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 10 - Oct 11
Tomorrow
Oct 11 - Oct 12
Next weekend
Oct 16 - Oct 18
In two weeks
Oct 23 - Oct 25

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 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.

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 1 - Nov 2
Total with taxes and fees
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 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.

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 pathway leading to a beach with boats in the background and a building with a tower.
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.

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.
$391 nightly
$448 total
Nov 3 - Nov 4
Total with taxes and fees
Chatham Bars Inn
A swimming pool with clear blue water, surrounded by blue and white lounge chairs.
A white desk with a woven hat, a vase with white flowers, and two glasses of white wine.
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.

4. Chatham Seafarer Inn

Chatham Seafarer Inn
Chatham
  • Splash into serenity at the seasonal outdoor pool, where relaxation flows from morning until evening.
$233 nightly
$267 total
Oct 25 - Oct 26
Total with taxes and fees
Chatham Seafarer Inn
A swimming pool with blue water, surrounded by lounge chairs and a waterfall feature.
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 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 vacation bliss at this Cape Cod retreat with outdoor pool and soothing hot tub.
$222 nightly
$254 total
Oct 13 - Oct 14
Total with taxes and fees
Pleasant Bay Village Resort
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.
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.

6. 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.
$153 nightly
$175 total
Nov 10 - Nov 11
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 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 hotel room with a bed, a bench, a desk, a microwave, and a television.

7. 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 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.

8. 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.
$108 nightly
$124 total
Oct 12 - Oct 13
Total with taxes and fees
Skaket Beach 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 modern bathroom with a glass-enclosed shower, a white sink, and a towel rack with folded towels.

9. 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.
$134 nightly
$153 total
Oct 12 - Oct 13
Total with taxes and fees
Olde Tavern Motel And 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 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.

10. 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.
$447 nightly
$512 total
Oct 19 - Oct 20
Total with taxes and fees
Wequassett Resort and Golf Club
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

Red Jacket Beach Resort

Red Jacket Beach Resort

10/10 Excellent
"Beautiful river views. Staff were very nice and helpful."
Frances 2-night trip
Posted 1 hour ago
Red Jacket Beach Resort
Cape Sands Inn

Cape Sands Inn

8/10 Good
"Recommended. Good , clean place at a reasonable price."
Dalton 1-night trip
Posted 1 hour ago
Cape Sands Inn
Hyannis Travel Inn

Hyannis Travel Inn

10/10 Excellent
"Location was fantastic! It’s centrally located and walking distance to many restaurants and taverns in Hyannis. Everyone at the front desk was friendly. Room was spacious. Breakfast was adequate."
Crystal 1-night trip
Posted 2 days ago
Hyannis Travel Inn
Holiday Inn Express Hyannis Cape Cod by IHG

Holiday Inn Express Hyannis Cape Cod by IHG

8/10 Good
"Hotel was great, room was tiny, but clean and beds were comfortable. Breakfast was good."
Cheri 2-night trip
Posted 2 days ago
Holiday Inn Express Hyannis Cape Cod by IHG
Chatham Wayside Inn

Chatham Wayside Inn

10/10 Excellent
"Great 3 night stay at The Chatham Wayside. Right in the heart of the town on Main Street. Didn’t need a car for restaurants. Very impressed with the area , so clean. Highly recommend this Hotel"
David 3-night trip
Posted 3 days ago
Chatham Wayside Inn
Chatham Seafarer Inn

Chatham Seafarer Inn

8/10 Good
"N/A"
Roland 1-night trip
Posted 4 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 $72 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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