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

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Check availability on Chester Hotels with Pool

Tonight
10 Oct - 11 Oct
Tomorrow
11 Oct - 12 Oct
Next weekend
16 Oct - 18 Oct
In two weeks
23 Oct - 25 Oct

Our top choices for Chester hotels with a pool

A pool area with lounge chairs and umbrellas, a swimming pool, and a view of the sea.
A large hotel with a spacious outdoor patio area, multiple dining tables, and umbrellas.
A formal dining room with multiple tables and chairs, large windows with a city view, and a decorative carpet.
An aerial view of a coastal resort with a large pool, multiple buildings, and a well-maintained lawn.

1. Water's Edge Resort & Spa

Water's Edge Resort & Spa
Westbrook Center
  • Pristine waters await at this coastal retreat with private beach access and year-round pools.
฿6,307
฿7,831 total
includes taxes & fees
1 Nov - 2 Nov
Water's Edge Resort & Spa
An indoor swimming pool with a tiled floor, a pool ladder, and a ceiling with a grid pattern.
A hotel room with a large bed, a bathroom with a bathtub, a TV on a wooden cabinet, and a chair.
A hallway with a blue reception desk, framed artwork on the walls, and a wooden door with a men's restroom sign.
A hotel lobby with a reception desk, seating area, and a snack bar.

2. Quality Inn Old Saybrook - Westbrook

Quality Inn Old Saybrook - Westbrook
Old Saybrook
  • Plunge into pool paradise at this welcoming hotel with sun loungers and a relaxing indoor retreat.
฿3,249
฿3,736 total
includes taxes & fees
1 Nov - 2 Nov
Quality Inn Old Saybrook - Westbrook
A rectangular swimming pool with a fenced area, surrounded by trees and a concrete deck with white metal loungers.
A hotel room with two beds, a desk, a chair, a window with curtains, and two wall-mounted lamps.
A motel with a large parking lot and multiple rooms.
A hotel room with a large bed, two bedside tables, a desk with chairs, a TV, and a small table with flowers.

3. Clinton Motel

Clinton Motel
Clinton
  • Dive into cool relaxation at this coastal motel's seasonal pool, where Hammonasset Beach State Park adventures await.
฿2,615
฿3,008 total
includes taxes & fees
8 Nov - 9 Nov
Clinton Motel
An indoor swimming pool with clear blue water, wooden beams, and lounge chairs.
A two-story Victorian-style house with a balcony, a porch, and a small tower.
A marina with boats docked, a fire pit table, and outdoor seating.
An aerial view of a marina with boats docked, a parking lot, and buildings with a waterfront view.

4. Saybrook Point Resort & Marina

Saybrook Point Resort & Marina
Old Saybrook Center
  • Swim into serenity with three breathtaking pools and luxurious loungers for perfect poolside days at this resort.
฿9,355
฿11,932 total
includes taxes & fees
3 Nov - 4 Nov
Saybrook Point Resort & Marina
An indoor swimming pool with a tiled floor, a pool ladder, and lounge chairs along the wall.
A bathroom with a white sink, a mirror, a toilet, and a hairdryer on the wall.
An electric vehicle charging station with a sign indicating 'Electric Vehicle Parking Only While Charging.'
A hotel room with a bed, a desk, a chair, a sofa, and a window with curtains.

5. Sleep Inn & Suites Niantic North

Sleep Inn & Suites Niantic North
Niantic
  • Refreshing indoor pool retreat just steps from the beach makes a splash for aquatic adventures.
฿3,392
฿3,900 total
includes taxes & fees
8 Nov - 9 Nov
Sleep Inn & Suites Niantic North
A swimming pool area with blue walls, multiple chairs, and a lifeguard sign.
A modern hotel lobby with a central seating area, a bar, and a large TV screen.
A modern hotel with multiple floors, large windows, and a sign for Springhill Suites.
An outdoor seating area with a fire pit, chairs, and a building with large windows and a flat roof.

6. Springhill Suites by Marriott Hartford Cromwell

Springhill Suites by Marriott Hartford Cromwell
Cromwell
  • Splash into relaxation at this indoor pool retreat with fitness centre and firepit fun.
฿4,442
฿5,108 total
includes taxes & fees
1 Nov - 2 Nov
Springhill Suites by Marriott Hartford Cromwell
An indoor swimming pool with clear blue water, surrounded by lounge chairs and tables.
A hotel room with a bed, a desk, a television, a sofa, and a window with a view of trees.
An outdoor kitchen with a grill and a built-in stove, white chairs, and a red door.
A multi-story hotel with a central entrance, a parking lot, and landscaped areas with shrubs and flowers.

