Vacation Home Rentals By Owner In Oak Bluffs, MA

$595.73

WALK TO BEACHES,HARBOR,EVERYTHING!! IN-TOWN OB! Deck,A/C,Outdoor Shower, Wifi

Oak Bluffs, Massachusetts, United States

***IMPORTANT--PLEASE MESSAGE HOST FIRST----BEFORE SENDING A BOOKING REQUEST!! ( JUST CLICK ON CONTACT HOST (you will find 'CONTACT HOST on the bottom of the listing on the mobile app and on the full website CONTACT HOST' will be located just under where it says request to book ) THEN SEND MESSAGE ) **** brbr**This bright & sunny, adorable,colorful home is filled with Vineyard charm!**** Great location!! Convenient IN-TOWN Oak Bluffs location - WALK TO EVERYTHING !!! : BEACHES, Flying Horses, Arcade, Movie Theater, ferry, harbor/marina, shops, art galleries, restaurants, outdoor bars,bike path, playgrounds, public library, ponds, walking trails, gingerbread cottages, parks, tennis, basketball courts , baseball field, golf, groceries. **INCLUDES: FOUR AIR CONDITIONING UNITS ( 1 A/C IN EACH BEDROOM, ALSO 1 IN THE OPEN LIVING/DINING ROOM),HI-SPEED WIRELESS INTERNET, 3 flat-screen TVs with ROKU. BEACH CHAIRS , COOLERS, BEACH UMBRELLA, BOOGIE BOARDS** Relax in the hammock. Features include hardwood floors, open living/dining room with BRAND NEW SOFAS ( one is a queen sleeper). There is a full bathroom with shower and bath on the 1st floor and there is also a private hot water outdoor shower as well.The large enclosed outside hot water shower has tea lights for evening showers. Large back deck w/ furniture (built-in bench seating, dining table with lots of chairs, 4 cushioned loungers, Weber gas grill.). White tea lights for evenings relaxing and entertaining on the deck. Inside, you'll love the eat-in country kitchen. Ideal home for people who like to be near everything. Partially fenced-in yard (back and both sides fenced), Off-street parking in two large driveways. Famous Tony's Market is just steps away. Three bedrooms ( 2 queens, 3 twins (one is a rollaway bed that can go in any room), sleeps 8 max ** Stereo/ radio, books, maps and Vineyard guides. Just a short walk to the gingerbread cottages and gardens , where you can attend a summer concert ,or be there for historical Illumination Night or the fabulous annual fireworks. Meet friends at the harbor for cocktails & great food at one of the many restaurants & shops. The kids will love the game room, candy shop, fudge shop, Flying Horses Carousel, ice-cream shops, Ocean Park and the movie theaters. THERE IS ALSO A WASHER & DRYER!

Bed

Bath

Sleeps

$2034.86

/ Nightly

Private Vacation Home

Spacious 5-bedroom house with AC and WiFi in brilliant Oak Bluffs

Oak Bluffs, Massachusetts, United States

Perched on a grassy hill, this majestic home has sweeping views of Oak Bluffs Harbor and is just minutes from East Chop beach. Stylishly decorated and thoughtfully renovated, this charming property offers modern amenities and is the perfect family retreat. The first floor has living, kitchen and dining areas. The living area, just beyond the front entrance and open covered porch, has couch seating and a decorative stone fireplace. The large eat-in dining room has seating for eight. The kitchen has commercial stainless appliances, butcher block counters, a large island for meal preparation and table that seats four. The first floor also has a laundry room, powder room and queen bedroom with private bathroom. The four remaining bedrooms are located on the second floor. The primary Master bedroom has an ensuite bathroom, sitting area, work area, vaulted ceilings, and a stunning waterview from a private balcony. The second Master bedroom has an ensuite bathroom, sitting area and TV. Two additional bedrooms share a full bath in the hallway. The queen bedroom has a water view and small desk area. From the second floor, there is a set of stairs to the observatory, where there is bench seating and 280 degree water views of Nantucket Sound, the Steamship Ferry, and East Chop beach. A perfect spot to read, meditate, or watch the sunrise. Fronting East Chop Drive is a spacious outdoor stone patio and flower garden. The large wraparound porch is perfect for morning coffee, lazy summer afternoons and evening conversation. In the back, there is a stone patio with table, seating for six, umbrella as well as a large area for parking four of more cars in addition to the two parking spots along East Chop Drive. A large outdoor shower (6’- 0” L x 4’- 0” W) with hot and cold water and bench is appropriately located on the side of the house. Conveniently located steps from the beach and less than a mile from the heart of Oak Bluffs, this magical home has it all!brbr

