Classifieds: Vacation/Summer Rentals

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  • Classic Oak Bluffs Victorian waterfront cottage
    Booking for summer 2019 weeks

    You'll feel like you're up-Island with the quiet, and the water, water everywhere views, but it's only a 5-minute walk to the Inkwell, and 10 minutes to town, ferries, shopping, galleries. Bike and hiking paths right out the door; paddle your kayak out the front door to great fishing; walk to nearby parks and playgrounds. Four bedrooms all with high ceilings and pond and ocean water views, two full baths plus huge outdoor shower. A great house for readers: lots of private nooks and crannies, expansive front porch. Large yard, wood-burning fireplace, playroom in basement, brand new kitchen appliances. Dog-friendly. Some June and July weeks still available, random off-season weeks/long weekends. See photos and availability here: bit.ly/FarmPondHouse or text or call 508-801-6435.

  • Katama House

    3 bedrooms,1-1/2 bath, Sleeps 6, laundry, kitchen/dishwasher, living/dining room, outside shower. 1-mile to beach. May to Labor Day. $12,000. 508-627-9108/508-737-9517.

  • OAK BLUFFS

    1900 Oak Bluffs Victorian. Ten minute walk to Nancy’s restaurant/downtown OB and 1/2 mile walk to Jetty beach in East Chop. The house was purchased empty in 2018 so all furnishings are new and the house is freshly painted. On the second floor, there are 3 bedrooms and a full bathroom, which connects to hall and master bedroom. Two bedrooms include queen beds and one bedroom includes a full bed and a set of twin bunks. On the first floor, there is a large living room connected to a sleeper den, which provides great common area for playing board games and relaxing after a day at the beach. The living room includes a 50” tv with cable and x-box, which can be used as a dvd. Small bathroom with shower on the first floor connects to the kitchen which has an eat in kitchen, with seating for 6. Great covered front porch for your morning coffee or a glass of wine under the outdoor lights. The gas grill is on the back of the house in a small yard. There is also a driveway on the back of the house for off-street parking for one car.
    There a mini-split air conditioner in the stairway that cools most of the first floor and the the first bedroom. The other two bedrooms and kitchen have window AC units. The sleeper den has a ceiling fan. Many amenities (AC, dishwasher, washer/dryer, 50” high definition cable TV, Internet, BBQ grill, beach chairs, two bikes, board games, puzzles, new furniture.) House is located across from the bus stop on the main road between Vineyard Haven and OB providing easy access to the rest of the Island. Come and enjoy your Martha’s Vineyard summer vacation! OB536 Weekly Rate $4,500. Karen M. Overtoom Real Estate 508-693-7832. www.overtoommv.com. http://www.overtoommv.com/marthas-vineyard/vacation-rentals/Oak-Bluffs/property/?pid=451

  • EDGARTOWN

    Waterfront with Dock and AC Overlooking Katama Bay. Private Beach, Waterfront, and Dock!! Spend your days looking at beautiful Katama Bay. Dock your boat or relax at your private beach. This large Classic Vineyard Home sleeps 10, has two living rooms, protected porch area and a really great front yard leading to the beach. The location is close to South Beach and downtown Edgartown. ED328 Weekly Rate $12,000. Karen M. Overtoom Real Estate 508-693-7832. www.overtoommv.com. http://www.overtoommv.com/marthas-vineyard/vacation-rentals/Edgartown/property/?pid=1463

  • EDGARTOWN

    Relax and enjoy this beautiful, immaculate Katama home centrally located 1 1/2 miles to South Beach and downtown Edgartown. This immaculate 3 bedroom (with extra loft sitting area) home has been equipped specifically with all the vacation comforts you'll need. It features beautiful hardwood floors, carpeting, an open floor plan, vaulted ceilings w/beams, skylights, bonus loft area with additional TV and DVD/VCR player, internet Amazon Prime TV and Sling TV and a private yard and deck with patio furniture and a gas grill. Enjoy wifi access, a Smart flat panel LED TV with DVD player and great stereo in the living room. Air conditioning units throughout the house. Super location in private and quiet Edgartown Estates off of popular Herring Creek Road and the bike path in Katama 1 1/2 miles to go to South Beach or Edgartown. Limited number of ferry tickets available. ED327 Weekly Rate $3,100. Karen M. Overtoom Real Estate 508-693-7832. www.overtoommv.com. http://www.overtoommv.com/marthas-vineyard/vacation-rentals/Edgartown/property/?pid=1469

