The Best Hotels with a Pool in Chester, CT from ￥12,904 in 2026

Q: What are some accommodations with pools in Chester?

Regency Inn & Suites New London, Mystic : Features a snack bar/deli, an indoor pool, and buffet. Pier Blue Inn Old Saybrook - Essex : Hotel located near Mohegan Sun Casino. Provides a snack bar/deli, an indoor pool, and buffet. Hyatt Place Uncasville - Casino Area : Features a seasonal outdoor pool, an indoor pool, and a private beach. Motel 6 New Haven - Branford, CT : Hotel located near Mohegan Sun Casino. Features daily, an indoor pool, and free self parking. Microtel Inn & Suites by Wyndham Uncasville Casino Area : Resort, 15-minute walk from Mohegan Sun Casino. Offers 19 restaurants, 2 indoor pools, and a full-service spa.

A calm river with boats, wooden docks, and buildings along the shore.

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Our top choices for Chester hotels with a pool

An indoor swimming pool with a tiled floor, a pool ladder, and a ceiling with a grid pattern.

1. Quality Inn Old Saybrook - Westbrook

Old Saybrook

Plunge into pool paradise at this welcoming hotel with sun loungers and a relaxing indoor retreat.

￥17,550 total

includes taxes & fees

Nov 16 - Nov 17

A pool area with lounge chairs and umbrellas, a swimming pool, and a view of the sea.

2. Water's Edge Resort & Spa

Westbrook Center

Pristine waters await at this coastal retreat with private beach access and year-round pools.

￥36,003 total

includes taxes & fees

Nov 1 - Nov 2

A parking lot with a building in the background.

3. Clinton Motel

Clinton

Dive into cool relaxation at this coastal motel's seasonal pool, where Hammonasset Beach State Park adventures await.

￥14,071 total

includes taxes & fees

Nov 4 - Nov 5

A marina with boats docked, a fire pit table, and outdoor seating.

4. Saybrook Point Resort & Marina

Old Saybrook Center

Swim into serenity with three breathtaking pools and luxurious loungers for perfect poolside days at this resort.

￥49,948 total

includes taxes & fees

Nov 3 - Nov 4

A hotel room with a large bathtub, a desk with a lamp, a chair, and a bed with a red blanket.

5. Econo Lodge Inn & Suites Old Saybrook Westbrook

Old Saybrook

Soak in the serenity at this garden-view pool retreat offering refreshing summer escapes amid recently refreshed accommodations.

￥12,904 total

includes taxes & fees

Nov 11 - Nov 12

An indoor swimming pool with a no diving sign, a tiled wall, and a seating area with chairs.

6. Sleep Inn & Suites Niantic North

Niantic

Refreshing indoor pool retreat just steps from the beach makes a splash for aquatic adventures.

￥18,320 total

includes taxes & fees

Nov 16 - Nov 17

An indoor swimming pool with clear water, a metal ladder, and a tiled floor.

7. Inn at Middletown

Washington Street Historic District

Dive into poolside luxury in this historic hotel with a blissful indoor retreat and hot tub sanctuary.

￥31,403 total

includes taxes & fees

Oct 28 - Oct 29

An indoor swimming pool with clear blue water, surrounded by lounge chairs and tables.

8. Homewood Suites by Hilton Wallingford-Meriden

Wallingford

Splash into fun at this hotel with an indoor pool, fitness center, and nearby skiing trails.

￥24,324 total

includes taxes & fees

Nov 22 - Nov 23

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Choose what matters most at hotels with a pool in Chester

Breakfast included

4 stars

Top Chester Hotel Reviews

Microtel Inn & Suites by Wyndham Uncasville Casino Area

10/10 Excellent

"Nice hotel located close to casinos. Room was clean, breakfast was good and staff were nice."

Clarion Inn North Haven - New Haven North

10/10 Excellent

"The Inn is undergoing extensive renovation, so some of the common areas have construction debris. Set expectations accordingly. Nevertheless, front desk staff were very helpful and housekeeping did a great job in the room. My room was a new one, so very modern. Fixtures in the bathroom were great, with lots of hot water, fluffy towels and linen. The bed was comfortable, and there was a fridge, microwave, and coffee maker with pods. I’d definitely stay there again. And will, when I travel in that direction in the spring."

Regency Inn & Suites New London, Mystic

10/10 Excellent

"Don't expect the Ritz... The owner is amazing and the staff was wonderful. They were super nice and helpful! The breakfast was absolutely delicious! It's beautifully decorated. Love the picnic tables around the parking lot. Its easily accessible, right off the highway. I loved the affordable price. My kid (16) and his friends enjoyed the pool and having Chili's just a walk across the parking lot. We would definitely stay here again! Highly recommend!!"

Frequently asked questions

What are some accommodations with pools in Chester?

Regency Inn & Suites New London, Mystic: Features a snack bar/deli, an indoor pool, and buffet. Pier Blue Inn Old Saybrook - Essex: Hotel located near Mohegan Sun Casino. Provides a snack bar/deli, an indoor pool, and buffet. Hyatt Place Uncasville - Casino Area: Features a seasonal outdoor pool, an indoor pool, and a private beach. Motel 6 New Haven - Branford, CT: Hotel located near Mohegan Sun Casino. Features daily, an indoor pool, and free self parking. Microtel Inn & Suites by Wyndham Uncasville Casino Area: Resort, 15-minute walk from Mohegan Sun Casino. Offers 19 restaurants, 2 indoor pools, and a full-service spa.

What is there to see and do in Chester?

Take in the natural beauty with a stop at Connecticut River. Discover sights such as Chester Creek Marina, Norma Terris Theater, and Connecticut Valley Railroad State Park Trail during your stay.

When is the best time to book a hotel with a pool in Chester?

You may want to consider a place to stay with an outdoor swimming pool if you will be visiting Chester in the hottest months of July, August, or June when the average temperature is 70°F. Lodging with an indoor pool may be the way to go if you are visiting during the coldest months of January, February, or March when the average temp is 35°F.

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