Vacation Rentals By Owner In Oak Bluffs, MA

Enjoy everything the island has to offer in a spacious, custom-built, fully-stocked modern farmhouse and backyard oasis with a private pool and outdoor kitchen that enable a relaxing and serene retreat. This picturesque home, The Felicity, has brand-new furnishings and is ideally situated on the bike path and walking distance or a short drive to Oak Bluffs village, several beaches, Farmneck Golf and Tennis Club, downtown Vineyard Haven and both ferries. brbrThe Felicity is an immaculate home with designer touches throughout and contains multiple sitting areas for families and friends to gather after a day at the heated pool or beach. The sitting areas include a large great room with a flatscreen TV for movie nights and an open concept and spacious living area. Additionally, the lower level family and game room has a flatscreen TV and a pool/ping-pong/hockey table for rainy days and late nights. And, finally, catch up on email or read a book while lounging in the cozy loft sitting area on the 2nd floor.brbrThis large, 3,000 square foot, 3-level, home has 4 bedrooms and can accommodate 10 guests. Bedroom #1 is on the 2nd floor and has a King-sized bed, ensuite bathroom and private deck. Bedroom #2 is on the 2nd floor, overlooks the backyard, and has a queen-sized bed. Bedroom #3 is also on the 2nd floor and comfortably provides 2 full-sized beds. Bedroom #4 is on the lower level and is perfect for both adults and young children as it contains two twin beds, books, toys, and a mini-couch for reading to little ones. Guests who prefer to not share beds can sleep on one of the two queen-sized sofa beds in the living room or family room. Likewise, a pack ’n play is available for a little one.brbrThe stylish gourmet cook's kitchen is equipped with commercial appliances, granite countertops, a large island/breakfast bar with seating for 3, and all the cookware needed for entertaining or family dinners. The dining room is just off the kitchen and has seating for 10 — not including the high chair for a little one. The lower level includes an overflow kitchen with an extra fridge and sink.brbrNo need to schedule shower-time as the house contains 3 1/2 bathrooms. Bathroom #1 is a conveniently located powder room on the 1st floor. Bathroom #2 is part of the ensuite master bedroom on the 2nd floor and contains dual sinks and a large shower with full-body faucets and a sitting bench. Bathroom #3, on the 2nd floor, has a combo tub/shower. Bathroom #4 is on the lower level and contains a shower.brbrThe Felicity has a professionally landscaped yard on a large, wooded private lot that boasts mature trees, a well groomed lawn, an array of colorful flowers and plenty of space for outdoor games. This outside oasis contains a private, in-ground 24’x16’ pool with a child-safety fence, an outdoor shower, a basketball hoop, a front porch with rocking chairs for quiet contemplation, a deck for outdoor meals, and a bluestone custom kitchen with a gas grille, sink and counter.brbrThe Felicity was meticulously and thoughtfully designed and furnished to include all of the amenities you would want in a vacation home: central AC, Wi-Fi, Digital Cable, washer/dryer, linens, towels, ample parking, and even some family games.brbrNOTE: The pool is open each year from mid-May through the end of October and is heated to 80 degrees fahrenheit.