Bed

Bath

Sleeps

$617.33

/ Nightly

Private Vacation Home

Perfect Family Home- Oak Bluffs, Martha's Vineyard

Oak Bluffs, Massachusetts, United States

Our wonderful family house is exactly what you're looking for to compliment your Martha's Vineyard vacation. The house's wonderful location is nestled quietly a short distance (2 miles) from downtown Oak Bluffs, the many area beaches, public golf courses, plus 2 miles from the OB and VH ferries and 10 minutes from airport. Not only does the house have 3 bedrooms, but it also has 3 full baths to match. Whether you're a family with children, or 3 couples looking to enjoy an Island vacation, this house is more than you've hoped for. We have all the kid stuff you need like 2 Pack n Plays, High Chairs, books & toys. There is plenty of parking, all recently updated appliances, we are sure that you'll fall in love with this house just as much as we did.

Bed

Bath

Sleeps

$636.69

/ Nightly

Private Vacation Home

Water View 1 mi from Oak Bluffs 10 min Walk to Beach

Oak Bluffs, Massachusetts, United States

Beautiful water view, spacious natural landscape, and privacy enhance the serenity of our rustic barn-style home tucked on 3 acres located 1 mi from the center's of Oak Bluffs and Vineyard Haven, groceries, shops, dining, nightlife, and bike, car, watercraft rentals. Bike path direct access from property. Bus stops nearby for transit to all island towns, beaches and sights.brbrOur property was originally a barn built in 1870. Preserved original architectural features such as 15 foot pitched ceilings, exposed beams, barn wood, shiplap, and open concept interior design are all hallmarks of this rustic barn-style home.brbr1st floor is an open kitchen, dining and living area which opens on to the deck overlooking the pond. Queen bedroom, and full bath are off the living area. Entire 2nd floor is an enclosed loft 21' x 16' King bedroom with 15' vaulted ceiling, balcony overlooking the pond, 1/2 bath, plus a daybed. Memory foam mattresses, wide variety of nice pillows to suit all preferences, and 100% soft cotton sheets, blankets, quilted spreads and comforters. Interior furnishings throughout are very comfortable. Big deck overlooking the pond has lots of seating, dining table, and gas grill. Additional outdoor shower is off the deck. There is lots of private outdoor space and plenty of parking.brbrAmenities include, heat/AC, cable and high speed wifi, 42 living room and 50 king bedroom smart HDTVs, speakers with audio input for all types of devices, microwave, coffee maker, blender, paper towels, dish soap, cleaning supplies, iron & ironing board, vacuum, hair dryer, bed linens, towels, toilet paper, hand soap, bath soap, shampoo, 6 beach chairs, cooler, 2 ocean kayaks (No direct water access).brbrMost of our guests choose not to bring a car. The property is central and conveniently located to Oak Bluffs and Vineyard Haven (1 mi), Edgartown (7 mi), and many beaches. Cabs usually arrive for pick up at property within 5 - 15 mins, bus stop nearby, direct bike path access. Beach and much more within walking distance.brbrPLEASE NOTE: Seasonal rates apply, and sometimes from late Jun to early Sep weekend only stays may not be accepted.brbrMed Flight helicopters pick up emergencies at the hospital from a field nearby. Typically they land and take off from a direction away from the property. Most guests don't consider the sound to be very loud. Otherwise, the property is very quiet and unaffected by the hospital which a good distance away.brbrFERRY TO MV: Can't get a ferry reservation for your car No worries. Contact Martha's Vineyard Steamship Authority during regular business hours and ask to be wait-listed. Usually they will contact you with reservations for your dates within 1 - 2 weeks or sooner.brbrGETTING AROUND: The property has direct access to MV bike path and Vineyard Transit Authority bus transportation to all Martha's Vineyard's towns. Cabs are readily available and reasonably priced to property from Oak Bluffs and Vineyard Haven harbor towns.brbrGUEST HOUSE: In addition, tucked away on the property is a charming 2 bedroom summer cottage. Sleeps 6, kitchen, living room with sleep sofa (full size), 1 full bedroom (double bed), 1 twin bedroom (2 single beds), shower, 1/2 bath, screen porch, outside porch, patio, large yard, 6-8 car parking area. Includes the same amenities as the house. Available June 15 - Sept 15, it can be rented separately or with the house.

