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Vacation Rentals In Oak Bluffs, MA

Showing 20 Of 284 Vacation Rentals

We Have 284 Vacation Rental Offers Available In Oak Bluffs. Average Price Per Night Is $564.34. Find Your Vacation Home Today.

  • Property-1 Image 1
    Private Vacation Home
    Bright townhome with deck, grill, W/D & tennis court - quiet location
    Oak Bluffs, Massachusetts, United States

    Quail Run RetreatbrbrOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'brbrThe best of Martha’s Vineyard is just outside your door when you choose this lovely, two-bedroom townhome, tucked into a quiet area between Oak Bluffs and Edgartown, complete with walking trails, tennis/pickleball courts, a freshwater pond, and dock access to Sengekontacket Pond. Beaches, nature reserves, ferries, gardens, farm stands, and local shops and restaurants are all an easy drive or bike ride away. brbrAt home, start the day with coffee on your private deck, enjoying the quiet. Step inside to the full, well-equipped kitchen for some breakfast prep. Dine together at the table for four, or step back out through the French doors and dine alfresco on the deck. Pop the dishes in the dishwasher and head out to explore Martha’s Vineyard Performing Arts Center, just over a mile away. When you return, relax on the couch while you stream the latest release, grab a board game or a book, or use the free WiFi to upload the day’s pics. End the night as you began - back out on the deck, toasting your good luck at booking such a sweet escape.brbrTHINGS TO KNOWbrStreaming services are available with guest accounts.brA twin bed in the loft offers extra sleeping space.brbrParking notes: There is free parking available for 1 vehicles.brThis rental is located on floor 2.brbrbrbrDamage waiver: The total cost of your reservation for this Property includes a nightly damage waiver fee, plus tax if applicable (the “Damage Waiver”). (A discount may be applied for stays of 28 nights or longer, if permitted.) The Damage Waiver covers you for up to $3,000 of accidental damage to the Property or its contents (such as furniture, fixtures, and appliances) as long as you report the incident to the host prior to checking out. The Damage Waiver fee eliminates the need for a traditional security deposit.brMore information can be downloaded from the "Rental Agreement" on the checkout page.brbrDue to local laws or HOA requirements, guests must be at least 21 years of age to book. Guests under 21 must be accompanied by a parent or legal guardian for the duration of the reservation.brbrbrState/province tax number: C0380622210 Read More

    2 Bed
    2 Baths
    Sleeps 5
    $754 / Nightly
  • Property-2 Image 1
    Exceptional
    (20)
    Private Vacation Home
    Nice house, great location - Oak Bluffs!
    Oak Bluffs, Massachusetts, United States

    Bright and airy house in a quiet neighborhood near the library. The location is tucked away yet an easy walk to shops, restaurants, galleries, harbor, and beaches. The house features four spacious bedrooms. Each of the two bedrooms on the first floor has a private deck, perfect for morning coffee or an evening nightcap. The second floor has two enormous bedrooms, each an en-suite with tons of closet space. All but one room in the house has a mini-split for air conditioning or heat.brbr*** No Service Animals Allowed. The property is strictly an animal free zone because the owner has severe allergies.***brbrPlease note that bed linens and bath towels are not included in the standard rental fee. You are welcome to bring your own or use one of the linen rental services on the island. We realize the two main options for linen services are not great – one does not offer quality fitted sheets, and the other is quite expensive. We also understand that some wish to travel light without the considerable bulk of bed linens, bath towels, washcloths, and beach towels. So as a solution, we can provide these items for an extra $200, which is much lower cost for quality linens. We offer this only as a convenience, so feel free to bring your own items (no cost) or use one of the linen services. brbrThe house features an open concept kitchen/dining/living room area with casual seating/dining space for eight. Enjoy meals in the functional kitchen with stainless steel appliances, quartz countertops, and a large island. In addition to the standard coffee maker and toaster, we provide a Kitchen Aid mixer, waffle iron, stovetop espresso maker, griddle, pressure cooker, electric tea kettle, and a food processor. We even have a Vitamix blender, which is perfect for making frozen drinks. Yes, we have a high chair for the little one. brbrEnjoy the spacious yard and wonderful garden. The house has an outdoor dining area, with seating for ten and a separate patio area for relaxing. When it's time to get your GRILL on, fire up our Weber grill with the sear station. Oh, by the way, YOU WILL fall in love with the outdoor cedar shower. brbrWe have your entertainment covered too, see below.br br*** Outdoor games include volleyball, badminton, jumble Kenga, Corn hole, dodge ball, and frisbees. brbr**** For the beach, we have sand toys, four beach chairs, a big cooler and medium-size cooler, and two boogie boards. brbr*** Indoor games include chess, checkers, a poker chip set, dominoes, kid games, and of course, UNO. brbrWe provide high-speed internet and get great reception throughout the house. Every bedroom has a flat-screen TV, an Apple TV device, and an echo Dot smart speaker. Free access to Netflix, HBO max, and Apple Music is included.brbrBedroom descriptionsbrbrBlue Room: This is the smaller of the 1st-floor bedrooms. The room features a large closet and a small private deck. Furnishings include a queen bed, four-drawer dresser, and a nightstand. The room has a TV and an Echo Dot smart speaker.brbrGrey room: This is the larger of the 1st-floor bedrooms. The room features a large closet and private deck with a bistro set. Furnishings include a king-size bed, four-drawer dresser, and a nightstand. The room has a TV and an Echo Dot smart speaker.brbrCaptain room: This is a large bedroom on the 2nd floor that features a private bathroom, large closet, and an office nook. Furnishings include two full-size beds, a four-drawer dresser, and two nightstands. The room has a TV and an Echo Dot smart speaker.brbrMaster bedroom: This is an enormous bedroom that features a private bathroom, reading nook, and walk-in closet. Furnishings include a king-size bed, a queen-size, pull out "cabinet" bed, four-drawer dresser, and two nightstands. The room has a TV and an Echo Dot smart speaker. Read More

