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

Search Hotels with Pool in Chatham

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Check availability on Chatham Hotels with Pool

Tonight
6 Oct - 7 Oct
Tomorrow
7 Oct - 8 Oct
This weekend
9 Oct - 11 Oct
Next weekend
16 Oct - 18 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 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.

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.
฿13,169
฿15,072 total
includes taxes & fees
3 Nov - 4 Nov
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.
A sandy beach path with a wooden fence leading to the ocean, under a partly cloudy sky.

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.
฿6,032
฿8,369 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 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 holiday bliss at this Cape Cod retreat with outdoor pool and soothing hot tub.
฿8,105
฿9,276 total
includes taxes & fees
12 Oct - 13 Oct
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.
฿5,391
฿7,399 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 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.

5. Chatham Seafarer Inn

Chatham Seafarer Inn
Chatham
  • Splash into serenity at the seasonal outdoor pool, where relaxation flows from morning until evening.
฿6,512
฿7,453 total
includes taxes & fees
7 Oct - 8 Oct
Chatham Seafarer Inn
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.
฿12,610
฿15,443 total
includes taxes & fees
26 Oct - 27 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 sign for Handkerchief Shoals Inn with a well-maintained garden in the foreground.
A bedroom with a bed, a table, two chairs, a lamp, and a window with curtains.

7. Handkerchief Shoals Inn

Handkerchief Shoals Inn
South Harwich
฿4,501
฿5,152 total
includes taxes & fees
7 Oct - 8 Oct
Handkerchief Shoals Inn
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 kitchen with a brick stove, a white countertop, and a sign labeled "POOL TOWELS".
A modern bathroom with a glass-enclosed shower, a white sink, and a towel rack with folded towels.

8. 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.
฿3,334
฿3,816 total
includes taxes & fees
7 Oct - 8 Oct
Olde Tavern Motel And 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.

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.
฿4,446
฿5,088 total
includes taxes & fees
7 Oct - 8 Oct
Eagle Wing Inn - Cape Cod
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 golf course with sand bunkers, trees, and a clear blue sky.

10. 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.
฿4,269
฿6,428 total
includes taxes & fees
1 Nov - 2 Nov
The Villages at Ocean Edge
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

Uncommoner Hotel by Reverie Boutique Collection

Uncommoner Hotel by Reverie Boutique Collection

8/10 Good
"You guys need more of your guys need more options for a breakfast and dinner"
Joaquim 1-night trip
Posted 2 hours ago
Uncommoner Hotel by Reverie Boutique Collection
Cape Sands Inn

Cape Sands Inn

8/10 Good
"Comfortable room. Great view. The adjoining room door did not lock."
Delene 2-night trip
Posted 12 hours ago
Cape Sands Inn
Holiday Hill Inn & Suites

Holiday Hill Inn & Suites

10/10 Excellent
"The staff was great and the kids loved the amenities"
Joshua 2-night trip
Posted 15 hours ago
Holiday Hill Inn & Suites
Red Jacket Beach Resort

Red Jacket Beach Resort

8/10 Good
"We enjoy our stay. Staff was friendly, plenty of parking- the beach with chairs, lounges and games was easily accessible. The pool area was very nice."
Marci 2-night trip
Posted 1 day ago
Red Jacket Beach Resort
Riviera Beach Resort

Riviera Beach Resort

10/10 Excellent
"Great property and excellent location!"
Brian 2-night trip
Posted 2 days ago
Riviera Beach Resort
Hyannis Travel Inn

Hyannis Travel Inn

10/10 Excellent
"The staff were friendly and helpful. Great location. I would definitely stay again!"
Tracy 3-night trip
Posted 3 days ago
Hyannis Travel Inn
Greyfinch Chatham Inn

Greyfinch Chatham Inn

10/10 Excellent
"Perfect location. Straight up honesty, it’s not a resort or a newly appointed hotel, but the location is perfect for walking in to town and the rooms are clean and quiet. Compared to other Cape hotels, this is unbeatable for price, quality and location."
Jacob 2-night trip
Posted 4 days ago
Greyfinch Chatham Inn
Chatham Seafarer Inn

Chatham Seafarer Inn

8/10 Good
"Our room was beautiful and very clean! A little odd there was not any staff on site outside the hours of 3 pm - 8 pm but we do not stay at many small hotels so maybe this is normal. They did give us a phone number to call."
Kimberly 2-night trip
Posted 6 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.

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