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Hotels with Swimming Pool in Chester, Maryland

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Check availability on Chester Hotels with Swimming Pool

Our top choices for Chester hotels with a pool

Aerial view
Kent Island Resort

Kent Island Resort

Kent Island Resort
3.5 star property
Stevensville
9.2 out of 10, Wonderful, (130 reviews)
"Beautiful and peaceful property!"
United States
Jerry
The price is P7,496
P10,397 total
includes taxes & fees
Jan 11 - Jan 12
Kent Island Resort
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, (948 reviews)
"Great staff, clean room, nice view!"
United States
Quiana
The price is P5,623
P6,242 total
includes taxes & fees
Jan 19 - Jan 20
Holiday Inn Express Annapolis East-Kent Island by IHG
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, (365 reviews)
"nice clean room staff very nice would stay again "
United States
mario
The price is P5,919
P6,511 total
includes taxes & fees
Jan 11 - Jan 12
Knapps Narrows Marina & Inn
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, (1,000 reviews)
"Good value and close to downtown."
United States
John
The price is P5,953
P6,549 total
includes taxes & fees
Jan 18 - Jan 19
St Michaels 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, (695 reviews)
"Good breakfast, great view, clean and well run, pleasant staff, great dining options nearby. "
United States
Kevin
The price is P6,688
P7,424 total
includes taxes & fees
Jan 19 - Jan 20
Hyatt Place Kent Narrows & Marina
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, (1,002 reviews)
"Nice place "
United States
Tucker T
The price is P4,938
P5,481 total
includes taxes & fees
Jan 18 - Jan 19
Best Western Kent Narrows Inn
Seasonal outdoor pool
Quality Inn

Quality Inn

Quality Inn
2.5 star property
Easton
7.6 out of 10, Good, (832 reviews)
"Checkin staff was great. The motel is advertised as a HOTEL, and it very clearly is not."
United States
Jennifer
The price is P5,031
P5,534 total
includes taxes & fees
Jan 18 - Jan 19
Quality Inn
Seasonal outdoor pool
Wylder Tilghman Island

Wylder Tilghman Island

Wylder Tilghman Island
2.0 star property
Tilghman
8.8 out of 10, Excellent, (91 reviews)
"Very relaxing stay."
United States
Anne
The price is P6,870
P10,161 total
includes taxes & fees
Jan 15 - Jan 16
Wylder Tilghman Island
Outdoor pool
Anchored Inn at Hidden Harbour Marina

Anchored Inn at Hidden Harbour Marina

Anchored Inn at Hidden Harbour Marina
2.5 star property
Deale
9.4 out of 10, Exceptional, (473 reviews)
"Beautiful place to stay, we stay their one to two times a year."
United States
Marjorie
The price is P7,937
P9,049 total
includes taxes & fees
Jan 11 - Jan 12
Anchored Inn at Hidden Harbour Marina
Indoor pool, open 5 AM to 11 PM, sun loungers
Hilton Garden Inn Kent Island Marina

Hilton Garden Inn Kent Island Marina

Hilton Garden Inn Kent Island Marina
3.0 star property
Grasonville
9.0 out of 10, Wonderful, (1,003 reviews)
"Clean and friendly staff"
United States
Lisa
The price is P7,232
P8,027 total
includes taxes & fees
Jan 18 - Jan 19
Hilton Garden Inn Kent Island Marina
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.
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Top Chester Hotel Reviews

DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis

10/10 Excellent
"Very nice and neat hotel in good location. Staff are wonderful"
Sharath 1-night trip
Posted 2 days ago
DoubleTree by Hilton Hotel Annapolis

Frequently asked questions

What are some hotels with pools in Chester?
DoubleTree by Hilton Hotel Annapolis: Hotel located near U.S. Naval Academy. Features free self parking, an indoor pool, and complimentary wireless internet access. Graduate by Hilton Annapolis: Offers buffet, an indoor pool, and free self parking. Historic Inns of Annapolis: Provides buffet, a seasonal outdoor pool, and complimentary wireless internet access. Crowne Plaza Annapolis by IHG: Hotel located near U.S. Naval Academy. Features a full-service spa, an indoor pool, and a snack bar/deli. Annapolis Waterfront Hotel, Autograph Collection: Offers buffet, a seasonal outdoor pool, and complimentary 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 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.

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