Bed

Bath

Sleeps

$1340.4

/ Nightly

Private Vacation Home

Classic Vineyard Ocean, Harbor, Lake & Parkview Cottage w/AC

Oak Bluffs, Massachusetts, United States

The cottage is in restored original condition with many original features including hardwood floors, paned windows with original glass, cathedral ceilings, painted sink, shuttered interior doors and windows and clever built-ins and features 6 bedrooms (6 upstairs (one is a kids bedroom) via 2 stairways, one downstairs (parlor/bedroom with a pullout couch)), sleeps 10 max (linens/towels not provided), 8 zone split system heat and air conditioning plus room ceiling fans/box fans, 3 bathrooms; one upstairs with a claw foot tub over looking the harbor/ocean; two downstairs, one with handicap shower stall, one with an outside shower, living room with fireplace, kitchen with gas stove and antique glenwood cookstove, dining room with gas fireplace, sunroom, private outdoor vineyard with deck and seating area with grill, and large wrap around outdoor porch overlooking Washington Park, the town of Oak Bluffs, Sunset Lake (to the west) and the harbor/ocean to the south. Southeasterly exposure insures maximum sun.

Bed

Bath

Sleeps

$3248.61

/ Nightly

Private Vacation Home

Maison Calme/Peaceful Home

Oak Bluffs, Massachusetts, United States

This luxury enclave, complete with 4 bedrooms and 3.5 bathrooms, is located in a private community that is centrally located and comprised of upscale properties. The simply elegant home is a brand new construction that is nestled in a woodland setting with quaint views of a golden meadow and a beautiful pond. The stunning property connects to miles of walking/hiking trails and a bike path to Farm Neck Golf Club, in addition to 3 down island towns and beaches. With carefully crafted architecture, this house is full of character and integrity. The contemporary design offers upstairs and downstairs master bedroom suites as well as a first and second floor family-style living rooms complete with plasma screen TVs. At the top of the winding staircase is the hallway that wraps around to observe the open entry hall below. Two additional bedrooms are located upstairs with a bath and the kitchen has gorgeous cabinetry with high end appliances. There is wide oak flooring throughout and gleaming marble tile detail in the bathrooms. Other highlights include french doors that open to a large deck off of the living and dining room, complete with a table that sits 8 people, a lounge couch, and chairs. Additionally, there is a stone patio off of the first floor master bedroom, a stone fireplace anchors the living room, and a large and spacious backyard borders the back of the home. Every inch is a showcase of thoughtful design and beautiful custom finishes. Your new luxury getaway awaits you and your loved ones! More pictures will be coming soon as we are still working on the property!

Bed

Bath

Sleeps

$558.5

/ Nightly

Private Vacation Home

Quaint,,,Quiet..up island feel yet a short walk to town and harbor

Oak Bluffs, Massachusetts, United States

Your quintessential summer vacation starts here! The property has a combination of a strong rental history(read rental reviews) and a lot of repeat guests.br the house and guesthouse will make this rental a true summer getaway - all the feature comforts both inside and out! Comfortable beds and, luxury bath towels, furnishings, built-ins, central air, lighting, rugs, art work, and more! The spacious yard will encourage plenty of lounging under the shade trees, as well as an large area designated for outdoor games. The exterior deck is large enough to host the gas grill, dining table (with umbrella), seating for 6-8, as well as a private outdoor shower. All you need to clean up after a day at the beach, enjoy a few cocktails and get your BBQ going.br A short walk to town and harbor and just around the corner from the campground cottages, yet set on a very quiet street with an up-island feel !! Wifi and A/CbrbrRental Sleeps 6-8 MaxbrMain house : 2 bedrooms on 2nd floor of main house.(1) Bedroom w/ Queen Bed br(1) Bedroom w/ Queen Bed, and (1) built-in futon that can easily double as a child’s bed.brAu paired suite or Private Guest Cottage (has own bathroom): (1) Queen Bed and (1) pull out single bed.. also air mattress for extra sleeping space.br Please bring sheets and pillow cases. I will provide luxury bath towels and facecloths...or let me know ell in advance if sheets and pillow cases need to be provided. My rental period is Saturday to saturday during summer months.br brbr

