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Chilmark Vacation Rentals

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Vacation Rentals in Chilmark

Private beach nearby, beach bar
The Club at New Seabury
The Club at New Seabury
3.5 star property
9.0 out of 10, Wonderful, (336)
"Nice amenities. "
United States
William
$151 nightly
The price is $173
Nov 4 - Nov 5
Total with taxes and fees
The Club at New Seabury
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.
10.0 out of 10, Exceptional, (87)
"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.
$901 nightly
The price is $1,031
Nov 30 - Dec 1
Total with taxes and fees
Coastal chic meets French Provençal in this newly renovated oceanfront home.
On the beach, white sand
InnSeason Resorts Captain's Quarters
InnSeason Resorts Captain's Quarters
3.5 star property
9.8 out of 10, Exceptional, (189)
"Great place to stay. Close to Island Queen ferry and right by the beach. Would definitely go back!"
United States
Matt
InnSeason Resorts Captain's Quarters
Indoor pool, outdoor pool, sun loungers
Sea Mist Resort
Sea Mist Resort
3.0 star property
8.6 out of 10, Excellent, (140)
"We had a fabulous visit!"
United States
Joelle
$144 nightly
The price is $165
Nov 8 - Nov 9
Total with taxes and fees
Sea Mist Resort
Terrace/patio
Uniquely designed island retreat with fast WiFi & private W/D - dogs welcome
Uniquely designed island retreat with fast WiFi & private W/D - dogs welcome
9.0 out of 10, Wonderful, (34)
"The peaceful woodland setting is just beautiful! Enjoyed a quiet stay in this spacious one bedroom house. The porch wraps around entire house and gave our morning coffee and breakfast a very special vacation feel."
United States
Maryann B.
Uniquely designed island retreat with fast WiFi & private W/D - dogs welcome
Outdoor dining
Newly Renovated Near Amazing Sunset Beach
Newly Renovated Near Amazing Sunset Beach
9.8 out of 10, Exceptional, (73)
"The house is beautiful. It looks just like the pictures. The area around the house is very safe and quiet. The owners are very responsive. They even provided beach towels (which might not be in the description). "
United States
Debbie B.
Newly Renovated Near Amazing Sunset Beach
Exterior
Beach front, fenced yard, dogs welcome, central air, fire pit, 3 kayaks, hot tub
Beach front, fenced yard, dogs welcome, central air, fire pit, 3 kayaks, hot tub
10.0 out of 10, Exceptional, (112)
"The place was beautiful, clean, spacious and the perfect location. There were so many options, from hanging out on the porch, by the fire, on the water front, or inside around the upstairs living room/billiards area downstairs. The owner was an amazing communicator, as she answered all of my questions promptly. I highly recommend this place to anyone!Thank you for an awesome and memorable stay! "
United States
natalia A.
Beach front, fenced yard, dogs welcome, central air, fire pit, 3 kayaks, hot tub
Beach
Cozy getaway in a central location w/ a full kitchen & furnished deck
Cozy getaway in a central location w/ a full kitchen & furnished deck
6.6 out of 10, (24)
"The home was nice, a little outdated, but great for a family. Unfortunately it does not have AC and when we arrived we found 2 fans were broken. We immediately contacted Vacasa who said they would send maintenance. While waiting for maintenance, we also noticed within the first hour that one of the dining chair backs was broken/not attached, one of the bed posts fell off as it was not attached, and the fan in one of the bathrooms was stuck on. We planned to notify maintenance when they came but...
United States
Dawn R.
Cozy getaway in a central location w/ a full kitchen & furnished deck
Exterior
Tranquil Home with Private Deck - Walk to Beaches and Downtown Oak Bluffs
Tranquil Home with Private Deck - Walk to Beaches and Downtown Oak Bluffs
6.4 out of 10, (31)
"It is an old home that has had no updates. It’s shabby- a little bit of a smell and outdated furniture. That being said, it has everything you need and is a good location on the island, especially if you are driving. It was a deal compared to everything else around and was somehow available during summer with less than 2 months before we booked."
United States
Myrtle A.
Tranquil Home with Private Deck - Walk to Beaches and Downtown Oak Bluffs
Seasonal outdoor pool
Beachside Village Resort
Beachside Village Resort
3.0 star property
9.2 out of 10, Wonderful, (100)
"Wonderful location, nice staff!"
United States
Claire
Beachside Village Resort
Fridge, microwave, oven, stovetop
The quintessential MV home. Now booking for 2026!
The quintessential MV home. Now booking for 2026!
9.8 out of 10, Exceptional, (55)
