House vacation rentals in Chatham

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Popular amenities for Chatham house rentals

House rentals with a pool

Top guest favorite
An expansive outdoor area features a rectangular saltwater pool surrounded by a concrete deck. The historic house presents a mix of shingle-style architecture and modern updates. Lush greenery and trees frame the property, with clouds and blue skies providing a scenic backdrop.
Home in East Sandwich
5 out of 5 average rating, 30 reviews

XL Estate: 2 Homes-Pool-Tennis-Game Barn - 20 ppl

AngelaRating, 5 stars1 month ago
This property was perfect for our group of 18. Everything was just as described; we wanted for nothing. The Cape Cod coastal vibe is perfect. Joshua was a dream to work with, as he answered my many questions in a timely manner. I'm sure I drove him crazy, but he never let on. The heated salt water pool and game room were favorites. We enjoyed them so much, we canceled an activity or two to enjoy them more. The tennis court was another wonderful well-utilized bonus. No one wanted to sit around on their phones with so much to do on the property, as well as, in the area. The beds were comfortable, and I loved the tub in my room so much, I've already ordered one just like it. They provided shampoo, etc...and even aloe, which too many of us needed. The kitchen was also well stocked with essentials. There were many lovely areas to gather, both for dining and living, but we mostly used the outdoor living spaces. I finished our trip on the porch swing, wishing we had booked one more night.
Guest favorite
The spacious outdoor area features a heated saltwater pool surrounded by paver stones. Lounge chairs are positioned around the pool, accompanied by blue umbrellas. A nearby cabana is visible, along with vibrant landscaping, providing a relaxing atmosphere for guests.
Home in Popponesset
5 out of 5 average rating, 12 reviews

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

CarolRating, 5 stars1 month 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.
Guest favorite
A spacious heated saltwater pool is surrounded by a large deck featuring colorful lounge chairs and an umbrella. The attractive two-story house stands in the background, framed by lush greenery and trees, creating a peaceful outdoor setting.
Home in Brewster
4.97 out of 5 average rating, 34 reviews

Modern Cape, Private Salt Water Pool, Beaches-Golf

MichaelRating, 5 stars2 weeks ago
Our stay with Walt was incredible! The place came exactly as described and matched all of the photos. It also had all of the necessary ammenities when hosting large group of 11 people. Plenty of places to sleep, plenty of blankets and towels. Walt was extremely responsive and easy to communicate with when I had questions while we were in his residence. 10/10 would recommend!!
Superhost
The exterior of the home is presented with natural wood siding, complemented by green shutters. Solar panels are mounted on the roof. A welcoming front porch leads to the main entrance, while a garage is visible to the left amidst well-maintained landscaping.
Home in Harwich
4.79 out of 5 average rating, 14 reviews

4 BD slice of Harwich Heaven

KimberlyRating, 5 stars8 months ago
Chris is always a great host. He communicates. Is considerate of our soccer schedule and accommodations. He even wishes our boys good luck at their soccer tournament! He is understanding and a great host. We really enjoy staying here. I highly recommend staying here. He’s a great host.
Guest favorite
A bright studio unit features a queen-sized bed with a comfortable pull-out sofa nearby. Natural light floods the space through large windows. A small dining table with two chairs is positioned next to the seating area, providing a functional living space.
Home in Dennis Port
4.92 out of 5 average rating, 50 reviews

Walk to the beach or sit poolside! Updated studio!

RobinRating, 5 stars2 weeks ago
We stayed during Memorial Day weekend and picked Amanda's place because of the close location to a family weekend gathering. It was perfect, I couldn't be happier and will definitely be booking again. We didn't need a lot of the amenities offered due to the proximity of family, but it would be ideal for anyone looking for a clean, cute and cozy beach getaway. I highly recommend!
Top guest favorite
Home in Oak Bluffs
4.93 out of 5 average rating, 198 reviews

Spectacular beach & pool combo; beautiful sunsets!

