Vacation Rentals By Owner In Oak Bluffs, MA

Welcome to your perfect Martha’s Vineyard getaway! Nestled in the heart of Oak Bluffs, this charming 3-bedroom home offers the ultimate convenience and comfort. Located just above Sunset Park, you`ll be steps away from Oak Bluffs Marina, Circuit Avenue, Inkwell Beach, East Chop Beach, the Campground, and Ocean Park. With easy access to State Beach and the surrounding towns, this is the ideal home base for your island adventure.brbrNestled above Sunset Park, this beautifully updated home offers the perfect Martha’s Vineyard retreat. Enjoy a bright, open-concept living space, modern comforts, and an unbeatable location just steps from Oak Bluffs Marina, Circuit Avenue, Inkwell Beach, East Chop Beach, the Campground, and Ocean Park. brbr• BEDROOMS •brBedroom 1: Queen bed brBedroom 2: Queen bed brBedroom 3: Two twin beds – great for kids or friends brSleeps up to 6 guests comfortably brbr• BATHROOMS •brFirst-floor bathroom: Full bath with a bathtub brSecond-floor bathroom: 3/4 bath (sink, toilet, and shower)brPrivate outdoor shower Perfect for rinsing off after the beach (seasonal) brbrKey Amenities Include:brFully equipped kitchen with a gas stove, microwave, dishwasher, and all toxic free cooking essentials.brWasher & dryer for your convenience.brCentral heating and cooling for year-round comfort.brFresh linens, and bathroom essentials (shampoo, conditioner, and body soap).brOutdoor deck with a dining table and chairs, perfect for relaxing or enjoying meals al fresco.brPrivate enclosed outdoor shower, ideal after a day at the beach.brFree parking on the premises.brHigh speed internetbrbrbr• SHEETS/BEDDING PROVIDED•brSheets set for bedbrPillows brExtra SheetsbrBlankets/ComfortersbrKitchen Towel brBathmatsbrbrONLY BEDDING IS PROVIDED; TOWELS ARE NOT PROVIDED; YOU MUST BRING YOUR OWN TOWELS or rent your own towels. brFor towel rentals contact (A )Martha’s Linen Rental Or (B)Take My Linen RentalsbrKITCHEN & DINING •brFully equipped kitchen with gas stove, microwave, dishwasher, and all essential cookware brDining area perfect for shared meals and gatherings brCoffee maker for your morning brew br• LIVING AREA •brOpen-concept space filled with natural light brSmart TV and high-speed Wi-Fi for entertainment brCentral air conditioning and heating for year-round comfort brbrOutdoor Space:brStep into the back garden, where you’ll find a peaceful deck, perfect for enjoying morning coffee or evening cocktails. Whether you`re soaking up the sun or dining outdoors, this space is designed for relaxation.brWhy You’ll Love Staying Here:brPrime location: Walk to Oak Bluffs’ iconic attractions, including beaches, parks, and vibrant Circuit Avenue.brFamily-friendly amenities: Safe, spacious, and thoughtfully designed to accommodate groups of all sizes.brUnwind in style: Comfortable furnishings, modern updates, and cozy spaces make this your home away from home.brbrGuest Access: The guest will have access to the whole property except for a locked closet and doors. brOur property management team (Elevate Properties) will be available for any concerns or questions you may have.brbrOur property management team (Elevate Properties) will be available for any concerns or questions you may have.brbr• HOUSE RULES •brPETS: This property is not pet-friendly. Unauthorized bringing of pets will have a penalty of $300 which will go towards a deep cleaning of the property. brbrCHECK-IN: Check-in time is after 4PM. Early check-in requests are subject to availability and cannot be guaranteed. If we`re able to accommodate an early check-in, there`s an early check-in fee of $50 starting at 1 PM. Please check the availability of early check-in prior to booking.brbrCHECK-OUT: Check-out time is before 11AM. We do not allow late check-out as we schedule cleaning ahead of time. Any unauthorized late check-out will result in a charge of $50 for every 30 