nightly

Cottage

OB Cozy-Cottage-Glam off Circuit with Great Outdoor living

Oak Bluffs, Massachusetts, United States

Location!!! Location!!! This updated cottage is a quick walk to town, beach, Tony’s Deli, tennis and basketball courts, and so much more. Relax on the wrap around porch , enjoy the outdoor shower after a walk back from the beach, warm up near the fire pit while BBQ is on the grill. Walk to all downtown Oak Bluffs attractions. All new beds and furniture. Bring your fav sheets and bath towels to complete your comfort (Or rent locally on the island). Flexible work week. Work space for telecommuters.

Bed

Bath

Sleeps

$419.8

/ Nightly

Private Vacation Home

Downtown Oak Bluffs, short walk to beach & town

Oak Bluffs, Massachusetts, United States

Location, location, location. This cozy 3 bedroom house is located steps from downtown on a family neighborhood side street. Stroll among the Gingerbread houses, or into town for groceries, dining and fun...or pack a tote and stroll to the end of our street to Inkwell beach. Everything is within an easy walking distance, including the ferry, a great playground, fishing pier, lots of diverse restaurants and night spots, Flying Horses carousel, churches and shuttle buses that can take you around the island. brbrTransferable ferry reservations may be available to guests (at same price we paid + a $25 handling fee) for certain weeks of the summer. However, everything is so handy, you might not need a car. If you do want your vehicle on the island, there is off-street parking for two cars in front of the house.brbrThis quaint home features a living room with flat-screen TV, comfy sectional sofa, downstairs hardwood flooring, downstairs bathroom with shower, and 3 bedrooms and a small half bath upstairs. Queen bed in the master, double bed in the middle room, and 3 twins in the kids' room. The kids' room also has a TV in case you need to find a space for them to go and entertain themselves while the adults unwind after a day on the beach. There's also a TV in the master bedroom. There's a private hot/cold outdoor shower off the back porch too. The back patio features a canopy in case it showers during your stay - it's a pleasant place to have meals, play games or do a little bit of work in case it rains. BBQ on the private back patio or relax on the front porch and say Hi to the neighbors as they stroll by. brbrWindow air conditioners and fans, but for those cooler spring/fall evenings, there is electric heat upstairs and down.brbrPerfect for a family or a romantic getaway. This is a weekly Saturday-Saturday rental property however 4 night minimum stays may be considered during during parts of the fall.

Bed

Bath

Sleeps

$483.54

/ Nightly

Private Vacation Home

Spectacular Martha's Vineyard Island Home!

Oak Bluffs, Massachusetts, United States

This is our beautiful home on Martha's Vineyard we call Shangri-La! Spectacular setting with a great peaceful view overlooking Sengekontacket Pond with the ocean beyond. The property features a shared Pool, Tennis Courts, and a Dock. Our house is conveniently located midway between the Oak Bluffs & Edgartown town centers.brWhen the Presidents visit the Vineyard this is the area they come to relax (at Farm Neck Golf Club which is right up the street). The property overlooks the Felix Neck wildlife preserve.

Bed

Bath

Sleeps

$471.08

/ Nightly

Private Vacation Home

Serene Sengekontacket Pond Getaway

Oak Bluffs, Massachusetts, United States

The property is set among several private townhouses in a lovely neighborhood located off of Sengekontacket Pond in Oak Bluffs. The townhouse has clean, comfortable accommodations with all the amenities needed to ensure a relaxed vacation. There are 2 bedrooms, 2 baths, kitchen with granite counters, stove , microwave, dishwasher, toaster, blender, spice rack, keurig coffee maker, regular Braun coffee maker, and a well supplied kitchen. :There is a washer/dryer, free WiFi, cable, HD television,, and a large private deck with gas grill. The living room is furnished with a gas fireplace and a ceiling fan, and both bedrooms also have ceiling fans. br *There is Air conditioning for added comfort.brThe large deck offers added space for dining, grilling, and sunbathing. It is fun to sit out and watch the stars after dark.In addition to the private amenities, guests have access to the Association's two all-weather tennis courts, pickle board court,a fresh water pond, and a salt water pond for boating, and fishing. The location is conveniently along the bike trail and bus routes and is also near the Farm Neck golf course.

