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

Check availability on Chatham Hotels with a Pool

Tonight
Oct 20 - Oct 21
Tomorrow
Oct 21 - Oct 22
This weekend
Oct 23 - Oct 25
Next weekend
Oct 30 - Nov 1

Our top choices for Chatham hotels with a pool

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.

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.
$217 nightly
$248 total
Nov 3 - Nov 4
Total with taxes and fees
Chatham Wayside 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 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.

2. 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.
$387 nightly
$443 total
Nov 12 - Nov 13
Total with taxes and fees
Chatham Bars Inn
Four sun loungers aligned along a poolside with a tiled floor.
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.
A white house with a grey roof, surrounded by a well-maintained lawn and flowering bushes.

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.
$202 nightly
$231 total
Nov 3 - Nov 4
Total with taxes and fees
Greyfinch Chatham Inn
A swimming pool with blue water, surrounded by lounge chairs and a waterfall feature.
A circular wooden structure with illuminated edges in a garden setting.
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 vacation bliss at this Cape Cod retreat with outdoor pool and soothing hot tub.
$217 nightly
$249 total
Oct 22 - Oct 23
Total with taxes and fees
Pleasant Bay Village Resort
A swimming pool with clear blue water, surrounded by blue and white lounge chairs.
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.
A beach with a fallen tree, clear blue water, and a forested shoreline.

5. Chatham Seafarer Inn

Chatham Seafarer Inn
Chatham
  • Splash into serenity at the seasonal outdoor pool, where relaxation flows from morning until evening.
$259 nightly
$296 total
Oct 21 - Oct 22
Total with taxes and fees
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 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.

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.
$435 nightly
$498 total
Nov 8 - Nov 9
Total with taxes and fees
Wequassett Resort and Golf Club
A swimming pool with a fenced area, lounge chairs, and a building in the background.
A hotel room with two beds, a desk with a television, a red chair, and a window with green curtains.
A bathroom with a toilet, sink, and shower.
A brick building with a white picket fence, a lawn, and a sign for Skaket Beach Motel.

7. Skaket Beach Motel

Skaket Beach Motel
Orleans
  • Dive into relaxation at this coastal motel's seasonal outdoor pool, just steps from beautiful Skaket Beach and sunset views.
$113 nightly
$129 total
Nov 11 - Nov 12
Total with taxes and fees
Skaket Beach Motel
A clear swimming pool with blue lounge chairs and a blue umbrella.
Three children playing in shallow water on a beach.
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.

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.
$160 nightly
$183 total
Nov 8 - Nov 9
Total with taxes and fees
The Villages at Ocean Edge
A swimming pool with lounge chairs and a covered seating area.
A two-story house with a front porch, a mailbox, and a well-maintained garden.
A hotel room with a bed, a bench, a desk, a microwave, and a television.
A covered porch with white Adirondack chairs, a trash can, and a door marked with the number 9.

9. 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.
$204 nightly
$234 total
Oct 26 - Oct 27
Total with taxes and fees
Pelham on Earle
A clear blue swimming pool with a metal ladder, surrounded by lounge chairs and an American flag.
A hotel room with a bed, two nightstands, a chair, a fireplace, and wall art.
A room with nautical-themed decor, including a map, anchor-patterned rug, and a view of the sea through the window.
A Beach Breeze Inn sign with a lighthouse graphic, a vacancy sign, and a building with a brick flower bed in front.

10. A Beach Breeze Inn

A Beach Breeze Inn
West Harwich
  • Tranquil outdoor pool creates a shaded sanctuary amid Cape Cod attractions and ocean breezes.
$129 nightly
$148 total
Oct 21 - Oct 22
Total with taxes and fees
A Beach Breeze Inn
View all properties

Choose what matters most at hotels with a pool in Chatham

Breakfast included
4 stars
Hot tub
5 stars
Spa

Top Chatham Hotel Reviews

Hyannis Travel Inn

Hyannis Travel Inn

10/10 Excellent
"Great stay. Fantastic location for harbour and Hy-line and eating establishments. Accommodation was excellent and super value for money. The staff bent over backwards to help and support. I wish we’d stayed here longer and bypassed Rhode Island!"
Lindsey 3-night trip
Posted 7 hours ago
Hyannis Travel Inn
The Villages at Ocean Edge

The Villages at Ocean Edge

10/10 Excellent
"Great!"
Bradly 3-night trip
Posted 14 hours ago
The Villages at Ocean Edge
Hyannis Harbor Hotel

Hyannis Harbor Hotel

10/10 Excellent
"Visited in October for one night. Great location across from the ferry. Staff was very professional and friendly."
Jeanne 1-night trip
Posted 1 day ago
Hyannis Harbor Hotel
Cape Sands Inn