minutes.brbrSMOKING: We do not allow smoking inside the property or outdoor spaces including the balcony and terrace. There is a smoking fine of $300 if there is evidence of smoking inside the property.brbrNOISE: Please observe quiet hours after 10PM. Please be mindful of the neighbors as this property is situated in a quiet neighborhood. If the police are summoned due to noise complaints, this warrants a possible eviction with no refund.brbrDAMAGES & LOSS: I would truly appreciate it if you could treat our home like yours. You will be responsible for any damages or loss in the property which will be deducted from your security deposit. Please advise me of any damage or loss immediately upon discovery.brbrUNAUTHORIZED GUESTS: Please make sure to book the property for the correct number of guests. Parties, events, or any kind of gathering are prohibited. Given the COVID-19 situation, no other guests outside the reservation are allowed on the property.brbrPHOTOSHOOT/MUSIC VIDEOS: This property is for residential use only and not for commercial purposes without the written permission of the owner. Please contact us directly for booking of events. brbrREQUIRE STAIRS brA small set of stairs to enter the house. brbr• ADDITIONAL NOTE •br- Please be advised that a pre-check-in form will be required prior to check-in.br- Please acknowledge the house rules upon booking.br- ONLY BEDDING IS PROVIDED; TOWELS ARE NOT PROVIDED; YOU MUST BRING YOUR OWN TOWELS brDISCLAIMER: Due to the Summer season, we have a landscaper scheduled to come over to the property weekly. Please expect a visit during your stay. However, they are only going to access the lawn or the outside area of the property.br.br HOUSE RULESbr• PETS: The home is not a pet-friendly property. The unauthorized bringing of pets will have a penalty of $300 which will go towards the deep cleaning of the property.brbr• CHECK-IN: Check-in time is after 4 PM. Early check-in requests are subject to availability and cannot be guaranteed. If we`re able to accommodate an early check-in, there`s an early check-in fee of $50 starting at 10 AM. Please check the availability of early check-in prior to booking.brbr• CHECK-OUT: Check-out time is before 11 AM. We do not allow late check-out as we schedule cleaning ahead of time. Any unauthorized late check-out will result in a charge of $50 for every 30 minutes.brbr• SMOKING: We do not allow smoking inside the property or in outdoor spaces including the balcony, backyard, and terrace (if applicable). There is a smoking fine of $300. brbr• BBQ GRILL: Extra charge of $100 will apply for not cleaning after using the BBQ Grill.brbr• NOISE: Please observe quiet hours after 9PM. Please be mindful of the neighbors as this property is situated in a quiet neighborhood. If the police are summoned due to noise complaints, this warrants a possible eviction with no refund.brbr• DAMAGES & LOSS: We would truly appreciate it if you could treat our home like yours. You will be responsible for any damages or loss to the property which will be deducted from your security deposit. Please advise us of any damage or loss immediately upon discovery.brbr• UNAUTHORIZED GUESTS: Please make sure to book the property for the correct number of guests. Parties, events, or any kind of gathering are prohibited. Given the COVID-19 situation, no other guests outside the reservation are allowed on the property.brbr• PHOTOSHOOT/MUSIC VIDEOS: This property is for residential use only and not for commercial purposes without the written permission of the owner. Please contact us directly for booking of events. brbr• LOST AND FOUND: Please note that all shipping is at the traveler`s expense. There is a minimum $25 shipping cost plus a $50 service fee. We are not liable for any lost items. Our team will do our best to locate your lost items after check-out. We do not allow any mail deliveries or packages during your stay.

