House vacation rentals in Chilmark

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Top-rated house rentals in Chilmark

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Guest favorite

A spacious living area is showcased with light-toned hardwood floors and ample natural light from large glass doors. Comfortable seating arrangements include a soft gray sofa and wooden dining chairs around a simple table. Coastal decor enhances the relaxed atmosphere, complemented by a mounted flat screen TV.

Home in Hyannis Port

4.87 out of 5 average rating, 149 reviews

Cottage with private beach in Hyannis Port

Make your Cape Cod trip unforgettable in this Exclusive Harbor Village Cottage located right in Hyannis! Enjoy this recently updated 2-bed, 2-bath vacation home with access to private beach, beautiful outdoor deck, and peaceful ocean views. Follow the beach path 900 feet to the beach! Only minutes from downtown Main Street, the Melody Tent and Hyannis harbor. Whether you spend your days exploring the Cape, sunbathing on the beach, or relaxing on the deck, you will be sure to love this house!!!

Guest favorite

An open kitchen and dining area features modern appliances and a central island with seating. Sunlight streams through large windows, illuminating the space. Light-colored cabinetry complements the warm wooden flooring, while pendant lighting adds a contemporary touch.

Home in Oak Bluffs

4.8 out of 5 average rating, 81 reviews

Martha's Vineyard house near Lagoon Pond Beach

Walking distance to Lagoon Pond public beach. New kitchen, 2or3 bedrooms with queen beds, 2-3 baths with showers plus outdoor shower. Sleeping Loft with single bed. Walk or ride a bike to downtown Oak Bluffs. Back yard with sitting area, new covered porch/BBQ. Wifi/AC/laundry. No smoking in house. No pets. Images are a bit dated. The 2nd bathroom has been updated. Before booking, if you have no previous reviews on Airbnb, send us a message introducing yourself and tell us about your trip.

Guest favorite

A light-filled living area features a cozy layout with two soft sofas adorned with decorative pillows. A wood coffee table sits in the center, complemented by a decorative plant. The blue walls and natural light from a skylight enhance the inviting ambiance.

Home in Mashpee

4.92 out of 5 average rating, 134 reviews

Cape Cod; John’s Pond beach w/2 kayaks -SuperHost!

Welcome to our Cape house! Amazing neighborhood & the perfect spot to explore the Cape. Located on fully recreational John's Pond with your private association beach at the end of the street. Large sandy beach, boat launch, float, playground and tennis courts - plus enjoy use of our two kayaks! Just 10 min to South Cape ocean Beach & Mashpee Commons. The house is FULLY updated with hardwoods throughout, AC's, laundry room, front deck with views, private back patio with fire pit and patio.

Superhost

The exterior of the house showcases a wooden facade framed by lush greenery. A large wooden deck extends from the back, furnished with chairs, ideal for relaxation. Sunlight filters through the trees, highlighting the serene outdoor space.

Home in Yarmouth Port

4.88 out of 5 average rating, 153 reviews

* Walk to the beach - Swiss Beach House! *

Walk to the beach! Less than a 1/2 mile (0.7 km)! Perfect spot for paddle boarding. Paddleboards and gas grill (available in summer). Private European - style house. Rustic charm. Laid-back atmosphere. 3 Bedroom, 2.5 bathroom. Comfortably sleeps 6-7, up to 8. Fire pit. Outdoor shower. Farm table for group dining. Fantastic central Cape Cod location. Natural environment. 15 min. to Hyannis for ferries to Nantucket or Martha's Vineyard. Enjoy something unique. Experience the real Cape Cod.

Superhost

A spacious living area features a large sectional sofa and a round coffee table on a decorative rug. Natural light illuminates the space from nearby windows. A staircase leads to the upper level, and the kitchen is visible in the background with modern appliances.

Home in Hyannis Port

4.93 out of 5 average rating, 14 reviews

New dog-friendly 5-BR home. Steps from the beach!

New Luxury home, 500 yards to warm Nantucket Sound Beaches, AC, WiFi, Linens, deck, fully fenced, parking 4 cars, dog allowed The house is excellent for several families vacationing together. There is a one spacious master bedroom suit (king size bed) with a full bathroom on the first floor. The second floor features four bedrooms and two full bathrooms. Two bedrooms has two queen size beds another two bedrooms has 4 twins.

Top guest favorite

A bright living area features large glass doors that open to a deck, inviting natural light. Hardwood floors complement a dark leather sofa and a wood coffee table. Nearby, a dining area includes a small table and chairs, creating an open and airy atmosphere.

