Photo by Patricia Knorr

Chester Hotel with Pool

Start date: Check-in selected.
To Date
End date: Check-out

  • 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 Hotel with Pool

Tonight
22 Nov - 23 Nov
Tomorrow
23 Nov - 24 Nov
Next weekend
28 Nov - 30 Nov
In two weeks
5 Dec - 7 Dec

Top Chester Hotel with Pool

Indoor pool, open 5 AM to 11 PM, pool loungers
Hilton Garden Inn Kent Island Marina

Hilton Garden Inn Kent Island Marina

3.0 star property
Grasonville
  • Indoor pool
  • Pool loungers
9.0 out of 10, Wonderful, (1001)
Waterfront serenity awaits at the indoor pool, complete with comfortable sun loungers and extended hours from 5 AM to 11 PM. Steps from the marina, this hotel combines aquatic pleasure with scenic beauty and a modern fitness centre.
The price is HK$928
HK$1,030 total
includes taxes & fees
21 Dec - 22 Dec
Hilton Garden Inn Kent Island Marina
Seasonal outdoor pool
Quality Inn

Quality Inn

2.5 star property
Easton
  • Pool
  • Breakfast included
  • Pet-friendly
  • Parking included
  • Free WiFi
  • Air conditioning
7.6 out of 10, Good, (817)
Poolside relaxation awaits after exploring the city centre at this welcoming hotel. Spacious, clean rooms provide comfort while friendly staff ensure exceptional service. Guests appreciate the quiet atmosphere, complimentary breakfast, and convenient amenities.
The price is HK$629
HK$691 total
includes taxes & fees
14 Dec - 15 Dec
Quality Inn
Seasonal outdoor pool
Knapps Narrows Marina & Inn

Knapps Narrows Marina & Inn

3.0 star property
Tilghman
  • Pool
  • Breakfast included
  • Parking included
  • Free WiFi
  • Air conditioning
  • Laundry
9.4 out of 10, Exceptional, (355)
Marina-side seasonal pool creates a serene retreat overlooking Chesapeake Bay waters. Guests appreciate the immaculate rooms with private balconies, complimentary bicycles for island adventures, and boat tours launching steps away.
The price is HK$778
HK$856 total
includes taxes & fees
23 Nov - 24 Nov
Knapps Narrows Marina & Inn
Seasonal outdoor pool, open 10:00 AM to 7:00 PM, pool umbrellas
St Michaels Inn

St Michaels Inn

2.5 star property
St. Michaels
  • Pool loungers
8.2 out of 10, Very good, (1000)
Sparkling waters beckon at the seasonal outdoor pool, complete with sun loungers and umbrellas from May through September. Conveniently situated near Chesapeake Bay Maritime Museum, this hotel offers continental breakfast and garden views after invigorating local hikes.
The price is HK$805
HK$886 total
includes taxes & fees
30 Nov - 1 Dec
St Michaels Inn
Indoor pool
Best Western Kent Narrows Inn

Best Western Kent Narrows Inn

2.5 star property
Grasonville
  • Indoor pool
  • Hot tub
8.0 out of 10, Very good, (1002)
Sparkling waters await in the pristine indoor swimming pool, complemented by a rejuvenating hot tub and sauna. Active travellers appreciate the nearby hiking trails while enjoying spotless accommodation with 49-inch TVs and refrigerators.
The price is HK$716
HK$795 total
includes taxes & fees
30 Nov - 1 Dec
Best Western Kent Narrows Inn
Lobby
Quality Inn

Quality Inn

2.5 star property
Grasonville
  • Pool
  • Breakfast included
  • Parking included
  • Free WiFi
  • Air conditioning
  • Business services
7.8 out of 10, Good, (852)
Cooling waters await at the seasonal outdoor pool, open 24 hours from May to October. This hotel sits near the Chesapeake Exploration Centre, offering comfortable rooms, a complimentary breakfast buffet, and friendly service praised by past guests.
The price is HK$723
HK$802 total
includes taxes & fees
21 Dec - 22 Dec
Quality Inn
Aerial view
Kent Island Resort

