62+ Hotel & Resort Deals in Chestertown |
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Chestertown Hotels, Resorts, and Rentals

About Chestertown Vacation Rentals

There are more than 62 places to stay in Chestertown that are available. These options include hotels, resorts, rentals as well as short-term private accommodations (i.e. RVs, Condos, Cabins, Chalets, etc.). The places can provide you with a great option on your next holiday. Compare many places to stay in Chestertown.

Are you seeking a last-minute hotel deal, or are you wanting to find the best deals available for hotels, resorts, cottages, condos, private villas, chalets, or a large vacation homes? With Hotala Chestertown, you can quickly compare different options to find the hottest deals with a single click. Looking for a resort with an infinity pool, hot tub, is pet-friendly, or features a large master suite bedrooms or has a fireplace? You can find hotels, resorts, or other popular Airbnb-style properties in or near Chestertown. Places to stay near Chestertown are 950.72 ft² on average, with prices averaging US $536 a night.

Hotala makes it easy to find and compare hotels, resorts, and holiday rentals in Chestertown with prices often listed at a 30-40% off the rack rate. Just enter your destination and secure your reservation today.

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Top Hotels, Resorts, Rentals, Villas, Vacation Homes, Cottages, B&B and Cabins Accommodation Types in Chestertown

Type Count
Vacation Homes 40
Holiday Apartments 9
Cottages 3
Cabin Rentals 2
Others 2
B&B 1

Use these Quick Filters to Find a Vacation Rental in Chestertown

★ Pro Tip: Hotala has aggregated the supply of many of the leading websites including providers of short-term rentals, OTAs (including Booking.com, Agoda, Airbnb, and others). Use the Advanced Filter feature at the top to compare homes, hotels, vacation rentals, bed and breakfasts, private Airbnb-style rentals, eco-friendly properties, and more. We want to help you find the hottest places and best places to stay in Chestertown.

Weather in Chestertown, MD

View the weather forecast for Chestertown before booking your Chestertown Vacation Rentals to confirm your best time to go.

December - February
High 56°F       Low 33°F
March - May
High 73°F       Low 38°F
June - August
High 90°F       Low 69°F
September - November
High 80°F       Low 42°F

Stay Near Chestertown's Top Attractions

Hotala can help you find hotels, resorts, and rentals near many of Chestertown's top attractions, neighborhoods, and points of interest.


Washington College
Wilmer Park
Rolphs Wharf Marina
Historical Society of Kent County Maryland
River Arts Chestertown
Garfield Center for the Arts at the Prince Theater
U.S. Naval Academy
Ripken Stadium
White Marsh Mall
Chesapeake Bay Bridge
Fort McHenry
Sandy Point State Park
Canton Waterfront Park
Queenstown Premium Outlets
Annapolis Maritime Museum
Queenstown Harbor Golf Club
Liriodendron Mansion
Havre de Grace Promenade
Bay Hills Golf Club
Maryland World War II Memorial

Find Hotels, Resorts, and Rentals Nearby in these Cities & Neighborhoods


Great Oak Landing 147 Properties
Kent County 137 Properties
Georgetown 137 Properties
Tolchester Beach 66 Properties
Pomona 48 Properties
Fairlee 43 Properties
Wilmer Park 40 Properties
River Arts Chestertown 40 Properties
Garfield Center for the Arts at the Prince Theater 40 Properties
Historical Society of Kent County Maryland 40 Properties
Washington College 40 Properties
Rolphs Wharf Marina 27 Properties

Frequently Asked Questions About Chestertown?

What are the top hotels or resorts in Chestertown?

You have a lot of choices in or near Chestertown. If you need a hotel in the Chestertown area, consider making a reservation for a few nights at one of our suggested properties as these have been known to be the Top Vacation Rentals and Places to Stay in Chestertown:

How many vacation rentals have private pools in Chestertown?

There are 1 accommodation options with private pools in or near Chestertown. Top-rated hotels, resorts, and places to stay that have access to a swimming pool include:

How many hotels, resorts, or rentals are available in Chestertown?

At present, the total number of properties listed by Hotala -- including hotels, resorts, and rentals -- as of 2025 is over 62 in the Chestertown area, and still growing. By combining listings from multiple websites, Hotala provides a huge selection of the best hotels, resorts, and vacation properties in Chestertown.


People Also Ask

There are 5 hotels in Chestertown and 51 rentals

Recently Booked Hotels, Resorts, or Rentals in Chestertown