Bed

Bath

Sleeps

$1191.81

/ Nightly

Private Vacation Home

Beach, Town, Tennis, Pickleball - Central AC

Oak Bluffs, Massachusetts, United States

We will let the photos do the talking, but note that this home has some especially attractive features for large groups, such as bedrooms that allow for privacy due to access by 3 separate staircases. The newer kitchen has two refrigerators, two high efficiency washer/dryer units, and plenty of storage. Dining area has two tables that seat up to 16 people. There are a number of flat screen TV throughout the house. There is both private parking in back of the house for up to 3 cars, as well as on-street parking.brbrWith all that is new, there are still many historic touches that have been restored -- sliding panel doors with the original hardware in the living room, stained and leaded glass windows, and a funky 'Nantucket Bedroom' that is great for kids.brbrOutside you will find a large stone patio with gas grill and plenty of seating, along with access to the outdoor shower. Additionally, there is a shaded farmers porch, which is perfect for lazy Vineyard afternoons. Cross the street and you have access to tennis/basketball courts (we supply high quality tennis rackets and basketballs) and a playground. Take a few more steps and you are on Circuit Ave, surrounded by restaurants, shops, and nightlife. As for the beach and harbor (including ferry boats to the mainland), they are just a few scenic blocks away. brbrThis home is professionally cleaned and maintained year-round, and the owner has been renting out homes on the Vineyard for over 22 years. Feel free to inquire about the two-bedroom Edgartown home and the four-bedroom Oak Bluffs home. vrbo numbers 43322 and 59668.brbrKeywords: House

Bed

Bath

Sleeps

$642.28

/ Nightly

Private Vacation Home

Within Walking Distance to Town, Beach & Parks, Enclosed yard with a new deck,

Oak Bluffs, Massachusetts, United States

Located on historic Circuit Ave in Oak Bluffs within walking distance to town, beach, tennis courts and parks. Minutes away from shopping and restaurants. Handicap Accessible. Fully equipped modern kitchen. Large dining room, living room, and den / family room, gas/oil heat, all bedrooms air conditioned with quilts and pillows on each bed. I do not supply sheets and towels.

Bed

Bath

Sleeps

$958.87

/ Nightly

Cottage

Spacious Home - 1500 ft from Beach & Circuit Ave

Oak Bluffs, Massachusetts, United States

brNewly renovated four bedroom, two full bathroom home with an inviting front porch, private backyard and footsteps to Circuit Avenue. The first level has an open floor plan with the following: a new fully equipped eat-in kitchen, featuring tile floors and granite countertops; a 32-bottle wine refrigerator and a breakfast bar which seats three people. Also on the first floor is a queen-size bedroom, living room, dining room, family room with entertainment center, bathroom with stand-in shower, and a mudroom.brbrThe second floor room layout includes a master bedroom with a spacious sitting area perfect for reading, relaxing and napping, twin set bedroom, full-size bedroom, and bathroom. Take advantage of the private office/library room adorned with many books, novels and magazines for every reader. The inviting and comforting stone surfaces aren't just in the kitchen, but also included in each of the beach inspired bathrooms.brbrbrThis lovely summer home is walking distance to the beach, ferry, shopping and other attractions. It's a home away from home, and the perfect place for relaxation.

