Find Hotels with a Pool in Chester, MD

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Check availability on Chester Hotels with a Pool

Our top choices for Chester hotels with a pool

Indoor pool

Best Western Kent Narrows Inn

Best Western Kent Narrows Inn
2.5 star property
Grasonville
8.0 out of 10, Very Good, (1,001 reviews)
"Nice breakfast, cleanroom. Great location."
United States
Wayne
The price is AED 345
AED 383 total
includes taxes & fees
19 Feb - 20 Feb
Best Western Kent Narrows Inn
Outdoor pool

Anchored Inn at Hidden Harbour Marina

Anchored Inn at Hidden Harbour Marina
2.5 star property
Deale
9.4 out of 10, Exceptional, (476 reviews)
"Beautiful place to stay, we stay their one to two times a year."
United States
Marjorie
The price is AED 493
AED 562 total
includes taxes & fees
19 Feb - 20 Feb
Anchored Inn at Hidden Harbour Marina
Seasonal outdoor pool

Knapps Narrows Marina & Inn

Knapps Narrows Marina & Inn
3.0 star property
Sherwood
9.4 out of 10, Exceptional, (369 reviews)
"Clean room, helpful staff, nice breakfast, beautiful views, excellent location."
United States
Denise
The price is AED 367
AED 404 total
includes taxes & fees
23 Feb - 24 Feb
Knapps Narrows Marina & Inn
Seasonal outdoor pool

Quality Inn

Quality Inn
2.5 star property
Easton
7.6 out of 10, Good, (844 reviews)
"Checkin staff was great. The motel is advertised as a HOTEL, and it very clearly is not."
United States
Jennifer
The price is AED 312
AED 343 total
includes taxes & fees
24 Feb - 25 Feb
Quality 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
8.2 out of 10, Very Good, (1,000 reviews)
"Good value and close to downtown."
United States
John
St Michaels Inn
Indoor pool

Best Western Plus Easton Inn & Suites

Best Western Plus Easton Inn & Suites
2.5 star property
Easton
9.2 out of 10, Wonderful, (1,000 reviews)
"Nice friendly staff, clean room and lobby"
United States
Joi
The price is AED 437
AED 481 total
includes taxes & fees
19 Feb - 20 Feb
Best Western Plus Easton Inn & Suites
Lobby

Quality Inn Grasonville near Kent Island

Quality Inn Grasonville near Kent Island
2.5 star property
Grasonville
7.8 out of 10, Good, (874 reviews)
"Nice staff and rooms"
United States
Walter
The price is AED 309
AED 343 total
includes taxes & fees
16 Mar - 17 Mar
Quality Inn Grasonville near Kent Island
Indoor pool, open 5 AM to 11 PM, sun loungers

Hilton Garden Inn Kent Island Marina

Hilton Garden Inn Kent Island Marina
3.0 star property
Grasonville
9.0 out of 10, Wonderful, (1,000 reviews)
"Staff was friendly and rooms were clean. Beautiful area to visit. "
United States
Amy
The price is AED 419
AED 465 total
includes taxes & fees
22 Feb - 23 Feb
Hilton Garden Inn Kent Island Marina
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
2.5 star property
Grasonville
9.2 out of 10, Wonderful, (959 reviews)
"Clean room, I enjoy staying here every time I'm in the area"
United States
Peter
The price is AED 350
AED 388 total
includes taxes & fees
22 Feb - 23 Feb
Holiday Inn Express Annapolis East-Kent Island by IHG
Exterior

George Brooks House B&B

George Brooks House B&B
3.0 star property
St. Michaels
8.8 out of 10, Excellent, (67 reviews)
"Gorgeous quaint historic house. Friendly owner, close to town "
United States
Christopher
The price is AED 624
AED 687 total
includes taxes & fees
19 Feb - 20 Feb
George Brooks House B&B
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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Choose what matters most at hotels with a pool in Chester

Breakfast included
4 stars

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Top Chester Hotel Reviews

Graduate by Hilton Annapolis

Graduate by Hilton Annapolis

10/10 Excellent
"Nice room, enjoyed the hotel bar and restaurant and staff were friendly and helpful"
jennie 2-night trip
Posted 2 days ago
Graduate by Hilton Annapolis

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Frequently asked questions

What are some hotels with pools in Chester?
Waterfront Home On 3 Acres. Fish,crab, & kayak from the pier + great sunsets!: Features buffet, a seasonal outdoor pool, and complimentary wireless internet access. Historic Inns of Annapolis: Features buffet, an indoor pool, and free self parking. DoubleTree by Hilton Hotel Annapolis: Hotel located near U.S. Naval Academy. Offers free self parking, an indoor pool, and complimentary wireless internet access. Sonesta ES Suites Annapolis: Hotel located near U.S. Naval Academy. Features a full-service spa, an indoor pool, and a snack bar/deli. Graduate by Hilton Annapolis: Features a snack bar/deli, an indoor pool, and free self parking.
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.