Photo by Patricia Knorr

Chester Hotel Guide - Hotels with Pool in Chester, Maryland

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Check availability on Chester Hotels with Pool

Tonight
30 Nov - 1 Dec
Tomorrow
1 Dec - 2 Dec
Next weekend
5 Dec - 7 Dec
In two weeks
12 Dec - 14 Dec

Top Chester Hotels with Pool

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
  • Pool loungers
9.2 out of 10, Wonderful, (927)
Splashing in the seasonal outdoor pool reveals stunning Chesapeake Bay vistas, creating a waterfront oasis complete with sun loungers and umbrellas. Nearby adventures include hiking trails, kayaking, and sailing for the perfect coastal getaway.
The price is €76
includes taxes & fees
14 Dec - 15 Dec
Holiday Inn Express Annapolis East-Kent Island by IHG
Aerial view
Kent Island Resort

Kent Island Resort

3.5 star property
Stevensville
  • Outdoor pool
  • Pool loungers
9.2 out of 10, Wonderful, (127)
Sparkling waters welcome swimmers to this seasonal retreat where comfortable loungers await beneath shade umbrellas. Beyond the refreshing pool, adventures beckon with complimentary bicycles, kayaking, and fishing along the picturesque Chesapeake Bay.
The price is €136
includes taxes & fees
7 Dec - 8 Dec
Kent Island Resort
Seasonal outdoor pool
Quality Inn

Quality Inn

2.5 star property
Easton
  • Pool
  • Breakfast included
  • Pet-friendly
  • Parking included
  • Free WiFi
  • Air conditioning
7.6 out of 10, Good, (822)
Poolside relaxation awaits after exploring the city centre at this welcoming hotel. Spacious, clean rooms provide comfort while friendly staff ensure exceptional service. Guests appreciate the quiet atmosphere, complimentary breakfast, and convenient amenities.
The price is €77
includes taxes & fees
14 Dec - 15 Dec
Quality Inn
Outdoor pool
Hilton Garden Inn Annapolis

Hilton Garden Inn Annapolis

3.0 star property
Annapolis
  • Outdoor pool
8.2 out of 10, Very good, (1001)
Sparkling waters beckon at the well-maintained outdoor pool, a highlight praised by guests for its cleanliness and welcoming atmosphere. After swimming, visitors can energise at the 24-hour fitness centre or dine at the Garden Grille and Bar.
The price is €64
includes taxes & fees
21 Dec - 22 Dec
Hilton Garden Inn Annapolis
Seasonal outdoor pool
Knapps Narrows Marina & Inn

Knapps Narrows Marina & Inn

3.0 star property
Tilghman
  • Pool
  • Breakfast included
  • Parking included
  • Free WiFi
  • Air conditioning
  • Laundry
9.4 out of 10, Exceptional, (358)
Marina-side seasonal pool creates a serene retreat overlooking Chesapeake Bay waters. Guests appreciate the immaculate rooms with private balconies, complimentary bicycles for island adventures, and boat tours launching steps away.
The price is €114
includes taxes & fees
1 Dec - 2 Dec
Knapps Narrows Marina & Inn
Lobby
Quality Inn

Quality Inn

2.5 star property
Grasonville
  • Pool
  • Breakfast included
  • Parking included
  • Free WiFi
  • Air conditioning
  • Business services
7.8 out of 10, Good, (855)
Cooling waters await at the seasonal outdoor pool, open 24 hours from May to October. This hotel sits near the Chesapeake Exploration Centre, offering comfortable rooms, a complimentary breakfast buffet, and friendly service praised by past guests.
The price is €81
includes taxes & fees
14 Dec - 15 Dec
Quality Inn
Seasonal outdoor pool
Wylder Tilghman Island

Wylder Tilghman Island

2.0 star property
Tilghman
  • On private beach
8.8 out of 10, Excellent, (89)
Seasonal outdoor swimming beckons travellers from March through October at this waterfront haven. Complementing the pool, a private beach, sauna, and free bicycles create perfect relaxation opportunities along the river's edge.
The price is €153
includes taxes & fees
2 Dec - 3 Dec
Wylder Tilghman Island
Indoor pool, pool loungers
Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina

3.0 star property
Grasonville
  • Indoor pool
  • Pool loungers
9.4 out of 10, Exceptional, (668)
Pool loungers invite guests to unwind beside the tranquil indoor pool after exploring nearby trails and beaches. With stunning waterfront vistas, delicious breakfast options, and spacious, comfortable rooms, this hotel offers a serene island retreat.
The price is €111
includes taxes & fees
2 Dec - 3 Dec
Hyatt Place Kent Narrows & Marina
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
  • Pool loungers
8.2 out of 10, Very good, (1005)
Sparkling waters beckon at the seasonal outdoor pool, complete with sun loungers and umbrellas from May through September. Conveniently situated near Chesapeake Bay Maritime Museum, this hotel offers continental breakfast and garden views after invigorating local hikes.
The price is €105
includes taxes & fees
1 Dec - 2 Dec
St Michaels Inn
Indoor pool
Best Western Kent Narrows Inn

Best Western Kent Narrows Inn

2.5 star property
Grasonville
  • Indoor pool
  • Hot tub
8.0 out of 10, Very good, (1010)
Sparkling waters await in the pristine indoor swimming pool, complemented by a rejuvenating hot tub and sauna. Active travellers appreciate the nearby hiking trails while enjoying spotless accommodation with 49-inch TVs and refrigerators.
The price is €88
includes taxes & fees
8 Dec - 9 Dec
Best Western Kent Narrows Inn
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

Hilton Garden Inn Kent Island Marina

Hilton Garden Inn Kent Island Marina

10/10 Excellent
"Amazing location. Clean and well kept. "
Vince 1-night trip
Posted 2 days ago
Hilton Garden Inn Kent Island Marina

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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!: Hotel located near U.S. Naval Academy. Offers free self parking, an indoor pool and complimentary wireless Internet access. Crowne Plaza Annapolis by IHG: Features buffet, a seasonal outdoor pool and complimentary wireless Internet access. Historic Inns of Annapolis: Offers buffet, an indoor pool and free self parking. DoubleTree by Hilton Hotel Annapolis: Hotel located near U.S. Naval Academy. Features a full-service spa, an indoor pool and a snack bar/deli. Hilton Garden Inn Annapolis Downtown: Features buffet, a seasonal outdoor pool and complimentary high-speed (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 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.