Vacation Rentals By Owner In Oak Bluffs, MA

Victorian Cape Cod Cottage located in the highly desired Oak Bluffs Copeland District in Martha's Vineyard. Large family home, with a great porch and eat-in-kitchen! Sleeps 10. Two blocks walking distance to downtown Oak Bluffs and beaches. Walking distance to Oak Bluffs center, gingerbread cottages, OB harbor, Steamship Authority ferry, restaurants and more.... Off-street parking, Wireless Internet and Cable TV.

Large, Charming Vintage Cape Cod Cottage, 2 Blocks to Town and Beaches!

Oak Bluffs, Massachusetts, United States

Bed

Bath

Sleeps

$1843.05

Free SSA auto reservation with 6/20-27, 7/4-11 or 8/22-29 booking. brAsk about Discounts if 8 or fewer guests. 3200 sq. ft., waterfront, highly energy efficient, 4 bedroom plus flex room (sleeps 8-9 adults plus 3-4 children) 3.5 bath, central air-conditioned home, flooded with fabulous sunsets on and over the water! Private Lagoon (saltwater) beachfront. EV charger. 1200 Mbps Wi-Fi. Located in a quiet neighborhood, a 15-20 minute walk to and through the Gingerbread Cottages of the Camp Meeting Association and on into Oak Bluffs Center; an easy walk or bike ride into town. brbrSwim, kayak, paddleboard, windsurf, sail or fish right from the beach on the Lagoon or out onto Vineyard Sound (under the drawbridge).....with the sun rising or setting all around you. The water views include glorious sunsets, the ferries and sailboats coming and going in the Lagoon, the harbor and Vineyard Sound. Bring or rent a boat- tie up at our mooring and enjoy beautiful, relaxing days on the water. (Advance notice required for mooring use). BBQ on the sunset-facing upper deck or cook in the fully equipped kitchen. Includes 46 kayaks and 4 paddle boards for your use.brbrThis 5 bedroom, 3 1/2 bath home has an upside-down living orientation featuring a sunset flooded cathedral ceiling living/dining room and fully equipped kitchen, a lav designed in glass and a Master Bed/Bath located on the upper level. The over-sized glass windows on the Lagoon/water-view side nurture beautiful, natural light all day and the awesome colors of sunset as the day gradually draws to a close.brbrThe entry level has 3 bedrooms (2 w/ Queen and a 3 child bunk-room), double-sink full bathroom, laundry, media room and a kitchenette; which is provided for easy entertaining in the back yard or on the private beach. As well as an H/C outdoor shower on the porch. brbrOn the lower level, a 2nd, 700 sq ft, master with en-suite bath and a king bed and sectional (w/ pull-out Full) walks out to the backyard/Lagoon beach.brbr**Need To Know - Neighborhood quiet hours are strictly observed from 9 p.m. to 8:00 a.m. Large parties and other events are not permitted at the property.

Glorious Sunsets and Fun on Private Waterfront in Beautiful, Comfortable Home.

Oak Bluffs, Massachusetts, United States

Bed

Bath

Sleeps

$662.22

Lovely 3 bedroom, 2 full bathroom home with huge deck is less than 1 mile walk to famous Circuit Avenue in Oak Bluffs and 1 1/2 mile to sandy public beach. Setting is quiet and serene, but is easily accessible to all amenities nearby. Property abuts walking trails, bike paths and it is only 5 minute walk to public bus routes. House sleeps 6 with 1 master queen bedroom, 1 double bedroom and 1 twin bedroom. Fully equipped home. Owner occupied in basement level, but the additional 500 square feet with queen bed, kitchenette and full bathroom may be available for additional fee.brbrMA Room Occupancy Excise Registration:brAccount ROC-19314923-002brCertificate C0097692210

