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 14 - Oct 15
Tomorrow
Oct 15 - Oct 16
This weekend
Oct 16 - Oct 18
Next weekend
Oct 23 - Oct 25

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 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.
A deck with white Adirondack chairs and a small round table, overlooking a beach and ocean.

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.
₩474,008
₩542,502 total
includes taxes & fees
Nov 12 - Nov 13
Chatham Bars 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.

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.
₩239,063
₩331,671 total
includes taxes & fees
Nov 1 - Nov 2
Chatham Wayside 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 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 circular wooden structure with illuminated edges in a garden setting.

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.
₩322,354
₩368,934 total
includes taxes & fees
Oct 19 - Oct 20
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 bedroom with a wooden wardrobe, a white robe hanging on the door, and a bed with a wooden frame.
A modern kitchen with white cabinetry, a wooden island with two barstools, and a decorative wall art piece.

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.
₩227,049
₩308,752 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.
An outdoor patio with white metal chairs and a table, surrounded by blooming pink trees.
A white desk with a woven hat, a vase with white flowers, and two glasses of white wine.
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.
₩310,835
₩355,738 total
includes taxes & fees
Oct 19 - Oct 20
Chatham Seafarer Inn
A pool area with lounge chairs and a fire pit, surrounded by stone walls and potted plants.
A balcony with wicker furniture, a table with a vase and wine glass, 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 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.
₩543,264
₩665,294 total
includes taxes & fees
Oct 19 - Oct 20
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 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
₩237,861
₩272,232 total
includes taxes & fees
Oct 20 - Oct 21
Handkerchief Shoals Inn
A clear swimming pool with blue lounge chairs and a blue umbrella.
Three children playing in shallow water on a beach.
An outdoor patio with tables and chairs, umbrellas, and a view of the ocean.
A restaurant with brick arches, wooden tables, and chairs. There is a bar area with bottles and a television screen.

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 vacation mood.
₩134,787
₩215,780 total
includes taxes & fees
Nov 8 - Nov 9
The Villages at Ocean Edge
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 kitchen with a white island, a fireplace, and a surfboard decoration.

9. 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.
₩173,344
₩198,392 total
includes taxes & fees
Oct 15 - Oct 16
Eagle Wing Inn - Cape Cod
A swimming pool with lounge chairs and a covered seating area.
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.
A modern interior with a wooden floor, a blue and white patterned wall, a large painting, and a bar area with a blue marble backsplash.

10. 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.
₩252,277
₩311,822 total
includes taxes & fees
Oct 29 - Oct 30
Pelham on Earle
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Choose what matters most at hotels with a pool in Chatham

Breakfast included
Hot tub
4 stars
5 stars
Spa

Top Chatham Hotel Reviews

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 10 hours ago
Red Jacket Beach Resort
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 15 hours ago
Chatham Bars Inn
Chatham Seafarer Inn

Chatham Seafarer Inn

8/10 Good
"Office was only open limited hours"
James 2-night trip
Posted 2 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 2 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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