Vacation Rentals By Owner In Chilmark, MA

$568.98

Peaceful Chilmark Farmhouse by Menemsha Beach

Chilmark, Massachusetts, United States

Experience Martha's Vineyard 'up-island' at this tucked-away 4-bedroom, 3-bath gem in Chilmark. Situated just a short walk from the quaint fishing village of Menemsha, this home is ideal for travelers seeking both privacy and seclusion and easy access to the coast. On-site, make yourself at home with a harvest meal in the country kitchen or evening cocktails on the deck. After a day at Lucy Vincent or Squibnocket Beach, come home to a refreshing outdoor shower and a cool breeze in the trees.brbr-- THE PROPERTY --brbrMassTaxConnect ID C0234780620 | 2,400 Sq Ft | Walking Distance to Beach | Secluded Forest SettingbrbrIdeal for a family's summer escape, this vacation rental provides easy access to must-see sights like the Aquinnah Cliffs, the Vineyard Farmer's & Flea Markets, and the world-famous Menemsha Beach sunsets.brbrBedroom 1: Queen Bed | Bedroom 2: Queen Bed | Bedroom 3 (Pink Room): Twin Bunk Bed | Bedroom 4 (Blue Room): 2 Twin Beds | Living Room (Solarium Room): FutonbrbrHOME FEATURES: Flat-screen Smart TV, cozy sunroom, wood-burning fireplace, gas fireplace, antique piano, dining tables, books, board games, VCR w/ video librarybrOUTDOOR VIEWS: Spacious deck w/ tanning chairs, dining set w/ gas grill, outdoor shower, wood-burning fire pit w/ Adirondack chairs, wooded backyard w/ swingbrKITCHEN: Fully equipped, stainless steel oven, cooking basics, dishware & flatware, microwave, toaster, drip coffee maker, Crock-Pot, blenderbrGENERAL: Free WiFi (high speed), window A/C units, towels/linens, ceiling fansbrFAQ: 3 small steps required for home accessbrPARKING: Driveway (3 vehicles)brbr-- THE LOCATION --brbrMENEMSHA (0.4 miles): Menemsha Beach, Menemsha Harbor, Larsen's Fish Market, The Home Port Restaurant, Menemsha Galley, Chilmark Pond, Menemsha Blues, Pandora's Box BoutiquebrBEACH DAYS: Menemsha Public Beach (0.4 miles), Lucy Vincent Beach (2.4 miles), Squibnocket Beach (3.4 miles), Lobsterville Beach (6.5 miles), Public Beach at Aquinnah Cliffs (7.4 miles)brMUST-SEE SIGHTS: Chilmark Flea Market (3.0 miles), Tisbury Farmers Market (6.0 miles), Gay Head Lighthouse (7.0 miles), Black Dog Wharf Vineyard Haven (11.5 miles), Main Street Edgartown (12.1 miles), Flying Horses Carousel (14.2 miles), Circuit Avenue Oak Bluffs (14.2 miles), Jaws Bridge (16.4 miles)brISLAND EXPLORING: Menemsha Hills Reservation (2.0 miles), Great Rock Bight Preserve (2.5 miles), Poly Hill Arboretum (6.2 miles), Cedar Tree Neck Sanctuary (9.2 miles), Long Point Wildlife Refuge (10.2 miles), Felix Neck Wildlife Sanctuary (15.0 miles), Cape Poge Wildlife Refuge (18.0 miles)brAIRPORT: Martha's Vineyard Airport (10.0 miles)brbr-- 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- C0234780620br- No smokingbr- No pets allowedbr- No events, parties or large gatheringsbr- Additional fees and taxes may applybr- Photo ID may be required upon check-in

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$781.9

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Private Vacation Home

Pet-Friendly Historic Chilmark House

Chilmark, Massachusetts, United States

Renovated historic house (1870). Large living room/dining area. 4 bedrooms sleep 8 plus sofa sleepers. 3 full bathrooms. Located between Lucy Vincent and Squibnocket beaches, 2 miles from Menemsha Harbor & Village and spectacular sunsets. A short stroll to Chilmark Center, Chilmark Store, Library, Community Center, Tennis & Basketball Courts, Chilmark Chocolates Store & Town Hall. 3 Kayaks available. Property contains historic stone walls, metal & granite sculptures and original hitching posts. The house includes a large secluded deck and sprawling private yard with hammock and swings, plenty of room to play and run. The yard is shared by people who rent our barn.

