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

Search Hotels with Swimming Pool in Chatham

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Check availability on Chatham Hotels with Swimming Pool

Tonight
23 Oct - 24 Oct
Tomorrow
24 Oct - 25 Oct
This weekend
23 Oct - 25 Oct
Next weekend
30 Oct - 1 Nov

Our top choices for Chatham hotels with a pool

A swimming pool with lounge chairs and a white fence.
A garden with a pergola structure, a pathway, and a seating area.
A restaurant with long communal tables and booths, large windows, and a view of buildings outside.
A sandy beach path with a wooden fence leading to the ocean, under a partly cloudy sky.

1. 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.
₹16,130
₹22,586 total
includes taxes & fees
2 Nov - 3 Nov
Chatham Wayside Inn
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.
An aerial view of a beach with rows of sunbeds and umbrellas, a pier extending into the water, and a small building near the beach.
A series of tents with beds and seating areas, surrounded by a garden with various plants and a wooden deck.

2. 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.
₹36,674
₹41,973 total
includes taxes & fees
5 Nov - 6 Nov
Chatham Bars Inn
A swimming pool with blue water, surrounded by lounge chairs and a waterfall feature.
A circular wooden structure with illuminated edges in a garden setting.
A dining area with a glass table, chairs, and a vase with flowers.
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.

3. 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.
Pleasant Bay Village Resort
Four sun loungers aligned along a poolside with a tiled floor.
A modern bathroom with a double sink vanity, a large mirror, and a glass-enclosed shower area.
A modern kitchen with white cabinetry, a wooden island with two barstools, and a decorative wall art piece.
A white house with a grey roof, surrounded by a well-maintained lawn and flowering bushes.

4. 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.
₹16,010
₹21,795 total
includes taxes & fees
1 Nov - 2 Nov
Greyfinch Chatham Inn
A swimming pool with clear blue water, surrounded by blue and white lounge chairs.
A white desk with a woven hat, a vase with white flowers, and two glasses of white wine.
An outdoor patio with white metal chairs and a table, surrounded by blooming pink trees.
A house with a brick exterior, white exterior walls, and a front porch with white chairs.

5. Chatham Seafarer Inn

Chatham Seafarer Inn
Chatham
  • Splash into serenity at the seasonal outdoor pool, where relaxation flows from morning until evening.
₹22,082
₹25,272 total
includes taxes & fees
25 Oct - 26 Oct
Chatham Seafarer Inn
A pool area with lounge chairs and a fire pit, surrounded by stone walls and potted plants.
A resort with a swimming pool, beach area, and a large building with a dome structure.
A sunlit room with a view of the sea, featuring a sofa, a round table, and a chair.
A balcony with wicker furniture, a table with a vase and wine glass, and a view of the sea.

6. Wequassett Resort and Golf Club

Wequassett Resort and Golf Club
Harwich
  • Swim through summer in a luxury cabana paradise with poolside bars and ocean breezes.
₹33,733
₹41,310 total
includes taxes & fees
8 Nov - 9 Nov
Wequassett Resort and Golf Club
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.
A blue door labeled "Office" with a small window and a mailbox.
A sign for Handkerchief Shoals Inn with a well-maintained garden in the foreground.

7. Handkerchief Shoals Inn

Handkerchief Shoals Inn
South Harwich
₹16,834
₹19,267 total
includes taxes & fees
26 Oct - 27 Oct
Handkerchief Shoals Inn
An aerial view of a residential property with a swimming pool, a gazebo, and a well-maintained lawn.
A modern kitchen with stainless steel appliances, wooden cabinets, and a marble countertop.
A sandy beach with gentle waves and a clear sky.
A building with a red door, black shutters, and hanging flower baskets.

8. Eagle Wing Inn - Cape Cod

Eagle Wing Inn - Cape Cod
Eastham
  • Dive into the inviting outdoor pool at this coastal retreat with comfortable sun loungers and peaceful gardens.
₹17,069
₹19,535 total
includes taxes & fees
24 Oct - 25 Oct
Eagle Wing Inn - Cape Cod
A swimming pool with lounge chairs and a covered seating area.
A two-story house with a front porch, a mailbox, and a well-maintained garden.
A covered porch with white Adirondack chairs, a trash can, and a door marked with the number 9.
A hotel room with a bed, a bench, a desk, a microwave, and a television.