AshleyRating, 5 stars1 week ago
Came here for a girls weekend. I think it’s even better than the photos! We had a great time!!!
Superhost
Home in Plymouth
4.9 out of 5 average rating, 120 reviews

Seaview Summit | Ocean Views, Indoor Pool, Beach

EllieRating, 5 stars2 weeks ago
This house was spectacular. More amenities than I would have ever thought of. Gorgeous interior and exterior. The surrounding neighborhood is in need of regentrification but it’s extremely safe and quiet. Once in the home., it’s an oasis. Probably the best Airbnb I’ve stayed in (sample size about 10) Tony is extremely responsive and helpful. This was the perfect home for my daughter’s bridal party to get ready in and shoot pre wedding photos in. Also amazingly comfortable for my large family to stay in for the long weekend.
Top guest favorite
An outdoor space features a landscaped area with lush greenery and a fenced backyard. A heated plunge pool is surrounded by stone patio tiles. Comfortable seating is arranged under a shaded umbrella, inviting relaxation in a peaceful setting.
Home in Yarmouth Port
5 out of 5 average rating, 9 reviews

Yarmouthport house heated pool/hot tub near beach.

AngeliqueRating, 5 stars1 week ago
Wonderful place to stay! So comfortable and lots of space! Close to lots of restaurants and shopping! Would definitely stay again!

Weekly house rentals

Superhost
A spacious dining area features a large wooden table surrounded by dark chairs, complemented by a decorative centerpiece of fresh flowers. Natural light streams in from windows, illuminating the room, while a cozy living area is visible through the open doorway.
Home in Chatham
4.96 out of 5 average rating, 26 reviews

Main St fun for groups! Game barn! Walk to town!

JasonRating, 5 stars8 months ago
I can't say enough about how great our experience was. Chris and Nat were great communicators and gave us some local references for places to eat. Their home is beautiful and has the perfect location with easy access to anywhere one may want to go. The home was very comfortable with great updates but still had a bit of the original charm from it's era of construction. I would highly recommend.
Guest favorite
The exterior of a recently renovated house is shown, featuring blue siding and white trim. Two symmetrical green shrubs accompany the entrance, which has a red door adorned with a decorative wreath. Windows with red shutters provide a balanced look to the facade.
Home in South Chatham
5 out of 5 average rating, 30 reviews

Chatham House Close to Beaches and Bike Path.

JoannaRating, 5 stars2 weeks ago
We had the best time staying here for our girls weekend! The space was just like the photos—super clean so comfortable for a group. There was plenty of room for everyone to relax and sleep comfortably, and the living area was cozy and great for hanging out. The location was great too—close to everything we needed but still quiet and peaceful. Highly recommend this place for any group getaway. We’d absolutely come back!
Superhost
A cozy living area features a striped sofa adorned with colorful throw pillows. A wooden rocking chair and a uniquely shaped table are included. Natural light enters through two window panes, illuminating the space. Artwork depicting beach chairs hangs on the wall.
Home in Chatham
4.67 out of 5 average rating, 21 reviews

Cozy Chatham Cape Cod Cottage

CristianRating, 5 stars2 weeks ago
Joseph was an amazing host! Helpful with recommendations and quick to respond. The cottage was so cute and in the perfect location. Can’t wait to stay here again!
Top guest favorite
A light-filled living area showcases comfortable seating with a couch and swivel chairs, all designed for optimal views of the waterfront. Large glass doors open to a scenic outdoor space, seamlessly connecting indoor and outdoor living.
Home in South Dennis
5 out of 5 average rating, 63 reviews

Beachfront· Sauna· Screened Patio· 2Kings· DogsYes

KendallRating, 5 stars1 day ago
I loved my stay at Arianna and Tara’s place. Everything was so thoughtful and mindful including the soothing music that was playing upon arrival. A and T’s Airbnb was an example of how great an Airbnb can be. Five stars!!
Guest favorite
Home in Brewster
5 out of 5 average rating, 18 reviews

Newly remodeled cottage with path to beach

CamilleRating, 5 stars1 week ago
The cottage is beautiful, extremely comfortable and well equipped. The surroundings are peaceful and the location is conveniently at walking distance from the beach. We loved our stay there and spent an amazing week.
Top guest favorite
A charming beach house with shingle-style siding is displayed, set within a landscaped yard. Two large bushes frame the entryway, and the building features multiple rooflines and skylights. A brick pathway leads to the front door, with trees providing partial shade in the foreground.
Home in Chatham
4.98 out of 5 average rating, 82 reviews

Beachfront Charmer! Newly Renovated.

