Vacation Rentals By Owner In Oak Bluffs, MA

$610.1

Charming studio with amazing location near town & beach

Oak Bluffs, Massachusetts, United States

Summary:brbrSankofa StudiobrbrbrbrThe Space:brbrNestled in the historic Vineyard Highlands at the beginning of the African American Heritage Trail, this charming studio in Oak Bluffs, MA, offers a unique and comfortable setting for your vacation. The newly renovated studio is located in the sought-after East Chop area, providing a perfect blend of tranquility and convenience. Just a short walk away from Circuit Ave, Oak Bluffs Harbor, the beach, and the iconic East Chop Lighthouse, you'll have easy access to all the town's attractions while still enjoying a peaceful setting. Parking for one is included directly in front. Explore the area's natural beauty and attractions, from the nearby beaches to the historic sites and lively town center. Whether you're interested in water activities like kayaking or prefer cycling adventures, Oak Bluffs offers something for everyone. After a day of exploration, unwind in the comfortable living space with queen bed and stream your favorite shows. Don't miss the chance to experience the best of Oak Bluffs from this exceptional vacation rental. Book your stay today and create lasting memories in this picturesque seaside town on Martha's Vineyard. Please note that Martha's Vineyard, while beautiful with an abundance of natural landscapes, does have ticks in grassy and wooded areas, so we recommend checking yourself after outdoor activities and taking appropriate precautions to ensure your stay remains enjoyable. 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. Maximum occupancy for this unit is 2. Please park on the gravel directly in front of the studio, not in the driveway. Home has a mini split that offers AC and Heat.

1

Bath

2

Sleeps

Exceptional(6)

$607.16

/ Nightly

Private Vacation Home

Charming Martha's Vineyard retreat close to beaches & downtown - large yard

Oak Bluffs, Massachusetts, United States

Summary:brbrSet SailbrbrbrbrThe Space:brbrSet, sail, and settle down at this charming Martha's Vineyard hideaway! Showcasing one of the island's most renowned locations, this beautiful home sits within the beloved town of Oaks Bluffs. You'll be within close distance of Circuit Avenue, Inkwell Beach, the Oaks Bluff Ferry Terminal, and the Flying Horses Carousel, the oldest platform carousel in the country and a national historic landmark. Venturing out, enjoy exploring the Aquinnah Cliffs, swimming in the warm waters of Nantucket Sound, and discovering Joseph Sylvia State Beach ideal for its windsurfing, beachcombing, and fishing. Other attractions include downtown Edgartown and the Gayhead Lighthouse. Numerous dining and shopping options will also be available at your fingertips. Back at your stay, peace abounds in the gleaming, full, open kitchen, comfortable living room with vaulted ceilings, and outside in the expansive backyard. Precious moments of family time will come with ease as you prepare barbecued meals and dine al fresco in the yard. Afternoons in can be spent over the Ping-Pong table or in the living room, gathered around the coffee table, playing a board game. The home's private washer/dryer ensures your vacation wear is always clean, and partial air-conditioning keeps you cool no matter the temperature outside. Rest easy each evening as you tuck under the soft linens adorning the bedrooms. The perfect vacation awaits, all there's left to do is book! bHouse Rules/b Check-in time: 4:00 PM Check-out time: 10:00 AM All guests shall abide byour good neighbor policy and shall not engage in illegal activity. Quiet hours are from 10:00 PM to 8:00 AM No smoking is permitted anywhere on the premises.

