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Chilmark Vacation Rentals

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In two weeks
Nov 28 - Nov 30
In two months
Jan 9 - Jan 11
In three months
Feb 6 - Feb 8
In four months
Mar 6 - Mar 8

Vacation Rentals in Chilmark

Private beach nearby, beach bar
The Club at New Seabury

The Club at New Seabury

3.5 star property
Mashpee
9.0 out of 10, Wonderful, (337)
"Great stay! Didn't notice it being dated or dirty at all like some reviews said. We loved it!"
United States
Rachael
$142 nightly
The price is $162
Nov 16 - Nov 17
Total with taxes and fees
The Club at New Seabury
Marina
Charming cottage overlooking the bay in Padanaram Village.

Charming cottage overlooking the bay in Padanaram Village.

2.0 star property
Dartmouth
10.0 out of 10, Exceptional, (10)
"Beautiful property. The cottage is beautifully decorated and well maintained. Amazing location. Host was very good at communicating. "
United States
christine l.
$336 nightly
The price is $375
Nov 17 - Nov 18
Total with taxes and fees
Charming cottage overlooking the bay in Padanaram Village.
Fridge, microwave, oven, stovetop
Located Steps Away To Main Street And .7 Miles From Surf Drive Beach

Located Steps Away To Main Street And .7 Miles From Surf Drive Beach

Falmouth
10.0 out of 10, Exceptional, (207)
"The house was even nicer than the pictures. We came in March for a long weekend with some friends and had a really great time. Walking distance to so many fun things- great house for all ages!"
United States
Briget R.
$433 nightly
The price is $496
Nov 16 - Nov 17
Total with taxes and fees
Located Steps Away To Main Street And .7 Miles From Surf Drive Beach
Outdoor dining
Newly Renovated Martha's Vineyard Vacation Rental!

Newly Renovated Martha's Vineyard Vacation Rental!

Katama
9.6 out of 10, Exceptional, (47)
"Very nice house that served our needs. Well located. Nicely appointed. The bedroom downstairs with twin beds accommodated my elderly mother who has trouble with stairs. No real maintenance issues other than, the gfci outlets in the bathrooms did not work."
United States
Silvia B.
$533 nightly
The price is $595
Nov 15 - Nov 16
Total with taxes and fees
Newly Renovated Martha's Vineyard Vacation Rental!
Beach nearby, beach towels
☼ Westport Point ☼ beach house on 1/2 acre easy access to beach/historic village

☼ Westport Point ☼ beach house on 1/2 acre easy access to beach/historic village

Westport
9.8 out of 10, Exceptional, (22)
"We enjoyed our stay and recommend It. Delightful back yard and patio area and a very pleasant front porch."
United States
Alan M.
$377 nightly
The price is $414
Nov 17 - Nov 18
Total with taxes and fees
☼ Westport Point ☼ beach house on 1/2 acre easy access to beach/historic village
Terrace/patio
The Seashell Cove - Martha's Vineyard

The Seashell Cove - Martha's Vineyard

Katama
9.8 out of 10, Exceptional, (23)
"My family and I had a great stay in this lovely home!! The house had everything we needed and was a great starting point for all island adventures. Charles was so helpful throughout the entire trip. We would most certainly stay here again!"
United States
Caryn I.
$514 nightly
The price is $574
Dec 1 - Dec 2
Total with taxes and fees
The Seashell Cove - Martha's Vineyard
Game room
Spring Escape in Hatchville – Sleeps 6 + Dogs!

Spring Escape in Hatchville – Sleeps 6 + Dogs!

Falmouth
10.0 out of 10, Exceptional, (11)
"We LOVED our stay. The home is gorgeous and comfortable with everything we needed. The kids loved the game barn. Nicely located. We loved the deck. Would stay again!"
United States
Enid G.
$630 nightly
The price is $721
Nov 15 - Nov 16
Total with taxes and fees
Spring Escape in Hatchville – Sleeps 6 + Dogs!
Interior
Charming studio in tranquil Falmouth with AC

Charming studio in tranquil Falmouth with AC

Falmouth
$173 nightly
The price is $197
Nov 15 - Nov 16
Total with taxes and fees
Charming studio in tranquil Falmouth with AC
Fridge, microwave, oven, stovetop
NEW! Renovated Family-Friendly Vineyard Haven Home, Close to town!

