Vacation Rentals By Owner In Oak Bluffs, MA

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

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

Oak Bluffs, Massachusetts, United States

Bed

Bath

Sleeps

$1076.81

This lovely, in-town, first-floor apartment is in a renovated 1800's historic Oak Bluffs cottage with a fenced in landscaped patio. The beautiful stone patio out the kitchen door has plenty of seating, an outdoor shower, 2-person hot tub (please let us know if you think you will use it), propane bbq grill, and an outdoor designer Rais fireplace. The large and sunlit gourmet kitchen has skylights and is the heart of the home.brbrThis apartment accommodates up to 4 guests, with one very petite queen bedroom and a large living room that can be entirely closed off as a separate room, with a queen Crate and Barrel sofa bed. The room can be closed off from the rest of the apartment for privacy with glass french windows and doors and curtains, and can have a separate entrance as well. The very large country kitchen with every amenity you could hope for.brbrThere is one full bath (with tub/shower) in the apartment, and one additional shower outside, that I have heard is many guests favorite part of their stay! Outdoor showers are a wonderful Martha's Vineyard tradition.brbrMost guests find this home to be a generally quiet oasis for being right in the center of town, but just a reminder that the house IS in the center of town, just not on the main shopping drag. ;)brbrQuiet hours are 9pm to 9am.brbrOne more thing for you dog owners!brWe LOVE dogs and this property is selectively dog friendly (no cats, sorry!!). If you'd like to bring your doggo along, you must ask us first, so we can be sure you agree to our pet guidelines. THANK YOU!brbrThis testimonial below says it all : )brbrThis is a heart house with amazing craftsmanship deep to the bones of the space. Sharon has poured her heart and soul into this place over 10 years, and is now renting out the space for others to experience. The quality and feeling of the space is amazingly restful. The space is BEAUTIFUL, and the main living room feels like a ship. My boyfriend is an engineer by trade, and a meticulous craftsman in all else, and he loved the floors, walls, beams, space, Viking stove, fridge, cabinets -- everything done to great and fine detail. We rented this space as our family was staying nearby -- 16 of them in one house -- and we wanted our own retreat. It was perfect. I loved the front gate with the roses, the two-person hot tub, the outdoor shower, and the courtyard where we cracked crab. And Sharon herself is an amazing person, who supplied us with all the guidance and resources for an amazing trip. Perfect. This is also a place I would feel quite peaceful in renting alone as a solo woman traveler (I do a fair bit of travel). It just feels safe and lovely; restorative.br- KirstinbrbrThis apartment is on floor 1 of 2.brbrIf these dates are not available, please send us a message. We have other beautiful properties.brbr------------------------brHouse 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.)

Apartment

Perfect location! Beach, Harbor & Town. Beautiful 1st Floor Apartment Oasis

Oak Bluffs, Massachusetts, United States

Bed

Bath

Sleeps

$679.14

This Oak Bluffs, Martha's Vineyard rental is a certified National Historic Property. Ideal location for visitors in the middle of the most active, multi-cultural, charming, and fun town on Martha's Vineyard. brbrLiterally just step outside your door for breakfast or ice cream, a great selection of restaurants in all price ranges, or pick up groceries and wine across the street. Have breakfast or dinner on your porch or deck. Stroll to the ocean beach in three minutes. One of the nation's most historic brass ring carousels is just down the street. The famous gingerbread cottages are in your backyard. Frequent concerts and other cultural events are hosted at the historic open air Tabernacle and other local venues. There is no better place on the island to fly a kite than at Ocean Park just down the street where they also have band concerts in the newly restored gazebo. brbrTwo modern, clean, bright, units are available in this historic building right in the heart of the town of Oak Bluffs. Two apartments have a water view. Enjoy your own private deck or front porch with some of the best views in town.brbrBeach, park, restaurants, shopping, movie theaters, game room, historic carousel, bicycle rentals, charming gingerbread cottages, open air concerts, are all at your doorstep. The island ferries from the mainland dock just down the street. The Island shuttle buses to other Island towns operate frequently and are within a four minute walk. Superb in-town location. Ideal for friends, couples, and families with children or teenagers.brbrA CAR IS NOT NECESSARY FOR VISITING THIS PROPERTY.brbrNearby Attractions:brLifeguard Beach, Biking, Fitness Center, Fishing, Shopping, Restaurants, Cinemas, Game Room, Historic Carousel, Parks, Sightseeing, Mini golf, Game Arcade, Swimming, Boating, Jet skis, Sailing, Bi-plane tours, Churches, Historic Tabernacle Concerts.