Island Serenity: Beautiful home in quiet neighborhood close to Oak Bluffs

Oak Bluffs, Massachusetts, United States

Bed

Bath

Sleeps

$439.18

Pet Friendly w/ Fee | BBQ Ready | Outdoor ShowerbrbrSeeking a relaxing Martha’s Vineyard escape Look no further than this Oak Bluffs vacation rental! With a prime location offering easy access to sandy beaches, kayak rentals, sunset cruises, and more, this 2-bedroom, 1.5-bath house ensures a memorable island experience. Shop and dine along Circuit Avenue or enjoy a stroll through the iconic Gingerbread Houses neighborhood. Then, return home to end the day unwinding around the fire pit.brbr-- THE PROPERTY --brbrC0172552210brbrSLEEPING ARRANGEMENTSbr- Bedroom 1 (Loft): 1 queen bedbr- Bedroom 2: 1 full bedbrbrINDOOR LIVINGbr- Flat-screen TVsbr- Board gamesbr- Wood-burning fireplacebr- Dining tablebrbrOUTDOOR LIVINGbr- Furnished deckbr- Patio w/ fire pit, charcoal grillbr- Private yardbrbrKITCHENbr- Refrigerator, stove/oven, microwavebr- Keurig & drip coffee makers, air fryerbr- Dishware & flatware, cooking basicsbrbrGENERALbr- Self check-inbr- Free WiFi br- Standalone heating units, window A/C unitsbrbrFAQbr- Towels/linens not providedbr- Pet fee (paid pre-trip)br- 4 exterior security cameras (facing out)brbrACCESSIBILITYbr- 2-story house, 4 steps required to enterbr- Full bathroom on 2nd floorbrbrPARKINGbr- Driveway (2 vehicles)br- Free street parkingbrbr-- THE LOCATION --brbr- Walking distance to library, basketball & tennis courtsbr- Near restaurants & shops, kayak & bike rentalsbr- 0.9 miles to Inkwell Beach, 3 miles to Joseph Sylvia State Beachbr- 3 miles to Martha's Vineyard Museumbr- 4 miles to Island Alpaca Companybr- 6 miles to Martha's Vineyard Airport, 85 miles to Boston Logan Int’l Airportbrbr-- 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- Pet friendly w/ $150 fee (+ fees & taxes, 1 max)br- No events, parties, or large gatheringsbr- Must be at least 18 years old to bookbr- Additional fees and taxes may applybr- Photo ID may be required upon check-inbrbrADDITIONAL INFORMATIONbr- This 2-story house requires using 4 steps to enter; interior stairs are required to access the full bathroom on the 2nd floorbr- Towels and linens are not provided at the property. You will need to supply your ownbr- Your safety matters. This property features 4 exterior security cameras. Camera 1 is by the front door facing outward. Camera 2 is on the front of the house facing the front yard. Cameras 3 and 4 are on the side of the home facing the driveway. These cameras do not look into any interior spaces. The cameras record audio when activated by motion

< 1 Mi to Beaches: Home w/ Deck in Oak Bluffs

Oak Bluffs, Massachusetts, United States

Bed

1

Bath

4

Sleeps

$892.64

Consider this house your home away from home while you explore Oak Bluffs. Soak up the Vineyard vibes in this bright and breezy 4-bedroom, 2-bath getaway — just a short stroll to the beach and a 10-minute walk through the charming gingerbread cottages to town.brbrThis relaxed ranch-style home is all about easy island living. Enjoy an open living, dining, and kitchen space, stay cool with AC in every bedroom and the main living area, and unwind on the wraparound porch or side deck. A private driveway, yard, fresh linens, and towels make your stay completely effortless — and we're always just a message away if you need anything.

Bright 4BR Oak Bluffs Home – Walk to Town & Beach!

Oak Bluffs, Massachusetts, United States

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Bath

Sleeps

$730.52

Introducing our #CozyBluffs home in Oak Bluffs on Martha's Vineyard! Designed by local Architect Chuck Sullivan and built in 2013 #CozyBluffs is nestled in a quaint, historic Oak Bluffs residential neighborhood and #CozyBluffs is walking distance to Circuit Ave, Hi-Speed and Auto Ferry and town beach!brbrThis 755 Sq Ft split level standalone house has one large bedroom with a custom Saatva Cal King bed, ensuite bath and balcony. There is a flex space loft with reading niche, desk/work area so you can work and play! The first floor features an open concept living, kitchen and dining areas & a 1/2 bath. There is a full basement accessed from the living room with washer/dryer/drying rack/iron and ironing board. brbrPrivate and enclosed outdoor area includes an expansive private backyard with BBQ, dining and seating areas, and outdoor shower. There is a parking area in front of the house. #CozyBluffs is located only .5 miles from Circuit Avenue, Jetties Beach and the Oak Bluffs ferry terminal. Enjoy the quintessential mix of modern luxury with an Oak Bluffs vibe that is #CozyBluffs!

