Home Vacation Home Rentals By Owner In Edgartown, MA

Showing 160 Of 282 Vacation Rentals
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$1711.83

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Private Vacation Home

Luxurious New Katama Gambrel With Pool

Edgartown, Massachusetts, United States

POINT B EXCLUSIVE - This luxurious Gambrel is designed for the indoor-outdoor Vineyard lifestyle, with a modern layout inside and outdoor living centered around the pool, patio and deck.brbrThe indoor living space includes open Living, Dining, and Kitchen Areas on the first floor. The Living Area has a dramatic two-story vaulted angular ceiling with balcony overlook. Sofa and chair seating is centered around the gas fireplace. The adjacent Dining Area is framed by a wall of glass windows and sliding doors that open out to the deck and pool area. The fully-equipped Chef's Kitchen has a large center prep island/breakfast bar, Viking commercial stainless appliances, and quartz counters.brbrJust off the Living Area is a separate TV/Family Room with large screen TV and sofa seating. A sliding glass door opens out to the pool area. The Primary Bedroom is also located on the first floor. It has a deluxe bath with soaking tub and glass walk-in shower. The other three Bedrooms are upstairs. There is a second Primary Bedroom with deluxe en suite bath, and the two other Bedrooms share a Jack and Jill bathroom with double vanity and glass walk-in shower.brbrThere is a new deluxe Lower Level that greatly expands the living spaces. There is a new Bedroom with private en suite bath. A second TV/Family Room with sofa and chair seating and large screen TV has been added. There is a Gourmet Kitchen and Dining Area for four. The Kitchen has a sink, Viking oven, microwave, dishwasher, plus wine refrigerator, and two refrigerator drawers. The Game Area has a ping pong table, and the Fitness Room has a Peleton bike, treadmill, and weights, plus a large screen TV. brbrOutdoor living revolves around the 14 by 30-foot heated pool. There is a bluestone patio surround with sun lounging area, and a large mahogany deck. There is outdoor lounge and dining seating. Sliding doors from the Dining/Kitchen Area and TV/Family Room open out to the pool area and backyard. A third door enters a Mudroom Area with half bath.brbrFrom its convenient Katama location, downtown Edgartown is about a mile away, and South Beach is about two miles.brbrNOTE: Pool is heated to 80 degrees and included in the rent for July and August. There is a heating surcharge of $250/week in June and September, and $350/week in May and October, if the pool is open.
Bed 5

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Bath 5

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Sleep 12

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Exceptional(31)

$335.1

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Private Vacation Home

Classic Chappy Beach House, big water views, near the water

Edgartown, Massachusetts, United States

You've heard about location, right If you are looking for a cute, clean, place to vacation on Chappy near the water, this is it. Only a handful of homes can claim views and close proximity to Katama Bay like ours. You can also see the ocean over south beach. Just walk down the yard and with a few extra steps you are at the bay. Birds come and go all day from the tidal pond in front of the house. Shaded sitting area, deck, sunsets over the Vineyard. After a day at the beach, you'll never forget taking an outdoor shower in the afternoon sun. Don't worry, the sides are enclosed for privacy. Kids love it here, so close to the beach. There is endless opportunity to play in the tidal stream and pond and look for wildlife. The sand on the beach in front is great to play in or spend a quiet afternoon away from it all. Fisherman will also appreciate the lighted outdoor filet table. The house is perfectly positioned for afternoon sun, and a cool breeze off the ocean and bay. Sunsets are beautiful, right from the deck and dining room. The kitchen and bathroom were recently updated. Ask about possible use of kayak, paddle boards and bikes. Feel free to contact me with questions before requesting a reservation. August renters please ask me about my transferrable Steamship auto reservations !!! No extra cleaning fee!
Bed 4

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Bath 1

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Sleep 8

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Exceptional(2)

