Find Hotels with a Pool in Chatham, MA
Upfront pricingOur total price for your stay includes taxes and fees
Treat yourselfSave 10% or more on over 100,000 hotels worldwide with Member PricesLearn about One Key
Be pickySearch almost a million properties worldwide
Check availability on Chatham Hotels with a Pool
Tonight
Aug 30 - Aug 31Tomorrow
Aug 31 - Sep 1Next weekend
Sep 4 - Sep 6In two weeks
Sep 11 - Sep 13Our 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.
$238 nightly
$273 total
Sep 27 - Sep 28
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.
$233 nightly
$267 total
Sep 22 - Sep 23
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.
$397 nightly
$454 total
Sep 24 - Sep 25
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.
$217 nightly
$249 total
Sep 30 - Oct 1
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.
$655 nightly
$749 total
Sep 14 - Sep 15
Total with taxes and fees
6. The Chatham Motel
The Chatham MotelChatham
- Soak up summer vibes in this Cape Cod retreat with a seasonal outdoor pool, playground, and peaceful garden setting.
$275 nightly
$315 total
Aug 31 - Sep 1
Total with taxes and fees
7. 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.
$109 nightly
$125 total
Sep 2 - Sep 3
Total with taxes and fees
8. The Villages at Ocean Edge
The Villages at Ocean EdgeBrewster
- Dive into paradise with 7 amazing pools, each offering a different vibe for every vacation mood.
$187 nightly
$214 total
Sep 20 - Sep 21
Total with taxes and fees
View all properties
Top Chatham Hotel Reviews
Cape Sands Inn
10/10 Excellent
"The cape sands inn was the best choice for our stay! Centrally located, they have everything you could need. The pools were amazing! Staff was friendly enough despite their limited staffing. The fire pit was a true highlight! We even extended our stay an extra night because the only thing we missed during our trip was just a relaxing day at the motel!"
Bayside Resort Hotel
8/10 Good
"Pros-The pool inside and outside were great and the gaming room had a good selection. The free breakfast had a good variety and fire pit on site bar where we could toast samores. It was very picturesque and not too far from the bars and restaurants on Main Street. Cons- the room was damp and housing keeping pretty non existent. We got new towels but the room was not cleaned most days ."
Freebird Motor Lodge by Reverie Boutique Collection
10/10 Excellent
"Clean and convenient"
Uncommoner Hotel by Reverie Boutique Collection
10/10 Excellent
"Great location! Clean rooms, 2 great pools!"
Holiday Hill Inn & Suites
10/10 Excellent
"Everything was nice. We had booked two rooms, somehow one room was more bigger and more upgraded than the other. Easy to park , and one of the best thing was their shower. Very close to the mini golf and bumper cars/ acade games. Free bus every hour."
The Villages at Ocean Edge
8/10 Good
"Clean room"
Hyannis Harbor Hotel
10/10 Excellent
"I would highly recommend this hotel for Its location, amenities and comfortable rooms. It was a nice place"
Greyfinch Chatham Inn
10/10 Excellent
"Clean room and great location"
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!"
