Holiday rentals in Aquinnah

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Top-rated holiday rentals in Aquinnah

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Guest favourite
A cozy living area features a light-colored sofa adorned with cushions next to a wooden table. Sunlight filters through window shades, illuminating the space. A vintage wooden box holds a bouquet of flowers, while wicker chairs provide additional seating, creating a relaxed atmosphere.
Home in Chilmark
5 out of 5 average rating, 22 reviews

The Blueberry House on Martha’s Vineyard

Welcome to 'The Blueberry House' in Chilmark, up-island in beautiful Martha's Vineyard. This sweet private cottage is designer done with gorgeous furnishings, comfortable touches, and a nod to all things local. This 2 bedroom, 2 bath, 2 story home with outdoor shower will quickly find a place in your heart. Prime location off North Road next to North Tabor Farm with quick access to Great Rock Bight preserve, Menemsha Beach and Chilmark Store. Multi-week stays require weekly cleaning $300 each.

Top guest favourite
A bright sleeping area features a spacious white bed with decorative pillows and bedside lamps. A small kitchen area with light-colored cabinetry is visible in the background, complemented by a large window allowing natural light. A cozy seating area adds to the warmth of the space.
Guest house in Chilmark
4.98 out of 5 average rating, 230 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 and outdoor shower. A small kitchen features butcher block countertops, stainless steel sink, refrigerator and 2 burner electric stove and island. Air conditioning and heat. The space comes with a walk -on-pass to Lucy Vincent Beach.

Top guest favourite
An outdoor deck with a wooden dining table and matching chairs is shown, illuminated by a vibrant sunset. Lush greenery and the neighboring buildings can be seen in the background, creating a peaceful setting for dining al fresco.
Home in Chilmark
4.98 out of 5 average rating, 40 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.

Top guest favourite
A modern barn house exterior features a dark wood façade with a balcony access. Stone steps lead up to the entrance, flanked by lush greenery and blooming flowers. A pathway of flat stones winds through the vibrant garden, enhancing the serene atmosphere of the property.
Guest suite in West Tisbury
4.94 out of 5 average rating, 168 reviews

Loft Guest Suite in Modern Barn House

A beautiful guest suite on Martha’s Vineyard with a private entrance on the 2nd floor of the back wing of our newly renovated modern barn house. Surrounded by trees, beside a large meadow, this large 400 square foot suite has vaulted wood ceilings and skylights. Enjoy the outdoor shower and new outdoor sitting area. The location is centrally located, just off historic Music St, a short walk to a small town center which provides amenities. Ask about our other guest suite if you are with others.

Top guest favourite
A historic home features classic New England architecture, with a peaked roof and wooden shingle siding. White trim outlines the windows and door, while a white picket fence surrounds the property. Lush greenery and colorful flowers enhance the welcoming exterior under a clear blue sky.
Home in Sandwich
5 out of 5 average rating, 223 reviews

Quintessential Waterfront Historic Cottage

Set in a historic district and on a quiet pond shore, create memories with family and friends that will last a lifetime. Enjoy quintessential New England views from every angle. Coffee, restaurants, shopping & a fresh spring water fountain within a short walk to village center and under a mile to the nearest beach. Spend time walking the local area, exploring Cape Cod and relaxing in an atmospheric setting. Each room has been curated in a timeless tone, with relaxation and comfort in mind.

Top guest favourite
An open studio layout is showcased, featuring a spacious bed with a metal frame. A cozy seating area is arranged with patterned cushions and a wooden coffee table. Natural light pours in through multiple windows, illuminating the warm wood flooring and inviting ambiance.
Guest house in West Tisbury
4.97 out of 5 average rating, 101 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
An open studio space features a cozy sleeping area with a spacious bed covered in light bedding. A soft armchair and a wooden bench provide additional seating. Natural light streams in from a window, enhancing the room's bright atmosphere. Shelving displays books and decorative items.
Flat in Oak Bluffs
4.98 out of 5 average rating, 223 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.

