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

Our top choices for Chatham hotels with a pool

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.
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.
NT$5,537
NT$7,753 total
includes taxes & fees
Nov 2 - Nov 3
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.
A series of tents with beds and seating areas, surrounded by a garden with various plants and a wooden deck.
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.

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.
NT$12,588
NT$14,407 total
includes taxes & fees
Nov 5 - Nov 6
Chatham Bars Inn
A swimming pool with blue water, surrounded by lounge chairs and a waterfall feature.
A dining area with a glass table, chairs, and a vase with flowers.
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.

3. 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.
NT$7,861
NT$8,996 total
includes taxes & fees
Oct 25 - Oct 26
Pleasant Bay Village Resort
Four sun loungers aligned along a poolside with a tiled floor.
A white house with a grey roof, surrounded by a well-maintained lawn and flowering bushes.
A modern kitchen with white cabinetry, a wooden island with two barstools, and a decorative wall art piece.
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.
NT$5,516
NT$7,501 total
includes taxes & fees
Nov 1 - Nov 2
Greyfinch Chatham Inn
A swimming pool with clear blue water, surrounded by blue and white lounge chairs.
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.
A white desk with a woven hat, a vase with white flowers, and two glasses of white wine.

5. Chatham Seafarer Inn

Chatham Seafarer Inn
Chatham
  • Splash into serenity at the seasonal outdoor pool, where relaxation flows from morning until evening.
NT$7,551
NT$8,642 total
includes taxes & fees
Oct 25 - Oct 26
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 resort with a swimming pool, beach area, and a large building with a dome structure.

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.
NT$11,579
NT$14,180 total
includes taxes & fees
Nov 8 - Nov 9
Wequassett Resort and Golf Club
A swimming pool with lounge chairs and a building in the background.
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.
A blue door labeled "Office" with a small window and a mailbox.

7. Handkerchief Shoals Inn

Handkerchief Shoals Inn
South Harwich
NT$5,778
NT$6,613 total
includes taxes & fees
Nov 8 - Nov 9
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 kitchen with a white island, a fireplace, and a surfboard decoration.
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.
NT$5,859
NT$6,705 total
includes taxes & fees
Oct 24 - Oct 25
Eagle Wing Inn - Cape Cod
A swimming pool with lounge chairs and umbrellas, surrounded by greenery and a building.
A hotel reception area with a blue wall, a reception desk, a large window, and a welcome mat.
A garden area with a welcome sign, outdoor seating, and a blue umbrella.
A bathroom with a shower curtain, a bathtub, and a tiled wall with a marble-like pattern.

9. 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.
NT$3,587
NT$4,105 total
includes taxes & fees
Oct 26 - Oct 27
Rodeway Inn Orleans - Cape Cod
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 bathroom with a toilet, sink, and shower.
A covered patio with a round table and four chairs.

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.
NT$4,231
NT$4,843 total
includes taxes & fees
Oct 25 - Oct 26
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

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 11 hours ago
Hyannis Travel Inn
Bayside Resort Hotel

Bayside Resort Hotel

8/10 Good
"Staff very friendly"
suzanne 3-night trip
Posted 16 hours ago
Bayside Resort Hotel
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
The Hawthorne

The Hawthorne

8/10 Good
"Beautiful spot with wonderful views of Chatham Bars without the crazy experience of Chatham Bars Inn"
Richard 2-night trip
Posted 3 weeks ago
The Hawthorne

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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