    4 Bed
    3 Baths
    Sleeps 8
    $700 / Nightly
  • Property-3 Image 1
    Very Good
    (4)
    Private Vacation Home
    Traditional Martha's Vineyard Home w/ Porch & Yard
    Oak Bluffs, Massachusetts, United States

    This exquisite, shingled Colonial house with an expansive wraparound porch is synonymous with Martha's Vineyard architectural style. The 2,500-square-foot vacation rental home features 4 bedrooms, 3 bathrooms, accommodations for 9 guests, and a beautiful, lush yard space. If you're seeking a restful getaway, this home is the perfect spot for you to enjoy the rustic charms of this infamous 100-square-mile New England island. Walk to the ferry, beach, harbor, endless town attractions, and more!brbr-- THE PROPERTY --brbrWalking Distance to Beach, Harbor & Ferry | 2,500 Sq Ft | Free WiFibrbrDesigned with families in mind and filled with New England charm, this colorful Martha’s Vineyard home is stocked with at-home essentials and an ideal location ensuring a seamless vacation experience full of lasting memories!brbrBedroom 1: King Bed | Bedroom 2: Queen Bed | Bedroom 3: Full Bed | Bedroom 4: 2 Queen BedsbrbrOUTDOOR SPACE: Screened porch, deck, outdoor dining, gas grill, covered patio, hammock, outdoor showerbrINDOOR LIVING: Flat-screen cable TV, DVD player, board games, books, dining tablebrKITCHEN: Fully equipped w/ cooking basics, breakfast bar, stainless steel appliances, dishware/flatware, Crockpot, drip coffee maker, kettle, toaster oven, toasterbrGENERAL: Washer/dryer, linens/towels, central air conditioning/heating, beach towelsbrFAQ: Stairs required, quiet hours (11:00 PM - 8:00 AM)brPARKING: Driveway (3-4 vehicles)brbr-- THE LOCATION --brbrMAIN ATTRACTIONS: Gingerbread Houses (0.4 miles), Ryan Family Amusements (0.6 miles), Flying Horses Carousel (0.7 miles), Ocean Park (0.7 miles), Jaws Bridge (3.7 miles)brSAND & SUN: Oak Bluffs Town Beach (0.7 miles), Inkwell Beach (1.0 miles), Eastville Point Beach (1.4 miles), State Beach (3.7 miles), South Beach (9.3 miles)brSIGHTSEEING: Main Street Vineyard Haven (3.1 miles), Downtown Edgartown (6.5 miles), Menemsha (14.2 miles), Gayhead Lighthouse (20.3 miles)brLOCAL EVENTS: Oak Bluffs Open Market (0.9 miles), West Tisbury Farmers Market (9.0 miles), Chilmark Flea Market (10.8 miles)brFERRY TERMINALS: Steamship Authority Oak Bluffs (0.8 miles), Steamship Authority Vineyard Haven (2.5 miles)brAIRPORTS: Martha's Vineyard Airport (6.7 miles), Logan International Airport (86.7 miles)brbr-- REST EASY WITH US --brbrEvolve makes it easy to find and book properties you’ll never want to leave. You can relax knowing that our properties will always be ready for you and that we’ll answer the phone 24/7. Even better, if anything is off about your stay, we’ll make it right. You can count on our homes and our people to make you feel welcome--because we know what vacation means to you.brbr-- POLICIES --brbr- No smokingbr- No pets allowedbr- No events, parties, or large gatheringsbr- Must be at least 22 years old to bookbr- Additional fees and taxes may applybr- Photo ID may be required upon check-inbr- NOTE: Please observe quiet hours from 11:00 PM to 8:00 AMbr- NOTE: The property requires stairs and may be difficult for guests with limited mobilitybr- Massachusetts Tax ID: C0119712210 Read More

    4 Bed
    3 Baths
    Sleeps 9
    $536 / Nightly
  • Property-4 Image 1
    Exceptional
    (4)
    Cottage
    Sunny Oak Bluffs cottage minutes from beach
    Oak Bluffs, Massachusetts, United States

    Hello! This is a bright and airy colonial-style cottage with lots of comfortable spots to spend time together, or spread out and relax. Outside there is a large grassy yard, a flagstone courtyard just off the kitchen for morning coffee or happy hour, and a deck on the opposite side of the house with a large dining table and umbrella for family meals. brbrThe sunny galley kitchen is open on both sides to the patio and living/dining area and includes a four burner range, integrated fridge, combination microwave/convection oven/air fryer (Breville), Nespresso coffee machine, drip coffee maker, toaster, electric kettle, blender/food processor, stainless pots and pans set, baking pans, cooking utensils, dining service and flatware for 8, glasses, mugs, and serving dishes. Weber gas grill (Spirit II) just outside on the patio!brbrThe main living/dining area is lined with windows and gets pretty sunlight all day long. The dining area includes a round 4-top table and chairs, credenza, and Kliptsch wireless speaker. Two comfortable couches facing each other create a cozy conversation area in the adjacent space. A bathroom with shower is also on this floor.br brThe lower level is a game/ media room with a large dining table for overflow seating or board games, another large couch and ottoman, and a 55 inch OLED flatscreen smarttv with streaming for movie nights or rainy days. A full bathroom with tub and shower, as well as a washer and dryer for your use are also located on this floor.brbrTwo bedrooms, one with two full beds and the other with one double, are located on the top floor off a small landing- each have large dressers, lamps, skylights, cathedral ceilings and white wood panelling.brbrOur "nap cottage" is located a few steps from the main house off the flagstone patio- this is a stand-alone windowed cottage bedroom with a dutch door (with lock), ac, a double bed, side tables, lamp and small dresser. This always seems to be the most requested bedroom among our family and friends- it is perfect for a couple sharing the house with a family, older children who want to sleep in their own "house" or anyone looking for a little extra privacy.brbrWe also have a separate windowed office studio with wifi for remote work, including a desk, chair, ac, lighting and bookcase. brbrFinally, a spacious hardwood outdoor heated shower with shelves and towel hooks is located off the patio- rinse off the beach sand under the trees!brbrOur cottage is located in a serene neighborhood close to the Oak Bluffs lagoon and is a super easy 5 minute drive to downtown Oak Bluffs, Inkwell beach, the original Black Dog Tavern, and everything else Oak Bluffs and Vineyard Haven have to offer. Neighborhood access to the lagoon is at the end of the street via a wood staircase, and access to the excellent MV bike path is located about 200 feet away on County Road. brbrAll bed linens, bath and beach towels are included, as well as use of a beach cabana (coolcabana brand), oversized sand-free beach blanket, cooler, kids beach toys, badminton net, board games, gas grill and laundry! Professional cleaning before every check in. Kitchen is stocked with coffee, tea, salt, pepper, basic dry spices, olive oil and balsamic vinegar.brbrThanks for reading and let us know any questions! Read More