Charming 3-Bedroom Home in the Heart of Oak Bluffs

Oak Bluffs, Massachusetts, United States

Bed

Bath

Sleeps

$1455.46

This is an original Pratt house built in 1866 by the famed architect Pratt for whom the Pratt Institute in New York was named. It is located in the historic district across from a large park in which baseball, golf practice, kite flying, bike riding, picnics and even, on at least one occasion, horseback riding was practiced. The house has a water view which includes and is across the street and only steps from the famous Inkwell Beach. On a clear day, as most are in this location, you can see from the large porch, the beaches and down the coast all the way to Edgartown. It is also just a short 3 block walk to town and its many shops, family concerts, restaurants, festivals, art galleries, antique shops, the carousel, the arcade, as well as to the Oak Bluffs ferry. It is a shorter walk to the basketball and tennis courts.

Original Pratt House built in 1866 with Ocean View of the Inkwell beach.

Oak Bluffs, Massachusetts, United States

Bed

Bath

Sleeps

$1549.84

Retreat to Martha's Vineyard in a modern ranch style vacation home with a heated pool tucked on 1.5 acres of landscaped grounds providing the ideal setting for families and friends to enjoy their time together.brbrOur home offers multiple spaces to relax inside and out, ensuring everyone’s vacation needs are met. The grounds offer an exceptional park-like setting with grassy lawns, various walking paths, and a koi pond. The home is located in a quiet neighborhood near the Lagoon Pond in close proximity to Farm Neck Golf Club and Featherstone Center for the Arts.brbrThe pool anchors the extensive exterior entertainment area, surrounded by decks, walkways, and brick patios, awaiting your dream vacation.brbrThe house features four comfortable bedrooms, 2.5 baths and can accommodate 9 guests. An open-concept kitchen and dining areas, spacious living room, office, and exercise room...all on one floor with multiple access points to the expansive deck. There are many amenities, including central air conditioning, Wi-Fi, linens, a pool with a diving board and lounging spaces, an outside shower, games, a pool table, and many more…brbrThe spacebr• Main bedroom suite king bed, full bathroom, dressing closet with access to the deckbr• Queen bed with access to deckbr• Two XL twins can be converted into a kingbr• Two twin bedsbr• Additional sleeping space for one (daybed)brbrNo pets are allowed. The property is strictly animal-free because the owner has severe allergies

Retreat to Martha's Vineyard with a Private Pool & Outdoor Living in Oak Bluffs

Oak Bluffs, Massachusetts, United States

Bed

Bath

Sleeps

$1061.15

This property has something for the whole family to enjoy. A large wrap-around porch, screened in dining area on side porch. Outdoor seating and grill make outdoor living enjoyable, while a spacious living room, full kitchen, cable TV, DVD and game closet make indoor living fun as well. The basement was finished in 2024 with additional living area and TV. Beautiful blue stone patio in the back which is private and perfect for evening cocktails or dinner or just lounging and reading a book. Located at the end of Oak Bluffs' main street on Penacook Ave (the website map is incorrect), there is easy access to amazing shopping and many dining options without a lot of noise and congestion. Down the street is the famous Inkwell Beach perfect for an afternoon nap, or a full day of sun and surf. Public transportation and bike paths all over the island make cars convenient but not necessary, and beautiful scenery makes walking pleasant as well. Oak Bluffs offers the best of the Island from the famous Mad Martha's Ice Cream, Black Dog Store, Giordano's Italian Restaurant, and Flying Horses Carousel. An arcade and night clubs offer many entertainment options, and water sport rentals offer fun filled days on Martha's Vineyard for everyone. PLEASE NOTE LINENS AND TOWELS ARE NOT PROVIDED

Cottage

Completely renovated, air conditioned cottage close to the beach. Dog friendly.

