
House vacation rentals in Chilmark
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Top-rated house rentals in Chilmark
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Vacation rentals for every style
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Popular amenities for Chilmark house rentals
House rentals with a pool

Stunning Cape Home - Inground Pool, 5 Min To Beach
This house and property were charming and beautiful. The location was extremely close to beaches, restaurants, and stores all while being nestled in a quiet neighborhood. Highly recommend!

House on Cape Cod with pool close to beach
Alena's place had everything we needed for a lovely week on the Cape. Great pool and location between Mayflower and Dennis Village. My daughter loved the home's bright airy playroom and it kept us sane and entertained on a couple of rainy days. Would definitely visit again!

New Cape Escape for 10 People With Heated Pool
Perfect stay. Pool was amazing. Host was very responsive to everything. Great for families, Just bring socks with friction pads on the bottom so you don’t slide .

Spectacular beach & pool combo; beautiful sunsets!
The house was beautiful, very comfortable and extremely well equipped. I would highly recommend this home. We had a wonderful stay there!

Waterfront Oasis Pool EPIC Views
super fun! great for larger groups- plenty of space for everyone and a well-stocked house

Spacious home with Pool! Close to Beaches & Town!
it is a nice comfy house esp for a family. Swimming pool and game room down in the basement would be alot of fun for kids to keep them busy at day time and night time. Beach, restaurants, grocery stores, liquor stores, etc are all right there esp. only like less than 5 to 15 minutes drive and also less than 25 minutes drive to go to north Falmouth or Wood Hole. They have a nice downtown with many stores, restaurants, bowling ally, etc which that is only less than 15 minutes drive from the house Also taking a walk from the house to the beach is so beautiful esp morning time. i walked every morning, and love every bit of the walk. It rained once during our vacation week and rest were sunny days for the rest of the week. We were lucky to have the good weather. Anyway, the house is approximately about less than a mile and half from the beach. Driving to Chetham is about little a hour drive from the house. To Provincetown, about 1 hour and 45 minutes drive.

New Construction Home with Pool in N. Falmouth
This house was stunning! So beautiful and more than enough space for our group of 10. I’d definitely recommend staying here if you’re going to Cape Cod. It was a quick drive for us to bars/ restaurants/ stores, and a great house to stay in and entertain.

Winslow Acres [heated] Pool Escape; pool May 15
The house was clean and comfortable. I loved the coffee bar:) my kids loved the pool and hot tub. And it was especially great to be able to bring my dog! We will definitely rent again.
Weekly house rentals

#25 Seasonal Cottage is 200 feet from the Beach
A minor communication glitch between host and cleaners meant two of the beds had not been made and probably a general cleaning between guests wasn't done. Fortunately the property was already very clean and the guests before me must have been, too. Everything else was in order. When I let the host know, she immediately contacted the cleaners while I went out for groceries. By the time I got back, the place was perfect and the cleaners were gone. I don't think this is a regular occurrence at all. In October this neighborhood was very quiet, which is a priority for me. And I felt very safe, which is also important. I would definitely return and highly recommend.

Cape Cod Life is Good Rentals
I highly recommend this amazing house! Located in a quiet neighborhood, but close to all of the amenities on Rte 28, this cozy house offers ample sitting area and sleeping accommodations. Choo and Bao Chau are amazing hosts and incredibly responsive. This lovely, well-maintained home is perfect for a family or small group of friends!

Beach Home – Family Friendly - Solar Powered
This house was a perfect place for our annual family gathering. There were 9 people from 16 to 83. The open space, first floor bedroom and bunk room were perfect for our group! Ciara was a great host!!

Expansive & Renovated Teaticket Cape
Great house for a larger group. It has all the amenities and lots of beds. Very close to the ocean and Brien was easy to communicate with. Thank you for having us at your home!