$1447.19

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Private Vacation Home

EDGARTOWN PRIVACY WITH A HEATED POOL AND CENTRAL AC

Edgartown, Massachusetts, United States

Welcome to 36 Hamblen Way - Your Edgartown Retreat. Our mission is simple, to provide you and your family with an unforgettable Vineyard experience rooted in comfort, privacy, and natural beauty.brbrTucked away on the outskirts of historic downtown Edgartown, this home offers a rare blend of space and seclusion, making it a true gem in one of the island’s most sought-after locations. Surrounded by mature trees and open sky, the property connects you to nature while keeping you close to the charm and amenities of town.brbrInside, you'll find four thoughtfully furnished bedrooms, two full bathrooms, and central air conditioning throughout—ensuring a cool and comfortable stay even on the warmest summer days. With its southern exposure, sunlight pours into most rooms throughout the day, creating a bright and welcoming atmosphere.brbrNew as of Summer 2023, our 40' x 20' in-ground pool can now be enjoyed heated at your request, extending your poolside fun well into the evening hours.brbrWhether you're lounging poolside, gathering with loved ones in the common spaces, or unwinding in one of the serene bedrooms, there's something for everyone to enjoy. And yes—we’re pet-friendly, because no family vacation is complete without your four-legged companions.brbrLastly, we believe in true Vineyard hospitality. Our local caretaker is always nearby to ensure your stay is smooth and stress-free, offering help should any needs arise.brbrPlease reach out with any questions. We’d love to hear from you.
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Bath 2

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Sleep 8

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$5812.22

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Private Vacation Home

Sandpiper Fields Luxury Field Club Home Near South Beach on Martha’s Vineyard

Edgartown, Massachusetts, United States

Discover an extraordinary getaway at this breathtaking Martha’s Vineyard luxury home, located in the prestigious Edgartown Field Club. Just one mile from historic Edgartown and some of the island’s most stunning beaches, this property offers elegance, privacy, and convenience for an unforgettable vacation. brbrProperty Features brbrMain House br- Five spacious bedrooms, each with a private en suite bathroom, ensuring comfort and privacy. brbrCarriage House br- A charming one-bedroom, one-bathroom suite located above a two-car garage, ideal for guests or staff. brbrEntertainment Paradise brPerfect for hosting or unwinding, this property boasts: br- Elegantly furnished living spaces. br- A high-quality sound system for music and entertainment. br- Multiple fireplaces for cozy evenings. br- Expansive patio, decks, and balconies for seamless indoor-outdoor living. br- A luxurious pool and spa, added in 2013, perfect for relaxation. brbrImpeccable Landscaping brMeticulously maintained grounds enhance the serene and picturesque ambiance, blending harmoniously with the natural beauty of Martha’s Vineyard. brbrThis home is a haven of relaxation and indulgence, perfectly designed to make every stay special. brbrAdditional Information brbrPhotography brImages were taken this fall with an iPhone 15 Pro Max under challenging light conditions. Pools were covered, but the photos still highlight the home’s undeniable charm and appeal. brbrOwner Dedication brThe owner takes exceptional care of the property, consistently updating it with high-end furniture and thoughtful touches to ensure a luxurious experience. brbrAccuracy brWe strive to provide accurate details, though minor updates or changes may occur. Feel free to reach out with questions—I've personally visited and can confirm the home’s extraordinary quality. brbrRental Policies brbrSecurity Deposit brA refundable security deposit of $5,000 or 10% of the rental rate, whichever is higher, is required. brbrPet-Friendly Accommodations br- Well-behaved pets are welcome! br- Pet fee: $2,500, with an additional $2,500 security deposit. brbrCleaning Fees br- Minimum cleaning fee: $1,250 per stay, covering linens and ensuring the home is immaculate. br- Multi-week bookings: Require an interim cleaning fee of $1,250. brbrDon’t miss the chance to experience unparalleled luxury and comfort at this stunning Martha’s Vineyard retreat.** brbrBook your stay today** and create memories to treasure for a lifetime!
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Bath 4

