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

Hotels with Swimming Pools in Chatham

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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 swimming pool with lounge chairs and a white fence.
A sandy beach path with a wooden fence leading to the ocean, under a partly cloudy sky.
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.

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.
S$318
includes taxes & fees
29 Oct - 30 Oct
Chatham Wayside Inn
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.

2. 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.
S$282
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 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.
An outdoor patio with white metal chairs and a table, surrounded by blooming pink trees.

3. Chatham Seafarer Inn

Chatham Seafarer Inn
Chatham
  • Splash into serenity at the seasonal outdoor pool, where relaxation flows from morning until evening.
S$284
includes taxes & fees
7 Oct - 8 Oct
Chatham Seafarer 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.

4. 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.
S$572
includes taxes & fees
3 Nov - 4 Nov
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 covered porch with a lattice design, a stone pathway, and a view of a garden.
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.
S$329
includes taxes & fees
18 Oct - 19 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 balcony with wicker furniture, a table with a vase and wine glass, and a view of the sea.
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.
S$633
includes taxes & fees
18 Oct - 19 Oct
Wequassett Resort and Golf Club
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 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.

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.
S$145
includes taxes & fees
6 Oct - 7 Oct
Olde Tavern Motel And Inn
A swimming pool with lounge chairs and a covered seating area.
A hotel room with a bed, a bench, a desk, a microwave, and a television.
A two-story house with a front porch, a mailbox, and a well-maintained garden.
A covered porch with white Adirondack chairs, a trash can, and a door marked with the number 9.

8. 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.
S$299
includes taxes & fees
26 Oct - 27 Oct
Pelham on Earle
A swimming pool with lounge chairs and a building in the background.
A bedroom with a bed, a table, two chairs, a lamp, and a window with curtains.
A blue door labeled "Office" with a small window and a mailbox.
An outdoor patio with round tables and chairs, picnic tables, and umbrellas.

9. Handkerchief Shoals Inn

Handkerchief Shoals Inn
South Harwich
S$196
includes taxes & fees
6 Oct - 7 Oct
Handkerchief Shoals Inn
A clear swimming pool with blue lounge chairs and a blue umbrella.
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.
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.
S$244
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

Bayside Resort Hotel

Bayside Resort Hotel

8/10 Good
"Our room was extremely clean and neat. The inside of the hotel in all the areas was very neat and clean. My only concern was that one of the outside lights that lit part of the parking lot was out. It was a bit unnerving to walk to the car in the dark"
rosalina 2-night trip
Posted 1 hour ago
Bayside Resort Hotel
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 5 hours 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 6 hours 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 8 hours ago
Red Jacket Beach Resort
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 23 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
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
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 5 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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