Holiday rentals in Chilmark

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Top-rated holiday rentals in Chilmark

Guests agree: these stays are highly rated for location, cleanliness, and more.

Guest favourite
Guest suite in Oak Bluffs
Lovely 2 BR Oak Bluffs Apartment
This 100% private apartment is on the first floor of a shared house where owners and their son live upstairs. There are no shared spaces. You have a private entrance and parking. The living room, bedrooms, bathroom, and kitchenette are bright and clean. It is exactly 1 mile from Oak Bluffs Center, a half mile from The Cottages and Farm Neck Golf Course, and a block from Tradewinds walking trails. Across the street is the bike path, & the bus stop is on the corner for easy island transportation!
19–26 Jan
$118 SGD per night
4.94 out of 5 average rating, 300 reviews
Guest favourite
Home in West Tisbury
Secluded Up Island Cottage
Charming Martha's Vineyard post and beam house on two secluded acres with two bedrooms in West Tisbury. The master bedroom has a queen bed, the second bedroom has a full bed, the loft has a full size futon. It is peacefully tucked away at the end of a road with only three other houses on it. It has easy access to beaches, bike paths and walking trails. Enjoy some family time in the wooded backyard grilling or relaxing with an outdoor shower or napping in the hammock after a day at the beach.
3–10 Feb
$294 SGD per night
4.97 out of 5 average rating, 119 reviews
Guest favourite
Guest house in Falmouth
Wooded studio apartment in Woods Hole village
A one-room studio apartment behind our main house is the perfect place for someone visiting Woods Hole village. It works for one guest or a couple. Please note the apartment is located directly behind the main house. COVID-19 UPDATE: Our cleaning crew is now following the enhanced cleaning checklist recently suggested by AirBnb to further clean and disinfect between stays. Given that many bookings were made prior to the outbreak, a 24-hour break has not always been possible between visits.
8–15 Jan
$137 SGD per night
4.9 out of 5 average rating, 232 reviews

Popular amenities for Chilmark holiday rentals

Stay near Chilmark's top sights

Aquinnah Cliffs Overlook51 locals recommend
Larsen's Fish Market48 locals recommend
Menemsha Fish Market12 locals recommend
Martha's Vineyard Agricultural Society9 locals recommend
State Road60 locals recommend
Chilmark General Store33 locals recommend

Other great holiday rentals in Chilmark

Guest favourite
Cottage in Aquinnah
Blaine's Cottage
23–30 Nov
$325 SGD per night
4.97 out of 5 average rating, 30 reviews
Guest favourite
Cottage in Chilmark
Vintage Chilmark Retreat
28 Aug – 4 Sep
$515 SGD per night
4.96 out of 5 average rating, 28 reviews
Guest favourite
Home in Chilmark
The Blueberry House on Martha’s Vineyard
18–25 May
$655 SGD per night
5.0 out of 5 average rating, 10 reviews
Guest favourite
Home in Chilmark
Renovated Barn in Chilmark 3BR-help w/boat tickets
8–15 Nov
$502 SGD per night
4.99 out of 5 average rating, 87 reviews
Guest favourite
Home in Chilmark
Cozy Waterfront Cottage, Newly Remodeled!
14–21 Jul
$1,003 SGD per night
4.88 out of 5 average rating, 40 reviews
Guest favourite
Home in Chilmark
2 BR-Private guest house with Hot Tub and Fire Pit
11–18 Dec
$373 SGD per night
5.0 out of 5 average rating, 52 reviews
Superhost
Villa in Chilmark
3 Bedroom house w Guest Cottage off of Middle Road
12–19 Oct
$1,233 SGD per night
5.0 out of 5 average rating, 11 reviews
Superhost
Home in Chilmark
Quintessential Chilmark Retreat
13–20 Oct
$1,032 SGD per night
New place to stay
Guest favourite
Cottage in West Tisbury
Cozy Cottage
9–16 Jul
$301 SGD per night
4.95 out of 5 average rating, 63 reviews
Guest favourite
Home in Chilmark
Come relax on our Water View Farm with Ocean Views
24 Apr – 1 May
$667 SGD per night
4.84 out of 5 average rating, 19 reviews
Guest favourite
Guest house in West Tisbury
Vineyard Meadow Artist Studio
22–29 Sep
$335 SGD per night
5.0 out of 5 average rating, 18 reviews
Guest favourite
Home in West Tisbury
Secluded Getaway
16–23 Nov
$667 SGD per night
5.0 out of 5 average rating, 9 reviews

Quick stats about holiday rentals in Chilmark

Total rentals

180 properties

Rentals with a pool

10 properties have a pool

Pet-friendly rentals

60 properties allow pets

Family-friendly rentals

150 properties are a good fit for families

Total number of reviews

3.5K reviews

Nightly prices starting at

$94 SGD before taxes and fees

Destinations to explore

  1. Airbnb
  2. United States
  3. Massachusetts
  4. Dukes County
  5. Chilmark