Bed

Bath

Sleeps

$781.9

/ Nightly

Private Vacation Home

Cozy, exceptional view, quiet, high speed WIFI, close to all island attractions

Oak Bluffs, Massachusetts, United States

This comfortable house provides up and downstairs amenities. The master bedroom with bath is on the ground floor; the other full bedroom and sleeping areas are upstairs. Thel loft with great views that can be used for additional sleeping space or relaxation. TV and Wireless Internet connectivity. Large deck oversees the landscaped yard, pond and ocean. Within walking distance of private beach. Outside shower and grill.brbrThis home is located in a quiet rural area surrounded by pine trees and coastal landscaping, with a view of Sengekontacket Pond and Nantucket Sound. A substantial deck provides an amazing view of the area.brbrWithin a mile of the house, one will find the bustling town of Oak Bluffs with shopping, restaurants, movie theaters, the Flying Horses Carousel and other entertainment. Restaurants are as varied as the town and sea food is abundantly available. Those interested in the arts can visit the Featherstone Center for the Arts or Andrew Moore studio.brbrFarm Neck Golf Course is adjacent to Waterview Farm and State Beach is within a 5 mile drive or a kayak ride across the pond. Felix Neck Wildlife Sanctuary is in the next cove providing abundant nature trails for hiking. brbrOutdoor activities include bicycling and hiking. Extensive beach and water activities offer kayaking, jet skis, sailing, boat charters and fishing. The house offers each access to these amenities.brbrLocated within easy driving distance of other island towns. Each town has it's own unique personality and attractions. Enjoy the shopping, site seeing and different restaurants of each area. Drive to Aquinnah to see spectacular view of the ocean and the many lighthouses.brbrOne of the most relaxing vacations with many opportunities for activities or just enjoying the scenery and people.

Bed

Bath

Sleeps

$721.58

/ Nightly

Private Vacation Home

Beautiful 3 bedroom 2 bath Home / Close to Town & Beach

Oak Bluffs, Massachusetts, United States

Beautiful and spacious 3 bedroom and 2 bathroom in Oak Bluffs, Martha's Vineyard. Sunny, open and airy Cape style home. Sleeps 6 people.brComfortably furnished, has air conditioning, Hi-Speed internet, cable TVs, washer, dryer and parking. Large, private back yard with deck and grill. Convenient location - short walking distance to town, playground, Gingerbread Houses, and short bike ride or drive to beach, golf course, harbor, and great fishing spots. Perfect for family vacations or romantic getaways.brbrPlease feel free to bring your own linens from home or rent for conveniency from a local service where all linens are properly laundered and ready for use upon arrival. Sheeting and pillowcases needed for: 2 Queen Bed and 2 twin beds There are bathroom rugs/mats and kitchen dish towels in the house. Each bed has a light quilt, extra blanket, mattress protector and pillow(s) provided.

3

Bed

2

Bath

6

Sleeps

$1074.06

/ Nightly

Private Vacation Home

Oak Bluffs Home Walk to Town, Beaches & Harbor

Oak Bluffs, Massachusetts, United States

give me a less than 80 character headline for this description:brbrWelcome to 22 Wing Road in Oak Bluffs, a newly renovated home that offers the perfect combination of comfort, convenience, and location for your Martha’s Vineyard vacation.brbrSituated just minutes from downtown Oak Bluffs, you can easily walk to the harbor, beaches, restaurants, shops, and ferry while still enjoying a quiet residential setting. The location also provides easy access to back roads, allowing you to explore the island while avoiding summer traffic. Farm Neck Golf Club, several beaches, and bike paths are all just a short drive away.brbrThe home’s layout is ideal for families or groups of friends traveling together.brbrThe first floor features a bright and welcoming living area with a large TV and high-quality sound system, perfect for relaxing after a day at the beach. The fully equipped kitchen opens into the main living space, creating a comfortable area to gather and unwind. Also on this floor is a bedroom with a queen bed and a full bathroom.brbrUpstairs on the second floor, you’ll find two additional bedrooms. One bedroom includes a queen bed, while the second bedroom is great for kids or larger groups with two twin-over-full bunk beds. There is also an additional twin bunk bed in the hallway, providing flexible sleeping arrangements for larger families or groups. A second full bathroom is located on this level.brbrWith its newly renovated interior, excellent location, and comfortable layout, 22 Wing Road makes an ideal home base for enjoying everything Martha’s Vineyard has to offer — from beach days and biking to golf at Farm Neck and evenings exploring the vibrant downtown Oak Bluffs area.