Modern 4 bed/3.5 bath Farmhouse, private HEATED POOL and AC on bike path

Oak Bluffs, Massachusetts, United States

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Bath

Sleeps

$4039.82

6 Bedrooms, Sleeping Porch, 3 Full Baths, 2 Half Baths, Sleeps 12+brbrA timeless Martha’s Vineyard escape awaits you at this extraordinary Harthaven home! brbrThis idyllic beach home is the ultimate in serenity and tranquility, but is close to the bars, restaurants and shopping in downtown Oak Bluffs and Edgartown. brbrThe house is a prime example of New England shingle-clad coastal architecture. Inside, it's a charming space, with light flooding in through windows overlooking the ocean. Wood floors and a whitewashed color scheme give it a hint of seaside chic, with comfortable furniture and colorful accents and artwork. brbrThere’s a private yard for eating outdoors on warm summer days, and a fire pit to sit around in the cooler evening air. Tie up your boat at the private dock, and use the kayaks and stand-up paddle boards for fun on the water.brbrYou'll be staying across the street from Noman's - just a mile from downtown Oak Bluffs and four miles to downtown Edgartown. Take the bike path one mile to Oak Bluffs, you will find lots to do between the famous Flying Horses, MVCMA gingerbread cottages, Ocean Park, Back Door Donuts, the bowling alley, the Arts District and the game room. In the other direction on the bike path, you will go past the Jaws Bridge, and into Edgartown with its captains house, the Old Whaling Church, art galleries and shopping.brbrBack at the house, the large living room has a stone fireplace, the eat-in kitchen has an island with seating for 6, the dining room seats twelve of your friends and family, and the six bedrooms and a sleeping porch allow for many guests. There are four enclosed porches, two on the first floor, and two on the second floor. A large private yard provides plenty of space for outdoor activities. The house is a member of the Harthaven Association, which allows use of the association's private beach, harbor, and tennis court. Central A/C and heat will keep you comfortable in all types of New England weather.brbrLIVING AREAbrbrGather in the sunlit living area after a day enjoying the island! Two sofas by the wood-burning fireplace and three armchairs by the windows create inviting areas. Two indoor porches have additional seating areas. There is a Smart TV with cable, wifi, and lots of games. brbrKITCHEN and PANTRIESbrbrThe modern kitchen is well appointed with a commercial Wolf stove having 6 burners & a griddle, two ovens, a Bosch dishwasher, a Kitchen Aid refrigerator with ice maker, granite countertops, and windows overlooking the herb gardens. An island has seating for six. brbrThe butler's pantry, between the kitchen and dining room, has a bar sink and a wine refrigerator as well as a soda stream, a microwave, coffee maker and plenty of glassware and china.brbrOutdoors there is a charcoal barbecue. brbrA pantry has a large freezer for your bags of ice and all the fish you catch - as well as a variety of kitchen appliances. br brA washer and dryer takes care of your laundry needs.brbrDININGbrbrA large wooden farmhouse table with benches and dining chairs seats 12 guests. brbrBEDROOMS and BATHROOMSbrbrThis home easily sleeps more than 12 guests between the six bedrooms and two sleeping porches. brbrThe primary bedroom is on the second floor overlooking the ocean, has a king-sized bed and a TV with Roku. The primary bathroom is ensuite with a tub/shower combo.brbrThe Orange Bedroom, also on the second floor, has a king-sized bed and an ensuite half bath.brbrThe Blue Bedroom, on the second floor has a king-sized bed and overlooks the ocean.brbrThe Gold Bedroom, on the second floor has a Queen bed, and overlooks the second floor deck.brbrThe White Bedroom on the second floor has a full-sized bed with a canopy for the princess of the house.brbrOn the first floor, a bedroom with a queen-sized bed can be configured into a private suite with a porch and bathroom with walk-in shower, if desired.brbrThere is a shared bathroom on the second floor with a walk-in shower and a door to the upstairs deck, which has an outdoor shower.brbrOUTDOOR AREA & AMENITIESbrbrEnjoy your morning coffee on the large deck overlooking the Osprey nest and ocean. brbrAfternoon cocktails become evening dinners around the tables seating 16 or more. brbrA large lawn gives space for croquet, bocce and corn hole, all of which are provided.brSit in the sun on lounge chairs, or gather around the fire pit for evening 'smores and sunset. brbrA second outdoor shower on the edge of the trees makes it convenient to rinse off after beach days.brbrEXTRA PERKS & MORE DETAILSbrbrGuest amenities include five stand-up paddle boards, three kayaks, Wi-Fi, beach chairs and towels - all provided in the rental. brbrThe driveway allows parking for many cars. brbrThe house is located on the bike / walking path from Oak Bluffs to Edgartown, which gives easy access to both towns. brbrNomans restaurant is a short stroll away for drinks, lunch, dinner, and lots of lawn games.brbrbr

Oceanfront, Private Dock and Harthaven Private Beach - Walk to Noman's, Inkwell

Oak Bluffs, Massachusetts, United States

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Bath

Sleeps

$523.6

This 4 bedroom, 3-story home has plenty of space to relax with two decks and a private third level master suite. Located in a private neighborhood, our home backs up to common wooded land. Walk or ride your bike on our quiet roads using dedicated bike path is located just outside our neighborhood with biking access to Oak Bluffs, Edgartown or Vineyard Haven. A short walk to 2 private tennis courts (available for your use). Minutes by car to beaches and towns and Farm Neck golf course is only 1 mile away. brbrOn the third floor is a master bedroom suite. The entry brings you into the large sitting room with its own deck, cable TV, and fireplace. The bedroom has a king-size bed, walk-in closet, and a full bath with jacuzzi. brbrOn the first floor there are three large bedrooms (2 with queen beds, one with king (can be twins)), a full bathroom (double sinks) and a laundry room. Perfect for several couples or a family to nestle in with comforts of home and privacy. brbrThe second level has the common space to gather as a family for meals and relaxing, consisting of a living room with fireplace, dining room with a large bay window, and a deck the length of the house, with one half screened. French doors lead from the living room into the den, where you will find many games, movies and books. The kitchen is fully equipped with new appliances, white cabinets and tile floor. There is a coffee maker, toaster, toaster oven and microwave. brbrThe basement was recently finished off, complete with toys and living room area with tv. A perfect space for movie nights and relaxation!brbrThe home is cooled by wall mounted mini-split units in each room, controlled by remote controls. These are very quiet efficient units.brbrFor your baby needs, we have Pack and Plays, high chairs, booster seats for use at the table and plastic bowls, plates, cups, and utensils, and a full sized crib. brbrOak Bluffs is a terrific town with great restaurants, beaches, the famous Flying Horses Carousel. Martha's Vineyard has an island wide public bus system with a bus stop just outside Meadow View Farms. The Steamship Authority ferries, the Island Queen, the Hy-Line boat from Hyannis, and Fast Ferries from Rhode Island and New York have ports in Oak Bluffs, a short 5-10 minute ride away,making it easy to pick up guests. The airport is 10 minutes away as well.brbrWe invite you to relax, explore and feel comfortable at our vacation property in Oak Bluffs.