Oak Bluffs, Massachusetts, United States

Bed

Bath

Sleeps

$577.21

Please note - If you are considering bringing your pet, one small dog may be considered, but we ask that you send an initial “inquiry” first and tell us a little bit about him/her, as pets require homeowner's written approval and guest’s agreement to homeowners’ pet rules. An additional pet fee will apply if approved. Thanks!brbrAlso note - Vrbo may indicate there are 2 bathrooms - there are not. We have 1 full bathroom and an additional “outdoor” shower in the 3-season enclosed back porch.brbrAbout our cottage: With Eastville Point Beach less than a mile away, this comfortable and charming single-family cottage is ideally situated for easy access to everything the magical island of Martha's Vineyard has to offer. The bike path and bus route are about 100 ft from the front door, and the cottage is conveniently located almost exactly midway between the bustling down-island town centers of Vineyard Haven and Oak Bluffs. Bring your own bikes and kayaks or rent them from nearby outfitters in Vineyard Haven or Oak Bluffs. brbrAn interesting tidbit about our cottage is that it was owned by the author bell hooks for many years, and was where she stayed when visiting Martha’s Vineyard. Some of her furnishings remain as part of the cottage’s decor today. brbrThe cottage's amenities, furnishings and decor are selected for comfort and easy vacation living any time of the year. Fully insulated, the cottage is equipped with window ACs in living areas and both bedrooms to keep the whole house cool in summer, and multi-zoned thermostat-controlled baseboard electric heat to keep you cozy warm in cooler months. The home offers one-floor living with 2 private bedrooms, each with its own closet, a full bath off the hallway with tub/shower combo, open concept kitchen, dining, and living spaces, a spacious front deck, and a fully enclosed 3-season back porch. With an additional outdoor shower, outdoor grill, well appointed kitchen, reliable WiFi, and washer/dryer, there is everything you need for a wonderful Vineyard getaway or working vacation. Kitchen, living, and dining areas may be closed off from bedrooms offering enhanced privacy for early-to-bedders or late risers. Two bedrooms, one with a queen, the other with two twin beds, comfortably accommodate 4. The 3-season back porch has garden-style furnishings, a ceiling fan, and table seating, and is the perfect spot to enjoy a game of cards or a cup of tea and a good book with a view of the wooded rear yard. brbrHaving a car will offer the most flexibility for getting around the island, and is recommended. The cottage is just a short drive to the town centers and ferry terminals of Oak Bluffs (1.6 miles) and Vineyard Haven (2.0 miles). Nearby Eastville Point Beach is 0.9 miles from the cottage. There is ample off-street parking on the property for 1-2 vehicles. Also, the bike path and VTA bus route are close by, and offer alternate transportation options if you choose not to bring a car. It should be noted that while the bike path enhances safety for cyclists and walkers where present, it is not continuous everywhere. Cyclists and walkers should be prepared to navigate the roadways at times. VTA buses have bike racks for bringing bikes to especially rideable spots on-island. Off-road motorized vehicles such as dirt bikes, quads or ATVs are not allowed on the property.brbrThe nearest full-size grocery stores are located in Vineyard Haven (Stop & Shop on Water St.) and Oak Bluffs (Reliable Market on Circuit Ave.). Tony's Market in Oak Bluffs, Our Market in Oak Bluffs, and Cumberland Farms in Vineyard Haven offer essentials and a limited grocery selection. Vineyard Grocer and Cronigs Markets on State Rd. in Tisbury and West Tisbury offer upscale and specialty grocery options.brbrA note about fees and taxes: For their services, Vrbo charges us, as hosts, a fixed fee plus a percentage of our listed rates and fees for each booking, and they charge you, the guest, a percentage of these rates and fees too. Taxes are also collected from you by Vrbo. For our location, the total lodging tax you will pay is an additional 11.7% of your total charges. Regarding our cleaning fee: We charge a fixed cleaning fee per stay as every cleaning covers the same territory whether a guest stays for 2 days or 2 weeks. If you would like a breakdown of our cleaning fee and what it covers, please don’t hesitate to ask. To avoid undue wear and tear on the cottage and to be able to keep our check-in and check-out times as accommodating as possible, there are a few simple tasks we ask you to complete prior to departing our cottage at the end of your stay. We ask you to leave your dishes washed, personal food items removed from the fridge, and your trash bags tied and deposited into the outside trash barrel. If you use the washer and dryer for your own personal laundry needs, we ask that you clean out the lint trap in the dryer after each load as a standard safety practice. We do ask you to keep the house reasonably tidy during your stay, and for security and safety reasons, we ask you to close and latch/lock all windows and doors, and turn off the lights, tv, and appliances when departing. We are more than happy to make reasonable accommodations for guests who are unable to, or prefer not to, complete any of these requested tasks - please feel free to discuss this with us.brbrPlease review the cancellation policy in place for this property before booking. We strongly recommend that our guests purchase separate travel insurance to protect themselves against the possibility that they may need to cancel after Vrbo's full-refund deadline has passed.

Cottage

Arrowsmith Cottage - Oak Bluffs - 1 mi to Eastville Point Beach via bike path.