4

Bed

3

Bath

10

Sleeps

$6781.79

/ Nightly

Private Vacation Home

Private beach compound. Please do not book without contacting the host

Chilmark, Massachusetts, United States

Amazing Chilmark summer compound. On the Cliffs! 2 separate houses that can be rented together or separately. Privacy. Google Wequobsque Cliffs. brTennis court. Private beach. Prime Chilmark location. Dramatic views. Please inquire for options, given the multiple houses.

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$912.22

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Private Vacation Home

Walk to private beach from beautiful Abels Hill house

Chilmark, Massachusetts, United States

The house is a large family house in the Abels Hill community of Chilmark. The community shares use of a private south shore beach with beautiful Chilmark Pond for kayaking or canoeing, a tennis court, and access to miles of hiking trails. brbrThe house has 6 bedrooms, and sleeps 13. 3 King sized beds, 1 Queen. 2 Doubles. One of the double bedrooms also has a twin. A large vaulted ceiling living/dining room looks out a glass wall over the 5 acre meadow with stone wall and organic vegetable garden that you can harvest from for your dinner or green smoothie! An exterior seating area on a deck w grill extends the living room and overlooks the meadow.brbr2 full bathrooms plus a powder room and outdoor shower with stained glass window! brbrA TV room and a music room, with electric piano, saxophone, bass, drum kit and drum machine are extra spaces for rainy days.brbrIts easy to walk to the beach and the pond from the house, which is across south road, just down the hill. To get to the beach you either use the Abel’s hill small boat which seats 4, our kayak (which seats 2), or wade across the shallow pond. Hiking trails for woodland running or hiking from Abels Hill take you to acres of magical preserved forests. brbrThe house is simple, colorful and joyful.

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$1077.91

/ Nightly

Private Vacation Home

Spectacular Newly Renovated Home in Menemsha

Chilmark, Massachusetts, United States

This spectacular newly renovated home in Menemsha on Martha's Vineyard, was originally designed by a Frank Lloyd Wright apprentice, and features 3 bedrooms and 2 bathrooms and a large open concept living dining area. A total renovation was completed in the spring of 2020 and the house features, a modern updated gourmet kitchen, 3 comfortable bedrooms, 2 new bathrooms, and an open concept living/dinning area with vaulted ceilings, bar area and a large dining area. There is a wrap around deck around the entire house and dramatic floor to ceiling glass in the living area. The house also features a loft area perfect for extra sleeping capacity, kids play area, work out area, or home office. There is also an amazing new outside shower, with a 16 rain fall shower head, plenty of hot water and a gorgeous modern design of wood/concrete/steel, that provides an incredible outdoor shower experience. The house is a short 5 min drive from the Menemsha Beach, Larsen's Fish Market, Homeport Restaurant, Menemsha Market, Chilmark Store, and Lucy Vincent Beach. brbr** The house was published in Dwell Magazine online in Sept 2020, a link to the article is here: https://www.dwell.com/article/the-shop-erin-pellegrino-makethink-759aeaadbr** The house won 1st place in the 2021 Global Architecture and Design Awards, Rethinking the Future Awards 2021, for the Private Residence category. A link to the article is here: https://awards.re-thinkingthefuture.com/rtf-awards-2021-winners/the-shop-by-matter/ br** The house was also published in AN Interior Magazine in Dec 2020, a link to the article is here: https://aninteriormag.com/marthas_vineyard_the_shop/ brbr- 3 Bedroom, 2 Bathroom. (BR: 1 King, BR2: Queen, BR3: (1) bunk bed and (1) Trundle); Loft: 2 Queen, 1 Twin.br - Bedrooms (7) + Loft (5) = 12 brbr- Access to Lucy Vincent Beach and Squibnocket Beaches (10 min away) (Beach stickers can be purchased at Chilmark Town Hall/Online). Mememsha Beach (5 min away) is open to public.brbr- Access to Menemsha Pond (via Cove Rd, deeded access)brbr- Beach Chairs, Beach Towels & Boogie Boardsbrbr- WiFi / Internet (High speed)- Available throughout the house (Plenty of bandwidth for Zoom/Teams calls)brbr- Chef's kitchen with 5 burner stove (all new appliances)brbr- Dishwasher, Microwave, Oven, Washer/Dryer.brbr- Coffee Maker & Keurigbrbr- Comcast Cable/Flat Panel TV/DVD/Streamingbrbr- Sonus - Audio Systembrbr- BBQ grill and outdoor seatingbrbr- Peloton exercise bike (new summer 2020)brbr- Spectacular Outside Shower (new summer 2020)brbr- Air Conditioning (new summer 2021)! br

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$1035.18

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Private Vacation Home

Menemsha Pond waterfront Available July 18-25, 2026 BOOK NOW!!