4 bedroom home family friendly in desirable area

Oak Bluffs, Massachusetts, United States

4

Bed

Bath

10

Sleeps

$1090.32

Welcome to your perfect Vineyard vacation retreat! This fully renovated 3-bedroom, 2-bath home is all about location, comfort, and convenience. Nestled just steps from the vibrant shops, restaurants, and nightlife of Circuit Avenue, and only a short stroll to iconic Inkwell Beach, you’ll be in the heart of everything Oak Bluffs has to offer. The space features a fully stocked modern kitchen, 2 queen beds and 2 fun bunk beds, perfect for families or groups. With 2 bathrooms, mornings are easy and convenient. This terrific home offers a delightful blend of comfort and charm, making it a perfect spot to unwind. Wake up to morning coffee on the porch, spend the day sunbathing or exploring town, and unwind in the beautifully updated space with AC in every room, modern furnishings, and coastal charm throughout. Located directly across from family-friendly Niantic Park—with tennis courts, basketball courts, pickle ball and a new playground with lots of open green space—this home is perfect for families, couples, or friends looking to relax and enjoy the Vineyard lifestyle. Whether you're here for beach days, bike rides and walks by the harbor, this vacation home is your ideal island escape. Linens are NOT included but can be requested for an additional fee.

Newly Renovated Downtown Victorian Charmer, AC, Walk to Beach

Oak Bluffs, Massachusetts, United States

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Bath

Sleeps

$1072.32

Welcome to Noble House, your ideal getaway on Martha’s Vineyard. Nestled in the heart of Oak Bluffs at 21 Pheasant Lane, this Gambrel-style retreat offers a perfect combination of island charm, modern amenities, and thoughtful touches designed to make your stay exceptional. Whether you’re looking for a cozy winter retreat, a vibrant spring escape, or a tranquil fall adventure, Noble House is ready to welcome you.brbrOwned by the husband-and-wife team behind a renowned art studio, this home reflects their passion for creativity, design, and attention to detail. Every space is thoughtfully curated to provide both comfort and inspiration.brbrThe Space:brbrBedrooms & Bathrooms brNoble House features three spacious bedrooms with comfortable bedding, perfect for restful nights, and two full bathrooms stocked with fresh linens and essentials.brbrLiving Areas brThe inviting living room, centered around a cozy fireplace, creates the perfect atmosphere for relaxing after a day of exploring the island. The well-equipped kitchen offers everything you need to prepare home-cooked meals, from modern appliances to ample cookware and tableware.brbrHeated Sunroom brA standout feature of Noble House is the enclosed, climate-controlled sunroom. This versatile space boasts a large dining table for family meals or game nights, a cozy sectional sofa for lounging, and a flat-screen TV for your favorite shows or movie nights, making it a year-round delight.brbrOverflow Sleeping Area & Nautical Bunkhouse brFor extra guests, the home includes an overflow sleeping area with a full-sized bed. Kids or the young at heart will love the whimsical nautical-themed bunkhouse—a cozy, fun space that adds to the home’s unique charm.brbrOutdoor Spaces brStep outside to a private deck where you can enjoy your morning coffee or evening wine. The fenced, level yard provides a secure area for outdoor activities, while the outdoor shower is perfect for rinsing off after a beach day. Nearby, a scenic bike path invites you to explore the island’s natural beauty.brbrWhat Makes Noble House Special:brbrOwned by Artists: brThis home is owned by the husband-and-wife team behind a celebrated art studio, and their artistic vision shines throughout the space with unique design touches and carefully curated details.brbrLocation: brMinutes from vibrant Circuit Avenue, Noble House offers easy access to Oak Bluffs’ best shops, restaurants, and attractions. The ferry and local beaches are also just a short drive away, making it the perfect base for exploring Martha’s Vineyard.brbrCaretaker Services: brFor your convenience, a dedicated caretaker is available to assist with any needs during your stay, ensuring a seamless experience.brbrAmenities: brEnjoy high-speed Wi-Fi, a washer and dryer, and thoughtful touches like an outdoor shower and plenty of comfortable seating areas.brbrHouse Rules: brNo pets brNo smoking brNo parties or events brbrAt Noble House, every detail is designed to make you feel at home. Whether you’re here to relax by the fire, enjoy the island’s off-season beauty, or create memories with family and friends, this home is the perfect place to start. Book your stay today and experience the magic of Martha’s Vineyard.