Apartment

In-Town Certified National Historic Oak Bluffs Property -

Oak Bluffs, Massachusetts, United States

Bed

1

Bath

5

Sleeps

$959.56

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.

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

Oak Bluffs, Massachusetts, United States

4

Bed

10

Sleeps

Exceptional(9)

$884.3

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.

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

Oak Bluffs, Massachusetts, United States

Bed

Bath

Sleeps

$1126.37

*** 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***

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

Oak Bluffs, Massachusetts, United States

6

Bed

Bath

13

Sleeps

$1477.77

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!

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

Oak Bluffs, Massachusetts, United States

Bed

Bath

Sleeps

$1312.48

This lovely four-bedroom shingled Cape overlooks Farm Pond, Harthaven, and Nantucket Sound. It is a vintage cottage comfortable for up to 6 adults, 8 with children. Built in 1900, expanded and renovated in 2009, kitchen remodeled in 2017, central heat/air installed in 2019, porches added in 2022, it is located in historic Oak Bluffs, near the Victorian Camp Meeting gingerbread cottages, center of the long-standing Black community on Martha's Vineyard, and heart of the Vineyard's art district. Have the best of it all: walk to town, beach, nature trails, tennis, bike paths, Oak Bluffs ferry. Close to everything yet very quiet. Peaceful water views from almost every room with glorious, wide upstairs porch and spacious screened in porch off of the kitchen. Very open, light interior, lots of windows, skylights. House is very cozy and inviting. br Enjoy the living room with a custom Lew French beach stone fireplace (currently only candles allowed), a window seat, and comfortable seating. There's a small den with a desk, couch and TV, a dining room with table for 6 or 8 in a pinch, a kitchen with Bosch appliances and a table for 2. Laundry/powder room on first floor. Back screened-in porch with teak dining set for outdoor dinners or shady seating. Upstairs are 4 bedrooms (2 queens, 2 doubles ) with vaulted ceilings, and French doors that open to an upper deck with spectacular 180-degree views of water and the surrounding landscape. Also full bath with tub and separate tiled shower on 2nd floor, 1/2 bath on 1st. There's an 8x10 shed for bikes and equipment in back yard and an outdoor shower. Linens, towels, beach towels included (100% cotton). Wi-fi, Hulu streaming live TV provided. 1-2 blocks from the beach (with lifeguard), bike paths, public tennis courts, playground, and around the corner from Land Bank conservation walking/running paths. Less than a mile from Farm neck golf course. 10 minute walk to town, harbor, restaurants, shops, carousel, campground cottages, ferry and beaches.

Cottage

Waterfront Home in Oak Bluffs - Walk to Town and Beach

Oak Bluffs, Massachusetts, United States

Bed

Bath

Sleeps

$716.75

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!

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

Oak Bluffs, Massachusetts, United States

Bed

Bath

Sleeps

$590.13

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.

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

Oak Bluffs, Massachusetts, United States

Bed

Bath

Sleeps

$2226.16

Newly renovated, Great for Family & Friend Stays, Corporate Retreats, Central Air & Heat, walk to Circuit Ave and Beach, 5 Bedrooms, 3 full baths, galley kitchen, new appliances, dining room, family room, Flat Screen TV, FREE Wifi, washer & dryer, Oak and Pine wood flooring, outdoor shower, wrap around porch, blue stone patio, side backyard, private cobblestone driveway, comfortable beds, pillows and mattresses encased in (non-vinyl) water and allergen proof protectors. COVID-19-conscious cleaning and disinfecting are done regularly.

Soulas Martha's Vineyard, Walk to Inkwell Beach & Town

Oak Bluffs, Massachusetts, United States

Bed

Bath

Sleeps

$1344.39

Fabulous new house in East Chop completed in 2019 located in the heart of East Chop. The house is well appointed, very comfortable and a perfect spot for a Vineyard Holiday.brbrThe First Floor is an open concept design with an attached 3 season room leading to the pool, outdoor shower & bathroom.brThe Second Floor consists of 2 master suites each with a king size bed and a third bedroom with XL twin Bunk Beds and a full bathroom across the hall.brThe Third Floor will have a full bath, 1 bedroom with a queen bed and 1 bedroom with 2 twin beds.brbrPrivate Patio with a 16' x 32' pool, outdoor shower and kingsley bates furniture set. The pool will be set to 81 degrees in July and August. In June & September, the pool can be heated to 81 for an additional $500.brbr1 mile from Oak Bluffs Harbor and East Chop Beach Club.

