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 13 - Sep 14
Tomorrow
Sep 14 - Sep 15
Next weekend
Sep 18 - Sep 20
In two weeks
Sep 25 - Sep 27

Our top choices for Chatham hotels with a pool

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 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.

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 house with a brick exterior, white exterior walls, and a front porch with white 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.

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 blue water, surrounded by lounge chairs and a waterfall feature.
A circular wooden structure with illuminated edges in a garden setting.
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.

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 22 - Sep 23
Total with taxes and fees
Pleasant Bay Village Resort
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.
An outdoor seating area with tables and chairs, a sign for 'Wild Goose Tavern', and large windows.

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.
$397 nightly
$454 total
Sep 29 - Sep 30
Total with taxes and fees
Chatham Wayside Inn
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.
A building with a blue roof, a white steeple, and a flagpole with an American flag.

5. 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 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 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.

6. 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.
$531 nightly
$608 total
Oct 12 - Oct 13
Total with taxes and fees
Chatham Bars Inn
A swimming pool with a metal ladder, surrounded by colorful plastic chairs, a red umbrella, and a building with a wooden exterior.
A hotel room with a large bed, teal walls, and a wooden headboard. There are two bedside tables with lamps and small plants.
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.

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.
$109 nightly
$125 total
Sep 15 - Sep 16
Total with taxes and fees
Olde Tavern Motel And Inn
A swimming pool with lounge chairs and a building in the background.
A sign for Handkerchief Shoals Inn with a well-maintained garden in the foreground.
A bedroom with a bed, a table, two chairs, a lamp, and a window with curtains.
A blue door labeled "Office" with a small window and a mailbox.

8. Handkerchief Shoals Inn

Handkerchief Shoals Inn
South Harwich
$134 nightly
$153 total
Sep 27 - Sep 28
Total with taxes and fees
Handkerchief Shoals Inn
A clear swimming pool with blue lounge chairs and a blue umbrella.
An outdoor patio with tables and chairs, umbrellas, and a view of the ocean.
Three children playing in shallow water on a beach.
A golf course with sand bunkers, trees, and a clear blue sky.

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.
$187 nightly
$214 total
Sep 27 - Sep 28
Total with taxes and fees
The Villages at Ocean Edge
A swimming pool with lounge chairs and umbrellas, surrounded by greenery and a building.
A garden area with a welcome sign, outdoor seating, and a blue umbrella.
A hotel room with a large bed, two bedside tables, a wall-mounted painting, and a patterned carpet.
A hotel reception area with a blue wall, a reception desk, a large window, and a welcome mat.

10. Rodeway Inn Orleans - Cape Cod

Rodeway Inn Orleans - Cape Cod
Orleans
  • Splash into refreshing luxury with a clean, spacious pool perfect for sunny Cape Cod afternoons.
$106 nightly
$121 total
Oct 1 - Oct 2
Total with taxes and fees
Rodeway Inn Orleans - Cape Cod
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

Cape Sands Inn

Cape Sands Inn

10/10 Excellent
"Clean room…super friendly housekeeping…front desk fast and efficient…booking was easy. This is my second time staying here. No reason to go elsewhere."
Stephanas 1-night trip
Posted 1 hour ago
Cape Sands Inn
Freebird Motor Lodge by Reverie Boutique Collection

Freebird Motor Lodge by Reverie Boutique Collection

10/10 Excellent
"Loved the old motel feel with a hip/colorful decor. Lovely property with convenient location, just little pricey as everything in Cape Cod."
Ludmila 2-night trip
Posted 2 hours ago
Freebird Motor Lodge by Reverie Boutique Collection
Holiday Inn Express Hyannis Cape Cod by IHG

Holiday Inn Express Hyannis Cape Cod by IHG

8/10 Good
"There were small flies and ants but otherwise the room was clean. Typical hotel room"
Ashley 2-night trip
Posted 3 hours ago
Holiday Inn Express Hyannis Cape Cod by IHG
Bayside Resort Hotel

Bayside Resort Hotel

10/10 Excellent
"Staff was super hospital. Maids were phenomenal. Breakfast was more than adequate. Pool was lovely, although the pool bar being closed was disappointing because it was Labor Day (not after.) The setting was serene and beautiful. We loved it."
Timothy 2-night trip
Posted 3 hours ago
Bayside Resort Hotel
Greyfinch Chatham Inn

Greyfinch Chatham Inn

10/10 Excellent
"check in and check out were quick and accurate. Didn't have any hiccups"
Adriana 3-night trip
Posted 6 hours ago
Greyfinch Chatham Inn
Uncommoner Hotel by Reverie Boutique Collection

Uncommoner Hotel by Reverie Boutique Collection

10/10 Excellent
"Clean room, very nice and helpful staff. Beautiful place"
Jennin 4-night trip
Posted 7 hours ago
Uncommoner Hotel by Reverie Boutique Collection
The Villages at Ocean Edge

The Villages at Ocean Edge

10/10 Excellent
"The place is very nice and HUGE. The convenience of jumping on the Cape Cod Rail trail from the property was awesome. We played a round of golf also and the course was in great shape! Definitely recommended!"
Deborah 5-night trip
Posted 9 hours ago
The Villages at Ocean Edge
Chatham Wayside Inn

Chatham Wayside Inn

10/10 Excellent
"It’s a great location and the staff were great. The room was nice but very small."
Haven 5-night trip
Posted 1 day ago
Chatham Wayside Inn
Hyannis Harbor Hotel

Hyannis Harbor Hotel

8/10 Good
"Needs a little more cleaning bathroom was dirty when we arrived. The staff is nice and helpful."
Yadira 2-night trip
Posted 1 day ago
Hyannis Harbor Hotel

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 $125 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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