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 29 - Sep 30
Tomorrow
Sep 30 - Oct 1
This weekend
Oct 2 - Oct 4
Next weekend
Oct 9 - Oct 11

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 sandy beach path with a wooden fence leading to the ocean, under a partly cloudy sky.
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
Oct 29 - Oct 30
Total with taxes and fees
Chatham Wayside Inn
Four sun loungers aligned along a poolside with a tiled floor.
A white house with a grey roof, surrounded by a well-maintained lawn and flowering bushes.
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.

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.
$201 nightly
$230 total
Oct 18 - Oct 19
Total with taxes and fees
Greyfinch Chatham Inn
A swimming pool with clear blue water, surrounded by blue and white lounge 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.
A white desk with a woven hat, a vase with white flowers, and two glasses of white wine.

3. 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 14 - Oct 15
Total with taxes and fees
Chatham Seafarer 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 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.
$217 nightly
$249 total
Oct 4 - Oct 5
Total with taxes and fees
Pleasant Bay Village Resort
A resort pool with multiple sun loungers and umbrellas, surrounded by beach views and boats.
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.
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.

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.
$417 nightly
$477 total
Oct 19 - Oct 20
Total with taxes and fees
Chatham Bars Inn
Pool
A building with a blue roof, a white steeple, and a flagpole with an American flag.
A residential area with a house, a driveway, and a garden with flowering bushes.
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.
$204 nightly
$233 total
Oct 18 - Oct 19
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 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.

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.
$99 nightly
$113 total
Oct 1 - Oct 2
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 sign for Handkerchief Shoals Inn with a well-maintained garden in the foreground.

8. Handkerchief Shoals Inn

Handkerchief Shoals Inn
South Harwich
$134 nightly
$153 total
Oct 13 - Oct 14
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 room with arcade games, a TV, a large window, and a plant.

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.
$84 nightly
$96 total
Sep 30 - Oct 1
Total with taxes and fees
Dennis Port Surf Club (Boutique Hotel)
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 covered patio with a round table and four chairs.

10. 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.
$112 nightly
$128 total
Oct 13 - Oct 14
Total with taxes and fees
Skaket Beach Motel
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

Holiday Hill Inn & Suites

Holiday Hill Inn & Suites

8/10 Good
"Room was clean and staff was very helpful"
David 3-night trip
Posted 14 hours ago
Holiday Hill Inn & Suites
Hyannis Harbor Hotel

Hyannis Harbor Hotel

10/10 Excellent
"This hotel was beautiful, clean and well located. And as a bonus had a heated outdoor pool that is open till October."
Tiffany 1-night trip
Posted 17 hours ago
Hyannis Harbor Hotel
Margaritaville Resort Cape Cod

Margaritaville Resort Cape Cod

10/10 Excellent
"K"
Susan 2-night trip
Posted 20 hours ago
Margaritaville Resort Cape Cod
Chatham Seafarer Inn

Chatham Seafarer Inn

8/10 Good
"My room was beautiful and well appointed. Staff was so friendly and communicative. My only wish was that the other guests had been more respectful. talking full voice and allowing doors to slam after quiet hours had ended was a bummer."
Valerie 3-night trip
Posted 22 hours ago
Chatham Seafarer Inn
Riviera Beach Resort

Riviera Beach Resort

10/10 Excellent
"Beautiful location"
mike 2-night trip
Posted 23 hours ago
Riviera Beach Resort
Hyannis Travel Inn

Hyannis Travel Inn

10/10 Excellent
"Breakfast was hearty and healthy, air conditioning did a good job maintaining room comfort, staff was cheerful and very helpful. Will definitely be returning for another stay!"
Anne-Marie 2-night trip
Posted 2 days ago
Hyannis Travel Inn
Pleasant Bay Village Resort

Pleasant Bay Village Resort

10/10 Excellent
"Everything was exceptional!"
sheila 1-night trip
Posted 3 days ago
Pleasant Bay Village Resort
Chatham Wayside Inn

Chatham Wayside Inn

10/10 Excellent
"Loved the Inn and will definitely stay there again in the future. Perfect location...just steps to the shops and eateries on Main Street. Our standard king room was lovely and spacious. The mattress and bedding was extremely comfortable and had everything we needed. The gym and pool looked beautiful but unfortunately we didn't have a chance to use them. Dinner our first night at the tavern on the property was excellent. The seafood pot pie was absolutely! The only slight downside for us was that the continental breakfast was a bit lacking. Considering the price of the rooms, I think the Inn could do a little better. However, this would not keep us from staying here again. A great experience overall."
Debra 2-night trip
Posted 6 days ago
Chatham Wayside Inn
Greyfinch Chatham Inn

Greyfinch Chatham Inn

10/10 Excellent
"This place is so cute! When we first pulled up we were unsure because it looks like an old roadside motel. But it’s quickly apparent that it’s been beautifully updated with fresh paint and hanging plants. The driveway and parking lot are spotless as are the rooms. The decor in the rooms is updated and coastal. The staff was lovely. I would absolutely stay here again!"
Robert 4-night trip
Posted 6 days ago
Greyfinch Chatham 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 $113 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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