  • EDGARTOWN

    This updated contemporary is located in Katama area and a short bike ride to South Beach. There are 4 bedrooms, 1 down and 3 up, and a beautiful kitchen/dining which opens to a large living room. The house has a nice deck on the front and owners have added a deck off the kitchen as well.There is a wonderful screened porch off living room. A very quiet location and easy ride into town. ED321 Weekly Rate $3,500. Karen M. Overtoom Real Estate 508-693-7832. www.overtoommv.com. http://www.overtoommv.com/marthas-vineyard/vacation-rentals/Edgartown/property/?pid=91

  • EDGARTOWN

    Wonderful 4 bedroom home off of Fuller St. This privately set home has a wonderful view and is just steps from the beach. The attention to details is incredible!! A very short walk to downtown to enjoy all the activity. The setting could not be better. The home is such a delight. There is an outdoor shower, patio, sunroom, private patio, large spacious rooms, commercial grade stove, jetted tub. You name it and the owners have provided it. This is what Vineyard vacations are all about. ED320 Weekly Rate $8,000. Karen M. Overtoom Real Estate 508-693-7832. www.overtoommv.com. http://www.overtoommv.com/marthas-vineyard/vacation-rentals/Edgartown/property/?pid=401

  • OAK BLUFFS

    Sweet three bedroom gingerbread house right in the heart of downtown Oak Bluffs. Walking distance to Ink Well Beach, shopping and ferry. Equipped with beach umbrella, wagon and beach toys. Lovely front porch and back deck complete with outside shower! This quaint cottage is perfect for your relaxed summer getaway! OB507 Weekly Rate $3,000. Karen M. Overtoom Real Estate 508-693-7832. www.overtoommv.com. http://www.overtoommv.com/marthas-vineyard/vacation-rentals/Oak-Bluffs/property/?pid=410

  • OAK BLUFFS

    1900 Oak Bluffs Victorian. Ten minute walk to Nancy’s restaurant/downtown OB and 1/2 mile walk to Jetty beach in East Chop. The house was purchased empty in 2018 so all furnishings are new and the house is freshly painted. On the second floor, there are 3 bedrooms and a full bathroom, which connects to hall and master bedroom. Two bedrooms include queen beds and one bedroom includes a full bed and a set of twin bunks. On the first floor, there is a large living room connected to a sleeper den, which provides great common area for playing board games and relaxing after a day at the beach. The living room includes a 50” tv with cable and x-box, which can be used as a dvd. Small bathroom with shower on the first floor connects to the kitchen which has an eat in kitchen, with seating for 6. Great covered front porch for your morning coffee or a glass of wine under the outdoor lights. The gas grill is on the back of the house in a small yard. There is also a driveway on the back of the house for off-street parking for one car.
    There a mini-split air conditioner in the stairway that cools most of the first floor and the the first bedroom. The other two bedrooms and kitchen have window AC units. The sleeper den has a ceiling fan. Many amenities (AC, dishwasher, washer/dryer, 50” high definition cable TV, Internet, BBQ grill, beach chairs, two bikes, board games, puzzles, new furniture.) House is located across from the bus stop on the main road between Vineyard Haven and OB providing easy access to the rest of the Island. Come and enjoy your Martha’s Vineyard summer vacation! OB536 Weekly Rate $4,500. Karen M. Overtoom Real Estate 508-693-7832. www.overtoommv.com. http://www.overtoommv.com/marthas-vineyard/vacation-rentals/Oak-Bluffs/property/?pid=451

  • CHILMARK

    Chilmark Rental Close to West Tisbury Center! A large rambling old family home where memories are made. The extended family can all join in a vacation full of laughter and play. The grounds are full of places for hide-and-go-seek. Privately set on Middle Road in the woods yet bathed in sunlight. The house has a string of bedrooms for all the family members to find their place. A great old house like they don't make any more. CH229 Weekly Rate $4,800-$9,000. Karen M. Overtoom Real Estate 508-693-7832. www.overtoommv.com. http://www.overtoommv.com/marthas-vineyard/vacation-rentals/Chilmark/property/?pid=310

  • CHILMARK

    Water views, 3 acres and stone walls. At the end of a lane, enjoy the privacy offered by 49 acres of conservation land complete with walking trails. This house is a short distance from Lucy Vincent beach, as well as from Menemsha and Squibnocket. This spacious four bedroom, 2 bath home has an expansive rear deck that offers panoramic water views. The main level offers an open kitchen and large living room complete with fireplace. An entire wall is floor to ceiling glass with French doors opening onto a large deck. All of the rooms on this floor offer stunning views, including the Master bedroom. The first level features a large family room and three ample sized bedrooms. Black Point Beach Key included with property!!! CH206 Weekly Rate $5,500. Karen M. Overtoom Real Estate 508-693-7832. www.overtoommv.com. http://www.overtoommv.com/marthas-vineyard/vacation-rentals/Chilmark/property/?pid=1470