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Sleep 10

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$9495.23

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Private Vacation Home

Luxury Field Club Compound with Pool and Barn

Edgartown, Massachusetts, United States

This Martha’s Vineyard compound is situated in the exclusive Edgartown Field Club, just a mile away from both historic Edgartown and some of the finest beachfront on the island. The property has two generous master suites and then three additional bedrooms for kids/guests/ The property features a main house, a Carriage House, and a pool house. with five generously sized bedrooms, each featuring en suite bathrooms. There is also a large carriage house that has a one-bed/one-bathroom suite above a massive 1st floor, complete with two bars and an entertainment area. brIt is an entertainer paradise; amenities abound, including luxuriously decorated living spaces, a sound system, multiple fireplaces, a patio, decks and balconies, and a luxurious pool and spa added in 2013. The landscaping is meticulously maintained, and the property offers unrivaled indoor and outdoor living.brThe spaces are large and well-appointed. You will not want to leave this amazing residence.brbrA few words about this listing.brI took all of the photographs with my iPhone 15 ProMax this fall. The light was not great, and the pools (if the property has one) were covered. I tried to get a professional photographer to take them but it was hard to do and coordinate a time when these properties were empty as they are quite busy. brSome of the beds are not even set up yet. This is indicative of how much this owner cares for these properties (we represent five on them) that he is always fixing them up, adding heavy furniture, and making everything super nice. brWhile we have attempted to confirm every detail, there is the possibility that we might have missed something. These are new listings and we are only too human.brIf you have any questions at all about the booking please feel free to ask me about them. I have personally visited each one, and they are all amazing. br brThe Security Deposit is $5,000 or 10% of the rental rate, whichever is higher brThis property is now allowing well-behaved petsbrThe pet fee is $2,500 with an additional $2,500 security depositbrThe cleaning fee to maintain this large compound is based on an estimate of at least $1,250 per stay. This includes all linens with each bed made and the home presented as immaculate. brA full interim cleaning fee of $1,250 is required for multi-week bookings.
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Bath 5

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Sleep 8

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Exceptional(4)

$989.49

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Private Vacation Home

Downtown Edgartown Historic District. Walk to town and harbor.

Edgartown, Massachusetts, United States

This house offers 3 spacious bedrooms with convenient one floor living. The large living room features comfortable furnishings, a large window provides wonderful light, custom built in cabinets and a large TV with high definition cable and WiFi. brbrThe bright kitchen has plenty of cabinet and counter space, is well equipped and features new granite counters and appliances. The eating area seats six and has a tv. There is a half bath off of the kitchen. The living room and kitchen each have separate air conditioning. The dining room features custom cabinetry and a large dining table. brbrThe primary bedroom is bright and airy and has a queen-sized bed, two closets and a TV. Bedroom number 2 has two twin beds and three closets. Bedroom number 3 has a queen bed and one closet. All bedrooms have linens and air conditioners with separate controls. The full tiled bath is equipped with new fixtures and all towels. brbrOutside in the quiet and private back yard, there is a patio with propane grill, outdoor eating and seating. There is an outdoor shower just off of the patio.brThe location in the historic district is a convenient walk to downtown shopping and restaurants, harbor, and offers easy access to bikepaths. The attached garage provides shelter for your bikes and beach gear. There is a clothes washer and dryer in the attached garage, and an additional washer and dryer in the basement.brbrBeach towels, beach chairs and a cooler are included.brbrThe location of this house allows for a short 5–10 minute stroll to downtown and the harbor. The are many restaurants and shops within walking distance. There's no need to spend time looking for a parking space when venturing out to downtown Edgartown.brbrTransferrable car tickets for the ferry are available for the week of July 18 - July 25, 2026
Bed 3

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Bath 1

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Sleep 6

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Exceptional(1)

$1516.89

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Private Vacation Home

Modern Saltbox in Edgartown Village

Edgartown, Massachusetts, United States

Gorgeous, coastal chic decor provide comfort in this modern 4 bedroom home only 5 blocks to Edgartown Village and 2.5 miles to South Beach! Walk, bike or a quick drive to enjoy the best of the Vineyard. This home is truly inviting and fully equipped with all you need for a perfect stay. The layout and decor are playful yet practical, with second lounge area and work niche upstairs. The three season porch offers a breezy lounge area overlooking the gas fire pit, outdoor dining and backyard retreat. brbrThis exceptional house is the perfect location for all your Vineyard adventures. Just a stone's throw from Main Street in Edgartown, you can easily explore the shops, galleries, and amazing restaurants or simply soak up the stunning Edgartown harbor. Pedal your bike to South Beach, less than three miles away, or State Beach, a little under two miles away. Even closer, you'll find the lovely Fuller Street Beach with views of harbor boats, Chappy and Edgartown Light. brbrDespite its classic Edgartown exterior, this house boasts an open floor plan with breathtaking coastal chic decor and luxurious furnishings. The kitchen and dining area flow seamlessly into a three-season room and terrace with a cozy firepit for those cool island nights. The beautifully landscaped yard also features an enclosed outdoor shower, perfect for rinsing off after a long day at the beach. The bedrooms are perfectly spaced, with two per floor and a comfortable lounge/TV area plus a convenient work niche on the second floor. Air conditioning is provided by a combination of central air on the first floor, and split units in the primary bedroom and third bedroom.brbrSip morning coffee by the fire pit and evening cocktails on the porch, this house is also a perfect retreat space for your long weekend getaway with friends. While summer is often the draw, spring and autumn are also wonderful for a Vineyard excursion. We offer shorter stays during the 'off season' - bike, hike, relax and simply soak in the salt air.brbrOverall, this superior house is a true gem, perfectly located for all your Vineyard activities, offering a luxurious and stylish retreat when you need a break from the island's hustle and bustle.
Bed 4

