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Check availability on Chatham Hotels with Pool

Tonight
22 Aug - 23 Aug
Tomorrow
23 Aug - 24 Aug
Next weekend
28 Aug - 30 Aug
In two weeks
4 Sep - 6 Sep

Our top choices for Chatham hotels with a pool

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 white house with a grey roof, surrounded by a well-maintained lawn and flowering bushes.
A modern bedroom with a wooden wardrobe, a white robe hanging on the door, and a bed with a wooden frame.

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.
฿7,321
฿9,576 total
includes taxes & fees
22 Sept - 23 Sept
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.
A beach with a fallen tree, clear blue water, and a forested shoreline.
A house with a brick exterior, white exterior walls, and a front porch with white chairs.

2. Chatham Seafarer Inn

Chatham Seafarer Inn
Chatham
  • Splash into serenity at the seasonal outdoor pool, where relaxation flows from morning until evening.
฿7,608
฿8,707 total
includes taxes & fees
22 Sept - 23 Sept
Chatham Seafarer Inn
A swimming pool with lounge chairs and a white fence.
A restaurant with long communal tables and booths, large windows, and a view of buildings outside.
A garden with a pergola structure, a pathway, and a seating area.
An outdoor seating area with tables and chairs, a sign for 'Wild Goose Tavern', and large windows.

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.
฿11,640
฿14,743 total
includes taxes & fees
24 Aug - 25 Aug
Chatham Wayside 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 covered porch with a lattice design, a stone pathway, and a view of a garden.
A dining area with a glass table, chairs, and a vase with flowers.

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.
฿7,890
฿9,030 total
includes taxes & fees
22 Sept - 23 Sept
Pleasant Bay Village Resort
A resort pool with multiple sun loungers and umbrellas, surrounded by beach views and boats.
A series of tents with beds and seating areas, surrounded by a garden with various plants and a wooden deck.
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.

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.
฿21,383
฿24,472 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 dining area with round tables and chairs, floral centerpieces, and decorative wall signs.
A hotel room with a large bed, teal walls, and a wooden headboard. There are two bedside tables with lamps and small plants.
A kitchen with a brick stove, a white countertop, and a sign labeled "POOL TOWELS".

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.
฿4,312
฿4,935 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.
A blue door labeled "Office" with a small window and a mailbox.
An outdoor patio with round tables and chairs, picnic tables, and umbrellas.

7. Handkerchief Shoals Inn

Handkerchief Shoals Inn
South Harwich
฿5,822
฿6,663 total
includes taxes & fees
16 Sept - 17 Sept
Handkerchief Shoals Inn
A clear swimming pool with blue lounge chairs and a blue umbrella.
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.
An outdoor patio with tables and chairs, umbrellas, and a view of the ocean.

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.
฿5,053
฿7,278 total
includes taxes & fees
21 Sept - 22 Sept
The Villages at Ocean Edge
A swimming pool with a fenced area, lounge chairs, and a building in the background.
A hotel room with two beds, a desk with a television, a red chair, and a window with green curtains.
A covered patio with a round table and four chairs.
A bathroom with a toilet, sink, and shower.

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.
฿4,574
฿5,235 total
includes taxes & fees
21 Sept - 22 Sept
Skaket Beach Motel
A hotel with a pool area, multiple balconies, and a fenced deck with lounge chairs.
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.
A beverage station with a Coca-Cola machine, ice dispensers, and a variety of drink options.

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.
฿3,888
฿4,449 total
includes taxes & fees
1 Sept - 2 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

Holiday Hill Inn & Suites

Holiday Hill Inn & Suites

8/10 Good
"Yes it’s good"
xin 1-night trip
Posted 7 hours ago
Holiday Hill Inn & Suites
Freebird Motor Lodge by Reverie Boutique Collection

Freebird Motor Lodge by Reverie Boutique Collection

10/10 Excellent
"Thoroughly enjoyed our 2 night stay at the freebird, which has a nice quirky vibe and was ideal for our whistle-stop tour of the cape. Room was spotless and welll equipped."
Philip 2-night trip
Posted 8 hours ago
Freebird Motor Lodge by Reverie Boutique Collection
Bayside Resort Hotel

Bayside Resort Hotel

10/10 Excellent
"We had a wonderful stay at the Bayside Resort in West Yarmouth! The entire property was exceptionally clean, including our room. We especially loved having both an indoor and outdoor pool to enjoy, and the kids had so much fun playing in the arcade! The staff was excellent—friendly, attentive, and responsive to all of our needs. We also appreciated the thoughtful touches throughout the resort, especially the Adirondack chairs overlooking Lewis Bay and the cozy fire pits at night. The complimentary breakfast each morning was another wonderful amenity and made our stay even more enjoyable. Bayside Resort is a beautiful, relaxing, and family-friendly place to stay. We would absolutely return!"
Shannon 5-night trip
Posted 10 hours ago
Bayside Resort Hotel
Hyannis Harbor Hotel

Hyannis Harbor Hotel

10/10 Excellent
"Our family of 5 had a wonderful time here. Across from the ferry Restaurants and Town center within walking distance. Lots of shopping in the town center Central Cape Cod location Best Ice cream right across the street Black Cat Restaurant is a must! They have a takeout window, a back area for casual dining, and main restaurant for upscale dining."
Nathaniel 3-night trip
Posted 11 hours ago
Hyannis Harbor Hotel
The Mariner Resort Cape Cod by The Red Collection

The Mariner Resort Cape Cod by The Red Collection

8/10 Good
"Great place for a family. The room was very clean. The only thing I would comment on was the bathroom was very small especially if you’re helping a child. It also needs some upgrades. I would definitely stay there again"
Barbara 1-night trip
Posted 14 hours ago
The Mariner Resort Cape Cod by The Red Collection
Holiday Inn Express Hyannis Cape Cod by IHG

Holiday Inn Express Hyannis Cape Cod by IHG

10/10 Excellent
"This hotel is the cleanest I’ve ever been to. The staff are very nice & friendly. And best of all it’s Pet Friendly. The only negative thing to me was the $40 a day pet fee. The last Holiday Inn Express I stayed at in Warwick, RI last week was only a $50 one time per stay fee which is more reasonable I would travel a lot more if the fee was lower. Other than that Holiday Inn express is my place to go to!! And the breakfast is out of this world. Although I don’t eat much in the morning."
Carolyn 2-night trip
Posted 16 hours ago
Holiday Inn Express Hyannis Cape Cod by IHG
Uncommoner Hotel by Reverie Boutique Collection

Uncommoner Hotel by Reverie Boutique Collection

10/10 Excellent
"Clean and quiet. Excellent cafe on site."
Patrick 1-night trip
Posted 17 hours ago
Uncommoner Hotel by Reverie Boutique Collection
Greyfinch Chatham Inn

Greyfinch Chatham Inn

10/10 Excellent
"Clean room and great location"
Sara 3-night trip
Posted 2 days ago
Greyfinch Chatham Inn
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 4 days ago
Queen Anne 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.

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