Beach Hotels & Resorts in Chestertown from NZ$217

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Check availability on Chestertown Beach Hotels

Tonight
5 Apr - 6 Apr
Tomorrow
6 Apr - 7 Apr
Next weekend
10 Apr - 12 Apr
In two weeks
17 Apr - 19 Apr

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
3.5 star property
Chestertown
7.8 out of 10, Good, (77 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 NZ$217
includes taxes & fees
6 Apr - 7 Apr
The Lodge at Great Oak Landing
Exterior

Haven Point Inn and Gallery

Haven Point Inn and Gallery
2.0 star property
Rock Hall
The price is NZ$290
includes taxes & fees
22 Apr - 23 Apr
Haven Point Inn and Gallery
Reception

Kent Island Resort

Kent Island Resort
3.5 star property
Stevensville
9.2 out of 10, Wonderful, (135 reviews)
The price is NZ$276
includes taxes & fees
15 Apr - 16 Apr
Kent Island Resort
Smart TV

Bayside Cottage steps from Rock Hall Harbor

Bayside Cottage steps from Rock Hall Harbor
Rock Hall
10.0 out of 10, Exceptional, (2 reviews)
  • cleanliness
    A blissful beach escape awaits at this modern holiday home, just a short stroll from the shore with complimentary beach towels and bikes.
The price is NZ$630
includes taxes & fees
13 Apr - 14 Apr
Bayside Cottage steps from Rock Hall Harbor
Lobby lounge

Flag House Inn

Flag House Inn
3.5 star property
Historic District
9.2 out of 10, Wonderful, (92 reviews)
The price is NZ$349
includes taxes & fees
6 Apr - 7 Apr
Flag House Inn
Sun-loungers, beach towels

5-bedroom vacation home 5 minutes from historic Charlestown

5-bedroom vacation home 5 minutes from historic Charlestown
Perryville
9.8 out of 10, Exceptional, (148 reviews)
The price is NZ$935
includes taxes & fees
12 Apr - 13 Apr
5-bedroom vacation home 5 minutes from historic Charlestown
Outdoor pool, a heated pool

Waterfront Oasis of Annapolis Star

Waterfront Oasis of Annapolis Star
Annapolis
10.0 out of 10, Exceptional, (81 reviews)
The price is NZ$798
includes taxes & fees
6 Apr - 7 Apr
Waterfront Oasis of Annapolis Star
Exterior detail

Vandiver Inn

Vandiver Inn
3.5 star property
Havre De Grace
9.4 out of 10, Exceptional, (538 reviews)
The price is NZ$238
includes taxes & fees
8 Apr - 9 Apr
Vandiver Inn
On the beach

FLOHOM 14 Luxury Houseboat with Chesapeake Bay Panoramic Views

FLOHOM 14 Luxury Houseboat with Chesapeake Bay Panoramic Views
Pasadena
The price is NZ$743
includes taxes & fees
6 Apr - 7 Apr
FLOHOM 14 Luxury Houseboat with Chesapeake Bay Panoramic Views
Beach

Waterfront Retreat with Private Dock and Beach

Waterfront Retreat with Private Dock and Beach
Worton
10.0 out of 10, Exceptional, (25 reviews)
The price is NZ$549
includes taxes & fees
26 Apr - 27 Apr
Waterfront Retreat with Private Dock and Beach
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

8/10 Good
"Emmy at the front desk was awesome! Appreciated having great hours for breakfast and the pool / hot tub. "The Highway Side" had a lot of charm, and is a good distance below the actually highway. Nice grassy areas for the dogs to sniff. "
Nathan 4-night trip
Posted 1 day ago
Best Western Kent Narrows Inn
Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown

8/10 Good
"The breakfast was as one would expect. Nothing unusual. I wish these hotels wouldn’t use so much plastic. Everything was clean. Chestertown is wonderful. Good restaurants. Much to see. The hotel is not fancy. Just a reliable place to be. Nothing unexpected. All good."
Carol 2-night trip
Posted 2 days ago
Comfort Inn & Suites Chestertown

Frequently asked questions

What is Chestertown like for travellers who love the beach?
Known for its university life, Chestertown offers a lot for the traveller planning a getaway.
What's the best place to stay for a beach holiday 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 holiday in Chestertown?
You can plan your beach trip with this snapshot of year-round temperatures in Chestertown: The hottest months are usually July and August, with an average temperature of 23°C, while the coldest months are January and February, with an average of 4°C. Average annual precipitation for Chestertown is 1232 mm.
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 such as Washington College and Historical Society of Kent County Maryland. For more things to see and do, consider visiting Rolphs Wharf Marina 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 centre. If you'd like to venture out around the area, you may want to rent a car for your trip.