Bed

Bath

Sleeps

$1101.04

/ Nightly

Private Vacation Home

Spacious Victorian, 5 minute walk to beach, town, and ferry in Oak Bluffs

Oak Bluffs, Massachusetts, United States

Welcome to the Oak Bluffs Victorian Cottage that dreams are made of! Newly renovated (summer 2017), the rambling Main House has five bedrooms, two of which are Master Suites with private baths. Two additional full baths and one half bath provide comfort for the guest rooms, and there is a new outdoor shower for post-beach bathing. A parlor, living room, dining room - each with a ceiling fan - and remodeled kitchen are all on the first floor, along with a full bath off the kitchen plus a bedroom with 1 Queen bed and en suite bath. Additionally, the DR, kitchen, and downstairs BR each have their own mini-split AC units. brbrThe four additional bedrooms are upstairs: 1 Q (ensuite bath) with balcony, 1 Q w/ sink and a water closet across the hall, 1Q, and a bunk room with a full-over-full bunk bed, a twin bed, and a window unit AC. br brA full bath with clawfoot tub is next to the bunk room and the kids game room / reading room, which is stocked with the classics (Clue, Monopoly, Sorry!, Uno and more); this is also where the TV w/ cable is located. Plenty of good summer reads are in the the bookcases throughout the house, and there is high-speed WiFi. brbrThe huge front porch has dining for 12, while 8 can be accommodated in the DR and 4 can fit at the small table in the kitchen with room for two at the kitchen island. The kitchen has everything you need to cook for a crowd, and there is a large Weber gas grill outside. The side porch off the kitchen with two rocking chairs is a nice place to enjoy a cup of coffee in the mornings, or retreat to the front porch nook that seats 4 and has a coffee table and ceiling fan. brbrThis Victorian is very conveniently located, only a 5 minute walk to Inkwell Beach, Circuit Ave. (restaurants, grocery store, arcade, shops, carousel, etc.), the Martha's Vineyard Camp Meeting Association and Tabernacle (worship services, walking tours, outdoor yoga, community sing, speaker series, concert series, and more!), and Ocean Park (concerts, fireworks, and a great place for the kids to fly kites!). A grassy, shaded boulevard is immediately across the street and is a great place for a game of catch, while Niantic park with its basketball court, playground, tennis & pickleball courts is less than a 10 minute walk away. If you bring a car(s) over, there is tandem parking for two, plus street parking as available, though you can feel free to leave the cars at home. br With everything close by and the OB ferry terminal a 10 minute walk away, you're in the middle of it all while being on a quiet enough street that you can get a good night's sleep. Buses service is good, and rental bikes are plentiful, so you easily can explore other towns and beaches on the island. Come see why we love it here!

5

Bed

4

Bath

13

Sleeps

$634.46

/ Nightly

Private Vacation Home

Martha’s Vineyard Cottage

Oak Bluffs, Massachusetts, United States

This memorable house is the perfect home base for your trip to Oak Bluffs. Very centrally located between the 3 down island towns, shops, and public beaches. Guests will enjoy three cozy bedrooms featuring a king bed, queen bed, twin bed, and full bed, offering plenty of space for everyone. Two bathrooms make getting ready a breeze, and the lovely indoor climate keeps things comfortable year-round. Whether you’re relaxing after a day of exploring or gathering for a meal, this quaint house provides a wonderful setting to unwind. We look forward to welcoming you to our place.

Bed

Bath

Sleeps

$692.72

/ Nightly

Private Vacation Home

Oak Bluffs - Quiet neighborhood

Oak Bluffs, Massachusetts, United States

Less than a mile from downtown, harbor and beach. Located in a quiet neighborhood, guests are sure to enjoy a memorable vacation in this fully furnished, 4 bedroom/1 bath house. Updated kitchen and bath, the space is comfortable for sleeping up to 8 people. The living room is furnished with a sectional couch and a 50 television for your enjoyment. The kitchen is perfect for dining as it is equipped with a stove, microwave, dishwasher and a full refrigerator. The large deck is great for taking in the sun or barbecuing on the gas grill. There is also a furnished gazebo with mosquito netting. The property is just minutes away from all of best attractions, and guests are sure to enjoy having the whole home to themselves.

Bed

Bath

Sleeps

$2024.57

/ Nightly

Private Vacation Home

The Island Collection MV: Enjoy This 1850s Victorian Home With Ocean Views!

