A large, two-story house with a steeply pitched roof and a chimney.

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Check availability on Chester Hotels with a Pool

Tonight
29 Sep - 30 Sep
Tomorrow
30 Sep - 1 Oct
This weekend
2 Oct - 4 Oct
Next weekend
9 Oct - 11 Oct

Our top choices for Chester hotels with a pool

A pool area with chairs and a lifebuoy, large windows, and a view of the outdoors.
A modern dining area with wooden tables and chairs, large windows offering a view of a lake and bridge, and unique spherical hanging lights.
A lakeside view with several boats docked at a marina, surrounded by turquoise Adirondack chairs and a small fire pit.
A hotel with a large outdoor patio area, multiple balconies, and a well-lit entrance.

1. Oak Island Resort & Conference Centre

Oak Island Resort & Conference Centre
Western Shore
AED 566
AED 646 total
includes taxes & fees
22 Oct - 23 Oct
Oak Island Resort & Conference Centre
An indoor swimming pool with a blue slide, lounge chairs, and a red umbrella.
A hotel room with a sofa, a small table, a TV, a microwave, and a bathroom visible through an open door.
A spacious lobby with a reception desk, seating area, and a fireplace.
An outdoor patio area with tables and chairs, string lights, and wooden fences.

2. Best Western Plus Bridgewater Hotel & Convention Centre

Best Western Plus Bridgewater Hotel & Convention Centre
Cookville
  • Indoor pool paradise with waterslide makes this hotel a splash-filled retreat in Bridgewater.
AED 638
AED 728 total
includes taxes & fees
13 Oct - 14 Oct
Best Western Plus Bridgewater Hotel & Convention Centre
A view of a waterfront property with a dock and a small building.
A living room with a sofa, a chair, a coffee table, and a kitchen in the background.
A marina at dusk with boats docked, a wooden bridge, and a table with potted plants.
A room with a large skylight, a balcony with a wooden railing, and a view of the sea.

3. Luxury Oceanfront Retreat in Chester close to Mahone Bay, Lunenburg,

Luxury Oceanfront Retreat in Chester close to Mahone Bay, Lunenburg,
Western Shore
AED 1,010
AED 1,553 total
includes taxes & fees
7 Oct - 8 Oct
Luxury Oceanfront Retreat in Chester close to Mahone Bay, Lunenburg,
A waterfront property with a wooden deck, a swimming pool, and a view of the lake.
A residential area with a house, a swimming pool, and a marina with boats.
A row of houses with a gravel driveway leading to a dock by the water.
A marina with numerous boats docked, surrounded by a forested landscape.

4. SUN, SAND, OCEAN, in Hubbards. What more do you need?

SUN, SAND, OCEAN, in Hubbards. What more do you need?
Hubbards
AED 1,023
AED 1,691 total
includes taxes & fees
30 Sep - 1 Oct
SUN, SAND, OCEAN, in Hubbards. What more do you need?
A backyard with a swimming pool, a wooden deck, and a gazebo.
A view from a window overlooking a dock, a gazebo, and a body of water with boats.
A wooden deck with outdoor furniture, a pergola, and a view of a marina and water.
A two-story house with a covered porch and a white fence.

5. Oceanside Retreat Hubbards Nova Scotia

Oceanside Retreat Hubbards Nova Scotia
Hubbards
  • Oceanfront cottage captivates with a heated pool and scenic garden, where aquatic adventures and mountain views await.
AED 1,039
AED 1,714 total
includes taxes & fees
3 Oct - 4 Oct
Oceanside Retreat Hubbards Nova Scotia
A rectangular swimming pool with a metal ladder on the left side.
A wooden cabin with a porch, two windows, and a door leading inside.
A rustic wooden room with a bed, a table, and chairs. There is a 'No Smoking' sign on the wall.
A rustic cabin with a porch and a picnic table in a forest setting.

6. Oakhill Pines Campground

Oakhill Pines Campground
Oak Hill
  • Seasonal outdoor oasis with children's pool offers full-day access June through September.
Oakhill Pines Campground
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Choose what matters most at hotels with a pool in Chester

Breakfast included
4 stars
Hot tub
5 stars
Spa

Top Chester Hotel Reviews

Oak Island Resort & Conference Centre

Oak Island Resort & Conference Centre

8/10 Good
"Poor shower pressure rest was good."
Richard 1-night trip
Posted 15 hours ago
Oak Island Resort & Conference Centre

Frequently asked questions

What are some hotels with pools in Chester?
Bridgewater Hotel: Provides a snack bar/deli, an indoor pool, and continental. Travelodge by Wyndham Bridgewater: Features a seasonal outdoor pool, an indoor pool, and a sauna. Atlantic View Motel and Cottages: Offers a children's pool, a seasonal outdoor pool, and free self parking.
What is there to see and do in Chester?
Make a point to visit attractions like Oak Island and For The Birds Nature Shop. Discover sights such as Chester Art Center, Chester Playhouse, and Chester Golf Club during your stay.
When is the best time to book a hotel with a pool in Chester?
Taking into account the local weather in Chester is an important factor for planning your visit, especially if you plan to spend your trip poolside. The hottest months are usually August and July with an average temp of 62°F, while the coldest months are February and January with an average of 31°F. Average annual precipitation for Chester is 63 inches.