Kent Island Resort

3.5 star property
Stevensville
  • Outdoor pool
  • Pool loungers
9.2 out of 10, Wonderful, (125)
Sparkling waters welcome swimmers to this seasonal retreat where comfortable loungers await beneath shade umbrellas. Beyond the refreshing pool, adventures beckon with complimentary bicycles, kayaking, and fishing along the picturesque Chesapeake Bay.
The price is HK$975
HK$1,355 total
includes taxes & fees
1 Dec - 2 Dec
Kent Island Resort
Indoor pool
Country Inn & Suites by Radisson, Annapolis, MD

Country Inn & Suites by Radisson, Annapolis, MD

3.0 star property
Annapolis
  • Indoor pool
  • Hot tub
9.0 out of 10, Wonderful, (1003)
Surrounded by an atmosphere of quiet serenity, the indoor pool invites leisurely swims while the inviting hot tub soothes tired muscles. Spacious, clean rooms and friendly staff complete this comfortable Maryland retreat.
The price is HK$688
HK$784 total
includes taxes & fees
21 Dec - 22 Dec
Country Inn & Suites by Radisson, Annapolis, MD
Seasonal outdoor pool, open 9 AM to 9 PM, pool umbrellas, pool loungers
Holiday Inn Express Annapolis East-Kent Island by IHG

Holiday Inn Express Annapolis East-Kent Island by IHG

2.5 star property
Grasonville
  • Pool loungers
9.2 out of 10, Wonderful, (924)
Splashing in the seasonal outdoor pool reveals stunning Chesapeake Bay vistas, creating a waterfront oasis complete with sun loungers and umbrellas. Nearby adventures include hiking trails, kayaking, and sailing for the perfect coastal getaway.
The price is HK$741
HK$822 total
includes taxes & fees
14 Dec - 15 Dec
Holiday Inn Express Annapolis East-Kent Island by IHG
Indoor pool
Hampton Inn Easton

Hampton Inn Easton

2.5 star property
Easton
  • Indoor pool
9.0 out of 10, Wonderful, (549)
Aquatic adventures await in the indoor pool, accessible from morning to evening after a complimentary breakfast buffet. The fitness centre, immaculate rooms, and consistently praised staff complete this comfortable retreat for travellers seeking both activity and relaxation.
The price is HK$940
HK$1,034 total
includes taxes & fees
23 Dec - 24 Dec
Hampton Inn Easton
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.
View all properties

Black Friday Sale

Limited-time deals: Save up to 50% on select hotels
Book now

Top Chester Hotel Reviews

Hilton Garden Inn Kent Island Marina

Hilton Garden Inn Kent Island Marina

10/10 Excellent
"Check in was easy! Staff very friendly and helpful."
Ned 1-night trip
Posted 2 days ago
Hilton Garden Inn Kent Island Marina

Explore a world of travel with Expedia

Frequently asked questions

What are some hotels with pools in Chester?
Waterfront Home On 3 Acres. Fish,crab, & kayak from the pier + great sunsets!: Offers buffet, a seasonal outdoor pool and complimentary wireless Internet access. Historic Inns of Annapolis: Offers buffet, an indoor pool and free self parking. DoubleTree by Hilton Hotel Annapolis: Hotel located near U.S. Naval Academy. Provides free self parking, an indoor pool and complimentary wireless Internet access. Graduate by Hilton Annapolis: Hotel located near U.S. Naval Academy. Offers a full-service spa, an indoor pool and a snack bar/deli. Sonesta ES Suites Annapolis: Features buffet, a seasonal outdoor pool and complimentary high-speed (wired) Internet access.
What is there to see and do in Chester?
Enjoy a stroll along the shore at Sandy Point Beach and Bay Ridge Beach. Discover sights such as Northern Chesapeake Bay, Matapeake State Park and Eastern Neck National Wildlife Refuge during your stay.
When is the best time to book a hotel with a pool in Chester?
You may want to think about a place to stay with an outdoor swimming pool if you plan to visit Chester in the warmest months of July, August or June, when the average temp is 23°C. Accommodation offering an indoor pool may be the way to go if you are visiting during the coldest months of January, February or December, when the average temp is 4°C.