Oak Bluffs, Massachusetts, United States

Bed

Bath

Sleeps

$332.81

brbrBuild in 2020 ! New lovely studio apartment.brClean, bright and comfortable.br700 sq feet !brGreat for couples, work trips, weddings.brbr*MONTHLY RATES AVAILABLE FOR OFF SEASON MONTHS *brbrThe spacebrbrOur new studio is located above the garage attached on the side of the main house.brPrivate entrance.brbrThere is a small outdoor deck on top of the stairs to the studio.brbrThe interior offers high ceilings, A/C, TV, wifi, cute kitchen, and lots of light. There is a queen sized bed and sofa.brbrbrbrbr•Bike to town, the harbor, restaurants, shopping, Flying Horses carousel, and the arcadebr•Easy drive to State Beachbr•10 minutes from the ferrybrbrbrNEIGHBORHOOD brbrOak 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 Ocean Park with the iconic gazebo which sponsors live musical events. There are many choices for beaches from Inkwell to Eastville. Oak Bluffs hosts many beloved Island events; Illumination Night, Fireworks, Built on Stilts, Harbor Festival, and Tivoli Day. Rain or shine there's plenty to do when you visit Oak Bluffs.brbrbrOther things to note-brThe owners and their dog live on the property and running small business out of home. brWe are available for you as needed.brHowever, we promise total privacy while you are on vacation.brbrThe check-in is at 4 pm OR LATER . brNOT possible earlier as we work hard to clean and disinfect !brbrThere is absolute NO smoking and PETS on the property.brThere is NO extra guests allowed or interacting with on our property.brbr!!We strongly suggest to purchase a travel insurance !!

Apartment

Discover the magic of Martha’s Vineyard! NEW ! Build in 2020 !

Oak Bluffs, Massachusetts, United States

Bed

Bath

Sleeps

$933.21

Escape to this beautifully updated 3-bedroom home, just 500 feet from Lagoon Pond—perfect for swimming, kayaking, and paddleboarding. Ideally located only 1.5 miles (or a 5-minute drive) from Oak Bluffs Center, Inkwell Beach, the harbor, and downtown, this home offers the perfect blend of relaxation and convenience.brbrThe open-concept main living area features a fully equipped kitchen, spacious dining area with a large gathering table, and a comfortable living room with an expansive sectional and wide-screen TV—ideal for family time or winding down after a day at the beach.brbrAlso on the first floor is a cozy den/office with a built-in desk, comfortable seating, and a small TV. The home offers high-speed internet and Hulu Live TV throughout. Two first-floor guest bedrooms include one king bed and one queen bed, along with a full bathroom featuring a tiled shower and a washer/dryer combo.brbrUpstairs, the private primary suite offers a king-sized bed, TV, seating area, walk-in closet, and a luxurious ensuite bathroom with a jetted soaking tub and a spacious walk-in shower.brbrThe finished basement provides additional living space with a queen sofa bed, large-screen TV, and room for lounging or recreation.brbrOutdoor living is a highlight, with grassy front, side, and back lawns, a brick patio with a wood-burning fireplace, front and side decks, a Weber gas grill, a large outdoor dining table, and a refreshing outdoor shower.brbrAdditional amenities include central air conditioning, off-street parking for up to three cars, and a peaceful setting perfect for summer getaways.brbrWe hope you enjoy our home and all that Martha’s Vineyard has to offer.

Perfect Vineyard escape steps away from Lagoon Pond and Oak Bluffs

Oak Bluffs, Massachusetts, United States

Bed

Bath

Sleeps

$1079.58

Walking distance to the beach.br5 minutes away from downtown, steamship, ice cream, and restaurants.brLovely backyard with grill to have barbecue parties.brBig driveway that can park 6 cars.brQuiet neighborhood.

Walking to the beach. Bars and Restaurants.

Oak Bluffs, Massachusetts, United States

3

Bed

Bath

6

Sleeps

$2456.44

This quintessential Vineyard cottage was built in the 1920's, and retains most of its original charm and character. Located in the desirable East Chop neighborhood, this little cottage is known for its appearance in the Jaws movie, and affectionately referred to as Little Jaws. Extensive renovations have been completed! This charming home features 3-bedrooms, 2-baths, a sun filled living room with vaulted ceilings and a stone fireplace, a new galley kitchen, and oversized glass doors to take advantage of the dramatic waterviews. Enjoy sunsets and dinners on the large beachfront covered porch. Ride bikes down East Chop Drive to the bustling harbor area or to the action of Circuit Avenue, or launch a kayak from your backyard. This cottage has everything you need for a perfect Vineyard vacation.