#CozyBluffs #OakBluffs #EastChop 1 BD, 1.5 bath home-Walk to Town-Ferries-Beach!

Oak Bluffs, Massachusetts, United States

Bed

Bath

Sleeps

$873.02

Twin PondsbrbrOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'brbrNestled just a stone's throw away from the renowned Farm Neck golf course in Oak Bluffs, MA, this spacious house offers the perfect retreat for your Martha's Vineyard getaway. Explore the area's natural beauty and attractions, from the nearby beaches to the historic sites and lively town center. Take advantage of the various activities available, from stand-up paddle boarding on the bay to whale watching, fishing, and kayaking. Whether you're interested in water activities like kayaking and jet skiing or prefer hiking and cycling adventures, Oak Bluffs offers something for everyone. brbrThe Tower Ridge complex, located across from the Farm Neck golf course, provides a picturesque setting for your vacation. Enjoy the convenience of amenities such as a tennis court, central AC, a wood-burning fireplace, a washer/dryer, and smart tvs in all of the bedrooms, ensuring a comfortable and enjoyable stay. Also, with the totally renovated bathrooms featuring luxurious showers with body sprays, you'll feel pampered and relaxed during your stay. When you step outside onto the deck or patio, complete with patio furniture and a gas grill, you will find the perfect setting for outdoor gatherings and al fresco dining.brbrWith easy access to local attractions, restaurants, and shops, you'll have everything you need for a memorable vacation. Whether you're seeking adventure, relaxation, or family fun, this house in Oak Bluffs is the ideal home base for your Martha's Vineyard getaway. Book now and start planning your dream vacation in this beautiful coastal town!brbrThings To KnowbrbrParking notes: There is free parking available for 5 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 25 years of age to book. Guests under 25 must be accompanied by a parent or legal guardian for the duration of the reservation.

Spacious island home near Farm Neck Golf Course, the beach and town

Oak Bluffs, Massachusetts, United States

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Bath

Sleeps

$800.78

Victorian by the SeabrbrOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'brbrA unique coastal stay awaits you and yours at this newly renovated, grand Victorian cottage boasting a prime location, hardwood flooring throughout, and even peek-a-boo ocean views. Enjoy the ocean air from the enclosed yard, which is equipped with plush outdoor seating. When it comes time to explore Oak Bluffs and beyond, head for Ocean Park, both only a short stroll away. With Circuit Avenue, shopping, dining, and the beach only a stone's throw from your door, you'll have countless activities available at your fingertips. Similarly, visit Inkwell Beach, Lighthouse Beach, and Island Alpaca Company. Situated just a few blocks from the iconic Flying Horses Carousel, easily immerse yourself in the nostalgic charm of this historic attraction. For those seeking outdoor adventures, Joseph Sylvia State Beach, known for its ideal conditions for windsurfing, is just a short distance away.brbrWhen you and your group aren't enjoying the ambience of the wraparound porch, head inside where you'll quickly discover an abundance of historic charm mixed with modern convenience. The light-filled living room boasts plush leather seating, a large smart TV, and gorgeous front windows. Follow the gingerbread detailing into the updated kitchen, which features new appliances. The dining room, front parlor, den, sunroom, and bar space are all also available on the first floor.brbrAfter days spent under the sun and in the sand, enjoy rinsing under a warm stream of water in the walk-in shower or opt for a soak in the soaking tub. The interior perks include the laundry room, partial air-conditioning, and internet access. brbrThings to KnowbrCheck-in time: 4:00 PM.brCheck-out time: 10:00 AM.brStreaming services are available with guests' own accounts.brAll guests shall abide by our good neighbor policy and shall not engage in illegal activity. Quiet hours are from 10:00 PM to 8:00 AM.brNo smoking is permitted anywhere on the premises.brbrParking notes: There is free parking available for 3 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 25 years of age to book. Guests under 25 must be accompanied by a parent or legal guardian for the duration of the reservation.