NEW! Renovated Family-Friendly Vineyard Haven Home, Close to town!

Tisbury
10.0 out of 10, Exceptional, (16)
"The house is beautiful and conveniently located. The host, Melissa, was accessible and super helpful. We thoroughly enjoyed our time here and hope to be back in the future."
United States
Betel G.
$971 nightly
The price is $1,085
Dec 1 - Dec 2
Total with taxes and fees
NEW! Renovated Family-Friendly Vineyard Haven Home, Close to town!
5 bedrooms, desk, iron/ironing board, travel crib
Coastal chic meets French Provençal in this newly renovated oceanfront home.

Coastal chic meets French Provençal in this newly renovated oceanfront home.

East Falmouth
10.0 out of 10, Exceptional, (88)
"This is a lovely property for a family beach vacation! The property has a wonderful view of the ocean, easy access to a beach, and is close to many great restaurants and things to do. Our host was very responsive and accommodating throughout our stay. I would highly recommend. "
United States
Andrew H.
$888 nightly
The price is $1,016
Dec 8 - Dec 9
Total with taxes and fees
Coastal chic meets French Provençal in this newly renovated oceanfront home.
Smart TV
Walking Distance From Oak Bluffs Ferry Terminal with 180 Degree Ocean View

Walking Distance From Oak Bluffs Ferry Terminal with 180 Degree Ocean View

Oak Bluffs
9.4 out of 10, Exceptional, (88)
"We loved our stay! It was the perfect location, loved the view, it was sparce but clean. Check in/out was easy and owner was responsive. "
United States
Tracy M.
$446 nightly
The price is $498
Nov 15 - Nov 16
Total with taxes and fees
Walking Distance From Oak Bluffs Ferry Terminal with 180 Degree Ocean View
TV, fireplace, books
A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!

A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!

Oak Bluffs
9.0 out of 10, Wonderful, (2)
"The house was lovely. Very clean and orderly. Beautiful back porch that we enjoyed very much. The beds were very comfortable. Our only complaint was the Master bathroom needs some updating. The shower head desperately needs to be changed and the lighting is extremely poor. Also, only 1 half size mirror on the whole first floor. Other than that, it was perfect."
United States
Leon R.
$800 nightly
The price is $894
Nov 15 - Nov 16
Total with taxes and fees
A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!
Outdoor dining
Cape Cod Escape at Casa de Leo!

Cape Cod Escape at Casa de Leo!

2.5 star property
Falmouth
$1,266 nightly
The price is $1,448
Nov 16 - Nov 17
Total with taxes and fees
Cape Cod Escape at Casa de Leo!
4 bedrooms, desk, iron/ironing board, travel crib
Scenic 4BR/3BA Waterfront Getaway with private dock, kayaks & Stunning Views

Scenic 4BR/3BA Waterfront Getaway with private dock, kayaks & Stunning Views

Dartmouth
10.0 out of 10, Exceptional, (13)
"Extremely well designed extremely comfortable and well appointed. Beautiful scenery, and very relaxing."
United States
David J.
$1,221 nightly
The price is $1,364
Nov 26 - Nov 27
Total with taxes and fees
Scenic 4BR/3BA Waterfront Getaway with private dock, kayaks & Stunning Views
Fridge, microwave, oven, stovetop
Spacious Coastal New Seabury Home - Kayak Launch Across Street! Walk to Beach

Spacious Coastal New Seabury Home - Kayak Launch Across Street! Walk to Beach

Mashpee
10.0 out of 10, Exceptional, (8)
"We had a great time in this rental. The house is a perfect set up for families and/or friends with bedrooms on lower level, and two en-suite masters. The location is perfect. Walking distance to a beach and beautiful neighborhood. Views of the water on the second floor balconies. Would rent again!"
United States
Michelle A.
$995 nightly
The price is $1,139
Nov 15 - Nov 16
Total with taxes and fees
Spacious Coastal New Seabury Home - Kayak Launch Across Street! Walk to Beach
Interior
MOST CHIC SPOT! Your Martha's Vineyard Getaway!

MOST CHIC SPOT! Your Martha's Vineyard Getaway!

Oak Bluffs
10.0 out of 10, Exceptional, (7)
"This home is truly that, a welcoming escape nestled in the woods. It’s elevated beach-style furnishings feel hand-picked. We traveled with a 14 month old — the house had high-quality baby must haves, pack and play and high chair. We had the pleasure of a responsive host and caretaker. Close to trails, YMCA and the island’s top attractions … !highly recommend!"
United States
Kerry-Ann H.
$1,085 nightly
The price is $1,212
Nov 15 - Nov 16
Total with taxes and fees
MOST CHIC SPOT! Your Martha's Vineyard Getaway!
Exterior
Cape cod getaway Close to Old Silver

Cape cod getaway Close to Old Silver

Falmouth
$457 nightly
The price is $523
Nov 19 - Nov 20
Total with taxes and fees
Cape cod getaway Close to Old Silver
Terrace/patio
Stones Throw Waterfront

Stones Throw Waterfront

Dartmouth
8.8 out of 10, Excellent, (6)
"According to the listing, the property has AC. That is not true. It had a tiny portable unit that wasn't on when we entered and didn't cool once it was turned on. It also had a window unit that had no place to plug in. There were bugs in multiple areas. The property was not habitable, so we ended up booking a hotel room in a nearby town. VRBO compensated us partially but the owner was unwilling to refund any of our money even though we did not stay in the property. "
United States
Ashley R.
$578 nightly
The price is $645
Nov 15 - Nov 16
Total with taxes and fees
Stones Throw Waterfront
Interior
Walking Distance From Oak Bluffs Ferry Terminal With 180 Degree Ocean View.

Walking Distance From Oak Bluffs Ferry Terminal With 180 Degree Ocean View.

Oak Bluffs
9.4 out of 10, Exceptional, (91)
"Location, the water view, delicious restaurants nearby. Apt was comfy, clean. For 1 night only used the fridge. "
United States
Brenda M.
$446 nightly
The price is $498
Nov 15 - Nov 16
Total with taxes and fees
Walking Distance From Oak Bluffs Ferry Terminal With 180 Degree Ocean View.
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Chilmark Hotel Reviews

Admiralty Inn & Suites - a Red Collection Hotel

Admiralty Inn & Suites - a Red Collection Hotel

10/10 Excellent
"Everything was perfect for me"
Ketia 4-night trip
Posted 3 days ago
Admiralty Inn & Suites - a Red Collection Hotel

Find out more about Chilmark

Everything you need to know about Chilmark vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Chilmark vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Chilmark vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Chilmark vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Chilmark. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Chilmark in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $162 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Chilmark rentals

At Expedia, we put the best Chilmark vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Chilmark rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Chilmark vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Chilmark. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

Frequently asked questions

Can I find vacation rentals in Chilmark?

Yes, there are vacation rentals in Chilmark near Chilmark Chocolates, or you can select a more secluded option if you're looking for extra privacy while you relax. Chilmark is known for its beaches and wineries. Make sure you have time to check out the festivals and local tours during your trip.

What are some of the best vacation rentals that Chilmark has to offer?

Newly Renovated Near Amazing Sunset Beach: This vacation home near Chilmark offers a patio, a garden, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 5 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a selection of games.

How many vacation rentals are there in Chilmark?

Choose from 77 Expedia vacation rentals in Chilmark for a memorable vacation.

What’s there to see and do in Chilmark?

Family-friendly attractions include Chilmark Chocolates and Fulling Mill Brook Preserve, whereas Menemsha Beach and Lucy Vincent Beach are a couple of great spots to enjoy the outdoors. While here, Chilmark Town Hall and Chilmark Public Library are other places worth a visit.

What’s a vacation rental in Chilmark like?

A vacation rental is a private property where you can stay for a long or short time in Chilmark. Vacation rentals offer amenities such as laundry facilities and kitchens so you'll be comfy for your stay. If you're concerned about cleanliness, a vacation rental can offer a sense of security away from shared hotel elevators and lobbies bustling with people while still allowing you the excitement and enjoyment of travel. You'll also get more space in a vacation rental than in a hotel, which makes a vacation rental an attractive option for a family getaway.