East Chop Beach House w/Pool

Oak Bluffs, Massachusetts, United States

Bed

Bath

Sleeps

$822.7

** NEW HVAC AIR CONDITIONING * brWelcome to “Gem of the Ocean”! Martha’s Vineyard vacationers dream! This beautiful condo with private balcony and spectacular ocean views is within walking distance to everywhere in downtown Oak Bluffs and a front row seat to all the activity and attractions around Ocean Park: Inkwell Beach, Circuit Avenue, Linda Jeans, Flying Horses, Carousel, OB ferry and harbor, Campground Cottages, Tabernacle, Illumination, shops, restaurants and more! No car needed. brbrBeautiful second floor 2 BR/1 BA condo sleeps up to 4 guests. The master bedroom has a king bed. The second bedroom has full and twin beds, The bathroom has a tub and shower combo, new vanity and chair height toilet. Amazing location with spectacular views! brbrLocated in an historical building, you’ll enjoy this bright and airy space, with views of the ocean and Ocean Park from the private master bedroom balcony. 50” flatscreen smart TV where you can stream your favorite shows and movies. FREE Wi-Fi with 300 Mbps download speed and upload speeds from up to 5 Mbps to up to 10 Mbps. Ample capacity for streaming, gaming, or remote working.brbrThe well-equipped kitchen is a great place to let your creative juices flow preparing meals with island fresh ingredients, or enjoy a plated meal of your favorite island take-out. Enjoy morning coffee on the balcony using your own K-cups or filter brewed coffee.brbrThe dining area seats 4 for meals, yet is also perfect for games, and remote working. Beautiful outdoor space where you can relax and people watch or enjoy a picnic style meal. brbrEach room has state-of-the-art LG minisplit air conditioning and a ceiling fan with light, which keep the unit cool in the summer and warm in the winter. All linen and bath towels are provided. Enjoy quintessential island living in a peaceful setting!brbrWe are award winning hosts who pride ourselves on providing our guests with a memorable vacation experience. Come stay at Gem of the Ocean. It would be our pleasure to host you! brbr** No third party reservations ** There is a 7-night minimum, Saturday check in for August reservations.

Condo

Heart of Oak Bluffs, No Car Needed! Ocean Views, Walk to Everywhere!

Oak Bluffs, Massachusetts, United States

Bed

Bath

Sleeps

$606.31

Our location is the best of both worlds! The house is quietly situated among pine trees with few neighbors, plus it is walking distance to Jetty Beach (5 mins)! And it's only 2 houses from the ocean and scenic East Chop Drive. Take in the sights as you walk, run or bike along the cliffs to the lighthouse. A 15-20 minute walk brings you to the harbor, then to the bustling stores, restaurants, bike rental shops, the gingerbread houses, and the carousel. The large, breezy front porch is perfect for reading, visiting, or eating meals. The house is quaint and like a step back in time. It is not fully air conditioned but has AC where it counts: in the 3 upstairs bedrooms and in 1st floor family room. The main kitchen/dining room/living room area has fans. 1st floor has additional galley kitchen, family room w/ TV, laundry and full bath. 2nd floor has 3 bedrooms (1w/king, 1 w/double & twin, 1 w/queen & twin) and a full bathroom. All bedrooms have their own entrance off the top floor landing. There’s an enclosed outside shower. The large front porch has 2 rockers, several deck chairs, 2 round tables to eat at, and railings to block off stairs (for kids or a dog). There's a hammock on back porch and a charcoal grill out back. Includes Wi-Fi, smart TV w/cable channels & Blue Ray player. Kitchen is fully stocked! Dishwasher & electric stove, microwave, electric coffee maker, lobster pot, plus a full range of cooking supplies. ***SHEETS are provided thru rental & located in plastic bag in front porch***TOWELS (bath, beach in 2nd floor bathroom, kitchen in kitchen closet) are available at the house, but must be washed, dried, and put away upon departure. Vinyl record player with jazz and classical music. There’s also an assortment of games in the family room. Outdoor games include bocce, ladder toss, and badminton. Beach chairs and an umbrella are available. No smoking or candles are allowed in the house. ***ONE DOG is allowed (but no cats due to family allergies). Please let us know if you are bringing a dog. A dog crate and bowls are available. Dog must be kept on a leash and dog waste must be picked up!!! Parking for 2 cars available. Our house is a 7 day rental from Sunday to Sunday during summer.br(If you are interested in booking 2 consecutive weeks, book them at the same time to possibly avoid some repeated fees to Vrbo.)

