Hotels with Pool & Resorts in Chester from NZ$155

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Check availability on Chester Hotels with Pool

Our top choices for Chester hotels with a pool

Seasonal outdoor pool

Knapps Narrows Marina & Inn

Knapps Narrows Marina & Inn
3.0 star property
Sherwood
9.4 out of 10, Exceptional, (368 reviews)
"Always a great time. "
United States
Randolph
The price is NZ$164
includes taxes & fees
16 Feb - 17 Feb
Knapps Narrows Marina & Inn
Indoor pool

Best Western Kent Narrows Inn

Best Western Kent Narrows Inn
2.5 star property
Grasonville
8.0 out of 10, Very good, (1,000 reviews)
"Nice breakfast, cleanroom. Great location."
United States
Wayne
The price is NZ$173
includes taxes & fees
16 Feb - 17 Feb
Best Western Kent Narrows 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
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 NZ$253
includes taxes & fees
17 Feb - 18 Feb
Anchored Inn at Hidden Harbour Marina
Seasonal outdoor pool

Quality Inn

Quality Inn
2.5 star property
Easton
7.6 out of 10, Good, (843 reviews)
"Checkin staff was great. The motel is advertised as a HOTEL, and it very clearly is not."
United States
Jennifer
The price is NZ$155
includes taxes & fees
22 Feb - 23 Feb
Quality Inn
Lobby

Quality Inn Grasonville near Kent Island

Quality Inn Grasonville near Kent Island
2.5 star property
Grasonville
7.8 out of 10, Good, (872 reviews)
"Nice staff and rooms"
United States
Walter
The price is NZ$155
includes taxes & fees
22 Feb - 23 Feb
Quality Inn Grasonville near Kent Island
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 NZ$217
includes taxes & fees
16 Feb - 17 Feb
Best Western Plus Easton Inn & Suites
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
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 NZ$210
includes taxes & fees
22 Feb - 23 Feb
Hilton Garden Inn Kent Island Marina
Seasonal outdoor pool

Wylder Tilghman Island

Wylder Tilghman Island
2.0 star property
Tilghman
8.8 out of 10, Excellent, (92 reviews)
"We were"
United States
Guevara
The price is NZ$304
includes taxes & fees
1 Mar - 2 Mar
Wylder Tilghman Island
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, (959 reviews)
"Clean room, I enjoy staying here every time I'm in the area"
United States
Peter
The price is NZ$206
includes taxes & fees
22 Feb - 23 Feb
Holiday Inn Express Annapolis East-Kent Island by IHG
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

SpringHill Suites by Marriott Annapolis

SpringHill Suites by Marriott Annapolis

10/10 Excellent
"Rooms clean and front desk personnel are very friendly and helpful. This is one of my favorite places to stay when on assignment in MD."
Ruby 2-night trip
Posted 2 days ago
SpringHill Suites by Marriott Annapolis

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 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.