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Bath 3

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Sleep 8

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Exceptional(4)

$622.19

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Private Vacation Home

Home Away From Home

Edgartown, Massachusetts, United States

This wonderful Cape is warm and inviting with beautiful hardwood floors and an open floor plan. It's located near a bike path and bus line, providing easy access to all the beaches towns on the island. The home is on a dead-end street with no thru vehicle traffic, perfect for privacy and quiet. If you take a short walk to THE BLVD, you can see the picturesque Sengekontacket Pond, known as Sengie Pond by the locals, where you can swim, fish, or kayak.brbrThere are three spacious bedrooms, queen, king, and a twin bedroom. Upstairs has a newly renovated bath and shower. The queen and king bedroom are equipped with A/C, ceiling fan and Tv's. The first-floor bedroom has twin beds, across from the newly renovated bath and shower, also equipped with A/C, ceiling fan and TVbrbrThe main level has a TV and is fully air-conditioned. The kitchen has all of the appliances you will need for your family and also a breakfast bar with comfortable seating. In the dining area, there is a sliding glass door that leads outside to a spacious wrap around deck equipped with a gas grill and ample sitting. Recently added is a private outdoor shower with a changing area. The lower level was recently renovated into a family room and has TV with additional sleeping area.brbrThe home is convenient to local beaches, shopping, and downtown Edgartown. Linens and towels are provided. Beach chairs are available. Please no smoking or pets.brbrbrbrbrbrbr
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Sleep 8

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Exceptional(4)

$1515.13

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Private Vacation Home

Private - Walk to Downtown Edgartown/Bike to South Beach. Ferry Tkts Available.

Edgartown, Massachusetts, United States

This bright and charming home is beautifully set on over an acre of meadow like property, yet only a 10 min. walk to the shops and restaurants in Edgartown. Located on a quiet lane, it is a 10 minute drive and 15 minute bike ride to beautiful South Beach and a bike ride to the iconic Morning Glory Farm. This home is ideally located - a little slice of Chilmark, set in Edgartown.brbrThe private, bucolic setting is surpassed only by the charming beachy ambiance of the home itself. It has a large bright living room with fireplace and TV, a kitchen with a Sub-Zero Refrigerator, wine cooler and granite island, a sunny breakfast room with bay window, and a cozy sunroom with cathedral ceilings, TV and french doors that open onto the spacious deck. On the lower level there is a large finished basement, complete with TV, a work station and an alcove with a ping pong table (or the inflatable queen mattress for 2 additional guests). brbrIt has a first floor, primary king bedroom with cathedral ceiling, built-in desk, oversized walk-in closet, private bath and TV. On the second floor it has 2 additional bedrooms, one with a queen size bed and a twin bed and the other with a full size bed and a twin bed, with a full bathroom on the second floor as well. An additional bedroom is on the lower level with a queen sized bed. There is a third full bathroom on the main floor, as well as a spacious outdoor shower, with changing room.brbrThrough the French doors of the sunroom is the spacious, sunny deck providing room and furnishings for grilling on the Weber grill and dining, or simply relaxing on the beautiful cushioned teak furniture. You can enjoy all of this, while looking out over the beautiful spacious, open property perfect for lawn games and experiencing perfect privacy. brbrThe detached shed provides bikes, beach chairs, boogie boards, coolers and more … for your enjoyment. brbrThis home provides the relaxing and inviting lifestyle one hopes to find vacationing on Martha’s Vineyard.
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Bath 3

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Sleep 10

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Exceptional(37)