Family & dog friendly; walk to beach, cliff, town, ferries, all bedrooms w/AC

Oak Bluffs, Massachusetts, United States

3

Bed

Bath

8

Sleeps

$955.04

Relax with the whole family at this peaceful place to stay. Ideally located in East Chop, in walking distance to the Beach, harbor and town. It's on a quiet street on a corner lot. An older Victorian with plenty of space to spread out. Enjoy a BBQ meal on the back sundeck or rock yourself to sleep the front covered farmers porch. It has everything for your family and friends to make great memories. 2 bedrooms have private baths and the other 2 share a bathroom.

Charming, Victorian in East Chop

Oak Bluffs, Massachusetts, United States

Bed

Bath

Sleeps

$1001.78

The perfect vacation awaits you at Frog Prince Cottage in beautiful East Chop, the finest neighborhood in Oak Bluffs. Our fully renovated Victorian beach house seamlessly blends the charm of the island with modern amenities. Wake up to panoramic water views from your bedroom; sip your morning coffee as you watch the ships sail by; bike to the shops on Circuit Avenue and the beauty of Inkwell Beach; or take a 5-minute stroll to Jetty Beach for a relaxing swim. Your night ends in serenity, away from the crowds, with only the sound of ocean waves hitting the shore outside your window. All linens are provided, and beds are beautifully made prior to your arrival.brOur home features a wraparound front porch, as well as a private back deck with a new Weber grill, which is ideal for dining al fresco. A chef's kitchen, cozy dining room, and spacious living room are suited for family gatherings. An outdoor shower, professionally landscaped yard, and private parking are at your disposal. Our home is available year-round, and has updated heating and electrical systems.brBedrooms:brThe Master bedroom is located on the first floor, has a glorious water view, and a king sized bed.brThere are three more bedrooms, plus a bonus room on the second floor:brBedroom 2: Queen bed with water viewbrBedroom 3: Two twin beds with water viewbrBedroom 4: Bunk bedbrBonus Room: Twin bed with water view

Oceanview East Chop Beach House - 4 Bed/2 Bath - 5 min walk to beach

Oak Bluffs, Massachusetts, United States

Bed

Bath

Sleeps

$673.92

Renovated home in East Chop, Oak Bluffs, Martha’s Vineyard. Built in 1872 by my great, great grandfather, the house has the charm of a historical home, but has the modern conveniences for you to enjoy a relaxing vacation on Martha’s Vineyard. The house is located in a quiet wooded area in East Chop, an exclusive area of Oak Bluffs. Just walking distance to downtown Oak Bluffs, the house is conveniently located to Oak Bluffs harbor, jetty beach, great family restaurants, and shopping.brbrThis 4 bedroom, 2 full bath house has just received a substantial renovation including a new kitchen with stainless steel appliances, master suite w/private bath, laundry room, new heating and air conditioning, instant hot water heater, new hard wood floors, all new furniture, new beds and bedding, and all freshly painted. The house has a wrap-around enclosed porch to enjoy a rest after a busy day at the beach and a new flag stone patio in back that includes a gas grill and new outdoor shower.brbrThe house has a large side yard for kids to play and a hammock for those that want to relax and enjoy the quiet setting.brbrWe supply all the amenities which includes sheets, blankets, bath towels, and beach chairs. The kitchen is fully stocked for those that like to cook. Cable TV and WiFi.brbrLike a home away from home, come join us for a relaxing summer vacation on the island.brbrProperty Details:brbr4 Bedrooms & 2 full baths:br 1 Master bedroom on 1st floor with queen size bed and private bath with showerbr 2 bedrooms on 2nd floor with full size beds and shared bath (tub only)br 1 bedroom on 2nd floor with two twin beds and shared bath (tub only)br Outdoor shower with hot/cold waterbrbrRenovated Kitchen:br Eat in kitchen – quartz counter tops, new cabinetsbr Refrigerator w/ice maker, dishwasher, electric stove, oven, microwave, toaster oven, coffee potbrbrFully stocked kitchen including all necessary small wares (i.e. glasses, plates, silverware, pots/pans, cooking utensils, etc.)brbrFamily Room:br Sectional sofabr Flat screen TV, cable, and Wi-FibrbrDining room w/ large table that seats 8 adultsbrbrLaundry room with washer & dryerbrbrEnclosed wrap-around front porchbrbrFlag stone patio with patio furniture & gas grillbrbrRental week is from Sunday to Sunday