DeborahRating, 5 stars1 week ago
8 lobser lane is everything described and more! Steve was amazing every step of the way and ensured our stay was special. An incredible host! This is a bucket list home and location... we will be back for sure!
Guest favorite
The charming yellow house is set against a twilight sky, framed by a white fence and lush greenery. Warm light spills from the windows, casting a welcoming glow on the front porch, which features a bright red door, inviting guests to explore the home.
Home in South Chatham
5 out of 5 average rating, 6 reviews

Happy Yellow House, Walk to Ridgevale Beach!

JamesRating, 5 stars7 months ago
The Happy Yellow House was all I hoped for and more. Clean and well equipped, and very comfortable. The location couldn't be beat! Right down the street from a beautiful Nantucket sound beach and close to the amenities of Chatham. The house is in a quiet neighborhood of summer homes and was very peaceful. Caitlin is a superb host and responded promptly when there was a little snafu with a faulty smoke detector (at 10pm!), offering to have an electrician out on an emergency basis. (The electrician had just serviced the smoke detectors. As Host, Caitlin couldn't have been more pro-active or responsive) Luckily, I was able to solve the problem by simply removing and replacing the batteries. I would not hesitate to book this rental again.
Top guest favorite
The outdoor deck is shown with a dining area featuring a large table surrounded by black wicker chairs. An umbrella provides shade, while lush grass and garden elements frame the space. The house's light blue siding and chimney are visible, complementing the serene backyard setting.
Home in Harwich Port
5 out of 5 average rating, 46 reviews

Beautiful, Family Friendly, under 1 mile to Beach

KathrynRating, 5 stars2 weeks ago
Such a great place! The home was clean, organized, and exactly as pictured. Located in a quiet neighborhood, it was an easy walk to the beach and just a short drive to downtown areas. We also appreciated the clean/non-toxic soaps in the house. We didn’t have any kids with us, but this place is definitely set up to be kid friendly. Check-in was easy and Anthony even offered to ship a piece of jewelry we left behind. Responsive & trustworthy hosts. Would highly recommend staying here!

Private house rentals

Guest favorite
A spacious outdoor deck features comfortable, cushioned seating with a view of the ocean. A table is positioned centrally, inviting gatherings. The tranquility of the scene is enhanced by natural grass and the serene waters in the background, creating an ideal relaxing space.
Home in South Yarmouth
4.95 out of 5 average rating, 55 reviews

Oceanfront Vacation Home with Private Beach for 6

JeffreyRating, 5 stars3 days ago
This is a true hidden gem. A stones throw from one of the best raw bars in Yarmouth (or Cape Cod for that matter), literally steps (like 5 steps right out the slider) from the beach, stunning views and sunsets. Very clean and cozy cottage, and our host was excellent. The value was also incredible. Very central in Cape Cod, meaning anything you want to do besides Provincetown is 30 mins or less in any direction. Yarmouth had a charm of its own, especially for a family with young children. Lots of kids activities within 5 minutes. A+++
Top guest favorite
The sunroom features a vaulted mahogany ceiling and brick wall, with large glass doors leading to the outdoor area. Comfortable seating surrounds a coffee table, and a dining area is adjacent to the bar with glassware. Coastal decor accents the space.
Home in Chatham
5 out of 5 average rating, 47 reviews

Modern, Newly Renovated, 3-bed Peach Tree House

SherryRating, 5 stars1 week ago
We had a great stay! The weather wasn’t great, but it didn’t spoil our time there because the house was so pristine and homey. We loved the screened in porch, all the games, and the house was well stocked with everything you need. Chatham itself is a beautiful area, with gorgeous beaches and great restaurants. Dale and Kimberly were very responsive…Highly recommend staying here!
Top guest favorite
A charming ranch-style home is presented, surrounded by a spacious green lawn and meticulously landscaped flower beds. A stone-lined path leads to the entrance, where vibrant orange flowers add a touch of color. The exterior features a combination of siding and a brick chimney.
Home in Harwich Center
5 out of 5 average rating, 42 reviews

* Top Rated - Free Cleaning & Linens - SuperHost!