    3 Bed
    3 Baths
    Sleeps 8
    $399 / Nightly
  • Property-5 Image 1
    Exceptional
    (13)
    Private Vacation Home
    Brand New Oak Bluffs Home, Steps from the Lagoon
    Oak Bluffs, Massachusetts, United States

    Come enjoy this beautifully designed, brand new home. With 3 bedrooms and 3 full bathrooms you will have all the space you need. An outdoor patio with gas grill is the perfect spot to relax after a day at the beach. Just a few steps away is the lagoon where you can paddle board, kayak, dig clams, or just take in the amazing sunsets! Read More

    3 Bed
    4 Baths
    Sleeps 6
    $526 / Nightly
  • Property-6 Image 1
    Wonderful
    (120)
    Cottage
    Make Lasting Memories In This Adorable Vineyard Cottage!
    Oak Bluffs, Massachusetts, United States

    This quaint cottage, nestled in a quiet neighborhood of Oak Bluffs, is perfect for a romantic getaway, a special place to bring your favorite friends, or a wonderful spot to have a family vacation. Some guests also choose to have a solo retreat to read, write, explore, and re-center. Cottage visitors comment on the welcoming feeling they experience as soon as they walk in the door, and the sweet simplicity of this cozy abode.brbrThe Cottage sleeps 4 easily. There is a queen-sized futon on the ground level, and a king-sized sleeping loft. The living area has a comfy cozy futon, SmartTV, an activity/game drawer, and FREE WIFI. The kitchen contains a full-sized stove, microwave, fridge/freezer, and a Keurig machine - so bring your favorite k-cups! There is a washer/dryer for your use as well. There are plenty of towels and linens, so no need to bring your own. brbrAfter a full day of exploring, bike riding, shopping, or finding creative inspiration, enjoy a nice dinner or a bottle of wine on the attached deck. It's a perfect place for star gazing too! brbrThere’s plenty to do within walking distance, and a taxi or public transportation can get you to the other Vineyard towns, so a car is not necessary (but it’s nice to have). The Cottage is a mile from Oak Bluffs Center and the town beaches, so a 15 minute walk or a 5 minute bike ride will bring you to either.brbrCome make this lovely Cottage the heart of your own Vineyard experience! Read More

    1 Baths
    Sleeps 4
    $191 / Nightly
  • Property-7 Image 1
    Exceptional
    (2)
    Private Vacation Home
    Fully Renovated & Spacious home walking distance to downtown Oak Bluffs/Beaches
    Oak Bluffs, Massachusetts, United States

    Newly renovated three-level home with 3 bedrooms 2 bathrooms within walking distance to the heart of Downtown Oak Bluffs and beaches. This location allows you to be at the center of activity from Fourth of July fireworks to Illumination but a quick escape into the quiet neighborhood of The Highlands. Walking distance from Oak Bluffs Town Beach (Inkwell) and ferry station. A bright spacious fully renovated and well-appointed must-see home that you won’t want to leave. Comfortable living spaces for 6 people to relax and socialize. Open kitchen with new appliances and all the cooking tools necessary to whip up a pot of chowda or to have guests over to enjoy a lobster bake. Beautiful rooftop deck with a view of the Harbor and lake or a great place to listen to the morning chirping of birds. Two Bedrooms on the second floor- one with a comfortable Queen bed and the other with 2 twin beds. Master bedroom with bathroom with a peak of the Harbor. brBackyard with picnic tables and a grill for those warm summer family cookouts. Shared parking.brbrbrbrSPEND SOME TIME EXPLORING OUR HOMES FOR YOUR NEXT VACATIONbrVeriCasa Properties invites you and your family to relax and enjoy beautiful, peaceful, scenery in the mountains or blue invigorating ocean waters to enjoy an exhilarating football game in a college town. VeriCasa has everything in between for you and your family to find a vacation any time of the year.brbrOur Staff is ready to assist you in finding your luxury dream vacation or experience. Read More

    3 Bed
    2 Baths
    Sleeps 8
    $338 / Nightly
  • Property-8 Image 1
    Exceptional
    (2)
    Private Vacation Home
    Magnificent Spacious Home
    Oak Bluffs, Massachusetts, United States

    This lovely and beautifully furnished three-story home is located in a quiet residential section of Oak Bluffs. It is a short distance to the beach, the Gingerbread Cottages and to Circuit Ave for shopping and entertainment. The main floor consists of a living room and sitting room, two twin bedrooms, a bath, and a deck off the living room. The living room has skylights and a cathedral ceiling. There is also a second deck on the main level that will accommodate 12-15 people.brbrThe lower level consists of a good-sized living room/kitchen combined; a large master bedroom with queen bed and sitting area; a small bedroom with twin beds. This level has a separate entrance.brbrThe third floor has a fully equipped kitchen with breakfast bar and a large table that seats ten; a master bedroom with queen bed and skylights; a full bath; and a wrap-around deck that extends from the kitchen to the master bedroom. brbrAmenities include SMART TVs in all bedrooms, Cable and SMART TV in main living room, dishwasher, wireless internet, and washer/dryer. BED LINEN ONLY INCLUDED. Outdoors, you’ll find a quiet, rustic environment for children to play, a large outdoor shower; deck and lawn furniture and an outdoor fireplace for cooking or warmth. There is also room to park 4 cars. Read More

