Chestertown Vacation Rentals

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Dec 26 - Dec 28
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Apr 3 - Apr 5

Our top choices for Chestertown vacation rentals

Property grounds
First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown

Chestertown
9.6 out of 10, Exceptional, (108)
"Amazing and neat and very private "
United States
Alexander M.
$144 nightly
The price is $159
Dec 10 - Dec 11
Total with taxes and fees
First Floor Studio Apartment in Historic Chestertown
Printers
Hudson house

Hudson house

3.5 star property
Canton
$283 nightly
The price is $333
Dec 10 - Dec 11
Total with taxes and fees
Hudson house
Exterior
Upper Chesapeake Bay 5 bedroom, 3 bath, Hot Tub, Waterfront

Upper Chesapeake Bay 5 bedroom, 3 bath, Hot Tub, Waterfront

Perryville
10.0 out of 10, Exceptional, (20)
"Great waterfront home with sunset views! Plenty of space for our group, very clean, and the hot tub was a perfect bonus. Peaceful, relaxing, and just as described. We’d definitely come back!"
United States
Kaylyn G.
Upper Chesapeake Bay 5 bedroom, 3 bath, Hot Tub, Waterfront
Property grounds
Firepit, Beach, Pier and Gorgeous views without leaving your home ! ! !

Firepit, Beach, Pier and Gorgeous views without leaving your home ! ! !

Pasadena
9.4 out of 10, Exceptional, (89)
"This property was a great place for a family to all relax together, play games, and enjoy the water!"
United States
Armando V.
Firepit, Beach, Pier and Gorgeous views without leaving your home ! ! !
Fridge, microwave, oven, stovetop
Spacious historic home downtown Annapolis Main St. Book for Commissioning Week!

Spacious historic home downtown Annapolis Main St. Book for Commissioning Week!

Historic District
9.4 out of 10, Exceptional, (19)
"Great place, excellent location!"
United States
Joseph C.
Spacious historic home downtown Annapolis Main St. Book for Commissioning Week!
6 bedrooms, iron/ironing board, WiFi, bed sheets
Luxury Waterfront Home Built for Entertaining!

Luxury Waterfront Home Built for Entertaining!

Abingdon
8.4 out of 10, Very Good, (6)
"Quite lovely house with a gorgeous view over the water. It is definitely a good spot to stay with a large family or friends for a few days with plenty to do (relaxing on the dock, play games inside, not too far from Baltimore and other nice towns, etc). The host was great and very communicative as well.The only downsides were details around cleanliness and the check-out procedures. The house itself was overall fine, but there dishes left in the dishwasher that we had to put away, the bottom...
United States
Benjamin J.
$786 nightly
The price is $833
Dec 10 - Dec 11
Total with taxes and fees
Luxury Waterfront Home Built for Entertaining!
Fridge, microwave, oven, stovetop
Historic Annapolis~New interior~5+ parking spaces~6BR, 4BA

Historic Annapolis~New interior~5+ parking spaces~6BR, 4BA

Historic District
10.0 out of 10, Exceptional, (33)
"Beautiful home in a great central location for walking to most downtown and USNA destinations. "
United States
Hunter S.
Historic Annapolis~New interior~5+ parking spaces~6BR, 4BA
Property grounds
Charming 2-bedroom house with fitness room and AC in Glen Burnie

Charming 2-bedroom house with fitness room and AC in Glen Burnie

2.0 star property
Glen Burnie
10.0 out of 10, Exceptional, (2)
"The host was very welcoming and very responsive to messages. The space was perfect size for us and very clean!"
United States
Jodi G.
Charming 2-bedroom house with fitness room and AC in Glen Burnie
Marina
Floating 2 bed 2 bath condo stunning views of the bay

Floating 2 bed 2 bath condo stunning views of the bay

2.0 star property
Stevensville
6.4 out of 10, (7)
"Beautiful view! Could hear the tiki bar music from the top. Easy to get to woth lots of things to do nearby. "
United States
Natalia F.
Floating 2 bed 2 bath condo stunning views of the bay
Fridge, microwave, oven, stovetop
Entire House by the Fells Point, JHU.

Entire House by the Fells Point, JHU.

Upper Fells Point
9.4 out of 10, Exceptional, (29)
"Great spot so we could be close to our daughter. Comfortable and well stocked. "
United States
Elizabeth B.
$264 nightly
The price is $305
Jan 1 - Jan 2, 2026
Total with taxes and fees
Entire House by the Fells Point, JHU.
Property grounds
Chesapeake Cottages- 2 Quaint Waterfront Retreats

Chesapeake Cottages- 2 Quaint Waterfront Retreats

Pasadena
9.6 out of 10, Exceptional, (22)
"Excellent Property"
United States
Buu T.
$583 nightly
The price is $665
Dec 10 - Dec 11
Total with taxes and fees
Chesapeake Cottages- 2 Quaint Waterfront Retreats
1 bedroom, iron/ironing board, travel crib, free WiFi
Romantic Hot Tub Getaway, Walking Distance to Fells Point

Romantic Hot Tub Getaway, Walking Distance to Fells Point

Upper Fells Point
10.0 out of 10, Exceptional, (33)
"Awesome place.. take advice on parking when offered "
United States
Steven B.
$169 nightly
The price is $195
Dec 18 - Dec 19
Total with taxes and fees
Romantic Hot Tub Getaway, Walking Distance to Fells Point
Smart TV
The Hideaway Spot- Waterfront w/ Dock on Long Cove