Historical house with wraparound porch, modern updates, enclosed yard, & W/D

Oak Bluffs, Massachusetts, United States

6

Bed

3

Bath

12

Sleeps

$506.57

Fresh Pond ChateaubrbrOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'brbrWelcome to Fresh Pond Chateau, a beautifully renovated cottage nestled on a serene private road in Oak Bluffs, MA. This bright and cheerful single-level home is the perfect island escape for both relaxation and exploration, comfortably accommodating up to six guests with two cozy bedrooms, a stylish den featuring a queen pullout sofa, and two spa-inspired bathrooms. From the moment you arrive, you’ll feel at ease in this inviting retreat.brbrThe open-concept living space is bathed in natural light, creating a warm and welcoming atmosphere for gathering with loved ones or enjoying a movie night on the Smart TV. The fully equipped kitchen boasts stainless steel appliances and all the essentials needed to whip up your favorite island meals. Whether you’re savoring breakfast by the window or grilling dinner on the deck, Fresh Pond Chateau is designed for easy, laid-back living.brbrStep outside to discover a spacious wraparound deck and private patio, complete with outdoor furniture ideal for sipping morning coffee or sharing meals under the stars. After a day of beach adventures, unwind around the fire pit, enjoy a board game with the family, or simply soak in the soothing sounds of nature.brbrPerfectly located just minutes from sandy beaches, charming boutiques, delicious restaurants, and beloved island landmarks like the historic Flying Horses Carousel, this cottage serves as an excellent home base for your Martha’s Vineyard adventure. With high-speed Wi-Fi, a washer and dryer, private parking, and all the cozy comforts you need, Fresh Pond Chateau is ready to host your unforgettable getaway. brbrWhether you're here for sun-soaked beach days or quiet mornings on the deck, this charming home invites you to experience the magic of Martha’s Vineyard at your own perfect pace!brbrThings to KnowbrCheck-in time: 4:00 p.m.brCheck-out time: 10:00 a.m.brAll guests shall abide by our good neighbor policy and shall not engage in illegal activity. Quiet hours are from 10:00 p.m. to 8:00 a.m.brNo smoking is permitted anywhere on the premises.brbrParking notes: There is free parking available for 2 vehicles.brbrSecurity camera details: On the exterior, pointing away from the house.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 25 years of age to book. Guests under 25 must be accompanied by a parent or legal guardian for the duration of the reservation.

Stylish island retreat with sunny interiors, wraparound deck, firepit & AC

Oak Bluffs, Massachusetts, United States

3

Bed

Bath

6

Sleeps

$609.17

TumbleINNbrbrOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'brbrWelcome to your ideal island retreat in Oak Bluffs, where unforgettable family vacations and getaways come to life. This charming house is just steps from the vibrant village center, placing you within easy walking distance of sandy beaches, the historic Flying Horses Carousel, and a variety of boutiques, restaurants, and local attractions.brbrStep outside to enjoy the yard, complete with comfortable seating and an outdoor shower, perfect for laid-back summer evenings. Inside, the cozy living room invites you to unwind with a movie night, while the kitchen includes a drip coffee maker, toaster, and all the essentials you need to prepare meals with ease. The home features a restful queen bedroom and a two twin bedroom, comfortably accommodating small families or extra guests.brbrAdditional amenities include a hair dryer, an ironing board, mini split ACs, and convenient access to an EV charging station just steps away at the nearby town library, making it easy to power up while you explore.brbrWhether you're spending the day beachcombing, browsing local shops, or heading out for a whale watching or fishing tour, this Oak Bluffs gem is the perfect base for your island adventures. Book your stay today and experience the best of Martha’s Vineyard!brbrThings to KnowbrCheck-in time: 4:00 p.m.brCheck-out time: 10:00 a.m.brAll guests shall abide by our good neighbor policy and shall not engage in illegal activity. Quiet hours are from 10:00 p.m. to 8:00 a.m.brNo smoking is permitted anywhere on the premises.brbrParking notes: Street parking is available on a first-come-first-serve basis; parking is not guaranteed.brbrbrbrbrDamage 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 25 years of age to book. Guests under 25 must be accompanied by a parent or legal guardian for the duration of the reservation.

