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 12 - Sep 13
Tomorrow
Sep 13 - Sep 14
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 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.

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.
A white desk with a woven hat, a vase with white flowers, and two glasses of white wine.

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 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 dining area with a glass table, chairs, and a vase with flowers.

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.
$215 nightly
$246 total
Sep 22 - Sep 23
Total with taxes and fees
Pleasant Bay Village Resort
A swimming pool with lounge chairs and a white fence.
An outdoor seating area with tables and chairs, a sign for 'Wild Goose Tavern', and large windows.
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.
$397 nightly
$454 total
Sep 27 - Sep 28
Total with taxes and fees
Chatham Wayside Inn
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.
A residential area with a house, a driveway, and a garden with flowering bushes.

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 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.
A deck with white Adirondack chairs and a small round table, overlooking a beach and ocean.

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 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".

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
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 bedroom with a bed, a table, two chairs, a lamp, and a window with curtains.
A sign for Handkerchief Shoals Inn with a well-maintained garden in the foreground.
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
Sep 27 - Sep 28
Total with taxes and fees
Handkerchief Shoals Inn
A clear swimming pool with blue lounge chairs and a blue umbrella.
Three children playing in shallow water on a beach.
A golf course with sand bunkers, trees, and a clear blue sky.
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.
$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 hotel room with a large bed, two bedside tables, a wall-mounted painting, and a patterned carpet.
A bathroom with a shower curtain, a bathtub, and a tiled wall with a marble-like pattern.
A garden area with a welcome sign, outdoor seating, and a blue umbrella.

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
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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 Inn Express Hyannis Cape Cod by IHG

Holiday Inn Express Hyannis Cape Cod by IHG

10/10 Excellent
"Clean very nice staff Beautiful breakfast our stay could not have been better thank you so much"
James 3-night trip
Posted 7 hours ago
Holiday Inn Express Hyannis Cape Cod by IHG
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 7 hours 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 10 hours ago
Hyannis Harbor Hotel
The Mariner Resort Cape Cod by The Red Collection

The Mariner Resort Cape Cod by The Red Collection

10/10 Excellent
"Good"
Bethelehem 1-night trip
Posted 23 hours ago
The Mariner Resort Cape Cod by The Red Collection
The Villages at Ocean Edge

The Villages at Ocean Edge

10/10 Excellent
"Great"
Robert 1-night trip
Posted 1 day ago
The Villages at Ocean Edge
Greyfinch Chatham Inn

Greyfinch Chatham Inn

10/10 Excellent
"It's a short walk into downtown Chatham with sidewalks provided, so no walking on side of road. Very quiet at night, and hotel met every request. One exception - electrical outlets by the side of bathroom sink did not work. A little inconvenient to find other outlets that would accommodate our electrical uses. Other than that, very nice place to stay near Chatham. Completely renovated, and very clean."
Mary 4-night trip
Posted 2 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 $121 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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