Vacation Home Rentals By Owner In Oak Bluffs, MA

$1000.36

Charming home near downtown & beach with patio, outdoor shower, grill, & W/D

Oak Bluffs, Massachusetts, United States

Summary:brbrBlissful Island HavenbrbrbrbrThe Space:brbrCentrally located within a half-mile of Inkwell Beach and a mile of downtown Oak Bluffs, this charming home is the perfect choice for your next escapade with family and friends! This convenient location situates you within a short drive of amazing restaurants and must-visit attractions, including Alley/Waban Park, Farm Pond Trail, Oak Bluffs Town Beach, Flying Horses Carousel, Joseph Sylvia State Beach, Martha's Vineyard Camp Meeting Association Cottage Museum, and Tabernacle in Oak Bluffs. The home boasts a fantastic outdoor space with a dining table to dine alfresco with fantastic views, a gas grill for summertime barbecues, and a lounge area with comfy patio seating protected from the sun by a large patio umbrella. The enclosed outdoor shower is perfect for rinsing off after a memorable day at the beach. Inside, the home welcomes you with a bright and inviting living area where you and your group can spread out comfortably while the chef of the group surprises everyone with a delicious homemade meal. The spacious eat-in kitchen has been appointed with modern appliances that will make cooking a breeze, an island with seating, and a dining table. Additional perks include a washer/dryer and board games. bThings to Know/bbrbrGuests must be 25 years or older to book this property.

4

Bed

3

Bath

8

Sleeps

$1015.9

/ Nightly

Private Vacation Home

Serene private home w/ large deck & yard on conservation land

Oak Bluffs, Massachusetts, United States

Summary:brbrThe Big EasybrbrbrbrThe Space:brbrWelcome to your perfect family getaway in Oak Bluffs, MA! Nestled on a serene cul-de-sac, this spacious house sits on a private acre of land surrounded by conservation woods, making it an ideal retreat for families with children. With a well-manicured front and back yard, there’s plenty of space for outdoor games and activities, ensuring endless fun for everyone. The expansive 24 x 40 ft deck is the highlight of this home, featuring comfortable seating for up to 40 guests, making it perfect for entertaining. Enjoy al fresco dining at the two 6 ft. tables or the cozy round table with an umbrella. The retractable awning provides shade when needed, and an outdoor shower adds a refreshing touch after a day at the beach. Conveniently located just a 10-15 minute drive from many beautiful beaches (beach gear provided), you’ll also find yourself close to Manuel F. Correllus State Forest, Farm Neck Golf Club, and the Mass Audubon’s Felix Neck Wildlife Sanctuary. For those who enjoy outdoor activities, the nearby Vineyard Baseball Park, Y, and skateboard park are within walking distance, as well as a bus stop for easy transportation around the island. Inside, the home is equipped with modern amenities including central AC, WiFi, and a fully stocked kitchen with everything you need to prepare meals. With a dog-friendly policy, your furry friends are welcome to join in on the fun. Whether you’re looking for adventure or relaxation, this Oak Bluffs home is the perfect base for your family vacation. Book your stay today and create lasting 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

Bath

Sleeps

$470.4

/ Nightly

Private Vacation Home

Quintessential Martha's Vineyard cottage with yard/patio - walk to Inkwell Beach

Oak Bluffs, Massachusetts, United States

Summary:brbrThe PinkletinkbrbrbrbrThe Space:brbrFull of classic island charm and beautiful views of the surrounding brush and wetlands, this authentic Oak Bluffs cottage offers the quintessential Martha's Vineyard experience. Walk or ride your bikes into town and to Inkwell Beach, and be greeted back at home by a serene setting you won't find anywhere else. Named for the island's tiny frogs that mark the arrival of spring, The Pinkletink sits on a quiet, one-way street that backs up to protected wetlands. Take in views of nesting birds and native vegetation as you sip your coffee in the mornings, before getting ready to walk less than half a mile to Inkwell Beach. Also within a one-mile stroll are the ferry terminal, the Flying Horses Carousel, the shops and restaurants of Circuit Avenue, and a number of lovely town parks. Come home from a day at the beach to unwind in the backyard, relax with a good book and a cold drink, and light the gas grill for an afternoon barbecue. There's even an outdoor table and chairs, so you can dine in the fresh ocean air as the sun begins to set. The interior is incredibly atmospheric, with richly hued wood paneling adorning the walls. Yet the space is also newly furnished and thoughtfully renovated, with the kitchen offering a new refrigerator, a new sink, new flooring, and new quartz countertops. Enjoy a living room with a smart TV, an air-conditioned sun porch where you can play board games by the window, and complimentary WiFi throughout the cottage. bTHINGS TO KNOW/b There is no mail or package delivery to this home. There is no washer/dryer. Quiet hours are from 10:00 PM to 8:00 AM