Cozy island cottage near local attractions with breezy yard & inviting interior

Oak Bluffs, Massachusetts, United States

Bed

1

Bath

4

Sleeps

$885.65

Beach HousebrbrOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'brbrNestled in a tranquil neighborhood of Oak Bluffs, this charming and spacious home offers the perfect retreat for families and friends looking to explore the scenic beauty and seaside charm of Martha’s Vineyard. Just a short stroll away, you’ll find the picturesque Oak Bluffs Harbor and the inviting sands of Inkwell Beach, as well as a delightful mix of restaurants and shops that give the town its unique character. For a one-of-a-kind experience, don't miss a ride on the Flying Horses—the oldest operating carousel in the United States. With the ferry terminal just a short walk from the house, travelers will enjoy easy access to convenient service to Falmouth or Hyannis.brbrThe property features a generous outdoor space designed for relaxation and togetherness. The large yard is perfect for family games or lounging in the sun, while the patio and deck offer great spots for enjoying morning coffee, afternoon barbecues, or evening wine. Gather around the outdoor dining area or cozy up at the gas fire pit under the stars for unforgettable island nights.brbrInside, the home is equipped with everything you need for a comfortable and convenient stay. Amenities include air conditioning, Wi-Fi, and a kitchen with modern appliances such as a refrigerator, stove, and dishwasher. The spacious living room is perfect for enjoying a movie, playing board games, or just relaxing after a day of exploration. A dedicated dining area brings everyone together for shared meals and conversation.brbrFeaturing four queen beds along with four twin beds, the home easily accommodates families and groups. Plus, it’s dog-friendly, so your four-legged family members are welcome too!brbrWhether your plans include beachcombing, whale watching, sightseeing, or simply unwinding in your own private oasis, this Oak Bluffs getaway is the ideal base for your Martha’s Vineyard vacation. Book your stay today and start making lasting memories in this beautiful coastal retreat.brbrThings to KnowbrCheck-in time: 4:00 p.m.brCheck-out time: 10:00 a.m.brAll guests shall abide by our good neighbor policy and shall not engage in illegal activity. Quiet hours are from 10:00 p.m. to 8:00 a.m.brNo smoking is permitted anywhere on the premises.brbrIf you are bringing a dog on your trip, the pet fee is already included in your quote when selecting ‘Yes’ to pets. No more dogs are allowed.brParking notes: There is free parking available for 3 vehicles.brbrSecurity camera details: Outside facing the streetbrbrbrbrDamage 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 25 years of age to book. Guests under 25 must be accompanied by a parent or legal guardian for the duration of the reservation.

Charming home with walkable beach, large yard, deck, fire pit, and A/C

Oak Bluffs, Massachusetts, United States

Bed

Bath

Sleeps

$1000.86

Sunny Side UpbrbrOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'brbrFreshly remodeled with brand new furnishings throughout, this Oak Bluffs home is the perfect blend of modern comfort and classic Vineyard charm. Spend your mornings with a newspaper and a cup of coffee on the porch swing, relish in the cool island breezes on the sun deck and the back deck, and enjoy wonderful access to local beaches, the ferry terminal, and downtown Oak Bluffs!brbrWhat's nearby: brThis home sits just over a mile west of the Oak Bluffs Steamship Authority Terminal, on large grassy property lined with trees. In downtown Oak Bluffs to the east, you'll find grocery stores, coffee shops that include Mister Pugg's Mugg and Martha's Vineyard Gourmet Cafe & Bakery, and restaurants such as Sea Smoke Barbecue and Chef Deon's Kitchen. You'll also be only a mile west of Inkwell Beach, Oak Bluffs Town Beach, and the historic Flying Horses, and four miles northwest of Joseph Sylvia State Beach.brbrThings to know:brFree WiFibrFull kitchen brWindow AC units in every bedroombrWood burning fireplace is for decorative purposes only - not for guest usebrbrParking notes: There is free parking available for 4 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.

Newly remodeled home w/ new furniture, large yard & great porches

Oak Bluffs, Massachusetts, United States

Bed

Bath

Sleeps

$304.86

Yellow Brick Road HousebrbrOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'brbrBright and inviting, this home provides an ideal escape for your family's next coastal vacation. Venture to nearby beaches and eclectic shops during the daytime, then return home to spend more time outdoors in your spacious backyard. Rinse off in the outdoor shower before you fire up the propane grill for a barbecue. Listen to favorite playlists on the speakers while you dine at the shaded six-person dining table. A hammock provides a convenient spot to kick back with a good book, while the front yard offers more space for lawn games.brbrLarge windows invite natural light into the living area. Cozy up by the gas fireplace while you stream favorite shows on the smart TV. Outfitted with stainless steel appliances, the modern kitchen features everything you need to whip up family recipes. Keep the chef in your group company at the kitchen's three-person bar. A foldaway breakfast nook provides additional seating for at-home meals. Central AC provides comfort throughout the home while a washer/dryer adds convenience during your stay.brbrTHINGS TO KNOWbrStreaming is available using your own accounts.brbrParking 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.

