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 8 - Oct 9
Tomorrow
Oct 9 - Oct 10
This weekend
Oct 9 - Oct 11
Next weekend
Oct 16 - Oct 18

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.
A garden with a pergola structure, a pathway, and a seating area.

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 kitchen with white cabinetry, a wooden island with two barstools, and a decorative wall art piece.
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.
$193 nightly
$220 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 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.

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 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 covered porch with a lattice design, a stone pathway, and a view of a garden.

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.
$196 nightly
$224 total
Oct 13 - Oct 14
Total with taxes and fees
Pleasant Bay Village Resort
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 white desk with a woven hat, a vase with white flowers, and two glasses of white wine.
An outdoor patio with white metal chairs and a table, surrounded by blooming pink trees.

5. 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 22 - Oct 23
Total with taxes and fees
Chatham Seafarer Inn
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 covered porch with white Adirondack chairs, a trash can, and a door marked with the number 9.
A hotel room with a bed, a bench, a desk, a microwave, and a television.

6. 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 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 dining area with tables set for two, overlooking a body of water with a sailboat.

7. 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.
$433 nightly
$496 total
Oct 18 - Oct 19
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 brick building with a white picket fence, a lawn, and a sign for Skaket Beach Motel.
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.
$114 nightly
$131 total
Oct 15 - Oct 16
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.
An outdoor patio with tables and chairs, umbrellas, and a view of the ocean.

9. 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.
$157 nightly
$180 total
Nov 8 - Nov 9
Total with taxes and fees
The Villages at Ocean Edge
A swimming pool with a metal ladder, surrounded by colorful plastic chairs, a red umbrella, and a building with a wooden exterior.
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".
A hotel room with a large bed, teal walls, and a wooden headboard. There are two bedside tables with lamps and small plants.

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.
$140 nightly
$160 total
Oct 12 - Oct 13
Total with taxes and fees
Olde Tavern Motel And 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

8/10 Good
"The hotel is older so the outside is a little weathered but the room was updated and very clean and the staff was so nice. For the price, which was great, I would recommend staying here. It's also a short walk to the holiness ferry terminal which was very convenient."
Pamela 2-night trip
Posted 7 hours ago
Hyannis Travel Inn
Red Jacket Beach Resort

Red Jacket Beach Resort

10/10 Excellent
"Always, the best!"
Elizabeth 2-night trip
Posted 9 hours ago
Red Jacket Beach Resort
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 1 day ago
Chatham Wayside Inn
Hyannis Plaza Hotel

Hyannis Plaza Hotel

10/10 Excellent
"Very happy"
Sharon 1-night trip
Posted 1 day ago
Hyannis Plaza Hotel
Chatham Seafarer Inn

Chatham Seafarer Inn

8/10 Good
"N/A"
Roland 1-night trip
Posted 2 days ago
Chatham Seafarer Inn
Cape Sands Inn

Cape Sands Inn

8/10 Good
"Comfortable room. Great view. The adjoining room door did not lock."
Delene 2-night trip
Posted 3 days ago
Cape Sands 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 $131 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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