House vacation rentals in Chilmark

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Popular amenities for Chilmark house rentals

House rentals with a pool

Superhost
Home in Barnstable
4.8 out of 5 average rating, 20 reviews

Stunning Cape Home - Inground Pool, 5 Min To Beach

KristenRating, 5 stars1 week ago
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!
Guest favourite
Home in Popponesset
5 out of 5 average rating, 12 reviews

18 Menemsha Rd., Popponesset, Pool, 3-Beds, 4 bath

CarolRating, 5 stars1 week ago
We loved are family stay at Paul & Katie’s home for Easter Week. It is a dream home . The neighborhood was beautiful and walkable, with a peaceful path to a private beach. We enjoyed the shops and restaurants in Mashpee Commons about an 8 minute drive away.
Superhost
Home in Forestdale
4.64 out of 5 average rating, 11 reviews

New Cape Escape for 10 People With Heated Pool

LaurenRating, 5 stars7 months ago
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 .
Top guest favourite
Home in Oak Bluffs
4.94 out of 5 average rating, 194 reviews

Spectacular beach & pool combo; beautiful sunsets!

JillRating, 5 stars3 weeks ago
The house was beautiful, very comfortable and extremely well equipped. I would highly recommend this home. We had a wonderful stay there!
Superhost
Home in East Falmouth
5 out of 5 average rating, 3 reviews

Spacious home with Pool! Close to Beaches & Town!

michaelRating, 5 stars8 months ago
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.
Guest favourite
Home in North Falmouth
5 out of 5 average rating, 13 reviews

New Construction Home with Pool in N. Falmouth

MichelleRating, 5 stars7 months ago
Had a great family vacation for my sisters wedding. House was perfect for our toddlers with kids room in basement. Stunning home and amenities, the perfect Cape Cod vacation home!
Top guest favourite
Home in Cotuit
4.95 out of 5 average rating, 113 reviews

Private Pool, near beaches, 3 BR/3 BA, Central Air

CamilleRating, 5 stars7 months ago
There should be more than 5 stars for this lovely property and its hosts!!! We were three couples vacationing for the first time on the Cape and this charming home was perfect for us. Conveniently located to serve as home base for many excursions we felt immediately at home. We each had our own themed bedroom with en suite bathroom and TV. All common areas including the sun porch and outdoor deck were fantastic places to gather and enjoy our time together. Our hosts were so pleasant and helpful throughout our stay. As only one example, on a rainy day the host proactively contacted us wth suggestions on things to do in the event of rain on the Cape. We so appreciated this thoughtful gesture and there were many more. When I think about it, this really sums up why we had such a wonderful time. Everything about this property speaks to how much these hosts care about their guests! Hope to return one day. Thank you!
Guest favourite
Home in Falmouth
5 out of 5 average rating, 16 reviews

Secluded Cape Cod home in Falmouth with pool

DanielleRating, 5 stars7 months ago
This house was perfect for our large group getaway. Lots of bedrooms and bathrooms and the detached pool house apartment was a nice option for those who wanted to be a bit more separate from the big group. The yard/pool was beautiful and Renaldo was extremely responsive to any questions we had. Would definitely stay here again!

Weekly house rentals

Guest favourite
Home in Centerville
4.88 out of 5 average rating, 111 reviews

#25 Seasonal Cottage is 200 feet from the Beach

RuthRating, 5 stars6 months ago
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.
Top guest favourite
Home in Yarmouth
4.95 out of 5 average rating, 151 reviews

Cape Cod Life is Good Rentals

JaredRating, 5 stars4 weeks ago
This was a great place for a large family. The kids especially enjoyed riding bicycles through the neighborhood. The house was spacious and comfortable. We plan to stay again.
Superhost
Home in Tisbury
4.69 out of 5 average rating, 158 reviews