Coastal home with outdoor shower, grill, fireplace, central AC, & W/D

Oak Bluffs, Massachusetts, United States

Bed

Bath

Sleeps

$970.98

Seabreeze RetreatbrbrOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'brbrWelcome to your perfect summer retreat in Oak Bluffs, MA! This charming house features four spacious bedrooms and two full baths, making it an ideal getaway for families or groups looking to enjoy the beauty of Martha's Vineyard. With central air conditioning on the first floor and window units in each bedroom, you’ll stay cool and comfortable during those warm summer days. The outdoor shower is perfect for rinsing off after a day at the beach, and the open front porch and screened-in back porch provide lovely spaces to relax and enjoy the fresh air.brbrConveniently located, this home is just a short walk to the vibrant town of Oak Bluffs, where you can explore local shops, dine at delicious restaurants, and soak up the sun at the nearby beach. The ferry transportation to Woods Hole is also within walking distance, making it easy to venture out and explore the surrounding areas. brbrThis dog-friendly property offers a parking pad for two cars, ensuring you have everything you need for a hassle-free stay. Inside, you’ll find a well-equipped kitchen with modern appliances, a cozy living room with a TV and DVD player, and a laundry room with a washer and dryer for your convenience. brbrWhether you’re looking to enjoy a day of beachcombing, whale watching, or simply relaxing with a good book, this Oak Bluffs summer house is the perfect home base for your adventures. Book your stay today and create unforgettable memories in this beautiful coastal destination!brbrThings to KnowbrCheck-in time: 4:00 p.m.brCheck-out time: 10:00 a.m.brAll guests shall abide by our good neighbor policy and shall not engage in illegal activity. Quiet hours are from 10:00 p.m. to 8:00 a.m.brNo smoking is permitted anywhere on the premises.brbrIf you are bringing a dog on your trip, the pet fee is already included in your quote when selecting ‘Yes’ to pets. No more dogs are allowed.brParking notes: There is parking available for a fee and charges will apply 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 25 years of age to book. Guests under 25 must be accompanied by a parent or legal guardian for the duration of the reservation.

Spacious colonial home close to town with AC, porches, & W/D

Oak Bluffs, Massachusetts, United States

Bed

Bath

Sleeps

$582.03

The RootskellerbrbrOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'brbrNestled at the end of a tranquil cul de sac, this charming cabin-style home in Oak Bluffs, MA, offers a warm and inviting ambiance that welcomes you from the moment you arrive. With its updated exterior and cozy interior, this property serves as the perfect home base for those eager to explore the beauty of Martha's Vineyard. The open layout and quaint decor create an inviting atmosphere, ideal for unwinding after a day filled with adventure. The fenced in yard is the perfect place to relax and watch the children playing. Enjoy movie nights on the flatscreen TV or simply relax with loved ones in this delightful retreat.brbrConveniently located just a mile from the Oak Bluffs Ferry and the picturesque village green, you'll find yourself in close proximity to the island's vibrant entertainment and dining options. The famous gingerbread homes of Oak Bluffs are also nearby, adding a touch of charm to your stay. For beach lovers, Inkwell Beach is just a short drive away, perfect for soaking up the sun and enjoying the ocean breeze. If you're a golf enthusiast, the immaculate greens of Farm Neck Golf Club await just a quick drive from your doorstep.brbrThis home is not only a serene escape but also a gateway to the island's many attractions. Film buffs will appreciate the proximity to the iconic Jaws Bridge, located just five miles away. Whether you're interested in whale watching, kayaking, or simply exploring the local shops and restaurants, Oak Bluffs has something for everyone. After a day of exploration, return to your cozy haven, where you can enjoy the comforts of home, including a fully equipped kitchen and outdoor dining area.brbrWith amenities such as central AC, a washer/dryer, and a spacious deck, this Oak Bluffs home is designed for your comfort and convenience. Experience the best of Martha's Vineyard while enjoying the rustic charm of this delightful property. Book your stay today and create unforgettable memories in this beautiful island getaway!brbrThings to KnowbrbrParking notes: There is free parking available for 4 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 25 years of age to book. Guests under 25 must be accompanied by a parent or legal guardian for the duration of the reservation.

