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
Sep 10 - Sep 11
Tomorrow
Sep 11 - Sep 12
This weekend
Sep 11 - Sep 13
Next weekend
Sep 18 - Sep 20

Our top choices for Chatham hotels with a pool

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 white house with a grey roof, surrounded by a well-maintained lawn and flowering bushes.
A modern bathroom with a double sink vanity, a large mirror, and a glass-enclosed shower area.

1. 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.
$210 nightly
$240 total
Oct 1 - Oct 2
Total with taxes and fees
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.
An outdoor patio with white metal chairs and a table, surrounded by blooming pink trees.
A house with a brick exterior, white exterior walls, and a front porch with white chairs.

2. Chatham Seafarer Inn

Chatham Seafarer Inn
Chatham
  • Splash into serenity at the seasonal outdoor pool, where relaxation flows from morning until evening.
$194 nightly
$222 total
Oct 7 - Oct 8
Total with taxes and fees
Chatham Seafarer Inn
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 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.

3. 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.
$397 nightly
$454 total
Sep 27 - Sep 28
Total with taxes and fees
Chatham Wayside 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 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.

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.
$229 nightly
$263 total
Sep 22 - Sep 23
Total with taxes and fees
Pleasant Bay Village Resort
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.
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.

5. 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.
$655 nightly
$749 total
Sep 24 - Sep 25
Total with taxes and fees
Chatham Bars Inn
A building with a blue roof, a white steeple, and a flagpole with an American flag.
A paved outdoor area with three Adirondack chairs, a street lamp, and a row of houses in the background.
A cozy room with a wicker sofa, two chairs, a small table, and large windows with a view of trees.

6. The Chatham Motel

The Chatham Motel
Chatham
  • Soak up summer vibes in this Cape Cod retreat with a seasonal outdoor pool, playground, and peaceful garden setting.
$219 nightly
$251 total
Oct 11 - Oct 12
Total with taxes and fees
The Chatham 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 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.
$110 nightly
$126 total
Oct 5 - Oct 6
Total with taxes and fees
Olde Tavern Motel And Inn
A swimming pool with lounge chairs and a building in the background.
An outdoor patio with round tables and chairs, picnic tables, and umbrellas.
A blue door labeled "Office" with a small window and a mailbox.
A bedroom with a bed, a table, two chairs, a lamp, and a window with curtains.

8. Handkerchief Shoals Inn

Handkerchief Shoals Inn
South Harwich
$134 nightly
$153 total
Sep 24 - Sep 25
Total with taxes and fees
Handkerchief Shoals Inn
A pool area with lounge chairs, a hot tub, and string lights.
A modern living room with a large blue sectional sofa, a woven coffee table, and a large window offering a view of the street.
A modern living room with a blue sofa, a coffee table, a large window, and a surfboard decoration.
A backyard with a fire pit, outdoor seating, string lights, and a hammock.

9. Dennis Port Surf Club (Boutique Hotel)

Dennis Port Surf Club (Boutique Hotel)
Dennis Port
  • Seasonal outdoor pool offers refreshing oceanside swims after coastal adventures.
$98 nightly
$112 total
Sep 15 - Sep 16
Total with taxes and fees
Dennis Port Surf Club (Boutique Hotel)
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.
Three children playing in shallow water on a beach.

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 vacation mood.
$181 nightly
$207 total
Sep 27 - Sep 28
Total with taxes and fees
The Villages at Ocean Edge
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

Greyfinch Chatham Inn

Greyfinch Chatham Inn

8/10 Good
"The property was absolutely charming and the room was spacious and adorable. Great parking and beautiful pool/fire pit area. Bicycles were available for riding around Chatham. We did find a bug in the bathroom which was a little disappointing. Overall, the stay was great and the bed was super comfortable."
Julie 1-night trip
Posted 6 hours ago
Greyfinch Chatham Inn
Chatham Bars Inn

Chatham Bars Inn

10/10 Excellent
"Exceptional"
Thomas 1-night trip
Posted 10 hours ago
Chatham Bars Inn
Bayside Resort Hotel

Bayside Resort Hotel

10/10 Excellent
"The fire pits outside were great!"
Leslie 1-night trip
Posted 14 hours ago
Bayside Resort Hotel
The Mariner Resort Cape Cod by The Red Collection

The Mariner Resort Cape Cod by The Red Collection

8/10 Good
"The room was clean and comfortable but the bathroom was quite small."
Elizabeth 3-night trip
Posted 17 hours ago
The Mariner Resort Cape Cod by The Red Collection
Chatham Wayside Inn

Chatham Wayside Inn

10/10 Excellent
"Amazing stay!!"
Ashley 1-night trip
Posted 1 day ago
Chatham Wayside Inn
All Seasons Resort, Trademark Collection by Wyndham

All Seasons Resort, Trademark Collection by Wyndham

10/10 Excellent
"Wonderful stay for our girls trip! Would absolutely come back."
Bernice 3-night trip
Posted 2 days ago
All Seasons Resort, Trademark Collection by Wyndham
Cape Sands Inn

Cape Sands Inn

8/10 Good
"Location was great"
Linda 2-night trip
Posted 2 days ago
Cape Sands Inn
Hyannis Harbor Hotel

Hyannis Harbor Hotel

8/10 Good
"Clean."
Tucker 3-night trip
Posted 2 days ago
Hyannis Harbor Hotel
Pleasant Bay Village Resort

Pleasant Bay Village Resort

10/10 Excellent
"A wonderful place to stay in Chatham. Literally a five minute drive to the pier fish market, Main Street and the beach. Check in was easy and the staff person was very helpful in pointing out places to eat and places to go both in Chatham and nearby Orleans. The room was very clean, spacious and the turn down service was excellent. They have a great pool and hot tub. They also have a koi fish pond that is beautiful. We especially enjoyed the outdoor tables in the courtyards of each area. We were able to bring back lobster rolls from the fish market and enjoy a nice al fresco dinner. We then ran into the cleaning who offered to take our garbage from us, which was so helpful as it prevented us from stinking up the room. I would definitely recommend this resort to anyone staying n Chatham. Well worth it!"
Kimberly 4-night trip
Posted 11 days ago
Pleasant Bay Village Resort

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 $112 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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