An aerial view of a town with a river, buildings, and surrounding greenery.

Beach Hotels in Chestertown, Maryland

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Check availability on Chestertown Beach Hotels

This weekend
Jul 3 - Jul 5
Next weekend
Jul 10 - Jul 12

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, (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 P8,093
P9,254 total
includes taxes & fees
Jul 9 - Jul 10
The Lodge at Great Oak Landing
In-room safe, desk, soundproofing, rollaway beds

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, (1,002 reviews)
The price is P3,148
P3,526 total
includes taxes & fees
Jul 9 - Jul 10
Super 8 by Wyndham Havre De Grace Aberdeen Area
Aerial view

Kent Island Resort

Kent Island Resort
3.5 star property
Stevensville
9.4 out of 10, Exceptional, (150 reviews)
The price is P10,895
P14,201 total
includes taxes & fees
Jul 6 - Jul 7
Kent Island Resort
Exterior detail

Vandiver Inn

Vandiver Inn
3.5 star property
Havre De Grace
9.4 out of 10, Exceptional, (557 reviews)
The price is P8,864
P9,927 total
includes taxes & fees
Jul 6 - Jul 7
Vandiver Inn
Reception

Village Inn Annapolis MD

Village Inn Annapolis MD
2.0 star property
Annapolis
6.2 out of 10, (508 reviews)
The price is P5,078
P5,788 total
includes taxes & fees
Jul 6 - Jul 7
Village Inn Annapolis MD
Terrace/patio

Fairfield Inn & Suites by Marriott Aberdeen

Fairfield Inn & Suites by Marriott Aberdeen
3.0 star property
Aberdeen
9.0 out of 10, Wonderful, (348 reviews)
The price is P6,716
P7,522 total
includes taxes & fees
Jul 2 - Jul 3
Fairfield Inn & Suites by Marriott Aberdeen
Terrace/patio

Historic Inns of Annapolis

Historic Inns of Annapolis
3.5 star property
Historic District
9.0 out of 10, Wonderful, (1,877 reviews)
The price is P5,531
P8,403 total
includes taxes & fees
Jul 15 - Jul 16
Historic Inns of Annapolis
Free daily continental breakfast

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, (612 reviews)
The price is P5,643
P6,321 total
includes taxes & fees
Jul 6 - Jul 7
Holiday Inn Express Edgewood-Aberdeen-Bel Air by IHG
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, (385 reviews)
The price is P6,100
P6,833 total
includes taxes & fees
Jul 8 - Jul 9
Home2 Suites by Hilton Baltimore / Aberdeen, MD
Lobby

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 P5,742
P6,431 total
includes taxes & fees
Jul 6 - Jul 7
La Quinta Inn & Suites by Wyndham Aberdeen-APG
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

Best Western Kent Narrows Inn

Best Western Kent Narrows Inn

10/10 Excellent
"Gentleman who checked me in was super-friendly and the room was clean and well maintained. Very good value. Low cost. High quality"
Terell 1-night trip
Posted 6 days ago
Best Western Kent Narrows Inn
Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown

8/10 Good
"Comfortable beds. Breakfast was decent, with hot and cold options. Shower did not have pressure. Pool was small but nice. Unfortunately we were there Wednesday -Sunday and never were given new towels or a room cleaning. And the last morning we found ants in the room."
Caroline 1-night trip
Posted 2 weeks 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 Earle Landing 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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