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

Chatham Hotels with Swimming Pool

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Check availability on Chatham Hotels with Swimming Pools

Tonight
5 Oct - 6 Oct
Tomorrow
6 Oct - 7 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 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.

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.
RM1,597
RM1,828 total
includes taxes & fees
3 Nov - 4 Nov
Chatham Bars Inn
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.

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.
RM732
RM1,015 total
includes taxes & fees
29 Oct - 30 Oct
Chatham Wayside Inn
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.

3. 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.
RM656
RM901 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.
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.
A beach with a fallen tree, clear blue water, and a forested shoreline.

4. Chatham Seafarer Inn

Chatham Seafarer Inn
Chatham
  • Splash into serenity at the seasonal outdoor pool, where relaxation flows from morning until evening.
RM793
RM907 total
includes taxes & fees
7 Oct - 8 Oct
Chatham Seafarer 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 circular wooden structure with illuminated edges in a garden setting.

5. 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.
RM986
RM1,129 total
includes taxes & fees
6 Oct - 7 Oct
Pleasant Bay Village Resort
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 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.
RM1,653
RM2,024 total
includes taxes & fees
18 Oct - 19 Oct
Wequassett Resort and Golf Club
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 cozy living room with a fireplace, a Christmas tree, and festive decorations.
A large, two-story house with a covered patio area, outdoor seating, and a stone waterfall feature.

7. Winstead Inn

Winstead Inn
Harwich
  • Heated poolside oasis beckons with lush gardens, private beach access, and free shuttle service.
RM1,072
RM1,227 total
includes taxes & fees
6 Oct - 7 Oct
Winstead Inn
A swimming pool with lounge chairs and a building in the background.
A blue door labeled "Office" with a small window and a mailbox.
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.

8. Handkerchief Shoals Inn

Handkerchief Shoals Inn
South Harwich
RM546
RM625 total
includes taxes & fees
6 Oct - 7 Oct
Handkerchief Shoals Inn
An indoor swimming pool with wooden beams on the ceiling, clear windows, and a 'NO DIVING' sign.
A building with a flag, a sign, and a pathway lined with flowers.
A spacious living room with a large abstract painting, two chandeliers, and a coffee machine.
A dining area with a Monopoly board game, patterned chairs, and a large map on the wall.

9. Brewster Green Resort

Brewster Green Resort
Brewster
  • Splash into four poolside paradises with hot tub bliss at this serene Cape Cod hideaway.
RM805
RM921 total
includes taxes & fees
19 Oct - 20 Oct
Brewster Green Resort
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 modern bathroom with a glass-enclosed shower, a white sink, and a towel rack with folded towels.
A kitchen with a brick stove, a white countertop, and a sign labeled "POOL TOWELS".

10. 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.
RM404
RM463 total
includes taxes & fees
6 Oct - 7 Oct
Olde Tavern Motel And 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

Holiday Hill Inn & Suites

Holiday Hill Inn & Suites

8/10 Good
"On the down side 1) strong odor of cleaner/ disinfectant 2) Dated decor 3) limited cable access On the plus side 1) sign in was a breeze 2) free internet 3) room was clean and well stocked 4) Quiet"
Edward 1-night trip
Posted 1 hour ago
Holiday Hill Inn & Suites
Cape Sands Inn

Cape Sands Inn

8/10 Good
"At this price point, Cape Sands Inn is excellent value. We stayed in room 212, which had a small, but useful balcony that looked out over the garden, barbeque area, and the creek. The room had 2 comfortable queen beds, a large fridge, a coffee maker, and everything worked. I had to ask reception to turn up the hot water, which they did - straight away. I had to learn that it was necessary to run the bath tub tap until the water got hot to get hot water from the sink tap. Once I understood what I had to do, it was easy. The cleaners did a good job, every 2 days. The reception staff were nice and very helpful. It was a very good experience :)"
Simeon 7-night trip
Posted 1 hour ago
Cape Sands Inn
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 3 hours ago
Red Jacket Beach Resort
Bayside Resort Hotel

Bayside Resort Hotel

10/10 Excellent
"Loved my stay here. Outdoor pool was open great hours, considering it was late in the season. Indoor pool and hot tub were clean, also with great hours. Breakfast had a much larger selection than usual continental breakfast menu. Loved the onsite bar, and the outdoor firepit area right on the edge of the saltmarsh. Rooms were clean, with a comfortable bed. Staff were very helpful and kind. I'm looking forward to staying again sometime soon!"
Laura 2-night trip
Posted 17 hours ago
Bayside Resort Hotel
Uncommoner Hotel by Reverie Boutique Collection

Uncommoner Hotel by Reverie Boutique Collection

10/10 Excellent
"Loved the hotel and can’t speak more highly of the staff. Only disappointment was the restaurant and grounds were closed our second night due to a private function. Our first night was rained out so giving up our last night to a private party was unfortunate. Maybe in the future they will open some part of the property for hotel guests to enjoy while accommodating a private party."
Melissa 2-night trip
Posted 19 hours ago
Uncommoner Hotel by Reverie Boutique Collection
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 2 days ago
Hyannis Travel Inn
Margaritaville Resort Cape Cod

Margaritaville Resort Cape Cod

8/10 Good
"It was a nice place to stay."
Norine 2-night trip
Posted 2 days ago
Margaritaville Resort Cape Cod
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 3 days ago
Greyfinch Chatham 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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