Find Hotels with a Pool in Chatham, MA
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Aug 15 - Aug 16Tomorrow
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Aug 21 - Aug 23In two weeks
Aug 28 - Aug 30Our 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.
$278 nightly
$318 total
Sep 8 - Sep 9
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.
$578 nightly
$662 total
Sep 14 - Sep 15
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.
$129 nightly
$148 total
Sep 1 - Sep 2
Total with taxes and fees
$178 nightly
$204 total
Sep 14 - Sep 15
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 3 - Sep 4
Total with taxes and fees
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Top Chatham Hotel Reviews
Uncommoner Hotel by Reverie Boutique Collection
10/10 Excellent
"More style than substance. Just about gets away with it but our room was described with a bath but only had a shower. Met with shrug by staff. Food choice average. As seems to be usual nowadays expected to give 20% plus tip for serving myself at a counter."
All Seasons Resort, Trademark Collection by Wyndham
10/10 Excellent
"My family has stayed here before it was redone and I am pleased with the upgrades. The only treadmill wasn’t working the morning I was there, so that was the only annoying thing."
Freebird Motor Lodge by Reverie Boutique Collection
10/10 Excellent
"The hotel was amazing, there was so much to do. The staff was nice and everyone we encountered treated us with great hospitality. I would highly recommend this place for anyone who is looking for a Cape experience."
Bayside Resort Hotel
8/10 Good
"The rooms at the Bayside are very basic and could use some upgrading; the back, outside areas are what make it stand out. The pool, although on the smaller side, has a very fun vibe with the Tiki bar and music, and a sandy area to play cornhole. The adirondacks facing the marsh are a lovely spot to sit in the morning or evening. Our kids loved the continental breakfast (“best pancakes ever”) and the game room. Breakfast was often crowded and could use some more fruit/fresh options, but it was an appreciated perk. The tiki bar/inside bar only have a very limited menu of a few sandwiches and uncrustables, FYI, so don’t plan on eating in. Also, there are no elevators, so request the first floor if that’s an issue—or you have a lot of stuff to carry in and out. Overall, a good family-friendly hotel on the strip, with free parking and breakfast. We would stay again!"
Holiday Inn Express Hyannis Cape Cod by IHG
8/10 Good
"We stayed one night before taking an early ferry the next day. The hotel was clean and breakfast was good - it was everything we needed for a short stay."
Holiday Hill Inn & Suites
8/10 Good
"Convenient location"
Chatham Wayside Inn
10/10 Excellent
"Spacious room, lovely pool, clean, great location (heart of downtown)"
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."
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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