Home in New Seabury

5 out of 5 average rating, 11 reviews

Dreamy house in the woods. 3bdr/6beds/2.5ba

Welcome to our sun-drenched, newly updated New Seabury getaway with 3+ br, 2.5 baths and an outdoor shower. 15-minute walk/3-minute bike ride to the Spit beach. Short drive or a scenic walk to the Popponesset Inn/Marketplace. Enjoy our big private backyard setup with a hammock, patio and a cozy fire-pit. Relax on our expansive wrap-around deck equipped with a 4-burner Weber grill, dining furniture, and a patio set.

Superhost

A charming yellow house is surrounded by lush greenery and flowering trees. A well-maintained lawn enhances the appearance of the property, while large windows provide natural light. A pathway leads to the entrance, flanked by decorative shrubs.

Home in West Falmouth

4.9 out of 5 average rating, 48 reviews

Cape Cod's Best Winter Getaway / Hidden Gem

Nestled amidst snow-draped trees, a winter getaway house stands like a hidden gem in a sea of white. Its charming open concept and stone hearth exude a warmth that beckons, a refuge from the biting chill. Inside, the crackle of a glowing fireplace mingles with the scent of pine and hot cocoa. Here, time slows, and the world melts away, leaving only peace, comfort, and the hush of a winter wonderland.

Superhost

A single-story coastal home is shown, featuring a light blue exterior complemented by a gray roof and a brick chimney. Large windows allow natural light to fill the space. A well-maintained front yard includes shrubs and a stone walkway leading to the front door.

Home in Dennis Port

4.8 out of 5 average rating, 56 reviews

Walk to Sea St. beach & restaurants - Cape Cod 👙⛱

Relax and unwind in this updated 4-bedroom, 2-bath coastal home in the heart of Dennisport. With space for 10 people, beachy decor, and plenty of outdoor space—including a brick patio with built-in firepit, and outdoor shower—it’s perfect for families and groups. Walk to multiple beaches, Ocean House Restaurant, and Sunday School Ice Cream. New England charm and modern comfort, all in one!

Guest favorite

Home in Hyannis Port

5 out of 5 average rating, 5 reviews

Townhouse on the beach, pool, walk to Main St.

Bright and sunny, beautifully furnished townhouse in oceanfront Yachtsman resort in Hyannis. 3 bedrooms, 3 1/2 bath, bonus room on the lower level. Amazing ocean view, private deck. Private beach, meticulously landscaped grounds. Walk to private beach, Hyannis marina, historic Main St. Breathtaking ocean views! Pool is open Memorial day to Labor day and only on weekends in June.

Top guest favorite

A freshly renovated house is depicted with a well-maintained facade. The exterior features light-colored siding and multiple large windows. A paved driveway leads to the entrance, bordered by a neatly manicured lawn and stone pathway, while a white fence encloses the property.

Home in West Yarmouth

5 out of 5 average rating, 9 reviews

Cape Escape House

Beautiful freshly renovated house . Your family will be close to everything when you stay at this centrally-located place. Short walk to the beach with playground and access to public boat launch ramp. Walk to restaurants, coffee shop, liquor superstore and local shopping plaza. Located on a quiet street with plenty of parking. Fenced in backyard with patio and grill.

Guest favorite

Home in Dennis Port

4.88 out of 5 average rating, 17 reviews

The Beach Bungalow I Guest Favorite I

This recently renovated family home in West Harwich is a perfect Cape Cod escape. Just 0.3 miles from the beach and downtown Dennis Port, it sleeps 6 comfortably. The home offers privacy and quiet yet is conveniently close to everything the Cape has to offer. With its modern amenities and prime location, this family home promises a memorable Cape Cod vacation.

Superhost

An outdoor seating area features a round table surrounded by several cushioned chairs on a blue area rug. Green decorative pillows add a pop of color, while trees provide a natural backdrop in a peaceful setting. The railings enhance the open, inviting space.

Home in East Falmouth

4.92 out of 5 average rating, 13 reviews

Jaws House - Great Harbors

Your family will be close to everything when you stay at this centrally-located place. This fully renovated ranch is close to beaches and Great Bay. Downtown shopping is a 10 minute drive away. If you like to golf there are 5 golf courses within 20 minutes of the home. Great community neighborhood with a clubhouse, pool, and tennis courts.