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.

  • CHARMIMG EDGARTOWN CAPE

    Set on nicely lanscaped lot with tennis in the quiet neighborhood community of Island Grove. Screened-in porch, large back deck, BBQ, outdoor shower, W/D, fully equiped kitchen in open layout.  3 bedrooms, 3 bath which includes one large master suite. $3500/week.  Call or text for photos and information. 774-563-8177.

  • CHILMARK

    A modern summer retreat is nestled high on a knoll off North Rd in picturesque Chilmark. Here in this stunning contemporary ranch you will find the upmost in Luxury. Each room is exciting, charming and has a simplistic yet artistic style. The entire house is accented with beautiful light pine flooring that pairs perfectly with the expansive main room. On each side of the main living area are two one bedroom en suite areas that offers privacy between the two bedrooms. Each bedroom has a queen bed and a twin bed affording the possibility of sleeping six people. This home is set on a hill that provides privacy and tranquility. Feel free to use the wonderful outdoor shower or relax in the backyard. You are welcome to use the private Chilmark beaches. Or take a short drive to enjoy the picturesque Menemsha fishing village and grab a lobster roll while watching the brilliant sunset.
    Ch248, Weekly rate: $3,200. Karen M. Overtoom Real Estate 508-693-7832. www.overtoommv.com.
    http://www.overtoommv.com/marthas-vineyard/vacation-rentals/Chilmark/property/?pid=448

  • Edgartown

    This gorgeous waterfront home is well equipped with gourmet kitchen, stone fireplace, numerous
    sitting areas, and multiple decks each with water views over the Edgartown Harbor. Both the main
    and upper level have beautiful master suites and also washers and dryers. Easy access to downtown
    Edgartown, South Beach and the Bike Path. A lush green path leads you down to the dock and boat house, where there is also a mooring for larger boats. ED317, Weekly rate $25,000. Karen M. Overtoom Real Estate 508-693-7832 www.overtoommv.com.
    http://www.overtoommv.com/marthas-vineyard/vacation-rentals/Edgartown/property/?pid=359.

  • 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 farm house features luxurious accommodations. Four of the bedrooms have en-suite
    bathrooms, three of which include a bathtub and shower. All bedrooms are equipped with a split air conditioner. There is a formal living room as well as a family room with TV and additional dining table to eat or play games. Old wooden beams give the property a historic old world feel with all the modern conveniences. You can lounge on the patio taking in the mature landscaping. Lambert's Cove Beach Access. WT111, Weekly rate: $5,700. Karen M. Overtoom Real Estate 508-693-7832. www.overtoommv.com.
    http://www.overtoommv.com/marthas-vineyard/vacation-rentals/West-Tisbury/property/?pid=392

  • West Tisbury

    This three story home is located in a very desirable area off of Lambert's Cove Road, Makonikey, with access to a private association beach and walking trails. There are four plus bedrooms and bright and open living spaces that lead out to a deck and a screened-in porch. Lambert's Cove Beach Access. WT109, Weekly rate: $4,750.
    Karen M. Overtoom Real Estate 508-693-7832. www.overtoommv.com.
    http://www.overtoommv.com/marthas-vineyard/vacation-rentals/West-Tisbury/property/?pid=157.

  • 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.

  • Vineyard Haven

    Enjoy all the amenities of Tashmoo Woods. Tennis, pool, private association beach and a place to kayak or canoe. Located only minutes to Vineyard Haven, this location is a favorite for all age groups. Beautiful home which has everything you would want. From the minute you get up and have coffee on the screened porch, to walking over to play golf, swimming in the pool or going to the private association beach for the day. Activities such as shopping, or some of the finest restaurants are available only minutes away. VH419. Weekly rate: $5,000. Karen M. Overtoom Real Estate 508-693-7832. www.overtoommv.com.
    http://www.overtoommv.com/marthas-vineyard/vacation-rentals/Vineyard-Haven/property/?pid=151. VH419.

  • Vineyard Haven

    This Tashmoo Cove condo has a brightly lit open floor plan. The quiet neighborhood association pool and tennis courts are just a short walk away along with a stretch of association beach which is about a mile from your front door step. Here, you are only about a mile and a half from town in this well appointed home away from home. Enjoy the wrap around deck and patio dining area. You really can't go wrong in this charming vacation get-away. VH415, Weekly rate: $2,700. Karen M. Overtoom Real Estate 508-693-7832. www.overtoommv.com.

    http://www.overtoommv.com/marthas-vineyard/vacation-rentals/Vineyard-Haven/property/?pid=457.

  • Vineyard Haven

    This beautiful home has lots of open space for cooking, yard activities or just plain relaxing. Private association beach overlooking the Elizabethan Islands. Plan a sunset picnic on the beach or stroll down in the morning to see the rays of sun break on the water. Association Makonikey Beach access. VH414, Weekly rate: $4,500. Karen M. Overtoom Real Estate 508-693-7832. www.overtoommv.com.

    http://www.overtoommv.com/marthas-vineyard/vacation-rentals/Vineyard-Haven/property/?pid=357.

