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
Aug 24 - Aug 25
Tomorrow
Aug 25 - Aug 26
This weekend
Aug 28 - Aug 30
Next weekend
Sep 4 - Sep 6

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.
A beach with a fallen tree, clear blue water, and a forested shoreline.

1. 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
Sep 22 - Sep 23
Total with taxes and fees
Chatham Seafarer Inn
A swimming pool with blue water, surrounded by lounge chairs and a waterfall feature.
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 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.

2. 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.
$239 nightly
$274 total
Sep 22 - Sep 23
Total with taxes and fees
Pleasant Bay Village Resort
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.

3. 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.
$253 nightly
$289 total
Sep 1 - Sep 2
Total with taxes and fees
Greyfinch Chatham 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 restaurant with long communal tables and booths, large windows, and a view of buildings outside.
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.
$394 nightly
$451 total
Aug 25 - Aug 26
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.
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 series of tents with beds and seating areas, surrounded by a garden with various plants and a wooden deck.

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 14 - Sep 15
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 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.

6. 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.
$126 nightly
$144 total
Sep 2 - Sep 3
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 sign for Handkerchief Shoals Inn with a well-maintained garden in the foreground.
A blue door labeled "Office" with a small window and a mailbox.

7. Handkerchief Shoals Inn

Handkerchief Shoals Inn
South Harwich
$178 nightly
$204 total
Sep 14 - Sep 15
Total with taxes and fees
Handkerchief Shoals Inn
A swimming pool with a fenced area, lounge chairs, and a building in the background.
A bathroom with a toilet, sink, and shower.
A covered patio with a round table and four chairs.
A brick building with a white picket fence, a lawn, and a sign for Skaket Beach Motel.

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.
$140 nightly
$160 total
Sep 15 - Sep 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.
An outdoor patio with tables and chairs, umbrellas, and a view of the ocean.
A restaurant with brick arches, wooden tables, and chairs. There is a bar area with bottles and a television screen.

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.
$190 nightly
$217 total
Sep 20 - Sep 21
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 hotel reception area with a blue wall, a reception desk, a large window, and a welcome mat.
A garden area with a welcome sign, outdoor seating, and a blue umbrella.
A bathroom with a shower curtain, a bathtub, and a tiled wall with a marble-like pattern.

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.
$135 nightly
$155 total
Sep 1 - Sep 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

Bayside Resort Hotel

Bayside Resort Hotel

8/10 Good
"Clean basic hotel. Nice that breakfast was included and nice fire pit and outdoor spaces. Finishes are all mid grade but overall it was a good experience, especially for a family."
Caitlin 1-night trip
Posted 10 hours ago
Bayside Resort Hotel
The Mariner Resort Cape Cod by The Red Collection

The Mariner Resort Cape Cod by The Red Collection

10/10 Excellent
"A good place to rest and relax; good service, comfort, and cleanliness."
Alejandra 3-night trip
Posted 11 hours ago
The Mariner Resort Cape Cod by The Red Collection
Hyannis Harbor Hotel

Hyannis Harbor Hotel

10/10 Excellent
"Very clean room and well kept all around. The location was perfect! Across the street from the ferry terminal to Nantucket. Lots of great dining options too!"
Kim 1-night trip
Posted 13 hours ago
Hyannis Harbor Hotel
Uncommoner Hotel by Reverie Boutique Collection

Uncommoner Hotel by Reverie Boutique Collection

10/10 Excellent
"Gorgeous rooms, both pools are lovely, the dinner and drinks were phenomenal, and the outdoor seating/fire pits were a lovely touch. Did not take advantage of the outdoor games or bike rentals but I would love to stay here again!"
Leah 2-night trip
Posted 20 hours ago
Uncommoner Hotel by Reverie Boutique Collection
Holiday Hill Inn & Suites

Holiday Hill Inn & Suites

8/10 Good
"The staff was very friendly and helpful. We were placed in a room directly outside the pool so our room smelt overwhelming like chlorine as soon as we opened the door. The two double beds were a full size, as apposed to queen, so they were a bit small for two people. The room was very clean, as was the entire property. The pool area was nice, but unfortunately, it was rainy and overcast curing our stay, so we did not use it. Based on this experience, I would stay there again in the future."
Jessica 1-night trip
Posted 20 hours ago
Holiday Hill Inn & Suites
Freebird Motor Lodge by Reverie Boutique Collection

Freebird Motor Lodge by Reverie Boutique Collection

10/10 Excellent
"Clean and convenient"
Kathy 2-night trip
Posted 21 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
"Good stay"
Stephen 3-night trip
Posted 2 days ago
Holiday Inn Express Hyannis Cape Cod by IHG
Greyfinch Chatham Inn

Greyfinch Chatham Inn

10/10 Excellent
"Clean room and great location"
Sara 3-night trip
Posted 4 days ago
Greyfinch Chatham Inn
Queen Anne Inn

Queen Anne Inn

8/10 Good
"The staff was very helpful for suggesting places to eat and visit"
Douglas 3-night trip
Posted 6 days ago
Queen Anne 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 $144 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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