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Find Beach Hotels in Chestertown, MD

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Check availability on Chestertown Beach Hotels

Top Chestertown Beach Hotels

Lobby
Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown

2.5 star property
Chestertown
  • Seasonal outdoor pool
8.6 out of 10, Excellent, (844)
The price is ￥15,649
￥17,371 total
includes taxes & fees
Nov 16 - Nov 17
Comfort Inn & Suites Chestertown
Suite, Multiple Beds, Non Smoking | 1 bedroom, desk, laptop workspace, blackout drapes
Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown

2.0 star property
Chestertown
  • Pet friendly
  • Parking included
  • Free WiFi
  • Air conditioning
  • Laundry
  • Housekeeping
7.2 out of 10, Good, (414)
The price is ￥11,047
￥12,262 total
includes taxes & fees
Nov 30 - Dec 1
Red Roof Inn & Suites Chestertown
Front of property - evening/night
Driftwood Inn

Driftwood Inn

2.0 star property
Chestertown
  • Pet friendly
  • Parking included
  • Free WiFi
  • Air conditioning
  • Housekeeping
  • 24/7 front desk
5.2 out of 10, (174)
Driftwood Inn
Private beach nearby, sun loungers, beach volleyball
The Lodge at Great Oak Landing

The Lodge at Great Oak Landing

3.5 star property
Chestertown
  • Private beach access
  • Beach loungers
  • Seasonal outdoor pool
8.0 out of 10, Very Good, (75)
This waterfront lodge provides a beach paradise with complimentary loungers on sandy shores. After beach volleyball games, guests can retreat to air-conditioned rooms, gather around the firepit, or enjoy meals at the restaurant with drinks from three bars.
The price is ￥15,188
￥17,365 total
includes taxes & fees
Nov 12 - Nov 13
The Lodge at Great Oak Landing
Property grounds
First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown

Chestertown
  • Beach towels
  • Outdoor pool
9.6 out of 10, Exceptional, (105)
The price is ￥15,189
￥24,370 total
includes taxes & fees
Nov 12 - Nov 13
First Floor Studio Apartment in Historic Chestertown
Terrace/patio
Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town

Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town

Chestertown
  • Near the beach
  • Beach towels
9.8 out of 10, Exceptional, (85)
Experience waterfront bliss at this vacation home with a private beach area. Kayak from the dock, unwind on the furnished patio overlooking stunning river views, or gather around the fire pit as eagles soar overhead. The well-equipped kitchen makes vacation dining effortless.
Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town
Outdoor pool
350 Acre Waterfront Farm; High Speed Internet, Pool, Pickleball & Private Dock

350 Acre Waterfront Farm; High Speed Internet, Pool, Pickleball & Private Dock

Chestertown
  • Beach towels
  • Outdoor pool
10.0 out of 10, Exceptional, (61)
350 Acre Waterfront Farm; High Speed Internet, Pool, Pickleball & Private Dock
Exterior
Beautiful, spacious waterfront home, an easy walk to historic Chestertown

Beautiful, spacious waterfront home, an easy walk to historic Chestertown

Chestertown
  • Beach towels
9.8 out of 10, Exceptional, (23)
Beautiful, spacious waterfront home, an easy walk to historic Chestertown
Exterior
Contemporary waterfront house with private dock & kayaks!

Contemporary waterfront house with private dock & kayaks!

Chestertown
  • Beach loungers
10.0 out of 10, Exceptional, (66)
Contemporary waterfront house with private dock & kayaks!
Fridge, microwave, oven, stovetop
Country Estate in Historic District

Country Estate in Historic District

Chestertown
  • Beach loungers
10.0 out of 10, Exceptional, (70)
Journey between relaxation zones at this coastal haven. The private beach club offers exclusive shoreline access via convenient shuttle service. Return to a comfortable retreat with modern amenities, perfect for unwinding after days filled with sand and sunshine.
Country Estate in Historic District
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 Chestertown Hotel Reviews

Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown

10/10 Excellent
"Large clean room. Bed firm "
Elaine 1-night trip
Posted 3 days ago
Comfort Inn & Suites Chestertown

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Frequently asked questions

What is Chestertown like for travelers who love the beach?
Known for its university life, Chestertown offers a lot for the traveler planning a getaway.
What's the best hotel for a beach vacation in Chestertown?
The Lodge at Great Oak Landing is a top lodge with a seasonal outdoor pool and 3 bars/lounges, and it's located near a private beach.
When's the best time for a beach vacation in Chestertown?
You can plan your beach trip with this snapshot of the seasons in Chestertown: The hottest months are usually July and August with an average temp of 74°F, while the coldest months are January and February with an average of 39°F. Average annual precipitation for Chestertown is 48 inches.
What is there to see and do around Chestertown?
After arriving and checking into your hotel, you'll probably want to explore your surroundings. Beach lovers can head straight to Betterton Beach or Main Beach for some quality time by the water. Experience the area's university life, and make time for local attractions like Washington College and River Arts Chestertown. For more things to see and do, consider visiting Historical Society of Kent County Maryland or Rolphs Wharf Marina.
What's the best way to get to my beach hotel in Chestertown?
Here's some information to help you get to and around your beach accommodation in Chestertown more easily: To get to Chestertown, book a flight to Baltimore, MD (MTN-Martin State), the closest major airport, which is located 20.3 mi (32.7 km) from the city center. If you'd like to venture out around the area, you may want a rental car for your journey.