House vacation rentals in Chilmark

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Popular amenities for Chilmark house rentals

House rentals with a pool

Superhost
A spacious dining area is showcased from an elevated perspective, featuring a large wooden table surrounded by white woven chairs. Delicate blue plates rest atop the table, with a vibrant green arrangement at the center. Natural light floods the space through large glass doors.
Home in Barnstable
4.8 out of 5 average rating, 20 reviews

Stunning Cape Home - Inground Pool, 5 Min To Beach

KristenRating, 5 stars2 weeks 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!
Superhost
A serene backyard setting features a private pool surrounded by a spacious patio. A sunbathing chair and a BBQ grill are positioned nearby, with a house showcasing large windows that invite natural light. Lush greenery frames the area, providing a sense of tranquility.
Home in Dennis
4.63 out of 5 average rating, 30 reviews

House on Cape Cod with pool close to beach

KeelyRating, 5 stars8 months ago
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!
Superhost
A comfortable living area is framed by a stylish sectional sofa and wooden accent chair. A dark coffee table contrasts with light-toned walls, while a large screen is mounted above a wooden slatted feature. The open layout offers views of a contemporary kitchen in the background.
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 favorite
Home in Oak Bluffs
4.94 out of 5 average rating, 194 reviews

Spectacular beach & pool combo; beautiful sunsets!

JillRating, 5 stars1 month ago
The house was beautiful, very comfortable and extremely well equipped. I would highly recommend this home. We had a wonderful stay there!
Guest favorite
The living area features a calming color palette with wooden floors and large windows offering water views. A comfortable blue sofa and an accent chair create a welcoming seating arrangement. Natural light fills the space, enhancing the connection to the outdoors with a spacious deck visible.
Home in Tiverton
4.89 out of 5 average rating, 18 reviews

Waterfront Oasis Pool EPIC Views

SudyRating, 5 stars3 weeks ago
super fun! great for larger groups- plenty of space for everyone and a well-stocked house
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 favorite
The outdoor pool area is surrounded by a black metal fence and features clear blue water. A swan-shaped float is situated on the water, while lounge chairs are positioned nearby. An umbrella provides shade, enhancing the inviting setting.
Home in North Falmouth
5 out of 5 average rating, 14 reviews

New Construction Home with Pool in N. Falmouth

TaylorRating, 5 stars1 day ago
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.
Guest favorite
A well-maintained swimming pool reflects the greenery surrounding it, bordered by a stone deck. Poolside seating arrangements include a black metal table with chairs and a blue lounge chair. A red umbrella offers shade, while the exterior of the home features a wooden deck and bright lounge furniture.
Home in Yarmouth Port
4.9 out of 5 average rating, 42 reviews

Winslow Acres [heated] Pool Escape; pool May 15

JeannineRating, 5 stars8 months ago
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

Guest favorite
A sandy beach area is captured, featuring soft dunes and gentle ridges formed by the wind. A building with a distinctive cupola is visible in the distance, surrounded by wooden walkways. Clear blue skies complement the serene coastal setting.
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 favorite
The spacious kitchen features white cabinetry and a modern layout. A central island with seating is complemented by a dining table nearby. Natural light floods the area through sliding glass doors, enhancing the welcoming ambiance.
Home in Yarmouth
4.95 out of 5 average rating, 153 reviews

Cape Cod Life is Good Rentals

AllisonRating, 5 stars2 days ago
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!
Guest favorite
A stone pathway leads up to the side of a house, bordered by green grass and plants. The two-story structure features a textured wooden exterior and multiple windows. Natural light illuminates the scene under a clear blue sky.
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!!
Top guest favorite
A two-story cape cod home is showcased, featuring a light-colored exterior with blue shutters. A well-maintained driveway leads to a covered entryway, and a lush green lawn surrounds the property. Mature trees provide shade, enhancing the welcoming outdoor space.
Home in Teaticket
4.84 out of 5 average rating, 74 reviews