Chilmark, Massachusetts, United States

brbrPond front cottage and attached Silo house, 4-5 bedrooms on large acreage fronting Menemsha Pond, big views of the long lawn and waterfront. Quiet private neighborhood in Chilmark . Private waterfront beach available at end of lawn and ability to purchase pass to Chilmark's Lucy Vincent Beach or Squibnocket Beach, a short drive by car. Pristine family retreat, definitely one of a kind memorable location for relaxing and water sports in the vast Menemsha Pond and ocean Several family gathering spaces in deep chairs on the brick floored screen porch for cocktails or out on the lawn in chairs overlooking the water, or a day in the hammock or at water's edge for boating or paddle boarding.It's an era gone by with all modern amenities. and updates.What a treasure!brThere is a main cottage, and an adjacent bunkhouse and an attached round Silo with sleeping arrangements in each.Smell the ocean, see the stars at night and deeply relax with a swim after breakfast and before dinner.All you need is a bathing suit!

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$1619.65

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Private Vacation Home

Charming Chilmark beach house with private Abel's Hill beach access

Chilmark, Massachusetts, United States

Lovely house at the top of Abel's Hill with access to private Abels' Hill Beach a half mile away. The house is wonderful for families with 5 bedrooms, three and half baths, two outdoor showers, well appointed kitchen, fire pit and lots of toys including boogie boards, kayaks, etc. There is an eigthy five foot deck with a seating area, dinig table for 12 and chaises overlooking a meadow. Our property also abuts the Sherrif's Meadow trail system. Newly installed A/C

5

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2

Bath

10

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$6625.02

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Private Vacation Home

Private Hilltop Chilmark Estate with private tennis court, gym and hot tub

Chilmark, Massachusetts, United States

Private 8 acre estate with new hot tub and tennis court. Enjoy your walks through 56 acres of preservation land and the Tiasquam river.brThe house is filled with art from local artist Colin Rule, Kara Taylor, Traeger Di Pietro, Scott McDowell and unique furniture what have been collected all over the world.brbrMASTER BEDROOMbrStart your days with incredible view!brKing size bed with gel infused memory form Serta iComfort mattress, down pillows. Unique reclaimed rustic cupboard from India next to the bed. brAntique Indian hand carved door frame converted to a full size mirror.brClimate control with central AC and fan.brFull bathroom with shower, jet tub and bidet.brbrSECOND MASTER BEDROOMbrKing size bed with gel infused memory form Serta iComfort mattress on the second floor with a thousand year old unique door from India. There is a drawer, antique rug and closet. brbrTWO QUEEN BEDROOMSbrTwo queen bedrooms with a comfortable mattresses, closets and a beautiful view on the second floor.brbrKITCHENbrVery bright and spacious fully equipped chefs kitchen with everything you need. There is an oven, microwave, vitamix blender, smeg toaster, breville juicer, breville espresso machine, brand new dishwasher and wine fridge.brbrDINING AREAbrCustom teak slab dining table with eight seats. There is also a small table with three Indonesian wicker chairs.brbrLIVING ROOMbrBright and spacious living room with spactacular sunset view. Huge cozy sectional with additional comfortable chairs and teak root coffee table. brJesse Child custom made fire place for cozy evenings at the house. brThe entire house has radiant heat and central air. brbrTV ROOMbrEnjoy your favorite movies on the 85 inches TV on the massive comfortable sofa.brbrLAUNDRY ROOMbrThere is brand new LG washer, LG dryer and steamer.brbrSCREENED PORCHbrThis outdoor space is perfect for breakfasts or dinners with sunset view. There is a sofa and table seating for eight people. brbrOUTDOOR AREASbrThe property surrounded by 56 acres of preservation land so you have full privacy.br- eight person new hot tubbr- private professional tennis court two minutes walking distance from the housebr- big porch with big round sun bed what you can use for sunbathing or watching the stars or sunsetbr- outdoor bathroom what you can use before and after a hot tub to not entry the house br- outdoor stainless still grillbr- fish pond surrounded of a lot of plants and flowers with sofas for five peoplebr- personal herbs garden with fresh basil, mint, parsley, chives, rosemary.brbrWe do allow some pets which are allowed upon request.

