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Top Chestertown hotels deals

Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown

2 out of 5
160 Scheeler Rd, Chestertown, MD
Free cancellation
Reserve now, pay when you stay
The price is CA $89 per night
CA $89
CA $98 total
includes taxes & fees
30 Mar - 31 Mar
Stay at this hotel in Chestertown. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff in our reviews. Popular attractions Rolling Road Park and Historical Society of Kent County Maryland are located nearby.
Pet-friendly
Parking included
Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown

2.5 out of 5
150 Scheeler Road, Chestertown, MD
Free cancellation
Reserve now, pay when you stay
The price is CA $149 per night
CA $149
CA $165 total
includes taxes & fees
20 Apr - 21 Apr
Book a stay at this business-friendly hotel in Chestertown. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Rolling Road Park and Historical Society of Kent County Maryland are located nearby.
Breakfast included
Pet-friendly
Historic Inns of Annapolis

Historic Inns of Annapolis

3.5 out of 5
58 State Circle, Annapolis, MD
Free cancellation
Reserve now, pay when you stay
The price is CA $172 per night
CA $172
CA $244 total
includes taxes & fees
31 Mar - 1 Apr
Book a stay at this historic hotel in Annapolis. Enjoy free WiFi, room service, and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions The Colonial Players and 97, 99 and 101 East Street are located nearby.
Pet-friendly
Free WiFi
Sagamore Pendry Baltimore

Sagamore Pendry Baltimore

5 out of 5
1715 Thames St., Baltimore, MD
Free cancellation
Reserve now, pay when you stay
The price is CA $464 per night
CA $464
CA $604 total
includes taxes & fees
13 Apr - 14 Apr
Stay at this 5-star luxury hotel in Baltimore. Enjoy free WiFi, an outdoor pool, and 2 bars/lounges. Our guests praise the helpful staff in our reviews. Popular attractions Baltimore Inner Harbor Marina and National Aquarium in Baltimore are located nearby.
Pool
Spa
Quality Inn & Suites Bel Air I-95 Exit 77A

Quality Inn & Suites Bel Air I-95 Exit 77A

2.5 out of 5
2112a Emmorton Park Road, Edgewood, MD
Free cancellation
Reserve now, pay when you stay
The price is CA $79 per night
CA $79
CA $89 total
includes taxes & fees
7 Apr - 8 Apr
Book a stay at this business-friendly hotel in Edgewood. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions CopperPlex and Cedar Lane Regional Park are located nearby.
Breakfast included
Parking included
Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina

3 out of 5
3028 KENT NARROW WAY S, Grasonville, MD
Free cancellation
Reserve now, pay when you stay
The price is CA $187 per night
CA $187
CA $208 total
includes taxes & fees
9 Apr - 10 Apr
Stay at this 3-star business-friendly hotel in Grasonville. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Chesapeake Bay Environmental Center and Paul Reed Smith Guitars are located nearby.
Pool
Pet-friendly
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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.

Popular places to visit

Washington College

Take a campus tour or just explore the area of Washington College, during your travels in Chestertown. Amble around this family-friendly area's riverfront or experience its festivals.

Washington College

Rolphs Wharf Marina

Explore the waterfront in Chestertown with a trip to Rolphs Wharf Marina. Take in the festivals in this family-friendly area.

Rolphs Wharf Marina

River Arts Chestertown

Explore the campus of River Arts Chestertown, during your travels in Chestertown. Take in the festivals in this family-friendly area.

River Arts Chestertown

Chestertown Vacations

You don't need to know everything about the place to have an awesome time in Chestertown, but you will need to know a few basic things before you set off.

To help get you oriented, Chestertown sits 30 miles (48 kilometers) east of the well-known city of Baltimore.

This is an area of Eastern Shore that around 5,000 people call home.

Places to visit in Chestertown

Abandon your history books! Let the past jump off the page at Historical Society of Kent County Maryland. Seeking some more options? Great theater can challenge our expectations and asks us to aspire to bigger and better things. Catch a play at Garfield Center for the Arts at the Prince Theater and open your mind to some new ideas. And there's more. You don't need to be a prodigy to admire the vast halls and intriguing past of Washington College.

Where do you fly into for Chestertown?

Slip on your headphones and watch one of the latest in-flight movies. Before long, you'll hit the tarmac at Baltimore Washington International Thurgood Marshall Airport (BWI). It's approximately 30 miles (48 kilometers) to the west from the middle of Chestertown.

Frequently asked questions

How much are vacation packages to Chestertown?
Your vacation fantasies can come to life in Chestertown for as little as . Our packages include flights and hotels, so you’ll find booking is a cinch. The only thing you’ll have to worry about is having a good time.
How long should my Chestertown vacation be?
Around 2 nights is the average amount of time travelers spend in Chestertown. But the ideal trip length comes down to how many magical memories you want to make. Why not allow a few extra days and explore some of the lesser-known spots?
Where can I get the best vacation package deals for Chestertown?
For the perfect Chestertown package deal, head straight to Travelocity. Choose from 400 partner airlines and 665,000 properties across the globe to create your ideal trip — it couldn’t be easier than that.
Why should I purchase my Chestertown vacation bundle with Travelocity?
The three S’s — savings, support and a stress-free booking — are just the beginning. Enjoy a fulfilling travel experience knowing you can rely on round-the-clock support. With the Travelocity Price Match Guarantee, you know you’ll always get the best deal available.
Can I save on my Chestertown car rental if I bundle it with hotels and flights?
You certainly can — bundle your car, flight and hotel into a Chestertown vacation package and you’ll save a ton. With so much to see and do in the Chestertown area, that rental car will more than come in handy. Once you’ve buckled up, put the stereo on and make tracks to White House, a renowned attraction around 90 kilometersfrom Chestertown.
What is the best time of year to go to Chestertown?
You’ll pick up the cheapest hotel prices in and pay more in . You can expect it to be quieter in , while there’ll be more fellow visitors to meet during . It comes down to what prices you’re willing to pay, the climate and how you deal with crowds.
Which airport is best for Chestertown?
One of the most convenient options is Washington, DC (DCA-Ronald Reagan Washington National), which is located 90 kilometerssouthwest of the hustle and bustle of downtown Chestertown. You can also jet into Baltimore, MD (BWI-Baltimore Washington Intl. Thurgood Marshall), 50 kilometersaway from central Chestertown).
What is there to do in Chestertown?
Washington College is one of the memorable sights that make Chestertown a popular place to visit. But give yourself enough time to roam its lesser-known attractions too. This is sometimes where the best memories are created.
Where should I stay when visiting Chestertown?
Many visitors stay at the Holiday Inn Express Hotel & Suites Chestertown. It’s an excellent base for your Chestertown getaway.
Can I go on vacation to Chestertown at this time?
Don’t plan your trip to Chestertown without up-to-date facts about travel restrictions and quarantine policies. Travelocity’s Covid-19 Travel Advisor will fill you in. It has all the information you need to make your getaway as relaxed as possible.

Photos of local treasures

Browse Chestertown vacation photos for more inspiration

Photo by Assya A
Photo by Assya A
Photo by Patricia Knorr
Photo by Patricia Knorr
Photo by Patricia Knorr
Photo by Patricia Knorr