    5 Bed
    3 Baths
    Sleeps 10
    $798 / Nightly
  • Property-9 Image 1
    Exceptional
    (29)
    Private Vacation Home
    Pristine Retreat - Spectacular outdoor space - New Blue Stone Patio and Fire Pit
    Oak Bluffs, Massachusetts, United States

    Welcome to Martha's Vineyard. So many of our guests have returned year after year because they find our property to be centrally located, clean, updated and relaxing. We strive to make our home comfortable, fresh and modern. In fact every year we add something new to make our home even more special and comfortable.brbrThe living area is an architecturally designed living space designed for maximizing the incredible views of the landscaped grounds while providing an airy lounging space for your relaxation. The home has a central air conditioning and dehumidifying system, as well as a wood burning classic fireplace for cozy nights. The dining room has seating for 6 with plenty of room for more with the expandable table. There is a large flat screen Samsung SMART TV with choices of cable, Netflix, Amazon Prime, Hulu and a DVD system. Stream music through the Bose system or play CDs for those who want to bring their own music. The kitchen, which has seating for 3 at the Granite counter, is fully stocked with all the high end pots and pans you will need, including baking equipment, coffee maker, Keurig machine, microwave, toaster oven, etc. Each bedroom is outfitted with its own Samsung flat-screen TVs and cable. The basement has a large TV and ping pong table for those rainy days. There is even a Virtual Concierge System powered by Alexa which will allow you to ask questions about the property or about the island and reach out to the owners just by asking. Of course, you can easily opt-out as well for those tech adverse. brbrThe outdoor oasis begins with a wonderful large Azek rear deck with Pottery Barn Teak furnishings and space for everyone. The deck leads onto a blue stone patio complete with a teak dining table, teak seating, new Lynx grill, and outdoor fire pit for S'mores. Right off the deck is an enclosed outdoor shower, perfect for after the beach or even as your regular everyday shower if you wish. The front porch has seating and is a wonderful space to take in the park like setting, the picturesque meadow directly across from the home, watch sunsets or for star gazing. brbrCentrally located to Edgartown, Vineyard Haven, West Tisbury, Chilmark, and Oak Bluffs. Just a short drive will take you to any of the town beaches and the Sailing Camp Park is a quick bike ride away. The home is located on over a 1/2 acre of landscaped property in a beautiful, private, neighborhood, with private paved roads great for biking and is wonderful for families, friends or even a romantic getaway. The community is exclusive to guests and is tranquil and quiet. The bike path and the bus route is located right off of the community and is a breeze to get to. Within a very short walk is the State Park with jogging trails and places to explore, the newly beautifully redone Vineyard Family Tennis center where you can rent court time. A short distance away is the excellent YMCA with daily or weekly passes for all your workouts complete with babysitting and teen center. brbrPlease note we are a pet free home and while we love animals we are unable to accommodate them on our property. brbrMartha’s Vineyard has been a great vacation location for years and there is lots to do, including gorgeous beaches, fine dining, shopping, golf courses, tennis courts, deep-sea fishing, sailing, kayaking and much, much more.brbrFor more photos follow us on Instagram @vineyardhome24.brhttps://www.instagram.com/vineyardhome24brbrPlease read the Contract and Rider - agreeing to book with VRBO is agreeing to the terms in the Contract and Rider. Read More

    3 Bed
    3 Baths
    Sleeps 6
    $767 / Nightly
  • Property-10 Image 1
    (2)
    Apartment
    Spacious family-friendly home with fast WiFi, beach access, & washer/dryer
    Oak Bluffs, Massachusetts, United States

    Nautical DazebrbrOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'brbrSimply filled with coastal charm, this lovely home will be an amazing jumping-off point for your next vacation to Oak Bluffs! Just down the road from beautiful beaches, this home is perfect for you and your loved ones to enjoy the ultimate east coast getaway. Take a ride on the Oak Bluffs Ferry, spend your day at the quaint fishing bridge, or tour the coastal town to find unique shops, local eateries, arts, entertainment, and an array of family-friendly attractions.brbrInside you'll be met with a bright interior and a warm feeling of welcome throughout the space. The living area invites you in to lounge about the plush furniture, while the kitchen invites hobby chefs to create culinary charms on the stainless steel appliances. Three bedrooms are comfortable and spacious with plenty of room for personal effects. For beachgoers, an outdoor shower is provided for the ultimate convenience of rinsing off and keeping the home clean! At the end of the day, witness a spectacular sunset on the porch with your favorite drink in hand, sealing this destination as one of the most unforgettable.brbrTHINGS TO KNOWbrbrParking notes: There is free parking available for 2 vehicles.brbrbrbrDamage waiver: The total cost of your reservation for this Property includes a nightly damage waiver fee, plus tax if applicable (the “Damage Waiver”). (A discount may be applied for stays of 28 nights or longer, if permitted.) The Damage Waiver covers you for up to $3,000 of accidental damage to the Property or its contents (such as furniture, fixtures, and appliances) as long as you report the incident to the host prior to checking out. The Damage Waiver fee eliminates the need for a traditional security deposit.brMore information can be downloaded from the "Rental Agreement" on the checkout page.brbrDue to local laws or HOA requirements, guests must be at least 21 years of age to book. Guests under 21 must be accompanied by a parent or legal guardian for the duration of the reservation.brbrbrState/province tax number: C0374222210 Read More

    3 Bed
    1 Baths
    Sleeps 8
    $304 / Nightly
  • Property-11 Image 1
    Excellent
    (6)
    Cottage
    OB Cozy-Cottage-Glam off Circuit with Great Outdoor living
    Oak Bluffs, Massachusetts, United States

    Location!!! Location!!! This updated cottage is a quick walk to town, beach, Tony’s Deli, tennis and basketball courts, and so much more. Relax on the wrap around porch , enjoy the outdoor shower after a walk back from the beach, warm up near the fire pit while BBQ is on the grill. Walk to all downtown Oak Bluffs attractions. All new beds and furniture. Bring your fav sheets and bath towels to complete your comfort (Or rent locally on the island). Flexible work week. Work space for telecommuters. Read More