Quaint, ranch style home in Oak Bluffs with central air

Oak Bluffs, Massachusetts, United States

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East Chop 90brbrOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'brbrWelcome to coastal living on the East Chop, a perfect place to bring loved ones for a getaway from the hustle and bustle of everyday life. This renovated home is full of contemporary creature comforts but honors the character and charm of old vineyard living. Rent water equipment to spend your days on the ocean kayaking, paddleboarding, sailing, surfing, and every other waterfront activity imaginable. Bring your golf clubs for world-class greens nearby, and enjoy exquisite walkable neighborhoods full of Martha's Vineyard magic.brbrThe architectural style draws one immediately to the wrap-around porch. Upon entering the home, the sparkling vintage fir floors, beadboard wainscoting, and a beautiful place to relax and unwind awaits. Many viewing windows and french doors bathe the rooms in natural light, creating a perfect cozy atmosphere. Relax and make yourself at home by resting on the plush furniture, streaming your favorite movies on the large TV, or curling up with a good book. Create culinary charms in the sophisticated galley-style kitchen, equipped with stainless steel appliances, a breakfast bar, and a dining table. Comfortable beds in spacious bedrooms ensure that everyone will enjoy a wonderful night's rest from the day's adventures.brbrIn the guest house, you'll find a nice flex space and kitchenette with a mini-fridge, microwave, and toaster oven. A studio guest room with an en suite bathroom makes this a great private space for those who want their own accommodations. brbrTHINGS TO KNOWbrTo use streaming services, guests must log in with their own credentials.brbrParking notes: There is free parking available for 3 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 25 years of age to book. Guests under 25 must be accompanied by a parent or legal guardian for the duration of the reservation.

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

Oak Bluffs, Massachusetts, United States

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$329.95

Sankofa StudiobrbrOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'brbrNestled in the historic Vineyard Highlands at the beginning of the African American Heritage Trail, this charming studio in Oak Bluffs, MA, offers a unique and comfortable setting for your vacation. The newly renovated studio is located in the sought-after East Chop area, providing a perfect blend of tranquility and convenience. Just a short walk away from Circuit Ave, Oak Bluffs Harbor, the beach, and the iconic East Chop Lighthouse, you'll have easy access to all the town's attractions while still enjoying a peaceful setting. Parking for one is included directly in front.brbrExplore the area's natural beauty and attractions, from the nearby beaches to the historic sites and lively town center. Whether you're interested in water activities like kayaking or prefer cycling adventures, Oak Bluffs offers something for everyone. After a day of exploration, unwind in the comfortable living space with queen bed and stream your favorite shows. brbrDon't miss the chance to experience the best of Oak Bluffs from this exceptional vacation rental. Book your stay today and create lasting memories in this picturesque seaside town on Martha's Vineyard.brbrPlease note that Martha's Vineyard, while beautiful with an abundance of natural landscapes, does have ticks in grassy and wooded areas, so we recommend checking yourself after outdoor activities and taking appropriate precautions to ensure your stay remains enjoyable.brbrThings to KnowbrCheck-in time: 4:00 p.m.brCheck-out time: 10:00 a.m.brAll guests shall abide by our good neighbor policy and shall not engage in illegal activity. Quiet hours are from 10:00 p.m. to 8:00 a.m.brNo smoking is permitted anywhere on the premises.brMaximum occupancy for this unit is 2.brPlease park on the gravel directly in front of the studio, not in the driveway.brHome has a mini split that offers AC and Heat.brbrParking notes: There is free parking available for 1 vehicle.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 25 years of age to book. Guests under 25 must be accompanied by a parent or legal guardian for the duration of the reservation.