Cottage

Fabulous Waterfront 3-Bedroom Martha's Vineyard Cottage

Oak Bluffs, Massachusetts, United States

Bed

Bath

Sleeps

$1677.1

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.' brbrThe house is located on a quiet street, has a large front porch, private back yard and 2 large decks for casual dining and relaxing. brClose to everything - town (5 minute drive/15 min walk) , harbor, ferry, shops, and restaurants. brbrSleeps maximum of 10 people. Rentals are on a weekly basis, Sunday to Sunday.

Beautiful 5 BR, 4.5 baths w/ modern conveniences

Oak Bluffs, Massachusetts, United States

Bed

Bath

Sleeps

$733.6

Bright air conditioned house has common space living TV room, dining and kitchen together. 1st floor has 1 bedroom with 1 single bed w trundle and a bathroom with a bidet, 2nd floor has a queen bedroom with a full bathroom attached. King bed is in large atrium bedroom with a full shower bathroom and bidet, plus a staircase- it shares air space with a spacious loft room with 2 twin beds and 2 trundle beds.brFantastic for a couple or 2 couples, family or a small group. There is 1 King, 1 Queen, the rest are 4 Single beds ! Very clean, modern house with lots of windows - ceiling fans in each room. Two 2nd floor balconies, grassy backyard for playing outside and 1st fl outdoor eating deck /grill. Parking for 3 cars.

Bright Modern House AC 3full baths, 3+ bedrooms, 2 balconies, deck & parking

Oak Bluffs, Massachusetts, United States

Bed

Bath

Sleeps

$1703.14

Fantastic home available from May to October. Seven Bedrooms, one den with pull out couch, two bathrooms and a dreamy outdoor shower. Walk or bike to town for dinner, drinks, ice cream and music. Walk to Jetty Beach (8 minute walk), Circuit Ave (15 min walk) or Inkwell (20 minute walk). Great kitchen with new appliances, breakfast table, couch and wonderful wood burning stove for shoulder seasons. Private, grassy yard and opposite the old Baptist Temple (now gone) Park, full of trees and paths. Classic East Chop home with the quiet of the neighborhood right next to the fun of all the town of Oak Bluffs has to offer. Busses run the island with a stop five minutes away next to Our Market (Groceries and Liquor) on the edge of the harbor. Perfect for a family reunion or cozy get away!br(New Listing on this site, but guest reviews can be found on AIR.)brPS. Several pictures of Oak Bluffs included in photos… VRBO labeled incorrectly as “Golf”, or “View from House” incorrectly. They are the just around the corner local restaurants and nearby Oak Bluffs Ocean park.

Martha’s Vineyard 7 Bedroom Vintage Home! 15 min walk to beaches and Oak Bluffs!

Oak Bluffs, Massachusetts, United States

Bed

Bath

Sleeps

$370.01

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.

Historic Oak Bluffs home, short walk to town, beach, and harbor.

Oak Bluffs, Massachusetts, United States

3

Bed

6

Sleeps

Exceptional(1)

$3591.16

Get ready to relax in this 9-bedroom house in Oak Bluffs. This superb property boasts 3 king beds, 5 full beds, and 2 twin beds, perfect for large groups or families. With 5 bathrooms equipped with showers, guests will have plenty of space to freshen up. Additionally, there is an office space with a full bed for those who need to catch up on work. Experience what Oak Bluffs has to offer with a stay at our house. All this right across from the beach.

