Find Beach Hotels in Chestertown, MD

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Check availability on Chestertown Beach Hotels

This weekend
Jun 5 - Jun 7
Next weekend
Jun 12 - Jun 14

Our top choices for Chestertown beach hotels

Private beach nearby, sun loungers, beach volleyball

The Lodge at Great Oak Landing

The Lodge at Great Oak Landing
3.0 star property
Chestertown
7.8 out of 10, Good, (83 reviews)
  • cleanliness
    Escape to waterfront tranquility with a private beach just 0.25 miles away, where sandy shores, volleyball courts, and loungers await.
The price is ￥21,071
￥24,092 total
includes taxes & fees
Jun 4 - Jun 5
The Lodge at Great Oak Landing
Property amenity

Super 8 by Wyndham Havre De Grace Aberdeen Area

Super 8 by Wyndham Havre De Grace Aberdeen Area
2.0 star property
Havre De Grace
6.6 out of 10, (994 reviews)
The price is ￥8,726
￥9,774 total
includes taxes & fees
Jun 4 - Jun 5
Super 8 by Wyndham Havre De Grace Aberdeen Area
Reception

Kent Island Resort

Kent Island Resort
3.5 star property
Stevensville
9.2 out of 10, Wonderful, (141 reviews)
The price is ￥24,839
￥32,971 total
includes taxes & fees
Jun 16 - Jun 17
Kent Island Resort
Exterior

Haven Point Inn and Gallery

Haven Point Inn and Gallery
2.0 star property
Rock Hall
10.0 out of 10, Exceptional, (1 review)
The price is ￥21,551
￥23,922 total
includes taxes & fees
Jun 10 - Jun 11
Haven Point Inn and Gallery
Exterior detail

Vandiver Inn

Vandiver Inn
3.5 star property
Havre De Grace
9.4 out of 10, Exceptional, (547 reviews)
The price is ￥23,014
￥25,776 total
includes taxes & fees
Jun 4 - Jun 5
Vandiver Inn
Exterior

La Quinta Inn & Suites by Wyndham Aberdeen-APG

La Quinta Inn & Suites by Wyndham Aberdeen-APG
3.0 star property
Aberdeen
9.0 out of 10, Wonderful, (1,005 reviews)
The price is ￥14,079
￥15,769 total
includes taxes & fees
Jun 15 - Jun 16
La Quinta Inn & Suites by Wyndham Aberdeen-APG
Combined shower/tub, free toiletries, hair dryer, towels

Ramada Hotel & Conference Center by Wyndham Edgewood

Ramada Hotel & Conference Center by Wyndham Edgewood
2.0 star property
Edgewood
6.6 out of 10, (530 reviews)
The price is ￥10,631
￥11,907 total
includes taxes & fees
Jun 2 - Jun 3
Ramada Hotel & Conference Center by Wyndham Edgewood
Terrace/patio

Home2 Suites by Hilton Baltimore / Aberdeen, MD

Home2 Suites by Hilton Baltimore / Aberdeen, MD
3.0 star property
Aberdeen
8.8 out of 10, Excellent, (379 reviews)
The price is ￥15,542
￥17,406 total
includes taxes & fees
Jun 14 - Jun 15
Home2 Suites by Hilton Baltimore / Aberdeen, MD
Exterior

134 Prince - Luxury Boutique Hotel

134 Prince - Luxury Boutique Hotel
2.5 star property
Annapolis
9.8 out of 10, Exceptional, (37 reviews)
The price is ￥30,897
￥35,222 total
includes taxes & fees
Jun 2 - Jun 3
134 Prince - Luxury Boutique Hotel
Terrace/patio

Holiday Inn Express Aberdeen by IHG

Holiday Inn Express Aberdeen by IHG
2.5 star property
Aberdeen
8.6 out of 10, Excellent, (448 reviews)
The price is ￥20,546
￥23,010 total
includes taxes & fees
Jun 2 - Jun 3
Holiday Inn Express Aberdeen by IHG
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 beach hotels in Chestertown

Pool
Breakfast included

Top Chestertown Hotel Reviews

Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown

4/10 Poor
"I stayed here for 5 days and 4 nights housekeeping did not check my room once I never got new towels trash was never collected even when there was 2 adults and 3 kids in one room. Also The water pressure was not the best"
Mia 4-night trip
Posted less than an hour ago
Comfort Inn & Suites Chestertown

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 free WiFi, 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 Chestertown Historic District or Northern Chesapeake Bay.
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.