  • Edgartown

    This lovely cape is newly renovated and fully equipped with bright airy furnishings. The living room, kitchen, and dining spaces are all open to one another, and there is an additional family room that is separate with TV. Enjoy the large back deck and outside shower after a hot sunny day at South Beach. Bike trails to downtown and the beach are just a short distance from the house. Kitchen, outdoor shower, washing machine and dryer. Recent improvements for 2018 include: AC, new back deck, screened in porch & front porch. ED307, Weekly rate: $3,800. Karen M. Overtoom Real Estate 508-693-7832. www.overtoommv.com.
    http://www.overtoommv.com/marthas-vineyard/vacation-rentals/Edgartown/property/?pid=377.

  • Chilmark

    Fabulous Chilmark home offers two levels of living space. On the first floor there is a fully equipped kitchen open to the dining room, a living room with fireplace, built-ins and sliders to a deck overlooking a meadow and the most incredible water views. There is a half bath, a master suite with private bath with jacuzzi tub and a private outside shower. The lower level offers 2 bedrooms, each with its own bathroom and a living room with wet bar.
    The house also has mini-spilt air conditioning for extra hot days. Just a short distance to a private association beach. CH216. Weekly rate: $9,000. Karen M. Overtoom Real Estate 508-693-7832. www.overtoommv.com. http://www.overtoommv.com/marthas-vineyard/vacation-rentals/Chilmark/property/?pid=213.

  • Aquinnah

    Walk off the deck of this wonderful beach house right onto the dunes! Enjoy swimming, fishing, sailing, snorkeling, or just relaxing the day away. At the end of the day, watch the spectacular sunsets! When Dogfish bar surfaces, collect sand dollars. Comb the beach for shells and sea glass. Live in the rhythm of the tides. Nature restores and renews and revives. AQ606, Weekly rate: $7,500. Karen M. Overtoom Real Estate 508-693-7832. www.overtoommv.com.
    http://www.overtoommv.com/marthas-vineyard/vacation-rentals/Aquinnah/property/?pid=331.

  • Aquinnah

    Great water view property in Aquinnah - this immaculate contemporary has that unique combination of a beautifully designed, year-round home, and has an outstanding view of the Sound and Elizabeth Islands. Not only is the property packed with many custom details, but the home's layout is perfect for relaxed living - with a fantastic kitchen open to the dining and living areas that spill right out onto the screened porch and deck. AQ610 Weekly rate: $4000. Karen M. Overtoom Real Estate 508-693-7832. www.overtoommv.com.

    http://www.overtoommv.com/marthas-vineyard/vacation-rentals/Aquinnah/property/?pid=346.

  • 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.

  • Oak Bluffs

    Centrally located to Edgartown, Vineyard Haven and Oak Bluffs. Just a short drive will take you to any of the town beaches. The home is located on over a 1/2 acre of landscaped property in a beautiful, private, neighborhood, with private roads great for biking and is wonderful for families, friends or even a romantic getaway. The community is exclusive to guests and is tranquil and quiet. The bike path and bus route is located right off of the community and is a breeze to get to. Within a very short walk is the State Park with jogging trails and places to explore.
    OB521,Weekly rate: $3,000. - $5,000.Karen M. Overtoom Real Estate 508-693-7832 www.overtoommv.com.

    http://www.overtoommv.com/marthas-vineyard/vacation-rentals/Oak-Bluffs/property/?pid=449.

  • 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. 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: $3,000. - $5,000. Karen M. Overtoom Real Estate 508-693-7832 www.overtoommv.com.
    http://www.overtoommv.com/marthas-vineyard/vacation-rentals/Oak-Bluffs/property/?pid=451.

  • Oak Bluffs

    Relaxed quiet vacation living with large outdoor deck and open living/dining areas. Ocean views from Living Room, Dining Room, Kitchen, and 4 out of 5 bedrooms.. Near East Chop Light; view ferries to and from Woods Hole. A/Cs in Living rooms & all Bedrooms. Gas grill, 2 outdoor showers, 2 kitchens, 2 washer/dryers. Sleeps 10. Cable TV, WiFi, Roku (streaming Netflix etc.) Quiet neighborhood/no through traffic, 1.5 miles to Oak Bluffs Circuit Ave., 5 min. to Vineyard Haven or OB Ferry. Shady front yard. Minimum 2 week rentals in August. OB531, Weekly rate:$5,000. - $8,000. Karen M. Overtoom Real Estate 508-693-7832 www.overtoommv.com.
    http://www.overtoommv.com/marthas-vineyard/vacation-rentals/Oak-Bluffs/property/?pid=450

  • Chilmark

    A comfortable contemporary home that includes a key to Black Point private beach is ideal for laid-back Vineyard living, or elegant entertaining with both ocean and hillside views. Large open floor plan in the living areas, bring the outdoors inside with spectacular sunshine and sweeping views. No attention to detail missed.
    CH201, Weekly rate: $8,000. - $12,000.
    Karen M. Overtoom Real Estate 508-693-7832. www.overtoommv.com.
    http://www.overtoommv.com/marthas-vineyard/vacation-rentals/Chilmark/property/?pid=453.