3

Bed

2

Bath

8

Sleeps

$441.77

/ Nightly

Private Vacation Home

Tranquil Home with Private Deck - Walk to Beaches and Downtown Oak Bluffs

Oak Bluffs, Massachusetts, United States

Summary:brbrIsland GetawaybrbrbrbrThe Space:brbrFind plenty of summer sunshine at this two-bedroom Oak Bluffs escape, a comfortable Martha's Vineyard getaway with a private deck, easy access to nearby beaches, and an ideal location within walking distance of downtown. This single-level home sits on a tranquil, dead-end street, just over a mile west of the Steamship Authority Oak Bluffs Terminal, the Flying Horses Carousel, and the lovely beaches in downtown Oak Bluffs. Take morning walks to lounge on the sand at Eastville Beach half a mile west, ride your bike each afternoon to Joseph Sylvia State Beach four miles south, and catch gorgeous sunsets at the East Chop Lighthouse one mile north. This spacious rambler boasts a bit of mid-century style, from the wood-paneled walls to the mod-inspired furnishings in the den. Leave your flip-flops by the door as you cool off from the summer sun in the partial air conditioning, fix yourself a cold Arnold Palmer in the full kitchen, and set out a few homemade appetizers in the dining room, the den, or the main living room. Light the gas grill for dinner and spend the evening hours outside on the deck, sipping cocktails, catching up with loved ones, and watching the stars fill the night sky. Back inside, you can use the free WiFi to plan a few excursions for the next morning, relax to the soothing sounds of the CD player, and pile on the sofa in front of the flatscreen cable TV and DVD player. Find all the comforts of home at this wonderful Oak Bluffs property - book your escape to Martha's Vineyard today!

2

Bath

4

Sleeps

Exceptional(10)

$1336.59

/ Nightly

Private Vacation Home

Historical house with wraparound porch, modern updates, enclosed yard, & W/D

Oak Bluffs, Massachusetts, United States

Summary:brbrVictorian by the SeabrbrbrbrThe Space:brbrA unique coastal stay awaits you and yours at this newly renovated, grand Victorian cottage boasting a prime location, hardwood flooring throughout, and even peek-a-boo ocean views. Enjoy the ocean air from the enclosed yard, which is equipped with plush outdoor seating. When it comes time to explore Oak Bluffs and beyond, head for Ocean Park, both only a short stroll away. With Circuit Avenue, shopping, dining, and the beach only a stone's throw from your door, you'll have countless activities available at your fingertips. Similarly, visit Inkwell Beach, Lighthouse Beach, and Island Alpaca Company. Situated just a few blocks from the iconic Flying Horses Carousel, easily immerse yourself in the nostalgic charm of this historic attraction. For those seeking outdoor adventures, Joseph Sylvia State Beach, known for its ideal conditions for windsurfing, is just a short distance away. When you and your group aren't enjoying the ambience of the wraparound porch, head inside where you'll quickly discover an abundance of historic charm mixed with modern convenience. The light-filled living room boasts plush leather seating, a large smart TV, and gorgeous front windows. Follow the gingerbread detailing into the updated kitchen, which features new appliances. The dining room, front parlor, den, sunroom, and bar space are all also available on the first floor. After days spent under the sun and in the sand, enjoy rinsing under a warm stream of water in the walk-in shower or opt for a soak in the soaking tub. The interior perks include the laundry room, partial air-conditioning, and internet access. bThings to Know/b Check-in time: 4:00 PM. Check-out time: 10:00 AM. Streaming services are available with guests' own accounts. All guests shall abide by our good neighbor policy and shall not engage in illegal activity. Quiet hours are from 10:00 PM to 8:00 AM. No smoking is permitted anywhere on the premises.

Bed

Bath

Sleeps

$1094.26

/ Nightly

Private Vacation Home

Charming home with private hot tub, firepit, deck, grill, outdoor shower, AC

Oak Bluffs, Massachusetts, United States

Summary:brbrTiffany's TreasurebrbrbrbrThe Space:brbrThis two-story home will be just the perfect place to bring the whole family for an unforgettable vacation to Oak Bluffs! Nestled in the woods on a beautiful 1.58-acre lot and adjacent to the Trailhead Southern trails, this private home away from home is the perfect retreat if you are searching for endless peace of mind. You will be close to great local attractions, including Martha’s Vineyard Performing Arts Center, Oak Bluffs Town Beach/Inkwell Beach, Oak Bluffs downtown/ferry, Flying Horses Carousel, Joseph Sylvia State Beach, downtown Edgartown, and Lighthouse Beach. This charming home is all about outdoor living with an extensive deck offering the perfect spot to unwind and create everlasting memories! Treat yourself to soothing baths in the private hot tub or gather around the firepit for some storytelling while roasting marshmallows. Grab your favorite book and head over to the hammock in the woods for a relaxing time. There is an outdoor dining area and a gas grill should you feel like surprising your friends with delicious grilled treats. In addition, you will find an outdoor shower that is perfect for rinsing off! Inside, discover a bright great room with vaulted ceilings and skylights. There is a plethora of entertaining books if you are more of a bookworm. The large kitchen area is appointed with all modern appliances and essentials needed to prepare culinary masterpieces. This floor also houses two bedrooms with access to the deck. Upstairs are two main suites with en suite bathrooms, and one of them also enjoys a private balcony. 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

