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

Chilmark Vacation Rentals

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Check prices for these dates

In two weeks
4 Sep - 6 Sep
In two months
16 Oct - 18 Oct
In three months
13 Nov - 15 Nov
In four months
11 Dec - 13 Dec

Our top choices for Chilmark vacation rentals

Outdoor pool, a heated pool

1. Cozy efficiency apartment/heated pool

Cozy efficiency apartment/heated pool
Chilmark
9.6 out of 10, Exceptional, (24 reviews)
"This is a great property for an individual or a couple looking to explore the island!"
United States
Jillian G.
The price is AED 1,194
AED 1,875 total
includes taxes & fees
15 Sep - 16 Sep
Cozy efficiency apartment/heated pool
Exterior

2. 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 AED 1,157
AED 2,884 total
includes taxes & fees
17 Sep - 18 Sep
serene wooded 3-bedroom house West Tisbury deck, screen porch and outdoor shower
TV, fireplace, books

3. A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!

A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!
Oak Bluffs
9.6 out of 10, Exceptional, (9 reviews)
"The host was very responsive.We definitely recommend this house as family friendly."
United States
Karen M.
The price is AED 1,157
AED 3,085 total
includes taxes & fees
11 Sep - 12 Sep
A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!
Interior

4. MOST CHIC SPOT! Your Martha's Vineyard Getaway!

MOST CHIC SPOT! Your Martha's Vineyard Getaway!
Oak Bluffs
9.8 out of 10, Exceptional, (12 reviews)
"TLDR: House is nice,"
United States
Rachel
The price is AED 4,958
AED 8,066 total
includes taxes & fees
8 Sep - 9 Sep
MOST CHIC SPOT! Your Martha's Vineyard Getaway!
Interior

5. Cozy studio with water views. AC,WiFi, full kitchen, private entrance and patio.

Cozy studio with water views. AC,WiFi, full kitchen, private entrance and patio.
Tisbury
10.0 out of 10, Exceptional, (6 reviews)
"Beautiful view of the lagoon; ideal place for a couple or single. Leisurely walk to town and close to public transportation."
United States
Adrienne W.
The price is AED 1,910
AED 2,999 total
includes taxes & fees
28 Aug - 29 Aug
Cozy studio with water views. AC,WiFi, full kitchen, private entrance and patio.
Property grounds

6. Lovely two bedroom apartment with indoor fireplace

Lovely two bedroom apartment with indoor fireplace
Oak Bluffs
10.0 out of 10, Exceptional, (7 reviews)
"Great stay, flexible and responsive host. Difficult location, however, as it was not centrally located or easy to access transportation, etc."
United States
Aviva M.
The price is AED 731
AED 2,761 total
includes taxes & fees
7 Sep - 8 Sep
Lovely two bedroom apartment with indoor fireplace
Coffee/tea maker, fridge, microwave, oven

7. Brand New Guest house

Brand New Guest house
Oak Bluffs
10.0 out of 10, Exceptional, (6 reviews)
"This is a new, beautiful and tastefully decorated 2 bedroom one bathroom house with a really nice big yard. Owner was very responsive and We had everything we needed for an enjoyable stay!"
United States
Elizabeth O.
The price is AED 1,506
AED 3,742 total
includes taxes & fees
7 Sep - 8 Sep
Brand New Guest house
Interior

8. Brand new! Lovely apartment-Vineyard Haven

Brand new! Lovely apartment-Vineyard Haven
Tisbury
9.8 out of 10, Exceptional, (30 reviews)
"Lovely and all brand new accommodation's that are clean and comfy! A quiet location too! "
United States
Nancy K.
The price is AED 734
AED 1,665 total
includes taxes & fees
27 Aug - 28 Aug
Brand new! Lovely apartment-Vineyard Haven
Exterior

9. Beautiful Estate with salt water pool & pond with kayaks

Beautiful Estate with salt water pool & pond with kayaks
Oak Bluffs
10.0 out of 10, Exceptional, (1 review)
"I can’t say enough about this beautiful property. pictures don’t do any justice for this piece of heaven. The flowers were everywhere , it’s so apparent that the property owners take such pride in this beautiful property. The place was spotless when we walked in the door. We met the owners on arrival , they surprised us with a beautiful ballon to celebrate my 50th birthday. My family enjoyed the pool and the fun Tiki. The outdoor fireplace was inviting after the sun went down. I was a little...
United States
Miriam D.
The price is AED 9,182
AED 13,194 total
includes taxes & fees
13 Sep - 14 Sep
Beautiful Estate with salt water pool & pond with kayaks
Smart TV, fireplace, books, printers

10. Entire cottage, walk to/from ferry & downtown, newly renovated, parking on site

Entire cottage, walk to/from ferry & downtown, newly renovated, parking on site
Tisbury
10.0 out of 10, Exceptional, (40 reviews)
"Great place, awesome location!"
United States
Connor B.
The price is AED 3,118
AED 3,971 total
includes taxes & fees
6 Sep - 7 Sep
Entire cottage, walk to/from ferry & downtown, newly renovated, parking on site
Coffee/tea maker, fridge, microwave, oven

