Home Vacation Home Rentals By Owner In Oak Bluffs, MA

Showing 80 Of 248 Vacation Rentals
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Exceptional(1)

$772.67

/ Nightly
Private Vacation Home

Charming 3-Bedroom Home in the Heart of Oak Bluffs

Oak Bluffs, Massachusetts, United States

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.
Bed 3

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Bath 2

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Sleep 6

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Exceptional(7)

$1549.84

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Private Vacation Home

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

Oak Bluffs, Massachusetts, United States

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
Bed 4

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Bath 2

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Sleep 9

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$933.21

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Private Vacation Home

Perfect Vineyard escape steps away from Lagoon Pond and Oak Bluffs

Oak Bluffs, Massachusetts, United States

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.
Bed 3

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Bath 2

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Sleep 8

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$623.2

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Private Vacation Home

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

Oak Bluffs, Massachusetts, United States

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.
Bed 2

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Bath 1

Bath

Sleep 4

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$1595.53

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Private Vacation Home

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

Oak Bluffs, Massachusetts, United States

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.
Bed 4

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Bath 5

Bath

Sleep 8

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$606.81

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Private Vacation Home

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

Oak Bluffs, Massachusetts, United States

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.
Bed 3

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Bath 2

Bath

Sleep 5

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Exceptional(3)

$1324.88

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Private Vacation Home

Enchanting home with tennis, firepit, golf nearby & washer/dryer

Oak Bluffs, Massachusetts, United States

Summary:brbrBird's ParadisebrbrbrbrThe Space:brbrFind serenity on the coastal bay of Martha's Vineyard with this fantastic getaway rental. You'll love this conveniently located and cozy home, close by timeless attractions like Martha's Vineyard Performing Arts Center, Flying Horses Carousel, Reliable Market, and Inkwell Beach, all within a three-mile radius. Bring your clubs and enjoy playing on the Obama's favorite Vineyard green, Farm Neck Golf Club, less than a mile down the road. Upon entry, you'll be met with a stylish interior simply flooded with natural light and a cozy atmosphere throughout the well-appointed living space. Relax and make yourself at home by resting on the plush furniture, streaming your favorite movies on the large TV, or challenging your loved ones to a friendly game of air hockey. Curl up with a good book while the chef of the group creates culinary charms in the sophisticated kitchen, equipped with stainless steel appliances, a floating island breakfast bar, and a formal dining table. Comfortable beds in spacious bedrooms ensure that everyone will receive a restful night's sleep from the day's adventures. A majestic main bedroom offers a TV for private viewing, a 180-degree view, and a luxurious en suite bathroom with an oversized walk-in shower. Host a wonderful barbecue outside on the patio with comfortable furniture. Make memories that'll last a lifetime when you visit gorgeous Martha's Vineyard! bTHINGS TO KNOW/b The fireplace is not for guest use. Smoking is not allowed at this property. To use streaming services, guests must log in with their own credentials.
Bed 4

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Bath 5

Bath

Sleep 7

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$576.37

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Private Vacation Home

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

Oak Bluffs, Massachusetts, United States

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.
Bed 2

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Bath 2

Bath

Sleep 6

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Exceptional(6)

$755.2

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Private Vacation Home

Spacious colonial home close to town with AC, porches, & W/D

Oak Bluffs, Massachusetts, United States

Summary:brbrSeabreeze RetreatbrbrbrbrThe Space:brbrWelcome to your perfect summer retreat in Oak Bluffs, MA! This charming house features four spacious bedrooms and two full baths, making it an ideal getaway for families or groups looking to enjoy the beauty of Martha's Vineyard. With central air conditioning on the first floor and window units in each bedroom, you’ll stay cool and comfortable during those warm summer days. The outdoor shower is perfect for rinsing off after a day at the beach, and the open front porch and screened-in back porch provide lovely spaces to relax and enjoy the fresh air. Conveniently located, this home is just a short walk to the vibrant town of Oak Bluffs, where you can explore local shops, dine at delicious restaurants, and soak up the sun at the nearby beach. The ferry transportation to Woods Hole is also within walking distance, making it easy to venture out and explore the surrounding areas. This dog-friendly property offers a parking pad for two cars, ensuring you have everything you need for a hassle-free stay. Inside, you’ll find a well-equipped kitchen with modern appliances, a cozy living room with a TV and DVD player, and a laundry room with a washer and dryer for your convenience. Whether you’re looking to enjoy a day of beachcombing, whale watching, or simply relaxing with a good book, this Oak Bluffs summer house is the perfect home base for your adventures. Book your stay today and create unforgettable memories in this beautiful coastal destination! 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.
Bed 4

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Bath 2

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Sleep 8

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$936.24

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Private Vacation Home

Charming home with walkable beach, large yard, deck, fire pit, and A/C

Oak Bluffs, Massachusetts, United States

Summary:brbrBeach HousebrbrbrbrThe Space:brbrNestled in a tranquil neighborhood of Oak Bluffs, this charming and spacious home offers the perfect retreat for families and friends looking to explore the scenic beauty and seaside charm of Martha’s Vineyard. Just a short stroll away, you’ll find the picturesque Oak Bluffs Harbor and the inviting sands of Inkwell Beach, as well as a delightful mix of restaurants and shops that give the town its unique character. For a one-of-a-kind experience, don't miss a ride on the Flying Horses—the oldest operating carousel in the United States. With the ferry terminal just a short walk from the house, travelers will enjoy easy access to convenient service to Falmouth or Hyannis. The property features a generous outdoor space designed for relaxation and togetherness. The large yard is perfect for family games or lounging in the sun, while the patio and deck offer great spots for enjoying morning coffee, afternoon barbecues, or evening wine. Gather around the outdoor dining area or cozy up at the gas fire pit under the stars for unforgettable island nights. Inside, the home is equipped with everything you need for a comfortable and convenient stay. Amenities include air conditioning, Wi-Fi, and a kitchen with modern appliances such as a refrigerator, stove, and dishwasher. The spacious living room is perfect for enjoying a movie, playing board games, or just relaxing after a day of exploration. A dedicated dining area brings everyone together for shared meals and conversation. Featuring four queen beds along with four twin beds, the home easily accommodates families and groups. Plus, it’s dog-friendly, so your four-legged family members are welcome too! Whether your plans include beachcombing, whale watching, sightseeing, or simply unwinding in your own private oasis, this Oak Bluffs getaway is the ideal base for your Martha’s Vineyard vacation. Book your stay today and start making lasting memories in this beautiful coastal retreat. 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.
Bed 5

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Bath 2

Bath

Sleep 12

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