Frequently asked questions
Explore a world of travel with Expedia
- Hotels with Fireplaces in Chatham
- Hotels with Balconies in South Yarmouth
- Hotels with Suites in West Yarmouth
- Hotels on the Lake in Cape Cod
- Hotels with Balconies in Cape Cod
- Historic Hotels in South Yarmouth
- Hotels with Air Conditioning in Cape Cod
- Hotels with Bars in Chatham
- Hotels with smoking rooms in Yarmouth Port
- Oceanfront Hotels in Cape Cod
- Romantic Hotels in South Yarmouth
- Beach Hotels in Chatham
- Luxury Hotels in Chatham
- Hotels with a View in Cape Cod
- Resorts & Hotels with Spas in Hyannis
- Family Hotels in West Yarmouth
- Hotels with Free Wifi in Cape Cod
- Oceanfront Hotels in Yarmouth Port
- Cheap Hotels in Cape Cod
- Hotels with Connecting Rooms in South Yarmouth
- Hotels with Connecting Rooms in Hyannis
- Family Hotels in Cape Cod
- Hotels with Air Conditioning in South Yarmouth
- Historic Hotels in Chatham
- Adults Only Resorts & in Chatham
- Hotels with Laundry Facilities in Hyannis
- Hotel Wedding Venues Hotels in West Yarmouth
- All-Inclusive Resorts in Yarmouth Port
- Cheap Hotels in South Yarmouth
- Gay friendly Hotels in Cape Cod
- Hotels with Hot Tubs in West Yarmouth
- Hotels with Tennis Courts in Chatham
- Hotels with smoking rooms in Chatham
- All-Inclusive Resorts in Cape Cod
- Beach Hotels in Cape Cod
- All-Inclusive Resorts in Chatham
- Hotels with a Pool in West Yarmouth
- Oceanfront Hotels in Dennis Port
- Hotels with an Outdoor Pool in West Yarmouth
- Business Hotels in Cape Cod
- Hotels with Free Wifi in Dennis Port
- Family Hotels in Chatham
- Hotels with smoking rooms in West Yarmouth
- Casino Hotels in Chatham
- Fishing Resorts & in Cape Cod
- Hotels with Hot Tubs in Chatham
- Golf Hotels in West Yarmouth
- Hotels with Childcare in Cape Cod
- Hotels with Fireplaces in Cape Cod
- Luxury Hotels in South Yarmouth
- Hotels with Laundry Facilities in Cape Cod
- Waterpark Hotels in Hyannis
- Hotels with Free Airport Shuttle in Cape Cod
- Hotels with Restaurants in Cape Cod
- Hotels with Laundry Facilities in Chatham
- Cheap Hotels in Chatham
- Waterpark Hotels in West Yarmouth
- Hotels with smoking rooms in Cape Cod
- Romantic Hotels in Hyannis
- Gay friendly Hotels in Yarmouth Port
- Hotels with a Swim-up Bar in Hyannis
- Hotels with Kitchenettes in Chatham
- Luxury Hotels in Yarmouth Port
- Hotels with Kitchenettes in Hyannis
- Hotels with Hot Tubs in South Yarmouth
- Hotels & Resorts for Couples in South Yarmouth
- Hotels with a Lazy River in Cape Cod
- Hotels with Tennis Courts in Cape Cod
- All-Inclusive Resorts in West Yarmouth
- Extended Stay Hotels in Chatham
- Hotels with Free Parking in Cape Cod
- Hotels with Waterslides in Cape Cod
- Waterpark Hotels in Chatham
- Oceanfront Hotels in Chatham
- Hotels with Bars in Yarmouth Port
- Beach Hotels in West Yarmouth
- Hotel Wedding Venues Hotels in Chatham
- Hotels with Bars in Hyannis
- Hotels with smoking rooms in Hyannis
- Extended Stay Hotels in West Yarmouth
- Hotels with smoking rooms in South Yarmouth
- Hotels with Connecting Rooms in Cape Cod
- Pet-Friendly Hotels in Chatham
- Family Hotels in Yarmouth Port
- Hotels with Early Check-in in Cape Cod
- Hotels with Laundry Facilities in West Yarmouth
- Hotels with an Indoor Pool in Chatham
- Historic Hotels in Cape Cod
- Winery Hotels in Cape Cod
- Hotels with Kitchenettes in West Yarmouth
- Hotels with Air Conditioning in Chatham
- Resorts & Hotels with Spas in West Yarmouth
- Romantic Hotels in Chatham
- Hotels with Free Breakfast in West Yarmouth
- Pet-Friendly Hotels in Cape Cod
- Golf Hotels in South Yarmouth
- Hotels with Room Service in Cape Cod
- Adults Only Resorts & in Yarmouth Port
- Quiet Resorts & in Cape Cod
- Luxury Hotels in West Yarmouth