Bath

Sleeps

$1605.76

/ Nightly

Private Vacation Home

Spacious home in central location with beautiful patio, pool table, W/D, & AC

Oak Bluffs, Massachusetts, United States

Summary:brbrBird Street BreezebrbrbrbrThe Space:brbrNestled in a quiet neighborhood next door to the public library (with access to EV chargers), this bright and airy house in Oak Bluffs, MA, offers the perfect retreat for your vacation. Conveniently located within walking distance to shops, restaurants, galleries, the harbor, and beaches, this house is a hidden gem. With four spacious bedrooms, including two with private decks, you can enjoy your morning coffee or evening nightcap while taking in the serene surroundings. Enjoy the private pool table in the lower level game room complete with comfortable seating and beautiful TV. The open concept kitchen, dining, and living room area is ideal for entertaining, with seating for eight. The kitchen boasts stainless steel appliances, quartz countertops, and a large island, equipped with everything you need to whip up a gourmet meal. From a Kitchen Aid mixer to a Vitamix blender, this kitchen has it all. For outdoor dining, there's a spacious yard with a dining area for ten, a patio for relaxation, and a Weber grill for your BBQ needs. Don't miss the outdoor cedar shower, a true highlight of this property. Each of the four bedrooms are thoughtfully designed and furnished for maximum comfort. From the cozy Grey Room with a small private deck and bistro set, to the spacious Master Bedroom that features a king size bed, private bathroom, reading nook, walk-in closet, and a queen-size pull out 'cabinet' bed, every detail has been considered. With mini split AC, a washer/dryer, and a range of amenities from a high chair to towels, this house has everything you need for a relaxing stay. Please note that this property is strictly an animal-free zone. Entertainment options abound both indoors and outdoors. High-speed internet, flat-screen TVs in every bedroom, Apple TV, and an Echo Dot smart speaker ensure you stay connected and entertained. Outdoor games like volleyball, badminton, and cornhole, as well as beach essentials like chairs and boogie boards, are provided for your enjoyment. Indoors, you'll find a variety of games for all ages, ensuring there's never a dull moment. Explore the charming town of Oak Bluffs, enjoy the nearby beaches, or simply unwind in the comfort of this lovely house. Whether you're seeking adventure or relaxation, this vacation rental is the perfect choice for your next getaway. Book now and start counting down the days to your dream vacation on 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. Please note that this property is strictly an animal-free zone due to the owner's severe allergies.

