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 20 - Aug 21Tomorrow
Aug 21 - Aug 22This weekend
Aug 21 - Aug 23Next weekend
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 7 - Sep 8
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.
$254 nightly
$290 total
Sep 17 - Sep 18
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.
$394 nightly
$451 total
Aug 26 - Aug 27
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.
$284 nightly
$325 total
Sep 7 - Sep 8
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.
$135 nightly
$155 total
Sep 2 - Sep 3
Total with taxes and fees
$178 nightly
$204 total
Sep 14 - Sep 15
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.
$195 nightly
$223 total
Sep 20 - Sep 21
Total with taxes and fees
View all properties
Top Chatham Hotel Reviews
Margaritaville Resort Cape Cod
10/10 Excellent
"Everything was great! Such a nice place."
Uncommoner Hotel by Reverie Boutique Collection
10/10 Excellent
"Clean rooms , friendly staff , delicious breakfast , indoor outdoor pools , our room was overlooking a lake, very quite , highly recommend"
Cape Sands Inn
8/10 Good
"This was a great property for the night. One downside was the lack of microwave. The room came with a little fridge but no microwave which would have been nice. The room itself was clean and easily accessible!"
Queen Anne Inn
8/10 Good
"The staff was very helpful for suggesting places to eat and visit"
The Mariner Resort Cape Cod by The Red Collection
8/10 Good
"The front desk staff were nice and friendly. The beds were comfortable. The lobbies were nice. The pools could have been a bit cleaner, the mini golf needs some attention, and the breakfast is okay (coffee terrible). Overall, was a good stay and we’d go back. Definitely not a resort tho."
Chatham Wayside Inn
8/10 Good
"Great location, close to the famous Squire and the restaurant (Wild Goose Tavern) on-site was terrific and made the experience a positive one. Elena makes an awesome martini, and Bobby was a friendly welcoming personality. Ben was awesome during dinner. Hotel staff should take lessons from the restaurants customer service training. Front Desk team is as cold as Elena’s martinis. Never a greet or smile unless we initiated. Not very welcoming. Room was fine. Bathroom not fine. Never stood in a tub that creaked before. Cheap bath fitter tub/shower, hospital room bathroom feel. Bed was comfy. Small pool which served its purpose for a quick refreshing dip. Wound consider a return but definitely wound explore other options as well."
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!"
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