Chilmark vacation rentals
Book unique vacation rentals, houses, and more on Airbnb
Top-rated vacation rentals in Chilmark
Guests agree: these vacation rentals 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 vacation rentals
Other great vacation rentals in Chilmark
Apartment in Falmouth
4.95 out of 5 average rating, 239 reviewsUpscale suite w/ separate entrance.
Jan 4 – 11
Apartment in Falmouth
4.96 out of 5 average rating, 151 reviewsYour Private Garden
Oct 19 – 26
Apartment in New Bedford
4.9 out of 5 average rating, 218 reviewsModern Downtown Apartment
May 4 – 11
Loft in Westport
4.88 out of 5 average rating, 239 reviewsBrithaven Farm
Oct 17 – 24
Guest suite in Bourne
4.78 out of 5 average rating, 139 reviewsRustic Beach Cottage
Dec 20 – 27
Farm stay in Chilmark
4.96 out of 5 average rating, 23 reviewsThe Cottage at Rockrose Farm
Dec 21 – 28
Home in Chilmark
4.88 out of 5 average rating, 40 reviewsCozy Waterfront Cottage, Newly Remodeled!
Jan 5 – 12
Guesthouse in Chilmark
4.99 out of 5 average rating, 77 reviews4-Season Guest House on Historic Chilmark Estate
Nov 25 – Dec 2
Other great vacation rentals in Chilmark
Home in Chilmark
5.0 out of 5 average rating, 54 reviews2 BR-Private guest house with Hot Tub and Fire Pit
Oct 14 – 21
Cottage in Aquinnah
4.97 out of 5 average rating, 30 reviewsBlaine's Cottage
Aug 24 – 31
Home in Chilmark
4.99 out of 5 average rating, 87 reviewsRenovated Barn in Chilmark 3BR-help w/boat tickets
Dec 9 – 16
Home in Chilmark
5.0 out of 5 average rating, 10 reviewsThe Blueberry House on Martha’s Vineyard
Mar 5 – 12
Villa in Chilmark
5.0 out of 5 average rating, 11 reviews3 Bedroom house w Guest Cottage off of Middle Road
Jan 19 – 26
Home in Chilmark
Quintessential Chilmark Retreat
Nov 13 – 20
Cottage in West Tisbury
4.95 out of 5 average rating, 63 reviewsCozy Cottage
May 5 – 12
Cottage in Chilmark
5.0 out of 5 average rating, 7 reviewsMenemsha Cottage
May 18 – 25
Quick stats about vacation rentals in Chilmark
Total rentals
200 properties
Rentals with a pool
10 properties have a pool
Pet-friendly rentals
70 properties allow pets
Family-friendly rentals
160 properties are a good fit for families
Total number of reviews
3.5K reviews
Nightly prices starting at
G$20,889 GYD before taxes and fees
Frequently Asked Questions
Are there vacation rentals with a dedicated workspace in Chilmark?
Yes! Work meets play with ease at over 110 vacation rentals in Chilmark featuring dedicated workspaces. Stay connected and productive in your home away from home.
Are there pet-friendly vacation rentals in Chilmark?
Four-legged friends are welcome in Chilmark. Choose from more than 70 vacation rentals for guests traveling with pets.
Do house rentals in Chilmark have air conditioning?
Absolutely! We offer over 110 house rentals with air conditioning in Chilmark. Enjoy a tailored experience with all the comforts you desire.
Do cottage rentals in Chilmark have wifi?
Absolutely! We offer over 10 cottage rentals with wifi in Chilmark. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Chilmark have a gym?
Absolutely! We offer over 10 house rentals with a gym in Chilmark. Enjoy a tailored experience with all the comforts you desire.
Do cabin rentals in Chilmark have a bbq area?
Absolutely! We offer over 10 cabin rentals with a bbq area in Chilmark. Enjoy a tailored experience with all the comforts you desire.
How much does it cost to stay in guesthouse rentals in Chilmark?
Experience the best of Chilmark with our guesthouse rentals, starting at about $150 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Are there family-friendly house rentals in Chilmark?
Chilmark has more than 130 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
Are there Chilmark vacation rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 10 vacation homes with pools in Chilmark, available on Airbnb. Make a splash and soak up the sun in style!
What are the most popular amenities for House Rentals in Chilmark?
Enhance your stay in our House Rentals with the most popular amenities: over 140 homes with wifi, over 90 homes with a bbq area, over 110 homes with air conditioning, over 10 homes with a gym, and more. Indulge in the ultimate retreat, tailored to your preferences.
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