Bed

Bath

Sleeps

$814.98

/ Nightly

Private Vacation Home

Updated house close to town and beach with patio, AC, and games

Oak Bluffs, Massachusetts, United States

Summary:brbrSankofa HousebrbrbrbrThe Space:brbrNestled in the historic Vineyard Highlands at the beginning of the African American Heritage Trail, this charming home in Oak Bluffs, MA, offers a unique and inviting retreat for your vacation. The newly renovated cottage-style house is located in the sought-after East Chop area, providing a perfect blend of tranquility and convenience. Step onto the fabulous front porch for some people-watching or enjoy a private backyard oasis, ideal for al fresco dining. With 4 bedrooms, 2 baths, and the ability to comfortably sleep 7 guests, this home is perfect for families or groups of friends looking to explore the beauty of Oak Bluffs. Just a short walk away from Circuit Ave, Oak Bluffs Harbor, the beach, and the iconic East Chop Lighthouse, you'll have easy access to all the town's attractions while still enjoying a peaceful setting. Parking is included for two cars in the driveway. The amenities at this vacation home are designed to enhance your stay and provide all the comforts of home. From a washer/dryer and gas fireplace to a fully equipped kitchen with modern appliances, you'll have everything you need for a relaxing getaway. Enjoy the outdoor firepit, patio, and gas grill for memorable evenings under the stars. Explore the area's natural beauty and attractions, from the nearby beaches to the historic sites and lively town center. Whether you're interested in water activities like kayaking and jet skiing or prefer hiking and cycling adventures, Oak Bluffs offers something for everyone. After a day of exploration, unwind in the comfortable living spaces, play board games, or stream your favorite shows. Don't miss the chance to experience the best of Oak Bluffs from this exceptional vacation rental. Book your stay today and create lasting memories in this picturesque seaside town on Martha's Vineyard. Please note that Martha's Vineyard, while beautiful with an abundance of natural landscapes, does have ticks in grassy and wooded areas, so we recommend checking yourself after outdoor activities and taking appropriate precautions to ensure your stay remains enjoyable. 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.

4

Bed

2

Bath

7

Sleeps

$375.96

/ Nightly

Private Vacation Home

Cozy getaway in a central location w/ a full kitchen & furnished deck

Oak Bluffs, Massachusetts, United States

Summary:brbrSea Glen CottagebrbrbrbrThe Space:brbrThis lovely cottage awaits you for your next Martha's Vineyard getaway with the whole family! Featuring a spacious living area, a well-appointed kitchen, and a furnished deck with a convenient outdoor dining area, this home is sure to delight guests of all ages. What's nearby: Just seven miles off the shores of Cape Cod, Martha's Vineyard is famous for its beautiful beaches, myriad lighthouses, and chic eateries. This home offers a central location to everything the island has to offer putting you just minutes away from shops, restaurants, beaches, libraries, hiking trails, and more. And if you're planning on preparing home cooked meals during your stay, you will be right across the street from the fresh vegetables of Norton’s Farm. Things to know: Free WiFi Full kitchen with a dishwasher The basement is a separate unit for the owner and they may be present during your stay

Bed

Bath

Sleeps

$862.63

/ Nightly

Private Vacation Home

Elegant Dream Home w/ Luxurious Living Spaces, Full Kitchen, & Wraparound Porch

Oak Bluffs, Massachusetts, United States

Summary:brbrOak ManorbrbrbrbrThe Space:brbrWelcome to your dream getaway in the charming town of Oak Bluffs, MA! This delightful two-story Victorian home is perfectly situated just a stone's throw away from the beach, restaurants, and shopping, making it an ideal retreat for families and friends alike. With a bit of a water view from the front porch, you can enjoy the ocean breeze by while sipping your morning coffee or unwinding in the evening. The location is unbeatable...a car is not necessary! Just one block from the park and only three blocks from the vibrant center of town, you'll find everything you need within easy walking distance including the ferry, downtown, bus to check out the island and beach. The historic Flying Horses Carousel, arcades, bowling alleys, and ice cream parlors are all nearby, ensuring that kids will have endless fun. Plus, Inkwell Beach and Oak Bluffs Town Beach are less than a five-minute walk away, perfect for sun-soaked days by the water. Inside, the home combines throwback charm with modern amenities. Enjoy the comfort of central AC, a fully equipped kitchen with a fridge, stove, and dishwasher, and a cozy living room with cable TV. The outdoor space features a deck, outdoor shower and patio with furniture and a gas grill, ideal for summer barbecues and al fresco dining. With a washer/dryer and all the essentials provided, you can relax and enjoy your vacation without a worry. Whether you're looking to explore the local nightlife, indulge in delicious seafood, or partake in outdoor adventures like sailing and kayaking, this Oak Bluffs home is the perfect base for your island getaway. Book your stay today and make unforgettable memories in this picturesque coastal paradise! Things to Know