Charming 3-bedroom house in Oak Bluffs with AC, WiFi

Oak Bluffs, Massachusetts, United States

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Bath

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$543.61

Gorgeous newly renovated and newly furnished mid-century beach cottage designed by prominent interior design firm Tersigni Palachek as a modern vacation oasis in a historic waterfront community with private beach and dock. This eloquent, yet rustic home offers three levels of living spaces, including a spacious loft, two master bedrooms and expansive deck. Tucked in the waterfront community of Waterview Farms, this home has access to association beach and dock on Sengekontacket, a favorite for those who love to kayak, windsurf, para surf and clam. It is only about a half mile from golf and tennis at Farm Neck Golf Club, 2 miles to Oak Bluffs center, and 3 miles to popular State Beach. The central location provides easy access to multiple public beaches and the towns of Oak Bluffs, Edgartown and Vineyard Haven. Bike paths are located right at the end of the road!brbrThe main entry level hosts a most attractive open dining and remodeled Kitchen featuring a blend of contemporary and farmhouse décor and a 52-inch QLED TV. Glass sliders open to the expansive 900 square foot deck and outdoor living area with sectional sofa and chaise lounges. Dine alfresco with outdoor dining for 8 and a 4-burner gas grill. This level includes two spacious master bedrooms, one with 55-inch QLED TV with surround sound and cathedral ceiling, and both with AC. They are nicely spaced for privacy with the newly renovated bath set between them. The bath includes a glass step in rain shower and body jets, and direct access to the enclosed outdoor shower, a favorite with visitors of the island. brbrA spiral staircase leads to the 2nd level living/media area which includes a 65-inch QLED TV with surround sound, sofa seating, home office area and glass sliders to an additional deck overlooking the protected lands adjacent to the property. Tucked just off the living area is a whimsical bedroom with trundle bed. The 2nd newly updated bath with step in rain shower is located on this level. Above the living room is a spacious and inviting loft bedroom for relaxing among the treetops in the Queen bed nicely cooled by the AC servicing the loft and living area below.brbrThe home is equipped with 5GB super high-speed internet, Leesa memory foam mattresses and cooling pillows, and 800 thread count Turkish linens. Upon arrival weekly guests are welcomed with a bottle of Veuve Clicquot Brut and all guests receive an Apotheke® amenity package!

ART FILLED BEACH COTTAGE IN THE PRIVATE WATERFRONT COMMUNITY OF WATERVIEW FARMS!

Oak Bluffs, Massachusetts, United States

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Bath

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$699.66

Welcome to paradise!!!brThis beautiful property is located in prestigious fresh pond estates. It sits tucked away in the woods off the main roads, plenty of privacy in a quiet neighborhood. Yet has easy access to beaches, bike paths and town,brJust 2 miles from the heart of oak bluffs & circuit avenue activities. brOak bluffs center offers, restaurants, movies, the nation's first carousel, shopping, and more beaches. brbrWe sanitize the entire place in-between each tenant. We wash all comforters each time someone new comes in, we bleach all surfaces and alcohol all door handles, toilet, air out the place for 24 hrsbrbrJust 500 feet from bike path, this property is centrally located a 2 minute drive to edgartown or vineyard haven. There is a sitting area at the pond with a dock and 4 Kayaks available for your use.(life jackets provided) Fresh Water swimming makes a wonderful place for the children to swim in a calm place without all the waves of the ocean. brLots of extras available on this wonderful property amenities include central air conditioning throughout the property, wifi, 3 TVs & laundry ,refrigerator with brspacious cooking area including outdoor patio with lots of sitting and eating areas and wonderful gas grill.The large, spacious apartment with amazing landscaping views is a place to remember. Great location for visitors with or without a vehicle. Public transportation close by.Tour the beautiful island of martha's vineyard. Stay in comfort. Shops, restaurants & galleries are a short drive away.brHistory of Oak Bluffs: Oak Bluffs is the quintessential old fashioned summer resort. Lively & upbeat, Circuit Avenue offers galleries, retail shops - clothing, crafts & jewelry, a variety of casual & upscale restaurants, ice cream parlors, pubs w/music, bicycle rentals, lodging & a harbor w/cafes & water-sports available. Ocean Park faces the water & is home to summer concerts & events. The gingerbread cottages dating back to the 1800s in the campgrounds surround the open air Tabernacle which offers services, community sings, art shows, high profile professional performing artists & political forums. Union Chapel bustles w/activity. Dancers, authors, artists. Farm Neck in Oak Bluffs is a world class 18 hole golf course frequented by presidents is just a mile away. visitors & locals alike love the golf course.Music & Aromas fill the air. Walk to the pond just 2 minutes away.. Not far from oak bluffs harbor where Island ferries come into the harbor on a seasonal basis. Buses are available to all island towns. Plenty of street parkingbrThe island truly offers something for everyone and a vacation experience that won't soon be forgotten.brThis house is located on an acre and a half of beautifully landscaped grounds with lots of trees and a beautiful pond with a dockbrJust a one minute ride to the bike trail, and 2 mile's to town. brWIFI included and as well as paid cable stations including over 100 cable channels. Farm Neck Golf Course just a mile away and the OB Library nearby. You'll never want to leave!brWe welcome you to our tastefully decorated home with all the charm and amenities that is all “Vineyard.” brThis meticulously maintained estate property offers a great atmosphere with all the amenities for a perfect vacation. Quiet, end of the road location yet really close to town. Wooded backyard with lots of beautiful landscaping, You couldn’t ask for more....brChildren's toys for all ages, x box station and a nintendo with many family friendly games. Over 25 board games and a closet full of toys for all ages. Many beach floats and lots of beach items included. Sand toys, coolers, beach umbrellas to name a few...

