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 from CA $157

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Check availability on Chatham Hotels with a Pool

Tonight
Sep 21 - Sep 22
Tomorrow
Sep 22 - Sep 23
This weekend
Sep 25 - Sep 27
Next weekend
Oct 2 - Oct 4

Our top choices for Chatham hotels with a pool

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 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.
CA $237
CA $322 total
includes taxes & fees
Oct 18 - Oct 19
Greyfinch Chatham Inn
A swimming pool with clear blue water, surrounded by blue and white lounge 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.
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.
CA $271
CA $311 total
includes taxes & fees
Oct 7 - Oct 8
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.

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.
CA $304
CA $348 total
includes taxes & fees
Oct 18 - Oct 19
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 sandy beach path with a wooden fence leading to the ocean, under a partly cloudy sky.
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.
CA $502
CA $636 total
includes taxes & fees
Sep 23 - Sep 24
Chatham Wayside Inn
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 cozy room with a wicker sofa, two chairs, a small table, and large windows with a view of trees.

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.
CA $260
CA $298 total
includes taxes & fees
Oct 18 - Oct 19
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 modern bathroom with a glass-enclosed shower, a white sink, and a towel rack with folded 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 kitchen with a brick stove, a white countertop, and a sign labeled "POOL TOWELS".

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.
CA $141
CA $162 total
includes taxes & fees
Oct 5 - Oct 6
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.
An outdoor patio with round tables and chairs, picnic tables, and umbrellas.
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
CA $187
CA $214 total
includes taxes & fees
Sep 22 - Sep 23
Handkerchief Shoals Inn
A swimming pool with a fenced area, lounge chairs, and a building in the background.
A brick building with a white picket fence, a lawn, and a sign for Skaket Beach Motel.
A hotel room with two beds, a desk with a television, a red chair, and a window with green curtains.
A covered patio with a round table and four chairs.

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.
CA $164
CA $187 total
includes taxes & fees
Oct 12 - Oct 13
Skaket Beach Motel
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.
CA $137
CA $157 total
includes taxes & fees
Sep 22 - Sep 23
Dennis Port Surf Club (Boutique Hotel)
A pool area with lounge chairs and a fire pit, surrounded by stone walls and potted plants.
A sunlit room with a view of the sea, featuring a sofa, a round table, and a chair.
A dining area with tables set for two, overlooking a body of water with a sailboat.
A balcony with wicker furniture, a table with a vase and wine glass, and a view of the sea.

10. Wequassett Resort and Golf Club

Wequassett Resort and Golf Club
Harwich
  • Swim through summer in a luxury cabana paradise with poolside bars and ocean breezes.
CA $586
CA $717 total
includes taxes & fees
Oct 19 - Oct 20
Wequassett Resort and Golf Club
View all properties

Choose what matters most at hotels with a pool in Chatham

Breakfast included
4 stars
5 stars
Hot tub
Spa

Top Chatham Hotel Reviews

Uncommoner Hotel by Reverie Boutique Collection

Uncommoner Hotel by Reverie Boutique Collection

8/10 Good
"The good: Very well done design and style. Convenient onsite cafe. Nice amenities. The not-so-good: Had some kind of fruit flies in our room upon check in and throughout the stay. Walls are paper thin. So you can hear the upstairs and side neighbors at a talking level. Which also means when someone is briskly walking back and forth upstairs for 30 minutes at 6am, it’s not pleasant. We also had a room near the entrance of the hallway. So when they play dancy house music early in the morning for the hallway vibes towards the cafe and pool, that’s also not pleasant to be woken up by. This is cape cod, not Vegas :-) Also, regardless if it’s an ADA room or not, the room could use a desk chair at the desk. Nice ambient lighting in the room, but really needs A LOT more lighting and lumens. All of the rooms face the parking lot with a big slider. So if you’re bottom floor, unless you want people staring in straight at you from the busy parking lot while you’re not decent and getting ready, you must shut the curtains on the slider. Which is very dark in the room. Ended up having the curtains closed the entire time due to this."
Ryan 3-night trip
Posted less than an hour ago
Uncommoner Hotel by Reverie Boutique Collection
Riviera Beach Resort

Riviera Beach Resort

10/10 Excellent
"U"
John 2-night trip
Posted 1 hour ago
Riviera Beach Resort
Holiday Inn Express Hyannis Cape Cod by IHG

Holiday Inn Express Hyannis Cape Cod by IHG

10/10 Excellent
"Breakfast was amazing a lot to choose from rooms were clean easy to park close to stores and whatever else you needed and staff was great and helpful"
Jose 1-night trip
Posted 2 hours ago
Holiday Inn Express Hyannis Cape Cod by IHG
Freebird Motor Lodge by Reverie Boutique Collection

Freebird Motor Lodge by Reverie Boutique Collection

10/10 Excellent
"Room was clean and cozy. Unique property with onsite food truck. Fire pits lit at night with seating."
Kristine 1-night trip
Posted 23 hours ago
Freebird Motor Lodge by Reverie Boutique Collection
Hyannis Harbor Hotel