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$1234.31

/ Nightly

Private Vacation Home

Post and Beam home with westward views of the ocean and sunsets

Chilmark, Massachusetts, United States

Welcome to the barn! This beloved home started as a post and beam barn built in 1983. 10 years later it was expanded; on one side, an open gourmet kitchen is flanked by a fireside breakfast nook, and a dining area looking out to the sea, and on the other side there are 3 additional bedrooms.brbrThe kitchen was designed for a family that loves to cook. At your disposal is a full array of copper pots, an espresso machine, air fryer, Wolfe range, cookbooks, and plenty of tools of the trade. The fireplace even includes a pizza oven for the adventurous chef!brbrThe original center of the house has two living rooms, one which looks out onto the deck and ocean, and the other with a view to the garden and doubles as a TV room. Upstairs in the main section the master bedroom opens to a balcony overlooking Menemsha Bight and Menemsha pond with views to Squibnocket pond and the ocean beyond. brbrThe bedroom wing includes two large downstairs rooms (1 queen, 1 double), and a floorthrough upstairs bedroom with a double bed, two twin beds and separate bath.brbrThe house was made for comfort and decorated with art and furniture made by family and friends. From watching the sunset on the deck, to relaxing in the garden, there is both space to spread out and follow individual interests, and to gather together.brbrThe iconic Menemsha Fishing village is just a short walk or drive away. There you will find two fish markets, a bakery, galleries, antique and clothing shops and Menemsha Beach itself. You will also have access to Lucy Vincent and Squibnocket, two magnificent surfside beaches.brbrMass Certificate Number: C0020250620

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$647.86

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Cottage

Waterfront cottage a short boat ride to the ocean beach

Chilmark, Massachusetts, United States

Our waterfront cottage on Chilmark Pond is a short boat ride to a stunning barrier beach on the Atlantic Ocean. There is access to Abel Hill Association tennis courts, miles of private beach for walking, swimming, body surfing and birding and Chilmark Pond for boating. In the main house there are 3 bedrooms, a spacious open, bookshelf-lined family room with a large round dining table and smaller puzzle table, a very well-equipped kitchen, a full bath and a half bath. The close-by back house has twin beds and a bunk bed, a half bath and a laundry room. It is a great place for kids or guests. Abel's Hill is a short ride to Menemsha's fish stores and great sunsets. The use of beach chairs and a canoe is included. You are also eligible with the lease to pay $100 for a parking permit to Lucy Vincent Beach a few miles away.

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Sleeps

$1039.75

/ Nightly

Private Vacation Home

Mid-Century Modern - All Glass House - Designed By Frank Lloyd Wright Apprentice

Chilmark, Massachusetts, United States

Mid-Century modern glass house, in Menemsha, on Marthas Vineyard. Designed by a Frank Lloyd Wright apprentice, this all glass house, embodies the integration of nature and architecture, with simple utilitarian design in serene location, minutes from Menemsha or Lucy Vincent Beach. Built in the early 1960s, and recently updated, this all glass house, features 3 bedrooms, 2 bath rooms, and a large open concept living & dining area. The house features floor to ceiling glass in every room. There is a wrap-around deck around the entire exterior, and another deck around the interior open-air courtyard area. The house has a large, new outdoor shower, with a stone sink. There are distance water views of the vineyard sound and the Elizabeth islands. The house is a short 5 min drive from the Homeport Restaurant, Menemsha Market, Chilmark Store, or Lucy Vincent Beach. Awarded Progressive Architecture's design excellence award in 1963, this historical updated mid-century modern house, offers the best of simple indoor/outdoor living, with all updated modern conveniences. brbrNew in addition to The Glass House in 2023, is The Studio, a gorgeous space (about 16 x 16), with a wrap around deck, that is bulit over looking a stream. This Studio is accross the driveway from the main house (about 80 ft) and can be used as an additional bedroom with a queen bed or a home office space. brbr** The Glass House was featured in Martha's Vineyard Magazine in Spring 2018 issue. The full article is here: http://mvmagazine.com/news/2018/03/01/exurban-renewalbrbr- 3 Bedroom, 2 Bathroom. (BR1 Queen, BR2 Queen, BR3 (2) bunk beds) - Sleeps 8 (+2 in Studio)br- The Studio, 1 Bedroom, no bath (BR4 - Queen) - Sleeps 2br- Access to Lucy Vincent Beach and Squibnocket Beaches br- Access to Menemsha Pond (via Cove Rd, deeded access) br- WiFi / Internet - Available throughout the housebr- Chef's kitchen with 5 burner stove (all new appliances)br- Dishwasher, Drawer Microwave, Oven; BBQ on deckbr- Coffee Maker & Kreurigbr- Direct TV / Flat Panel TVbr- Sonus - Audio Systembr- Amazing outside showerbrbrFAQ - Privacy in a Glass House - Although the house is 100% glass, 100% privacy can be achieved as all the walls have curtains which can be closed for complete privacy. We typically recommend having the curtains open to enjoy the floor to ceiling views of the natural surroundings, and achieve the intended feeling of the living space's integration into the nature surroundings, but all rooms (bathrooms, bedrooms, etc) can be 100% private as you would need and expect.brbrbr

