
Holiday rentals with a pool in Chatham
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Top-rated rentals with a pool in Chatham
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Popular amenities for Chatham rentals with a pool
House rentals with a pool

5-bedroom Cape with a pool and yard games.
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!!

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

Mansion with Heated Pool Near Ocean
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!

4 BD slice of Harwich Heaven
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!

Walk to the beach or sit poolside! Updated studio!
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.

Spectacular beach & pool combo; beautiful sunsets!
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.

Home in Hyannis Port
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!!

Large Home Heated Swimming Pool Private Beach
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

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

Cozy Studio Just Steps Away From the Beach!
Great place for a long weekend. Easy walk to the beach and a couple of restaurants (many others a short drive).

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

Sunny 2bedroom condo w pool, walk to town
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.

Spectacular Waterfront Condo
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!

Modern, clean waterviews
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!

Condo in Falmouth MA
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

Cape Cod, South Yarmouth July 19-26. Sleeps 8
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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- Cape Cod
- Mayflower Beach
- West Dennis Beach
- East Sandwich Beach
- Craigville Beach
- Duxbury Beach
- Coast Guard Beach
- Sandwich Glass Museum
- Owen Park Beach
- Nickerson State Park
- Onset Beach
- Oyster Harbors Beach
- Inman Road Beach
- White Horse Beach
- Pinehills Golf Club
- Kalmus Park Beach
- Ridgevale Beach
- Chapin Memorial Beach
- Forest Beach
- Corporation Beach
- Linnell Landing Beach
- Cape Cod National Seashore
- Lighthouse Beach
- Ellis Landing Beach