Hyannis Harbor Hotel

8/10 Good
"Small bathroom and the shower didn't have a hand held shower. Old and thin towels."
Eileen 2-night trip
Posted 2 days ago
Hyannis Harbor Hotel
Holiday Hill Inn & Suites

Holiday Hill Inn & Suites

8/10 Good
"Great location, room was large."
Jackie 4-night trip
Posted 2 days ago
Holiday Hill Inn & Suites
Greyfinch Chatham Inn

Greyfinch Chatham Inn

10/10 Excellent
"The room was spotless and the staff was extremely welcoming. It’s the perfect location, just a short walk, drive, or borrowed bike into downtown Chatham. We told define return."
Dennis 3-night trip
Posted 5 days ago
Greyfinch Chatham Inn
Chatham Bars Inn

Chatham Bars Inn

10/10 Excellent
"Beautiful property with a very attentive staff. They helped make the engagement to my fiancée a wonderful and memorable experience! I highly recommend the spa with an intimate couples session! We will definitely be back in the future!"
Marcus 3-night trip
Posted 7 days ago
Chatham Bars 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 stands out for its inviting outdoor pool, complemented by beautifully landscaped grounds. Guests consistently praise the comfortable and clean rooms, alongside the friendly and attentive staff. With a remarkable review rating of 9.6, it's no wonder families appreciate the free WiFi and self-parking, making it a convenient choice for your stay in Chatham.For those seeking a more luxurious experience, Chatham Bars Inn is an exquisite 5-star option featuring a stunning outdoor pool and a host of top amenities including spa services and tennis courts. With a traveller rating of 9.2, visitors rave about the excellent service and the beautiful location right by the beach, ensuring a superb blend of relaxation and adventure. The dining options are also highly regarded, adding to the overall allure of this upscale retreat.If you're looking for a cozy, family-friendly atmosphere, The Chatham Motel, boasting an exceptional score of 9.2, offers an outdoor pool along with free WiFi and self-parking. Guests enjoy the friendly staff and the convenient location, making it easy to explore the charming surroundings of Chatham.Chatham Wayside Inn, rated 9.2 by travellers, is another wonderful option featuring an outdoor pool. Guests love the clean and charming rooms, as well as the friendly staff who go above and beyond to ensure a pleasant stay. Plus, the complimentary continental breakfast is a delightful addition for families looking to start their day off right.Lastly, Chatham Seafarer Inn, a 3.5-star hotel with a rating of 9.0, offers a comfortable atmosphere with an outdoor pool and proximity to the beach. Families appreciate the free cribs and the clean, cozy rooms, along with the excellent service provided by the friendly staff.
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 CA $157 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 hotel that stands out for its exceptional outdoor pool and breathtaking ocean views. Rated 9.2 by travellers, this luxurious resort offers a serene setting complemented by top amenities. Guests rave about the excellent service and extremely helpful staff, ensuring a memorable stay.Beyond the outdoor pool, Chatham Bars Inn provides a wealth of experiences, from private beach access to meticulously designed rooms featuring premium bedding and designer toiletries. For those looking to unwind, indulge in a relaxing massage or enjoy a game of tennis on the onsite courts. The beautiful location enhances the overall experience, making it a superb choice for families seeking both adventure and relaxation.
Are there hotels in Chatham with outdoor pool cabanas or loungers?
The Chatham Bars Inn is an exquisite 5-star hotel that offers a luxurious experience with its stunning outdoor pool, complete with comfortable loungers and beach sun loungers that invite relaxation under the sun. Guests rave about the exceptional service and helpful staff, ensuring a memorable stay. With a review rating of 9.2, travellers consistently highlight the top amenities and breathtaking location, making it a superb choice for families seeking both adventure and comfort.Another delightful option is the Queen Anne Inn, a charming 4-star property that features a resort-inclusive pool area along with sun loungers. With a review score of 8.8, this inn provides a cozy atmosphere suited for families, offering free breakfasts and amenities like complimentary cribs, which are especially appreciated by those traveling with little ones.Both hotels in Chatham not only cater to relaxation by the pool but also provide a welcoming environment for families eager to enjoy quality time together.
Are there hotels with outdoor pools that are close to Chatham Lighthouse Beach?
The Chatham Motel is a fantastic option for travellers seeking an outdoor pool near Chatham Lighthouse Beach. With an excellent review rating of 9.2, guests frequently praise the friendly staff and the motel's great location. Families will appreciate the playground for children, making it a convenient choice for those traveling with kids.Another excellent choice is the Chatham Wayside Inn, a charming 4-star property that also boasts a lovely outdoor pool. Rated 9.2 by travellers, the inn offers a delightful continental breakfast included with your stay, along with free Wi-Fi and self-parking. Guests have noted the clean and charming rooms, as well as the extremely helpful staff, ensuring a comfortable and enjoyable visit.
Is it cheaper to book flights and a hotel in Chatham 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 travel 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 with an outdoor pool in Chatham for you.
How can I save on a hotel in Chatham with Expedia?
Before booking your Chatham hotel, remember to join One Key™, Expedia's free travel rewards program. Just sign up and sign in to access instant discounts with Member Prices as well as member-only perks. Booking your hotel in advance will typically help you save, but there are last-minute deals to explore too.

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