Carolyn's Vineyard Haven

JenniferRating, 5 stars1 week ago
We had a wonderful stay at this beautiful Martha’s Vineyard home! It was incredibly spacious - perfect for our family of 5 and could easily fit more. Thoughtfully decorated and stocked with everything a real home has, from quality kitchenware to high-end soaps and shampoos (a rare Airbnb treat!). Our kids especially loved the triple bunk bed. Check-in was a breeze, and the location couldn’t be better. We’d absolutely stay here again!
Guest favourite
Home in Westport
4.85 out of 5 average rating, 106 reviews

Beach Home – Family Friendly - Solar Powered

ReneeRating, 5 stars1 month ago
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!!
Guest favourite
Home in Teaticket
4.84 out of 5 average rating, 74 reviews

Expansive & Renovated Teaticket Cape

AnnieRating, 5 stars3 weeks ago
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!
Guest favourite
Home in Oak Bluffs
4.83 out of 5 average rating, 193 reviews

Waterview, Private, Walk to Beach, Mile to Town

LaurenRating, 5 stars6 months ago
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!
Top guest favourite
Home in Centerville, Barnstable
4.97 out of 5 average rating, 153 reviews

Luxury House 0.25 mi from Craigville Beach

SarahRating, 5 stars2 days ago
Came here for my sisters bachelorette. It was amazing . We felt right at home . It was very spacious and clean . Hosts thought of everything . Definitely would come back. The hosts were very responsive and very flexible. Great place to stay. The games and ping pong and air hockey tables were a hit !!
Superhost
Home in Westport
4.66 out of 5 average rating, 47 reviews

Westport Point cottage, 5 minute bike to CW beach

BeccaRating, 5 stars1 month ago
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!

Private house rentals

Top guest favourite
Home in Falmouth
4.92 out of 5 average rating, 78 reviews

Private home with walkable freshwater beach access

MatthewRating, 5 stars7 months ago
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.
Superhost
Home in Marstons Mills
4.88 out of 5 average rating, 133 reviews

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

JulieRating, 5 stars4 months ago
This was a family Christmas getaway, and it was perfect.
Superhost
Home in New Seabury
4.91 out of 5 average rating, 34 reviews

New Seabury home, private yard, great location

MikeRating, 5 stars6 months ago
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!
Superhost
Home in Sandwich
4.77 out of 5 average rating, 26 reviews

Holiday in the sun!

KaylaRating, 5 stars1 week ago
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!
Guest favourite
Home in New Seabury
4.83 out of 5 average rating, 109 reviews

New Seabury Retreat. Butchart Gardens' Inspired

ErinRating, 5 stars7 months ago
Vlad’s home was a wonderful place to stay with many people! Really appreciated all the decor and attention to detail. My friends and I stayed for a wedding, and we were so glad all communication was smooth. Would definitely stay again!
Top guest favourite
Home in Edgartown
5 out of 5 average rating, 18 reviews

Valentine's Retreat Hot Tub Fire Pit Trails Beach

DaniellaRating, 5 stars1 week ago
Genainna’s place was great! It was very big so my group was comfortable with the beds available, there were many amenities and detailes like extra toothbrushes or other things that I thought were great! It is a beautiful home
Guest favourite
Home in Tisbury
4.93 out of 5 average rating, 70 reviews

Classic Downtown Property

larryRating, 5 stars6 months ago
Elizabeth is a wonderful host - responsive and friendly. The home is lovely and just a short walk from town. The living area has an open floor plan, with a well appointed kitchen and lots of comfortable living room furniture - a nice space for hanging out in the evenings. The beds are very comfortable and the bedrooms are quiet. The bathrooms were very clean and showers have great water pressure. There's a very thorough guest guide with everything you need to know about the house... heat, tv, garbage, etc... plus lots of helpful recommendations for restaurants, shopping and attractions. A great house whether you're traveling with family or friends - we felt very much at home.
Guest favourite
Home in Tisbury
4.86 out of 5 average rating, 69 reviews

Your home away from home

CristinaRating, 5 stars8 months ago
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

    $166 CAD 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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