Bed

Bath

Sleeps

$552.72

/ Nightly

Private Vacation Home

Quaint, ranch style home in Oak Bluffs with central air

Oak Bluffs, Massachusetts, United States

Summary:brbrThe RootskellerbrbrbrbrThe Space:brbrNestled at the end of a tranquil cul de sac, this charming cabin-style home in Oak Bluffs, MA, offers a warm and inviting ambiance that welcomes you from the moment you arrive. With its updated exterior and cozy interior, this property serves as the perfect home base for those eager to explore the beauty of Martha's Vineyard. The open layout and quaint decor create an inviting atmosphere, ideal for unwinding after a day filled with adventure. The fenced in yard is the perfect place to relax and watch the children playing. Enjoy movie nights on the flatscreen TV or simply relax with loved ones in this delightful retreat. Conveniently located just a mile from the Oak Bluffs Ferry and the picturesque village green, you'll find yourself in close proximity to the island's vibrant entertainment and dining options. The famous gingerbread homes of Oak Bluffs are also nearby, adding a touch of charm to your stay. For beach lovers, Inkwell Beach is just a short drive away, perfect for soaking up the sun and enjoying the ocean breeze. If you're a golf enthusiast, the immaculate greens of Farm Neck Golf Club await just a quick drive from your doorstep. This home is not only a serene escape but also a gateway to the island's many attractions. Film buffs will appreciate the proximity to the iconic Jaws Bridge, located just five miles away. Whether you're interested in whale watching, kayaking, or simply exploring the local shops and restaurants, Oak Bluffs has something for everyone. After a day of exploration, return to your cozy haven, where you can enjoy the comforts of home, including a fully equipped kitchen and outdoor dining area. With amenities such as central AC, a washer/dryer, and a spacious deck, this Oak Bluffs home is designed for your comfort and convenience. Experience the best of Martha's Vineyard while enjoying the rustic charm of this delightful property. Book your stay today and create unforgettable memories in this beautiful island getaway! Things to Know

4

Bed

2

Bath

7

Sleeps

$633.03

/ Nightly

Private Vacation Home

Bright old-world cottage with two porches & large yard - walk to town & beaches

Oak Bluffs, Massachusetts, United States

Summary:brbrOak Bluffs CottagebrbrbrbrThe Space:brbrSavor the old-world charms of Oak Bluffs Cottage, an ideally situated Martha's Vineyard getaway with a two-level porch to enjoy quiet island mornings and evenings! Take advantage of the provided beach chairs as you spend fun summer days in the sun and come home from the beach to prepare meals for the whole family in the full kitchen, or opt for an outdoor barbecue with the provided grill, the spacious yard, and the shaded deck. Don't worry about the heat, as there are new ductless mini-split air-conditioning units in the common areas and all three bedrooms. What's nearby: This home is conveniently located on the edge of downtown Oak Bluffs, just over half a mile west of the ferry terminal. You'll be within easy walking distance of great restaurants, a market, coffee shops, incredible seafood, and the historic Flying Horses Carousel. The home is also only three-quarters of a mile from Inkwell Beach, Oak Bluffs Town Beach, Ocean Park, and the marina. Things to know:

