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Find Hotels with a Pool in Chester, MD

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Check availability on Chester Hotels with a Pool

Tonight
3 Jan - 4 Jan
Tomorrow
4 Jan - 5 Jan
Next weekend
9 Jan - 11 Jan
In two weeks
16 Jan - 18 Jan

Our top choices for Chester hotels with a pool

Seasonal outdoor pool, open 9 AM to 9 PM, pool umbrellas, sun loungers
Holiday Inn Express Annapolis East-Kent Island by IHG

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, (946)
"It was very comfortable and clean"
United States
Maria
The price is AED 320
AED 355 total
includes taxes & fees
19 Jan - 20 Jan
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

St Michaels Inn
2.5 star property
St. Michaels
8.2 out of 10, Very Good, (1001)
"Good value and close to downtown."
United States
John
The price is AED 347
AED 382 total
includes taxes & fees
14 Jan - 15 Jan
St Michaels Inn
Aerial view
Kent Island Resort

Kent Island Resort

Kent Island Resort
3.5 star property
Stevensville
9.2 out of 10, Wonderful, (130)
"Beautiful and peaceful property!"
United States
Jerry
The price is AED 441
AED 618 total
includes taxes & fees
4 Jan - 5 Jan
Kent Island Resort
Seasonal outdoor pool
Knapps Narrows Marina & Inn

Knapps Narrows Marina & Inn

Knapps Narrows Marina & Inn
3.0 star property
Tilghman
9.4 out of 10, Exceptional, (364)
"nice clean room staff very nice would stay again "
United States
mario
The price is AED 367
AED 404 total
includes taxes & fees
4 Jan - 5 Jan
Knapps Narrows Marina & Inn
Indoor pool
Best Western Kent Narrows Inn

Best Western Kent Narrows Inn

Best Western Kent Narrows Inn
2.5 star property
Grasonville
8.0 out of 10, Very Good, (1002)
"Nice place "
United States
Tucker T
The price is AED 306
AED 340 total
includes taxes & fees
11 Jan - 12 Jan
Best Western Kent Narrows Inn
Indoor pool, sun loungers
Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina
3.0 star property
Grasonville
9.6 out of 10, Exceptional, (691)
"Good breakfast, great view, clean and well run, pleasant staff, great dining options nearby. "
United States
Kevin
The price is AED 426
AED 473 total
includes taxes & fees
19 Jan - 20 Jan
Hyatt Place Kent Narrows & Marina
Seasonal outdoor pool
Quality Inn

Quality Inn

Quality Inn
2.5 star property
Easton
7.6 out of 10, Good, (831)
"Everything was clean; staff friendly; breakfast great"
United States
Richard
The price is AED 312
AED 343 total
includes taxes & fees
11 Jan - 12 Jan
Quality Inn
Exterior
The Inn at Chesapeake Bay Beach Club

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, (433)
"Very nice and clean! Only complaints A few stains on the couch And no body lotion. We really enjoyed our stay! "
United States
DEANNA
The price is AED 573
AED 729 total
includes taxes & fees
1 Feb - 2 Feb
The Inn at Chesapeake Bay Beach Club
Lobby
Quality Inn Grasonville near Kent Island

Quality Inn Grasonville near Kent Island

Quality Inn Grasonville near Kent Island
2.5 star property
Grasonville
7.8 out of 10, Good, (863)
"room was nice breakfast was good and the staff was very friendly and helpful. "
United States
Esai
The price is AED 309
AED 343 total
includes taxes & fees
4 Jan - 5 Jan
Quality Inn Grasonville near Kent Island
View from property
The Westin Annapolis

The Westin Annapolis

The Westin Annapolis
4.0 star property
Annapolis
8.6 out of 10, Excellent, (1002)
"Great hotel love that they are pet friendly. Easy check in and valet parking staff great"
United States
Robert
The price is AED 511
AED 582 total
includes taxes & fees
4 Jan - 5 Jan
The Westin Annapolis
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

Crowne Plaza Annapolis by IHG

Crowne Plaza Annapolis by IHG

10/10 Excellent
"Amazing staff and breakfast was delicious. "
jennifer 1-night trip
Posted 1 day ago
Crowne Plaza Annapolis by IHG

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Frequently asked questions

What are some hotels with pools in Chester?
DoubleTree by Hilton Hotel Annapolis: Hotel located near U.S. Naval Academy. Provides free self parking, an indoor pool, and complimentary wireless internet access. Historic Inns of Annapolis: Features buffet, an indoor pool, and free self parking. Crowne Plaza Annapolis by IHG: Hotel located near U.S. Naval Academy. Provides a full-service spa, an indoor pool, and a snack bar/deli. Graduate by Hilton Annapolis: Offers buffet, a seasonal outdoor pool, and complimentary wireless internet access. Hilton Garden Inn Annapolis Downtown: Features a snack bar/deli, an indoor pool, and daily.
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 Chesapeake Bay Environmental Center 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 temperature is 74°F. Lodging 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 39°F.