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

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Check availability on Chatham Hotels with a Pool

Tonight
Oct 17 - Oct 18
Tomorrow
Oct 18 - Oct 19
Next weekend
Oct 23 - Oct 25
In two weeks
Oct 30 - Nov 1

Our top choices for Chatham hotels with a pool

A swimming pool with lounge chairs and a white fence.
A garden with a pergola structure, a pathway, and a seating area.
A restaurant with long communal tables and booths, large windows, and a view of buildings outside.
A sandy beach path with a wooden fence leading to the ocean, under a partly cloudy sky.

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.
$208 nightly
$238 total
Nov 2 - Nov 3
Total with taxes and fees
Chatham Wayside Inn
Four sun loungers aligned along a poolside with a tiled floor.
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.
A white house with a grey roof, surrounded by a well-maintained lawn and flowering bushes.

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.
$202 nightly
$231 total
Nov 1 - Nov 2
Total with taxes and fees
Greyfinch Chatham Inn
A resort pool with multiple sun loungers and umbrellas, surrounded by beach views and boats.
A series of tents with beds and seating areas, surrounded by a garden with various plants and a wooden deck.
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.

3. 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
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.

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 25 - Oct 26
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 white desk with a woven hat, a vase with white flowers, and two glasses of white wine.

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 19 - Oct 20
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 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 dining area with tables set for two, overlooking a body of water with a sailboat.

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.
$395 nightly
$452 total
Nov 11 - Nov 12
Total with taxes and fees
Wequassett Resort and Golf Club
A clear swimming pool with blue lounge chairs and a blue umbrella.
A restaurant with brick arches, wooden tables, and chairs. There is a bar area with bottles and a television screen.
Three children playing in shallow water on a beach.
A golf course with sand bunkers, trees, and a clear blue sky.

7. 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.
$148 nightly
$169 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 modern interior with a wooden floor, a blue and white patterned wall, a large painting, and a bar area with a blue marble backsplash.
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.
$204 nightly
$234 total
Oct 26 - Oct 27
Total with taxes and fees
Pelham on Earle
A swimming pool with a fenced area, lounge chairs, and a building in the background.
A brick building with a white picket fence, a lawn, and a sign for Skaket Beach Motel.
A covered patio with a round table and four chairs.
A hotel room with two beds, a desk with a television, a red chair, and a window with green curtains.

9. 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
Oct 28 - Oct 29
Total with taxes and fees
Skaket Beach Motel
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 18 - Oct 19
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

Chatham Wayside Inn

Chatham Wayside Inn

8/10 Good
"One of the service staff in the restaurant was very condescending to my sister in-law. ( Ian ? ) Otherwise it was a great stay. Housekeeping staff was great. Thank You"
Robert 4-night trip
Posted 7 hours ago
Chatham Wayside Inn
Margaritaville Resort Cape Cod

Margaritaville Resort Cape Cod

8/10 Good
"Didn’t like the room next to the pool, especially on the first floor. No privacy. No fresh air. No sunlight. Had a damp feeling in the room the whole week. But we did like Nate the bar tender!"
James 4-night trip
Posted 13 hours ago
Margaritaville Resort Cape Cod
Greyfinch Chatham Inn

Greyfinch Chatham Inn

10/10 Excellent
"Clean room. Conveniently located. Friendly staff. Would say there again."
Richard 1-night trip
Posted 13 hours ago
Greyfinch Chatham Inn
Uncommoner Hotel by Reverie Boutique Collection

Uncommoner Hotel by Reverie Boutique Collection

10/10 Excellent
"Beautiful hotel. I’d stay again"
Ediley 3-night trip
Posted 1 day ago
Uncommoner Hotel by Reverie Boutique Collection
Chatham Bars Inn

Chatham Bars Inn

10/10 Excellent
"We liked everything. The service was amazing and the resort is beautiful."
Linda 3-night trip
Posted 4 days ago
Chatham Bars Inn
Chatham Seafarer Inn

Chatham Seafarer Inn

8/10 Good
"Office was only open limited hours"
James 2-night trip
Posted 5 days ago
Chatham Seafarer Inn

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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