A dock with boats, a small wooden structure, and a forested shoreline.

Chilmark Holiday Rentals

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Our top choices for Chilmark holiday rentals

NEW Construction: a Love Letter to Martha's Vineyard

NEW Construction: a Love Letter to Martha's Vineyard
West Tisbury
10.0 out of 10, Exceptional, (2 reviews)
"We had a wonderful stay at this home in West Tisbury. The house was exactly as described - comfortable, clean, well-appointed, and thoughtfully stocked with everything we needed. The location was perfect for exploring the island while still feeling peaceful and relaxing. Jack was incredibly responsive, helpful, and easy to communicate with throughout our stay. We truly felt at home and would gladly stay here again. Highly recommend!"
United States
Nini D.
The price is AU$3,337
includes taxes & fees
3 Aug - 4 Aug
NEW Construction: a Love Letter to Martha's Vineyard

Walk to Beach! Oak Bluffs Home & Studio

Walk to Beach! Oak Bluffs Home & Studio
Oak Bluffs
The price is AU$2,377
includes taxes & fees
2 Aug - 3 Aug
Walk to Beach! Oak Bluffs Home & Studio

The Club at New Seabury

The Club at New Seabury
3.5 star property
New Seabury
9.0 out of 10, Wonderful, (363 reviews)
"The condo had everything we needed, and was clean, however there were a lot of ants on the main floor, mostly in the kitchen. This should definitely be looked into and maybe some traps set. There was a washer/dryer which was great and room service each day to change towels."
Canada
Rylea
The price is AU$824
includes taxes & fees
11 Aug - 12 Aug
The Club at New Seabury

4 Mi to Bristol Beach! Coastal Retreat w/ Pond

4 Mi to Bristol Beach! Coastal Retreat w/ Pond
3.0 star property
East Falmouth
The price is AU$982
includes taxes & fees
14 Aug - 15 Aug
4 Mi to Bristol Beach! Coastal Retreat w/ Pond

4-bedroom house in lovely Edgartown..Centrally located

4-bedroom house in lovely Edgartown..Centrally located
Edgartown
10.0 out of 10, Exceptional, (2 reviews)
"Absolutely incredible stay! The host is so kind and helpful. House was very clean. Truly everything you need inside for cooking and beach fun! PERFECT location really centrally located to both edgartown and oak bluffs. Located in a quiet neighborhood near Felix Neck with lots of walking trails, which was very nice! Could not recommend this place more!"
United States
Katelyn W.
The price is AU$2,000
includes taxes & fees
19 July - 20 July
4-bedroom house in lovely Edgartown..Centrally located

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

Spacious Coastal New Seabury Home - Kayak Launch Across Street! Walk to Beach
New Seabury
10.0 out of 10, Exceptional, (9 reviews)
"Great place"
United States
Aaron Q.
The price is AU$2,083
includes taxes & fees
22 July - 23 July
Spacious Coastal New Seabury Home - Kayak Launch Across Street! Walk to Beach

Backyard Retreat / 5 Min > Beach & Main St

Backyard Retreat / 5 Min > Beach & Main St
Fairhaven
The price is AU$1,516
includes taxes & fees
17 July - 18 July
Backyard Retreat / 5 Min > Beach & Main St

Chappy cottage with private beach

Chappy cottage with private beach
Edgartown
10.0 out of 10, Exceptional, (18 reviews)
"What a gorgeous location, my family and I had a wonderful time on Chappy, will definitely be back!"
United States
Clinton G.
The price is AU$2,175
includes taxes & fees
30 July - 31 July
Chappy cottage with private beach

Contemporary coastal retreat nearby Falmouth beaches! w/ spacious living area

Contemporary coastal retreat nearby Falmouth beaches! w/ spacious living area
Falmouth
10.0 out of 10, Exceptional, (14 reviews)
"This is a beautiful and unique home with plenty of space and activities for the family. The photos were accurate and there was so much space for everyone to relax. We enjoyed our stay so much. "
United States
Lisa F.
The price is AU$1,251
includes taxes & fees
10 Aug - 11 Aug
Contemporary coastal retreat nearby Falmouth beaches! w/ spacious living area

A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!

A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!
Oak Bluffs
9.4 out of 10, Exceptional, (6 reviews)
"This house was perfect for our getaway. Rebecca, the host, was extremely responsive and helpful during our trip. The house was as advertised. It was clean, well equipped, and the location was perfect as well "
United States
Louis R.
The price is AU$1,801
includes taxes & fees
30 July - 31 July
A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!

Ocean view, FREE BEACH PASS. Short drive to multiple beaches and water park!

Ocean view, FREE BEACH PASS. Short drive to multiple beaches and water park!
Fairhaven
9.6 out of 10, Exceptional, (35 reviews)
"We were looking for a weekend away from home, and we're lucky to find this place available. We got great recommendations for places to eat nearby, and were able to enjoy the area. We'd stay here again!"
United States
Zachary S.
The price is AU$731
includes taxes & fees
29 July - 30 July
Ocean view, FREE BEACH PASS. Short drive to multiple beaches and water park!

