Chestertown Vacations

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Find the Best Chestertown Vacation Packages

Chestertown Hotel Deals

Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown

2.5 out of 5
150 Scheeler Road Chestertown MD
Fully refundable
The price is AEDĀ 408 per night from Aug 16 to Aug 17
AEDĀ 408
AEDĀ 453 total
16 Aug - 17 Aug
includes taxes & fees
8.6/10 Excellent! (935 reviews)
"We stayed there two nights for my daughterā€™s tournament. The room is clean and quiet, the breakfast is good. Highly recommended!"

Reviewed on 16 July 2026

Comfort Inn & Suites Chestertown
The Lodge at Great Oak Landing

The Lodge at Great Oak Landing

3 out of 5
22170 Great Oak Landing Rd Chestertown MD
Fully refundable
The price is AEDĀ 486 per night from Jul 20 to Jul 21
AEDĀ 486
AEDĀ 556 total
20 Jul - 21 Jul
includes taxes & fees
The Lodge at Great Oak Landing
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 AEDĀ 248 per night from Jul 26 to Jul 27
AEDĀ 248
AEDĀ 275 total
26 Jul - 27 Jul
includes taxes & fees
7.2/10 Good! (462 reviews)
"Big room,very comfortable bed,direct tvā€¦.pool was out of order,apparently has been for quite a whileā€¦..enjoyed our stayšŸ˜€"

Reviewed on 11 July 2026

Red Roof Inn & Suites Chestertown
See all 1,086 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.

Stay near popular Chestertown attractions

Washington College

8.6/10 (87 reviews)
Founded in 1782, Washington College is the first college chartered in the sovereign United States. Explore its picturesque campus with historic architecture and Chester River waterfront views.
See properties

Frequently asked questions

How much does a Chestertown vacation package cost?
Offering excellent value package deals on Expedia, you'll be surprised at how little a vacation to Chestertown costs! Expedia's packages mean less travel planning for you and greater savings.
What are the cheapest months to go to Chestertown?
If you're hoping to snag a cheap Chestertown vacation package, consider traveling in December, January and February. You'll typically find lower rates on hotels and flights during these quieter months ā€” ideal for a budget-friendly getaway.
How to find the best Chestertown package deals?
Begin your search for a Chestertown package deal by entering your travel dates and destination under our "Packages" tab. Then select some filters, like "Popular locations" and "Property type," to fine-tune the results to your exact style. You can also sort by "Package discount" and browse offers that come with huge savings. If you don't find the ideal Chestertown package deal straight away, simply change your dates and search again. Bear in mind that deals are only available for a limited time, so book early and get your Chestertown getaway off to a flying start.
Is it cheaper to book a Chestertown vacation as a package?
An Expedia vacation package could land you significant savings when compared to arranging stays and flights separately. Better still, you can tailor your Chestertown escape to fit your exact style. Choose your preferred flight time, select the hotel type and add a car rental. Browse our great deals to see how much you can save.
When to book a vacation package to Chestertown?
Land amazing discounts by reserving your flights in advance with Expedia. If spontaneity is more your thing, take advantage of our last-minute deals for an impromptu Chestertown getaway.
How to plan a trip to Chestertown?

  1. Choose when to go: Check your calendar and get your bags packed. Your preferred time of year and the activities on offer will also help you decide when to vacation in Chestertown.
  2. Calculate your budget: Ensure you have enough money to cover everything from food and transportation to experiences and flights. Your accommodations will probably be the largest expense during your trip to Chestertown.
  3. Set the duration of your trip: Start by compiling a list of the activities and sights you want to get to in Chestertown. Then, estimate how long you'll need at each, as well as any travel time.
  4. Bundle your airfare and accommodations: After you've settled on your trip dates and duration, book the perfect Chestertown vacation package for you.