    2 Bed
    1 Baths
    Sleeps 5
    $800 / Nightly
  • Property-12 Image 1
    Wonderful
    (17)
    Private Vacation Home
    Serene Sengekontacket Pond Getaway
    Oak Bluffs, Massachusetts, United States

    The property is set among several private townhouses in a lovely neighborhood located off of Sengekontacket Pond in Oak Bluffs. The townhouse has clean, comfortable accommodations with all the amenities needed to ensure a relaxed vacation. There are 2 bedrooms, 2 baths, kitchen with granite counters, stove , microwave, dishwasher, toaster, blender, spice rack, keurig coffee maker, regular Braun coffee maker, and well supplied kitchen. :There is a washer/dryer, free WiFi, cable, HD television,, and a large private deck with gas grill. The living room is furnished with a gas fireplace and a ceiling fan, and both bedrooms also have ceiling fans. br *Air conditioni8ng has recently been installed for added comfort.brbrbrIn addition to the private amenities, guests have access to the Association's two all-weather tennis courts, a fresh water pond, and a salt water pond for boating, and fishing. The location is conveniently along the bike trail and bus routes and is also near the Farm Neck golf course. Read More

    2 Bed
    2 Baths
    Sleeps 5
    $400 / Nightly
  • Property-13 Image 1
    Excellent
    (20)
    Private Vacation Home
    Downtown Oak Bluffs, short walk to beach & town, Early Sept ferry res. available
    Oak Bluffs, Massachusetts, United States

    Location, location, location. This cozy 3 bedroom house is located steps from downtown on a family neighborhood side street. Stroll among the Gingerbread houses, or into town for groceries, dining and fun...or pack a tote and stroll to the end of our street to Inkwell beach. Everything is within an easy walking distance, including the ferry, playground, fishing pier, Flying Horses carousel, churches and shuttle buses that can take you around the island. brbrTransferable ferry reservations available to guests (at same price we paid) for week Sept 3-10. However, everything is so handy, you might not need a car. If you do want your vehicle on the island, there is off-street parking for two cars in front of the house.brbrThis quaint home features a living room with flat-screen TV, comfy sectional sofa, new (2016) downstairs hardwood flooring, downstairs bathroom with shower, and 3 bedrooms and a small half bath upstairs. Queen bed in the master, double bed in the middle room, and 3 twins in the "kids' room". The kids' room also has a TV in case you need to find a space for them to go and entertain themselves while the adults unwind after a day on the beach. There's also a TV in the master bedroom. There's a private hot/cold outdoor shower off the back porch too. BBQ on the private back patio or relax on the front porch and say Hi to the neighbors as they stroll by. brbrWindow air conditioners and fans, but for those cooler spring/fall evenings, there is electric heat upstairs and down.brbrPerfect for a family or a romantic getaway. This is a weekly Saturday-Saturday rental property however 3 night minimum stays may be considered during during parts of the spring and fall. Read More

    3 Bed
    3 Baths
    Sleeps 6
    $461 / Nightly
  • Property-14 Image 1
    (13)
    Cottage
    Spacious Home - 1500 ft from Beach & Circuit Ave
    Oak Bluffs, Massachusetts, United States

    brNewly renovated four bedroom, two full bathroom home with an inviting front porch, private backyard and footsteps to Circuit Avenue. The first level has an open floor plan with the following: a new fully equipped eat-in kitchen, featuring tile floors and granite countertops; a 32-bottle wine refrigerator and a breakfast bar which seats three people. Also on the first floor is a queen-size bedroom, living room, dining room, family room with entertainment center, bathroom with stand-in shower, and a mudroom.brbrThe second floor room layout includes a master bedroom with a spacious sitting area perfect for reading, relaxing and napping, twin set bedroom, full-size bedroom, and bathroom. Take advantage of the private office/library room adorned with many books, novels and magazines for every reader. The inviting and comforting stone surfaces aren't just in the kitchen, but also included in each of the beach inspired bathrooms.brbrbrThis lovely summer home is walking distance to the beach, ferry, shopping and other attractions. It's a home away from home, and the perfect place for relaxation. Read More

    4 Bed
    2 Baths
    Sleeps 8
    $786 / Nightly
  • Property-15 Image 1
    (18)
    Private Vacation Home
    Within Walking Distance to Town, Beach & Parks, Enclosed yard with a new deck,
    Oak Bluffs, Massachusetts, United States

    Located on historic Circuit Ave in Oak Bluffs within walking distance to town, beach, tennis courts and parks. Minutes away from shopping and restaurants. Handicap Accessible. Fully equipped modern kitchen. Large dining room, living room, and den / family room, gas/oil heat, all bedrooms air conditioned with quilts and pillows on each bed. I do not supply sheets and towels. Read More

    5 Bed
    4 Baths
    Sleeps 12
    $723 / Nightly
  • Property-16 Image 1
    (34)
    Apartment
    Perfect location! By Beach, Harbor & Town! Gorgeous Gingerbread Upstairs Aptmt
    Oak Bluffs, Massachusetts, United States

