House vacation rentals in Chilmark
Find and book unique houses on Airbnb
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
Home in Barnstable
4.93 out of 5 average rating, 105 reviewsMagical pool home with windmill/new kitchen
Nov 26 – Dec 3
Home in Sagamore Beach
4.91 out of 5 average rating, 146 reviewsSpacious Upper Cape Retreat with Private Pool
Nov 11 – 18
Home in Falmouth
5.0 out of 5 average rating, 26 reviewsCheerful residential home with swimming pool
Jun 10 – 17
Home in Edgartown
4.79 out of 5 average rating, 99 reviewsKatama gem.
Jan 23 – 30
Home in Cotuit
4.91 out of 5 average rating, 11 reviewsShoestringBayHouse, waterfront & pool in Cotuit
Dec 4 – 11
Home in Edgartown
4.9 out of 5 average rating, 41 reviewsBeautiful Edgartown Colonial with heated pool.
Dec 3 – 10
Home in Somerset
5.0 out of 5 average rating, 65 reviewsBeachfront NEW Pool&HotTub/ Sauna & Panoramic view
Apr 2 – 9
Home in Sandwich
4.99 out of 5 average rating, 69 reviews"Cape Escape" luxury home w/pool & beach access.
Mar 25 – Apr 1
Weekly house rentals
Home in Plymouth
4.92 out of 5 average rating, 112 reviewsRomantic Get-Away or Fun filled Family Vacation
Mar 25 – Apr 1
Home in Edgartown
4.92 out of 5 average rating, 140 reviews✅Beach ✅Downtown ✅Restaurants/Bars ✅Bike Path
Oct 5 – 12
Home in Fairhaven
4.95 out of 5 average rating, 146 reviewsDrop Anchor Waterfront
May 19 – 24
Home in Oak Bluffs
4.82 out of 5 average rating, 179 reviewsWaterview, Private, Walk to Beach, Mile to Town
Sep 29 – Oct 6
Home in Falmouth
5.0 out of 5 average rating, 135 reviewsPrivate Pond-side Cape Cod Home
Jan 12 – 19
Home in Edgartown
5.0 out of 5 average rating, 116 reviewsClose to Edgartown Village Center!
Jul 21 – 28
Home in Mashpee
4.96 out of 5 average rating, 166 reviewsGorgeous sunsets! Private family beach - Cape Cod!
Feb 10 – 17
Home in Barnstable
4.94 out of 5 average rating, 171 reviewsMemory Making Getaway on Cape Cod
Jan 31 – Feb 7
Private house rentals
Home in Chilmark
4.88 out of 5 average rating, 40 reviewsCozy Waterfront Cottage, Newly Remodeled!
Aug 25 – Sep 1
Home in Aquinnah
4.9 out of 5 average rating, 50 reviewsOceanview Beachwalk Cottage
Feb 23 – Mar 2
Home in Westport
5.0 out of 5 average rating, 17 reviewsQuaint cottage near beach
Dec 8 – 15
Home in Chilmark
Quintessential Chilmark Retreat
Dec 2 – 9
Home in West Tisbury
5.0 out of 5 average rating, 9 reviewsSecluded Getaway
Nov 29 – Dec 6
Home in Aquinnah
4.9 out of 5 average rating, 49 reviewsAmazing Views!!Sunsets!!HistoricMV Gem&Lg.RoofDeck
Oct 23 – 30
Home in West Tisbury
4.95 out of 5 average rating, 22 reviewsTucked away Up Island
Sep 13 – 20
Home in Fairhaven
4.87 out of 5 average rating, 38 reviewsCottage by the Sea
Nov 5 – 12
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
€ 112 before taxes and fees
Destinations to explore
- Cape Cod Vacation rentals
- Martha's Vineyard Vacation rentals
- Cambridge Vacation rentals
- Montauk Vacation rentals
- Nantucket Vacation rentals
- Salem Vacation rentals
- Newport Vacation rentals
- Philadelphia Vacation rentals
- New York Vacation rentals
- Jersey City Vacation rentals
- The Hamptons Vacation rentals
- Boston Vacation rentals
- Earth house rentals United States
- Lighthouse rentals United States
- House rentals United States
- Townhouse rentals United States
- Guesthouse rentals United States
- Beach house rentals Boston
- Guesthouse rentals Boston
- Townhouse rentals Boston
- House rentals Boston
- House rentals The Hamptons
- Guesthouse rentals The Hamptons
- Beach house rentals The Hamptons
- Lakehouse rentals Cape Cod
- Guesthouse rentals Cape Cod
- Beach house rentals Cape Cod
- Tiny house rentals Cape Cod
- Townhouse rentals Cape Cod
- House rentals Cape Cod
- Guesthouse rentals Massachusetts
- Beach house rentals Massachusetts
- Lakehouse rentals Massachusetts
- House rentals Massachusetts
- Tiny house rentals Massachusetts
- Townhouse rentals Massachusetts
- Fitness-friendly rentals Chilmark
- Rentals with a fireplace Chilmark
- Rentals with a washer and dryer Chilmark
- Rentals with outdoor seating Chilmark
- Rentals with a fire pit Chilmark
- Rentals with a patio Chilmark
- Rentals with beach access Chilmark
- Monthly Rentals Chilmark
- Pet-friendly rentals Chilmark
- Kid-friendly rentals Chilmark
- Family-friendly rentals Chilmark
- House rentals Dukes County
- Guesthouse rentals Dukes County
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom