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 17 - Sep 18
Tomorrow
Sep 18 - Sep 19
This weekend
Sep 18 - Sep 20
Next weekend
Sep 25 - Sep 27

Our top choices for Chatham hotels with a pool

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 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.

1. 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
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 bedroom with a wooden wardrobe, a white robe hanging on the door, and a bed with a wooden frame.
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.
$201 nightly
$230 total
Oct 18 - Oct 19
Total with taxes and fees
Greyfinch Chatham 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 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.

3. 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.
$237 nightly
$271 total
Sep 30 - Oct 1
Total with taxes and fees
Pleasant Bay Village Resort
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.

4. 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.
$437 nightly
$500 total
Sep 29 - Sep 30
Total with taxes and fees
Chatham Wayside Inn
A resort pool with multiple sun loungers and umbrellas, surrounded by beach views and boats.
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.
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 12 - Oct 13
Total with taxes and fees
Chatham Bars Inn
A residential area with a house, a driveway, and a garden with flowering bushes.
A building with a blue roof, a white steeple, and a flagpole with an American flag.
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.
$186 nightly
$213 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 kitchen with a brick stove, a white countertop, and a sign labeled "POOL TOWELS".
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.

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.
$105 nightly
$120 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.
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.
An outdoor patio with round tables and chairs, picnic tables, and umbrellas.

8. Handkerchief Shoals Inn

Handkerchief Shoals Inn
South Harwich
$134 nightly
$153 total
Oct 1 - Oct 2
Total with taxes and fees
Handkerchief Shoals Inn
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.

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.
$109 nightly
$125 total
Oct 12 - Oct 13
Total with taxes and fees
Skaket Beach Motel
A clear swimming pool with blue lounge chairs and a blue umbrella.
A golf course with sand bunkers, trees, and a clear blue sky.
Three children playing in shallow water on a beach.
An outdoor patio with tables and chairs, umbrellas, and a view of the ocean.

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.
$172 nightly
$197 total
Oct 4 - Oct 5
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

Hyannis Travel Inn

Hyannis Travel Inn

8/10 Good
"Was a lower end hotel. You eat breakfast in hot pool area. The staff was great."
Roger 3-night trip
Posted 7 hours ago
Hyannis Travel Inn
Holiday Inn Express Hyannis Cape Cod by IHG

Holiday Inn Express Hyannis Cape Cod by IHG

10/10 Excellent
"Excellent!"
Lucimar 2-night trip
Posted 11 hours ago
Holiday Inn Express Hyannis Cape Cod by IHG
Hyannis Harbor Hotel

Hyannis Harbor Hotel

8/10 Good
"Parking sucks. You i have to use your room key to get out of the parking lot every time. That's especially inconvenient when you're checking out, you can't just leave your key in the room and drive off."
Michael 3-night trip
Posted 11 hours ago
Hyannis Harbor Hotel
Pleasant Bay Village Resort

Pleasant Bay Village Resort

10/10 Excellent
"We had an amazing anniversary stay. They surprised us w a bottle of champagne and swan towel arrangement on the bed. The room was impeccably clean. We had a beautiful outside area w chairs. All toiletries were provided along w a whirlpool tub. Peter was amazing and helpful. The outside pool and hot tub were both clean and so relaxing. We would absolutely stay here again! Enjoy!"
Donna 3-night trip
Posted 12 hours ago
Pleasant Bay Village Resort
Greyfinch Chatham Inn

Greyfinch Chatham Inn

10/10 Excellent
"The room was spotless and the staff was extremely welcoming. It’s the perfect location, just a short walk, drive, or borrowed bike into downtown Chatham. We told define return."
Dennis 3-night trip
Posted 13 hours ago
Greyfinch Chatham Inn
Bayside Resort Hotel

Bayside Resort Hotel

8/10 Good
"There was a bit of a musty smell but overall it was a good experience. Not quite sure why I paid a $60 charge upon my arrival but I was really too tired to question"
ROBIN 1-night trip
Posted 16 hours ago
Bayside Resort Hotel
Holiday Hill Inn & Suites

Holiday Hill Inn & Suites

10/10 Excellent
"clean and homy"
Cindy 3-night trip
Posted 1 day ago
Holiday Hill Inn & Suites
Uncommoner Hotel by Reverie Boutique Collection

Uncommoner Hotel by Reverie Boutique Collection

10/10 Excellent
"The property is lovely. I took my husband as an early birthday gift and he was so happy. Everything was beautiful and there is a good amount to do at the hotel and it's close to so much. The only thing I would suggest is bring your own beach towels because the ones at the pool are very small."
Jillian 2-night trip
Posted 2 days ago
Uncommoner Hotel by Reverie Boutique Collection
Cape Sands Inn

Cape Sands Inn

10/10 Excellent
"Always a pleasure to stay there. The staff is nice and accommodating, the property is very clean and the parking is great"
Nedenia 1-night trip
Posted 2 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 $120 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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