9. Pelham on Earle

Pelham on Earle
West Harwich
  • Coastal getaway with a seasonal outdoor pool where relaxation awaits after exploring Cape Cod's beautiful beaches.
₹17,855
₹22,069 total
includes taxes & fees
26 Oct - 27 Oct
Pelham on Earle
A swimming pool with lounge chairs and umbrellas, surrounded by greenery and a building.
A hotel room with a large bed, two bedside tables, a wall-mounted painting, and a patterned carpet.
A hotel reception area with a blue wall, a reception desk, a large window, and a welcome mat.
A bathroom with a shower curtain, a bathtub, and a tiled wall with a marble-like pattern.

10. Rodeway Inn Orleans - Cape Cod

Rodeway Inn Orleans - Cape Cod
Orleans
  • Splash into refreshing luxury with a clean, spacious pool perfect for sunny Cape Cod afternoons.
₹10,410
₹11,914 total
includes taxes & fees
26 Oct - 27 Oct
Rodeway Inn Orleans - Cape Cod
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

Hyannis Travel Inn

Hyannis Travel Inn

8/10 Good
"We loved the two gentlemen who helped at the check in desk when we arrived - very knowledgeable and helpful!"
Linda 1-night trip
Posted 9 hours ago
Hyannis Travel Inn
Bayside Resort Hotel

Bayside Resort Hotel

8/10 Good
"Staff very friendly"
suzanne 3-night trip
Posted 14 hours ago
Bayside Resort Hotel
Uncommoner Hotel by Reverie Boutique Collection

Uncommoner Hotel by Reverie Boutique Collection

8/10 Good
"The rooms are very uniquely decorated which is quite enjoyable. It seems like it was a renovation so some older finishes are still in place, but overall looks great. A/C was a little finicky, may have just been our room. We didn’t go to the pool but it looked cool as well."
Michael 3-night trip
Posted 16 hours ago
Uncommoner Hotel by Reverie Boutique Collection
Greyfinch Chatham Inn

Greyfinch Chatham Inn

10/10 Excellent
"Quaint smaller property. Room was spacious and bed very comfortable. Had a plug issue and was fixed immediately. Grounds are immaculate. Sat by the fire pit in back area near the pool. Great location a minute away from downtown Chatham."
Kimberly 2-night trip
Posted 1 day ago
Greyfinch Chatham Inn
Margaritaville Resort Cape Cod

Margaritaville Resort Cape Cod

8/10 Good
"Overall, the hotel and our room were lovely. There was a large event taking place during our stay, and a significant number of younger guests from the event were gathered throughout the public areas. While completely understandable, it did make it difficult for us to enjoy those spaces. Our only real disappointment was breakfast. We needed something quick and were directed to the to-go area, but waited more than 20 minutes for a simple breakfast sandwich. When it was made incorrectly, the interaction felt unnecessarily dismissive and we were made to feel as though the mistake was our fault. A little more customer-service-minded handling would have made a big difference. Aside from that experience, we had a lovely room and enjoyed our stay overall."
Anne 4-night trip
Posted 1 day ago
Margaritaville Resort Cape Cod
Riviera Beach Resort

Riviera Beach Resort

10/10 Excellent
"Wonderful hotel, clean and right on the beach. Will stay they again!"
AGNIESZKA 7-night trip
Posted 2 days ago
Riviera Beach Resort
Hyannis Harbor Hotel

Hyannis Harbor Hotel

10/10 Excellent
"Great location, staff was extremely helpful"
N. 1-night trip
Posted 2 days ago
Hyannis Harbor Hotel
Chatham Bars Inn

Chatham Bars Inn

10/10 Excellent
"Amazing property and staff."
Sylvia 3-night trip
Posted 5 days ago
Chatham Bars Inn
Cape Cod Family Resort and Parks

Cape Cod Family Resort and Parks

10/10 Excellent
"Excellent experience"
April 2-night trip
Posted 11 days ago
Cape Cod Family Resort and Parks

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?
Spend some time experiencing the great outdoors at Chatham Lighthouse Beach and Ridgevale Beach. During your stay, visit sights such as Chatham Lighthouse, Cape Cod Beaches and Cape Cod National Seashore. 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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