A boat on a calm river, a large house with a red roof, and dense greenery in the background.

Hotels with Swimming Pools in Chatham

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Check availability on Chatham Hotels with Swimming Pools

Tonight
21 Aug - 22 Aug
Tomorrow
22 Aug - 23 Aug
This weekend
21 Aug - 23 Aug
Next weekend
28 Aug - 30 Aug

Our top choices for Chatham hotels with a pool

1. Greyfinch Chatham Inn

Greyfinch Chatham Inn
Chatham
  • Escape to the Cape Cod oasis with a seasonal outdoor pool, free bicycles, and modern comforts just steps from local beaches.
S$373
includes taxes & fees
7 Sept - 8 Sept
Greyfinch Chatham Inn

2. Chatham Seafarer Inn

Chatham Seafarer Inn
Chatham
  • Splash into serenity at the seasonal outdoor pool, where relaxation flows from morning until evening.
S$369
includes taxes & fees
17 Sept - 18 Sept
Chatham Seafarer Inn

3. Chatham Wayside Inn

Chatham Wayside Inn
Chatham
  • Dive into seaside bliss at this Cape Cod hotel with a sun-soaked seasonal pool and relaxing loungers for perfect summer days.
S$574
includes taxes & fees
26 Aug - 27 Aug
Chatham Wayside Inn

4. Pleasant Bay Village Resort

Pleasant Bay Village Resort
Chatham
  • Splash into holiday bliss at this Cape Cod retreat with outdoor pool and soothing hot tub.
S$422
includes taxes & fees
7 Sept - 8 Sept
Pleasant Bay Village Resort

5. Chatham Bars Inn

Chatham Bars Inn
Chatham
  • Dive into beachside bliss with a private shoreline, seasonal pool, and chauffeured beach shuttle for ultimate seaside luxury.
S$841
includes taxes & fees
14 Sept - 15 Sept
Chatham Bars Inn

6. Olde Tavern Motel And Inn

Olde Tavern Motel And Inn
Orleans
  • Soak in coastal charm at the seasonal outdoor pool surrounded by lush garden views at this beautifully renovated motel.
S$196
includes taxes & fees
2 Sept - 3 Sept
Olde Tavern Motel And Inn

7. Handkerchief Shoals Inn

Handkerchief Shoals Inn
South Harwich
S$259
includes taxes & fees
14 Sept - 15 Sept
Handkerchief Shoals Inn

8. The Villages at Ocean Edge

The Villages at Ocean Edge
Brewster
  • Dive into paradise with 7 amazing pools, each offering a different vibe for every holiday mood.
S$283
includes taxes & fees
20 Sept - 21 Sept
The Villages at Ocean Edge

9. Skaket Beach Motel

Skaket Beach Motel
Orleans
  • Dive into relaxation at this coastal motel's seasonal outdoor pool, just steps from beautiful Skaket Beach and sunset views.
S$200
includes taxes & fees
13 Sept - 14 Sept
Skaket Beach Motel

10. Holiday Hill Inn & Suites

Holiday Hill Inn & Suites
Dennis Port
  • Sparkling family-friendly pool oasis awaits at this beach-convenient motel with mini golf fun.
S$170
includes taxes & fees
2 Sept - 3 Sept
Holiday Hill Inn & Suites
View all properties

Choose what matters most at hotels with a pool in Chatham

Breakfast included
Hot tub
4 stars
5 stars
Spa

Top Chatham Hotel Reviews

Cape Sands Inn

Cape Sands Inn

8/10 Good
"Okay"
Donielle 1-night trip
Posted less than an hour ago
Cape Sands Inn
Greyfinch Chatham Inn

Greyfinch Chatham Inn

10/10 Excellent
"Clean room and great location"
Sara 3-night trip
Posted 18 hours ago
Greyfinch Chatham Inn
Uncommoner Hotel by Reverie Boutique Collection

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"
Christine 2-night trip
Posted 2 days ago
Uncommoner Hotel by Reverie Boutique Collection
Queen Anne Inn

Queen Anne Inn

8/10 Good
"The staff was very helpful for suggesting places to eat and visit"
Douglas 3-night trip
Posted 3 days ago
Queen Anne Inn
The Mariner Resort Cape Cod by The Red Collection

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."
Mindy 2-night trip
Posted 3 days ago
The Mariner Resort Cape Cod by The Red Collection
Chatham Wayside Inn

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."
Richard 3-night trip
Posted 4 days ago
Chatham Wayside Inn
Pleasant Bay Village Resort

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!"
Courtney 2-night trip
Posted 12 days ago
Pleasant Bay Village Resort

Frequently asked questions

What are some accommodation options with pools in Chatham?
Chatham Bars Inn: Resort, 4-minute walk from Cape Cod Beaches. Features a private beach, a seasonal outdoor pool and a full-service spa. Chatham Wayside Inn: Hotel, 11-minute walk from Cape Cod Beaches. Offers daily, a seasonal outdoor pool and free self parking. The Chatham Motel: Provides free self parking, a seasonal outdoor pool and complimentary wireless Internet access.
What is there to see and do in Chatham?
Explore places such as Cape Cod Beaches while you're in Chatham. Make a point to visit attractions such as Chatham Lighthouse Beach and Chatham Railroad Museum. Visitors to Chatham speak highly of the natural attractions, including the beautiful beaches.
When is the best time to book a hotel with a pool in Chatham?
Taking the local weather in Chatham into account is an important factor for planning your visit, especially if you plan to spend your trip by the pool. The hottest months are usually August and July, with an average temperature of 19°C, while the coldest months are February and January, with an average of 3°C. Average annual precipitation for Chatham is 1362 mm.

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