Find Beach Hotels in Chestertown, MD

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Check availability on Chestertown Beach Hotels

Our top choices for Chestertown beach hotels

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Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown
2.5 star property
Chestertown
8.6 out of 10, Excellent, (859)
"The room was a great size and very clean. The staff were very accommodating and friendly. The amenities were very good. We would definitely recommend this hotel. "
United States
Santa
The price is AED 377
AED 419 total
includes taxes & fees
18 Dec - 19 Dec
Comfort Inn & Suites Chestertown
Suite, Multiple Beds, Non Smoking | Desk, laptop workspace, blackout drapes, iron/ironing board
Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown
2.0 star property
Chestertown
7.2 out of 10, Good, (420)
"Professional staff, warm greetings clean room "
United States
Dr. Nicholas and Mrs. Karen
The price is AED 264
AED 294 total
includes taxes & fees
18 Dec - 19 Dec
Red Roof Inn & Suites Chestertown
Front of property - evening/night
Driftwood Inn

Driftwood Inn

Driftwood Inn
2.0 star property
Chestertown
5.2 out of 10, (175)
"Rooms are clean, staf was helpful "
United States
Daryl
The price is AED 233
AED 259 total
includes taxes & fees
24 Dec - 25 Dec
Driftwood Inn
Private beach nearby, sun loungers, beach volleyball
The Lodge at Great Oak Landing

The Lodge at Great Oak Landing

The Lodge at Great Oak Landing
3.5 star property
Chestertown
7.8 out of 10, Good, (77)
"Very nice rooms, "
United States
Stephania
The price is AED 364
AED 416 total
includes taxes & fees
15 Dec - 16 Dec
The Lodge at Great Oak Landing
Property grounds
First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown
Chestertown
9.6 out of 10, Exceptional, (108)
"Amazing and neat and very private "
United States
Alexander M.
The price is AED 364
AED 583 total
includes taxes & fees
15 Dec - 16 Dec
First Floor Studio Apartment in Historic Chestertown
Outdoor pool
350 Acre Waterfront Farm; High Speed Internet, Pool, Pickleball & Private Dock

350 Acre Waterfront Farm; High Speed Internet, Pool, Pickleball & Private Dock

350 Acre Waterfront Farm; High Speed Internet, Pool, Pickleball & Private Dock
Chestertown
10.0 out of 10, Exceptional, (61)
"Great!"
United States
Shaama P.
350 Acre Waterfront Farm; High Speed Internet, Pool, Pickleball & Private Dock
Exterior
Beautiful, spacious waterfront home, an easy walk to historic Chestertown

Beautiful, spacious waterfront home, an easy walk to historic Chestertown

Beautiful, spacious waterfront home, an easy walk to historic Chestertown
Chestertown
9.8 out of 10, Exceptional, (23)
"We had a great time"
United States
Harold L.
Beautiful, spacious waterfront home, an easy walk to historic Chestertown
Terrace/patio
Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town

Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town

Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town
Chestertown
9.8 out of 10, Exceptional, (85)
"Everything we needed was there. Owners next sore are super nice and hrphful."
United States
steven s.
Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town
Fridge, microwave, oven, stovetop
Country Estate in Historic District

Country Estate in Historic District

Country Estate in Historic District
Chestertown
10.0 out of 10, Exceptional, (70)
"Great hosts, location, gardens, and overallstay! "
United States
Robin G.
Country Estate in Historic District
Exterior
Contemporary waterfront house with private dock & kayaks!

Contemporary waterfront house with private dock & kayaks!

Contemporary waterfront house with private dock & kayaks!
Chestertown
10.0 out of 10, Exceptional, (66)
"It was super peaceful and relaxing. We fished and read and spent the week decompressing and absolutely loved the area!"
United States
Roni L.
Contemporary waterfront house with private dock & kayaks!
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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Top Chestertown Hotel Reviews

Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown

10/10 Excellent
"Everything was well!"
Ahmed 1-night trip
Posted 12 hours ago
Comfort Inn & Suites Chestertown

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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 3 bars/lounges, 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 Historical Society of Kent County Maryland. 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.