Chestertown Holidays from £1,544

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Your Chestertown Holiday

There's no better way to embark on an adventure than with one of our holiday packages to Chestertown. The colonial history and cultural experiences are just two of the countless reasons to spend some time in this captivating city. Fill your free time with visits to Washington College, Rolphs Wharf Marina and Garfield Centre for the Arts at the Prince Theatre, some of the things you simply have to see during a trip to Chestertown. A couple of quick clicks is all it takes to put together a tailor-made Chestertown holiday on Expedia.

Top Chestertown Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.
Gold Leaf Hotel of Dewey - Rehoboth Beach

Gold Leaf Hotel of Dewey - Rehoboth Beach

2.5 out of 5
Price was £1,833, price is now £1,544 per person
£1,544
per person
12 Aug - 19 Aug
found 10 hours ago
Return flight included
London (LHR) to Salisbury (SBY)
8.8/10 Excellent! (1,000 reviews)
Stay here frequently. Great location, friendly staff.

Reviewed on 30 Jun 2026

Fenwick Shores, Tapestry Collection by Hilton

Fenwick Shores, Tapestry Collection by Hilton

3.5 out of 5
Price was £2,959, price is now £2,218 per person
£2,218
per person
12 Aug - 19 Aug
found 10 hours ago
Return flight included
London (LHR) to Salisbury (SBY)
9.4/10 Exceptional! (779 reviews)
This hotel was beyond my expectations, the King room had a beautiful balcony, which you could see some of the beach from, the bed and pillows were great! I loved that it actually had a refrigerator and dishwasher in it and microwave and Keurig. As well as a sectional sofa which had a pull out bed, the bathroom was spacious and beautiful! Family friendly. Was pleasantly surprised with all of the details and the staff. We were only there for 1 night - quick trip but definitely will return.

Reviewed on 30 Jun 2026

Hotel Bethany Beach

Hotel Bethany Beach

2.5 out of 5
Price was £2,129, price is now £1,892 per person
£1,892
per person
12 Aug - 19 Aug
found 10 hours ago
Return flight included
London (LHR) to Salisbury (SBY)
9.2/10 Wonderful! (1,458 reviews)
We had a very nice stay at the hotel. The proximity to the beach was excellent and the complimentary 2 beach chairs and 1 umbrella voucher was fantastic! The rooms were clean and good for what we were paying for and expecting. My only issue with the hotel is this…this is a pet friendly hotel (and we knew this), but I contacted the hotel twice to ask if there were certain floors or rooms where pets couldn’t be. I did this due to my wife’s allergies to cats/dogs. We were told pets are only allowed on the pet friendly floor which is #2. Floors 1,3,4 are not pet friendly. Great! We were on floor 4 and on Monday and Tuesday we could hear a dog barking on our floor. I asked my wife if she could tell if an animal was in our room before but she said she felt fine so I would assume no. I have messages from the hotel to me stating that the 2nd floor is the only pet friendly floor. I only write this for others to be aware that I’m not sure how well this protocol is followed or maybe this was an isolated instance. Maybe someone brought a dog up with them to a friends room? I don’t know, BUT I would just be aware. We didn’t press the issue because my wife felt fine so that’s all that mattered but if someone has a severe allergy just be cautious. Otherwise everything from staff to the amenities were great!

Reviewed on 1 Jul 2026

The Bay Resort

The Bay Resort

3 out of 5
Price was £1,846, price is now £1,660 per person
£1,660
per person
12 Aug - 19 Aug
found 10 hours ago
Return flight included
London (LHR) to Salisbury (SBY)
8.6/10 Excellent! (991 reviews)
Dewey Beach is definitely a party town. Lots of people wandering around and lots of noise well into the night. There was an additional charge for parking.

Reviewed on 29 Jun 2026

Atlantic Oceanside Dewey

Atlantic Oceanside Dewey

2.5 out of 5
Price was £1,728, price is now £1,567 per person
£1,567
per person
12 Aug - 19 Aug
found 10 hours ago
Return flight included
London (LHR) to Salisbury (SBY)
8.2/10 Very good! (1,013 reviews)
It is an older re-painted property. Quite modest but it gets the job done. We had one window that looked out to the parking lot. If u want a place to just go to sleep, with no frills except a small pool, this is it. Its clean and very basic and no reminder that you are by the ocean.