Bed

Bath

Sleeps

$1193.8

/ Nightly

Private Vacation Home

Newly Renovated! Walk to Town Oak Bluffs, 4 Bedroom/3 Bath A/C

Oak Bluffs, Massachusetts, United States

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.brbrFirst FloorbrThe 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 King bed, Flat Screen TV and a full bathroom that offers plenty of closet space, and a second bedroom with Queen Bed and Flat Screen TV. There is also another full bathroom. brbrSecond FloorbrWalk up the stairs to find yourself in a large open living area that serves as a second TV/ Media room with sectional sofa and Flat Screen TV. There are 2 additional large bedrooms with a full bathroom. One with 3 twin beds and the other with 2 twin beds.brbrBasement Recreation Room with Ping Pong TablebrbrBedroomsbrbrMaster (1st floor), King Bed, Flat Screen TV, Private BathbrbrSecond Bedroom (1st floor), Queen Bed, Flat Screen TVbrbr1st Floor Full BathroombrbrThird Bedroom (2nd floor), twin bed, twin bed, twin bedbrbr2nd Floor Full BathroombrbrFourth Bedroom (2nd floor), twin bed, twin bedbrbrbrOur home is located .5 miles from the hustle and bustle of downtown Oak Bluffs. This location is unique as you are a short walk or bike ride away from everything that Oak Bluffs has to offer, yet you far enough away to experience the peace and tranquility of the island. During the day enjoy shopping the boutiques along Circuit Ave, swimming in the ocean at the Inkwell Beach, strolling and dining along the harborside, then retreat back to the quiet solitude of our house. The walk to town is pleasant and safe, down residential dirt roads, easily avoiding major roads making it great if you are with kids! We are just a short distance to the County Road bike path, which connects to miles of island bike paths. brbrWe are situated 2 miles from the Vineyard Haven Steamship Authority Terminal and .7 miles from the Oak Bluffs Steamship Authority Terminal, the Island Queen and the Hyline Ferries.br

Bed

Bath

Sleeps

$515.26

/ Nightly

Private Vacation Home

Private Meadow View Family Retreat - 4 BR, AC, Large Yard, Tennis, on Bike Path

Oak Bluffs, Massachusetts, United States

Located in the desirable, private Meadow View Farms Estates, across from the Farm Neck Golf Club, this charmingly decorated, tranquil, four-bedroom property does not disappoint. Centrally located on the bike path and bus route, it is just a short distance to Oak Bluffs Center with easy access to Edgartown and the up-island roads to Chilmark and beyond. The house is 2 miles from the beach. Guests have access to private tennis and pickleball courts just steps away .brbrOur home itself is a peaceful island residence decorated with a mix of Arhaus, Safavieh, antiques, and other personal touches to make you feel at home and on island time the minute you arrive. There is a great flow for entertaining from the interior living space to the inviting deck and lovely screened-in porch.brbrFour bedrooms comfortably sleep 8: br• First floor master bedroom (queen) with en suite full bath. br• Second floor has three additional bedrooms (queen, queen, and two twin beds) and a second full bath.brbrbrNewly redone, fully equipped kitchen with stainless steel appliances. brbrMagical screened-in porch with comfortable lounge furniture and twinkling lights overlooking large, level lawn and beautifully landscaped grounds.brbrLarge deck with dining table that seats 8-10brbrFinished basement br• pool tablebr• comfortable seatingbr• 65 TVbr• bar with refrigeratorbr• half-bathroombr• separate laundry room with washer and dryerbrbrCentral Air ConditioningbrbrFabulous outdoor shower brbrBecause this is also our summer home, there are other helpful amenities:br• gas grillbr• beach chairs, umbrellas, coolers, and beach towelsbr• lawn games and board games brbrbrBed linens and bath towels not included – available for rent from local service. Many clients prefer to bring their own.brbrWe feel confident you will enjoy your summer vacation as much as we do.brbrSeven day minimum rental in summer.brbrSee rules for cancellation policy.brbrbrbrbrbr

