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

Find Hotels with a Pool in Chatham, MA

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Check availability on Chatham Hotels with a Pool

Tonight
15 Oct - 16 Oct
Tomorrow
16 Oct - 17 Oct
This weekend
16 Oct - 18 Oct
Next weekend
23 Oct - 25 Oct

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.
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.

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.
AED 658
AED 913 total
includes taxes & fees
1 Nov - 2 Nov
Chatham Wayside Inn
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.
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.
AED 1,296
AED 1,483 total
includes taxes & fees
12 Nov - 13 Nov
Chatham Bars 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 beach with a fallen tree, clear blue water, and a forested shoreline.
A white desk with a woven hat, a vase with white flowers, and two glasses of white wine.

3. Chatham Seafarer Inn

Chatham Seafarer Inn
Chatham
  • Splash into serenity at the seasonal outdoor pool, where relaxation flows from morning until evening.
AED 855
AED 979 total
includes taxes & fees
19 Oct - 20 Oct
Chatham Seafarer Inn
Four sun loungers aligned along a poolside with a tiled floor.
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.
A modern bathroom with a double sink vanity, a large mirror, and a glass-enclosed shower area.

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.
AED 625
AED 850 total
includes taxes & fees
1 Nov - 2 Nov
Greyfinch Chatham 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 covered porch with a lattice design, a stone pathway, and a view of a garden.
A circular wooden structure with illuminated edges in a garden setting.

5. Pleasant Bay Village Resort

Pleasant Bay Village Resort
Chatham
  • Splash into vacation bliss at this Cape Cod retreat with outdoor pool and soothing hot tub.
AED 781
AED 893 total
includes taxes & fees
18 Oct - 19 Oct
Pleasant Bay Village Resort
A pool area with lounge chairs and a fire pit, surrounded by stone walls and potted plants.
A wooden deck with wicker furniture, a table with a vase of flowers, and a view of the sea.
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.
AED 1,430
AED 1,751 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 sign for Handkerchief Shoals Inn with a well-maintained garden in the foreground.
An outdoor patio with round tables and chairs, picnic tables, and umbrellas.

7. Handkerchief Shoals Inn

Handkerchief Shoals Inn
South Harwich
AED 655
AED 749 total
includes taxes & fees
18 Oct - 19 Oct
Handkerchief Shoals Inn
A spa area with a hot tub and a swimming pool, surrounded by large windows and potted plants.
A two-story house with a porch, surrounded by lush greenery and flowering bushes.
A spacious living room with a wooden ceiling, large windows, a dining area with a table set for four, and a sofa with cushions.
A dining area with a wooden table, chairs, and a vase of flowers. There is a kitchen with a sink and a window above it.

8. Whalewalk Inn and Spa

Whalewalk Inn and Spa
Eastham
  • Escape to the indoor pool sanctuary at this Cape Cod haven near natural wonders.
AED 789
AED 903 total
includes taxes & fees
19 Oct - 20 Oct
Whalewalk Inn and Spa
A swimming pool with a fenced area, lounge chairs, and a building in the background.
A brick building with a white picket fence, a lawn, and a sign for Skaket Beach Motel.
A covered patio with a round table and four chairs.
A hotel room with two beds, a desk with a television, a red chair, and a window with green curtains.

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.
AED 430
AED 492 total
includes taxes & fees
18 Oct - 19 Oct
Skaket Beach Motel
A large swimming pool with a fountain, surrounded by lounge chairs and umbrellas, set against a stone building with multiple windows and a balcony.
A two-story house with a well-lit front porch, a staircase leading to the entrance, and a garden with various plants and flowers.
A corner building with a curved roof, large windows, and a well-maintained garden with various plants and flowers.
A large, two-story house with a covered patio area, outdoor seating, and a stone waterfall feature.

10. Winstead Inn

Winstead Inn
Harwich
  • Heated poolside oasis beckons with lush gardens, private beach access, and free shuttle service.
AED 964
AED 1,103 total
includes taxes & fees
19 Oct - 20 Oct
Winstead Inn
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 Harbor Hotel

Hyannis Harbor Hotel

8/10 Good
"No amenities"
Ray 1-night trip
Posted 18 hours ago
Hyannis Harbor Hotel
Red Jacket Beach Resort

Red Jacket Beach Resort

10/10 Excellent
"The place was clean. The smell from the sea weed cleanup was potent."
Lewis 3-night trip
Posted 2 days ago
Red Jacket Beach Resort
Chatham Wayside Inn

Chatham Wayside Inn

10/10 Excellent
"The room was spacious and airy, cl ean and well maintained."
Lenette 3-night trip
Posted 2 days ago
Chatham Wayside Inn
Chatham Bars Inn

Chatham Bars Inn

10/10 Excellent
"We liked everything. The service was amazing and the resort is beautiful."
Linda 3-night trip
Posted 2 days ago
Chatham Bars Inn
Chatham Seafarer Inn

Chatham Seafarer Inn

8/10 Good
"Office was only open limited hours"
James 2-night trip
Posted 4 days ago
Chatham Seafarer Inn
Greyfinch Chatham Inn

Greyfinch Chatham Inn

10/10 Excellent
"Great stay for the price. Staff wasn’t very helpful"
Sandra 3-night trip
Posted 4 days ago
Greyfinch Chatham Inn

Frequently asked questions

What are some accommodations 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, check out 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 into account the local weather in Chatham is an important factor for planning your visit, especially if you plan to spend your trip poolside. The hottest months are usually August and July with an average temp of 67°F, while the coldest months are February and January with an average of 38°F. Average annual precipitation for Chatham is 54 inches.

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