Apartment

Beautiful Landscaped Grounds and Pond & Kayaks

Oak Bluffs, Massachusetts, United States

Bed

Bath

Sleeps

$552.5

Sengekontacket pond in Oak Bluffs is waiting for you at this quiet 2-bedroom townhouse with a private deck overlooking a wooded back yard. Inside, you'll find a nice mix of comfort and convenience with a queen bed, and a twin over full bed bunk to accommodate 5 guests. We provide comfortable accommodations with amenities to help you enjoy your stay. Kitchen provides guests with a Cuisinart coffee maker, kettle, blender, toaster, dishwasher, gas stove & microwave. Enjoy the phenomenal amenities like a tennis & pickleball court, fresh water pond and Sengekontacket Coastal pond with dock access. Great for kayaking or paddle boarding. brbrThe unit has a washer/dryer, WiFi, 55” TV and 2 split AC units, one on each floor. The 2 bathrooms offer a bathtub (2nd floor) and shower (1st) for a relaxing stay. Our place is equipped for both long or short stays to make your holiday one to remember. brbrFor awareness, the unit is only accessible by stairs. brbrParking is underneath the building and has a MAX HEIGHT LIMIT OF 7 FEET. Please be sure your vehicle is not higher than 7 feet or it will not fit in the parking area. Unfortunately there is no street parking.brIf you have ANYTHING on top of your vehicle (kayak, roof rack, roof storage box, etc.) measure your vehicle height. You will have to remove items if the height is more than 7 feet. Please be careful of the height limit.brbrGetting Here: brMartha’s Vineyard is an island off the coast of Cape Cod, Massachusetts. You must access the island by ferry. The Steamship Authority is the most commonly utilized ferry service. Trips occur daily and frequently throughout the day. This is also the only ferry service that accommodates vehicles and reservations must be made in advance for vehicles. No reservation needed for passenger or bicycle travel. brSteamship Authority: www.steamshipauthority.com Phone: 508.477.8600. brMainland port: Woods Hole, MAbr2 Island Ports: brVineyard Haven Terminal: approx. 4 miles brOak Bluffs Terminal: approx. 4 milesbr - Advanced reservations required for vehiclesbrbrGetting Around:brbrYour personal vehiclebrVisiting the island with your own vehicle allows exploration of everything Martha’s Vineyard has to offer at your own pace and schedule. Free parking is available in most areas. brbrRental Cars are available on the island, and close by to both ferry ports.brFor more information about rental cars: http://web.mvy.com/Car-Renting-LeasingbrbrBicyclesbrMartha’s Vineyard is a very bike friendly island! Bring your own bike, rent from one of the many shops available on the island. brBike paths are present throughout the island, access to the bike path is at the end of the road on County Road – check out the MV Chamber of Commerce page for more info, including a map www.mvy.com/bikingmv.htmlbrbrPublic TransportationbrThe island of Martha’s Vineyard has a wonderful public bus system called The Vineyard Transit Authority (VTA). Bus service is reliable daily and year-round to all the towns on the island. Buses are readily available at both the Vineyard Haven and Oak Bluffs ferry terminals, as well as the airport. VTA buses are equipped with bike racks (first come first serve). Bonus: A bus stop is located 5 min walk from the townhouse. We are on Route #7 County Rd.brbrBeaches: There are many public beaches just a short drive away.br- Inkwell Beach, Oak Bluffs - 3.5 milesbr- Joseph Sylvia State Beach, Oak Bluffs (JAWS Beach) - 4.5 milesbr- Eastville Point Beach, Vineyard Haven - 4.5br- South Beach, Edgartown - 7.5 milesbr- Long Point Beach, West Tisbury - 7.5 milesbr- Moshup Beach, Aquinnah - 20 miles (worth the drive, visit the iconic Gay Head Light lighthouse while you are there - gayheadlight.org)