Bed

Bath

Sleeps

$874.06

/ Nightly

Apartment

Perfect location! By Beach, Harbor & Town! Gorgeous Gingerbread Upstairs Aptmt

Oak Bluffs, Massachusetts, United States

July and August: Turnover day is generally Friday.brbrThis lovely, in-town, impeccably renovated 1800's historic Oak Bluffs upstairs apartment is adored by all who stay here. With original architectural details and a warmth brought forth by owner Sharon, the apartment is truly an oasis in the heart of Oak Bluffs.brbrThe apartment has a sunlit living room with beautiful breezes through many new windows flanking both sides, a kitchen, full bath with standing shower, and a lovely and spacious sunlit bedroom with meditation nook and skylight. brbrThe house is very special, with beautiful energy from all the wonderful people who have stayed there and graced its walls. Up to four people are welcome in this apartment. The living room has a very comfortable full size sofa bed. brbrQuiet hours are 9pm to 9am.brbrSurrounded by all the vibrant and colorful life of Oak Bluffs in every direction, there is never a need to commute into town for the island's most popular events. The August Fireworks, Illumination night, concerts on the park are all around the corner.brbrThe apartment is a very short walk along beautiful Ocean Park from the ferry, a couple of blocks from the islands exceptional transportation system, a couple of blocks to Inkwell Beach, a block from exceptional restaurants and bars, practically next door to performances at the Tabernacle or Union Chapel, a block from the Methodist Campgrounds with their spectacular and colorful historic Gingerbread houses, a few blocks from the Harbor with its magnificent sunsets and waterfront restaurants and nightlife, and the ice cream shops, arcade, movie theatres and live local music of Circuit Ave. The breathtaking bike path from Oak Bluffs to Edgartown, with water on both sides, begins just a few blocks from the house, and running and walking paths through nature trails are a short jog away. Oak Bluffs truly has everything, and in my heart is the jewel of Martha's Vineyard Island. brbrMost guests find this home to be a generally quiet oasis for being right in the center of town, but just a reminder that the house IS in the center of town, just not on the main shopping drag. ;)brbrOne more IMPORTANT thing for you dog owners:brWe LOVE dogs and this property is selectively dog friendly (sorry, no cats)! If you'd like to bring your doggo along, you must ask us first, so we can be sure you agree to our pet guidelines. THANK YOU!brbrHouse Story:brbrI fell in love with this house the minute I saw it. It took me a full winter to be able to be able to call it my own, because when I made the offer the owner was concerned about disappointing someone else, though they had was no contract at all. She was so kind, she spent a few months trying to find this person, who was out of the country and difficult to track down. In the meantime, she knew how much I loved the house, and after several long months she called to say it was mine if I still wanted it, and I could take a few days to let her know. I told her I didn’t even need a few minutes. No other house that I had seen captured my heart as this one had. brbrIt took great amounts of work to prep this house to be my massage center, as it would be for some years before I could make it my home. One day, at my other massage center in Vineyard Haven, I interviewed a lovely massage therapist from Louisiana. I had no idea she had MV ties, but I instantly adored her and her work and hired her on the spot and sent her here to do a massage. Twenty minutes passed, and the phone rang. “You are not going to believe this, Sharon, but this is the house my grandmother grew up in.” brbrOma (grandmother in German), came right over the next day from West Tisbury, where she then summered, brought me this photo of her parents and this house as it was in 1908, and gave me a tour of the house, telling me where all the original details used to be. Oma was beautiful, and her granddaughter is beautiful, as was the previous owner. I just kept feeling that it was no wonder that it feels so special in here. Since that time, my friends, family and guests have only added to that feeling. Time and time again, people walk in and comment on the energy of the home. I feel it deeply myself.brbrTo top off all of this wonder, the last bit of amazement for me was the dog in the photo - a dog with a half black and half white face, split down the middle. On the other side of the couch, you can see the photo of my dog, Haffa, at the time. A dog with a half black and half white face, split down the middle, almost 100 years later.brbrLife is magical, mysterious and beyond imagination.brbrIf these dates are not available, please send us a message. We have other beautiful properties.brbr(Please note: We do have a guest-centered and considerate cancellation policy. Please see our attached cancellation policy for details.)

