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 $178

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Check availability on Chatham Hotels with a Pool

Next weekend
Nov 13 - Nov 15
In two weeks
Nov 20 - Nov 22

Our top choices for Chatham hotels with a pool

A swimming pool with lounge chairs and a white fence.

1. Chatham Wayside Inn

Chatham Wayside Inn
4.0 star property
Chatham
9.2 out of 10, Wonderful, (765 reviews)
"Amazing stay!!"
Canada
Ashley
The price is CA $215
CA $307 total
includes taxes & fees
Nov 22 - Nov 23
Chatham Wayside Inn
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Choose what matters most at hotels with a pool in Chatham

Breakfast included
4 stars

Find out more about Chatham

Discover top Chatham attractions

Chatham offers a delightful blend of history, culture, and outdoor activities perfect for adventurous families. Start your exploration at the scenic waterfront, where you can enjoy leisurely strolls along the picturesque promenade, taking in views of the harbor and beyond. For those seeking a taste of local heritage, the historic district features charming architecture and informative plaques that tell the story of the town's maritime past. Art enthusiasts will appreciate the vibrant local art scene, with galleries showcasing works by local artists that capture the essence of the region. If you're looking to immerse yourself in nature, nearby parks provide scenic trails for walking and picnicking, allowing you to unwind amidst lush greenery. Finally, don't miss the opportunity to visit local markets where you can sample fresh produce and artisanal goods, offering a true taste of Chatham's community spirit. After a day of adventure, consider staying in one of the inviting accommodations in the heart of town, where attentive service and comfortable amenities ensure a restful experience.

Top Chatham Hotel Reviews

Fairfield Inn & Suites by Marriott Cape Cod Hyannis

Fairfield Inn & Suites by Marriott Cape Cod Hyannis

10/10 Excellent
"Its in a great location"
Estefany 1-night trip
Posted 10 hours ago
Fairfield Inn & Suites by Marriott Cape Cod Hyannis

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 $178 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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