Spacious 9-bedroom house with Waterview, WiFi, AC in delightful Oak Bluffs

Oak Bluffs, Massachusetts, United States

Bed

Bath

Sleeps

$865.68

Suzy's Place is arguably the best location on the island. Your cozy getaway awaits in Oak Bluffs at this beautiful newly constructed house in 2024. Sleeps 5 to 6 with 1 king bed and 1 twin sized futon in the bedroom. a queen sofa pullout in the living room and a full size futon in the newly finished basement. This location is perfect for a tranquil retreat, with easy walking access to downtown. Nestled in the Heart of Oak Bluffs, directly behind the historic and charming Gingerbread Cottages. We are also directly across from The Barn and Bistro Restaurant for great food, entertainment and bowling. Enjoy the convenience of amenities like an iron, hair dryer, heating, WiFi, washing machine, and central AC. The bathroom features a new vanity with touch screen mirror, shower and heated tile floors. We also have a huge outside shower, a grille and small outside dining area. Make your holiday one for the books with a stay at our place. We guarantee you will want to stay with us again.

Welcome to Suzy's Place Best Location! Walk Everywhere. Newly built in 2024.

Oak Bluffs, Massachusetts, United States

Bed

Bath

5

Sleeps

$606.81

Summary:brbrPilgrim CottagebrbrbrbrThe Space:brbrWelcome to Pilgrim Cottage, your cozy home base for an authentic Martha’s Vineyard getaway. Set in the very heart of Oak Bluffs, this weathered yet welcoming cottage has been part of the island’s story since 1897, first as a humble “camp” and gradually expanded through the 1940s and 50s. Today, Pilgrim Cottage remains true to its roots: relaxed, comfortable, and filled with character, perfect for guests who appreciate the charm of an unpretentious, truly lived-in home. The cottage is centrally located, making it easy to stroll to sun-soaked beaches, the vibrant Campground with its famous gingerbread houses, and the shops and restaurants along downtown Circuit Avenue. Inside, you’ll find shelves filled with books and puzzles, classic board games for all ages, and an effortlessly comfortable living area—ideal for quiet evenings or rainy afternoons. The kitchen is well equipped for meals together, and out back you’ll discover a raised herb garden with fresh herbs for guests to pick and enjoy. The backyard patio offers a quiet spot for morning coffee or outdoor dining, surrounded by the serene enclosed yard, which is especially inviting for little ones or furry friends since Pilgrim Cottage is dog-friendly. Generations of honeymooners and families have found joy here, drawn by the unassuming comfort and timeless spirit of summer. With thoughtful touches like mini-split air conditioning and WiFi, you’ll have the essentials for a carefree island stay while still enjoying the cottage’s historic soul. Come experience the magic of Oak Bluffs from Pilgrim Cottage, and make your own Martha’s Vineyard memories in this beloved island retreat. Book your stay today—we look forward to welcoming you! bThings to Know/b Check-in time: 4:00 p.m. Check-out time: 10:00 a.m. All guests shall abide by Vacasa’s good neighbor policy and shall not engage in illegal activity. Quiet hours are from 10:00 p.m. to 8:00 a.m. No smoking is permitted anywhere on the premises.

Historic cottage with patio, games, walk to beach & dog-friendly fenced yard

Oak Bluffs, Massachusetts, United States

3

Bed

Bath

5

Sleeps

$623.2

Summary:brbrTumbleINNbrbrbrbrThe Space:brbrWelcome to your ideal island retreat in Oak Bluffs, where unforgettable family vacations and getaways come to life. This charming house is just steps from the vibrant village center, placing you within easy walking distance of sandy beaches, the historic Flying Horses Carousel, and a variety of boutiques, restaurants, and local attractions. Step outside to enjoy the yard, complete with comfortable seating and an outdoor shower, perfect for laid-back summer evenings. Inside, the cozy living room invites you to unwind with a movie night, while the kitchen includes a drip coffee maker, toaster, and all the essentials you need to prepare meals with ease. The home features a restful queen bedroom and a two twin bedroom, comfortably accommodating small families or extra guests. Additional amenities include a hair dryer, an ironing board, and convenient access to an EV charging station just steps away at the nearby town library, making it easy to power up while you explore. Whether you're spending the day beachcombing, browsing local shops, or heading out for a whale watching or fishing tour, this Oak Bluffs gem is the perfect base for your island adventures. Book your stay today and experience the best of Martha’s Vineyard! bThings to Know/b Check-in time: 4:00 p.m. Check-out time: 10:00 a.m. All guests shall abide by our good neighbor policy and shall not engage in illegal activity. Quiet hours are from 10:00 p.m. to 8:00 a.m. No smoking is permitted anywhere on the premises.