Reviewed on 1 Jul 2026

Chestertown Essential Information

Language
English
Currency
U.S dollars
Population
5,100
Max Temp Winter
7ºC
Max Temp Summer
27ºC
Top Sights
Historical Society of Kent County Maryland, Garfield Centre for the Arts at the Prince Theatre and Crow Farm and Vineyard

Top hotels in Chestertown

Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown

2.5 out of 5
150 Scheeler Road Chestertown MD
Fully refundable
The price is £90 per night from 28 Jul to 29 Jul
£90
28 Jul - 29 Jul
includes taxes & fees
8.6/10 Excellent! (929 reviews)
"Problems with checking in and washing machine not working. Staff didn’t care."

Reviewed on 29 Jun 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 £114 per night from 16 Jul to 17 Jul
£114
16 Jul - 17 Jul
includes taxes & fees
7.8/10 Good! (89 reviews)
"Is a beautiful and quiet place to relax"

Reviewed on 29 Jun 2026

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 £60 per night from 20 Jul to 21 Jul
£60
20 Jul - 21 Jul
includes taxes & fees
7.2/10 Good! (458 reviews)
"The property is a little older and could benefit from a good deep cleaning of carpets and upholstery, but the bed and bathroom were clean and the staff were great. Considering the price of other accomodations in the area it's an excellent value for the money if you're just looking for a clean place ..."

Reviewed on 22 Jun 2026

Red Roof Inn & Suites Chestertown
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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.
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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 travel package cost?
From as low as £1,544. Yes, you read that right. Our Chestertown travel packages are the quickest way to make your dollars go much further. Bundle your hotels, flights and rental car and get out and explore this fabulous destination.
If I'm not able to travel, can I cancel my Chestertown travel package?
You sure can, and we're here to help. You may be able to cancel or change your Chestertown travel package for free if you booked in the last 24 hours. However, you may be charged a fee by your airline, hotel or car rental company if your booking is older than that. If your circumstances unexpectedly change, take a look at our Customer Service Portal for more information.
How do I get a cheap travel package to Chestertown?
Simply by bundling. Flights, rental cars and hotels — combine whatever you need into a Chestertown travel package to save a pile of cash. Score even more deals when you add extras such as day tours to your booking. But that's not the only impressive part. You have the flexibility to customize your holiday your way. We offer over 550 partner airlines and 1,000,000 hotels throughout the world, so that everyone has an opportunity to travel and fulfil those holiday fantasies.
Does Expedia offer Book Now, Pay Later Chestertown holidays?
We do. Expedia has partnered with online lender Klarna to help you conveniently pay for your trip in instalments. Simply pick the payment plan that works for you during the checkout process and take away the stress of budgeting for your next trip. Remember to bundle your flights, car hire and hotel with Expedia to get the biggest bang for your holiday buck. Browse our flexible payment options below:

  • Pay monthly holidays: Klarna offers easy monthly payment plans that suit all budgets, so you can have that well-deserved holiday sooner.
  • Pay in instalments holidays: With this Book Now, Pay Later option, Klarna allows you to pay off your trip across multiple transactions.
  • Low deposit holidays: If paying a small percentage of your trip (rather than all of it upfront) makes it easier to hit that "book now" button, choose a low deposit holiday payment plan from Klarna.

Where should I stay in Chestertown?
With loads to explore in Chestertown, it's a good idea to lock in a hotel near its attractions. Washington College, Historical Society of Kent County Maryland and Rolphs Wharf Marina are some good ones to add to your to-do list.
What are the top hotels in Chestertown?
If it's your first time in Chestertown, lock in a room at Comfort Inn & Suites Chestertown or Red Roof Inn & Suites Chestertown. Both hotels offer comfortable beds and are popular options with many travellers.
How far in advance should I book my Chestertown holiday?
Reserving your seat early with Expedia means one less thing to have to worry about. Most air carriers advertise tickets up to 12 months prior to departure dates. This is usually the cheapest time to book. If circumstances have left you booking late, last-minute deals to Chestertown are still known to appear just a few weeks before departure.
What does an Expedia Chestertown travel package include?
Select from any combination of rental cars, flights and hotels. Once you've made your booking, you can add the fun stuff like experiences and tours. Want to pick your airfare class? That's also easy to do. The choice is all yours when it comes to crafting your perfect Chestertown escape.
What should I know before booking a Chestertown travel package?
You'll pick up amazing savings when you combine your hotels, flights and rental cars into a travel package. Not just that, booking everything in one place simply makes planning easier. So why waste your time or money? Whether you're putting together a luxury romantic escape or a low-cost family break, have a look at our travel packages today.
Can I choose my airline with a Chestertown Expedia travel package?
Expedia has access to more than 550 partner airlines globally, so you sure can! Just select the airline you want and put together your ideal Chestertown getaway.

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.