Cape Sands Inn

10/10 Excellent
"We enjoyed our stay. The sitting area and fore pit were nice. The staff were friendly and we enjoyed the hot tub. The pool area could be updated. Overall, great stay."
Jameliz 3-night trip
Posted 2 days ago
Cape Sands Inn
Margaritaville Resort Cape Cod

Margaritaville Resort Cape Cod

10/10 Excellent
"We stayed here for a wedding we had off property. Had a fun time. I would stay here again. Water park was clean and many lifeguards on duty."
Jean 2-night trip
Posted 2 days ago
Margaritaville Resort Cape Cod
Chatham Bars Inn

Chatham Bars Inn

10/10 Excellent
"Amazing property and staff."
Sylvia 3-night trip
Posted 2 days ago
Chatham Bars Inn
Chatham Wayside Inn

Chatham Wayside Inn

10/10 Excellent
"Great location! Right in the heart of downtown Chatham. The restaurant was a bonus with standard Cape Cod cuisine and very yummy. They also provide bikes if you want to pedal around town. The breakfast included was a bit light, but there's a perfect Cafe next door. We'll definitely stay there again."
Sarah 2-night trip
Posted 3 days ago
Chatham Wayside Inn
Greyfinch Chatham Inn

Greyfinch Chatham Inn

10/10 Excellent
"Clean room. Conveniently located. Friendly staff. Would say there again."
Richard 1-night trip
Posted 4 days ago
Greyfinch Chatham Inn
The Hawthorne

The Hawthorne

8/10 Good
"Beautiful spot with wonderful views of Chatham Bars without the crazy experience of Chatham Bars Inn"
Richard 2-night trip
Posted 2 weeks ago
The Hawthorne

Frequently asked questions

What are the best hotels in Chatham with outdoor pools?
Pleasant Bay Village Resort is a charming 3-star hotel that offers an inviting outdoor pool, superb for families looking to unwind and enjoy the sun. Guests have raved about the comfortable and clean rooms, as well as the friendly and attentive staff, achieving an outstanding score of 9.6. The beautifully landscaped grounds add to the resort's appeal, making it a serene getaway.For those seeking a more luxurious experience, Chatham Bars Inn stands out as a premier 5-star hotel. This hotel not only features a stunning outdoor pool but also offers a private beach, an array of top amenities, and exceptional service. With a traveller rating of 9.2, visitors appreciate the exquisite food, beautiful location, and the staff's willingness to go above and beyond to enhance their stay.Chatham Wayside Inn, a delightful 4-star hotel, is another fantastic option boasting an outdoor pool. Guests love the charming and clean rooms, along with the friendly staff who are always ready to assist. With a review rating of 9.2, the included complimentary breakfast adds great value for families looking to start their day right before exploring the local attractions.Each of these hotels provides unique features and a warm atmosphere, making them excellent choices for families seeking a memorable stay in Chatham.
How much does a hotel with outdoor pool in Chatham cost?
Enjoy staying in a hotel in Chatham with an outdoor pool. You can find a great deal from $129 on Expedia. If you're leaning toward a little luxury, prices can rise, and may vary depending on the location, season, and hotel amenities. Be sure to book in advance to enjoy more options and potentially better rates, especially if you're planning a trip during weekends or around public holidays.
What are some of the best Chatham hotels with outdoor pools and scenic views?
Chatham Bars Inn is a stunning 5-star retreat that offers an unforgettable experience for travellers seeking outdoor pools combined with breathtaking views. With a remarkable review rating of 9.2, guests rave about the excellent service and the beautiful location, making it an ideal choice for families and adventure-seekers alike.This exquisite hotel boasts a gorgeous outdoor pool that overlooks the serene landscape, allowing you to soak in the sun while enjoying the picturesque surroundings. Families can take advantage of the private beach access, great for a day of fun in the sand, or enjoy a game of tennis on-site. The spacious rooms feature premium bedding and designer toiletries, ensuring a comfortable and luxurious stay.Moreover, the inn's top amenities extend to a relaxing massage service, making it easy for parents to unwind while the kids splash around in the pool. Dining options are also highly praised, with guests noting the exceptional quality of the food available, enhancing the overall experience at this remarkable destination.
Is it cheaper to book flights and a Chatham hotel with a pool as a package?
Booking a hotel and flight package on Expedia can be cheaper than booking flights and hotels separately. Bundling can lead to significant savings, especially for international travel or when booking well in advance. However, savings vary depending on factors like destination, travel dates and availability, so it's wise to compare options. With access to over 300,000 hotels worldwide, Expedia makes it easy to build the perfect vacation package.
Can I cancel my hotel reservation on Expedia?
Expedia has plenty of refundable hotels. In many cases, you need to cancel your booking 24-48 hours ahead of your arrival date. Remember to check your booking confirmation for the exact cancellation policy. For maximum flexibility, use Expedia's "Fully refundable property" filter during your search to find the right hotel in Chatham for you.

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