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Bath

Sleeps

$909.08

/ Nightly

Private Vacation Home

Quintessential Chilmark Retreat - Marthas Vineyard

Chilmark, Massachusetts, United States

Everything you think of when you dream of Chilmark... pastural rolling 2+ acres with water views and stone walls. Ideal location less than 1.25 miles to all Chilmark beachs... St Lucy Vincent, Squibnocket and Menemsha.brbrEverything you think of when you dream of Chilmark... pastural rolling 2+ acres with water views and stone walls. Ideal location less than 1.25 miles to all Chilmark beaches... St Lucy Vincent, Squibnocket and Menemsha. Half a mile to the Chilmark General store. brbrMain house features 2 formal bedrooms and a 3rd bedroom with barn doors off the loft living room. 2nd Bedroom has a charming set of bunk beds plus a queen bed, easily sleeping 3. brbrTall cathedral ceilings with post and beam detailing. French doors lead to expansive deck offers stunning view of Menemsha pond. Spacious kitchen is perfect for those that love to cook with updated appliances. Screened in porch with dining table is perfect for late night chats. Stone fireplace is ideal for chilly early summer or fall evenings.brbrProperty has rolling hills with gorgeous trees and landscaping. Fire pit with seating area to enjoy vineyard evenings.brbrMicro weddings (35 people or less) and small events are possible for an additional site fee. I am also an event planner should you need help planning your special day.brGPS tends to find our address, 27 Abel's Neck Road. You can also find Mapquest driving directions below. brbrThe only tricky part is that Abel's neck is a one-way head in, so enter on Boston Hill Road (just before Abel's Neck if you are headed south) and the keep to the left at the fork to get onto Abels Neck. br• br1.brStart out going southwest on Beach St toward Main St.brThen 0.00 milesbr• 2.brBeach St becomes State Rd.brThen 0.18 milesbr• 3.brState Rd becomes S Main St.brThen 0.01 milesbr• 4.brS Main St becomes State Rd.brThen 0.44 milesbr• 5.brState Rd becomes S Main St.brThen 0.19 milesbr• 6.brS Main St becomes State Rd.brThen 4.68 milesbr• 7.brTurn slight right onto North Rd.brThen 5.68 milesbr• 8.brTurn slight left onto Menemsha Xrd.brThen 1.00 milesbr• 9.brTurn right onto State Rd.brThen 0.66 milesbr• 10.brTurn right onto Boston Hill Rd.brThen 0.13 milesbr• 11.brTurn slight right onto Abels Neck Rd.brThen 0.15 milesbr• br12.br27 ABELS NECK RD is on the right.brYou can obtain a beach sticker for Lucy Vincent or Squibnocket at Town Hall (going North on Middle road, right past the general store on the right). You will need proof of your rental and please specify your check-out date. The pass is $20.