1

Bed

1

Bath

4

Sleeps

$1060.03

/ Nightly

Private Vacation Home

Charming Vacation Home in Oak Bluffs.

Oak Bluffs, Massachusetts, United States

Just a stone away from Oak Bluffs and its beaches, this chic 4 bedroom home provides comfort and privacy. The large bedrooms and open concept kitchen/dining/living area accommodate up to 8 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 are home.

4

Bed

2

Bath

8

Sleeps

$681.35

/ Nightly

Private Vacation Home

Lovely 3-bedroom house with AC in Oak Bluffs within 15 min walk to Circuit/Beach

Oak Bluffs, Massachusetts, United States

Some vacation rentals are just a place to sleep. Casa Luca is the kind of place you’ll talk about on the drive home, already planning when you can come back.brbrTucked away on a quiet, private dead-end road in Oak Bluffs, this sun-filled three-bedroom retreat strikes the perfect balance: you’re close to everything the Vineyard has to offer, yet the moment you turn onto that shaded dirt road, the outside world melts away. It’s the kind of neighborhood where kids can run freely in the yard, where the pace slows down, and where a vacation actually feels like a vacation.brbrThe SpacebrStep through the front door and the open layout immediately puts you at ease. The fully equipped kitchen flows into the living and dining area, a natural gathering place where someone can be cooking while everyone else is catching up at the table. There’s a Smart TV for movie nights and cozy couches, but honestly, you’ll spend most of your time in the gorgeous sunroom, everyone's favorite spot.brThe sunroom is the heart of this home. Flooded with natural light (even on grey winter days, past guests say it glows), the sunroom is where morning coffee becomes a ritual, where board games stretch late into the afternoon, and where you’ll find yourself just sitting and breathing. It opens directly onto the back deck, which is outfitted with a gas grill and a dining area, making the transition from indoor to outdoor completely effortless. Fire up the grill, pour a drink, and settle in.brbrThe yard is spacious, with an outdoor shower (a quintessential Vineyard touch) is perfect for rinsing off after the beach. The whole outdoor setup is designed for people who actually want to use it.brbrThe BedroomsbrCasa Luca sleeps seven across three comfortable bedrooms all on one level, a thoughtful detail that makes the house exceptionally easy for families with young children. The king room offers a peaceful, grown-up retreat. The queen room is bright and comfortable. And the bunk room The kids will call dibs immediately. A full-sized sofa bed provides extra flexibility if you need it, and a travel crib is available for the littlest guests.brbrAll beds are made up with fresh, all-cotton sheets — soft, breathable, and a small luxury that makes a real difference after a full day out.brbrThe Details That MatterbrbrWe as owners have genuinely thought things through. Beach chairs are provided so you don’t have to lug your own on the ferry. The kitchen is stocked with all the cookware, dishes, and utensils you need to make real meals — breakfast every morning, dinner whenever you feel like staying in. There’s a washer and dryer so you can pack lighter than you think. High-speed internet and A/C keep everyone comfortable. The home is eco-minded too, with LED lighting, recycling, and scent-free soaps and detergents throughout.brPets are welcome — $75 per dog — so the whole family can make the trip.brbrThe LocationbrOak Bluffs is one of the Vineyard’s most beloved towns, and Casa Luca puts you right in the thick of it, without the noise. Circuit Avenue, with its restaurants, boutiques, ice cream shops, and the iconic Flying Horses Carousel (the oldest platform carousel in America), is just a mile away, an easy walk or a quick bike ride. Oak Bluffs Town Beach and the Inkwell is 1.2 miles from the door. The ferry terminal is a short drive, making arrival and departure day genuinely stress-free. Downtown Vineyard Haven is about ten minutes away.brbrWhether you’re here for a summer week of beach days and lobster rolls, a spring long weekend of hiking and exploring, or a cozy off-season escape when the island is quiet and all yours, Casa Luca is ready for you.

