Chestertown Trips (flight + hotel)

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Top hotels in Chestertown

Comfort Inn & Suites Chestertown
Comfort Inn & Suites Chestertown
2.5 out of 5
150 Scheeler Road, Chestertown, MD
Fully refundableReserve now, pay when you stay
The price is P6,219 per night from 3 Dec to 4 Dec
P6,219
P6,904 total
includes taxes & fees
Dec 3 - Dec 4
8.4/10 Very Good! (721 reviews)
"The staff was very nice with one exception-the night attendant-he was nice just not helpful…."

Reviewed on Oct 14, 2024

Comfort Inn & Suites Chestertown
Red Roof Inn & Suites Chestertown
Red Roof Inn & Suites Chestertown
2 out of 5
160 Scheeler Rd, Chestertown, MD
Fully refundableReserve now, pay when you stay
The price is P4,626 per night from 3 Dec to 4 Dec
P4,626
P5,135 total
includes taxes & fees
Dec 3 - Dec 4
7.2/10 Good! (313 reviews)
"A little rough around the edges in some ways, but the rooms were large, quiet, and clean."

Reviewed on Oct 21, 2024

Red Roof Inn & Suites Chestertown
La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh
La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh
2.5 out of 5
4 Philadelphia Ct, Rosedale, MD
Fully refundableReserve now, pay when you stay
The price is P4,021 per night from 24 Nov to 25 Nov
P4,021
P4,645 total
includes taxes & fees
Nov 24 - Nov 25
7/10 Good! (1,011 reviews)
"Nice, clean room. But 1st room given to us is not ready yet/ dirty. Waited to get another room."

Reviewed on Oct 31, 2024

La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh
See all 1,014 properties in Chestertown
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.

Frequently asked questions

How much does a Chestertown vacation package cost?
The most affordable Chestertown package is , so your dream getaway can become a reality — without it costing a fortune. Combine flights, hotels, car rentals and more to tailor a package suited to your travel style.
How do I get a cheap travel package to Chestertown?
Browse and lock in everything all in one place with our Chestertown vacation packages. You’ll find deals on hotels, flights, tours and more that’ll keep your wallet happy and your adventurous spirit busy. And, with more than 550 air carriers and 1,000,000 hotels across the globe to select from, you’ll have endless opportunities to mix and match your own way.
Where should I stay in Chestertown?
Stay close to the action. Many people book hotels within easy reach of popular sights, such as Washington College, Rolphs Wharf Marina and River Arts Chestertown.
What are the top hotels in Chestertown?
If it’s your first time staying in Chestertown, reserve a room at Circa 1900 Home In The Heart Of Historic Downtown Chestertown or Historic Downtown Chestertown Home. #1 Location. Both have good amenities and are favorites among many savvy travelers.
How far in advance should I book my Chestertown vacation?
To score cheap prices, book ASAP. Airlines usually start selling tickets, along with some of the lowest fares, up to a year prior to departure. Hotels, experiences and car rental should also be booked well in advance to avoid disappointment. If you’ve decided on a last-minute getaway in Chestertown, there are always lots of great bargains to be had on Expedia. Book your escape today!
What does an Expedia Chestertown travel package include?
Much of that depends on you. You can select from a range of Chestertown bundles, such as a flight, hotel and rental car. You can also book a flight and a hotel, or a rental car with a flight. Once you’ve made your booking, you can add the fun stuff like tours and activities. Whatever your perfect Chestertown vacation looks like, you’ll save!
What should I know before booking a Chestertown travel package?
When you book your hotels, flights and car rentals together, you’ll score great discounts. Whether you’re organizing a rural escape in a cottage or want to stay in a convenient hotel in the city, Expedia can help make it happen.
Can I choose my airline with a Chestertown Expedia vacation package?
Definitely. Expedia has over 550 partner airlines to choose from all over the world. With all that choice at your fingertips, finding the right carrier to get you to Chestertown will be easy.
If I'm not able to travel, can I cancel my Chestertown vacation package?
Don’t worry if you’re rethinking your Chestertown vacation package — it’s possible to change or amend your booking. And if you’ve booked it within the last 24 hours, you may be able to do it at no cost. However, bookings made more than 24 hours ago may incur fees from your hotel, airline or car rental company. We understand life can sometimes throw a spanner in the works, so head to our Customer Service Portal if that occurs. When you’re ready to make changes, we’ll be here to help.

Popular places to visit

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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
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Wilmer Park

Explore the great outdoors at Wilmer Park, a lovely green space in Chestertown. Amble around this family-friendly area's riverfront or experience its festivals.

Wilmer Park
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Crumpton Auction

Take the family on an outing to Crumpton Auction during your trip to Chestertown. Take in the festivals while you're in the area.

Crumpton Auction
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.