  • CHILMARK

    Farm House in Menemsha with North Shore Views! Style, warmth, and comfort define this delightful farm house in Menemsha with a water view to the Vineyard Sound. The property is spacious and private. Features include a newly constructed private pool. There is a tennis court shared by the occupants of the neighboring barn. The house comes with a key to a beach in Aquinnah on Moshup trail and a shared key to Quansoo Beach. It is also possible to purchase stickers to Lucy Vincent and Squibnocket Beaches at Chilmark Town Hall for a variety of choice beaches for your vacation. CH233 Weekly Rate $11,000. Karen M. Overtoom Real Estate 508-693-7832. www.overtoommv.com. http://www.overtoommv.com/marthas-vineyard/vacation-rentals/Chilmark/property/?pid=313

  • EDGARTOWN

    Vacation by the beach in a relaxed contemporary home offering fabulous panoramic views of Edgartown Harbor, Chappiquidick, Katama Bay and South Beach. Our Katama Bay home is located off of Edgartown Bay Road at the quiet cul-de-sac,close to the beaches and boat launch access. For those who love the ocean breezes and sandy beaches, there is great sunbathing, windsurfaing, sailing, boating and shell fishing, all within view. ED323 Weekly Rate $4,800-$6200. Karen M. Overtoom Real Estate 508-693-7832. www.overtoommv.com. http://www.overtoommv.com/marthas-vineyard/vacation-rentals/Edgartown/property/?pid=102

  • WEST TISBURY

    This stunning sanctuary offers a unique balance of simplicity and sophistication. There is a lot of room for family and friends to enjoy both indoors and out. Nestled about midway between Tisbury and West Tisbury, here you will find yourself close to two of Martha's Vineyard's town centers. Enjoy ping pong in the retro style game room or a fire in the fire pit. This slice of heaven on earth is sure to give you a vacation you will never to forget. WT121 Weekly Rate $7,000. Karen M. Overtoom Real Estate 508-693-7832. www.overtoommv.com. http://www.overtoommv.com/marthas-vineyard/vacation-rentals/West-Tisbury/property/?pid=461

  • CHILMARK

    A comfortable contemporary home that includes a key to private beach is ideal for laid-back Vineyard living, or elegant entertaining with both ocean and hillside views. The open floor plan for the common areas bring the outdoors inside with spectacular sunshine and sweeping views. Privacy in the living quarters, both upstairs and downstairs, allow for downtime and quiet moments alone or with a group. CH201, Weekly Rate $8,500. Karen M. Overtoom Real Estate 508-693-7832. www.overtoommv.com. http://www.overtoommv.com/marthas-vineyard/vacation-rentals/Chilmark/property/?pid=453

  • OAK BLUFFS
    EAST CHOP LOCATION!!

    Located across from the historic Baptist Temple Town Park. This charming 1885 Victorian cottage is original to days gone by and a significant part of the Vineyard Highlands. Six bedrooms and two full bathrooms allow for friends and family to visit along with a cozy, bright vintage kitchen. This is a house of distinctive "Carpenter Gothic" construction built by the architect G.A. Rice on one of the highest points of Oak Bluffs.There are 2 bedrooms upstairs, separated by a small common area that can be used as a bedroom as well. Separate stairways lead directly to both. Bathrooms are located on the first floor along with 3 more bedrooms. Oak Bluffs is a strolling paradise, and this location is only a short walk to the beaches, ferry, bike path, restaurants, harbor activity and public transportation. The closest beach is a 10 min walk or 5-minute bike ride. The street is full of longtime residents who live there seasonally. Please be mindful of late night noise. Chromecast can be used with television. OB519 Weekly Rate $4,800. Karen M. Overtoom Real Estate 508-693-7832. www.overtoommv.com. http://www.overtoommv.com/marthas-vineyard/vacation-rentals/Oak-Bluffs/property/?pid=432

  • Edgartown Summer Rental

    3 bedroom, 2 baths, spacious summer rental near Dodger's Hole. $2400/week. Large deck, outdoor shower. Pets possible. Pictures available. Call Bob at 917-442-3896.