Bed

Bath

Sleeps

$1145.58

/ Nightly

Private Vacation Home

Spacious island home near Farm Neck Golf Course, the beach and town

Oak Bluffs, Massachusetts, United States

Summary:brbrTwin PondsbrbrbrbrThe Space:brbrNestled just a stone's throw away from the renowned Farm Neck golf course in Oak Bluffs, MA, this spacious house offers the perfect retreat for your Martha's Vineyard getaway. Explore the area's natural beauty and attractions, from the nearby beaches to the historic sites and lively town center. Take advantage of the various activities available, from stand-up paddle boarding on the bay to whale watching, fishing, and kayaking. Whether you're interested in water activities like kayaking and jet skiing or prefer hiking and cycling adventures, Oak Bluffs offers something for everyone. The Tower Ridge complex, located across from the Farm Neck golf course, provides a picturesque setting for your vacation. Enjoy the convenience of amenities such as a tennis court, central AC, a wood-burning fireplace, a washer/dryer, and smart tvs in all of the bedrooms, ensuring a comfortable and enjoyable stay. Also, with the totally renovated bathrooms featuring luxurious showers with body sprays, you'll feel pampered and relaxed during your stay. When you step outside onto the deck or patio, complete with patio furniture and a gas grill, you will find the perfect setting for outdoor gatherings and al fresco dining. With easy access to local attractions, restaurants, and shops, you'll have everything you need for a memorable vacation. Whether you're seeking adventure, relaxation, or family fun, this house in Oak Bluffs is the ideal home base for your Martha's Vineyard getaway. Book now and start planning your dream vacation in this beautiful coastal town! Things To Know

4

Bed

3

Bath

10

Sleeps

$519.27

/ Nightly

Private Vacation Home

Cute & cozy cottage with a patio & gas grill in the heart of Martha's Vineyard

Oak Bluffs, Massachusetts, United States

Summary:brbrWinthrop CottagebrbrbrbrThe Space:brbrIf you are planning a family vacation to Martha's Vineyard, consider this affordable and comfortable cottage in Oak Bluffs! With a well-equipped kitchen, furnished patio, and outdoor gas grill, plus two TVs for relaxing after a day in the sun, this property has everything you might need to enjoy a fantastic stay on the Vineyard. Make your vacation a memorable one and book with us today! What's nearby: This cottage is just a short drive from the ocean and downtown Oak Bluffs. East Chop Lighthouse is an easy drive north and a fantastic choice for a day trip. Be sure to take a walk through Oak Bluffs as well as Vineyard Haven to experience the great local restaurants and adorable shops. What's included: Free WiFi Full kitchen with a dishwasher

3

Bed

1

Bath

6

Sleeps

$591.4

/ Nightly

Private Vacation Home

Charming home away from home near lagoon pond w/ boat launch

Oak Bluffs, Massachusetts, United States

Summary:brbrIsland SanctuarybrbrbrbrThe Space:brbrThis inviting and comfortable Oak Bluffs vacation home awaits your stay! With all the comforts of home like A/C, private laundry, an outdoor shower, cable TV, free WiFi, grill, and a spectacular location, you're sure to have a fantastic getaway here. Located on a gorgeous grassy plot walking distance to the lagoon, this Oak Bluffs vacation home is an ideal spot for your Martha's Vineyard holiday. Walk to the scenic shores of Lagoon Pond via Sail Camp Park where you can launch your boat. If you're visiting for a wedding or private party, this home is the perfect location to travel easily between the Sail Camp Park event hall and the home. The famous East Chop Lighthouse is just three miles away for a traditional New England experience. The partially fenced yard has an ornamental cherry tree with the most beautiful blossoms in the spring, and offers the perfect shade from the summer sun. A furnished deck with gas grill is the perfect place to have a family cookout after a day at the beach. There is an outdoor shower to rinse off the sand and salt as well. Enter through the sliding glass doors from the deck to the family dining room with seating for eight at the counter-height dining set. The soft sage-colored walls, hardwood floors, and natural light give a bright and airy feel. After dinner, settle into the living room to watch a DVD you brought or the big game on cable TV. If you've got to make a few last-minute touches to your vacation or event plans, the WiFi will keep you connected. If you get the itch to cook up a filling dinner or a lumberjack breakfast, the kitchen is well-equipped for your needs. A Keurig coffeemaker is available for the coffee lover, and a dishwasher makes cleanup easy. About 10 miles across the island is Norton Point Beach if you want a true summer experience. Take a drive to the other side, about 16 miles, and visit the village of Aquinnah and see the amazing views from the well-known cliffs. Staying for an extended period of time for an event or just on the island for a break from the city This Martha's Vineyard vacation home is ideal for helping you create memories to last a lifetime! bTHINGS TO KNOW/b The yard is partially fenced. A window AC in all rooms. Four beach chairs are available for guest use. Age-appropriate games are available for younger guests.