Cozy island cottage near local attractions with breezy yard & inviting interior

Oak Bluffs, Massachusetts, United States

Bed

Bath

4

Sleeps

$1595.53

Summary:brbrFamily GetawaybrbrbrbrThe Space:brbrWelcome to your perfect getaway in Oak Bluffs, MA! This charming house offers a delightful blend of comfort and convenience, making it an ideal retreat for families looking to enjoy the beauty of Martha's Vineyard. With a spacious layout that includes multiple levels, you'll find plenty of room to relax and unwind. Step outside to discover a lovely deck, large yard and patio area, complete with outdoor dining furniture and a gas grill, perfect for summer barbecues. For those who enjoy staying active, a tennis court is just steps away, providing a fun way to spend your afternoons. Inside, the home is equipped with modern amenities, including central AC, a gas fireplace for cozy evenings, and a fully stocked kitchen featuring a fridge, gas range, wall oven, and dishwasher. After a day of exploring the island, retreat to the luxurious jetted tub. With comfortable sleeping arrangements, including a king, two queen, and two twin beds, everyone will have a restful night's sleep. Additional conveniences such as a washer/dryer, towels, linens, and beach gear ensure you have everything you need for a stress-free vacation. Whether you're here to relax on the beach, explore local attractions, or simply enjoy quality time with loved ones, this Oak Bluffs home is the perfect base for your island adventures. Book your stay today and create unforgettable memories! bThings to Know/b Check-in time: 4:00 p.m. Check-out time: 10:00 a.m. All guests shall abide by our good neighbor policy and shall not engage in illegal activity. Quiet hours are from 10:00 p.m. to 8:00 a.m. No smoking is permitted anywhere on the premises.

Private house with jetted tub, deck, grill, central AC and large yard

Oak Bluffs, Massachusetts, United States

4

Bed

5

Bath

8

Sleeps

$576.37

Summary:brbrFresh Pond ChateaubrbrbrbrThe Space:brbrWelcome to Fresh Pond Chateau, a beautifully renovated cottage nestled on a serene private road in Oak Bluffs, MA. This bright and cheerful single-level home is the perfect island escape for both relaxation and exploration, comfortably accommodating up to six guests with two cozy bedrooms, a stylish den featuring a queen pullout sofa, and two spa-inspired bathrooms. From the moment you arrive, you’ll feel at ease in this inviting retreat. The open-concept living space is bathed in natural light, creating a warm and welcoming atmosphere for gathering with loved ones or enjoying a movie night on the Smart TV. The fully equipped kitchen boasts stainless steel appliances and all the essentials needed to whip up your favorite island meals. Whether you’re savoring breakfast by the window or grilling dinner on the deck, Fresh Pond Chateau is designed for easy, laid-back living. Step outside to discover a spacious wraparound deck and private patio, complete with outdoor furniture ideal for sipping morning coffee or sharing meals under the stars. After a day of beach adventures, unwind around the fire pit, enjoy a board game with the family, or simply soak in the soothing sounds of nature. Perfectly located just minutes from sandy beaches, charming boutiques, delicious restaurants, and beloved island landmarks like the historic Flying Horses Carousel, this cottage serves as an excellent home base for your Martha’s Vineyard adventure. With high-speed Wi-Fi, a washer and dryer, private parking, and all the cozy comforts you need, Fresh Pond Chateau is ready to host your unforgettable getaway. Whether you're here for sun-soaked beach days or quiet mornings on the deck, this charming home invites you to experience the magic of Martha’s Vineyard at your own perfect pace! bThings to Know/b Check-in time: 4:00 p.m. Check-out time: 10:00 a.m. All guests shall abide by our good neighbor policy and shall not engage in illegal activity. Quiet hours are from 10:00 p.m. to 8:00 a.m. No smoking is permitted anywhere on the premises.

Stylish island retreat with sunny interiors, wraparound deck, firepit & AC

Oak Bluffs, Massachusetts, United States

Bed