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
Oct 5 - Oct 6
Tomorrow
Oct 6 - Oct 7
This weekend
Oct 9 - Oct 11
Next weekend
Oct 16 - Oct 18

Our top choices for Chatham hotels with a pool

A swimming pool with lounge chairs and a white fence.
A garden with a pergola structure, a pathway, and a seating area.
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.

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
Nov 1 - Nov 2
Total with taxes and fees
Chatham Wayside Inn
Four sun loungers aligned along a poolside with a tiled floor.
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.
A modern kitchen with white cabinetry, a wooden island with two barstools, and a decorative wall art piece.

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.
$193 nightly
$220 total
Nov 1 - Nov 2
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 house with a brick exterior, white exterior walls, and a front porch with white chairs.
A white desk with a woven hat, a vase with white flowers, and two glasses of white wine.

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 20 - Oct 21
Total with taxes and fees
Chatham Seafarer Inn
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.

4. 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.
$391 nightly
$448 total
Nov 3 - Nov 4
Total with taxes and fees
Chatham Bars 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 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.

5. 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.
$220 nightly
$252 total
Oct 6 - Oct 7
Total with taxes and fees
Pleasant Bay Village Resort
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 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.

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.
$99 nightly
$113 total
Oct 7 - Oct 8
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 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.

7. Handkerchief Shoals Inn

Handkerchief Shoals Inn
South Harwich
$134 nightly
$153 total
Oct 20 - Oct 21
Total with taxes and fees
Handkerchief Shoals Inn
A swimming pool with lounge chairs and a covered seating area.
A hotel room with a bed, a bench, a desk, a microwave, and a television.
A covered porch with white Adirondack chairs, a trash can, and a door marked with the number 9.
A two-story house with a front porch, a mailbox, and a well-maintained garden.

8. Pelham on Earle

Pelham on Earle
West Harwich
  • Coastal getaway with a seasonal outdoor pool where relaxation awaits after exploring Cape Cod's beautiful beaches.
$204 nightly
$234 total
Oct 26 - Oct 27
Total with taxes and fees
Pelham on Earle
A hotel with a pool area, multiple balconies, and a fenced deck with lounge chairs.
A miniature golf course with two holes, a small pond, and a wooden bridge.
A beverage station with a Coca-Cola machine, ice dispensers, and a variety of drink options.
A reception desk with a marble top, a wooden panel base, a desk lamp, a potted plant, and a wicker chair with a cushion.

9. Holiday Hill Inn & Suites

Holiday Hill Inn & Suites
Dennis Port
  • Sparkling family-friendly pool oasis awaits at this beach-convenient motel with mini golf fun.
$89 nightly
$102 total
Oct 7 - Oct 8
Total with taxes and fees
Holiday Hill Inn & Suites
A clear swimming pool with blue lounge chairs and a blue umbrella.
A restaurant with brick arches, wooden tables, and chairs. There is a bar area with bottles and a television screen.
An outdoor patio with tables and chairs, umbrellas, and a view of the ocean.
A golf course with sand bunkers, trees, and a clear blue sky.

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.
$167 nightly
$191 total
Nov 1 - Nov 2
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

Bayside Resort Hotel

Bayside Resort Hotel

8/10 Good
"Our room was extremely clean and neat. The inside of the hotel in all the areas was very neat and clean. My only concern was that one of the outside lights that lit part of the parking lot was out. It was a bit unnerving to walk to the car in the dark"
rosalina 2-night trip
Posted less than an hour ago
Bayside Resort Hotel
Holiday Hill Inn & Suites

Holiday Hill Inn & Suites

8/10 Good
"On the down side 1) strong odor of cleaner/ disinfectant 2) Dated decor 3) limited cable access On the plus side 1) sign in was a breeze 2) free internet 3) room was clean and well stocked 4) Quiet"
Edward 1-night trip
Posted 4 hours ago
Holiday Hill Inn & Suites
Cape Sands Inn

Cape Sands Inn

8/10 Good
"At this price point, Cape Sands Inn is excellent value. We stayed in room 212, which had a small, but useful balcony that looked out over the garden, barbeque area, and the creek. The room had 2 comfortable queen beds, a large fridge, a coffee maker, and everything worked. I had to ask reception to turn up the hot water, which they did - straight away. I had to learn that it was necessary to run the bath tub tap until the water got hot to get hot water from the sink tap. Once I understood what I had to do, it was easy. The cleaners did a good job, every 2 days. The reception staff were nice and very helpful. It was a very good experience :)"
Simeon 7-night trip
Posted 5 hours ago
Cape Sands Inn
Red Jacket Beach Resort

Red Jacket Beach Resort

8/10 Good
"We enjoy our stay. Staff was friendly, plenty of parking- the beach with chairs, lounges and games was easily accessible. The pool area was very nice."
Marci 2-night trip
Posted 7 hours ago
Red Jacket Beach Resort
Uncommoner Hotel by Reverie Boutique Collection

Uncommoner Hotel by Reverie Boutique Collection

10/10 Excellent
"Loved the hotel and can’t speak more highly of the staff. Only disappointment was the restaurant and grounds were closed our second night due to a private function. Our first night was rained out so giving up our last night to a private party was unfortunate. Maybe in the future they will open some part of the property for hotel guests to enjoy while accommodating a private party."
Melissa 2-night trip
Posted 22 hours ago
Uncommoner Hotel by Reverie Boutique Collection
Riviera Beach Resort

Riviera Beach Resort

10/10 Excellent
"Great property and excellent location!"
Brian 2-night trip
Posted 2 days ago
Riviera Beach Resort
Hyannis Travel Inn

Hyannis Travel Inn

10/10 Excellent
"The staff were friendly and helpful. Great location. I would definitely stay again!"
Tracy 3-night trip
Posted 2 days ago
Hyannis Travel Inn
Greyfinch Chatham Inn

Greyfinch Chatham Inn

10/10 Excellent
"Perfect location. Straight up honesty, it’s not a resort or a newly appointed hotel, but the location is perfect for walking in to town and the rooms are clean and quiet. Compared to other Cape hotels, this is unbeatable for price, quality and location."
Jacob 2-night trip
Posted 3 days ago
Greyfinch Chatham Inn
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 5 days ago
Chatham Seafarer 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 $102 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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