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Find beach hotels in Chestertown, MD from CA $85

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Check availability on Chestertown Beach Hotel

Tonight
Sep 20 - Sep 21
Tomorrow
Sep 21 - Sep 22
Next weekend
Sep 25 - Sep 27
In two weeks
Oct 2 - Oct 4

Our top choices for Chestertown beach hotels

1. The Lodge at Great Oak Landing

The Lodge at Great Oak Landing
Chestertown
  • Escape to waterfront tranquility with a private beach just 0.25 miles away, where sandy shores, volleyball courts, and loungers await.
CA $151
CA $173 total
includes taxes & fees
Sep 23 - Sep 24
The Lodge at Great Oak Landing

2. Waterfront Retreat with Private Dock and Beach

Waterfront Retreat with Private Dock and Beach
Worton
CA $245
CA $439 total
includes taxes & fees
Oct 4 - Oct 5
Waterfront Retreat with Private Dock and Beach

3. Home2 Suites by Hilton Baltimore / Aberdeen, MD

Home2 Suites by Hilton Baltimore / Aberdeen, MD
Aberdeen
CA $136
CA $153 total
includes taxes & fees
Oct 4 - Oct 5
Home2 Suites by Hilton Baltimore / Aberdeen, MD

4. Hampton Inn & Suites Edgewood/Aberdeen-South

Hampton Inn & Suites Edgewood/Aberdeen-South
Edgewood
CA $118
CA $132 total
includes taxes & fees
Sep 29 - Sep 30
Hampton Inn & Suites Edgewood/Aberdeen-South

5. Holiday Inn Express Edgewood-Aberdeen-Bel Air by IHG

Holiday Inn Express Edgewood-Aberdeen-Bel Air by IHG
Edgewood
CA $123
CA $138 total
includes taxes & fees
Sep 24 - Sep 25
Holiday Inn Express Edgewood-Aberdeen-Bel Air by IHG

6. La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A

La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A
Edgewood
CA $111
CA $124 total
includes taxes & fees
Sep 22 - Sep 23
La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A

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

Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD
Bel Air
CA $125
CA $140 total
includes taxes & fees
Sep 27 - Sep 28
Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD

8. Ramada Hotel & Conference Center by Wyndham Edgewood

Ramada Hotel & Conference Center by Wyndham Edgewood
Edgewood
CA $118
CA $132 total
includes taxes & fees
Sep 22 - Sep 23
Ramada Hotel & Conference Center by Wyndham Edgewood

9. Super 8 by Wyndham Havre De Grace Aberdeen Area

Super 8 by Wyndham Havre De Grace Aberdeen Area
Havre De Grace
CA $76
CA $85 total
includes taxes & fees
Sep 23 - Sep 24
Super 8 by Wyndham Havre De Grace Aberdeen Area

10. Days Inn by Wyndham Aberdeen

Days Inn by Wyndham Aberdeen
Aberdeen
CA $106
CA $119 total
includes taxes & fees
Sep 27 - Sep 28
Days Inn by Wyndham Aberdeen
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Choose what matters most at beach hotels in Chestertown

Pool
Breakfast included
4 stars
5 stars
All-inclusive

Find out more about Chestertown

Chestertown and its attractions for beach lovers

Located just a short drive from the serene beaches of the Chesapeake Bay, Chestertown, Maryland, offers a delightful blend of charm and coastal adventure for families seeking quality experiences. Start your exploration at Wilmer Park, where the scenic waterfront beckons with picnic spots and walking trails, perfect for a leisurely afternoon with the family. Just a stone’s throw away, the Chestertown Marina invites visitors to enjoy kayaking or paddleboarding, providing a unique perspective of the town from the water. Art enthusiasts can visit the nearby Kent County Arts Council, which showcases local talents and often hosts family-friendly workshops. For a taste of local history, the Custom House Museum offers engaging exhibits that delve into the town's rich maritime heritage. After a day of exploration, families can unwind at hotels along the waterfront, where attentive service and comfortable accommodations ensure a relaxing stay. Opt for a hotel with easy access to the beach, allowing for spontaneous beach outings, while also enjoying the quaint atmosphere of Chestertown’s historic streets, lined with boutique shops and delightful eateries.

Find the best beach hotels and resorts in Chestertown

For those seeking a beach getaway in Chestertown, Maryland, these hotels offer the perfect blend of comfort and coastal charm. Enjoy sun-soaked days and stunning views at these delightful properties.The Lodge at Great Oak Landing

  • Why it's great for the ultimate beach vacation spot: The Lodge at Great Oak Landing is an ideal retreat for beach lovers, a solid guest review rating of 8.2. Guests can enjoy direct access to a private sand beach, perfect for sunbathing and relaxation. With a variety of beach amenities including sun loungers, a waterfront location, and volleyball courts, it promises a fun-filled coastal experience.
  • Other amenities: This hotel features a shared pool with sun loungers and umbrellas, ensuring ample relaxation options. Active guests can take advantage of the 24-hour fitness facilities, while families will appreciate the playground. Additional conveniences include self-parking options, a mini-refrigerator in rooms, and stunning marina views to enjoy during your stay.
  • Nearby attractions: Kinnairds Point Drive - 19.6 km, Still Pond Station Park - 24.5 km

Top Chestertown Hotel Reviews

Hilton Garden Inn Kent Island Marina

Hilton Garden Inn Kent Island Marina

8/10 Good
"No free breakfast but the one I had to pay for was good"
Darlene 1-night trip
Posted 2 days ago
Hilton Garden Inn Kent Island Marina
Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown

10/10 Excellent
"I have stayed at this location a number of times and have been very pleased with my experience each time. Friendly staff, breakfast is good, and I had a chance to use the workout room this time. Very nice as well. I will be returning again soon."
Robert 2-night trip
Posted 2 days 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 2 restaurants and a seasonal outdoor pool, and it's located near a private beach. Great Oak Manor is another good option to stay near the 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 Chestertown Historic District.
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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