Bed

Bath

Sleeps

$502.65

/ Nightly

Private Vacation Home

Your Vineyard Dream Vacation - OAK BLUFFS -Sunny Open Floor Plan Close to Town

Oak Bluffs, Massachusetts, United States

A BEAUTIFUL PROPERTY CLOSE TO TOWN-GREAT PRICE! LOTS OF PRIVACY BUT CLOSE TO EVERYTHING IN OB.brbrONE WEEK MINIMUM FOR ALL PEAK SEASON RENTALS (JULY - LABOR DAY)brbr**PLEASE NOTE BEFORE BOOKING: WE DO NOT SUPPLY SHEETS OR TOWELS. All beds have comforters, blankets and pillows**brbrbrLife is a dream on Dreamer's Way - This very clean, comfortable, updated home with an open concept layout and plenty of windows for sunlight is located on a quiet, private street close to the fun of Circuit Ave. (10-15 minute walk). brPlease read our reviews to find out why guests say our house is the perfect gathering place for family and friends. Tastefully decorated rooms, a spacious deck with wrap around bench and dining table, chairs are adjacent to a wonderfully spacious, custom outdoor shower w/changing area are a few of our guests' top favorite things about the house. brbrThe kitchen is convenient to the back deck via sliding doors that overlook a large, private backyard and wooded area. brbrAMENITIES & EXTRAS:br- Wi-Fibr- 50'' flat screen mounted TV with cable/DVD/Blue Ray/Roku and streaming access in living room br- 32 TV in denbr- Weber gas grill br- Fully equipped kitchen (appliances, cookware, Kitchen Aid mixer, dishes, cook's tools & lobsterware) br- 8 beach chairs, also beach umbrella, sand toys and other outdoor/beach itemsbr- Information Binder (recommendations personally compiled by owners)br- A/C units in all bedrooms (these12,000 BTU units cool the entire house!)br- Friendly, prompt and helpful Property Manager.brbrLOCATION, LOCATION, LOCATION!brbrAddress: 10 Dreamer's Waybrbr- 10 minute walk (.7 of a mile) to the famous gingerbread cottages and Arts District br- Close to Tony's Market in the Arts District (groceries/package store)br- 10 minute walk to Vineyard Ave Extension-Lagoon small beach/launch area br- 15 minute walk or quick bike ride (one mile) to downtown Oak Bluffs, Inkwell Beach, Jetty Beach, Flying Horses Carousel, Ocean Park, ice cream, Back Door Donuts, shopping, dining, town tennis courts, basketball courts & playground.

Bed

Bath

Sleeps

$624.92

/ Nightly

Private Vacation Home

Private setting nestled in the heart of East Chop.

Oak Bluffs, Massachusetts, United States

Great East Chop (Oak Bluffs) location! Take morning walks on world famous East Chop Drive, or watch the sunset from there in the evening. Enjoy lively downtown Oak Bluffs, just one mile from the house. Close to beaches - just 1.5 miles to Inkwell Beach and 1.2 miles to Eastville Beach. Enjoy the second story deck to have coffee and watch the birds, or to enjoy an evening drink.brbrThe house is situated on a nearly one acre private, wooded lot. It's an upside down house - the main living area, main bathroom, main bedroom (deck access), and large deck are upstairs. Secondary bedrooms, a common room, and small bath are downstairs. There is also a nice, new outside shower, as well as a new front deck downstairs. The large, completely open, great room (living room, kitchen, dining room) with cathedral ceiling and two new skylights and the deck are where you'll hangout when you're not enjoying all that Oak Bluffs - and the rest of the island have to offer.brbrAs the bedrooms are currently set up (stay tuned), we recommend a maximum of 4 adults, 3 if you're all single. PLEASE NOTE: Linens and towels are not provided. Pillows and blankets are provided.brbrThe kitchen is fully equipped. There is a smart TV upstairs and Wi-Fi is provided. There is air conditioning (and heat) with newly-installed mini-splits in the great room and master bedroom. There are fans only in the generally much cooler downstairs. There is also a brand new washer and dryer downstairs.brbrOriginally built in the early 70s, this is just a basic house, not a luxury hideaway. It’s a fantastic location from which to enjoy all the island has to offer. Great for an active couple or family! I've spent many mornings on the deck getting ready for an adventure and then relax there afterwards in the evening. In fact, I'm here right now on a June evening on the deck and an osprey just hovered overhead. East Chop is filled with dirt roads to walk or bike. Walks to Crystal Lake and the East Chop Lighthouse are a must! Book your stay today!

