
Vacation rentals in Chilmark
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Top-rated vacation rentals in Chilmark
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Popular amenities for Chilmark vacation rentals
Other great vacation rentals in Chilmark

Beach Glass Cottage - Pond Front
My friends and I stay at Maureen’s cottage every February for a winter stitching getaway. The house is perfect for the 3 of us. It has 3 comfortable bedrooms and 2 full baths. The living room is spacious. We love the kitchen and dining table. We set up our stitching gear and stitch the days away until it’s time to say goodbye. There are so many great restaurant choices close by. We highly recommend the Keltic Kitchen a short distance away on rte 28. Perfect breakfast place. We also tried for the first time a very small Thai restaurant, Bangkok Kitchen. The food was delicious and very nice people. Back to Maureen’s Beach Glass Cottage…just a perfect place to stay. The amenity list does not even begin to cover what they have available. It’s the perfect getaway home in my opinion. The one floor living is great for us with 1 of us having mobility issues. We cannot wait to come back. Thank You!

5 Blocks to Beach+Town, Stocked Kitchen, Cozy Beds
Lovely house and peaceful and quiet neighborhood.

Ideal Vacation Home On Dennis Highlands
This place was everything we could’ve wanted for a week at the Cape. It’s in one of the best areas we have ever stayed on Cape Cod. We loved how they have the house decorated it was perfect. We had PLENTY of room for my wife, our two kids and me to relax when we were spent from activities. The yard was huge and there was wildlife all around. Nice and private location but 5-10 minute drive to get to anything you want. They were super accommodating to our last minute schedule shift and very responsive and give spot on recommendations on some things to check out. We would hands down stay again.

25 Menemsha Rd., Popponesset, pond & beach views
We absolutely enjoyed our stayed. It's beautiful from the pictures online, but when you walk in it has a feel of being at a getaway even better than expected. The view is gorgeous and the home is very well kept and decorated. A big bonus for us was the spacious outdoor hottub. I would definitely feel comfortable booking with them again!

Escape to the Cape
Ananta was very communicative and proactively helpful. Her residence was very accommodating for a family of 6 plus a cat. We all really enjoyed our stay. P.S. Thank you for the welcome snacks and the plant!

Private home, secluded 6 acre lot with water view
Rebecca’s house in Wareham was a blessing! She is an attentive and responsive host, any concerns I had she was able to resolve immediately. We found ourselves wishing we had booked a longer stay to enjoy everything there was to offer!! Thank you Rebecca!

Spacious home with beach access and amenities
Abdel’s place was perfect for our family weekend getaway. Home was spacious and very clean. Had everything we needed (even toys for my toddler and our dog!). My whole family was very comfortable. Neighborhood was walkable and beach was easily accessible. Sunsets were spectacular! Would stay again!

5 Bedroom, Central Air, Close to Beaches and MORE!
It is a nice house for a large family. We had between 8-12 there at any points. Close to beaches.
Quick stats about vacation rentals in Chilmark
Total rentals
200 properties
Nightly prices starting at
$90 before taxes and fees
Total number of reviews
4K reviews
Family-friendly rentals
170 properties are a good fit for families
Pet-friendly rentals
80 properties allow pets
Rentals with a pool
10 properties have a pool
Frequently Asked Questions
Are there vacation rentals with a dedicated workspace in Chilmark?
Yes! Work meets play with ease at over 100 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 80 vacation rentals for guests traveling with pets.
How much does it cost to stay in guesthouse rentals in Chilmark?
Experience the best of Chilmark with our guesthouse rentals, starting at about $190 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
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!
Do house rentals in Chilmark have self check-in?
Absolutely! We offer over 30 house rentals with self check-in 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.
Are there family-friendly house rentals in Chilmark?
Chilmark has more than 150 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
What are the most popular amenities for House Rentals in Chilmark?
Enhance your stay in our House Rentals with the most popular amenities: over 80 homes with a bbq area, over 30 homes with self check-in, over 160 homes with wifi, over 10 homes with a gym, and more. Indulge in the ultimate retreat, tailored to your preferences.
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- Brown University
- Sandwich Glass Museum
- Owen Park Beach
- Sagamore Beach
- New Silver Beach
- Onset Beach
- Lighthouse Beach
- Blue Shutters Beach
- Roger Williams Park Zoo
- Nickerson State Park
- Oakland Beach
- Grey's Beach
- Chapin Memorial Beach
- Scusset Beach
- Pinehills Golf Club
- South Shore Beach
- Earle Road Beach
- Baker's Beach Club
- Fort Adams State Park
- Salty Brine State Beach
- Agawam Hunt
- Rocky Point Beach
- Oyster Harbors Beach
- Englewood Beach
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