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

Chatham Hotel with Pool

  • 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 Hotel with Pool

Tonight
10 Oct - 11 Oct
Tomorrow
11 Oct - 12 Oct
Next weekend
16 Oct - 18 Oct
In two weeks
23 Oct - 25 Oct

Our top choices for Chatham hotels with a pool

A resort pool with multiple sun loungers and umbrellas, surrounded by beach views and boats.
A deck with white Adirondack chairs and a small round table, overlooking a beach and ocean.
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.

1. 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.
HK$3,068
HK$3,512 total
includes taxes & fees
3 Nov - 4 Nov
Chatham Bars Inn
A swimming pool with lounge chairs and a white fence.
An outdoor seating area with tables and chairs, a sign for 'Wild Goose Tavern', and large windows.
A sandy beach path with a wooden fence leading to the ocean, under a partly cloudy sky.
A restaurant with long communal tables and booths, large windows, and a view of buildings outside.

2. 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.
HK$1,406
HK$1,950 total
includes taxes & fees
1 Nov - 2 Nov
Chatham Wayside Inn
A swimming pool with blue water, surrounded by lounge chairs and a waterfall feature.
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.
A circular wooden structure with illuminated edges in a garden setting.

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.
HK$1,760
HK$2,014 total
includes taxes & fees
11 Oct - 12 Oct
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 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.

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.
HK$1,335
HK$1,815 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 house with a brick exterior, white exterior walls, and a front porch with white 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.

5. Chatham Seafarer Inn

Chatham Seafarer Inn
Chatham
  • Splash into serenity at the seasonal outdoor pool, where relaxation flows from morning until evening.
HK$1,827
HK$2,091 total
includes taxes & fees
14 Oct - 15 Oct
Chatham Seafarer Inn
A pool area with lounge chairs and a fire pit, surrounded by stone walls and potted plants.
A sunlit room with a view of the sea, featuring a sofa, a round table, and a chair.
A dining area with tables set for two, overlooking a body of water with a sailboat.
A wooden deck with wicker furniture, a table with a vase of flowers, 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.
HK$3,176
HK$3,889 total
includes taxes & fees
18 Oct - 19 Oct
Wequassett Resort and Golf Club
A swimming pool with lounge chairs and a building in the background.
A blue door labeled "Office" with a small window and a mailbox.
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.

7. Handkerchief Shoals Inn

Handkerchief Shoals Inn
South Harwich
HK$1,398
HK$1,601 total
includes taxes & fees
11 Oct - 12 Oct
Handkerchief Shoals Inn
A swimming pool with lounge chairs and umbrellas, surrounded by a fenced area with a building in the background.
A building with a flag, a sign, and a pathway lined with flowers.
A spacious living room with a large abstract painting, two chandeliers, and a coffee machine.
A dining area with a Monopoly board game, patterned chairs, and a large map on the wall.

8. Brewster Green Resort

Brewster Green Resort
Brewster
  • Splash into four poolside paradises with hot tub bliss at this serene Cape Cod hideaway.
HK$2,253
HK$2,579 total
includes taxes & fees
13 Oct - 14 Oct
Brewster Green Resort
A swimming pool with a metal ladder, surrounded by colorful plastic chairs, a red umbrella, and a building with a wooden exterior.
A hotel room with a large bed, teal walls, and a wooden headboard. There are two bedside tables with lamps and small plants.
A modern bathroom with a glass-enclosed shower, a white sink, and a towel rack with folded towels.
A kitchen with a brick stove, a white countertop, and a sign labeled "POOL TOWELS".

9. 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.
HK$1,099
HK$1,257 total
includes taxes & fees
12 Oct - 13 Oct
Olde Tavern Motel And Inn
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.

10. 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.
HK$1,020
HK$1,168 total
includes taxes & fees
12 Oct - 13 Oct
Skaket Beach Motel
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

10/10 Excellent
"Front desk fellow was super helpful. Quality breakfast for on the go. Room was clean and comfortable. Maybe the plywood on the patio could have been painted to make it feel like less a of a sketchy patch job"
Kenneth 2-night trip
Posted less than an hour ago
Hyannis Travel Inn
Bayside Resort Hotel

Bayside Resort Hotel

10/10 Excellent
"So glad we chose this hotel over so many other choices. The room was clean and updated. The staff were so friendly and helpfull. What a great view of the bay and I loved the sandy beach with comfy chairs and the firepits. So nice to relax and enjoy a cocktail fireside."
Jan 2-night trip
Posted 2 hours ago
Bayside Resort Hotel
Red Jacket Beach Resort

Red Jacket Beach Resort

10/10 Excellent
"Beautiful river views. Staff were very nice and helpful."
Frances 2-night trip
Posted 4 hours ago
Red Jacket Beach Resort
Cape Sands Inn

Cape Sands Inn

8/10 Good
"Recommended. Good , clean place at a reasonable price."
Dalton 1-night trip
Posted 5 hours ago
Cape Sands Inn
Chatham Wayside Inn

Chatham Wayside Inn

10/10 Excellent
"Great 3 night stay at The Chatham Wayside. Right in the heart of the town on Main Street. Didn’t need a car for restaurants. Very impressed with the area , so clean. Highly recommend this Hotel"
David 3-night trip
Posted 3 days ago
Chatham Wayside Inn
Chatham Seafarer Inn

Chatham Seafarer Inn

8/10 Good
"N/A"
Roland 1-night trip
Posted 4 days ago
Chatham Seafarer 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?
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.

Explore a world of travel with Expedia