Holiday rentals with a pool in Chatham

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Popular amenities for Chatham rentals with a pool

House rentals with a pool

Top guest favourite
Home in North Eastham
5 out of 5 average rating, 18 reviews

Heated Pool, Game Room, Projector Room, Private

AstridRating, 5 stars3 weeks ago
If i could give more than 5 starts I would! Stephanie and her place were exceptional! We had a bachelorette party and we stayed at Stephanie’s place. Stephanie went out of her way to help me decorate for the bachelorette party. She was very responsive and so helpful throughout my planning. The house is amazing! Looks exactly like the photos and it is clean and in a safe and quiet neighborhood. There 11 of us and we fit comfortably! Thank you so much for hosting us Stephanie and to anyone booking I would 100% recommend staying here!
Superhost
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
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!!
Superhost
Home in Plymouth
4.82 out of 5 average rating, 17 reviews

Mansion with Heated Pool Near Ocean

AnayRating, 5 stars2 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
4.79 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.
Superhost
Home in East Sandwich
4.92 out of 5 average rating, 65 reviews

Large Home Heated Swimming Pool Private Beach

SahilRating, 5 stars2 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!
Top guest favourite
Home in Cotuit
4.95 out of 5 average rating, 114 reviews

Private Pool, near beaches, 3 BR/3 BA, Central Air

ZackRating, 5 stars8 months ago
Awesome stay! Great house/location and Sandy is an awesome host. Highly recommend
Guest favourite
Home in Hyannis Port
5 out of 5 average rating, 6 reviews

Townhouse on the beach, pool, walk to Main St.

CarolynRating, 5 stars3 days ago
We had a great time staying at this scenic location! It was a nice, clean, good value townhouse located very close to the waterfront with beach access. It had ample bedrooms and bathrooms, linens/towels, and modern kitchen with appliances among the many amenities. Alex was very responsive whenever I messaged. Thanks for sharing your lovely home!

Apartment rentals with a pool

Guest favourite
Apartment in Dennis Port
4.78 out of 5 average rating, 58 reviews

Cozy Studio Just Steps Away From the Beach!

NupurRating, 5 stars9 months ago
Perfect little studio for two people! Great location - close to beaches and restaurants and there’s even a pool! Michael was super responsive and the place was exactly like the pictures!
Guest favourite
Apartment in Dennis Port
4.84 out of 5 average rating, 76 reviews

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

ChrisRating, 5 stars9 months ago
Wonderful beach location. We enjoyed the local walkable beaches and restaurants. Close to anywhere in the cape , we had a great trip.
Superhost
Apartment in West Dennis
4.84 out of 5 average rating, 51 reviews

Hidden Hideaway

JennyRating, 5 stars7 months ago
The location is fabulous and very close to many amenities - coffee, groceries, restaurants and the beach. While it was a small space, it was well laid out, comfortable to be in, very clean and had a respectable kitchen for its small size (which I used). Devon was very proactive and friendly when I asked him about the microwave not working - I had missed that it wasn't plugged in! The condo was very quiet at night even though it is close to a road. I will definitely return to Devon's place should I need to travel there and it is available.
Guest favourite
Apartment in Tisbury
4.9 out of 5 average rating, 73 reviews

Sunny 2bedroom condo w pool, walk to town

ShayRating, 5 stars7 months ago
We had a great time at Leah’s place. She is a terrific communicator, immediate responses. She also reached out to share about local fun events that were happening during our stay. So nice! We would definitely stay there again.
Superhost
Apartment in Provincetown
4.9 out of 5 average rating, 30 reviews

Spectacular Waterfront Condo

MeganRating, 5 stars7 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
Apartment in Provincetown
4.93 out of 5 average rating, 102 reviews

Modern, clean waterviews

LexiRating, 5 stars3 weeks 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
Apartment in Falmouth
4.72 out of 5 average rating, 18 reviews

Condo in Falmouth MA

MarkRating, 5 stars1 month ago
The Condo was clean & comfortable. Having two bedrooms with queen beds was perfect for us, and sharing the 1 bathroom worked fine. The price was better than most other options. It was peaceful, and very quiet during our stay (in early May). Having the pool available would be very nice in summer months.
Superhost
Apartment in Hyannis Port
4.82 out of 5 average rating, 17 reviews

Beachfront Complex in Hyannis

ErinRating, 5 stars10 months ago
I loved our stay . The place inside was bigger than I was expecting. They have so many dishes, glasses, towels, blankets, chairs, etc to use. The place was great, just wish our weather was better. Thank you for being so helpful before and during our stay . Hope to return next year .

Quick stats about holiday rentals with a pool in Chatham

  • Total rentals

    40 properties

  • Nightly prices starting at

    ₹13,702 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

  • Wifi availability

    40 properties include access to wifi

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