House vacation rentals in Chilmark

Find and book unique houses on Airbnb

Top-rated house rentals in Chilmark

Guests agree: these houses are highly rated for location, cleanliness, and more.

0 of 0 items showing

1 of 3 pages

Guest favorite

Home in Mattapoisett

4.95 out of 5 average rating, 132 reviews

*The Cozy Escape* | Historic South Coast Retreat

SAVE (heart) US NOW! Escape to Mattapoisett on the South Coast of MA & experience the charming beauty of this small town! Our recently updated home is a perfect retreat for your getaway. Take in the stunning views of the harbor at Shipyard Park or stroll along the area beaches. Explore the area's history at Neds Point Lighthouse & Salty the Seahorse. Unwind at our cozy & inviting home. Dine in with our fully equipped kitchen or indulge at the many great restaurants! Book your unforgettable stay!

Jun 19 – 26

ﺩ.ﺇ1,173 per night

Guest favorite

Home in West Tisbury

4.98 out of 5 average rating, 122 reviews

Secluded Up Island Cottage

Charming Martha's Vineyard post and beam house on two secluded acres with two bedrooms in West Tisbury. The master bedroom has a queen bed, the second bedroom has a full bed, the loft has a full size futon. It is peacefully tucked away at the end of a road with only three other houses on it. It has easy access to beaches, bike paths and walking trails. Enjoy some family time in the wooded backyard grilling or relaxing with an outdoor shower or napping in the hammock after a day at the beach.

Jan 16 – 23

ﺩ.ﺇ956 per night

Guest favorite

Home in Oak Bluffs

4.93 out of 5 average rating, 169 reviews

Spectacular beach & pool combo; beautiful sunsets!

Close to airport, you’ll love backyard beach, water view, pool/grass yard, ambiance and the outdoors space. Beach & Pool (POOL HEAT STARTS SUMMER, 6/21) is a hard to find combination!! Location is private, yet it's close to the 3 largest towns on Martha's Vineyard. Great for couples, families (with kids), and big groups. Enjoy dinner with the indoor/outdoor Sonos music system during a beautiful sunset! NOTE; Rate increase in high season, pool/spa is a combined unit & ONLY heated in summer!

Mar 8 – 15

ﺩ.ﺇ2,178 per night

Guest favorite

Home in Falmouth

4.97 out of 5 average rating, 237 reviews

The Driftwood Home, 5 min from Mashpee Commons, AC

-1600 square feet, Newly built -Old Silver Beach, South Cape Beach, and Falmouth Heights Beachs all within 15 min drive -Outdoor deck with sectional seating, fire pit, and BBQ grill -5 minutes from Mashpee Commons -Central Air Conditioning -55" smart TV w/ Netflix, Hulu, etc. -Shining Sea Bike Trail 10 min away -Spacious Kitchen w/ all utensils, flatware, and appliances -Falmouth Country Club, Cape Cod Country Club, Quashnet Valley Country Club within 10 minutes -15 min from Falmouth main st.

Aug 8 – 15

ﺩ.ﺇ2,041 per night

Guest favorite

Home in Sandwich

5.0 out of 5 average rating, 154 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.

May 6 – 13

ﺩ.ﺇ2,372 per night

Guest favorite

Home in Dartmouth

4.92 out of 5 average rating, 127 reviews

Serene 3-Bedroom Lakeside Home

Welcome to this serene getaway home located directly on the Lake! This lovely home is peaceful & conveniently located next to I-195 and a short drive away from Boston, Providence, Newport, Cape Cod, many beaches, a winery and a 5 minute drive to UMass Dartmouth. With its private entrance, this cozy home has a fully equipped kitchen, grill, cable/Roku & Wi-Fi, board games and a sunroom overlooking Lake Noquochoke so all you are left to do is bring your kayak, food and you’re ready to relax!

Dec 26 – Jan 2

ﺩ.ﺇ1,083 per night

Guest favorite

Home in Edgartown

4.96 out of 5 average rating, 187 reviews

Brand new gorgeous 2 bedroom guest house.

This is a gorgeous brand new 2 bedroom guest house on the bike path that leads to downtown Edgartown and both State Beach and South Beach, as well as 1/4 of a mile from the famous Morning Glory Farm Stand. There are cathedral ceilings in the living room, which provide a open, spacious feel. There is a large deck on the front of the house with a grill, table and chairs. Part of it is covered in shade. Separate parking for guests with privacy, as it sits 200+ feet from the main house.

Nov 10 – 17

ﺩ.ﺇ590 per night

Guest favorite

Home in Oak Bluffs

4.92 out of 5 average rating, 207 reviews

Unique Luxury Yurt w/ Free kayaking

Step into this unique yurt house! As soon as you walk in, you'll be greeted with a one-of-a-kind experience, from the textured concrete floors to the large circular skylight. Every detail is carefully planned, and you'll have the opportunity to unwind in a spacious private yard. Spend your evenings stargazing, take advantage of complimentary paddling, participate in our scheduled chicken feedings, do yoga in the roomy loft, and revel in the splendor of your exclusive island yurt!

Oct 31 – Nov 7

ﺩ.ﺇ1,072 per night

Guest favorite

Home in New Bedford

4.99 out of 5 average rating, 183 reviews

Historic Cobblestone Carriage House near Downtown

Enjoy a piece of history at this carriage house! Jonathan Bourne owned a mansion along with this home, and his son purchased a whaler, Lagoda, in 1841. The ship is currently displayed at the New Bedford Whaling Museum, which is walking distance; just four/five blocks of downtown New Bedford, where you can also enjoy shopping, great food, entertainment, and the ferry to either Martha’s Vineyard or Nantucket. It’s a cultural diversity in an historic seaside New England location.

Oct 1 – 8

ﺩ.ﺇ1,078 per night

Superhost

Home in Edgartown

4.87 out of 5 average rating, 141 reviews

Martha's Vineyard Vacation Home

My place is close to the Bike Path, Edgartown, South Beach, Katama General Store, Katama Farm, Edgartown Lighthouse, great views. Take the bike path either direction for all of the island's attractions. You’ll love my place because of the Renovated Kitchen, Renovated Bathrooms, Comfortable Furniture, Convenience to Everything, Outdoor Shower, Deck. My place is good for couples, solo adventurers, and families (with kids).

May 14 – 21

ﺩ.ﺇ1,428 per night

Guest favorite

Home in Falmouth

4.94 out of 5 average rating, 111 reviews

Cute Single Family Home in Nice Neighborhood

Hello! We have an adorable two-bedroom (bedrooms are very small), single-family home within walking distance to the beach. (Bristol Beach is 3/10 of a mile away, and Falmouth Heights Beach is 1/2 mile from the house). Perfect for a family of 4 or couples retreat. Please note that the bedrooms are very small and neither of them can accommodate any sort of portable crib, such as a Pack and Play.

May 10 – 17

ﺩ.ﺇ589 per night

Guest favorite

Home in Edgartown

5.0 out of 5 average rating, 116 reviews

Close to Edgartown Village Center!

This 1800 square foot Ranch-style Condo with loft was built in 2018 and is set on a large nicely landscaped lot with plenty of room inside and out. It has 4 bedrooms and sleeps 9. It’s a 20-minute walk to the Edgartown village center, a 10-minute walk to Morning Glory Farm, and just a 10-minute drive to South Beach! All updated furnishings, beds, linens, appliances. Read our reviews! Immaculate!

Oct 26 – Nov 2

ﺩ.ﺇ1,998 per night