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Hotels in Chestertown

See all 96 Hotels in Chestertown
Holiday Inn Express Hotel & Suites Chestertown

Holiday Inn Express Hotel & Suites Chestertown

150 Scheeler Road, Chestertown
3.0 out of 5.0
4.2 out of 5 (16 reviews)

Situated in Chestertown, this hotel is 0.6 mi (0.9 km) from Washington College and 25.2 mi (40.5 km) from Queenstown Premium Outlets.

$92

$92
Driftwood Inn

Driftwood Inn

609 Washington Avenue, Chestertown
2.0 out of 5.0
1.5 out of 5 (2 reviews)

Situated in Chestertown, this motel is 0.2 mi (0.4 km) from Washington College and 26.7 mi (42.9 km) from Queenstown Premium Outlets.

$57

$57
Great Oak Manor

Great Oak Manor

10568 Cliff Rd, Chestertown
4.0 out of 5.0

Nestled on the beach, this Chestertown bed & breakfast is next to a golf course and 9.1 mi (14.6 km) from Washington College.

$142

$142
Quit Guest Room to Stay With" New Full Bed" & Breakfest for low Price

Quit Guest Room to Stay With" New Full Bed" & Breakfest for low Price

7561 Sunburst Ave, Chestertown

Situated in Chestertown, this vacation home is 2.7 mi (4.4 km) from Washington College and 26 mi (41.9 km) from Queenstown Premium Outlets.

Quality Suites

Quality Suites

160 Scheeler Rd, Chestertown
3.0 out of 5.0
3.9 out of 5 (12 reviews)

Situated in Chestertown, this hotel is 0.8 mi (1.4 km) from Washington College and 25.4 mi (40.9 km) from Queenstown Premium Outlets.

John L Stam House

John L Stam House

114 Washington Ave, Chestertown
3.5 out of 5.0

Situated in Chestertown, this bed & breakfast is 0.5 mi (0.8 km) from Washington College and 24.1 mi (38.7 km) from Queenstown Premium Outlets.

$190

$190
Inn at Mitchell House

Inn at Mitchell House

8796 Maryland Pkwy, Chestertown
3.5 out of 5.0
5.0 out of 5 (1 reviews)

Situated near the beach, this bed & breakfast is 11 mi (17.7 km) from Washington College.

$150

$150
Chester River Waterfront, Magnificent Views, Dock, Beach

Chester River Waterfront, Magnificent Views, Dock, Beach

26761 Mallard Rd, Chestertown

Situated in Chestertown, this vacation home is 2.9 mi (4.7 km) from Washington College and 27.5 mi (44.3 km) from Queenstown Premium Outlets.

Waterfront 3 Br/1 ba Country Cottage w/ Gameroomdeep Water,dock, 2 mi From Town

Waterfront 3 Br/1 ba Country Cottage w/ Gameroomdeep Water,dock, 2 mi From Town

9181 American Legion Rd, Chestertown

Situated in Chestertown, this cottage is 2.3 mi (3.8 km) from Washington College and within 32 mi (52 km) of The Mainstay and Queenstown Premium Outlets. Delaware ...

Best Western Plus Hotel & Conference Center

Best Western Plus Hotel & Conference Center

5625 O'Donnell Street, Baltimore
3.5 out of 5.0
3.6 out of 5 (48 reviews)

The Best Western Plus is located just off highway I-95 and 3.8 miles (6.1 km) from Baltimore's port and Cruise Terminal. Little Italy’s restaurants, cafés, and ...

$85

$85
Map

Recently Booked Hotels in Chestertown

Holiday Inn Express Hotel & Suites Chestertown
3.0 out of 5.0
Last booking: 1 hour ago
Hotels in Chestertown

Looking for a place to stay in Chestertown? Well, Orbitz has 7 hotels, most of which rate highly for Room cleanliness and Location.

No matter what your traveling style, you're likely to find a hotel that suits your needs. And you can always stay in the heart of the action — Chesapeake Bay Environmental Center, Fountain Park, Historical Society of Kent County Maryland, Kenneth M Milton Fine Arts and Wilmer Park are calling your name.


Nightlife in Chestertown

After dinner — or a long afternoon of shopping and sightseeing — head to local watering holes like Blue Bird Tavern and Veterans of Foreign Wars for a drink and a taste of Chestertown's nightlife.


Arts and culture in Chestertown

Put a little culture on your itinerary in Chestertown. The exhibits at Historical Society of Kent County Maryland and Stories-The Chesapeake are good places to soak it in and do some people watching.

You can also learn a thing or two while exploring Chestertown — just dive into the books at Clifton M Miller Library and Chestertown Old Book Co. The knowledge-filled halls and campus of Clifton M Miller Library, Chester River Hospital Center: Zwanger Mark L MD and Washington College Geographic Information Systems (GIS) Program may be worthy of a tour.


What to do in Chestertown

Let some of the best in the movie biz charm you from the silver screens at Chester 5 Theatres. Arena Pmg Consulting features some heart-pumping action and entertainment, whether you're watching an intense game or a favorite musician play live at a concert.

On the opposite end of the spectrum, there's Bay Bridge. Here, you can enjoy a little pampering and serenity while in Chestertown.


Getting to Chestertown

If you're flying in, head for Summit Airport — it's one of Chestertown's main transportation hubs.


Where to shop in Chestertown

Peebles, Kent Plaza Shopping Center and Peebles all make it easy to look your best or pick up gifts while in Chestertown. RadioShack offers up its high-tech gadgets for locals and travelers alike.


Arts and culture in Chestertown

Put a little culture on your itinerary in Chestertown. The exhibits at Historical Society of Kent County Maryland and Stories-The Chesapeake are good places to soak it in and do some people watching.

You can also learn a thing or two while exploring Chestertown — just dive into the books at Clifton M Miller Library and Chestertown Old Book Co. The knowledge-filled halls and campus of Clifton M Miller Library, Chester River Hospital Center: Zwanger Mark L MD and Washington College Geographic Information Systems (GIS) Program may be worthy of a tour.


Getting to Chestertown

If you're flying in, head for Summit Airport — it's one of Chestertown's main transportation hubs.


Nightlife in Chestertown

After dinner — or a long afternoon of shopping and sightseeing — head to local watering holes like Blue Bird Tavern and Veterans of Foreign Wars for a drink and a taste of Chestertown's nightlife.


Outdoor activities in Chestertown

There are ways to kick back in Chestertown beyond its marquee attractions. Horn Point Harbor Marina and Chesapeake Bay Environmental Centerare great places to get some fresh air and spend time outside.


* Prices reflect the lowest "base rate" found over the next 30 days. Rates are subject to change and may not include taxes and fees, hotel service charges, extra person charges, or incidentals, such as room service. All rates are displayed in USD unless otherwise noted. Converted rates are provided for your convenience. They are based on today's exchange rate, but the hotel will charge you in the local currency.