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 house rentals in Chilmark
House rentals with a pool
Home in Sagamore Beach
4.91 out of 5 average rating, 146 reviewsSpacious Upper Cape Retreat with Private Pool
2–9 Apr
Home in Falmouth
5.0 out of 5 average rating, 26 reviewsCheerful residential home with swimming pool
10–17 Jun
Home in Edgartown
4.79 out of 5 average rating, 99 reviewsKatama gem.
19–26 Jan
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.
10–17 Nov
Home in Falmouth
4.94 out of 5 average rating, 17 reviewsDog Friendly Cape Oasis | Pool+Beach |Tennis Court
30 Dec – 6 Jan
Home in Sandwich
4.99 out of 5 average rating, 69 reviews"Cape Escape" luxury home w/pool & beach access.
8–15 Jan
Home in Wareham
4.93 out of 5 average rating, 59 reviewsEdgewater Coastal Retreat with Heated Pool
10–17 Nov
Weekly house rentals
Home in Edgartown
4.92 out of 5 average rating, 140 reviews✅Beach ✅Downtown ✅Restaurants/Bars ✅Bike Path
5–12 Oct
Home in Sandwich
5.0 out of 5 average rating, 112 reviews*Oceanfront Beach Home*
17–24 Oct
Home in West Tisbury
4.86 out of 5 average rating, 107 reviewsSweet 3BR Cape in West Tisbury, MV
14–21 Mar
Home in Mashpee
4.96 out of 5 average rating, 166 reviewsGorgeous sunsets! Private family beach - Cape Cod!
6–13 Jan
Home in Fairhaven
4.95 out of 5 average rating, 146 reviewsDrop Anchor Waterfront
19–24 May
Home in Oak Bluffs
4.82 out of 5 average rating, 179 reviewsWaterview, Private, Walk to Beach, Mile to Town
23–30 May
Home in Falmouth
5.0 out of 5 average rating, 135 reviewsPrivate Pond-side Cape Cod Home
5–12 Jan
Home in New Bedford
4.99 out of 5 average rating, 183 reviewsHistoric Cobblestone Carriage House near Downtown
16–23 Jun
Private house rentals
Home in Chilmark
4.99 out of 5 average rating, 87 reviewsRenovated Barn in Chilmark 3BR-help w/boat tickets
20–27 May
Home in Chilmark
5.0 out of 5 average rating, 55 reviews2 BR-Private guest house with Hot Tub and Fire Pit
14–21 Jul
Home in Aquinnah
4.9 out of 5 average rating, 50 reviewsOceanview Beachwalk Cottage
14–21 Nov
Home in Chilmark
Quintessential Chilmark Retreat
27 Nov – 4 Dec
Home in Westport
5.0 out of 5 average rating, 17 reviewsQuaint cottage near beach
19–26 Jan
Home in West Tisbury
5.0 out of 5 average rating, 9 reviewsSecluded Getaway
14–21 Dec
Home in Edgartown
5.0 out of 5 average rating, 10 reviewsDiamond in the Rough
10–17 May
Home in West Tisbury
4.95 out of 5 average rating, 22 reviewsTucked away Up Island
13–20 Sep
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
$162 SGD before taxes and fees
Destinations to explore
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