2

Bath

7

Sleeps

Exceptional(17)

$1448.17

/ Nightly

Private Vacation Home

Newly remodeled home w/ new furniture, large yard & great porches

Oak Bluffs, Massachusetts, United States

Summary:brbrSunny Side UpbrbrbrbrThe Space:brbrFreshly remodeled with brand new furnishings throughout, this Oak Bluffs home is the perfect blend of modern comfort and classic Vineyard charm. Spend your mornings with a newspaper and a cup of coffee on the porch swing, relish in the cool island breezes on the sun deck and the back deck, and enjoy wonderful access to local beaches, the ferry terminal, and downtown Oak Bluffs! What's nearby: This home sits just over a mile west of the Oak Bluffs Steamship Authority Terminal, on large grassy property lined with trees. In downtown Oak Bluffs to the east, you'll find grocery stores, coffee shops that include Mister Pugg's Mugg and Martha's Vineyard Gourmet Cafe & Bakery, and restaurants such as Sea Smoke Barbecue and Chef Deon's Kitchen. You'll also be only a mile west of Inkwell Beach, Oak Bluffs Town Beach, and the historic Flying Horses, and four miles northwest of Joseph Sylvia State Beach. Things to know: Free WiFi Full kitchen Window AC units in every bedroom Wood burning fireplace is for decorative purposes only - not for guest use

3

Bath

8

Sleeps

$1261.97

/ Nightly

Private Vacation Home

New Construction with Patio & Yard - Downtown & Beaches

Oak Bluffs, Massachusetts, United States

Summary:brbrOak Bluffs BeautybrbrbrbrThe Space:brbrImmerse yourself in the charms of Oak Bluffs at this Martha's Vineyard home, a wonderfully walkable escape with a private patio, a tree-lined yard, and outstanding access to beaches, restaurants, and the ferry terminal. Conveniently situated a few blocks west of downtown Oak Bluffs, this newly built home is a quick one-mile walk from the Steamship Authority Terminal. Take your kids for a spin on the Flying Horses Carousel one mile east, or spend your days in the sunshine on Eastville Beach (half a mile west), Oak Bluffs Town Beach (one mile east), and Inkwell Beach (less than two miles east). Simple, casual, and comfortable, the living space is a wonderful respite for a beach-going family or a group of friends. With four bedrooms plus a loft space, there's plenty of room for everyone to spread out. Come home from a day on the sand to throw your bathing suits in the private washer/dryer, luxuriate in the central air conditioning, and use the free WiFi to share photos of the day's adventures. Wake up each morning to grind your own coffee beans and prepare blueberry pancakes in the full kitchen (with stainless steel appliances, including a dishwasher). Step outside to play a game of tag with your kids on the lawn, take a walk into downtown Oak Bluffs to peruse the shops and galleries, and come home to settle in for a movie on the flatscreen cable TV. Experience summer in New England as it was meant to be enjoyed - begin planning your Martha's Vineyard getaway today!