Apartment

Charming studio with amazing location near town & beach

Oak Bluffs, Massachusetts, United States

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$267.14

Sea Glen CottagebrbrOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'brbrThis lovely cottage awaits you for your next Martha's Vineyard getaway with the whole family! Featuring a spacious living area, a well-appointed kitchen, and a furnished deck with a convenient outdoor dining area, this home is sure to delight guests of all ages.brbrWhat's nearby:brJust seven miles off the shores of Cape Cod, Martha's Vineyard is famous for its beautiful beaches, myriad lighthouses, and chic eateries. This home offers a central location to everything the island has to offer putting you just minutes away from shops, restaurants, beaches, libraries, hiking trails, and more. And if you're planning on preparing home cooked meals during your stay, you will be right across the street from the fresh vegetables of Norton’s Farm.brbrThings to know:brFree WiFibrFull kitchen with a dishwasherbrThe basement is a separate unit for the owner and they may be present during your staybrbrParking notes: There is free parking available for 2 vehicles.brThis rental is located on floor 1.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.

Cozy getaway in a central location w/ a full kitchen & furnished deck

Oak Bluffs, Massachusetts, United States

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$466.32

Brewster HousebrbrOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'brbrCome and experience Oak Bluff's beautiful beaches, quaint shops, and cozy restaurants at this three-story home!brbrThe exterior of the home boasts new renovations, including a privacy fence surrounding the home with lighting, a conversational floating deck (16x16) in addition to the existing deck, and a lounge set with ample seating and a firepit perfect for gathering with s'mores beneath the stars.brbrOn the first floor of this retreat, you'll find two separate living areas–the living area to your left features a baseboard heat unit, a comfortable sectional sofa in front of a wall-mounted flat-screen TV with cable, Netflix, and a DVD player, a chess table, an air purifier, two large ottoman seats that fold out to new twin-sized beds, a space heater, and even a well-equipped desk! The other living area features even more entertainment with two gaming consoles, videogames, a wall-mounted flat-screen TV, baseboard heat and a space heater, a stereo system, and a sectional sofa–both areas are meant to provide endless entertainment for the entire family.brbrUpstairs is the second and main level of this charming retreat where you'll find the dining area, a small living area, the fully-equipped kitchen, two bedrooms, and one full bathroom. The elegant dining table has a convenient ceiling fan. The small living area is made up of a comfortable armchair and an entertainment center with a flat-screen TV with cable, a sound dock, and a couple of magazines–play your favorite tunes for the group or while cooking! Speaking of cooking, the fully-equipped kitchen will be a delight. Equipped with all the essentials, including a coffee maker, a blender, a dishwasher, and a small island, the chef of the group will have plenty of things to work with when it comes to meal prep.brbrOff the kitchen is the deck equipped with a dining table, additional seating, and a private gas grill for dining alfresco. Both bedrooms on this level have a ceiling fan equipped, while the first bedroom features a wall-mounted flatscreen TV and a handful of books. The full bathroom in the hallway features a convenient tub/shower combo. Upstairs are two other bedrooms and another full bathroom. These bedrooms offer guests the convenience of a ceiling fan and a large flat-screen TV each. The full bathroom is located right in the middle and has a tub/shower combo plus a baseboard heat unit. All bedrooms have been updated for guest comfort. brbrLocated less than one mile from downtown Oak Bluffs, this family-friendly home still provides guests with that much-needed privacy and seclusion. When visiting Oak Bluffs, a must-visit is the Flying Horses Carousel, a Victorian-era merry-go-round and the nation's oldest. Another must-visit, especially if you're a history buff, is The Cottage Museum, which houses period furnishings and photos of the town from the 19th century. Less than one mile as well is East Chop Beach–it's a small, family-friendly beach with great views of Nantucket Sound–and East Chop Lighthouse.brbrTHINGS TO KNOWbrBeach towels are available for guest use.brThis home features free high-speed WiFi, perfect for working from home, distance learning, and streaming.brbrIf you are bringing a dog on your trip, the pet fee is already included in your quote when selecting ‘Yes’ to pets. If you would like to add more dogs, please contact us.brbrParking notes: There is free parking available for 3 vehicles.brbrSecurity camera details: Ring Doorbell facing front drivewaysbrbrbrbrDamage 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.

Wonderful three-story home with lovely decks, firepit, fast WiFi & washer/dryer

Oak Bluffs, Massachusetts, United States

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