Bed

Bath

Sleeps

Select Dates for Price

Private Vacation Home

Enchanting bungalow with golf nearby, full kitchen, central AC, & washer/dryer

Oak Bluffs, Massachusetts, United States

Summary:brbrEast Chop 90brbrbrbrThe Space:brbrWelcome to coastal living on the East Chop, a perfect place to bring loved ones for a getaway from the hustle and bustle of everyday life. This renovated home is full of contemporary creature comforts but honors the character and charm of old vineyard living. Rent water equipment to spend your days on the ocean kayaking, paddleboarding, sailing, surfing, and every other waterfront activity imaginable. Bring your golf clubs for world-class greens nearby, and enjoy exquisite walkable neighborhoods full of Martha's Vineyard magic. The architectural style draws one immediately to the wrap-around porch. Upon entering the home, the sparkling vintage fir floors, beadboard wainscoting, and a beautiful place to relax and unwind awaits. Many viewing windows and french doors bathe the rooms in natural light, creating a perfect cozy atmosphere. Relax and make yourself at home by resting on the plush furniture, streaming your favorite movies on the large TV, or curling up with a good book. Create culinary charms in the sophisticated galley-style kitchen, equipped with stainless steel appliances, a breakfast bar, and a dining table. Comfortable beds in spacious bedrooms ensure that everyone will enjoy a wonderful night's rest from the day's adventures. In the guest house, you'll find a nice flex space and kitchenette with a mini-fridge, microwave, and toaster oven. A studio guest room with an en suite bathroom makes this a great private space for those who want their own accommodations. bTHINGS TO KNOW/b To use streaming services, guests must log in with their own credentials.

Bed

Bath

Sleeps

$859.12

/ Nightly

Private Vacation Home

Private island house with close beach access and water view from deck

Oak Bluffs, Massachusetts, United States

Summary:brbrSoundmeadow HousebrbrbrbrThe Space:brbrLocated just outside the charming town of Oak Bluffs, MA, this delightful house is the perfect retreat for your next vacation. Just a stone's throw away from the renowned Farm Neck golf course, this home offers a tranquil setting with private community water access on Sengekontacket, the saltwater pond where scenes from the iconic movie JAWS were filmed. Enjoy the picturesque views from the house or take a short walk through the community meadows to reach the dock and small sandy beach, ideal for families with young children during the summer months. This dog-friendly property boasts a plethora of amenities to ensure a comfortable stay for all guests. From a well-equipped kitchen with modern appliances to a smart TV for streaming services, a gas grill on the deck for outdoor cooking, and a trunk filled with board games and movies for indoor entertainment, there's something for everyone to enjoy. The washer/dryer and mini split AC system add convenience and comfort to your stay. Explore the surrounding area and take advantage of the various activities available, from stand-up paddle boarding on the bay to whale watching, fishing, kayaking, and more. 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 perfect home base for your Martha's Vineyard getaway. Book now and start planning your dream vacation! 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.

2

Bed

2

Bath

10

Sleeps

$686.78

/ Nightly

Private Vacation Home

Oak Bluffs Home with Renovated Screened-in Porch - Short Drive to Beach

Oak Bluffs, Massachusetts, United States

Summary:brbrFallen Oak RetreatbrbrbrbrThe Space:brbrLocated in the historic Oak Bluffs neighborhood, this recently remodeled 3BR/2.5BA home is close to beautiful beaches, art galleries, and charming local shops. Relax with a crisp drink on the newly renovated screened sun porch complete with an outdoor porch and gas grill. You’ll love the convenience of a living room on each floor, both featuring big screen televisions. Warm wood accents throughout add a coastal New England touch. LIVING AREA The main and second living rooms are both equipped with big screen TVs and ample comfortable seating for everyone. KITCHEN & DINING Cook tasty meals in the kitchen, outfitted with a full suite of new appliances complimented by new flooring. The dining table and breakfast nook each offering seating for four. BED & BATH This home sleeps up to six guests between three bedrooms. All of the bedroom mattresses have been recently upgraded. The primary bedroom offers a queen-sized bed and a new big screen smart TV. The en-suite bathroom is equipped with a walk-in shower. The second bedroom is outfitted with a queen-sized bed and a new smart TV. The third bedroom contains two twin beds and a new smart TV. The guest bathroom has a tub/shower combination. A half bath adds convenience. OUTDOOR AREA & AMENITIES The newly renovated screened sunporch offers plenty of seating to relax and enjoy the summer breezes. Fire up the new gas grill and cook dinner on the side porch. EXTRA PERKS & MORE DETAILS Extra perks include complimentary Wi-Fi, cable TV, and a washer/dryer. New carpeting and flooring have been installed throughout the second floor. This home is equipped with new window AC units. Parking is available for up to two cars in the driveway. Access to this two-story home is via two steps at the entryway.