Bed

Bath

Sleeps

$445.41

/ Nightly

Guest House

The Sweetest Suite – Beach, kayaks & Starry Nights

Oak Bluffs, Massachusetts, United States

Welcome to your perfect island escape. Tucked beneath a canopy of soaring 70-foot trees, our charming guest suite offers privacy, comfort, and a truly special sense of place. Whether you're here for a romantic getaway, a weekend with a close friend, or a solo retreat to recharge, this space is designed to make you feel at home the moment you arrive.brbrYou'll have your own private entrance and a peaceful setting just steps down a picturesque dirt road to a secluded beach — perfect for sunrise walks, afternoon swims, or quiet evenings by the water. For those who love to explore, we’re right off the bike path that leads straight into the heart of Oak Bluffs, with its vibrant shops, restaurants, and classic island charm.brbrInside, the suite is light-filled and thoughtfully designed for two. It includes a cozy sleeping area, a well-equipped kitchenette for light meals, a private full bathroom, and a brand new outdoor shower that lets you rinse off under the sky. Enjoy your morning coffee or evening wine on the private patio, surrounded by tall trees and birdsong — a peaceful haven you may never want to leave.brbrYou'll also have fast Wi-Fi and a smart TV for streaming, so you can stay connected (or unplug completely — your call).brbrWhat makes this space truly special is its balance: close to everything, yet wonderfully tucked away. It’s cozy, bright, and welcoming — a little forest retreat by the sea.brbrWe’d love to host you.

Bed

Bath

Sleeps

$692.54

/ Nightly

Private Vacation Home

Adorable Oak Bluffs Cottage With Ac On East Chop

Oak Bluffs, Massachusetts, United States

Adorable 4 bedroom cottage in the East Chop neighborhood of Oak Bluffs. You will love the beautiful back yard that has a patio and sizable garden and is very private. There is a large screened porch for entertaining. Inside are four comfortable bedrooms. One is a master bedroom with a Queen bed, a bedroom on the first floor with a garden view and a queen bed, one room on the second floor with a double bed and another on the second floor with two twin beds. There are two full baths plus an outdoor shower. Other amenities include central AC, dishwasher, washer/dryer, cable TV, Internet, and a BBQ grill.brbrThe location is wonderful, a short walk to the beach and to the center of Oak Bluffs, where you will find shopping and many dining options. Access to the VTA shuttle is also very close, providing transport all over the Island. This house is in a perfect setting.

Bed

Bath

Sleeps

$480.31

/ Nightly

Apartment

The Nest, Comfortable, Cozy and Convenient

Oak Bluffs, Massachusetts, United States

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!

