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

Search Hotels with Swimming Pool in Chatham

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Check availability on Chatham Hotels with Swimming Pool

Tonight
7 Sept - 8 Sept
Tomorrow
8 Sept - 9 Sept
This weekend
11 Sept - 13 Sept
Next weekend
18 Sept - 20 Sept

Our top choices for Chatham hotels with a pool

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 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.

1. 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.
₹16,787
₹22,674 total
includes taxes & fees
1 Oct - 2 Oct
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.
An outdoor patio with white metal chairs and a table, surrounded by blooming pink trees.
A house with a brick exterior, white exterior walls, and a front porch with white chairs.

2. Chatham Seafarer Inn

Chatham Seafarer Inn
Chatham
  • Splash into serenity at the seasonal outdoor pool, where relaxation flows from morning until evening.
₹18,338
₹20,987 total
includes taxes & fees
22 Sept - 23 Sept
Chatham Seafarer 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 garden with a pergola structure, a pathway, and a seating area.

3. 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.
₹33,933
₹42,947 total
includes taxes & fees
29 Sept - 30 Sept
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 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 dining area with a glass table, chairs, and a vase with flowers.

4. 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.
₹21,223
₹24,290 total
includes taxes & fees
8 Oct - 9 Oct
Pleasant Bay Village Resort
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.
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.

5. 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.
₹53,012
₹60,672 total
includes taxes & fees
20 Sept - 21 Sept
Chatham Bars Inn
A building with a blue roof, a white steeple, and a flagpole with an American flag.
A paved outdoor area with three Adirondack chairs, a street lamp, and a row of houses in the background.
A cozy room with a wicker sofa, two chairs, a small table, and large windows with a view of trees.

6. The Chatham Motel

The Chatham Motel
Chatham
  • Soak up summer vibes in this Cape Cod retreat with a seasonal outdoor pool, playground, and peaceful garden setting.
₹26,506
₹30,336 total
includes taxes & fees
8 Sept - 9 Sept
The Chatham Motel
A swimming pool with a metal ladder, surrounded by colorful plastic chairs, a red umbrella, and a building with a wooden exterior.
A dining area with round tables and chairs, floral centerpieces, and decorative wall signs.
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".

7. 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.
₹10,489
₹12,005 total
includes taxes & fees
4 Oct - 5 Oct
Olde Tavern Motel And Inn
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 bedroom with a bed, a table, two chairs, a lamp, and a window with curtains.

8. Handkerchief Shoals Inn

Handkerchief Shoals Inn
South Harwich
₹12,629
₹14,455 total
includes taxes & fees
14 Sept - 15 Sept
Handkerchief Shoals Inn
A pool area with lounge chairs, a hot tub, and string lights.
A modern living room with a blue sofa, a coffee table, a large window, and a surfboard decoration.
A backyard with a fire pit, outdoor seating, string lights, and a hammock.
A room with arcade games, a TV, a large window, and a plant.

9. Dennis Port Surf Club (Boutique Hotel)

Dennis Port Surf Club (Boutique Hotel)
Dennis Port
  • Seasonal outdoor pool offers refreshing oceanside swims after coastal adventures.
₹9,288
₹10,630 total
includes taxes & fees
9 Sept - 10 Sept
Dennis Port Surf Club (Boutique Hotel)
A clear swimming pool with blue lounge chairs and a blue umbrella.
A golf course with sand bunkers, trees, and a clear blue sky.
An outdoor patio with tables and chairs, umbrellas, and a view of the ocean.
Three children playing in shallow water on a beach.

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.
₹13,915
₹20,252 total
includes taxes & fees
20 Sept - 21 Sept
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

Hyannis Harbor Hotel

Hyannis Harbor Hotel

8/10 Good
"Clean."
Tucker 3-night trip
Posted less than an hour ago
Hyannis Harbor Hotel
Bayside Resort Hotel

Bayside Resort Hotel

10/10 Excellent
"Great stay, room was clean. All the amenities are great especially the indoor and outdoor pool. Will continue to stay at this property and highly recommend for couples or family staying"
Desiree 2-night trip
Posted 1 hour ago
Bayside Resort Hotel
Margaritaville Resort Cape Cod

Margaritaville Resort Cape Cod

10/10 Excellent
"Clean room, parking Great family trip"
Tatiana 3-night trip
Posted 1 hour ago
Margaritaville Resort Cape Cod
Cape Sands Inn

Cape Sands Inn

10/10 Excellent
"Loved the room , very clean and comfortable"
martin 2-night trip
Posted 5 hours ago
Cape Sands Inn
Holiday Inn Express Hyannis Cape Cod by IHG

Holiday Inn Express Hyannis Cape Cod by IHG

10/10 Excellent
"The room and hotel were very clean! The staff was polite as well. I would definitely stay here again!"
Sara-Rose 1-night trip
Posted 8 hours ago
Holiday Inn Express Hyannis Cape Cod by IHG
Uncommoner Hotel by Reverie Boutique Collection

Uncommoner Hotel by Reverie Boutique Collection

8/10 Good
"3E's of UnCommonor elegant - exquisite - extraordinaire-"
Angel 2-night trip
Posted 22 hours ago
Uncommoner Hotel by Reverie Boutique Collection
Holiday Hill Inn & Suites

Holiday Hill Inn & Suites

10/10 Excellent
"Staff was great - clean amenities"
janine 4-night trip
Posted 1 day ago
Holiday Hill Inn & Suites
Freebird Motor Lodge by Reverie Boutique Collection

Freebird Motor Lodge by Reverie Boutique Collection

10/10 Excellent
"It would be cool to add a gym."
Nikolai 3-night trip
Posted 2 days ago
Freebird Motor Lodge by Reverie Boutique Collection
Chatham Wayside Inn

Chatham Wayside Inn

10/10 Excellent
"Clean room, nice staff, no laundry on site, property could use upgrades."
Claudia 2-night trip
Posted 3 days ago
Chatham Wayside 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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