4

Bed

3

Bath

10

Sleeps

$538.65

/ Nightly

Private Vacation Home

Lakefront Cottage with a Deck, Free WiFi, Gas Grill - Close to Ferries & Beaches

Oak Bluffs, Massachusetts, United States

Summary:brbrSunset MeadowsbrbrbrbrThe Space:brbrThe stunning waterways and marshlands of Martha's Vineyard are just outside your door at this two-bedroom Oak Bluffs home, a charming island cottage that offers a lovely back deck, an ideal location close to the ferries, and views of Brush Pond, Lagoon Pond, and Vineyard Sound. Beautifully situated on the eastern edge of Brush Pond, this single-level home enjoys waterfront views that reach all the way to downtown Vineyard Haven. It's also just over one mile from the Oak Bluffs Steamship Authority and Oak Bluffs Town Beach, two miles from the Vineyard Haven Steamship Authority, and only four miles from the gorgeous expanse of Joseph Sylvia State Beach. Whether you're planning a family vacation or a summer getaway with friends, this quaint cottage puts you within walking distance of the ferries, ocean beaches, restaurants, and shops that make Martha's Vineyard so special. You'll find hardwood floors, large windows, and vibrant hues of blue and green in the sunny and cheerful living space. Return home from a day on the beach (sand-free, thanks to the outdoor shower) and challenge your friends to a board game, or use the WiFi to make dinner reservations in downtown Oak Bluffs. The blue-and-green motif continues in the full kitchen, which features butcher block countertops, full-size appliances, and even a dishwasher to handle the clean-up. Use the lobster pot to boil freshly caught seafood, and sit down for dinner at the spacious indoor dining table. The home is equipped with a private washer and dryer. The living room area has an A/C minisplit which will help you feel cool and comfortable in the summer months. But there are few reasons to stay inside when such beautiful views await on the back deck. Spend your days sunbathing on an Adirondack chair or simply admiring the stunning view of Brush Pond, Lagoon Pond, and Vineyard Haven; each evening, fire up the gas grill for a sunset meal at the patio table. Head down to one of the nearby beaches each morning to catch a beautiful sunrise. You'll come home to a TV with basic cable and a DVD player to help you unwind. With two bedrooms and one full bathroom, this home will comfortably sleep as many as four guests. The master bedroom offers a queen-size bed, while the guest room features a twin-size futon. And you need not worry about keeping your beach clothes salt- and sand-free. This home is equipped with a private washer and dryer, as well as baseboard heat for chilly island evenings. As one of New England's most beloved beach destinations since the 19th century, Oak Bluffs is a place for leisurely bike rides and afternoon swims in the warm waters of Nantucket Sound. The calm waves of Oak Bluffs Town Beach are perfect for families, and you'll be just a few blocks from the Flying Horses Carousel, the oldest platform carousel in the country and a national historic landmark. Just a few miles south of Oak Bluffs, the two-mile expanse of Joseph Sylvia State Beach is ideal for windsurfing, beachcombing, and fishing for striped bass. Don't miss this opportunity to enjoy the breathtaking landscapes of Martha's Vineyard - reserve your stay at this Oak Bluffs cottage today!

2

Bed

1

Bath

4

Sleeps

$2305.81

/ Nightly

Cottage

Waterfront Family Escape with Dock & Private Beach in Oak Bluffs

Oak Bluffs, Massachusetts, United States

Escape to this beautiful 5-bedroom waterfront cottage in Oak Bluffs, where coastal charm meets comfort and relaxation. Nestled in a quiet, secluded East Chop Drive yet only minutes from the ferry, this inviting home is the perfect getaway for families and friends looking to unwind and enjoy island life.brEnjoy the rare luxury of a private beach and dock — ideal for swimming, kayaking, paddleboarding, or simply soaking up the sun. Sip your morning coffee on the deck overlooking the water, then take a scenic stroll or bike ride along East Chop Drive. In the evening, unwind as you watch the sunset paint the sky over the harbor.brInside, the cottage features bright, spacious living areas, a fully equipped kitchen, and comfortable bedrooms designed for restful nights after days of Vineyard adventure. With its unbeatable location and warm, welcoming atmosphere, this home offers everything you need to make lasting island memories.

