House vacation rentals in Chatham

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Popular amenities for Chatham house rentals

House rentals with a pool

Superhost
A spacious in-ground pool is surrounded by a sunbathing area featuring a lounge chair and umbrella. Lush greenery and flowering bushes frame the backyard, while a pool house is visible in the background, equipped with comfortable seating. The pool area invites relaxation and enjoyment.
Home in Barnstable
4.8 out of 5 average rating, 20 reviews

Stunning Cape Home - Inground Pool, 5 Min To Beach

KristenRating, 5 stars1 month 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 stars10 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!
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, 33 reviews

Modern Cape, Private Salt Water Pool, Beaches-Golf

MichaelRating, 5 stars1 week 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 stars7 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.
Top guest favorite
Home in Oak Bluffs
4.93 out of 5 average rating, 198 reviews

Spectacular beach & pool combo; beautiful sunsets!

AshleyRating, 5 stars4 days 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 stars1 week 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.
Superhost
A spacious heated pool surrounded by a concrete deck features lounge chairs for relaxation. Lush trees frame the area, providing a natural backdrop. The well-maintained yard continues beyond the pool, offering ample space for outdoor activities.
Home in East Falmouth
5 out of 5 average rating, 3 reviews

Spacious home with Pool! Close to Beaches & Town!

michaelRating, 5 stars9 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.
Superhost
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
4.91 out of 5 average rating, 43 reviews

Winslow Acres [heated] Pool Escape; pool May 15

TamiRating, 5 stars4 days ago
Our family loved this retreat!!

Weekly house rentals

Superhost
The exterior of the house showcases a wooden facade framed by lush greenery. A large wooden deck extends from the back, furnished with chairs, ideal for relaxation. Sunlight filters through the trees, highlighting the serene outdoor space.
Home in Yarmouth Port
4.88 out of 5 average rating, 153 reviews

* Walk to the beach - Swiss Beach House! *

JennaRating, 5 stars9 months ago
The Swiss House is an ideal retreat for families seeking a harmonious blend of comfort and connection. The expansive open-concept living area downstairs fostered a sense of togetherness, while the well-appointed kitchen made preparing family meals a breeze. Nestled away from the hustle, yet conveniently close to amenities, the house offers a perfect balance of privacy and accessibility. A quick drive to Mayflower Beach added to the allure, making our stay nothing short of delightful.
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 West Yarmouth
4.95 out of 5 average rating, 157 reviews

Cape Cod Life is Good Rentals

AngelinaRating, 5 stars1 week ago
Choo's home was beautiful! It was perfect for our family and friends trip to the Cape. It still felt roomy even with our group of 8. The area is quiet and peaceful. He was very responsive and helpful with our questions and plans.
Guest favorite
The cottage exterior is framed by well-maintained gardens and tall trees. A stone pathway leads to a front door, complemented by a skylight above. Solar panels are visible on the left side, outlining the home’s eco-friendly features.
Home in Wellfleet
4.98 out of 5 average rating, 45 reviews

Wellfleet home tucked in 1.5 acres of lush gardens

AlexRating, 5 stars1 week ago
Absolutely Wonderful Stay! This place was perfect , the house had everything we needed and more. My 2.5-year-old daughter especially loved the backyard and the abundance of toys. We truly didn’t want to leave and are already looking forward to coming back! Rebecca is an incredible host - warm, responsive, and so helpful. Her local recommendations were better than TripAdvisor, Yelp, and Google combined! We also loved the proximity to Wellfleet and the delicious PB Boulangerie bakery nearby. Highly recommend this stay to anyone visiting the area
Superhost
A contemporary cape-style home is framed by lush greenery and tall trees, set back from a sandy path leading to the entrance. The home features a charming front porch with large windows, offering a welcoming presence amidst the tranquil outdoor surroundings.
Home in Eastham
4.77 out of 5 average rating, 142 reviews

Contemporary Cape, Marsh/Bird Sanctuary views, AC!

ChrisRating, 5 stars9 months ago
My family and I recently stayed at Donna’s home for a long weekend on the Cape. The house was exactly as described, matched all photos, and was in a phenomenal location. Just a few minutes from all of the shops and restaurants in Orleans, the beaches, hiking along the national seashore, and the Cape Cod rail trail. We would definitely stay here again.
Top guest favorite
A patio area is presented with four modern seating chairs around a central table. The shaded space features a view of the lake, with grassy grounds extending to the water. Two kayaks are visible in the background, indicating recreational options nearby.
Home in South Yarmouth
4.94 out of 5 average rating, 234 reviews

Waterfront★ Hot Tub ★ Kayaks ★ Firepit ★ Pet OK

MaureenRating, 5 stars3 weeks ago
My family had a lovely stay. It is on a pond that had lots of wildlife (swans, turtles, loons). We kayaked. It has a nice hot tub. Fully stocked kitchen. It was very comfortable to enjoy a few days on the cape with an ideal location to visit different towns and beaches. The hosts were very responsive. We really enjoyed our stay at this location. The host provided great local recommendations. She allowed us to bring our two dogs which we were very appreciative.
Superhost
A cozy living area features a grey sofa and two patterned armchairs, arranged around a wooden coffee table. Natural light floods in through large windows dressed with sheer curtains, highlighting the warm wood flooring and the nautical wall decor.
Home in Dennis Port
4.65 out of 5 average rating, 136 reviews