    This lovely, in-town, impeccably renovated 1800's historic Oak Bluffs upstairs apartment is adored by all who stay here. With landscaped gardens, a beautiful patio with a hot tub, outdoor shower, and an outdoor designer Rais fireplace, and original architectural details, the apartment is truly an oasis in the heart of Oak Bluffs.brbrSurrounded by all the vibrant and colorful life of Oak Bluffs in every direction, there is never a need to commute into town for the islands most popular events. The August Fireworks, Illumination night, concerts on the park are all around the corner.brbrThe apartment is a very short walk along beautiful Ocean Park from the ferry, a couple of blocks from the islands exceptional transportation system, a couple of blocks to State Beach, a block from exceptional restaurants and bars, practically next door to performances at the Tabernacle or Union Chapel, a block from the Methodist Campgrounds with their spectacular and colorful historic Gingerbread houses, a few blocks from the Harbor with its magnificent sunsets and waterfront restaurants and nightlife, and the ice cream shops, arcade, movie theatres and live local music of Circuit Ave. The breathtaking bike path from Oak Bluffs to Edgartown, with water on both sides, begins just a few blocks from the house, and running and walking paths through nature trails are a short jog away. Oak Bluffs truly has everything, and in my heart is the jewel of Martha's Vineyard Island. brbrThe apartment has a sunlit living room with beautiful breezes through many new windows flanking both sides, a kitchenette, full bath, and a lovely and spacious sunlit bedroom with meditation nook and skylight. brbrThe house is very special, with beautiful energy from all the wonderful people who have stayed there and graced its walls and gardens. Up to four people are welcome in this apartment. The living room has a deluxe full height, very comfortable full size air bed. brbrThere may be very carefully selected pets in this rental.brbrHouse Story:brbrI fell in love with this house the minute I saw it. It took me a full winter to be able to be able to call it my own, because when I made the offer the owner was concerned about disappointing someone else, though they had was no contract at all. She was so kind, she spent a few months trying to find this person, who was out of the country and difficult to track down. In the meantime, she knew how much I loved the house, and after several long months she called to say it was mine if I still wanted it, and I could take a few days to let her know. I told her I didn’t even need a few minutes. No other house that I had seen captured my heart as this one had. brbrIt took great amounts of work to prep this house to be my massage center, as it would be for some years before I could make it my home. One day, at my other massage center in Vineyard Haven, I interviewed a lovely massage therapist from Louisiana. I had no idea she had MV ties, but I instantly adored her and her work and hired her on the spot and sent her here to do a massage. Twenty minutes passed, and the phone rang. “You are not going to believe this, Sharon, but this is the house my grandmother grew up in.” brbrOma (grandmother in German), came right over the next day from West Tisbury, where she then summered, brought me this photo of her parents and this house as it was in 1908, and gave me a tour of the house, telling me where all the original details used to be. Oma was beautiful, and her granddaughter is beautiful, as was the previous owner. I just kept feeling that it was no wonder that it feels so special in here. Since that time, my friends, family and guests have only added to that feeling. Time and time again, people walk in and comment on the energy of the home. I feel it deeply myself.brbrTo top off all of this wonder, the last bit of amazement for me was the dog in the photo - a dog with a half black and half white face, split down the middle. On the other side of the couch, you can see the photo of my dog, Haffa, at the time. A dog with a half black and half white face, split down the middle, almost 100 years later.brbrLife is magical, mysterious and beyond imagination.brbrIf these dates are not available, please send us a message. We have other beautiful properties.brbr(Please note: We do have a guest-centered and considerate cancellation policy. Please see our attached cancellation policy for details.) Read More

    1 Bed
    1 Baths
    Sleeps 4
    $145 / Nightly
  • Property-17 Image 1
    (68)
    Private Vacation Home
    Private Meadow View Family Retreat - 4 BR, AC, Large Yard, Tennis, on Bike Path
    Oak Bluffs, Massachusetts, United States

    Located in the desirable, private Meadow View Farms Estates, across from the Farm Neck Golf Club, this charmingly decorated, tranquil, four-bedroom property does not disappoint. Centrally located on the bike path and bus route, it is just a short distance to Oak Bluffs Center with easy access to Edgartown and the up-island roads to Chilmark and beyond. The house is 2 miles from the beach. Guests have access to private tennis and pickleball courts just steps away .brbrOur home itself is a peaceful island residence decorated with a mix of Arhaus, Safavieh, antiques, and other personal touches to make you feel at home and on island time the minute you arrive. There is a great flow for entertaining from the interior living space to the inviting deck and lovely screened-in porch.brbrFour bedrooms comfortably sleep 8: br• First floor master bedroom (queen) with en suite full bath. br• Second floor has three additional bedrooms (queen, queen, and two twin beds) and a second full bath.brbrbrNewly redone, fully equipped kitchen with stainless steel appliances. brbrMagical screened-in porch with comfortable lounge furniture and twinkling lights overlooking large, level lawn and beautifully landscaped grounds.brbrLarge deck with dining table that seats 8-10brbrFinished basement br• pool tablebr• comfortable seatingbr• 65" TVbr• bar with refrigeratorbr• half-bathroombr• separate laundry room with washer and dryerbrbrCentral Air ConditioningbrbrFabulous outdoor shower brbrBecause this is also our summer home, there are other helpful amenities:br• gas grillbr• beach chairs, umbrellas, coolers, and beach towelsbr• lawn games and board games brbrbrBed linens and bath towels not included – available for rent from local service. Many clients prefer to bring their own.brbrWe feel confident you will enjoy your summer vacation as much as we do.brbrSeven day minimum rental in summer.brbrSee rules for cancellation policy.brbrbrbrbrbr Read More

    4 Bed
    3 Baths
    Sleeps 8
    $342 / Nightly
  • Property-18 Image 1
    Excellent
    (9)
    Private Vacation Home
    Spectacular Martha's Vineyard Island Home!
    Oak Bluffs, Massachusetts, United States

    This is our beautiful home on Martha's Vineyard we call Shangri-La! Spectacular setting with a great peaceful view overlooking Sengekontacket Pond with the ocean beyond. The property features a shared Pool, Tennis Courts, and a Dock. Our house is conveniently located midway between the Oak Bluffs & Edgartown town centers.brWhen the Presidents visit the Vineyard this is the area they come to relax (at Farm Neck Golf Club which is right up the street). The property overlooks the Felix Neck wildlife preserve. Read More

    3 Bed
    3 Baths
    Sleeps 12
    $489 / Nightly
  • Property-19 Image 1
    (57)
    Private Vacation Home
    Great location, happy house 0.5 mile Nancy’s & Jetty Beach.
    Oak Bluffs, Massachusetts, United States