Historic Home in East Chop

Oak Bluffs, Massachusetts, United States

Bed

Bath

Sleeps

$767.94

(Note: for 2025, we are renovating the upstairs bath and creating a more spa-like shower. New Photos by late March, roughly). This home is perfectly located - a short walk to Inkwell Beach, downtown Oak Bluffs, and the OB Ferry. One side of the home is bordered by the Nashawena Park Greenway, which offers a pleasant stroll to the beach and waterfront, while just around the corner you will find tennis and basketball courts, as well as a playground. There is also a convenience store just steps away.brInside the home you will find a freshly renovated kitchen, two full bathrooms with modern renovations, central AC, antique hardwood floors, and high efficiency washer/dryer. Outside, there is a large wrap-around farmers porch with gas grill and large outdoor dining table, as well as an adjacent outdoor shower with changing area. Bedroom on first floor can also be used as a den, with TV and a desk. You may also want to check out my other listings: 43151 and 43322.brbrKeywords: House

Location, Charm, & Steps to Town/Beach -- Central AC, 100% Renewable Energy

Oak Bluffs, Massachusetts, United States

4

Bed

Bath

8

Sleeps

$635.33

Escape to The Winthrop, a refined Vineyard retreat set on a serene ⅓ acre just moments from the heart of town. Thoughtfully designed for relaxed luxury, this cottage pairs central air, a chef-grade stove, dishwasher, and in-home laundry with the timeless character of classic island living. Open the doors to a deck overlooking a lush, private lawn, perfect for slow mornings and family gatherings. Stroll 2 minutes to the general store, or enjoy an easy 10 minute walk to town and nearby beaches. The space: Seamless Indoor/Outdoor Living: Access the expansive deck and verdant lawn from 3 different areas of the house. Bask in the sun or find shade under the canopy of trees, creating the ideal spot for lazy afternoons, alfresco dining, or simply sipping the beverage of your choosing. And for those beach days, don't forget to take advantage of the outdoor shower after your short walk home. Thoughtful Renovation: Meticulously restored in 2007, the house retains its original character while offering modern conveniences. From the exposed beams to the cozy fireplace, every detail reflects the care put into preserving its unique personality. Bed/Bath Layout: 1st floor- 1 bedroom (Queen); 1 living room pullout sofa (Queen)/2 full baths 2nd floor- 2 bedrooms (1 Queen; 2 Twins)/no baths Comfortable Living: The cottage offers a retreat for up to 8 guests. Each room is adorned with cozy furnishings, creating an atmosphere of comfort and relaxation. Local Delights: Immerse yourself in the local scene with a short walk to town, where you'll find quaint shops, delightful eateries, and the vibrant energy of the community. The beach beckons for leisurely strolls and breathtaking sunsets, offering the perfect backdrop for unforgettable moments. Additional Amenities: High-speed Wi-Fi Outdoor seating and dining Outdoor shower AC Washer and dryer Parking for 2 cars Unwind in this idyllic Vineyard Cottage, where the fusion of history and modern comfort creates a truly memorable escape. Book your stay now and experience the best of Vineyard living. Other Things to Note: The staircase leading to the second floor—where two bedrooms are located—is original to the home and quite steep. Guests should use extra caution when going up or down the stairs. There are 3 bedrooms that each sleep 2 ppl (Primary/ Bedroom 1- 1 queen bed. Bedroom 2- 1 queen bed. Bedroom 3- 2 twin beds, specifically 1 day bed with additional pop up twin trundle bed). The living room also has a pullout sleeper sofa with a queen mattress that sleeps an additional 2.

Walk to Beach Spacious Retreat

Oak Bluffs, Massachusetts, United States

3

Bed