Find Hotels with a Pool in Chatham, MA
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Check availability on Chatham Hotels with a Pool
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Aug 13 - Aug 14Tomorrow
Aug 14 - Aug 15This weekend
Aug 14 - Aug 16Next weekend
Aug 21 - Aug 23Our top choices for Chatham hotels with a pool
1. Greyfinch Chatham Inn
Greyfinch Chatham InnChatham
- Escape to the Cape Cod oasis with a seasonal outdoor pool, free bicycles, and modern comforts just steps from local beaches.
$256 nightly
$293 total
Sep 1 - Sep 2
Total with taxes and fees
2. Chatham Seafarer Inn
Chatham Seafarer InnChatham
- Splash into serenity at the seasonal outdoor pool, where relaxation flows from morning until evening.
$289 nightly
$330 total
Sep 10 - Sep 11
Total with taxes and fees
3. Chatham Wayside Inn
Chatham Wayside InnChatham
- Dive into seaside bliss at this Cape Cod hotel with a sun-soaked seasonal pool and relaxing loungers for perfect summer days.
$434 nightly
$497 total
Aug 31 - Sep 1
Total with taxes and fees
4. Pleasant Bay Village Resort
Pleasant Bay Village ResortChatham
- Splash into vacation bliss at this Cape Cod retreat with outdoor pool and soothing hot tub.
$290 nightly
$332 total
Aug 28 - Aug 29
Total with taxes and fees
5. Chatham Bars Inn
Chatham Bars InnChatham
- Dive into beachside bliss with a private shoreline, seasonal pool, and chauffeured beach shuttle for ultimate seaside luxury.
$727 nightly
$832 total
Sep 3 - Sep 4
Total with taxes and fees
6. Olde Tavern Motel And Inn
Olde Tavern Motel And InnOrleans
- Soak in coastal charm at the seasonal outdoor pool surrounded by lush garden views at this beautifully renovated motel.
$139 nightly
$159 total
Sep 1 - Sep 2
Total with taxes and fees
7. Wequassett Resort and Golf Club
Wequassett Resort and Golf ClubHarwich
- Swim through summer in a luxury cabana paradise with poolside bars and ocean breezes.
$433 nightly
$496 total
Sep 8 - Sep 9
Total with taxes and fees
8. Holiday Hill Inn & Suites
Holiday Hill Inn & SuitesDennis Port
- Sparkling family-friendly pool oasis awaits at this beach-convenient motel with mini golf fun.
$105 nightly
$120 total
Sep 10 - Sep 11
Total with taxes and fees
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Top Chatham Hotel Reviews
Margaritaville Resort Cape Cod
10/10 Excellent
"Beautifully renovated resort. We loved that the room keys were wrist bracelets, easy to keep track of. The room was clean, fun, nautical theme touches, and very comfortable bed. The pool and waterpark were super fun for kids, they also had a great arcade. We ate dinner at their restaurant Landshark, solid food, but the wait was extremely long. They did compensate us well with a free drink and dessert, which was much appreciated. The breakfast buffet was extra, but not too much, and also very good. The grounds had additional games such as cornhole, tetherball, and large chess. Music in the late afternoon in the courtyard was a nice touch. Highly recommend, will definitely be back!"
Uncommoner Hotel by Reverie Boutique Collection
10/10 Excellent
"Great place!! Everybody love it!! Pools, roooms, activities, view. Perfect for vacation"
All Seasons Resort, Trademark Collection by Wyndham
10/10 Excellent
"Cleaned and everything is there"
Chatham Wayside Inn
10/10 Excellent
"Spacious room, lovely pool, clean, great location (heart of downtown)"
Bayside Resort Hotel
10/10 Excellent
"Will absolutely come back with our kids again. The continental breakfast was a great way to quickly fuel up the family before we departed to do activities versus wasting time finding food in the AM. The pools were both great and the kids loved the arcade."
Greyfinch Chatham Inn
10/10 Excellent
"The property was nice and clean. Ideal for a short stay for our family. The staff was very friendly and responsive."
The Mariner Resort Cape Cod by The Red Collection
8/10 Good
"Hotel a great stay excellent location for what I was doing. Literally across the st from the inflatable park. Also has miniature golf on site 2 pools a play ground and free breakfast. Although breakfast could be better my kids enjoyed making there waffles. Only complaint is I requested a late check out for 12 and which was approved... I was resting my last 20 mins before my long trip home and house keeping decides to knock on the door and walk in. I explained I have late check out until 12. She argued with me that it was only until 11:30, kept talking over me then basically called me a liar and slammed the door closed. I informed the front desk about the issue they did nothing but apologize and confirm that my check out was in fact at 12. Customer service can certainly be improved"
Cape Sands Inn
10/10 Excellent
"We felt very at ease; the kids really enjoyed the pools, the room was very clean, and the beds were very comfortable. I will be back."
Pleasant Bay Village Resort
10/10 Excellent
"Thoroughly enjoyed our visit. Perfect weekend in a perfect location. The grounds were beautiful, staff attentive. Rooms were amazing and clean. Even the turn down service was top notch. I will definitely plan another stay!"
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