  • West Tisbury

    Set on 12 acres of peaceful woods, meadows, stone walls and its own pond, this charming 18th Century 4-bedroom farmhouse and 3-bedroom rustic barn sleeps 12 and is perfect for larger groups wanting peace and tranquility all within walking distance to private swimming beaches. The setting, on exclusive Seven Gates Farm, offers miles of sandy walking trails through open fields and woodlands, and two miles of pristine calm water beaches, perfect for swimming and boating. A bucolic world of its own and yet shops and restaurants in West Tisbury are only 7 minutes away. WT120, Weekly rental $7000 Karen M. Overtoom Real Estate 508-693-7832 www.overtoommv.com.
    http://www.overtoommv.com/marthas-vineyard/vacation-rentals/West-Tisbury/property/?pid=407.

  • Edgartown

    Enjoy the pool with this stunning custom designed and professionally decorated Tri Level contemporary home with open floor plan. Once inside you will be captivated by the dramatic open spaces, soaring ceiling and walls of glass. Located in a high end neighborhood within walking distance to South Beach. The yard is beautifully landscaped and has an 18x40 heated saltwater pool with blue stone surround and lounge chairs and fire pit. With three levels, multiple gathering spaces, four bedrooms and 4 1/2 baths is the perfect spot for large families. Three bedrooms are master suites with private baths. You will truly love this wonderful home for your next summer vacation on the Vineyard!! ED310, Weekly rate $13,500. Karen M. Overtoom Real Estate 508-693-7832 www.overtoommv.com.
    http://www.overtoommv.com/marthas-vineyard/vacation-rentals/Edgartown/property/?pid=425.

  • Chilmark

    Chilmark Cottage Perfection!!! You will love this quaint Vineyard Style Cottage that has been meticulously designed to include all the amenities one could imagine. This vintage charmer really boasts a lot of Style. Inside you will find really beautiful hardwood floors, a fully equipped kitchen, and a storybook bedroom complete with wonderful linens. This home is one of the most perfect spots to spend your vacation on the Vineyard. Also, renters have access to the private beaches of Lucy Vincent and Squibnocket. This home is available for weekly winter rentals.
    CH202, $2500 for summer weeks. Call us for winter weekly rates. Karen M Overtoom Real Estate 508-693-7832 www.overtoommv.com.

    http://www.overtoommv.com/marthas-vineyard/vacation-rentals/Chilmark/property/?pid=452

  • West Tisbury

    Large spacious home with open concept living and dining area. This house has gorgeous hardwood floors throughout, separate media room, and loads of natural sun light. It also features an exceptionally large master bedroom with en-suite bath, and private deck. There is plenty of grassy yard, complete with hammock and outdoor shower.
    Lambert's Cove Beach Access.
    WT117, Weekly rate: $3,000. Karen M. Overtoom Real Estate 508-693-7832. www.overtoommv.com.

    http://www.overtoommv.com/marthas-vineyard/vacation-rentals/West-Tisbury/property/?pid=422.

  • West Tisbury

    This lovely new build house features 3 bedrooms, and 3 bathrooms. There is a full gourmet kitchen, open to the dining, living and patio area. French doors off the living area open up to a beautiful blue stone patio complete with breath taking water views. All three bedrooms are located on the upstairs level including the master suite.
    Lambert's Cove Beach Access.  WT107, Weekly rate: $5,750. Karen M. Overtoom Real Estate 508-693-7832. www.overtoommv.com.
    http://www.overtoommv.com/marthas-vineyard/vacation-rentals/West-Tisbury/property/?pid=424.

  • West Tisbury

    Beautiful bright sunny home with open concept living. Main floor features a gourmet kitchen with stainless appliances, breakfast bar and formal dining table to seat 10. Large glass sliders open up to expansive views of the deck, pool and pasture beyond. The finishing touch is a lovely heated pool with large deck, mature plantings, and sweeping views of the pasture. Lambert's Cove Beach Access. WT104, Weekly rate: $11,500. Karen M. Overtoom Real Estate 508-693-7832. www.overtoommv.com.
    http://www.overtoommv.com/marthas-vineyard/vacation-rentals/West-Tisbury/property/?pid=424.

  • Aquinnah

    Watch the boaters come and go, the sunset in the evening and feel the ocean breezes from this post & beam style 3 bedroom home. Open living spaces offer comfortable living that include living, dining and kitchen that open to a wide deck with Vineyard Sound views looking out toward the Elizabeth Islands. The master bedroom is located on this level while the two guest bedrooms are on a lower level with an additional family room. AQ605, Weekly rate: $3,500. Karen M. Overtoom Real Estate 508-693-7832. www.overtoommv.com.
    http://www.overtoommv.com/marthas-vineyard/vacation-rentals/Aquinnah/property/?pid=235.