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

Search Hotels with Pool in Chatham

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Chatham Hotels with Pool

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

Four sun loungers aligned along a poolside with a tiled floor.
A modern kitchen with white cabinetry, a wooden island with two barstools, and a decorative wall art piece.
A modern bedroom with a wooden wardrobe, a white robe hanging on the door, and a bed with a wooden frame.
A white house with a grey roof, surrounded by a well-maintained lawn and flowering bushes.

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.
Rp3.977.327
Rp5.201.939 total
includes taxes & fees
1 Sept - 2 Sept
Greyfinch Chatham Inn
A swimming pool with clear blue water, surrounded by blue and white lounge chairs.
A house with a brick exterior, white exterior walls, and a front porch with white chairs.
An outdoor patio with white metal chairs and a table, surrounded by blooming pink trees.
A white desk with a woven hat, a vase with white flowers, and two glasses of white wine.

2. Chatham Seafarer Inn

Chatham Seafarer Inn
Chatham
  • Splash into serenity at the seasonal outdoor pool, where relaxation flows from morning until evening.
Rp4.500.360
Rp5.150.470 total
includes taxes & fees
17 Sept - 18 Sept
Chatham Seafarer Inn
A swimming pool with lounge chairs and a white fence.
A sandy beach path with a wooden fence leading to the ocean, under a partly cloudy sky.
An outdoor seating area with tables and chairs, a sign for 'Wild Goose Tavern', and large windows.
A garden with a pergola structure, a pathway, and a seating area.

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.
Rp6.323.435
Rp8.009.140 total
includes taxes & fees
26 Aug - 27 Aug
Chatham Wayside Inn
A swimming pool with blue water, surrounded by lounge chairs and a waterfall feature.
A bedroom with a large bed, two side tables with lamps, a wooden nightstand, a wooden dresser, and a large window with a view of greenery.
A dining area with a glass table, chairs, and a vase with flowers.
A circular wooden structure with illuminated edges in a garden setting.

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.
Rp5.204.601
Rp5.956.665 total
includes taxes & fees
9 Sept - 10 Sept
Pleasant Bay Village Resort
A resort pool with multiple sun loungers and umbrellas, surrounded by beach views and boats.
A pathway leading to a beach with boats in the background and a building with a tower.
A series of tents with beds and seating areas, surrounded by a garden with various plants and a wooden deck.
A deck with white Adirondack chairs and a small round table, overlooking a beach and ocean.

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.
Rp10.311.520
Rp11.801.535 total
includes taxes & fees
14 Sept - 15 Sept
Chatham Bars Inn
A swimming pool with a metal ladder, surrounded by colorful plastic chairs, a red umbrella, and a building with a wooden exterior.
A kitchen with a brick stove, a white countertop, and a sign labeled "POOL TOWELS".
A modern bathroom with a glass-enclosed shower, a white sink, and a towel rack with folded towels.
A dining area with round tables and chairs, floral centerpieces, and decorative wall signs.

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.
Rp2.408.400
Rp2.756.458 total
includes taxes & fees
2 Sept - 3 Sept
Olde Tavern Motel And Inn
A swimming pool with lounge chairs and a building in the background.
A bedroom with a bed, a table, two chairs, a lamp, and a window with curtains.
An outdoor patio with round tables and chairs, picnic tables, and umbrellas.
A sign for Handkerchief Shoals Inn with a well-maintained garden in the foreground.

7. Handkerchief Shoals Inn

Handkerchief Shoals Inn
South Harwich
Rp3.162.694
Rp3.619.705 total
includes taxes & fees
17 Sept - 18 Sept
Handkerchief Shoals Inn
A clear swimming pool with blue lounge chairs and a blue umbrella.
Three children playing in shallow water on a beach.
A restaurant with brick arches, wooden tables, and chairs. There is a bar area with bottles and a television screen.
A golf course with sand bunkers, trees, and a clear blue sky.

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.
Rp2.744.906
Rp3.954.048 total
includes taxes & fees
20 Sept - 21 Sept
The Villages at Ocean Edge
A swimming pool with a fenced area, lounge chairs, and a building in the background.
A covered patio with a round table and four chairs.
A bathroom with a toilet, sink, and shower.
A brick building with a white picket fence, a lawn, and a sign for Skaket Beach Motel.

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.
Rp2.484.720
Rp2.843.761 total
includes taxes & fees
14 Sept - 15 Sept
Skaket Beach Motel
A hotel with a pool area, multiple balconies, and a fenced deck with lounge chairs.
A beverage station with a Coca-Cola machine, ice dispensers, and a variety of drink options.
A miniature golf course with two holes, a small pond, and a wooden bridge.
A reception desk with a marble top, a wooden panel base, a desk lamp, a potted plant, and a wicker chair with a cushion.

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.
Rp2.112.012
Rp2.417.100 total
includes taxes & fees
30 Aug - 31 Aug
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

Greyfinch Chatham Inn

Greyfinch Chatham Inn

10/10 Excellent
"Clean room and great location"
Sara 3-night trip
Posted 8 hours ago
Greyfinch Chatham Inn
Margaritaville Resort Cape Cod

Margaritaville Resort Cape Cod

10/10 Excellent
"Our stay at Margaritaville was superb. The hotel was clean and the rooms were delightful. The staff was very friendly and helpful. Very family friendly."
Ellen 3-night trip
Posted 10 hours ago
Margaritaville Resort Cape Cod
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 1 day 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 2 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 2 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 3 days ago
Chatham Wayside Inn

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.

Explore a world of travel with Expedia