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 30 - Oct 1
Tomorrow
Oct 1 - Oct 2
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 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.

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 white desk with a woven hat, a vase with white flowers, and two glasses of white wine.
A beach with a fallen tree, clear blue water, and a forested shoreline.

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 circular wooden structure with illuminated edges in a garden setting.
A dining area with a glass table, chairs, and a vase with flowers.
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.

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 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.

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 residential area with a house, a driveway, and a garden with flowering bushes.
A paved outdoor area with three Adirondack chairs, a street lamp, and a row of houses in the background.
A building with a blue roof, a white steeple, and a flagpole with an American flag.

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 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".
A modern bathroom with a glass-enclosed shower, a white sink, and a towel rack with folded 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.
$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.
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.
A bedroom with a bed, a table, two chairs, a lamp, and a window with curtains.

8. Handkerchief Shoals Inn

Handkerchief Shoals Inn
South Harwich
$134 nightly
$153 total
Oct 14 - Oct 15
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 blue sofa, a coffee table, a large window, and a surfboard decoration.
A backyard with a fire pit, outdoor seating, string lights, and a hammock.
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.
$98 nightly
$112 total
Oct 6 - Oct 7
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 bathroom with a toilet, sink, and shower.
A hotel room with two beds, a desk with a television, a red chair, and a window with green curtains.
A brick building with a white picket fence, a lawn, and a sign for Skaket Beach Motel.

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 19 - Oct 20
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

Uncommoner Hotel by Reverie Boutique Collection

Uncommoner Hotel by Reverie Boutique Collection

10/10 Excellent
"Nice hotel, restaurant with nice outdoor setting."
Monique 1-night trip
Posted 1 hour ago
Uncommoner Hotel by Reverie Boutique Collection
Chatham Seafarer Inn

Chatham Seafarer Inn

8/10 Good
"Our room was beautiful and very clean! A little odd there was not any staff on site outside the hours of 3 pm - 8 pm but we do not stay at many small hotels so maybe this is normal. They did give us a phone number to call."
Kimberly 2-night trip
Posted 7 hours ago
Chatham Seafarer Inn
Hyannis Travel Inn

Hyannis Travel Inn

10/10 Excellent
"Clean rooms and very helpful staff."
Louie 1-night trip
Posted 1 day ago
Hyannis Travel Inn
Cape Sands Inn

Cape Sands Inn

10/10 Excellent
"Staff was excellent hotel clean"
Jerome 2-night trip
Posted 1 day ago
Cape Sands Inn
Holiday Hill Inn & Suites

Holiday Hill Inn & Suites

8/10 Good
"Room was clean and staff was very helpful"
David 3-night trip
Posted 2 days ago
Holiday Hill Inn & Suites
Riviera Beach Resort

Riviera Beach Resort

10/10 Excellent
"Beautiful location"
mike 2-night trip
Posted 2 days ago
Riviera Beach Resort
Pleasant Bay Village Resort

Pleasant Bay Village Resort

10/10 Excellent
"Everything was exceptional!"
sheila 1-night trip
Posted 5 days ago
Pleasant Bay Village Resort
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 7 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 $112 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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