Oak Bluffs, Massachusetts, United States

Enjoy a relaxing ferry ride to Oak Bluffs and its picturesque surroundings. Once your ferry ride ends, you’re steps away from home! This newly renovated, elegant, enchanting, and historical bright yellow Victorian home was built in the 1850s. Speaking of ocean views….enjoy the benefits of having an ocean view right in your front yard! Located on Ocean Avenue you can see the entire ocean from this lovely home, which has 7 bedrooms, 4 full bathrooms and comfortably sleeps 14 people. There is one parking space available on the street, a gas grill on the back patio, and an outdoor shower for your convenience.brbrAs you enter the home, you will be amazed at the beauty of the fireplace. On the first floor, enjoy an ocean view room with a fireplace. There is also one large bedroom with one queen bed and one twin bed. On the second floor, enjoy a beautiful and cozy ocean view room with a telescope. There are also five bedrooms with a queen bed in each; and one bedroom with two twin beds. There are four full bathrooms located throughout the home for your convenience.brbrThis beautiful home has all new appointments such as: a new kitchen, new granite counter tops, new showers, new mattresses for all beds, all new furniture with an entirely furnished home, new air conditioners, and the home is freshly painted.brbrIndulge in a wonderful meal with your family in the formal blue and white dining room, which the owners lovingly refer to as “The Great Wall of China!” Relax and enjoy the spacious family room, living room, and formal dining room which all comfortably seat 14 people.brbrConveniently located steps away from the ferry, this home is only 100 feet away from the beach. As the home is located in town, you are close to quaint downtown shopping, night life, restaurants, churches, parks, hiking and bike paths and trails, deep sea fishing, car, bike and motor cycle rentals. Enjoy a tour around the island by way of public transportation (the bus stop), or taxi.brbrFrom your front porch, look at the beautiful ocean view, which includes a park and gazebo where you will see people getting married and feel their job of beginning their lives as one. Listen to various genres of music in the park performed by local and national bands. Watch fireworks from the lower and upper decks of the home. brbrWitness the uplifting joy of experiencing people fly kites or indulge in this activity for your own pleasure.brbrThis house is featured on many postcards, calendars, and other media. It is very well known throughout Oak Bluffs! Even the new 2015 Martha's Vineyard calendar features this premier home inside for the month of October.br brAs you can see, there is no need for a car…you’re in Oak Bluffs, where the action is only a short walk away! After a long day at the beach, shopping, dining, and fun, you’re steps away from home! We look forward to seeing you! brbrWe adhere to the customs for home rentals on the Vineyard, which do not include linens (sheets, pillowcases, towels, or beach towels) as a part of the rental experience. Please arrange to bring your own linens or visit www.marthaslinenrental.com to place an order for your linen rental. br1st Fl Queen Master and Twin, 2nd Fl 5 Queen, 2nd Fl 2 Twin

7

Bed

4

Bath

14

Sleeps

$959.56

/ Nightly

Private Vacation Home

New to the rental market! Air conditioned family home, 1 mile from Circuit Ave

Oak Bluffs, Massachusetts, United States

New rental! Get away from it all in this Oak Bluffs secluded family friendly home offering 4 bedrooms, 2 full bathrooms, 1 outdoor shower, & more. Relax in our ranch style home just under 1 mile from Circuit Ave. Located half way between downtown OB and Vineyard Haven - this is the perfect location for a relaxing vacation. Enjoy a family dinner in the large eat-in kitchen that opens to a back deck and stone patio or stay in for a family movie night - there's adequate space for both!brbrPlease note: 7 night minimum stay during peak season in July and August.

4

Bed

10

Sleeps

Exceptional(9)