Charming 4 bdrm 2 1/2 bth - fire pit - pet ok

RichardRating, 5 stars9 months ago
Sue’s place was great for my family and dog. The 2 apartments give a nice separation when staying with a group. Very clean and comfortable. We paid the extra fee to not worry about linens and felt It was worth it. It is on a busy road and you can definitely hear the traffic when the windows are open as the house is pretty close to the road but it wasn’t an issue for sleeping. Location is great for many restaurants and beaches. 20-25 minutes to Hyannis or Chatham
Top guest favorite
A classic Cape house with a gabled roof showcases a welcoming facade. The exterior features red shutters, multiple windows, and landscaped gardens with flowering plants. A gravel driveway leads up to the entrance, which is framed by decorative shrubs, contributing to a peaceful, inviting setting.
Home in Eastham
4.99 out of 5 average rating, 140 reviews

Bayside Bliss

SandraRating, 5 stars9 months ago
The home was absolutely beautiful and perfect for our family stay. The neighborhood was peaceful and private. The beach was 1.4 miles from the home, so we enjoyed walking there. The home furnishings were very clean and comfortable. The home was well stocked with everything we could possibly need. The host was excellent, keeping in touch with updates leading up to our stay, and throughout the process. We couldn't have found a more perfect home for our vacation in Eastham. I would highly recommend the home and host for anyone considering a stay at the Cape.
Guest favorite
The charming exterior of a two-story home is visible, featuring wood shingles and a white picket fence. An inviting red door is framed by greenery, which enhances the home's appeal. Windows with shutters are positioned on the upper level, allowing for ample natural light.
Home in Provincetown
4.94 out of 5 average rating, 192 reviews

Location!! Large West End House w/ parking!

SavannahRating, 5 stars2 weeks ago
We enjoyed our stay! The home was in a very walkable area with restaurants, coffee shops, and shopping nearby. Only one thing I think is important to note- there were no linens for the sofa bed. We had 4 in our group and with only 3 bedrooms, one of us was planning to use the sofa bed. Unfortunately, when we messaged the owner to inquire about the linens, we received no help because we did not mention we would like to use the sofa bed before our arrival. So be mindful to mention if you’ll need to use the sofa bed during your stay.

Private house rentals

Superhost
Home in North Eastham
5 out of 5 average rating, 6 reviews

Spacious house with cottage w/AC. Near beaches!

LauraRating, 5 stars21 months ago
Wonderful peaceful setting and great for the whole family with the attached guest cottage! Prime location with access to ocean and bay beaches as well as ponds. We had an amazing week!
Superhost
The house exterior showcases a two-story structure nestled among tall pine trees. The wood siding is complemented by large windows, allowing natural light to enter. A driveway leads to the house, with greenery and grass providing a natural and serene setting.
Home in Wellfleet
4.73 out of 5 average rating, 52 reviews

Wellfleet, MA. Cape Cod sleeps 8

AnthonyRating, 5 stars1 month ago
What a great cape house in Wellfleet. Cliff and Rob were very helpful and made the stay a pleasure. Would recommend this spot to anyone who wants to check out the Wellfleet area
Superhost
A spacious living area features a light tan sectional sofa adorned with decorative cushions. A wooden coffee table sits on a textured area rug. Natural light streams through window treatments, illuminating the neutral color palette and enhancing the artwork displayed on the walls.
Home in North Eastham
4.78 out of 5 average rating, 18 reviews

The Sandpiper

AndrewRating, 5 stars9 months ago
Easy access to restaurants, grocery stores, beach and mini golf! Great area to take a walk or run around the neighborhood. Had all the basic supplies for cooking and comfortable furniture in the living room and bedrooms. The outdoor patio and yard is where we spent most of our time, the chairs and set up was perfect. The outdoor shower is a nice touch too!
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, 135 reviews

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

AprilRating, 5 stars1 month ago
We had a great time!!! Perfect for a nice relaxing girls weekend.
Guest favorite
A charming single-story house is surrounded by well-maintained gardens featuring colorful hydrangeas and tidy shrubbery. A private driveway is visible alongside the house, complemented by a rustic wooden fence that adds to the property's warmth. The front entrance is framed by seasonal blooms.
Home in Dennis Port
4.96 out of 5 average rating, 68 reviews

Quaint Cape Beach House

SamanthaRating, 5 stars5 months ago
The house was cozy, quaint, and spotless—perfect for our off-season weekend getaway! Adele was incredibly accommodating and flexible with us, and her communication was top-tier. We couldn’t have asked for a better experience and would happily stay again. Highly recommend!
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 Eastville
4.83 out of 5 average rating, 193 reviews

Waterview, Private, Walk to Beach, Mile to Town

LaurenRating, 5 stars7 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 spacious home is set against a backdrop of lush trees, showcasing a unique architectural design with a multi-level roof. A wrap-around deck is visible, enhancing the outdoor space surrounded by greenery and landscaped gardens.
Home in Vineyard Haven
5 out of 5 average rating, 60 reviews

Well-Appointed 3 Bedrm 4 Bathrm w/ 50+ 5* Reviews

ElizabethRating, 5 stars9 months ago
Lisa is an incredible host! She was very responsive and easy to reach. The house was very clean and neat and well equipped to make your stay easy and enjoyable. You can really tell that she cares about the home and the comfort of her guests. The home is located in a very quiet lowkey neighborhood with easy access to town and everything you need either by bike or car. I would definitely stay there again.
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
4.79 out of 5 average rating, 29 reviews

Holiday in the sun!

BrettRating, 5 stars2 weeks ago
Craig’s place was perfect! We felt right at home staying here with our two huskies. The fenced in backyard was a huge plus! Secluded on a quiet dead end street. We met one of the neighbors during our stay who was super friendly! Thanks Craig for your hospitality!

Quick stats about house rentals in Chatham

  • Total rentals

    450 properties

  • Nightly prices starting at

    $80 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

Destinations to explore