Expansive & Renovated Teaticket Cape

AnnieRating, 5 stars4 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 favorite
A grassy outdoor space features two blue Adirondack chairs and a small fire pit, surrounded by trees and overlooking a serene pond. A hammock hangs in the distance, while the deck is visible on the right, extending from the house.
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 favorite
A waterfront hot tub is set against a natural backdrop of trees and calm waters. Inside, a dining area features a large window with views of the lake. A cozy living room displays comfortable seating, while an outdoor patio has seating for relaxation and enjoying the scenery.
Home in South Yarmouth
4.94 out of 5 average rating, 232 reviews

Waterfront★ Hot Tub ★ Kayaks ★ Firepit ★ Pet OK

BrendanRating, 5 stars1 day ago
We had a great time. House was extremely clean and Aruna was fantastic with communication. Would recommend to anyone to hook this spot.
Superhost
A charming farmhouse is showcased, featuring a light grey exterior with white accents. Lush green grass surrounds the home, complemented by neatly trimmed bushes and trees. A welcoming front porch with seating invites relaxation in a tranquil outdoor setting.
Home in Westport
4.65 out of 5 average rating, 48 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!
Top guest favorite
The charming exterior of the classic Cape home is surrounded by lush greenery and well-maintained landscaping. A welcoming front pathway leads to an inviting entrance, flanked by two Adirondack chairs on the lawn, inviting relaxation in the peaceful outdoor setting.
Home in Barnstable
4.96 out of 5 average rating, 26 reviews

Downtown Osterville Updated 4 Bedroom

PaulaRating, 5 stars7 months ago
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

Top guest favorite
A spacious outdoor deck is surrounded by greenery and blooming flowers. A table with matching chairs occupies the center, complemented by an outdoor grill nearby. The soft colors of the area rug add warmth to the inviting space, perfect for gatherings.
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
The exterior of the home is presented at dusk, featuring soft outdoor lighting and classic blue siding. A pathway of stone leads to the entrance, flanked by neatly manicured shrubs and a lawn. A small porch area and steps provide access to the front door.
Home in Marstons Mills
4.88 out of 5 average rating, 134 reviews

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

AprilRating, 5 stars1 week ago
We had a great time!!! Perfect for a nice relaxing girls weekend.
Top guest favorite
Home in Yarmouth
5 out of 5 average rating, 12 reviews

Spacious Mid-Cape Home 5 Bedrooms, 9 Beds, 3 Bath

HannahRating, 5 stars5 months ago
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.
Superhost
An open concept living area features high cathedral ceilings with natural wood finishes. A modern gray sofa with red and black accent pillows is positioned near a vibrant wall art piece. Doorways lead to a dining area and kitchen, enhancing the spacious layout.
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!
Top guest favorite
A well-maintained exterior of a two-story home is surrounded by landscaped greenery. A stone pathway meanders through the neatly trimmed lawn, with flowering bushes and trees providing natural shade. The house features a combination of wood and shingle siding, with a small balcony visible on the upper level.
Home in East Falmouth
5 out of 5 average rating, 36 reviews

Spacious and immaculate custom home.

LeslieRating, 5 stars8 months ago
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!
Superhost
The exterior of the home is shown, featuring a spacious deck with seating overlooking a large, grassy backyard. The landscape is bordered by trees, with a fenced area visible in the background. A storage shed is located to the left in the distance.
Home in Sandwich
4.77 out of 5 average rating, 26 reviews

Holiday in the sun!

KaylaRating, 5 stars2 weeks 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 favorite
The exterior of a multi-level home is shown, featuring large windows and a wrap-around deck. A screened porch is visible on the lower level, while manicured grass surrounds the structure. The sky is clear, providing ample natural light to the setting.
Home in Dennis
4.92 out of 5 average rating, 50 reviews

Cape Cod Lakefront Home

JustinRating, 5 stars8 months ago
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.
Guest favorite
The exterior of a two-story house features natural shingle siding and a welcoming front porch. Lush hydrangeas line the walkway, providing a vibrant green and white contrast against the home. Multiple large windows invite natural light into the living spaces.
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

    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

Destinations to explore

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