LindaRating, 5 stars3 weeks ago
We stayed at Vince's for a wedding and it was super clean, perfect for three, and conveniently located. The house is adorable and the inside feels much larger than it appears from the outside. Enjoyed the back yard table; wasn't warm enough to use the outdoor shower ;-). Directions were very straight forward and clear and Vince provided all the info we needed before we needed it. Highly recommend.
Guest favorite
A cozy living area features soft seating, including a recliner and floral couch. Natural light pours in through skylights and large windows, illuminating the wooden walls and decorative accents. A wooden coffee table sits in the center, and a television is mounted on the wall.
Home in South Chatham
4.89 out of 5 average rating, 37 reviews

Chatham Beach Cottage

BarbaraRating, 5 stars3 weeks ago
The home was comfortable and charming. Beds were comfortable with plenty of blankets. Everything we needed. Beach is about 1/2 mile at the end of the road. Convenient to shopping and a wonderful pie shop. Lots of restaurants. I think we tried most.
Guest favorite
A charming coastal house is showcased with light blue shutters and a white exterior. Lush greenery and vibrant pink flowers surround the front yard. A brick chimney rises against a clear blue sky, while the roof features a gentle slope.
Home in South Chatham
5 out of 5 average rating, 16 reviews

Chatham Vibes

MeghanRating, 5 stars2 weeks ago
Beautiful home a short distance from the beach. Lovely neighborhood for walking and jogging. Close to bike path.
Top guest favorite
An outdoor area features a wooden sauna with a circular design among natural surroundings. A modern table with seating for six is positioned on a composite deck, accompanied by a wooden fence and nearby greenery. Clear blue skies provide a bright backdrop.
Home in South Yarmouth
5 out of 5 average rating, 6 reviews

Sauna I Walk2Beach I Pet Friendly I Fire Pit

MollyRating, 5 stars3 days ago
We loved our stay here! Spent the weekend with our two young children and the house had everything we could need and more. It was walking distance to the beach and near great restaurants. Victoria also provided a list of local recommendations which we took a few of and loved them all! Would recommend staying here.
Superhost
A charming cottage is framed by tall white pine trees, providing shade and privacy. The exterior features light-colored siding and blue shutters. Seating options include two outdoor chairs positioned on the ground amidst pine needles. A screened-in porch is visible on the right side of the building.
Home in South Chatham
4.87 out of 5 average rating, 38 reviews

Chatham cottage w/ laundry & AC! Walk to beach!

JenniferRating, 5 stars9 months ago
We loved Blair cottage for our little getaway. Jack & Sheryl make it very clear they were available if we needed them. The cottage was clean and cozy, everything worked great. The outdoor shower was a wonderful bonus for us with the beach sand! Cockle Cove was a short 15 minute walk and made for great exercise (because ice cream at Short n Sweet is only a 6 minute walk 😊). Breakfast in the enclosed front porch was a treat for us every morning. Thank you Jack & Sheryl for everything!
Guest favorite
A serene bedroom features a metal bed with white bedding and decorative pillows. Natural light pours in through two windows, enhancing the calming atmosphere. A ceiling fan circulates air above, while nightstands with lamps are positioned on either side, complemented by a patterned area rug beneath.
Home in South Chatham
4.94 out of 5 average rating, 35 reviews

Bird Watcher's Paradise! Renovated Chatham home

LauraRating, 5 stars9 months ago
This is our second stay at Sarah’s place and we had another amazing week on the cape. The house is truly just like home. She has thought of every single detail that a guest or family might need. We feel so comfortable and at ease. Sarah and I communicated a couple of times and she is so quick and responsive and helpful! I knew we were in the best of hands. The bird watching and outdoor shower make the outside so wonderful and peaceful. We enjoyed many nights of s’mores in the solo stove. The rooms are spacious and our family of 6 was never on top of each other. We just love it at the salty pearl and can’t wait to go back!

Quick stats about house rentals in Chatham

  • Total rentals

    450 properties

  • Nightly prices starting at

    ﺩ.ﺇ294 before taxes and fees

  • Total number of reviews

    10K reviews

  • Family-friendly rentals

    430 properties are a good fit for families

  • Pet-friendly rentals

    170 properties allow pets

  • Rentals with a pool

    30 properties have a pool

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