Hotels with Swimming Pool in Chester, Maryland

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Check availability on Chester Hotels with Swimming Pool

Tonight
Apr 7 - Apr 8
Tomorrow
Apr 8 - Apr 9
This weekend
Apr 10 - Apr 12
Next weekend
Apr 17 - Apr 19

Our top choices for Chester hotels with a pool

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, (1,001 reviews)
  • cleanliness
    Make a splash at this family-friendly hotel with an indoor pool that welcomes guests year-round.
The price is P6,543
P7,197 total
includes taxes & fees
Apr 8 - Apr 9
Best Western Plus Easton Inn & Suites
Aerial view

Kent Island Resort

Kent Island Resort
3.5 star property
Stevensville
9.2 out of 10, Wonderful, (135 reviews)
  • cleanliness
    Victorian pool retreat with sun loungers and umbrellas by Chesapeake Bay Bridge.
The price is P6,891
P9,456 total
includes taxes & fees
Apr 16 - Apr 17
Kent Island Resort
Seasonal outdoor pool

Quality Inn

Quality Inn
2.5 star property
Easton
7.6 out of 10, Good, (854 reviews)
  • cleanliness
    Dive into summer bliss at this quality hotel featuring a seasonal outdoor pool and fitness center.
The price is P4,847
P5,332 total
includes taxes & fees
Apr 21 - Apr 22
Quality 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, (1,001 reviews)
  • cleanliness
    Aquatic bliss awaits at this central hotel, with a rejuvenating indoor pool and hot tub sanctuary.
The price is P5,962
P6,617 total
includes taxes & fees
Apr 20 - Apr 21
Best Western Kent Narrows 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, (888 reviews)
  • cleanliness
    Take a dip anytime, day or night, in this hotel's seasonal outdoor pool near Chesapeake Bay.
The price is P5,867
P6,512 total
includes taxes & fees
Apr 13 - Apr 14
Quality Inn Grasonville near Kent Island
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, (478 reviews)
  • cleanliness
    Pool paradise meets scenic marina views for a refreshing escape on the water.
The price is P9,130
P10,408 total
includes taxes & fees
Apr 8 - Apr 9
Anchored Inn at Hidden Harbour Marina
Seasonal outdoor pool

Wylder Tilghman Island

Wylder Tilghman Island
2.0 star property
Tilghman
8.8 out of 10, Excellent, (94 reviews)
  • cleanliness
    Riverside relaxation awaits with a seasonal outdoor pool, private beach, and sauna.
The price is P7,347
P10,723 total
includes taxes & fees
Apr 27 - Apr 28
Wylder Tilghman Island
Seasonal outdoor pool

Knapps Narrows Marina & Inn

Knapps Narrows Marina & Inn
3.0 star property
Sherwood
9.4 out of 10, Exceptional, (377 reviews)
  • cleanliness
    Seaside swimming haven at marina hotel offers poolside relaxation and boat adventures.
The price is P9,004
P9,904 total
includes taxes & fees
Apr 8 - Apr 9
Knapps Narrows Marina & Inn
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, (980 reviews)
  • cleanliness
    Splashy pool escapes by the bay; seasonal swimming paradise with sun-soaked loungers.
The price is P7,443
P8,262 total
includes taxes & fees
Apr 8 - Apr 9
Holiday Inn Express Annapolis East-Kent Island by IHG
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)
  • cleanliness
    Seasonal outdoor pool retreat with plush loungers makes summer days in St. Michaels extra delightful.
The price is P8,121
P8,933 total
includes taxes & fees
Apr 8 - Apr 9
St Michaels 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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Choose what matters most at hotels with a pool in Chester

Breakfast included
4 stars

Top Chester Hotel Reviews

Sonesta ES Suites Annapolis

Sonesta ES Suites Annapolis

10/10 Excellent
"Super spacious and clean. Would stay again"
Quiana 2-night trip
Posted 4 hours ago
Sonesta ES Suites Annapolis

Frequently asked questions

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