House holiday rentals in Chilmark
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Top-rated house rentals in Chilmark
Guests agree: These houses are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Chilmark house rentals
House rentals with a pool
Home in Sagamore Beach
4.91 out of 5 average rating, 146 reviewsSpacious Upper Cape Retreat with Private Pool
16–23 Mar
Home in Falmouth
5.0 out of 5 average rating, 26 reviewsCheerful residential home with swimming pool
10–17 Jun
Home in Cotuit
4.91 out of 5 average rating, 11 reviewsShoestringBayHouse, waterfront & pool in Cotuit
4–11 Dec
Home in Edgartown
4.9 out of 5 average rating, 41 reviewsBeautiful Edgartown Colonial with heated pool.
2–9 Dec
Home in Edgartown
4.79 out of 5 average rating, 99 reviewsKatama gem.
22–29 Jan
Home in Jamestown
4.89 out of 5 average rating, 9 reviewsNamaste
16–23 Apr
Home in Somerset
5.0 out of 5 average rating, 65 reviewsBeachfront NEW Pool&HotTub/ Sauna & Panoramic view
26 Dec – 2 Jan
Home in Sandwich
4.99 out of 5 average rating, 69 reviews"Cape Escape" luxury home w/pool & beach access.
3–10 Nov
Weekly house rentals
Home in Dartmouth
4.92 out of 5 average rating, 128 reviewsSerene 3-Bedroom Lakeside Home
23–30 Nov
Home in Sandwich
4.99 out of 5 average rating, 113 reviews*Oceanfront Beach Home*
9–16 Dec
Home in Edgartown
4.92 out of 5 average rating, 140 reviews✅Beach ✅Downtown ✅Restaurants/Bars ✅Bike Path
5–12 Oct
Home in Fairhaven
4.95 out of 5 average rating, 146 reviewsDrop Anchor Waterfront
19–24 May
Home in Falmouth
5.0 out of 5 average rating, 135 reviewsPrivate Pond-side Cape Cod Home
7–14 Jan
Home in Barnstable
4.94 out of 5 average rating, 171 reviewsMemory Making Getaway on Cape Cod
26 Apr – 3 May
Home in Falmouth
4.96 out of 5 average rating, 253 reviewsNewly renovated garden carriage house
7–14 Oct
Home in Chilmark
5.0 out of 5 average rating, 10 reviewsThe Blueberry House on Martha’s Vineyard
22–29 Apr
Private house rentals
Home in Aquinnah
4.9 out of 5 average rating, 50 reviewsOceanview Beachwalk Cottage
19–26 Nov
Home in Westport
5.0 out of 5 average rating, 17 reviewsQuaint cottage near beach
21–28 Nov
Home in Chilmark
Quintessential Chilmark Retreat
30 Nov – 7 Dec
Home in West Tisbury
5.0 out of 5 average rating, 9 reviewsSecluded Getaway
6–13 Jan
Home in West Tisbury
4.95 out of 5 average rating, 22 reviewsTucked away Up Island
13–20 Sep
Home in Edgartown
5.0 out of 5 average rating, 10 reviewsDiamond in the Rough
11–18 Nov
Home in Fairhaven
4.87 out of 5 average rating, 38 reviewsCottage by the Sea
13–20 Dec
Home in West Tisbury
4.83 out of 5 average rating, 12 reviewsVineyard Meadow Writer's Cottage
30 Sep – 7 Oct
Quick stats about house rentals in Chilmark
Total rentals
140 properties
Rentals with dedicated workspaces
80 properties have a dedicated workspace
Pet-friendly rentals
50 properties allow pets
Family-friendly rentals
130 properties are a good fit for families
Total number of reviews
1.9K reviews
Nightly prices starting at
$200 NZD before taxes and fees
Destinations to explore
- Cape Cod Holiday rentals
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