Guest favourite
A spacious two-story home is framed by expansive lawns and lush greenery. The exterior features a mix of wood siding and gray roof, while a garden and outdoor seating area enhance the inviting setting. A sunny sky and tree foliage provide a peaceful backdrop.
Home in West Tisbury
4.9 out of 5 average rating, 10 reviews

Pvt Beach, Pickleball, Steps to Wildlife Sanctuary

With bookings already coming in for next summer, don't miss your chance to book early to lock in your ideal dates! Our tranquil spot offers a private association beach and direct access to Cedar Tree Neck Sanctuary, you'll have 300 acres of hiking trails/beaches. Enjoy expansive lawns, a garden, and a converted pickleball court and basketball hoop. Relax on the back patio with a gas grill or prepare a family meal in the fully equipped kitchen. This hidden gem is the road less traveled.

Top guest favourite
The open living area features exposed wooden beams overhead and includes a spacious wooden dining table. Two lounge chairs, a round pouf, and a day bed are arranged for seating. Natural light filters in through large glass doors, leading to an outdoor area.
Guest house in Chilmark
4.99 out of 5 average rating, 106 reviews

4-Season Guest House on Historic Chilmark Estate

Beautiful private guest house in Chilmark on Martha's Vineyard. Secluded yet convenient. Drive on pass to spectacular Chilmark beaches! Newly renovated and gorgeous. Great location - 10 minute walk to Chilmark Store. Full kitchen, living area, kitchen island/dining table, queen bed, day bed (not for sleeping), fireplace/heater, private outdoor shower, deck and picnic table, full bath inside. Keurig machine. 2 friendly labs/2 chickens on premises. Easy bus access. Old-style MV charm.

Superhost
An outdoor patio area is surrounded by lush gardens featuring blooming flowers and greenery. Two blue chairs are positioned near a table underneath a large umbrella, providing a shaded space for relaxation. The backdrop includes a well-maintained building with multiple glass doors.
Flat in Aquinnah
4.71 out of 5 average rating, 28 reviews

Quiet & Serene in Aquinnah

Fall asleep to the sounds of the waves. Unique 1000 sqft. 1st floor suite, surrounded by conservation lands and adjacent to the new 320 acre Squibnocket Pond Reservation. The suite consists of 2 elegantly furnished bedrooms and a large marble bathroom. Three sets of French doors open onto an expansive terrace with gardens. Larger bedroom has a beach stone fireplace with a wood stove. 12 minute walk to private beach. Owner occupied on 2nd floor. Charming and serene. Pet Friendly

Top guest favourite
A bright living area features a large window that allows natural light to fill the space. Comfortable seating includes a gray sofa and a dark blue loveseat. A wooden coffee table sits between them, and a ceiling fan helps maintain a comfortable temperature.
Flat in Bourne
4.98 out of 5 average rating, 123 reviews

Cape Cod Canal Home

Enjoy a getaway in our renovated 2 bedroom apartment on the 2nd floor with air conditioning and front balcony overlooking the Canal in Sagamore Beach. Beautiful, relaxing view with lots of boats and ships passing by. Steps to the Cape Cod Canal Bikeway for biking, walking and fishing. Two miles to Scusset Beach, 15 minutes to Historic Plymouth. Great location for easy day trips to Boston, Provincetown, Hyannis, beaches and more. Perfect for 2 couples or a family of five.

Top guest favourite
A spacious deck features two wooden Adirondack chairs facing a serene waterfront view of Vineyard Sound. Lush greenery surrounds the area, and the calm water reflects the soft hues of the sky, creating a peaceful outdoor setting.
Home in Woods Hole
4.93 out of 5 average rating, 127 reviews

Juniper Point Cottage With Ocean View

Charming Cape Cod cottage on semi-private road with and ocean view of Vineyard Sound. Renovations completed in mid-July, 2020. Three BR, 2 private attached baths, 1 semi-private bath, fully equipped kitchen, patio with BBQ grill, gas fireplace, cable-TV, WiFi internet, large second-floor deck, a/c.. Close to Vineyard Ferry, bus station and town. Seasonal rent. Please complete a reservation request to determine the rent in effect for your requested dates.

Popular amenities for Aquinnah holiday rentals

  1. Airbnb
  2. United States
  3. Massachusetts
  4. Dukes County
  5. Aquinnah