Chestertown Holiday Rentals

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Our top choices for Chestertown holiday rentals

9.6 out of 10, Exceptional, (108 reviews)
"Everything was clean and neat and welcoming "
United States
Iriana J.
The price is AU$226
includes taxes & fees
5 Mar - 6 Mar
First Floor Studio Apartment in Historic Chestertown
9.6 out of 10, Exceptional, (12 reviews)
"Had a short getaway for a couple this location was perfect for our visit to Chestertown and the local establishments in Grasonville. Will definitely book this again. "
United States
Joe C.
The price is AU$581
includes taxes & fees
5 Mar - 6 Mar
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
9.0 out of 10, Wonderful, (13 reviews)
"Great experience"
United States
David P.
The price is AU$483
includes taxes & fees
2 Apr - 3 Apr
18th Cent. Charm in Historic Downtown Annapolis
9.8 out of 10, Exceptional, (43 reviews)
"We had a great stay! The property has everything we needed and host was easy to communicate with "
United States
Stephanie S.
The price is AU$385
includes taxes & fees
16 Mar - 17 Mar
Relax on Kent Island in a 4 Bedroom Home w/Waterview!
10.0 out of 10, Exceptional, (5 reviews)
"Perfect location. Very clean. Had everything we needed and front porch swing was a nice bonus. Would stay here every visit! "
United States
Tracie B.
The price is AU$993
includes taxes & fees
5 Mar - 6 Mar
Historic Row Home | Hot Tub - 1 Block from Gate 1!
9.6 out of 10, Exceptional, (34 reviews)
"Great stay, would do it again."
United States
Brandon D.
The price is AU$391
includes taxes & fees
17 Mar - 18 Mar
Charming Coastal/Country Home w/3 Acres & Sauna!
9.6 out of 10, Exceptional, (94 reviews)
"Lenny & his housekeeper Elviea were exceptionally helpful, funny and a delight to be with! I spent two weeks here & it was the best place I've ever stayed compared to my stays in Korea, Ireland & several other US cities. Highly recommend!"
United States
Edward J.
The price is AU$304
includes taxes & fees
8 Mar - 9 Mar
Hidden Fells Point Gem / Private Courtyard Patio
10.0 out of 10, Exceptional, (25 reviews)
"The apartment, including kitchen and bathroom, was very clean. Plenty of linens available for use. Perfect spot for fishing off of their dock. Very pleased with our reservation. "
United States
Debbie S.
The price is AU$441
includes taxes & fees
5 Mar - 6 Mar
Waterfront Retreat with Private Dock and Beach
9.8 out of 10, Exceptional, (148 reviews)
"Magical and made tons of family wedding memories. What a perfect house on the river!! We will be booking again"
United States
Mary D.
The price is AU$741
includes taxes & fees
5 Mar - 6 Mar
5-bedroom vacation home 5 minutes from historic Charlestown
8.0 out of 10, Very good, (12 reviews)
"Pleasant stay"
United States
Yommali G.
The price is AU$133
includes taxes & fees
15 Mar - 16 Mar
Charming 2-bedroom house in Aberdeen with WiFi and AC
9.2 out of 10, Wonderful, (9 reviews)
"The house is a beautiful place to stay. The location was ideal for going to attractions and stores. "
United States
Laurie S.
The price is AU$489
includes taxes & fees
5 Mar - 6 Mar
Amazing Modern house with a full kitchen and parking
9.6 out of 10, Exceptional, (20 reviews)
"So pleased with all aspects of my stay. Clean, Comfortable, Quiet, Amenities all beyond expectation."
United States
Cynthia C.
The price is AU$179
includes taxes & fees
24 Mar - 25 Mar
Guest Suite for up to 2 in a Victorian on the Chester River
9.4 out of 10, Exceptional, (36 reviews)
"Super clean place, great communication from the host, and home is exactly as described and shown in pictures. "
United States
Traci L.
The price is AU$445
includes taxes & fees
5 Mar - 6 Mar
Large 2 bedroom house with private parking in a nice neighborhood
10.0 out of 10, Exceptional, (5 reviews)
"It is a warm and welcoming little home away from home. We will be back!"
United States
Brittany C.
The price is AU$271
includes taxes & fees
6 Mar - 7 Mar
Cozy 2-bedroom apartment with WiFi, AC in charming Havre de Grace
The price is AU$594
includes taxes & fees
9 Mar - 10 Mar
FLOHOM 14 Luxury Houseboat with Chesapeake Bay Panoramic Views