The Hideaway Spot- Waterfront w/ Dock on Long Cove

Glen Burnie
8.6 out of 10, Excellent, (8)
"This place had everything we needed for a great family Christmas. Responsive host. Fun times! "
United States
Tammy A.
$305 nightly
The price is $348
Dec 10 - Dec 11
Total with taxes and fees
The Hideaway Spot- Waterfront w/ Dock on Long Cove
Marina
Cass-N-Reel Luxury Houseboat

Cass-N-Reel Luxury Houseboat

Grasonville
10.0 out of 10, Exceptional, (47)
"Amazing views! Location is great, restaurants at walking distance, great bicicle trail, highly recommended!"
United States
Oliver C.
Cass-N-Reel Luxury Houseboat
Spa
Stunning waterfront villa with indoor pool and kids swing set and play area.

Stunning waterfront villa with indoor pool and kids swing set and play area.

Earleville
9.8 out of 10, Exceptional, (20)
"Had a good time, grandkids never came out of the pool"
United States
Michael D.
Stunning waterfront villa with indoor pool and kids swing set and play area.
Interior
Quiet SPA Loft Studio Apt. Relaxing Getaway with private garage Annapolis

Quiet SPA Loft Studio Apt. Relaxing Getaway with private garage Annapolis

Annapolis
9.4 out of 10, Exceptional, (36)
"Very communicative host and the in apartment sauna and jacuzzi tub really helped us relax. A great stay overall!"
United States
George H.
Quiet SPA Loft Studio Apt. Relaxing Getaway with private garage Annapolis
Fridge, microwave, oven, stovetop
Woodland Retreat on Kent Island: 5 beds, 5 miles from Bay Bridge, on 5 acres.

Woodland Retreat on Kent Island: 5 beds, 5 miles from Bay Bridge, on 5 acres.

Stevensville
10.0 out of 10, Exceptional, (15)
"The property is excellent for entertaining and family gatherings. Everything was clean and tastefully appointed."
United States
Kerrith D.
Woodland Retreat on Kent Island: 5 beds, 5 miles from Bay Bridge, on 5 acres.
Smart TV, books
Large 2 bedroom house with private parking in a nice neighborhood

Large 2 bedroom house with private parking in a nice neighborhood

Arnold
9.4 out of 10, Exceptional, (36)
"This place was perfect place to stay while visiting the area. Everything was clean and the location was great for visiting Annapolis. Will stay again when we are back out this way."
United States
Jim G.
$286 nightly
The price is $325
Dec 10 - Dec 11
Total with taxes and fees
Large 2 bedroom house with private parking in a nice neighborhood
Fridge, microwave, oven, stovetop
family-friendly 2-bedroom home in Baltimore with WiFi, AC, Pool table, Poker

family-friendly 2-bedroom home in Baltimore with WiFi, AC, Pool table, Poker

2.0 star property
Berea
9.6 out of 10, Exceptional, (5)
"Everything was great, easy check in and simple and clean space!!! Amazing thank you"
United States
michael t.
$207 nightly
The price is $239
Dec 19 - Dec 20
Total with taxes and fees
family-friendly 2-bedroom home in Baltimore with WiFi, AC, Pool table, Poker
Fridge, microwave, oven, stovetop
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably

Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably

Cape Saint Claire
10.0 out of 10, Exceptional, (39)
"Fabulous place. We’ll be booking again next year. "
United States
Steve R.
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
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

Hampton Inn Baltimore/Glen Burnie

Hampton Inn Baltimore/Glen Burnie

10/10 Excellent
"Rooms were clean and staff was very friendly "
Shailesh 1-night trip
Posted 22 hours ago
Hampton Inn Baltimore/Glen Burnie

Find out more about Chestertown

Everything you need to know about Chestertown vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Chestertown vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Chestertown vacation 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 low season months. For more hustle and bustle, you may prefer to visit Chestertown in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $159 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Chestertown rentals

At Expedia, we put the best Chestertown vacation 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 vacation.

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.

Explore a world of travel with Expedia

Frequently asked questions

Are there vacation rentals in Chestertown?

Yes, we offer vacation rentals in Chestertown close to Crumpton Auction, or you can go with a more secluded option if you're looking for extra privacy while you relax. 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 vacation home rentals that Chestertown has to offer?

Upper Chesapeake Bay 5 bedroom, 3 bath, Hot Tub, Waterfront: This vacation home rental outside of Chestertown is located on a river and has a patio, a garden, and a barbecue grill to put you at ease in your new surroundings. It has 5 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a selection of games and a hot tub.

How many vacation rentals are there in Chestertown?

Expedia has 23 vacation 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 vacation rentals like in Chestertown?

Vacation rentals are private properties you can stay in for a couple days or more in Chestertown. Vacation rentals feature extras such as WiFi and washers and dryers so you'll feel just like you're at home. If you're concerned about a sanitized environment, vacation rentals can offer a sense of security away from shared hotel elevators and busy reception areas while still allowing you the enjoyment of travel. You'll also have more space in a vacation rental than in a standard hotel, which makes a vacation rental a great choice for a family getaway.