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

Walking-distance to town, shops, restaurants & ferry!
Tisbury
10.0 out of 10, Exceptional, (26 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 AED 3,302
AED 4,160 total
includes taxes & fees
20 Aug - 21 Aug
Walking-distance to town, shops, restaurants & ferry!
Terrace/patio

12. WATERFRONT Downtown Cottage w/ Beach

WATERFRONT Downtown Cottage w/ Beach
Tisbury
10.0 out of 10, Exceptional, (53 reviews)
"Very beautiful, very clean with incredible views of the Vineyard Haven harbor views"
United States
John M.
The price is AED 3,306
AED 4,862 total
includes taxes & fees
20 Aug - 21 Aug
WATERFRONT Downtown Cottage w/ Beach
Sun loungers, beach towels

13. Charming Vacation Home in Oak Bluffs.

Charming Vacation Home in Oak Bluffs.
Oak Bluffs
The price is AED 1,833
AED 3,512 total
includes taxes & fees
8 Sep - 9 Sep
Charming Vacation Home in Oak Bluffs.
Property grounds

14. New 4 BR house near center and beaches with bikes

New 4 BR house near center and beaches with bikes
Katama
10.0 out of 10, Exceptional, (8 reviews)
"Wonderful home in a beautiful neighborhood. Loved our stay!"
United States
Susan M.
The price is AED 1,947
AED 5,305 total
includes taxes & fees
7 Sep - 8 Sep
New 4 BR house near center and beaches with bikes
Exterior

15. The Costal Corner - Martha's Vineyard

The Costal Corner - Martha's Vineyard
Katama
10.0 out of 10, Exceptional, (10 reviews)
"This property was great for our golf trip. The 3 bedrooms were exceptional "
United States
stephen t.
The price is AED 4,958
AED 6,962 total
includes taxes & fees
20 Aug - 21 Aug
The Costal Corner - Martha's Vineyard
Smart TV, DVD player

16. The Seashell Cove - Martha's Vineyard

The Seashell Cove - Martha's Vineyard
Katama
9.8 out of 10, Exceptional, (29 reviews)
"Nice and clean house, good location on the island, nice neighborhood "
United States
Eric C.
The price is AED 2,755
AED 4,451 total
includes taxes & fees
6 Sep - 7 Sep
The Seashell Cove - Martha's Vineyard
Marina

17. Walk to downtown Edgartown in quiet neighborhood - Perfect Location!

Walk to downtown Edgartown in quiet neighborhood - Perfect Location!
Edgartown
10.0 out of 10, Exceptional, (5 reviews)
"One of the most well equipped vacation rentals I’ve stayed in. A simple, but well curated place. Thank you to our hosts!"
United States
Anonymous traveler
The price is AED 2,755
AED 4,607 total
includes taxes & fees
31 Aug - 1 Sep
Walk to downtown Edgartown in quiet neighborhood - Perfect Location!
Property grounds

18. 1 Mi to Ferry Terminal: Oak Bluffs Family Retreat!

1 Mi to Ferry Terminal: Oak Bluffs Family Retreat!
Oak Bluffs
6.8 out of 10, (9 reviews)
"We had a perfect pre-/off-season stay with plenty of sleeping space. The location is fantastic—right between Vineyard Haven and Edgartown—making it easy to bike to both, plus there’s a beach across the street. The WiFi wasn’t working when we first arrived, but the owner was incredibly responsive and went above and beyond to fix it quickly. We’ll definitely be back!"
United States
Bethann N.
The price is AED 1,161
AED 2,626 total
includes taxes & fees
25 Aug - 26 Aug
1 Mi to Ferry Terminal: Oak Bluffs Family Retreat!
Property grounds

19. Make Lasting Memories In This Adorable Vineyard Cottage!

Make Lasting Memories In This Adorable Vineyard Cottage!
Oak Bluffs
9.8 out of 10, Exceptional, (155 reviews)
"Cute, compact, and had everything we needed for ourstay. I'd definitely stay there again."
United States
Karen C.
The price is AED 918
AED 1,875 total
includes taxes & fees
2 Sep - 3 Sep
Make Lasting Memories In This Adorable Vineyard Cottage!
Dining

20. Walk to Town/Golf Club - Renovated Edgartown Home

Walk to Town/Golf Club - Renovated Edgartown Home
Edgartown
10.0 out of 10, Exceptional, (47 reviews)
"Great house in a great location—just a short, easy walk to downtown Edgartown"
United States
Steven M.
The price is AED 2,149
AED 4,058 total
includes taxes & fees
2 Sep - 3 Sep
Walk to Town/Golf Club - Renovated Edgartown Home
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

Cozy efficiency apartment/heated pool

Cozy efficiency apartment/heated pool

10/10 Excellent
"Cutest space, perfect for one person or two people who really like each other. I do wish I could have had my dog with me as it a very secluded space and I would recommend purchasing a new mattress. Other than that, I would love to book again."
Brenda W. 2-night trip
Posted 7 hours ago
Cozy efficiency apartment/heated pool

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?

Coastal chic meets French Provençal in this newly renovated oceanfront home. : This vacation home near Chilmark is located on the beach and has a fireplace, a balcony, and a barbecue grill to put you at ease 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 can relax into your vacation with a garden and a selection of games.

How many vacation rentals are there in Chilmark?

Choose from 65 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 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 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.