Holiday Home in Historic District

Cozy 2br home w/ parking in downtown Annapolis
10.0 out of 10, Exceptional, (75 reviews)
"Welcoming host, great location and easy parking "
United States
Chris B.
The price is AU$450
includes taxes & fees
24 Mar - 25 Mar
Cozy 2br home w/ parking in downtown Annapolis
10.0 out of 10, Exceptional, (3 reviews)
"House kept very clean and neighborhood was really quiet at night! Will be staying again."
United States
Pai’Syn
The price is AU$376
includes taxes & fees
10 Mar - 11 Mar
Boho Oasis 2 Bed 1 Bath home in Baltimore City!
10.0 out of 10, Exceptional, (12 reviews)
"Very clean first off I would’ve ate off the floor. Honestly these people have to love what they do to deliver such a 5 star experience "
United States
Anonymous traveller
The price is AU$797
includes taxes & fees
9 Mar - 10 Mar
Luxe Houseboat with Epic 360 Views of Baltimore Harbor
10.0 out of 10, Exceptional, (23 reviews)
"We enjoyed this property so much that we stayed here again just 4 months later."
United States
Kim C.
The price is AU$536
includes taxes & fees
5 Mar - 6 Mar
Glen Burnie Escape - Pet friendly with easy access to multiple attractions.
10.0 out of 10, Exceptional, (18 reviews)
"Close to Main Street. Very nice and spacious accommodations."
United States
Michael D.
The price is AU$413
includes taxes & fees
8 Mar - 9 Mar
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
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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Top Chestertown Hotel Reviews

Find out more about Chestertown

Everything you need to know about Chestertown holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Chestertown holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Chestertown holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Chestertown holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Chestertown. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Chestertown holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Chestertown holiday rentals we have selected for you start as low as AU$376 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Chestertown rentals

At Expedia, we put the best Chestertown holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Chestertown rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Chestertown holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Chestertown. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Are there holiday rentals in Chestertown?

Yes, there are holiday rentals in Chestertown close to Garfield Center for the Arts at the Prince Theater, or you can select a more secluded option if you're looking for a relaxing stay. Chestertown is known for its sporting events and university setting. Make sure you have time to check out the festivals and art during your trip.

What are some of the best holiday rentals that Chestertown has to offer?

Beautiful, Open floor plan, amazing sunset views,Waterside Pool, Pier, 6+ac: This holiday home rental outside of Chestertown is located on the waterfront, and has an outdoor pool, a fireplace and a BBQ to put you at ease in your new surroundings. It has 6 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a balcony, a garden and a selection of games so that you can immerse yourself in your holiday.

How many holiday rentals are there in Chestertown?

Expedia has 24 holiday rentals for your stay in Chestertown.

What can I see and do in Chestertown?

Enjoy the outdoors at Northern Chesapeake Bay and Chesapeake Bay, or simply take in cultural attractions like Historical Society of Kent County Maryland and Garfield Center for the Arts at the Prince Theater. Chestertown Historic District and Rolphs Wharf Marina are other places to visit while you're in town.

What are holiday rentals like in Chestertown?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Chestertown. Holiday rentals offer extras like laundry facilities and kitchens to help you enjoy your stay. If you're concerned about cleanliness, holiday rentals can offer a sense of security away from shared hotel lifts and busy concierge desks while still allowing you to travel. You'll also have more space in a holiday rental than in a standard hotel, which makes a holiday rental a great option for a small group gathering.