Charming 2-bedroom townhouse in Oak Bluffs with WiFi, AC

Oak Bluffs, Massachusetts, United States

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Bath

Sleeps

$1851.03

This charming Vineyard home recently completed a large renovation including all new bathrooms, a new, large bunk room and first floor master! It sleeps 12 in a perfect East Chop location! In minutes you can be on the beach or into town! It boasts 6 bedrooms all with air conditioning and heating units, three full newly renovated bathrooms, one half bathroom and has a lovely private outdoor shower! The fully renovated kitchen is perfect for cooking and gathering around the large custom farmhouse table. Soak up some time with friends and family on the beautiful front porch with plenty of seating for all with a large side yard for kids to play. Views of the sound and harbor. Back patio with seating to eat and relax as well as a propane grill for your use.brbrThere is a spacious, cozy living room and seating area for family gatherings. The first floor has a large master bedroom with a king bed and full bathroom. Upstairs there are two large bedrooms with king beds, a large bunk room with two sets of twin over full bunk beds that's perfect for kids, one room with two twin beds, and a third floor tower room with a full bed. All bedrooms have ceiling fans as well. There are two renovated full bathrooms upstairs. The front bathroom has a large shower and double sink. The rear bathroom has a large soaking tub, shower and pedestal sink. Television, cable and wifi throughout the house! Full size washer and dryer are in the back utility room. Linens, towels, beach towels and beach chairs are provided.brbrOur home is perfect for two or three families or one large one. Also a great getaway for friends to gather for special time together. Being located in the sought after neighborhood of East Chop brings tranquility and privacy, offering proximity to all amenities on the island! Make your memories in this perfect Vineyard charmer!

Charming 6 Bedroom Cottage in East Chop with Water Views! Walk to Beach & Town!

Oak Bluffs, Massachusetts, United States

Bed

Bath

Sleeps

$463.56

Enjoy a peaceful retreat in this cozy 2-bedroom, 2-bath condo with air conditioning, offering the perfect space to relax and unwind. Step outside onto the expansive deck—ideal for grilling, reading, or simply enjoying the refreshing breeze. The condo is situated in a private setting with access to a variety of outdoor amenities, including tennis courts, pickleball courts, and a serene freshwater pond. For water lovers, there's also a saltwater dock on Sengekontacket (Sengy) Pond, where swimming is allowed!brbrLocated near the Farm Neck Golf Course and the bike path, this condo is centrally positioned to explore all three of Martha’s Vineyard’s charming down-island towns—Vineyard Haven, Oak Bluffs, and Edgartown—each just a short drive away. Whether you're looking to relax or explore, this property is your perfect island getaway.

Quiet 2-Bed, 2-Bath Condo with Spacious Sundeck & Tennis Courts

Oak Bluffs, Massachusetts, United States

Bed

Bath

4

Sleeps

$761.64

Charming and comfortable 3-bedroom home in the heart of Oak Bluffs, perfect for a relaxing Vineyard escape. The home features two full bathrooms, central AC, a smart TV, and a sunny outdoor patio complete with a BBQ grill and seating for outdoor dining. Sleeping arrangements include one bedroom with a queen bed, one with a queen and a twin, and one with two full beds, offering flexible accommodations for families or groups. Just a short walk to downtown Oak Bluffs, beaches, ferries, shops, and restaurants, and centrally located for exploring the entire island. Ideal for your Vineyard getaway.

0.8 miles to Circuit Avenue in Downtown Oak Bluffs

Oak Bluffs, Massachusetts, United States

Bed

Bath

Sleeps

$1144.93

Property rents Monday to Monday. 3 bedroom/ 2 and 1/2 bathroom Contemporary Vineyard house with wraparound deck, outdoor shower, and new Kitchen. A modern airy (air conditioning throughout) home with a primary bedroom and adjoining bath on the main level with two additional bedrooms and bath on the second level. Loft space for additional sleeping/relaxing capacity. Second bedroom has queen bed with a twin and the third bedroom has 2 twin beds (that can be turned into a king) and the loft space has a futon/sofa bed. Total sleeping capacity 8/9.

Great Martha's Vineyard House: Everything You Need - Nothing You Don't!

Oak Bluffs, Massachusetts, United States

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Bath

Sleeps

$1232.24

Original 1900 Victorian home, updated in 2006, located in the historic Copeland District just one block from the beach. Three story home boasts decks and wrap around porch with ocean views from each. Five large bedrooms, spacious living room with French doors that open to the large wrap-around porch. Enjoy relaxing meals in the formal dining room and eat-in kitchen. Rec room in basement includes stone dry bar and 55' wide screen TV. Original wood paneling throughout. Fenced in back yard for privacy, perfect for post-beach barbecues. On Waban Park. 5 minute walk to town and Back Door Donuts; 1 minute hop, skip or jump to Oak Bluffs town beach/Inkwell.brbr

Big Beach House - Ocean Views!