    1900's Victorian, renovated and newly furnished. House is located on New York Ave, which is the main road between Oak Bluffs and Vineyard Haven. The bus goes past the house every twenty minutes during the summer and can be flagged. House is approximately 1,600 square feet. House purchased in 2018 and all furnishings and furniture is new. Kitchen and down stairs bathroom are newly renovated! brbrFirst floor includes living room with 50" HDTV, and two large coaches. It is connected to den with sleeper sofa, coffee table, table to play games/puzzles and sitting chair to enjoy a book. Kitchen is eat-in and includes various appliances, including blender, toaster, coffee maker, microwave. brbrOff the kitchen is a bathroom with shower, toilet and sink.brbrThree upstairs bedrooms: 1) master bedroom with small futon, pack and play or air mattress, queen size bed, dresser and side table and closet 2) queen size bed with side table, dresser and closet and 3) full size bed with twin bunks with small half dresser and closet. brbrLarge bathroom with shower and bath on second floor, which connects to master and has access to the other bedrooms. brbrLarge outdoor front porch, picnic table and grill in rear. Window unit AC's in three bedrooms upstairs, den and Kitchen . Mini-split keeps family room cool. Linens and towels (8 bath and 8 beach) provided. brbrOutdoor shower newly installed in 2019.brbrWalking distance to jetty beach (1/2 mile). Four bikes and eight beach chairs. Read More

    3 Bed
    2 Baths
    Sleeps 8
    $269 / Nightly
  • Property-20 Image 1
    (3)
    Apartment
    Cozy studio with free WiFi, private deck & kitchenette - walk to downtown
    Oak Bluffs, Massachusetts, United States

    Nautical Daze - StudiobrbrOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'brbrIdeal for a couple's getaway, this welcoming studio is located within walking distance of Vineyard Haven and Oak Bluffs. Enjoy unbeatable proximity to the darling shops and restaurants that populate this charming town and find your own favorite hangouts, all within a few minutes from your front door. And, you can always hop on the ferry for a day trip on the water!brbrInside, this studio is complete with hardwood floors, a cozy queen-size bed, and all the comforts of home! After a day out exploring the area, return to your sweet spot and settle in for the evening in front of the smart TV to stream your favorite shows. When you need to curb your appetite, the kitchenette is outfitted with a microwave, dishwasher, and coffee maker. And, when the stars come out, another day of adventure awaits tomorrow!brbrThis gem is just what you need to rest and recharge, so book your stay today!brbrTHINGS TO KNOWbrStreaming is available with guests' accounts.brbrParking notes: There is free parking available for 1 vehicles.brbrbrbrDamage waiver: The total cost of your reservation for this Property includes a nightly damage waiver fee, plus tax if applicable (the “Damage Waiver”). (A discount may be applied for stays of 28 nights or longer, if permitted.) The Damage Waiver covers you for up to $3,000 of accidental damage to the Property or its contents (such as furniture, fixtures, and appliances) as long as you report the incident to the host prior to checking out. The Damage Waiver fee eliminates the need for a traditional security deposit.brMore information can be downloaded from the "Rental Agreement" on the checkout page.brbrDue to local laws or HOA requirements, guests must be at least 21 years of age to book. Guests under 21 must be accompanied by a parent or legal guardian for the duration of the reservation.brbrbrState/province tax number: C0374222210 Read More

    1 Baths
    Sleeps 2
    $144 / Nightly
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Oak Bluffs Tourist guide :

What are the most popular tourist destination in a Oak Bluffs ?

Oak Bluffs, Massachusetts is a charming beach town on Martha's Vineyard that is renowned for its beautiful beaches, picturesque architecture, and vibrant summer events. This town attracts visitors from all over the world, and for good reason. Here are some of the most popular tourist spots in Oak Bluffs:

1. Circuit Avenue - This street is the heart of Oak Bluffs and is home to numerous boutique shops, art galleries, restaurants, and cafes. It is a great spot for strolling, shopping, or simply people-watching.

2. Flying Horses Carousel - This is the oldest operating carousel in America and is a must-visit attraction for families with young children. The carousel was built in 1876 and has been delighting visitors ever since.

3. Inkwell Beach - This is one of the most popular beaches in Oak Bluffs and is well-known for its pristine sand and calm waters. It is a great spot for swimming, sunbathing, and picnicking.

4. East Chop Lighthouse - This historic lighthouse is a landmark in Oak Bluffs and offers stunning views of the ocean and the surrounding town. Visitors can take a guided tour of the lighthouse and learn about its rich history.

5. Ocean Park - This park is a popular gathering place for locals and visitors alike. It is a great spot for picnics, playing games, and listening to live music during the town's summer events.

6. Martha's Vineyard Camp Meeting Association - This historic district is famous for its colorful Gingerbread cottages, which date back to the 1800s. Visitors can take a walking tour of the district and learn about the history and architecture of these unique cottages.

Overall, Oak Bluffs, Massachusetts, is a wonderful destination for a summer vacation. With its beautiful beaches, picturesque architecture, and vibrant events, there is something for everyone in this charming town.

What is the average price per night in Oak Bluffs ?

Oak Bluffs, Massachusetts is a popular vacation destination located on the island of Martha’s Vineyard. Known for its stunning beaches, quaint shops, and vibrant nightlife, it is a must-visit location for travelers. If you’re planning a trip to Oak Bluffs and are on the lookout for affordable accommodation, you may be wondering what the average price per night is for a vacation rental.

According to recent data, the average price per night for a vacation rental in Oak Bluffs ranges from $200 to $400 during the peak season, which runs from June to September. However, prices may vary depending on the location, size, and amenities of the rental.

The offseason sees a dip in prices, with rates ranging from $125 to $250 per night. It is helpful to search and book early for the best deals and to avoid paying peak-season prices.

Overall, Oak Bluffs offers a wide range of vacation rental options suitable for any budget. With some research and planning, you can find an affordable and comfortable accommodation that will make your trip a memorable one.

When is the best time to holiday in Oak Bluffs ?

Oak Bluffs, Massachusetts is a charming coastal town on the island of Martha’s Vineyard. Whether you’re looking to explore the beaches, indulge in some fresh seafood, or take in the architecture and culture, there’s something for everyone in Oak Bluffs.

