Holiday rentals with a pool in Chatham

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Popular amenities for Chatham rentals with a pool

House rentals with a pool

Superhost
Home in Orleans
4.92 out of 5 average rating, 26 reviews

5-bedroom Cape with a pool and yard games.

CatherineRating, 5 stars9 months ago
We enjoyed our stay very much ~ the house and large fenced yard w/deck (perfect for pup) are amazing & the hosts were very kind, accommodating & responsive. The location was great with a short ride to local beaches and/or Chatham for a fun day of shopping or night out. The host’s welcome basket with treats & seltzers were a great surprise after a long day of travel. We loved playing ping pong in the garage! I do suggest the listing bedroom descriptions & photos be updated as we were pleased to find a king bed in the master BR (vs the queen shown) and a full bed (vs the twin) in the downstairs guest-room. Perhaps renovations are underway so we were pleasantly surprised! The only improvements I would suggest are adding a screen door to the deck & heat for the pool, having more wine glasses (the kitchen was wonderfully stocked otherwise), & adding amenities like blankets, washcloths, a hair dryer, beach/pool towels & chairs (we brought our own). We hope to be back next year!!
Guest favourite
Home in New Seabury
5 out of 5 average rating, 21 reviews

Exclusive New Seabury Home w/ Heated Pool ⛳️🏖🦞☀️🐠

DonnaRating, 5 stars4 days ago
This place worked out wonderfully for the 6 adults and 3 grandchildren we had with us, my 4 year old granddaughter even got her own room and loved it, along with the pool!! It was very clean and family friendly and stocked with more than we expected. There is also food and shops within walking distance. We enjoyed it immensely!! Thank you Michael, you have a wonderful place!!
Superhost
Home in Plymouth
4.82 out of 5 average rating, 17 reviews

Mansion with Heated Pool Near Ocean

AnayRating, 5 stars4 weeks ago
The place was nice and spacious. Great for large family gatherings. The pool was nice and although the water was not heated (which may partially have been due to the weather), Zachary and his team were very responsive and helped troubleshoot pool temperature. Overall we had a great stay!
Superhost
Home in Harwich
4.82 out of 5 average rating, 17 reviews

4 BD slice of Harwich Heaven

AndreaRating, 5 stars3 days ago
We absolutely loved our stay in Harwich! This house is so well stocked and spacious. Our kids absolutely loved swimming in the pool and relaxing in the sun room. The host, Chris, was incredibly communicative and helpful when we needed something. Highly recommend this home to families traveling to Cape Cod!
Guest favourite
Home in Dennis Port
4.92 out of 5 average rating, 53 reviews

Walk to the beach or sit poolside! Updated studio!

JoanneRating, 5 stars5 days ago
Amanda's place was a wonderful retreat for me and my son. It was walkable to the beach, close to bike trails, and nice restaurants in area. Happy to find a wagon for the beach that she provided. she also had beach chairs and provided all that you need. she was responsive to any questions.
Top Guest favourite
Home in Oak Bluffs
4.93 out of 5 average rating, 199 reviews

Spectacular beach & pool combo; beautiful sunsets!

RobynRating, 5 stars1 week ago
Resort vibes with a chef's kitchen and stunning views! ***** Our stay at Larry's house was fantastic! The kitchen was absolutely amazing - spacious, modern, and fully equipped with everything we needed. We enjoyed cooking and gathering there. The real highlight was the outdoor space. The view was breathtaking! The pool and hot tub made it feel like we were staying in a private resort. Michael was helpful and responsive, making everything easy from check in to check out. We would love to come back.
Top Guest favourite
Home in Hyannis Port
5 out of 5 average rating, 14 reviews

Home in Hyannis Port

MelissaRating, 5 stars1 day ago
Great, central location in the Cape. The decor was perfect for the coastal vibe. Home was very comfortable & welcoming. Backyard is fantastic to unwind by the pool & fire. The outdoor shower was a hit. We were a group of 8 women who were very comfortable for sleeping arrangements & bathrooms. The home was very clean. Host was very friendly & responsive. Definitely would recommend!!
Superhost
Home in East Sandwich
4.92 out of 5 average rating, 66 reviews

Large Home Heated Swimming Pool Private Beach

SahilRating, 5 stars4 weeks ago
We had a great stay at this place! The house was exactly as described—clean, comfortable, and well-stocked with everything we needed. Check-in was smooth, and the host provided clear instructions throughout. The neighborhood was quiet and convenient, with easy access to local attractions and restaurants. Would definitely recommend this spot to anyone visiting the area!

