Photo by Patricia Knorr

Hotels with Pool & Resorts in Chester from NZ$145

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 Hotels with Pool

Best Chester Hotels with Pool

Seasonal outdoor pool
Knapps Narrows Marina & Inn

Knapps Narrows Marina & Inn

3.0 star property
Tilghman
9.4 out of 10, Exceptional, (352)
"Yes. room was spotless and staff was awesome!"
United States
Frank
The price is NZ$195
includes taxes & fees
12 Nov - 13 Nov
Knapps Narrows Marina & Inn
Seasonal outdoor pool
Quality Inn

Quality Inn

2.5 star property
Easton
7.6 out of 10, Good, (810)
"The staff was outstanding. Rooms were modest but clean. TV remote did not work. "
United States
Scott
The price is NZ$158
includes taxes & fees
7 Dec - 8 Dec
Quality Inn
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
9.2 out of 10, Wonderful, (917)
"The hotel was nice and clean and the staff was always polite and helpful. "
United States
William
The price is NZ$203
includes taxes & fees
19 Nov - 20 Nov
Holiday Inn Express Annapolis East-Kent Island by IHG
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
8.2 out of 10, Very good, (1001)
"clean and comfy, friendly staff"
United States
Tamara
The price is NZ$202
includes taxes & fees
7 Dec - 8 Dec
St Michaels Inn
Outdoor pool
Hilton Garden Inn Annapolis

Hilton Garden Inn Annapolis

3.0 star property
Annapolis
8.2 out of 10, Very good, (1000)
"Our stay at the hotel was easy check in and check out. Quiet and great location for our stay."
United States
Patricia
The price is NZ$145
includes taxes & fees
16 Nov - 17 Nov
Hilton Garden Inn Annapolis
Indoor pool
Best Western Kent Narrows Inn

Best Western Kent Narrows Inn

2.5 star property
Grasonville
8.0 out of 10, Very good, (1000)
"Our room was clean, smelled great, and the breakfast was good with many options."
United States
Eric
The price is NZ$181
includes taxes & fees
17 Nov - 18 Nov
Best Western Kent Narrows Inn
Seasonal outdoor pool
Wylder Tilghman Island

Wylder Tilghman Island

2.0 star property
Tilghman
8.8 out of 10, Excellent, (88)
"Fantastic escape with plenty of activities to do and things to explore would highly recommend to anyone looking to get away "
United States
Bryce
The price is NZ$373
includes taxes & fees
1 Dec - 2 Dec
Wylder Tilghman Island
Indoor pool
Country Inn & Suites by Radisson, Annapolis, MD

Country Inn & Suites by Radisson, Annapolis, MD

3.0 star property
Annapolis
9.0 out of 10, Wonderful, (1002)
"Room was great and the staff friendly and helpful."
United States
Newell
The price is NZ$188
includes taxes & fees
7 Dec - 8 Dec
Country Inn & Suites by Radisson, Annapolis, MD
Lobby
Quality Inn

Quality Inn

2.5 star property
Grasonville
7.8 out of 10, Good, (849)
"room was nice breakfast was good and the staff was very friendly and helpful. "
United States
Esai
The price is NZ$184
includes taxes & fees
23 Nov - 24 Nov
Quality Inn
Exterior
The Inn at Chesapeake Bay Beach Club

The Inn at Chesapeake Bay Beach Club

4.0 star property
Stevensville
9.4 out of 10, Exceptional, (426)
"Very nice atmosphere. Fall decor, multiple outdoor fireplaces, water fountains, everything clean, tidy, cozy, and all staff professionally courteous. Just very pleasant all around."
United States
Warren
The price is NZ$408
includes taxes & fees
1 Dec - 2 Dec
The Inn at Chesapeake Bay Beach Club
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

Top Chester Hotel Reviews

Country Inn & Suites by Radisson, Annapolis, MD

Country Inn & Suites by Radisson, Annapolis, MD

10/10 Excellent
"Came in late at night and left early the Inn was quiet, safe, comfortable and clean. Ice maker on 1st floor was out of order but there is a second one. Staff was attentive and helpful when we came in and check in was quick and easy. Would stay here again for other local sporting events. "
Thomas 1-night trip
Posted 3 days ago
Country Inn & Suites by Radisson, Annapolis, MD

Explore a world of travel with Expedia

Frequently asked questions

What are some hotels with pools in Chester?
Historic Inns of Annapolis: Offers buffet, an indoor pool and free self parking. Country Inn & Suites by Radisson, Annapolis, MD: Provides buffet, a seasonal outdoor pool and complimentary wireless Internet access. Sonesta ES Suites Annapolis: Hotel located near U.S. Naval Academy. Offers free self parking, an indoor pool and complimentary wireless Internet access. DoubleTree by Hilton Hotel Annapolis: Features a snack bar/deli, an indoor pool and free self parking. Crowne Plaza Annapolis by IHG: Hotel located near U.S. Naval Academy. Offers a full-service spa, an indoor pool and a snack bar/deli.
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 Matapeake State Park, Chesapeake Bay Environmental Center and Love Point State Park 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.