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

Find Hotels with a Pool in Chester, CT

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Chester Hotels with a Pool

Tonight
Aug 29 - Aug 30
Tomorrow
Aug 30 - Aug 31
Next weekend
Sep 4 - Sep 6
In two weeks
Sep 11 - Sep 13

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.
A hotel lobby with a reception desk, two sofas, a coffee table, and a carpeted floor.
A hallway with a blue reception desk, framed artwork on the walls, and a wooden door with a men's restroom sign.
A hotel room with a large bed, a bathroom with a bathtub, a TV on a wooden cabinet, and a chair.

1. 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.
NT$3,198
NT$3,678 total
includes taxes & fees
Sep 27 - Sep 28
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 a large bed, two bedside tables, a desk with chairs, a TV, and a small table with flowers.
A hotel room with two beds, a desk, a chair, a window with curtains, and two wall-mounted lamps.
A parking lot with a building in the background.

2. Clinton Motel

Clinton Motel
Clinton
  • Dive into cool relaxation at this coastal motel's seasonal pool, where Hammonasset Beach State Park adventures await.
NT$2,498
NT$2,873 total
includes taxes & fees
Aug 31 - Sep 1
Clinton Motel
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 hotel lobby with a reception desk, a flat-screen TV mounted above a fireplace, and comfortable seating areas.
A deck with a table and chairs under a blue umbrella, surrounded by a wooden deck and a white fence.

3. 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 accommodations.
NT$2,404
NT$2,765 total
includes taxes & fees
Sep 27 - Sep 28
Econo Lodge Inn & Suites Old Saybrook Westbrook
A hotel room with a bed, a sofa, a table, and a lamp.
A shower stall with a grab bar, a handheld showerhead, and a seat.
A hotel room with a bed, a desk, a chair, a sofa, and a window with curtains.

4. 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.
NT$2,956
NT$3,400 total
includes taxes & fees
Sep 22 - Sep 23
Sleep Inn & Suites Niantic North
A pool area with lounge chairs and umbrellas, a swimming pool, and a view of the sea.
A balcony with a view of the ocean, a white railing, and two white chairs with blue cushions.
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.

5. 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.
NT$7,370
NT$9,022 total
includes taxes & fees
Sep 15 - Sep 16
Water's Edge Resort & Spa
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 at sunset with boats docked, a fire feature on the deck, and a chair.
A marina with boats docked, a fire pit table, and outdoor seating.

6. 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.
NT$11,667
NT$14,524 total
includes taxes & fees
Sep 27 - Sep 28
Saybrook Point Resort & Marina
An indoor swimming pool with clear water, a metal ladder, and a tiled floor.
A brick building with a sign that reads "Inn at Middletown."
A spacious lobby with a fireplace, seating area, and a reception desk.
A grand spiral staircase with a chandelier, marble flooring, and blue armchairs in a spacious lobby area.

7. 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.
NT$5,063
NT$6,455 total
includes taxes & fees
Sep 8 - Sep 9
Inn at Middletown
An indoor swimming pool with clear water, surrounded by lounge chairs and a tiled deck.
A hotel corridor with round tables, large windows, and a modern console table.
A Hilton Garden Inn with a covered entrance, landscaped gardens, and a clear sky.
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.

8. 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.
NT$4,382
NT$5,039 total
includes taxes & fees
Sep 8 - Sep 9
Hilton Garden Inn Wallingford/Meriden
A hotel reception area with a wooden counter, a coffee machine, and a buffet setup.
A hotel room with two beds, a TV, a dresser, a mirror, and a desk with a chair.
A reception desk with a wooden panel design, a private room sign, and a welcome sign listing amenities like breakfast, remote TV, and an exercise room.
A two-story hotel with a front porch, a brick entrance, and a car parked in the driveway.

9. Rodeway Inn Waterford - New London

Rodeway Inn Waterford - New London
Waterford
  • Tranquil seasonal outdoor pool awaits with perfect water temperature for your sun-soaked escape.
NT$2,975
NT$3,422 total
includes taxes & fees
Sep 23 - Sep 24
Rodeway Inn Waterford - New London
An indoor swimming pool with metal ladders and a tiled edge.
A hotel bathroom with a sink, mirror, and toilet.
A multi-story hotel with a glass entrance and a sign reading "HYATT PLACE".
A hotel room with a large bed, two bedside tables, a nightstand, a window with a view of greenery, and wall-mounted lights.

10. Hyatt Place Uncasville - Casino Area

Hyatt Place Uncasville - Casino Area
Montville
  • Year-round swimming perfection awaits in the indoor pool, just steps from Mohegan Sun Casino.
NT$3,225
NT$3,709 total
includes taxes & fees
Sep 29 - Sep 30
Hyatt Place Uncasville - Casino Area
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

Hyatt Place Uncasville - Casino Area

Hyatt Place Uncasville - Casino Area

8/10 Good
"Great hotel. Comfortable and quiet"
Stephanie 1-night trip
Posted 3 hours ago
Hyatt Place Uncasville - Casino Area
Microtel Inn & Suites by Wyndham Uncasville Casino Area

Microtel Inn & Suites by Wyndham Uncasville Casino Area

10/10 Excellent
"Clean rooms. Nice breakfast"
Nat 4-night trip
Posted 16 hours ago
Microtel Inn & Suites by Wyndham Uncasville Casino Area
Fairfield by Marriott Inn & Suites Uncasville Mohegan Sun Area

Fairfield by Marriott Inn & Suites Uncasville Mohegan Sun Area

8/10 Good
"All great!"
Chuklin 2-night trip
Posted 17 hours ago
Fairfield by Marriott Inn & Suites Uncasville Mohegan Sun Area
The Spa at Norwich Inn

The Spa at Norwich Inn

10/10 Excellent
"Staff was very friendly and helpful at check in. They answered all my questions and told me everything that was included with my stay. The lobby and hotel in general was very well maintained. It was my first stay and I’ll definitely be back."
Michelle 1-night trip
Posted 2 days ago
The Spa at Norwich Inn

Frequently asked questions

What are some accommodations with pools in Chester?
Motel 6 New Haven - Branford, CT: Hotel located near Mohegan Sun Casino. Provides a snack bar/deli, an indoor pool, and buffet. Pier Blue Inn Old Saybrook - Essex: Offers a seasonal outdoor pool, an indoor pool, and a private beach. Hyatt Place Uncasville - Casino Area: Hotel located near Mohegan Sun Casino. Features daily, an indoor pool, and free self parking. Microtel Inn & Suites by Wyndham Uncasville Casino Area: Hotel located near Naval Submarine Base New London. Offers a snack bar/deli, an indoor pool, and buffet. Water's Edge Resort & Spa: Hotel located near Naval Submarine Base New London. Provides free self parking, an indoor pool, and complimentary wireless internet access.
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.

Explore a world of travel with Expedia