Chappy - Family Beach House

Chappy - Family Beach House
Edgartown
9.8 out of 10, Exceptional, (16 reviews)
"Sun-filled, comfortable, and perfectly located!"
United States
Carmin R.
The price is AU$1,879
includes taxes & fees
26 July - 27 July
Chappy - Family Beach House

Come Enjoy Cape Cod! Charming 3-BR house in pleasant Falmouth

Come Enjoy Cape Cod! Charming 3-BR house in pleasant Falmouth
Falmouth
9.4 out of 10, Exceptional, (15 reviews)
"Really beautiful place with a lot of space and a very helpful host"
United States
Gokul K.
The price is AU$1,621
includes taxes & fees
22 July - 23 July
Come Enjoy Cape Cod! Charming 3-BR house in pleasant Falmouth

serene wooded 3-bedroom house West Tisbury deck, screen porch and outdoor shower

serene wooded 3-bedroom house West Tisbury deck, screen porch and outdoor shower
West Tisbury
The price is AU$1,309
includes taxes & fees
26 July - 27 July
serene wooded 3-bedroom house West Tisbury deck, screen porch and outdoor shower

LOCATION & QUALITY! Right in town, freshly renovated, near everything u need!

LOCATION & QUALITY! Right in town, freshly renovated, near everything u need!
Tisbury
10.0 out of 10, Exceptional, (59 reviews)
"We loved the location and place was great!"
United States
Eileen M.
The price is AU$1,425
includes taxes & fees
18 July - 19 July
LOCATION & QUALITY! Right in town, freshly renovated, near everything u need!

Relax by Oak Bluffs Harbor, enjoy your 3-bedroom East Chip retreat

Relax by Oak Bluffs Harbor, enjoy your 3-bedroom East Chip retreat
Oak Bluffs
9.8 out of 10, Exceptional, (6 reviews)
"The property was clean, private, and peaceful."
United States
Sherri R.
The price is AU$2,838
includes taxes & fees
29 July - 30 July
Relax by Oak Bluffs Harbor, enjoy your 3-bedroom East Chip retreat

WATERFRONT Downtown Cottage w/ Beach

WATERFRONT Downtown Cottage w/ Beach
Tisbury
10.0 out of 10, Exceptional, (50 reviews)
"Very beautiful, very clean with incredible views of the Vineyard Haven harbor views"
United States
John M.
The price is AU$2,371
includes taxes & fees
16 Aug - 17 Aug
WATERFRONT Downtown Cottage w/ Beach

Small One Bedroom Private Cottage on Large Quiet Property.

Small One Bedroom Private Cottage on Large Quiet Property.
Tisbury
10.0 out of 10, Exceptional, (16 reviews)
"Nice, quaint cottage. Perfect for a couple's getaway! Location was convenient for walking to shops and restaurants."
United States
Randy T.
The price is AU$725
includes taxes & fees
27 July - 28 July
Small One Bedroom Private Cottage on Large Quiet Property.

Walking-distance to town, shops, restaurants & ferry!

Walking-distance to town, shops, restaurants & ferry!
Tisbury
10.0 out of 10, Exceptional, (25 reviews)
"I rented this for my staff, and they said it was the best place they have stayed on Martha's Vineyard."
United States
else r.
The price is AU$1,439
includes taxes & fees
22 July - 23 July
Walking-distance to town, shops, restaurants & ferry!

Cozy Cottage walk to Menauhant Beach

Cozy Cottage walk to Menauhant Beach
East Falmouth
8.6 out of 10, Excellent, (7 reviews)
"It was a great weekend spot. Had everything we needed, nicely decorated, and in a great and private location"
United States
Grace P.
Cozy Cottage walk to Menauhant Beach
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

Find out more about Chilmark

Everything you need to know about Chilmark holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Chilmark holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Chilmark holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Chilmark holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Chilmark holiday rentals we have selected for you start as low as AU$824 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Chilmark rentals

At Expedia, we put the best Chilmark holiday 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 holiday.

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. 

Frequently asked questions

Can I find holiday rentals in Chilmark?

Yes, there are holiday rentals in Chilmark close to Chilmark Chocolates, or you can select a more secluded option if you're looking for a relaxing stay. 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 holiday rentals that Chilmark has to offer?

Private Hilltop Chilmark Estate with private tennis court, gym and hot tub: This highly rated holiday home rental in Chilmark offers a fireplace, a garden and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Make the most of games in this rental home to help you unwind.

How many holiday rentals are there in Chilmark?

Choose from 67 Expedia holiday rentals in Chilmark for a memorable holiday.

What’s there to see and do in Chilmark?

Family-friendly attractions include Chilmark Chocolates and Fulling Mill Brook Preserve, whereas Menemsha Beach and Edys Island 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 holiday rental in Chilmark like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Chilmark. Holiday rentals provide amenities such as patios, hot tubs and fire pits so you'll be comfy for your stay. If you're concerned about cleanliness, holiday rentals can offer a sense of safety away from shared hotel lifts and busy concierge desks while still allowing you a great travel experience. You'll also have more space in a holiday rental than in a traditional hotel, which makes a holiday rental a great option for a small group gathering.