Condo rentals with a pool

Guest favourite
Condo in Provincetown
4.97 out of 5 average rating, 216 reviews

P-Town Beach Beauty on the Bay. Water View!

OctaviaRating, 5 stars2 weeks ago
Rob was a great host ! He responded within a timely manner and the place was very clean and felt just like home. I would suggest bringing board games and such for the rainy days. For the folks who enjoy cooking the kitchen was fully stocked with everything you need. I would also recommend renting bikes or taking an Uber if you don't like walking. The walk to town was about 25 minutes. Overall great stay would love you stay her again it gives you the peace and quiet while also being close enough to everything and a beautiful view of the ocean.
Guest favourite
Condo in Dennis Port
4.78 out of 5 average rating, 59 reviews

Cozy Studio Just Steps Away From the Beach!

ChrisRating, 5 stars2 days ago
Great place for a long weekend. Easy walk to the beach and a couple of restaurants (many others a short drive).
Guest favourite
Condo in Dennis Port
4.84 out of 5 average rating, 77 reviews

Comfy Cape Escape! Spacious, Cozy, Close to Beach!

KristinaRating, 5 stars4 days ago
Stayed here while in town for the week. Everything was as described . Super short walk to local beach . Short drive to food etc. had a great time thank you!
Guest favourite
Condo in Tisbury
4.91 out of 5 average rating, 74 reviews

Sunny 2bedroom condo w pool, walk to town

LaurelRating, 5 stars1 week ago
Leah was the most accommodating host I’ve ever encountered. The beds were super comfortable and the house was pristine. Leah gave tons of recommendations for me and my 2 under 2. We had a great time despite the weather and I would highly recommend Leah’s place to anyone.
Superhost
Condo in Provincetown
4.9 out of 5 average rating, 30 reviews

Spectacular Waterfront Condo

MeganRating, 5 stars8 months ago
What a special place to have your morning coffee, overlooking the gorgeous ocean views! The place was spotless, exactly as pictured, super clear entry and instructions. So close to all P’town has to offer but just far enough off the main strip for some real peacefulness! Would recommend to anyone! Hosts provide excellent local information and were incredibly communicative. Thank you!
Guest favourite
Condo in Provincetown
4.93 out of 5 average rating, 102 reviews

Modern, clean waterviews

LexiRating, 5 stars1 month ago
We had a wonderful stay at Garrett’s place. The apartment location can’t be beat, right on the water and walking distance to town but also nice and peaceful. Our family enjoyed the balcony and the comfy living room and kitchen. Would recommend!
Superhost
Condo in Falmouth
4.74 out of 5 average rating, 19 reviews

Condo in Falmouth MA

BrandiRating, 5 stars1 month ago
Patrick is a fantastic host and was very proactive and responsive when we ran into a problem outside anyone’s control. We would definitely recommend this home and host to others traveling to the area
Superhost
Condo in West Yarmouth
4.75 out of 5 average rating, 4 reviews

Cape Cod, South Yarmouth July 19-26. Sleeps 8

RickyRating, 5 stars35 months ago
Loved the location and the apartment was facing the water, which meant a light cool breeze most of the time all day and night. The 2 bedroom apt was very clean and spacious and the 5 of us did not get in each of our ways. While inside, we did not hear any noise from our next door neighbors and sliding doors silenced any outdoor noise. The AC was cold and very comfortable. Amenities including additional outdoor access to a peaceful water area with picnic tables, Adirondack chairs was a huge plus. Indoor pool helped too with two little ones. Beach parking passes at a discount. Staff was very nice and accommodating. Parking was easy and plenty of spaces. Would recommend and we would stay again.

Quick stats about holiday rentals with a pool in Chatham

  • Total rentals

    40 properties

  • Nightly prices starting at

    $266 NZD before taxes and fees

  • Total number of reviews

    320 reviews

  • Family-friendly rentals

    30 properties are a good fit for families

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wi-Fi availability

    40 properties include access to Wi-Fi

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