$1043.12

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Private Vacation Home

Private forested oasis near town and beach, large deck - 54

Edgartown, Massachusetts, United States

Near beaches, shops, and trails, these comfortable homes are ideal for families, couples, friends, or work trips. Highlights include:br • AC, Wi-Fi, TVs, and washer/dryerbr • Ample parking and bikes to borrowbr • Short walk to the bus stopbr • Direct access to a sandy walking pathbr • Kid-, dog-, and adult-friendly setupbr • Linens, beach towels, and a fully stocked kitchen includedbr • Large deck, grill, and outdoor showerbr • Spacious lawn, volleyball, and beach toysbr • 24/7 game room with ping pongbrbrWelcome to Martha’s Vineyard Vacation Homes in Edgartown. Set on a peaceful two-acre property, we offer two identical, well-appointed 3-bedroom, 2-bath homes, each on its own private half-acre. Located just 1.5 miles from State Beach, Edgartown Harbor, and Katama Beach.brbrHome Featuresbr • Central air conditioningbr • Free Wi-Fi and TVsbr • Washer and dryerbr • Fully equipped kitchen (dishwasher, microwave, cookware, coffee maker, blender)br • Hardwood floors, cathedral ceilings, and skylightsbr • Linens and towels includedbr • Large wraparound sun deck with seating, picnic tables, and charcoal + propane grillsbrbrSleeping Arrangementsbr • Upstairs: King primary suite with private bathbr • Downstairs: Two bedrooms, each with two queen bedsbr • Living room: Spacious skylit area with two futonsbrbrOutdoor & Shared Amenitiesbr • Large lawn and open fieldbr • Outdoor showerbr • Volleyball and beach toysbr • 24/7 game room with ping pongbr • Bikes available for guest usebrbrClean, Comfortable, and Well-MaintainedbrWe take pride in providing a clean, fully equipped home. Backup small appliances are kept on hand to ensure a smooth and comfortable stay.brbrFamily-Owned & OperatedbrHosting guests since 1973, our family-run property is cared for with the help of trusted local families. We’re committed to providing a welcoming and reliable Vineyard experience.brbrLocation Highlightsbr • Direct access to Pennywise Path, a scenic sandy trail leading to Morning Glory Farmbr • Short walk to the (seasonal) bus stopbr • Easy access to beaches, downtown Edgartown, and island attractionsbrbrGood to Knowbr • Check-in: 4 PM | Check-out: 10 AMbr • Typical minimum stays: 3–4 nights (7 nights in peak summer)br • Utilities includedbr • Massachusetts short-term rental tax (9.7%) appliesbrbrPet & Family FriendlybrWell-behaved dogs are welcome, and the spacious lawn is perfect for kids and pets to play. *Pet fees may applybrbrEnjoy a private, relaxed stay with the comforts of home in a beautiful Vineyard setting—perfect for making lasting memories.
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Sleep 10

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Exceptional(57)

$726.05

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Private Vacation Home

Spacious 4BR+ Katama Home-Edgartown South Beach Area

Edgartown, Massachusetts, United States

Enjoy the ultimate Martha’s Vineyard getaway in this beautifully decorated, contemporary home—ideally located just 1 mile from iconic South Beach and 3 miles from historic downtown Edgartown. Perfect for families or groups, this spacious home features an open-concept second floor with soaring cathedral ceilings, a bright and airy dining area, fully equipped kitchen, large family room, and a separate TV room/den.brbrStep outside onto the expansive South-facing second floor deck, complete with dining furniture and cushioned lounge chairs—then head up the stairway to the spectacular rooftop Widow’s Walk, where you can unwind with sunset views or stargaze under Vineyard skies.brbrThe kitchen is fully equipped and offers ample counter space, a dishwasher, microwave, and all the essentials. The 2nd floor TV room/den includes a smart flat-screen TV, DVD player, and a privacy door, and doubles as an extra sleeping area with a pull-out full-size sleeper sofa.brbrThis home offers flexible sleeping arrangements:br • Primary bedroom: Queen bed + private full bath br • Second bedroom: Queen bedbr • Two additional bedrooms: Each with a full-size beds and shared full bathbr • Bonus room (2nd floor): Two sub-twin beds (30” x 74”) with comfortable memory foam mattresses—great for childrenbr • TV den: Pull-out full-sized sleeper sofabrbrAdditional amenities include:br • Central air conditioning & heatingbr • High-speed wireless internetbr • Washer and dryerbr • Eight adult and kids bicycles for guest use (see photos) • great bike paths nearby to beach and downtown Edgartown.br • Nine beach chairs and multiple umbrellasbr • Gas grill, hammock, and two outdoor picnic tablesbrbrEverything you need for a memorable island vacation is right here—comfort, convenience, and classic Vineyard charm. Also located near the Katama airport and diner (great for breakfast or taking an exciting bi-plane ride around the island).
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Bath 2

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