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Sleeps

$330.68

/ Nightly

Cottage

Menemsha - Davis House

Chilmark, Massachusetts, United States

brLocated in Menemsha Village. This quaint cottage is located a stones throw from the Menemsha Harbor. It is the smallest and most affordable of the three houses we rent, yet offers great views.brbrThe house has a living. room, kitchen area and bathroom on the first floor. The one sink is located in the kitchen area. The upstairs has a full size bed, skylight and windows on each side for a nice breeze. This room also has an AC unit, if needed. The stairs are narrow and somewhat steep. There is a picture provided. brbrWalk out your door and across the street to the harbor. Stroll the dock and end up at the beach to enjoy the sunsets...or you can stay right at home and enjoy the sunsets from the living room. Menemsha village has takeout, fish markets, shops and a wonderful family beach all in walking distance. Bus service is also available to take you to other parts of the island.brbrThis cottage is comfortable for a couple or a single person. Also, all renters living in town have access, for a fee, to two exclusive beaches for a fee: Squibnocket and Lucy Vincent.brbrCancellation Policy: A full refund will be given if we are able to re-rent a canceled week.

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$419.67

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Private Vacation Home

Tilton House - Menemsha Harborside

Chilmark, Massachusetts, United States

Menemsha cottage adjacent to Menemsha Harbor in the Town of Chilmark. Historic village cottage for four people. 100 feet to Menemsha Harbor and a two minute walk to the beach. Also, access to two exclusive town beaches (for Town Fee): Squibnocket and Lucy Vincent. brbrWalk out your door and across the street to the harbor. Stroll the dock and end up at the beach to enjoy the sunsets. Our village has a restaurant, fish markets, art galleries, shops and a wonderful family beach, all in walking distance. Bus service is also available to take you to other parts of the island.brbrCancellation: A FULL refund will be given if we are able to re-rent the week cancelled.brbrbrKeywords: House

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$453.18

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Private Vacation Home

Peaceful Wooded Retreat, Short Car Ride to Everything. Week is Friday to Friday

Chilmark, Massachusetts, United States

Comfortable home, providing wonderfully peaceful and refreshing quiet, set on a white oak wooded lot, with 2 fireplaces, newly renovated eat-in kitchen, powder room, laundry room, upper level AC, and a garden of birds. Simply fill the bird feeders and enjoy the variety and song. Take a 2 mile drive to the entrance of Lucy Vincent Beach, 5 miles to Squibnocket Beach, or Menemsha Beach. Enjoy the Yoga Barn down the road and the Community Center, Library, Post Office, TownHall, and Chilmark Store for pizza on the porch, also a short drive away. Also close by, visit the new Grey Barn which features raw milk and organic meats. Avail yourself of many scenic routes for walking, biking, jogging. Lovely restaurants close by and 3 towns to shop in about 20 minutes away. Folks tell us of issues obtaining Ferry Reservations on the weekend, so we've changed to FRIDAY arrival time and to FRIDAY departure.

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Sleeps

$418.5

/ Nightly

Apartment

Cozy efficiency apartment/heated pool

Chilmark, Massachusetts, United States

Small, but cozy bedroom with smart TV, kitchenette with microwave, refrigerator, toaster oven and Keurig coffee maker. brUse of heated swimming pool. Outdoor shower.brWeber grill and table for two private sitting area.brShort walk to Peaked Hill (highest point on the Island) walking trails.brWalk-on pass to Lucy Vincent Beach. brI do not recommend staying here without a car. The property is down a long dirt road and not in walking distance to public transportation.

