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Chilmark Holiday Rentals

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Holiday Rentals in Chilmark

Secluded Guest House overlooking Menemsha Pond. Dogs welcome + Lvl2 EV charger.

10.0 out of 10, Exceptional, (53)
"We were in town for a wedding in Chilmark and the property was exactly what we needed!"
Secluded Guest House overlooking Menemsha Pond. Dogs welcome + Lvl2 EV charger.

The Club at New Seabury

3.5 star property
9.0 out of 10, Wonderful, (327)
"Nice amenities. "
The Club at New Seabury

InnSeason Resorts Captain's Quarters

3.5 star property
9.8 out of 10, Exceptional, (176)
"Just a quick weekend away. Great location for beach lovers. Also excellent retaurants "
InnSeason Resorts Captain's Quarters

Sea Mist Resort

3.0 star property
8.8 out of 10, Excellent, (134)
"Great resort with suites, very cosy with great amenities, close to excellent beach and shopping."
The price is AU$322
includes taxes & fees
15 Sept - 16 Sept
Sea Mist Resort

Beachside Village Resort

3.0 star property
9.2 out of 10, Wonderful, (99)
"Great location! Nice property! "
Beachside Village Resort

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

10.0 out of 10, Exceptional, (85)
"Great stay! "
Coastal chic meets French Provençal in this newly renovated oceanfront home.

Near Old Silver Beach Falmouth-Private entrance, private bedroom & shared bath

8.4 out of 10, Very good, (20)
"So turn key and perfect for Month, Joy is an exceptional host and I’d recommend her place anytime"
The price is AU$275
includes taxes & fees
8 Sept - 9 Sept
Near Old Silver Beach Falmouth-Private entrance, private bedroom & shared bath

Southcape Resort Mashpee a Ramada by Wyndham

3.0 star property
8.6 out of 10, Excellent, (201)
"Enjoyed our stay."
Southcape Resort Mashpee a Ramada by Wyndham

Tranquil Home with Private Deck - Walk to Beaches and Downtown Oak Bluffs

6.2 out of 10, (24)
"The property is quiet, spacious and was within a walkable mile of downtown Oak Bluffs. The beds were comfortable. Plenty of clean linens and towels. The house could use some updating. The coffee maker, drinking glasses, and silverware need to be replaced with cleaner ones. And the torn portions of the sectional couch should be fixed. I would definitely stay at the property again."
Tranquil Home with Private Deck - Walk to Beaches and Downtown Oak Bluffs

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

9.4 out of 10, Exceptional, (84)
"Close to buses, restaurants and ferries. 10/10, we would stay again."
The price is AU$986
includes taxes & fees
10 Sept - 11 Sept
Walking Distance From Oak Bluffs Ferry Terminal With 180 Degree Ocean View.

Relax & Unwind this Fall, at a very private & relaxing 1 bedroom 1 bath studio

10.0 out of 10, Exceptional, (8)
Relax & Unwind this Fall, at a very private & relaxing 1 bedroom 1 bath studio

Amazing Views!!! Sunsets!!! Larger Roof Deck!!! Historic Martha’s Vineyard Gem!!

9.6 out of 10, Exceptional, (40)
"Fantastic beach cabin in a nice location, close to Gay Head lighthouse and several beaches, including the dog-friendly Lobsterville. Good views, plenty of land, we had a good time!"
Amazing Views!!! Sunsets!!! Larger Roof Deck!!! Historic Martha’s Vineyard Gem!!

Renovated Nantucket Style 2 Bed/2 Bath Cottage, Steps to Private Beach, Market..

8.6 out of 10, Excellent, (44)
"Great place for a summer vacation"
Renovated Nantucket Style 2 Bed/2 Bath Cottage, Steps to Private Beach, Market..

Walking to the beach. Bars and Restaurants.

9.6 out of 10, Exceptional, (4)
"The home was very nice and in a convenient location. Ana was very helpful and quick with communications during our stay. Would highly recommend for anyone traveling to Oak Bluffs! "
Walking to the beach. Bars and Restaurants.

Maushop Village-Exceptional, 2 bedrooms, Sleeps 4, 1.5 baths, with great views.

10.0 out of 10, Exceptional, (29)
"We had a great trip and look forward to staying there again. Location is the best part!"
The price is AU$982
includes taxes & fees
17 Sept - 18 Sept
Maushop Village-Exceptional, 2 bedrooms, Sleeps 4, 1.5 baths, with great views.

The Costal Corner - Martha's Vineyard

2.0 star property
10.0 out of 10, Exceptional, (1)
"This property was great for our golf trip. The 3 bedrooms were exceptional "
The Costal Corner - Martha's Vineyard

Oceanview 2 Double Bed Groundfloor Suite

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! "
The price is AU$358
includes taxes & fees
10 Sept - 11 Sept
Oceanview 2 Double Bed Groundfloor Suite

Walk to Beach & Lighthouse: Oak Bluffs Studio!

7.4 out of 10, Good, (3)
"Very accommodating early check in and great communication "
The price is AU$638
includes taxes & fees
2 Sept - 3 Sept
Walk to Beach & Lighthouse: Oak Bluffs Studio!

Waterfront Home w/ Guest Cottage

10.0 out of 10, Exceptional, (2)
"Great property. Very responsive hosts. Thank you!"
Waterfront Home w/ Guest Cottage

Private cottage nestled in center of the Vineyard

10.0 out of 10, Exceptional, (50)
"This whole experience was better than I could have imagined. The cottage was beautiful in a perfect setting. my Hosts went the extra distance. I didn't arrive until close to midnight. My hosts had left fruit, salad, yogurt and ice cream for me. Since I was unable to get a rental car this meant I had something to eat in the morning. I will definitely stay there again! "
Private cottage nestled in center of the Vineyard
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

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$275 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?

Tranquil Home with Private Deck - Walk to Beaches and Downtown Oak Bluffs: This holiday home rental outside of Chilmark offers a patio, a BBQ and air conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave.

How many holiday rentals are there in Chilmark?

Choose from 74 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 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 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.