Bed

Bath

Sleeps

$1780.82

/ Nightly

Private Vacation Home

Waterview Farm Contemporary Island Home Walk to Beach and Farm Neck Golf Club

Oak Bluffs, Massachusetts, United States

Six bedroom, five and a half bath contemporary island home located in Waterview Farm with direct access to the beach on Sengekontacket Pond. Sleeps twelve comfortably. Unique layout includes an attached cottage with a separate kitchenette and washer/dryer. Perfect for two families or friends looking for their own separate space. The main house features a spectacular post and beam construction with an open floor plan, soaring ceilings, wood floors, handmade wood dining table seating eight, twin-flue fireplace, modern kitchen with granite countertops, two sinks, two Bosch dishwashers, skylights, washer/dryer, stereo system, and private master bedroom suite. The outdoor splendor is enhanced by four outdoor cedar wood decks, a grill, an enclosed outdoor heated shower, two driveways and lovely curb appeal. A short 5 minute stroll through the gorgeous Waterview meadow leads to a small association beach, with its own dock, a grill, and access to two private kayaks. Kayak across the Sengekontacket Pond to State Beach or the Felix Neck Wildlife sanctuary. For those avid golfers, this home is walking distance to the famous Farm Neck golf course. Pecoy Point Preserve is directly across the road with walking trails and excellent clamming on the Sengekontacket.

6

Bed

4

Bath

12

Sleeps

$1160.21

/ Nightly

Apartment

Spacious Second FL 4-Bedroom Rental – Private Entrance & Newly Renovated Deck!

Oak Bluffs, Massachusetts, United States

Spacious 4-Bedroom Rental in Oak Bluffs – Private Entrance & Newly Renovated Deck!brEnjoy the best of Oak Bluffs in this spacious second-floor rental, perfect for a relaxing getaway. This beautifully designed space features:brFour bedrooms with king beds for ultimate comfortbrFour full bathrooms for convenience and privacybrLiving room area for gathering and unwindingbrKitchenette for easy meal prepbrIn-unit washer & dryerbrSeparate private entrance for added privacybrNewly renovated deck to enjoy the fresh island airbrLocated in Oak Bluffs, just a short distance from Inkwell Beach and local attractions, this rental is ideal for families, couples, or groups looking for a comfortable and well-appointed stay.brOnly one month stays available. Make sure to enter 31 nights or more, or it will show as unavailable on this site.brBook your stay today!brbrhttps://my.matterport.com/show/ m=82Nc5RVa1aUbrCopy and paste this link into your browser to view the virtual tour!

Bed

Bath

Sleeps

$1562.28

/ Nightly

Private Vacation Home

Heart of Oak Bluffs - A Newly Renovated Gem, 5 Minute Walk to Town!

Oak Bluffs, Massachusetts, United States

Discover the perfect blend of location and luxury in this beautifully renovated charmer, centrally situated in Oak Bluffs. Just a 5-minute walk to Circuit Ave and Sea View, this home offers unparalleled convenience and style.brbrStep inside to a bright, open first floor featuring a state-of-the-art entertainment system with a large TV and surround sound. The highlight of this home is the incredible wrap-around enclosed terrace, ideal for relaxing, gaming, and reading.brbrThis gem boasts three stunning bedrooms, two modern bathrooms, and a formal dining area. Enjoy the newly renovated kitchen, central A/C and the outdoor deck, which provides extra space for entertaining.brbrFall in love with this beautifully renovated space and its prime location in the heart of Oak Bluffs.

Bed

Bath

Sleeps

$630.31

/ Nightly

Private Vacation Home

New 2 min from Circuit ave

Oak Bluffs, Massachusetts, United States

* new for 2025: Gameroom with pool table and ping pong table. *brbrWelcome to this beautifully renovated home, located within 2 minutes away (drive) from downtown Oak Bluffs ( Circuit Ave).brbrThere are 5 bedrooms plus open loft area, 2 full bathrooms with rain shower, this home provides ample space to accommodate 12 people max.brbrThere are 2 bedrooms on the first floor - both Queens. The second floor has 2 bedrooms, 1 bedroom has 2 twins and one queen. In the open loft area, there is a sectional coach with sofa bed.brbrThe kitchen is open to the dining and living room area. All the appliances are new and it is fully stocked with all your needs.brbrBackyard with deck, patio, outdoor table, and chairs with a BBQ grill. Plenty of space with new grass to play around with family and friends. brGame room availablebrBoard games available brOutdoor games availablebrBeach towels availablebrCooler available brbrDriveway fits up to 6 cars brbrbrbrbrbrbrbrRelax with the whole family at this peaceful place to stay.

5

Bed

2

Bath

10

Sleeps

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