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$1643.59

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Private Vacation Home

10 minutes walk to Lucy Vincent Beach

Chilmark, Massachusetts, United States

Location! Location! Location!br Charming, and nestled away, this must see post and beam home is situated on the edge of the Keith Farm, which provides multiple sweeping pastoral views and occasional visits by the beautiful horses who graze on the neighbor's property. We have been asked to enjoy their beauty but not to feed them. br Both the isolated beauty of this secluded one acre property and the convenience of this amazing central location, are what make it so special.br This home is beautiful yet not fussy, furnished with both elegance and comfort in mind, with well thought out amenities, including but not limited to a wonderful new kitchen completed in 2022. This fully equipped Cooks kitchen includes a large table that seats 8-10. The deck is appointed with teak furnishings , a large direct line gas grill and wonderful views of the beautiful Vineyard sunsets. Along with the kitchen a new full house A/C systems been installed. Our guests rave about the large outdoor shower. Inside the main house is an open concept living room with cathedral ceilings and the loft area above has a T. V. which is great for hanging out but also can be used as an extra space for house guests on the pull out futon.br4 Bedrooms (each with their own bathrooms) are furnished with plush mattresses and bedding (3 bedrooms are in the main house, the 4th is in the detached cottage) Detached cottage provides an additional bedroom and 500 sq ft of guest space. brWith a screen door and AC unit, you have your choice of enjoying the cool breeze with the screen doors open or to cool off in the AC. Most past guests say this is the prime bedroom!brbrAND THERE'S MORE..........brbr2 minute drive or 10 minute walk to the famed Lucy Vincent Beach; 2 minute drive or 10 minute walk to the Center of Chilmark, the library and the Chilmark Community Center, where you can access a bus during the summer season multiple times a day, to any town on the island; Chilmark is the home to the picturesque working village of Menemsha, which is famous for fresh catch seafood and spectacular sunsets; If you enjoy walking trails, Chilmark has the most of any town on the island; A 10 minute drive out of town will bring you to the famed red clay cliffs with beach below to the town of Aquinnah, formerly known as Gayhead.

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$1144.93

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Private Vacation Home

Classic Modern House on its Own Point of Land with Astounding Views

Chilmark, Massachusetts, United States

Designed by a student of the famous architect Walter Gropius, our house was built in 1949. The house is open and light, with floor to ceiling windows and sliding glass doors, a fireplace with a 50's conversation pit for cozying up in, perfect for an evening of charades or quiet reading. The giant dining table has room for a large family to spread out, or have a group of friends over for a long summer dinner. The multiple couches and seating areas suit a grandma reading aloud to small ones while in another area teenagers chat or grownups have cocktails on the porch, looking at the serene view of the nature preserve across the pond. There is a good layout for two families with children to share the house. It is also a romantic spot for two people to enjoy a beautiful private place.brbrWe have lots of amusements and we are TV free. We have a fantastic collection of children's books, from picture books to favorite read-alouds and young adult books. There is a croquet set and lots of rainy day games and little kid toys. We have a modest but peaceful writers cabin/shed that can be used for quiet work time (no Wi-Fi there). brOur point of land the house sits on (see map) is 9/10ths surrounded by water, Menemsha Pond on one side and Quitsa Pond on the other. Part of the 11 acres is conserved land and the view is beautiful from anywhere. Children love exploring the mowed paths and most likely will find the hidden tree house. Chockers Point has always been occupied by sailors and you can beach a sunfish easily. It is also excellent for jumping into a kayak and exploring the ponds. We provide 2 single kayaks. We also have clamming supplies, our beach is rich with steamer clams in the summer.brbrThis house is perfect for small children, the third generation of our family is now proving that. Children can toddle or paddle about on the private beach on Menemsha Pond, 'Short Beach' (we share it with the other houses on our short road but there is always room) where we all learned to swim. Beach passes for the restricted town ocean beaches are available for purchase from the town with your lease. The free Menemsha public beach and it's great fish markets are nearby. There is a fantastic local farmer's market in nearby West Tisbury twice a week. brChilmark has a wonderful community center summer camp program that runs every weekday morning for children up to 12, where your kids can play sports or make glorious messes. You can sign up by the week. Retrieve your children at noon and go across the street to get a pizza for lunch from the popular Chilmark store. The Chilmark library is excellent and has a lot of kid's programs. brbrIn the fall it is a great spot for quiet adult time. The island is more peaceful and the colors are spectacular. The weather is generally wonderful then and if it is not the wood stove is exceedingly cosy.brbrThis is not a fancy house. It is built very simply, in a style of '50's summer camp minimalism. The comfortable furniture is a little worn, but it's classic style (Eames etc) echos the house. We have only one full and one half bath and a beautiful reconstructed outdoor shower. The house has a very warm feel that we hope you love as we do.brbrWe no longer provide Wi-Fi. Because we are located on a peninsula, the Wi-Fi was provided via a hotspot and we were not able to guarantee the quality of the Wi-Fi for multiple simultaneous users. We have decided that because it is very simple to either use a smartphone as a Wi-Fi hotspot or bring an additional Wi-Fi hotspot as part of a standard phone plane, it is much more reliable for people who need to work remotely to provide their own Wi-Fi and that way they can monitor if other guests are sharing the Wi-Fi with them. Both Verizon and ATT get good service at Chockers Point. Please reach out if you have questions about this. brbrWe do not rent for under 1 week, NO weekends. We give discounts for long rentals.brbrKeywords: Summer House, Derby, Kayaks, Dogs