"Beautiful home on quiet street within walking distance to Oak Bluffs. Well equipped kitchen and comfy family room. Beautiful primary suite with huge modern bathroom. Carrington was an excellent host and very responsive to anything that came up. "
United States
Jenny D.
The quintessential MV home. Now booking for 2026!
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.
9.4 out of 10, Exceptional, (91)
"The apartment was awesome with great views of the ocean and a very convenient location to the ferry and shopping."
United States
Stephen
$446 nightly
The price is $498
Nov 4 - Nov 5
Total with taxes and fees
Walking Distance From Oak Bluffs Ferry Terminal With 180 Degree Ocean View.
Interior
Renovated One Bedroom Apartment Downtown Falmouth Minutes From the Beach
Renovated One Bedroom Apartment Downtown Falmouth Minutes From the Beach
2.0 star property
10.0 out of 10, Exceptional, (1)
"The location was great and the pullouts were comfortable. The only downside is the walk through bathroom."
United States
Matthew
Renovated One Bedroom Apartment Downtown Falmouth Minutes From the Beach
Interior
MOST CHIC SPOT! Your Martha's Vineyard Getaway!
MOST CHIC SPOT! Your Martha's Vineyard Getaway!
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 4 - Nov 5
Total with taxes and fees
MOST CHIC SPOT! Your Martha's Vineyard Getaway!
Beach nearby
Ground-Floor Studio w/ 2 King Beds & Kitchenette (103)
Ground-Floor Studio w/ 2 King Beds & Kitchenette (103)
6.0 out of 10, (2)
"Our trip was a last minute decision, and needed to stay just one night. The location, the fast response, clear instructions, cleanliness, assigned parking and pricing all came together very nicely! "
United States
Arpi L.
$155 nightly
The price is $171
Nov 11 - Nov 12
Total with taxes and fees
Ground-Floor Studio w/ 2 King Beds & Kitchenette (103)
Property grounds
Classic Cape Cod - Ocean Views - Steps to Falmouth Heights Beach.
Classic Cape Cod - Ocean Views - Steps to Falmouth Heights Beach.
10.0 out of 10, Exceptional, (52)
"Beautiful home in a great location! "
United States
Maurice R.
Classic Cape Cod - Ocean Views - Steps to Falmouth Heights Beach.
Property grounds
Chappaquiddick retreat-outdoor shower, hot-tub, decks, central AC-close to beach
Chappaquiddick retreat-outdoor shower, hot-tub, decks, central AC-close to beach
10.0 out of 10, Exceptional, (36)
"This house, location, and owners are simply fabulous! Our whole family enjoyed the decorations, the cozy feel and the layout of the house. The owners are very kind and eager to help via text or phone. We will be back next year!"
United States
lea g.
Chappaquiddick retreat-outdoor shower, hot-tub, decks, central AC-close to beach
Beach nearby, sun loungers, beach towels
Falmouth Cape - Walk to Island Queen ferry to Martha's Vineyard, Beach, Downtown
Falmouth Cape - Walk to Island Queen ferry to Martha's Vineyard, Beach, Downtown
10.0 out of 10, Exceptional, (186)
"My daughters and grandchildren enjoyed our stay. The location was ideal for shopping and restaurants We even invited over other relatives from the area to enjoy a cookout and smores.. I would rent this place again."
United States
James B.
Falmouth Cape - Walk to Island Queen ferry to Martha's Vineyard, Beach, Downtown
Property grounds
By the Water - Steps to the Beach - 4Br, AC, Views of Vineyard Sound
By the Water - Steps to the Beach - 4Br, AC, Views of Vineyard Sound
9.8 out of 10, Exceptional, (23)
"Amazing place. Definitely steps from the beach . Also the walk into town was not bad at all. we enjoyed doing that. The house was spacious and clean. Communications were great with the owner Joe. We really enjoyed our stay there. highly recommend the place."
United States
Anonymous traveler
By the Water - Steps to the Beach - 4Br, AC, Views of Vineyard Sound
Property grounds
Updated house close to town and beach with patio, AC, and games
Updated house close to town and beach with patio, AC, and games
2.0 star property
9.8 out of 10, Exceptional, (6)
"Great place, would stay again. Comfortable beds, walking distance to tons, nicely decorated. Had everything we needed."
United States
Margaret C.
Updated house close to town and beach with patio, AC, and games
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

Vineyard Harbor Motel - Private Beach

Vineyard Harbor Motel - Private Beach

10/10 Excellent
"The staff were lovely and very helpful, parking easy and the room was clean. The private beach was lovely and the location of the motel is convenient for the town and good touring the island."
Lisa 2-night trip
Posted 2 days ago
Vineyard Harbor Motel - Private Beach

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 $165 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.

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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 76 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.