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Our top choices for Chestertown beach hotels

The Lodge at Great Oak Landing

The Lodge at Great Oak Landing
3.0 star property
Chestertown
7.8 out of 10, Good, (89 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 NT$4,226
NT$4,832 total
includes taxes & fees
Jul 6 - Jul 7
The Lodge at Great Oak Landing

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, (1,001 reviews)
The price is NT$1,644
NT$1,841 total
includes taxes & fees
Jul 8 - Jul 9
Super 8 by Wyndham Havre De Grace Aberdeen Area

Kent Island Resort

Kent Island Resort
3.5 star property
Stevensville
9.4 out of 10, Exceptional, (152 reviews)
The price is NT$5,215
NT$6,877 total
includes taxes & fees
Jul 13 - Jul 14
Kent Island Resort

Vandiver Inn

Vandiver Inn
3.5 star property
Havre De Grace
9.4 out of 10, Exceptional, (558 reviews)
The price is NT$4,616
NT$5,170 total
includes taxes & fees
Jul 6 - Jul 7
Vandiver Inn

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, (1,001 reviews)
The price is NT$2,990
NT$3,349 total
includes taxes & fees
Jul 6 - Jul 7
La Quinta Inn & Suites by Wyndham Aberdeen-APG

Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD

Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD
3.0 star property
Bel Air
8.8 out of 10, Excellent, (1,001 reviews)
The price is NT$3,278
NT$3,671 total
includes taxes & fees
Aug 2 - Aug 3
Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD

Village Inn Annapolis MD

Village Inn Annapolis MD
2.0 star property
Annapolis
6.2 out of 10, (509 reviews)
The price is NT$2,652
NT$3,023 total
includes taxes & fees
Jul 6 - Jul 7
Village Inn Annapolis MD

Historic Inns of Annapolis

Historic Inns of Annapolis
3.5 star property
Historic District
9.0 out of 10, Wonderful, (1,870 reviews)
The price is NT$2,880
NT$4,376 total
includes taxes & fees
Jul 12 - Jul 13
Historic Inns of Annapolis

Fairfield Inn & Suites by Marriott Aberdeen

Fairfield Inn & Suites by Marriott Aberdeen
3.0 star property
Aberdeen
9.0 out of 10, Wonderful, (349 reviews)
The price is NT$3,497
NT$3,917 total
includes taxes & fees
Aug 2 - Aug 3
Fairfield Inn & Suites by Marriott Aberdeen

Holiday Inn Express Edgewood-Aberdeen-Bel Air by IHG

Holiday Inn Express Edgewood-Aberdeen-Bel Air by IHG
2.5 star property
Edgewood
9.0 out of 10, Wonderful, (613 reviews)
The price is NT$3,195
NT$3,578 total
includes taxes & fees
Jul 14 - Jul 15
Holiday Inn Express Edgewood-Aberdeen-Bel Air 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.

Choose what matters most at beach hotels in Chestertown

Top Chestertown Hotel Reviews

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 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.

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