7. Homewood Suites by Hilton Wallingford-Meriden

Homewood Suites by Hilton Wallingford-Meriden
Wallingford
  • Splash into fun at this hotel with an indoor pool, fitness centre, and nearby skiing trails.
฿5,118
฿5,886 total
includes taxes & fees
18 Oct - 19 Oct
Homewood Suites by Hilton Wallingford-Meriden
A hotel room with a large bathtub, a desk with a lamp, a chair, and a bed with a red blanket.
A tranquil park with a gazebo, a pond with a fountain, and a building in the background.
A deck with a table and chairs under a blue umbrella, surrounded by a wooden deck and a white fence.
A multi-story residential building with blue trim and large windows.

8. Econo Lodge Inn & Suites Old Saybrook Westbrook

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 accommodation.
฿2,255
฿2,593 total
includes taxes & fees
25 Oct - 26 Oct
Econo Lodge Inn & Suites Old Saybrook Westbrook
An indoor swimming pool with clear water, a metal ladder, and a tiled floor.
A cozy dining area with a brick fireplace, wooden chairs, and tables set for a meal.
A spacious lobby with a fireplace, seating area, and a reception desk.
A brick building with a sign that reads "Inn at Middletown."

9. Inn at Middletown

Inn at Middletown
Washington Street Historic District
  • Dive into poolside luxury in this historic hotel with a blissful indoor retreat and hot tub sanctuary.
฿4,999
฿6,419 total
includes taxes & fees
21 Oct - 22 Oct
Inn at Middletown
An indoor swimming pool with clear water, surrounded by lounge chairs and a tiled deck.
A modern hotel lobby with a central bar area, refrigerated beverage dispensers, and a seating area with tables and chairs.
A hotel corridor with round tables, large windows, and a modern console table.
A modern living room with a flat-screen TV, a red armchair, a grey sofa, a wooden entertainment unit, and a large window with curtains.

10. Hilton Garden Inn Wallingford/Meriden

Hilton Garden Inn Wallingford/Meriden
Wallingford
  • Dive into year-round aquatic bliss at this hotel's pristine indoor pool sanctuary.
฿4,509
฿5,185 total
includes taxes & fees
1 Nov - 2 Nov
Hilton Garden Inn Wallingford/Meriden
View all properties

Choose what matters most at hotels with a pool in Chester

Breakfast included
4 stars
5 stars
Hot tub
Spa

Top Chester Hotel Reviews

Fairfield by Marriott Inn & Suites Uncasville Mohegan Sun Area

Fairfield by Marriott Inn & Suites Uncasville Mohegan Sun Area

10/10 Excellent
"Nice place to stay."
Sue 1-night trip
Posted 5 hours ago
Fairfield by Marriott Inn & Suites Uncasville Mohegan Sun Area
Mohegan Sun

Mohegan Sun

10/10 Excellent
"Wonderful overnight stay!!"
Beth 1-night trip
Posted 1 day ago
Mohegan Sun
Best Western Plus New England Inn & Suites

Best Western Plus New England Inn & Suites

8/10 Good
"The lady who does breakfast is exceptional. Friendly and keeps her station spotless and loaded up with items. The hotel should be very proud to have her. I didn't see her name, but having stayed at this hotel a few times she is the regular lady here."
Sean 3-night trip
Posted 2 days ago
Best Western Plus New England Inn & Suites
Hilton Garden Inn Wallingford/Meriden

Hilton Garden Inn Wallingford/Meriden

10/10 Excellent
"We were there for only 1 night for a concert, but the grounds, public areas and rooms were clean, comfortable and relaxing. The staff was friendly, kind and helpful. Would stay again and I would recommand you to friends and relatives. Food wise was okay, but pricey."
Laurel 1-night trip
Posted 4 days ago
Hilton Garden Inn Wallingford/Meriden
Clarion Inn North Haven - New Haven North

Clarion Inn North Haven - New Haven North

10/10 Excellent
"Room and bedding super clean. Staff very friendly and helpful. Property was messy because of construction. Not great for walking your dog."
Lorraine 1-night trip
Posted 6 days ago
Clarion Inn North Haven - New Haven North

Frequently asked questions

What are some accommodation options 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 swimming 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 that has an outdoor pool if you'll be visiting Chester in the hottest months of July, August or June, when the average temperature is 21°C. Accommodation with an indoor pool may be the way to go if you come to town during the coldest months of January, February or March, when the average temp is 2°C.

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