$884.3

/ Nightly

Private Vacation Home

The Legacy House: Walk to Inkwell Beach + Historic Charm, Modern Comfort

Oak Bluffs, Massachusetts, United States

Step into the timeless charm of Oak Bluffs while enjoying the comforts of a thoughtfully renovated home. The Legacy House blends 250 years of history with modern upgrades—creating a one-of-a-kind stay just 2 blocks from Inkwell Beach and a short stroll to everything you love about Oak Bluffs.brbrWhether you're planning a multi-family summer getaway or a peaceful fall retreat, this home offers the space, location, and character that make Martha’s Vineyard unforgettable.brbrWhy Guests Love The Legacy Housebr- Unbeatable Location – Walk to Inkwell Beach, Circuit Avenue, Ocean Park, and the ferrybr- Historic + Renovated – 250-year-old home with a brand-new kitchen and updated bathroomsbr- Perfect for Groups – Comfortably designed for 2 families or group gatheringsbr- Outdoor Living – Wrap-around porch, large rear deck, and outdoor showerbrPeaceful Setting – Quiet, charming neighborhood just steps from the actionbrNo Hidden Fees – Transparent pricing, alwaysbrbrThe SpacebrThis spacious home is filled with warmth, personality, and room to gather.brbr- Large front sitting/family room for relaxing togetherbr- Full dining room for shared meals and memoriesbr- 5 thoughtfully arranged bedrooms across two levelsbr- 2 full bathrooms (one on each floor)br- Ample off-street private parkingbrbrStart your mornings with a sunrise walk to the water—or join the iconic “polar bears” for an early swim. Spend your afternoons biking, shopping, or relaxing on the porch with a drink in hand.brbrSleeping ArrangementsbrbrDesigned for flexibility and comfort:br- Bedroom 1 (Upstairs): King bed, spacious, bright, flat-screen TVbr- Bedroom 2 (Upstairs): Queen bed + private balconybr- Bedroom 3 (Upstairs): Double + twin bunk with trundle (ideal for kids)br- Bedroom 4 (Upstairs): Twin with trundle (sleeps 2, great for kids/teens)br- Bedroom 5 (Downstairs): Queen bed, large room, ground-level access, TVbrbrOutdoor + Local Highlightsbr- 2 blocks to tennis, pickleball, and basketball courtsbr- Easy walk to beaches, shops, dining, and entertainmentbr- Classic Oak Bluffs neighborhood full of history and charmbrbrPlease Read Before Booking (Important Details)brWe want your stay to be seamless, so here are a few important notes:br- 7-night minimum during peak seasonbr- This is a historic 250-year-old home—full of charm, but not a hotel-style propertybr- Linens & towels are not included by default but we will order them for youbr- We arrange rental and delivered prior to arrival based on your guest countbr- Accuracy in your reservation is important to ensure proper setupbrbrNo pets allowedbrbrA Different Kind of StaybrThe Legacy House is for those who appreciate character, history, and togetherness over a cookie-cutter experience. If you're looking for a place where mornings start on the porch, days are spent walking to the beach, and evenings bring everyone back together—you’ll feel right at home here.

Bed

Bath

Sleeps

$1126.37

/ Nightly

Private Vacation Home

Air conditioned Oak Bluffs WATERVIEW Victorian. steps from beach. BIG porch.

Oak Bluffs, Massachusetts, United States

*** CONTACT HOST TO CONFIRM DATES BEFORE BOOKING****brbr*** CONTACT HOST FOR EARLY BIRD SPECIAL AND OFF-SEASON RATES***brbr***2-4 DAY MINIMUM DURING OFF-SEASON***brbrClassic Victorian STEPS from the beach and a few short blocks to Circuit Avenue, shopping, ferries, Oak Bluffs Harbor, and town parks! brbrThis air-conditioned (mini-splits) home features a wrap-around porch with water view, an enclosed three-season sleeping porch, a welcoming living room, dining room, modern kitchen with cozy breakfast nook, laundry room, upgraded bathrooms, five (5) bedrooms, and an outside shower. There is also ample off-street parking in the driveway.brbr• Cottage 1800 sq. ftbr• Sleeps: 13 (11 adults and 2 children)br• Bedrooms: 5br• Seasonal Sleeping Porchbr• Bed & Bath Linen included (beach included - reservations made after 5.1.26)brbrBedroom #1 - FullbrBedroom #2 - Queen & Twin w/private balcony brBedroom #3 - Queen w/private balconybrBedroom #4 - FullbrBedroom #5 - Twin (2) (*Twin air mattress and Twin bed converter in closet)br#6 - Seasonal sleeping porch w/bunk beds (sleeps 2)br• Bathrooms: 2br• Outdoor showerbr• Smart TV/Cable br• Washer & Dryer br• Mini Splits (AC-Heating) unitsbrbr*2 BEDROOM-PRIVATE BALCONIES, 1 with water-viewbrbr*400 sq. ft wrap-around front porch with water view and comfortable seating for 11+ (rocking chairs, dining table w/ seating for 4, & 2 benches)br*Outdoor back patio w/ propane grillbr*Spacious outdoor shower w/dressing room, adjacent to back patiobr*Off-street parking for 2 carsbr*Side yardbr*Updated and well-stocked kitchen with charming built-in “breakfast nook” seating br*Dining room table that can comfortably seat 11+br*10’ high ceilings on the 1st floor give a sense of airy spaciousness and help keep the house coolbr*Ceiling fan in dining room and 2 bedrooms, personal/portable fans in all other roomsbr*Upstairs back bedroom with private staircase to kitchenbr*The house is winterized, with insulated windows, a furnace & A/C-Heat mini splitsbrbr*Charming Victorian details: an ornate living room mantle, hall columns with built-in bookshelves, a front interior staircase with carved “gingerbread” balusters, a built-in dining room china cabinet, kitchen, an arched kitchen breakfast nook, a bay-window seat and a very rare light (white oak) and dark (walnut) striped hardwood dining room floorbrbr*Tidiness is a top priority, and our outstanding cleaning crew uses an organic line of cleaning products to ensure that the house is sanitized and sparkling for your arrival.brbr*Our wonderful caretaker, Wayne, provides our guests with a customized and thoughtful trash and recycling service. No dragging the trash bins to the curb for pick-up, or being woken up at the crack of dawn by a noisy trash truck!brbrIn order to keep our prices competitive, we will only supply enough personal supplies to begin your stay. Please prepare to bring the extras such as tissue, paper towels, cleaning supplies to insure optimal comfort when you arrive.brbr*** 7 DAY MINIMUM DURING PEAK-SEASON***brbr***2-4 DAY MINIMUM DURING OFF-SEASON***brbr***CONTACT HOST TO INQUIRE ABOUT OFF-SEASON RATES***

