Classifieds: Vacation/Summer Rentals

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    Available July 20-27th! One week left! Set on a nicely landscaped lot with tennis, screened-in porch, large back deck, BBQ, outdoor shower, W/D, fully equipped kitchen in open layout. 3 bedrooms, 3 bath which includes one large master suite. $3500/week. Call/text for info/photos 774-563-8177.

  • 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: or text or call 508-801-6435.

  • Edgartown

    Private Luxury Retreat in Katama with Heated Pool
    Stunningly beautiful house on Edgartown Great Pond. Property has one boat dock and another smaller dock. There is access to Atlantic South Beach by boat. In-ground swimming pool with pool house and patio surrounding. Lovely gardens throughout with exceptional privacy. This property has it all. Weekly Rate: $9,000. Karen M. Overtoom Real Estate 508-693-7832. ED306.

  • Chilmark

    Wonderful Open Spacious Chilmark Home
    Set high on a hill in picturesque Chilmark is this absolutely wonderful 3 bedroom home with a finished walk out that has a sofa bed. The grounds are beautiful. Wonderful screen porch for your morning coffee or sit in the back yard and enjoy the view. Short drive to Alleys General Store, Lucy Vincent Beach and the Chilmark Store. You have access to Lucy Vincent beach. This house accepts pets with an additional deposit of $300. Weekly Rate: $3,500. Karen M. Overtoom Real Estate 508-693-7832. CH218.


    Well appointed Katama vacation home available for August 18-25th with ferry tickets. Located 1.5 miles to beach and town on private, wooded cul-de-sac near Edgartown Great Pond. 3 bedrooms/2 bath, fully equipped with outdoor shower, BBQ, bikes, beach chairs, decks, linens, towels, laundry, cooks kitchen. Call/text Sharon @ 617-794-5898 or email

  • 2 Bedroom Oak Bluffs Apartment

    New 2 bedroom apartment. Short walk to Oak Bluffs town and beaches. Available some weeks in July and end of August. Shoulder season availability as well. $3,000 a week for July/August. Call 508-843-4005 if interested.


    Gorgeous 3-bedroom, 3-bath house, 3500 sq. ft. West Tisbury, Lambert's Cove area, weekly or monthly.  See photos at Call 508-939-1414.

  • West Tisbury

    This beautiful tasteful modern home has many charming elements. The bright open airy floor plan offers a generous kitchen, welcoming dining room and warm living room surrounded by windows and decks. This home is perfect for hosting family and friends or enjoying quiet time on the deck. Its location is perfectly nestled in the woods yet is close to popular Lambert's Cove Beach. WT128 Weekly Rate $4,400. Karen M. Overtoom Real Estate 508-693-7832.

  • Vineyard Haven

    This Tashmoo Cove condo has a brightly lit open floor plan. The quiet neighborhood has an association pool and tennis courts that are just a short walk away along with a stretch of association beach which is about a mile from your front doorstep. 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 or stay inside; 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.


    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.


    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.


    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.


    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.


    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.


    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.


    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.


    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.


    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.


    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.

  • 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

  • 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

  • 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.

  • 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.

  • 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.

  • 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.