
House vacation 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.
Vacation 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

Stunning Cape Home - Inground Pool, 5 Min To Beach

Secluded Oasis w/ Heated Pool - 10 mins to Newport

House on Cape Cod with pool close to beach

HUGE family house. Sleeps 10+ Pool, Beach, AC

Modern Home w/ Pool & Game Room | Mins to Newport

New Cape Escape for 10 People With Heated Pool

Waterfront Oasis Pool EPIC Views

Spacious home with Pool! Close to Beaches & Town!
Weekly house rentals

#25 Seasonal Cottage is 200 feet from the Beach

* Walk to the beach - Swiss Beach House! *

Cape Cod Life is Good Rentals

The Newport Cottage.Perfect Location/Comfort/Style

Adorable Cottage - Premier Location in West Dennis

Beach Home – Family Friendly - Solar Powered

Waterfront★ Hot Tub ★ Kayaks ★ Firepit ★ Pet OK

Totally Unique House for rent
Private house rentals

The Mills Retreat- 3BR/2Bath - Beach pass included

Waterview, Private, Walk to Beach, Mile to Town

Well-Appointed 3 Bedrm 4 Bathrm w/ 50+ 5* Reviews

Holiday in the sun!

Your home away from home

New Home 1 Bedroom and Bath Sleeps 4

NEW! 2 Houses, Main House plus Guest House

Edgartown Beauty: The Perfect Retreat, Dogs OK
Quick stats about house rentals in Chilmark
Total rentals
160 properties
Nightly prices starting at
ﺩ.ﺇ441 before taxes and fees
Total number of reviews
2.2K reviews
Family-friendly rentals
150 properties are a good fit for families
Pet-friendly rentals
60 properties allow pets
Rentals with dedicated workspaces
80 properties have a dedicated workspace
Destinations to explore
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- Rentals with outdoor seating Chilmark
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- Rentals with a fire pit Chilmark
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- Cape Cod
- Mayflower Beach
- Charlestown Beach
- West Dennis Beach
- East Sandwich Beach
- Craigville Beach
- Duxbury Beach
- Brown University
- Easton Beach
- Sandwich Glass Museum
- Owen Park Beach
- Sagamore Beach
- New Silver Beach
- Roger Williams Park Zoo
- Blue Shutters Beach
- Onset Beach
- Lighthouse Beach
- South Shore Beach
- Oakland Beach
- Fort Adams State Park
- Scusset Beach
- Pinehills Golf Club
- Nickerson State Park
- Oyster Harbors Beach