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$599.88

/ Nightly

Private Vacation Home

Secluded house in the woods with deck, streamside firepit, Vincent Beach nearby

Chilmark, Massachusetts, United States

Relax at this retreat in the woods when you are not spending time on Lucy Vincent Beach or enjoying the sunset down the road in Menemsha. Surrounded by stone walls and walking paths over 20 acres of woods, this spacious three bedroom house is next to a stream (with a campfire ring) and is cut off from the world down a quarter-mile driveway. After a day on the deck or at the beach, enjoy the rustic outdoor shower.brbrIf you are looking for a private spot, this secluded retreat with lush greenery and simple elegance will rejuvenate your spirits. A long private driveway leads to ample parking for this charming New England house.brbrThis light filled home with wide open spaces sleeps 6. The main level includes a master bedroom with a queen size bed, a quiet room with futon couch surrounded by a library, and a bathroom with a full size tub. The open floor plan includes a spacious and sunny living room with various couches and a cozy stove for the occasional cool nights, a piano, a large dining room table, and an open kitchen with a new fridge, earthen dishware, coffeemaker, microwave, blender, toaster, and a fondue set. The entryway stores all shoes and coats out of the way. A separate laundry room with washer and dryer is well stocked with environmentally-friendly laundry detergent. In a hallway closet, a sound system harbors many vinyl records and is connected to speakers in the main room. The second floor has two bedrooms, one with a queen size bed, another room with two twin beds. There is a second bathroom with a step-in shower. brbrThe outdoor living space is breathtaking, comprised of a deck off the kitchen, with a large table and seating for 6, a grill, enclosed hot and cold outdoor shower, and a large lawn area. Our hammock is ideal for an afternoon nap or diving into one of the many books from the house. A tire swing brings playful charm. Interesting mossy stone walls border the lawn area to the wild wooded area beyond. A few steps into the woods, a trail leads to a stream and benches around a fire ring fit for a cozy campfire and perfect for s'mores and singalongs. Trails and a small foot bridge across a bubbling stream are ideal for contemplative walks.brbrThis property is only minutes away from Menemsha Beach with its famous sunsets, Lucy Vincent Beach, the Chilmark public library with many public programs for all ages, and a short drive to the legendary West Tisbury General store. Art galleries, town beaches and many restaurants nearby will keep everyone entertained. Short drive to Cronig’s supermarket.brbrWe use only environmentally friendly cleaning supplies, allergen free bedding and have all hardwood floors. A small flock of guineas keep any ticks and mosquitoes away from the house!brbrRenters are eligible for passes to Lucy Vincent Beach. Beach towels included.

3

Bed

1

Bath

6

Sleeps

$2034.25

/ Nightly

Private Vacation Home

Waterfront, 4-bed/4-bath Contemporary on Menemsha Pond with Private Beach & A/C

Chilmark, Massachusetts, United States

brbrbrbrbrbrbrHeadline: Waterfront, 4-bedroom/4-bath Contemporary on Menemsha Pond with Private Beach & A/CbrbrThis New to the Market, spacious 4 Bedroom is a light filled modern home with a view from every room. This is a retreat filled with calm spaces in which to relax and renew. There are three ensuite bedrooms on the ground floor, each with their own unique water views. Upstairs is a large bedroom with a window seat, plus a bonus space, with twin bed, where a child can sleep and play; the 4th bath and a sitting room with the most extraordinary views. The large comfortable living/dining room has 3 walls of sliders opening onto the decks, while adjacent on one side is an office with views galore and on the other a small library/game room with yet more views. All the views are immediate and mesmerizing as from the bow of a boat, especially from the rear deck with its sweeping views of the entire pond and the sand dunes beyond. This is a secluded location which shares the private beachfront with just one other house. The home has character - with Spanish tiles in the entry, dining room and kitchen which all enjoy walls of glass. The home is completely outfitted with the expected amenities and the furnishings are comfortable and placed for maximum enjoyment of the water views. Linens, towels and beach towels and housekeeping supplies are provided. The kitchen is completely outfitted for meal preparation or entertaining. There is a full set of wrought iron deck furniture with cushions and the house is cooled with brand new mini split air conditioners throughout.

4

Bed

4

Bath

8

Sleeps

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