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Featured Chestertown Beach Hotels
Hotels with Pools in Chestertown
Reviewed on Dec 13, 2024
Reviewed on Nov 10, 2024
Reviewed on Oct 16, 2024
Beach Hotels Chestertown
Toes in the sand, drink in hand, skin getting tanned—beach life is the sweet life. At the shore, the pace slows, moods elevate, and beachfront hotels line the horizon. Whether you’re a jump-straight-in-the-water person or like to remain on dry land, you’re living your best life at the beach. Better yet, get cozy at beach hotels Chestertown after the day’s surf-and-sand activities for some post-sunset chilling.
Vacation + beach = perfection
The best things come to those who beach. Find watersports like surfing, snorkeling, waterskiing, paddle boarding, kayaking—options are aplenty for enjoying the waves. Feel like taking it easy? Nothing’s better than napping under an umbrella and taking in the sounds of the surf. Bring a kite, enjoy a round of spike ball, or get competitive over a volleyball match. It’s easy to check all the boxes on beach days. The best beach hotels in Chestertown can point you toward delicious food and other activities in the area. And they likely have enough on-site amenities that you’ll never have to venture far from shore.
She saves (sand) dollars by the seashore
If you think you can’t beat a good day at the beach, add the best prices to the equation, and you’ve found the right formula for the best time ever. Filter hotels by the following to make one and one equal amazing:
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Hotwire Hot Rates: With a Hotwire Hot Rate, you’ll think you found the mecca of cheap beach hotels. In reality, you’re seeing some of the best discounts on premium hotels, because mystery deals really pay off. You may even end up in the best luxury beach hotel at an incredible price.
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Price: If the beach is enough to make you swoon, look for the lowest price on hotels, with ours starting at $70. If you’ve set your sights a little higher, up those price points for a swankier stay.
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Amenities: You came for the beach, but extra perks don’t hurt. Get straight to the waves and grab a free breakfast. Relax even more at a full-service spa. When it comes to a tailor-made getaway, finding the right amenities ups the experience to the power of perfect.
Subtract stress, add a sprinkle of sun and sand, and enjoy the sum total of your days at the beach. When you book with Hotwire, your vacation satisfaction can reach 100 percent.
Hotels by Star Rating
Top Oceanfront Hotel Destinations
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More Hotel Options in Chestertown
- Hotels with Free Parking in Chestertown
- Romantic Hotels in Chestertown
- Family Hotels in Chestertown
- Pet-friendly Hotels in Chestertown
- Hotels with a Pool in Chestertown
- Apartment Hotel in Chestertown
- Historic Hotels in Chestertown
- Hotel Wedding Venues in Chestertown
- Hotels with an Indoor Pool in Chestertown
- Resorts & Hotels with Spas in Chestertown
Top Points of Interests in Chestertown
- Hotels near Washington College
- Hotels near Rolphs Wharf Marina
- Hotels near River Arts Chestertown
- Hotels near Garfield Center for the Arts at the Prince Theater
- Hotels near Historical Society of Kent County Maryland
- Hotels near Crumpton Auction
- Hotels near Wilmer Park
- Hotels near Baltimore Cruise Terminal
- Hotels near U.S. Naval Academy
- Hotels near Navy-Marine Corps Memorial Stadium
- Hotels near Ripken Stadium
- Hotels near Chesapeake Bay Bridge
- Hotels near Annapolis City Dock
- Hotels near Sandy Point State Park
- Hotels near Susquehanna River
- Hotels near Harford Community College
- Hotels near White Marsh Mall
- Hotels near Fort McHenry
- Hotels near Cedar Lane Regional Park
- Hotels near Maryland State House
Cities near Chestertown
- Annapolis Hotels (28.1 mi)
- Dover Hotels (29.45 mi)
- Edgewood Hotels (18.31 mi)
- Havre De Grace Hotels (22.85 mi)
- St. Michaels Hotels (30.99 mi)
- Perryville Hotels (23.56 mi)
- Aberdeen Hotels (20.7 mi)
- Grasonville Hotels (19.53 mi)
- Glen Burnie Hotels (29.99 mi)
- Easton Hotels (30.7 mi)
- Bel Air Hotels (26.49 mi)
- White Marsh Hotels (21.43 mi)
- Elkton Hotels (29.71 mi)
- Middletown Hotels (24.66 mi)
- Delaware Beaches Hotels (43.94 mi)
- Appalachian Mountains Hotels (181.58 mi)
Car Rentals near Chestertown
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Popular Beach Hotel Destinations
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Top Booked Hotels in Chestertown
- Comfort Inn & Suites Chestertown
- Sagamore Pendry Baltimore
- Historic Inns of Annapolis
- Quality Inn & Suites Bel Air I-95 Exit 77A
- Hampton Inn Baltimore/Glen Burnie
- La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A
- Best Western Plus Hotel & Conference Center
- La Quinta Inn & Suites by Wyndham Baltimore S. Glen Burnie
- Annapolis Waterfront Hotel, Autograph Collection
- Hampton Inn Baltimore Bayview Campus
- Fairfield Inn & Suites by Marriott White Marsh