The best times to vacation in Oak Bluffs are during the summer months of June through August. During this time, the island comes alive with festivals and events, such as the famous Martha’s Vineyard Agricultural Fair, the Oak Bluffs Harbor Festival, and the MV Wine Festival. The weather is warm and sunny, making it perfect for beach days, outdoor activities, and al fresco dining. It’s also a great time to catch glimpses of the island’s famous celebrity residents, who often flock to Martha’s Vineyard during the summer.

That being said, if you’re looking to avoid the crowds and take advantage of lower prices, the shoulder seasons of May and September are great options. You can still enjoy the warm weather and explore the town without the hustle and bustle of summer tourism. Plus, the fall foliage in Oak Bluffs is stunning and definitely worth a visit.

No matter when you choose to visit, Oak Bluffs is a must-see destination for any traveler looking to experience the quintessential New England coastal charm.

What are the most popular things to do in Oak Bluffs ?

Oak Bluffs, Massachusetts is a quaint and charming town on Martha’s Vineyard, which is perfect for a relaxing family vacation or romantic getaway. Whether you’re interested in exploring the island’s culture, history, and natural beauty or just taking it easy and enjoying the beautiful beaches, Oak Bluffs has something for everyone. In this article, we’ll go over some of the most popular things to do on vacation in Oak Bluffs.

One of the most iconic landmarks in Oak Bluffs is the Gingerbread Cottages in the Camp Meeting Association. These historic homes are brightly colored and decorated with intricate woodwork, making them a must-see attraction for anyone interested in architecture or history. The cottages are also conveniently located within walking distance of Oak Bluff’s historic downtown area, which features an array of shops, restaurants, and art galleries.

Oak Bluffs also boasts some of the best beaches in the region. The Inkwell Beach is one of the most popular beaches on Martha’s Vineyard, with its calm, clear waters and a beautiful stretch of sand. The Ocean Park Beach is another great destination for beach-goers, with its wide coastline, sweeping views of Nantucket Sound, and excellent amenities.

For adventure seekers, a visit to the Flying Horses Carousel is an absolute must. This iconic attraction is one of the oldest operational carousels in the United States and a National Historic Landmark. With only 20 horses on the carousel, the competition for the brass ring that can win a free ride can be fierce.

Lastly, be sure to visit the Tabernacle, the area’s oldest and largest place of worship, which is now used for a variety of events throughout the year, including concerts, theater performances, and worship services.

Whether you’re looking for a relaxing vacation on the beach, a history-rich adventure, or some good old-fashioned fun, Oak Bluffs is sure to deliver. Start planning your trip today!

Most popular vacation rentals in Oak Bluffs

  • thumb
    $ 370.00 avg/night
    6
    • 1 Beds
    • 2 Baths
    • 2 Guest(s)
    #CozyBluffs #OakBluffs #EastChop 1 BD, 1.5 bath home, walk to town, ferry, beach Oak Bluffs, Massachusetts, United States

    Introducing our #CozyBluffs home in Oak Bluffs on Martha's Vineyard! Designed by local Architect... Read More

  • thumb
    $ 1171.00 avg/night
    1
    • 7 Beds
    • 2 Baths
    • 14 Guest(s)
    Martha’s Vineyard 7 Bedroom Vintage Home! 15 min walk to beaches and Oak Bluffs! Oak Bluffs, Massachusetts, United States

    Fantastic home available for the first time. Seven Bedrooms, two bathrooms and a dreamy outdoor... Read More

  • thumb
    $ 500.00 avg/night
    19
    • 3 Beds
    • 4 Baths
    • 10 Guest(s)
    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... Read More

  • thumb
    $ 390.00 avg/night
    22
    • 3 Beds
    • 2 Baths
    • 7 Guest(s)
    Family & dog friendly; walk to beach, cliff, town, ferries, all bedrooms w/AC Oak Bluffs, Massachusetts, United States

    Best of both worlds! Quietly situated among beautiful trees with few neighbors plus it is walking... Read More

  • thumb
    $ 1229.00 avg/night
    6
    • 4 Beds
    • 3 Baths
    • 8 Guest(s)
    Centrally Located Modern Waterfront Property Oak Bluffs, Massachusetts, United States

    New construction property overlooking Vineyard Haven Harbor where water views can be enjoyed from... Read More

  • thumb
    $ 772.00 avg/night
    2
    • 3 Beds
    • 1 Baths
    • 6 Guest(s)
    Inca Gardens Apt. New To Market - Lg Patio - Pets Oak Bluffs, Massachusetts, United States

    Inca Gardens is a 2nd-floor apartment of a cute house located in a quiet area of Martha's... Read More

  • thumb
    $ 374.00 avg/night
    1
    • 3 Beds
    • 2 Baths
    • 6 Guest(s)
    Fresh Pond Chateau | Newly Renovated Bright & Cozy 3 Bedroom Home Oak Bluffs, Massachusetts, United States

    Summary:Unwind at this stunning newly renovated home with modern furnishing! The home is on a... Read More

  • thumb
    $ 581.00 avg/night
    4
    • 3 Beds
    • 2 Baths
    • 6 Guest(s)
    COZY 3 BR/2 BA CAPE COD IN QUIET NEIGHBORHOOD. CLOSE TO OB CENTER AND LAGOON. Oak Bluffs, Massachusetts, United States

    Located in the beautiful Lagoon Heights neighborhood, you'll enjoy this lovely 3 Bedroom, 2 Bath... Read More

  • thumb
    $ 500.00 avg/night
    1
    • 2 Beds
    • 1 Baths
    • 4 Guest(s)
    Haydens Haven Marthas Vineyard "What a breath of fresh air" Oak Bluffs, Massachusetts, United States

    Welcome to Hayden's Haven MV. Our 2 bedroom 1 bath Charles Suite holds 4 adults comfortably.... Read More

  • thumb
    $ 450.00 avg/night
    7
    • 4 Beds
    • 3 Baths
    • 10 Guest(s)
    MOST CHIC SPOT! Your Martha's Vineyard Getaway! Oak Bluffs, Massachusetts, United States

    Our amazing property is a perfect place to spend with family and friends! The property is... Read More

Most Popular Cities in Massachusetts

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