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Beachfront Hotels in Chestertown

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Featured Chestertown Beach Hotels

Comfort Inn & Suites Chestertown
Comfort Inn & Suites Chestertown
2.5 out of 5
150 Scheeler Road, Chestertown, MD
Fully refundableReserve now, pay when you stay
Book a stay at this business-friendly hotel in Chestertown. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
Comfort Inn & Suites Chestertown
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.

Hotels with Pools in Chestertown

Comfort Inn & Suites Chestertown
Comfort Inn & Suites Chestertown
2.5 out of 5
150 Scheeler Road, Chestertown, MD
Book a stay at this business-friendly hotel in Chestertown. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
8.4/10 Very Good! (734 reviews)
Nice hotel
"Front desk staff was welcoming and friendly. We had a suite so I am guessing it was a bit larger than a regular room but it was really wonderful to have the extra space. The room was clean and the breakfast was decent (the coffee was good for hotel coffee). Would certainly stay here again when I ..."

Reviewed on Dec 13, 2024

Comfort Inn & Suites Chestertown
Red Roof Inn & Suites Chestertown
Red Roof Inn & Suites Chestertown
2 out of 5
160 Scheeler Rd, Chestertown, MD
Stay at this hotel in Chestertown. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff in our reviews.
7.2/10 Good! (322 reviews)
Nice but no breakfast
"Comfortable room and fair price for the room size. Very clean. Bathroom was nice but had a broken wall mounted hair dryer and the bathroom door did not latch closed so it stayed open about an inch. Front desk was businesslike but not the least bit friendly. There is no breakfast or even coffee offered. ..."

Reviewed on Nov 10, 2024

Red Roof Inn & Suites Chestertown
Driftwood Inn
Driftwood Inn
2 out of 5
609 Washington Avenue, Chestertown, MD
Stay at this motel in Chestertown. Enjoy free WiFi, free parking, and a 24-hour front desk.
5/10 (167 reviews)
"Rooms were clean. Check-in was a breeze, and the housekeeping lady is the best left her a nice tip"

Reviewed on Oct 16, 2024

Driftwood 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.

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:

  • 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.

  • 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.

  • 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.