Bed

Bath

Sleeps

$1285.13

/ Nightly

Private Vacation Home

House with guest studio close to town and beach with grill, games, AC & patio

Oak Bluffs, Massachusetts, United States

Summary:brbrSankofa Martha's VineyardbrbrbrbrThe Space:brbrNestled in the historic Vineyard Highlands at the beginning of the African American Heritage Trail, this charming home with included studio offers a unique and inviting retreat for your vacation. The newly renovated cottage-style house is located in the sought-after East Chop area of Oak Bluffs, 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 9 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. The property also includes Sankofa Studio, a fabulous studio apartment for additional space and privacy. 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

3

Bath

9

Sleeps

$645.94

/ Nightly

Private Vacation Home

Coastal Retreat | Walk to Inkwell Beach, Dining & Flying Horses Carousel

Oak Bluffs, Massachusetts, United States

Summary:brbrOak Leaf Cape CottagebrbrbrbrThe Space:brbrLocated walking distance to the center of Oak Bluffs, this 4BR/2BA home offers a relaxing retreat close to all the action, with plenty of room to spread out and get comfortable. Stroll to Inkwell Beach or an array of local eateries. Walk to the ferry dock and set off on a scenic day trip to Nantucket. Dine alfresco at a shaded patio table in the yard. You’ll love the charming feel of this warmly decorated home. LIVING AREA The inviting living area features a variety of seating and a TV. KITCHEN & DINING Prepare tasty meals in the kitchen, outfitted with a full suite of appliances. The dining table seats eight. BED & BATH This home sleeps eight guests between four bedrooms. The primary bedroom is furnished with a queen bed. The en-suite bathroom has a tub/shower combination. The second bedroom is equipped with a queen bed. The third bedroom is appointed with a full-size bed. The fourth bedroom includes two twin beds. The guest bathroom has a walk-in shower. OUTDOOR AREA & AMENITIES The front lawn provides a dining table with an umbrella. EXTRA PERKS & MORE DETAILS Extra perks include complimentary Wi-Fi, cable TV, and a washer/dryer. Parking is available for three cars in the driveway. Street parking is not available. This home has a two-story layout. The living room fireplace is not operational. The property does not have air-conditioning. LOCATION Stroll 18 minutes to Inkwell Beach or 11 minutes to Ocean Park and the Flying Horses Carousel, the oldest-operating platform carousel in the country! Walk 8-10 minutes to local eateries and essentials shopping. Hit the links at Farm Neck Golf Club. Board the ferry and take a day trip to beautiful Nantucket Island.

4

Bed

2

Bath

8

Sleeps

$1898.71

/ Nightly

Private Vacation Home

Lagoon Waterfront 4 Bedroom Private Sandy Beach Oak Bluffs Martha's Vineyard

Oak Bluffs, Massachusetts, United States

Idyllic Lagoon Front Vacation Home – Oak BluffsbrbrThis 4 bedroom, 3.5 bath retreat is the perfect escape for a memorable Martha’s Vineyard summer. Nestled on the shores of Lagoon Pond, the home offers a private sandy beach and unobstructed panoramic water views. Enjoy summer recreation right at your doorstep with fishing, clamming, and two kayaks provided.brbrFully refreshed in 2025, the property sparkles with stylish, comfortable furnishings. The home offers four sleeping areas: two ensuite bedrooms and two additional bedrooms that share a bath. A bonus lower level includes a kid-friendly TV lounge complete with large screen TV and Ms. Pac-Man arcade game.brbrAccommodates up to 8 guests. Saturday-to-Saturday rentals.

3

Bed

1

Bath

8

Sleeps

$592.64

/ Nightly

Private Vacation Home

Family Home Near Arts District & Inkwell Beach

Oak Bluffs, Massachusetts, United States

Family Home Near Arts District & Inkwell BeachbrbrFamily-Friendly Home with Backyard – 1 Mile to BeachbrbrBring the whole family to Martha’s Vineyard for a vacation filled with comfort, fun, and lasting memories. This welcoming Oak Bluffs home is designed with families in mind, offering plenty of room to relax and play both indoors and out.brbrStep outside to a private backyard—perfect for kids to run around while the grown-ups fire up the grill. Gather around the picnic table for easy outdoor meals, or enjoy quiet mornings on the porch and evenings on the patio.brbrInside, you’ll find a fully equipped kitchen for family meals, plus a living room with comfy seating—ideal for game nights, story time, or simply relaxing together. A TV with cable and DVD player makes movie nights easy after a day at the beach.brbrWhat Families Will Love Nearby:brbrJust a short distance from local Oak Bluffs Beaches including Marinelli Beach, Inkwell and State Beach which are great for swimming and sandcastle building. brbrA short bike ride or walk to the Oak Bluffs’ Circuit Avenue for ice cream, an arcade, and of course the historic Flying Horses Carousel. brbrAlso walking distance for full service shopping at the island staple Tony’s Market.brbrThis farmhouse has a quintessential Vineyard vibe, an unbeatable location that’s close to both town and the beach, it is the perfect spot for your next family getaway.