Oak Bluffs, Massachusetts, United States

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Bath

Sleeps

$1015.35

Welcome to your home away from home! Experience the charm of Oak Bluffs in this spacious 3-bedroom, 2.5-bathroom beautifully designed home with modern amenities & cozy interior. Bathed in natural light and offering a prime location, this house is perfect for an unforgettable vacation. Enjoy a seamless blend of indoor comfort and outdoor serenity in this updated retreat.brbrThe home includes three bright and well-appointed bedrooms upstairs, each offering a comfortable bed and chic decor. The bedrooms are designed to ensure a restful night's sleep, with soft linens and thoughtful touches.brbrMaster Bedroom: Features a king-sized bed and an en-suite bathroom with a shower/tub.brbrBedroom 2: Bright and airy with a queen-sized bed and plenty of natural light.brbrBedroom 3: Includes a queen-sized bed and a twin-sized daybed with a trundle, comfortably sleeping four guests.brbrEn-suite Bathroom: Attached to the master bedroom with a shower/tub combination.brbrUpstairs Hall Bathroom: Includes a shower/tub combination.brbrHalf Bathroom: Conveniently located downstairs.brbrOutdoor ShowerbrbrThe open-plan living area is stylishly decorated, creating a warm and inviting atmosphere. Relax in the spacious main living area, which comfortably seats 8+ guests with plush sofas, large windows, and a flat-screen TV. brbrThe secondary room features a queen-sized pullout Tempur-Pedic sofa bed and provides a cozy spot to unwind with a good book or enjoy the company of loved ones.brbrOur home features a spacious, upgraded fully equipped kitchen with modern appliances and ample counter space, perfect for preparing delicious meals. The open-plan dining area comfortably seats 8, creating a welcoming space for family meals and gatherings.brbrStep outside to the inviting back patio, where you can relax with a morning coffee or enjoy an evening under the stars. The patio includes a BBQ and an umbrella-shaded dining table, perfect for outdoor meals and relaxation. The spacious backyard offers plenty of room for outdoor activities and enjoyment. Savor the tranquil garden views in this serene and private outdoor space.brbrLocated just a short walk from Oak Bluffs, you can easily explore the town's vibrant shops, restaurants, and local attractions. With a perfect mix of modern amenities and cozy charm, this house is ideal for short-term and long-term stays. Book your stay today and start creating unforgettable memories in Oak Bluffs!

Oak Bluffs Retreat! Spacious Vineyard Home Near Beaches & Downtown

Oak Bluffs, Massachusetts, United States

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Bath

Sleeps

$922.03

Pirate's Cove is a young, Victorian-style home, designer-decorated and nestled on a quiet lane in East Chop, located just minutes away from all the charm and activities Oak Bluffs has to offer. The beach, harbor, and town are all just a pleasant 15-18 minute walk away, or less than a 5 minute drive/bike ride.brbrNEW UPGRADES: The kitchen has been remodeled to included fresh cabinetry, gorgeous dark gray quartz countertops, and white subway tile backsplash. The first floor bathroom has also been remodeled top to bottom, to include new flooring, new vanity, and a white floor-to-ceiling tiled, zero-entry shower.brbrThis air-conditioned home has a newly renovated eat-in-kitchen and separate dining room that can accommodate up to 9 guests. The living room is accented by a 40-inch Samsung SmartTV, and a charming beach stone fireplace.brbrUpstairs, the spacious master en suite features a warm blue color decor, 40-inch Samsung SmartTV, and a separate attached room that makes for a great office, sitting room, or nursery, and the bathroom features a mosaic-tiled shower. The first floor bedroom has a queen bed, 32-inch Samsung SmartTV, and right outside the door, a fully renovated full bathroom, complete with new flooring, a new vanity, and a beautiful floor-to-ceiling tiled shower. The two upstairs bedrooms each have two twin beds, including one with a trundle, and share the full hallway bathroom. The twin beds can also be converted into king beds.brbrDownstairs you will find a finished basement with a full bathroom, laundry room, 48-inch SmartTV, and an arcade machine – perfect for rainy day activities.brbrThe front porch is equipped with rocking chairs perfect for a quiet afternoon reading or relaxing. Outside is a large deck, Weber gas grill, patio furniture, a backyard, and a hammock, which provides a great environment for cookouts and gathering with friends and family. An outdoor shower enables you to rinse off after a long day at the beach. There is ample parking for two cars in the driveway. The home has blazing fast 1,200 mbps (1+ gigabyte) WiFi, for when you want to stream your favorite TV shows and movies from the multiple Samsung SmartTVs throughout the home.brbrThis is a quintessential Martha’s Vineyard vacation home!brbrMinimum age to rent is 25 years-old.brbrNO pets and NO smoking. Please do not move the furniture.brbrThe cleaning fee covers cleaning, linens, towels, and the cost of laundering. Guests are subject to an additional $250 cleaning fee if grill not cleaned adequately after use.brbrWe have consulted sources such as the Centers for Disease Control (CDC), Environmental Protection Agency (EPA), and World Health Organization (WHO). We are also implementing best practices from some of the top medical and hospitality institutions in the world to ensure we have the best cleaning and disinfecting protocols. Please rest assured that a clean home for our guests is of the utmost importance to us.brbrThis is a Getaway Society vacation rental home. Please ask us about our portfolio of homes in Martha's Vineyard, Hilton Head, Orlando, Gatlinburg, Sandbridge Beach (Virginia), Broken Bow (Oklahoma), and the Pocono Mountains. Our vacation rental properties are perfectly located and stylishly designed to help you create an amazingly memorable experience on every single getaway. Visit our website for more information.