Waterview, Private, Walk to Beach, Mile to Town
We stayed at Lisa’s place for three nights and it was a 10/10 experience. Lisa was a fantastic host and was very helpful with island recommendations prior to our trip. The property itself is stunning and although we wanted to explore the island, the property also provided a beautiful landscape to just relax. Even given its private, peaceful location, it was still so convenient to town. The house is an adorable converted barn that has incredible, rustic charm and the decor was so beautifully thought out. Before we even left we were talking about booking again in the future. We definitely recommend booking here!

Waterfront★ Hot Tub ★ Kayaks ★ Firepit ★ Pet OK
We had a great time. House was extremely clean and Aruna was fantastic with communication. Would recommend to anyone to hook this spot.

Westport Point cottage, 5 minute bike to CW beach
Our stay was so cozy and perfect for what we were looking for! It had everything we needed to cook a nice dinner, and we enjoyed our morning coffee on the front porch. A little pricey for the winter since it’s really quiet at this time of year, but very peaceful and relaxing so it was worth it. Highly recommend!

Downtown Osterville Updated 4 Bedroom
I reserved Molly's house as a place for my family of 7 adults to stay together for a wedding weekend in the area. We found the house to be exactly as described in the listing and by other reviewers: beautiful, clean, spacious, well-appointed lovely home within minutes of beaches and the country clubs where the wedding events were held. Molly was a very gracious host. I messaged her on Thursday evening to mention that we were in need of clothes hangers and a blow dryer, and she placed an order for both which was delivered by 10AM the next morning. Our experience there could not have been better!
Private house rentals

Private home with walkable freshwater beach access
The house was as advertised. In a nice quiet area. The house was well set up and as advertised. We felt right at home for the weekend.

The Mills Retreat- 3BR/2Bath - Beach pass included
We had a great time!!! Perfect for a nice relaxing girls weekend.

Spacious Mid-Cape Home 5 Bedrooms, 9 Beds, 3 Bath
We absolutely loved our stay at Rachel’s! We kept saying “this place has everything”. It was a wonderful home for a multi generation holiday hang. From a 7 month old to great grand parents. The main floor was easily accessible for family member with a disability. We felt right at home with our 7 month old, the home had a pack n play - all set up with fresh sheets, baby bath tub, high chair, bath toys, monitor, etc. The basement was perfect for the teenagers to hangout and have their space. The backyard was peaceful and extended the hang area. Rachel was incredibly friendly and responsive.

New Seabury home, private yard, great location
Comfortable yet spacious home nestled in the woods of New Seabury. Great location to visit beaches and restaurants. Just minutes from Mashpee Commons and Falmouth for shopping and dining. Beautiful place, Thanks Alex!

Spacious and immaculate custom home.
We had a fantastic family vacation in Falmouth and Anne’s house greatly exceeded all of our expectations! Comfortable, beautiful decorated and appointed with every amenity. We will be back!

Holiday in the sun!
Craig was awesome and extremely nice and understanding! The house was clean and one of the best I have stayed in. The location is quiet and tucked in a small neighborhood. I had the most amazing stay and would suggest this to anyone going to this location!

Cape Cod Lakefront Home
Nice private house with lots of bedrooms, a pool and nice grounds. House was very clean. We had a great time with our family. Can walk to a few places in town, but need to get into the car for most. The Dennis beaches were great and just a short drive away. Would recommend this place for families. The house has access to Scargo Lake, which is nice, but it is a bit of a hike down a good-sized hill. Host was nice and responsive to questions.

Your home away from home
Patricia was very responsive before and during our stay. She was easy to communicate with and gave great suggestions for beaches to visit. The house is about a 10 minute drive from the closest beach. It’s near water but it’s more for fishing or boating. It’s less than 10 minutes from the center of town where there are great places to eat and shop around. The house is beautiful and spacious. Two bedrooms and a full bathroom on the main level and 2 bedrooms and a full bathroom the second level. Highly recommend.
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
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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
- Onset Beach
- Lighthouse Beach
- Blue Shutters Beach
- Roger Williams Park Zoo
- Oakland Beach
- Pinehills Golf Club
- Nickerson State Park
- South Shore Beach
- Grey's Beach
- Chapin Memorial Beach
- Scusset Beach