Bed

Bath

Sleeps

$1219.0

/ Nightly

Private Vacation Home

Luxury Loft Historic Center Oak Bluffs

Oak Bluffs, Massachusetts, United States

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.brbrThe 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. It feels like Tribeca but is 2 blocks to beautiful clean ocean at inkwell beach.....!brbrKeywords: luxury, chic, contemporary, designer, spacious,

Bed

Bath

Sleeps

$957.83

/ Nightly

Cottage

The Island Collection MV: Charming Cottage Located In Heart Of Oak Bluffs

Oak Bluffs, Massachusetts, United States

Enjoy a relaxing ferry ride to Oak Bluffs and its picturesque surroundings. Once your ferry ride ends, you’re steps away from home! Your vacation stay will be unforgettable in this charming cottage located in back of the elegant, enchanting, and historical bright yellow Victorian home, which was built in the 1950s. Speaking of ocean views….enjoy the benefits of having an ocean view steps away from your back yard! Being on vacation in Martha’s Vineyard in the heart of down town on a main street has its privileges! As the cottage is located on the main street, Kennebec Avenue, you can see the entire ocean; only a stone’s throw away from this lovely fully furnished cottage, which has 2 full bedrooms, 2 full private bathrooms (upstairs), and 1 powder room (located on the main level). The cottage comfortably sleeps four people; two couples or a family of four. There is one parking space available to you next to the cottage on the property. While sitting in the back yard sipping on your favorite glass of wine, enjoy a lovely meal you have prepared on the gas grill which is available to our guests. The cottage is available for year round rental with central air and central heat for your convenience.brbrOn the first floor of the cottage, relax and enjoy the living room and dining area (which comfortably seat four), a newly renovated kitchen, and a powder room. On the second floor there are two bedrooms. The first bedroom is furnished with a queen bed and a full private bath. The second bedroom is furnished with 2 double beds and a full private bath. Both bedrooms are furnished with all new mattresses. This lovely cottage has all new appointments such as: a new kitchen, new bathrooms, all new furniture, an entirely furnished home, central air and central heat. The cottage is also freshly painted. Cable television, wireless Internet and phone are available to our guests.brbrConveniently located steps away from the ferry, this striking cottage is only 100 feet away from the beach. As the cottage is located in town, you are close to quaint downtown shopping, night life, restaurants, churches, parks, hiking and bike paths and trails, deep sea fishing, car, bike and motor cycle rentals. Enjoy a tour around the island by way of public transportation (the bus stop), or taxi.brbrSteps away from your back patio immerse yourself in the beautiful ocean view, which includes a park and gazebo where you can witness people getting married and feel their joy of beginning their lives as one. Listen to various genres of music in the park performed by local and national bands. Watch fireworks from the back yard of the cottage. Witness the uplifting excitement of experiencing people flying kites or indulge in this activity for your own pleasure. Directly across the street from the cottage is the grocery store. For breakfast, after a fun day at the beach, touring, and shopping, or for late night snacking, indulge and treat yourself to some hot, fresh, and sweet donuts that are a hit with the locals. Back Door Donuts is open from 7 p.m. – 1:00 a.m. You’re sure to remember this treat!brbrAs you can see, there is no need for a car…you’re in Oak Bluffs, where the action and night life are only a short walk away! After a long day at the beach, shopping, dining, and fun, you’re steps away from home! We look forward to seeing you!brbrWe adhere to the customs for home rentals on the Vineyard, which do not include linens (sheets, pillowcases, towels, or beach towels) as a part of the rental experience. Please arrange to bring your own linens or visit http://takemmylinenrental.com to place an order for your linen rental. br2nd Fl 1Queen, 2nd Fl 2 Doublebrbr

2

Bed

2

Bath

4

Sleeps

Vacation Rentals By Owner In Oak Bluffs, MA

$1291.39

$781.9

$419.8

$483.54

$471.08

$1191.81

$642.28

$958.87

$1193.8

$515.26

$874.06

$1060.03

$681.35

$502.65

$624.92

$445.41

$692.54

$480.31

$1219.0

$957.83

Rent a place that suits your needs

Most popular vacation rentals in Oak Bluffs

$2204.99

$2226.16

$2960.05

$3015.90

$3248.61

$3591.16

$3725.20

$1108.69

$1076.68

$1076.81

Most Popular Cities in Massachusetts