The quintessential MV home. Now booking for 2026!

Oak Bluffs, Massachusetts, United States

Bed

Bath

Sleeps

$480.31

Enjoy all that Martha's Vineyard has to offer in this spacious two bedroom, two full bath beautifully furnished condo overlooking the ocean. Steps to the beach and a short walk to town, this location makes visiting the Vineyard with or without a vehicle easy. There is also a full kitchen with all appliances including washer and dryer. FREE WiFi INTERNET and cable TV allow you to stay connected. Enjoy the view of the ocean from almost every room is this condo including the deck. There is also an air conditioner in the unit. brbrSorry, no pets and no smoking allowed. Email or call with questions.

Condo

Martha's Vineyard Beachfront Condo in Oak Bluffs

Oak Bluffs, Massachusetts, United States

Bed

Bath

Sleeps

$989.2

Relax on the gorgeous wraparound deck, let the sea breeze caress your face, listen to the chirping birds, and drink in the views of a pristine Lagoon Pond on the island of Martha's Vineyard. This classic deck home was built in the 1970s on a sandy hillside overlooking the water, but has been well maintained and improved over the years. Tucked in the woods on 1.5 beautifully landscaped acres, it features:br• Peace and quietbr• View to die forbr• Wrap-around wood deck with built-in bench seatingbr• Easy access to a private, sandy beachbr• Air Conditioning with mini-splits installed in 2020br• 4 bedroomsbr• 2 full baths, recently renovated, both with glassed-in shower enclosuresbr• Enclosed outdoor showerbr• Open-plan living room and dining area opening onto the deck br• 42-in flatscreen HD TV with HD DVR in living roombr• Wireless internet accessbr• Boat mooringbr• Easy access to extensive bike path network br• We provide pillows, mattress pads, blankets and dish towels. You must bring or rent bed linens, blankets, bath towels and beach towels.brbrbr

Lovely waterfront home with private, sandy beach and mooring on Lagoon Pond

Oak Bluffs, Massachusetts, United States

Bed

Bath

Sleeps

$1093.06

This gorgeous, contemporary air-conditioned private home is perfect for your luxurious vacation on the island. It is 2700 sq ft of well laid-out space and sits on 1.4 acres of land in a private wooded area, centrally located, only minutes from downtown Oak Bluffs and beautiful beaches.brbrThe cathedral ceiling allows spectacular natural light throughout the living area inviting all to mix and mingle. When sitting in any room in the house, the large windows allow you to enjoy the trees swaying in the wind as if you were standing in the middle of the forrest. The screened in porch invites you to take a step outside for a nature walk or simply enjoy a meal with a light breeze from the yard. brbrAll four bedrooms have private bathrooms and one bedroom opens up onto a private balcony. The lower floor can serve as a separate unit with it's own bed/bath, living room, and half kitchen.brbrThe comment we consistently receive from out guests is 'you have a beautiful home'

Secluded Escape- Central AC & Wireless Internet Access.

Oak Bluffs, Massachusetts, United States

Bed

Bath

Sleeps

$743.36

Prime location close to the center of town in the fabulous SeaView Condo building in the heart of Oak Bluffs. Highly desirable property with stunning ocean views from nearly every window with this larger well-appointed recently upgraded (Winter 2021/2022) corner unit. Open Living and Dining areas, plus cozy beach-and-park-facing deck, as well as a well-equipped Kitchen. The Master Bedroom has a full bath with luxury shower and opens onto the deck with its grand water and breath-taking sunrise views. There is a second Bedroom and full bath with tub/shower. The condo building association also has an outdoor shower and small grilling area. This is the place for your summer vacation, steps to The Inkwell Beach right across the street! Everything in very close proximity and walking distance: parks, restaurants, shopping, boats, bike path, and even the Oak Bluffs ferry, so no car needed! However, there is one free parking space available for the unit should you choose to bring a vehicle. Golf and tennis also down the road. Great for couples and small families. We have had many satisfied, repeat visitors. Air purifiers (with HEPA filters) and A/C unit also available.

Condo

Spacious Waterview Condo - Steps To The Beach, Right Across The Street!

Oak Bluffs, Massachusetts, United States

Bed