Holiday houses in Chilmark

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Top-rated holiday rentals in Chilmark

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Guest favourite

Guesthouse in Menemsha

4.95 out of 5 average rating, 91 reviews

Beautifully Renovated 1800s Chilmark Barn

Beautiful 2-story private barn in Chilmark on Martha's Vineyard. Secluded yet convenient. Perfect for a couple or a couple with older children (space not good for those with mobility issues). Downstairs living area, dining area, fridge, toaster, coffee maker, half bath -- shower is outside in the private garden. Loft-style sleeping area upstairs (2 private sections). 2 friendly labs and 5 chickens on premises. Walk to Chilmark Store, easy bus access. Walk-on pass to town beaches, no car pass

Guest favourite

Guest suite in Menemsha

4.91 out of 5 average rating, 127 reviews

Studio Guest Suite in Modern Barn House

A beautiful guest suite on Martha’s Vineyard with a private entrance on the back wing of our newly renovated modern barn house. Surrounded by trees, beside a large meadow, this airy suite has vaulted wood ceilings with skylights. Enjoy the outdoor shower and new outdoor sitting area. The location is prime and centrally located, just off historic Music St, a short walk to our small town center which provides many amenities. Ask about our other private guest suite if you are traveling with others

Guest favourite

Home in Menemsha

4.96 out of 5 average rating, 28 reviews

Fun, Authentic, Waterfront Cottage/air conditioned

This authentic beach cottage is centrally-located in the fishing village of Menemsha with stunning views of the sunset, the harbor, the beach and Menemsha Creek. Charter a fishing boat in the harbor across the street or spend the day on the beach just a few steps away. As you meander back to the house, pick up fresh fish to grill on the deck or pre-cooked lobsters and steamers. If you prefer to eat out, rinse off in the outdoor shower and take a walk around the corner to dinner with a view.

Guest favourite

Apartment in Menemsha

5 out of 5 average rating, 56 reviews

Butterfly Farm Sanctuary Bright Sunny Studio Apt

Spacious & serene in a rural natural setting of West Tisbury. Private, modern, light-filled studio on the first floor walkout of a newly built 2021 post and beam home. Beautifully landscaped, abutting the state forest. Full amenities, 10ft high ceilings, windows and French doors with stone patio sitting area. Studio is down a long dirt driveway located mid-Island, near beaches, trails, and all towns. Just a mile to the Farmers Market, Artisan fair & Alley's General Store. The perfect retreat!

Guest favourite

Guesthouse in West Tisbury

4.96 out of 5 average rating, 74 reviews

Vineyard Meadow Artist Studio

This lovely artist's studio is just steps from miles of trails. Walk to the beach or meander through the woods of Long Point Wildlife Refuge, experiencing the serenity of this still untouched corner of Martha's Vineyard. This studio includes a bathroom with a shower, a washer/dryer and a kitchenette. It is the perfect spot for a lone artist, a couple or a family to enjoy Martha's Vineyard any time of year. This property shares the driveway and parking with Vineyard Meadows Writer's Cottage.

Top Guest favourite

Apartment in Oak Bluffs

4.98 out of 5 average rating, 206 reviews

Sunny Studio Apartment on Martha's Vineyard

Our Sunny Studio is centrally located on Martha's Vineyard. A down-island location with an up-island feel. Open and airy studio with kitchenette and bath. The apartment has all the essentials. The apartment is located within walking distance of hiking and biking trails. A 10 to 15 minute car ride to any down-island town / beach. ***Please Note: Although conveniently located we are not within walking distance to Bars or Restaurants. We do recommend first time visitors rent or bring a car.

Top Guest favourite

Apartment in Falmouth

4.97 out of 5 average rating, 225 reviews

Modern Luxury Apt. | 7 min from Commons

This luxury 1Br + 1bth apartment is the perfect getaway. - 650 square feet, newly renovated - 15 Minutes from Old Silver Beach, South Cape Beach, and Falmouth Heights beaches - Steps from 1,700 acres of walking trails (Crane Wildlife) - 7 minutes to Mashpee Commons (shops and restaurants) - 15 minutes to Main Street Falmouth - 13 minutes to Ferry for Marthas Vineyard - 85” smart TV - 5 minutes to Shining Sea Bike Trail - Coffee/Espresso Machine - 2 minutes from Paul Harney Golf Course

Guest favourite

Guesthouse in Menemsha

4.98 out of 5 average rating, 215 reviews

Beautiful Guest House in Chilmark

This newly renovated guest house is located in a quiet and very private setting in Chilmark. The guest house is located above the garage adjacent to the main house with a private entrance. It has a queen size bed with two oversized chairs. There is a full bathroom in addition to a private outdoor shower. A small kitchen features butcher block countertops, a stainless steel sink, refrigerator and electric stove. Central air conditioning + heat make it the perfect getaway for all seasons.

Top Guest favourite

Guesthouse in Menemsha

5 out of 5 average rating, 76 reviews

Country cottage walk to Alley's General Store

This sunlit summery cottage is in a very quiet, private and pastoral setting, situated 100 feet from the small Tiasquam River, with many birds chirping in the abundant vegetation and trees nearby. Because of the river's proximity, the cottage has a Composting Toilet. My wife and I live on the property uphill from the cottage. The property is in the countryside but a 5 minute walk to the local town center.

Top Guest favourite

Guest suite in Oak Bluffs

4.99 out of 5 average rating, 168 reviews

Quiet Hide Away

Lovely efficiency suite with private entrance in a quiet neighborhood. Private space located over attached garage. Plenty of space for two guests. Comfortably appointed with queen bed, dining set, living area with tv and full bath. Enjoy a coffee or cocktail on the private deck. Toaster oven, refrigerator and coffee maker will start your day right before heading to nearby beaches, golf courses or shopping.

Guest favourite

Home in West Tisbury

5 out of 5 average rating, 47 reviews

Idyllic renovated home across from Seth's Pond

Idyllic renovated farmhouse across from Seth's Pond and 0.6 miles from the infamous Lamberts Cove beach. Enjoy the views from the expansive enclosed front porch, play in the 2 acre yard and relax on the back patio with hardlined gas grill. Brand new kitchen, many recent renovations and a fully stocked home ensure a comfortable stay

Guest favourite

Home in Barnstable

4.97 out of 5 average rating, 39 reviews

1 minute walk to beach, Saturday to Saturday

The cottage duplex is across the street from Covell's Beach, we also have a private beach without life guard supervision. There is a family residing on the other side of the duplex. We offer an outdoor shower, grill, outdoor picnic area with an ocean view.