6

Bed

2

Bath

13

Sleeps

$1477.77

/ Nightly

Private Vacation Home

OAK BLUFFS - INKWELL WATERVIEW Renovated Cottage with A/C, modern decor

Oak Bluffs, Massachusetts, United States

Beautifully renovated in-town Victorian Cottage. 4 bedrooms and 2.5 baths. 2 of the 4 bedrooms with a partial water view. Fully air-conditioned with heat and a has fireplace and a lovely waterview from the rockers on the front porch. brbrBEDROOMS:br#1 - Queen bed (1st Floor)br#2 - Queen sofa pullout (1st Floor)br#3 - Queen bed (2nd Floor)br#4 - Queen bed (2nd Floor)br#5 - Double bunk bed (2nd Floor)brbrBATHROOMS:br#1 - Glass walk-in shower (1st Floor)br#2 - Half bath (1st Floor)br#3 - Tub & shower (2nd Floor)brbrA second kitchen with a refrigerator, a coffee maker, 2 gas burners, an air fryer, and a private entrance. Private outdoor shower off of the private deck with a gas grill. Linens and towels are rented depending from a 3rd party linen rental companybrbrYou will enjoy this fabulous in-town location. This home is less than a 1/2 block to Inkwell Beach. Less than a 5 minute walk to Circuit Avenue shops and restaurants. Walk to the Steamship Authority dock, Historic Ocean Park, the Gingerbread Cottages, and the Oak Bluffs Harbor. brbrA perfect family vacation home to create your Martha's Vineyard memories!

Bed

Bath

Sleeps

$716.75

/ Nightly

Private Vacation Home

Spacious 4 BR Home, Steps to Lagoon, Minutes to Downtown Oak Bluffs and Beaches!

Oak Bluffs, Massachusetts, United States

Spacious two-level four-bedroom house within steps to lagoon located in Oak Bluffs and within minutes (2 Miles) to Downtown Oak Bluffs and beaches! Features both a separate living room and family room, two full bathrooms, a fully-equipped kitchen, and as a bonus has a screened-in porch to enjoy your morning coffee! This lovely home also has a large front and back yard, as well as a separate driveway. As another bonus, it comes with two cars for additional rental! Great for families. Sorry, no pets allowed. We have had many satisfied, repeat visitors!

Bed

Bath

Sleeps

$590.13

/ Nightly

Private Vacation Home

Lovely vacation home within walking distance to Oak Bluffs and the beach

Oak Bluffs, Massachusetts, United States

Welcome to your summer vacation home! This is a 3 bedroom 2 1/2 bath home located less than a mile from downtown Oak Bluffs. Famous for its ice cream parlors, back door donuts, Flying Horses carousel, variety of cuisines, night life, and much more. brbrThe open floor plan with an attached 3 season porch is perfect for entertaining, but cozy enough to create the perfect ambiance. The master suite is on the 1st floor and the living room has a beautiful teakwood spiral staircase to the 2nd floor. The second floor has 2 bedrooms, full bath, office area and a TV room. The house sleeps 6.

3

Bed

2

Bath

6

Sleeps

Vacation Home Rentals By Owner In Oak Bluffs, MA

$595.73

$2034.86

$617.33

$636.69

$1340.4

$3248.61

$558.5

$781.9

$721.58

$1074.06

$1101.04

$634.46

$692.72

$2024.57

$959.56

$884.3

$1126.37

$1477.77

$716.75

$590.13

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