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Find Hotels with a Pool in Chester, MD

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Top Chester Hotels with a Pool

Knapps Narrows Marina & Inn
3.0 star property
  • Pool
  • Breakfast included
  • Parking included
  • Free WiFi
  • Air conditioning
  • Laundry
9.4 out of 10, Exceptional, (347)
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 AED 367
AED 404 total
includes taxes & fees
3 Nov - 4 Nov
Knapps Narrows Marina & Inn
St Michaels Inn
2.5 star property
  • Pool loungers
8.2 out of 10, Very Good, (1004)
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 AED 366
AED 402 total
includes taxes & fees
6 Nov - 7 Nov
St Michaels Inn
Holiday Inn Express Annapolis East-Kent Island by IHG
2.5 star property
  • Pool loungers
9.2 out of 10, Wonderful, (913)
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 AED 290
AED 322 total
includes taxes & fees
3 Dec - 4 Dec
Holiday Inn Express Annapolis East-Kent Island by IHG
Hilton Garden Inn Annapolis
3.0 star property
  • Outdoor pool
8.2 out of 10, Very Good, (1002)
Sparkling waters beckon at the well-maintained outdoor pool, a highlight praised by guests for its cleanliness and welcoming atmosphere. After swimming, visitors can energize at the 24-hour fitness center or dine at the Garden Grille and Bar.
The price is AED 263
AED 300 total
includes taxes & fees
16 Nov - 17 Nov
Hilton Garden Inn Annapolis
Quality Inn
2.5 star property
  • Pool
  • Breakfast included
  • Pet friendly
  • Parking included
  • Free WiFi
  • Air conditioning
7.6 out of 10, Good, (808)
Poolside relaxation awaits after exploring the city center 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 AED 312
AED 343 total
includes taxes & fees
9 Nov - 10 Nov
Quality Inn
Best Western Kent Narrows Inn
2.5 star property
  • Indoor pool
  • Hot tub
8.0 out of 10, Very Good, (1003)
Sparkling waters await in the pristine indoor swimming pool, complemented by a rejuvenating hot tub and sauna. Active travelers appreciate the nearby hiking trails while enjoying spotless accommodations with 49-inch TVs and refrigerators.
The price is AED 338
AED 375 total
includes taxes & fees
16 Nov - 17 Nov
Best Western Kent Narrows Inn
Wylder Tilghman Island
2.0 star property
  • On private beach
8.8 out of 10, Excellent, (87)
Seasonal outdoor swimming beckons travelers 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 AED 512
AED 724 total
includes taxes & fees
2 Dec - 3 Dec
Wylder Tilghman Island
Quality Inn
2.5 star property
  • Pool
  • Breakfast included
  • Parking included
  • Free WiFi
  • Air conditioning
  • Business services
7.8 out of 10, Good, (847)
Cooling waters await at the seasonal outdoor pool, open 24 hours from May to October. This hotel sits near the Chesapeake Exploration Center, offering comfortable rooms, a complimentary breakfast buffet, and friendly service praised by past guests.
The price is AED 353
AED 392 total
includes taxes & fees
6 Nov - 7 Nov
Quality Inn
Crowne Plaza Annapolis by IHG
3.5 star property
  • Indoor pool
8.8 out of 10, Excellent, (1016)
Swimming enthusiasts revel in the refreshing indoor pool at this Annapolis hotel, complemented by a 24-hour fitness center. Positioned near Westfield Annapolis Mall, guests appreciate the convenient restaurant, bar, and thoughtful amenities like free parking.
The price is AED 356
AED 406 total
includes taxes & fees
24 Nov - 25 Nov
Crowne Plaza Annapolis by IHG
The Inn at Chesapeake Bay Beach Club
4.0 star property
  • Full-service spa
9.4 out of 10, Exceptional, (423)
Seasonal outdoor pool beckons from May to September amid upscale amenities at this Chesapeake Bay hotel. Professional staff complement the experience with nearby dining options, complimentary bicycles, and rejuvenating spa treatments.
The price is AED 680
AED 848 total
includes taxes & fees
1 Dec - 2 Dec
The Inn at Chesapeake Bay Beach Club
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.

Top Chester Hotel Reviews

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Frequently asked questions

What are some hotels with pools in Chester?
Historic Inns of Annapolis: Provides buffet, an indoor pool, and free self parking. Graduate by Hilton Annapolis: Features buffet, a seasonal outdoor pool, and complimentary wireless internet access. Country Inn & Suites by Radisson, Annapolis, MD: Hotel located near U.S. Naval Academy. Features 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. DoubleTree by Hilton Hotel Annapolis: Offers 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 Matapeake State Park, Chesapeake Bay Environmental Center, 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 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.