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

$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

$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

$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

$829.34

/ Nightly

Private Vacation Home

Family friendly, walking distance to town, harbor, shops, restaurants, beaches

Oak Bluffs, Massachusetts, United States

Summary:brbrCanary CottagebrbrbrbrThe Space:brbrExperience the Martha's Vineyard of yesteryear at this beautifully updated historical home, ideally located near the heart of Oak Bluffs. The ferry terminal, the Flying Horses Carousel, Oak Bluffs Town Beach - it's all within a half-mile stroll. This two-story home has stood on Brunswick Avenue since 1870, with a classic, covered front porch where you can relax in the afternoons. It's a wonderful location for walking to dinner, visiting the East Chop Lighthouse, and spending your days on Inkwell Beach or Joseph Sylvia State Beach. Begin and end each day outside on the porch, which offers plentiful space for sipping morning coffee, playing board games in the afternoons, and sharing alfresco dinners with your loved ones. The interior has been thoughtfully updated with modern comforts while preserving the home's 150-year-old character. White walls and ceilings reflect the natural sunlight, two living rooms offer TVs with cable and streaming capability, and the eat-in kitchen is equipped with stainless steel appliances. Find a stacked washer/dryer for your swimsuits and towels, complimentary WiFi throughout the house, and uncluttered bedrooms to provide a restful night's sleep. bTHINGS TO KNOW/b Upstairs bathroom has a small shower Streaming services are available, but guests must log in using their accounts. Air-conditioning is comprised of window units which are only available in the living area and three bedrooms.

5

Bed

2

Bath

6

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

$695.96

/ Nightly

Private Vacation Home

Inviting, two-story home with a large yard, sunroom, balcony, & washer/dryer

Oak Bluffs, Massachusetts, United States

Summary:brbrGingerbread DreambrbrbrbrThe Space:brbrExperience the laidback lifestyle of the Vineyard from this classic, two-story Oak Bluffs vacation rental! Located just a short walk from downtown and the ferry, this home is ideal for those seeking easy access to the coast, local beaches, and an abundance of other family-friendly attractions. Enjoy a leisurely bike ride, check out the Flying Horses Carousel (the oldest platform carousel in the country!), then spend your afternoon swimming in the warm waters of Nantucket Sound. Or, venture to Joseph Sylvia State Beach, ideal for beachcombing, windsurfing, and fishing for striped bass. Timeless attractions like Martha's Vineyard Performing Arts Center, Flying Horses Carousel, Reliable Market, and Inkwell Beach are all within a three-mile radius. Or check out Obama's favorite Vineyard green, Farm Neck Golf Club. Brimming with plenty of old-school New England charm, this delightful getaway invites you to enjoy its many comforts and amenities. Brew up your morning coffee or prepare mealtime masterpieces in the bright, full kitchen, then gather in the adjacent dining room or just outside in the furnished and screened sunroom. Stream your favorite channels on the available TVs or bust out a few of the provided board games on rainy days or relaxing nights in. This home also offers a furnished front porch, an outdoor shower with a convenient changing area, and a private washer/dryer to let you pack light and keep your laundry under control during your stay. bThings to Know/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.

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

Vacation Home Rentals By Owner In Oak Bluffs, MA

$1000.36

$1015.9

$470.4

$552.72

$633.03

$859.12

$686.78

$1285.13

$645.94

$1898.71

$592.64

$1094.26

$1336.59

$1605.76

$607.16

$829.34

$441.77

$695.96

$814.98

Rent a place that suits your needs

Most popular vacation rentals in Oak Bluffs

$2204.99

$2226.16

$2960.05

$3015.90

$3248.61

$3591.16

$3725.20

$1108.69

$1076.68

$1076.81

Most Popular Cities in Massachusetts