Chestertown Holiday Rentals

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Holiday Rentals in Chestertown

Apartment in Chestertown

9.6 out of 10, Exceptional, (107)
"Amazing and neat and very private "
United States
Alexander M.
The price is AU$246
includes taxes & fees
4 Dec - 5 Dec
First Floor Studio Apartment in Historic Chestertown

Holiday Home in 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

Holiday Home in 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 ! ! !

Houseboat in Stevensville

2.0 star property
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

Holiday Home in 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.
The price is AU$1,286
includes taxes & fees
3 Dec - 4 Dec
Luxury Waterfront Home Built for Entertaining!

Holiday Home in Historic District

10.0 out of 10, Exceptional, (33)
"Our stay was AMAZING! Perfect location, plenty of space! Will definitely book again when we have a larger group like we did for PPW! "
United States
Charolene P.
Historic Annapolis~New interior~5+ parking spaces~6BR, 4BA

Residence in Canton

3.5 star property
The price is AU$507
includes taxes & fees
2 Jan - 3 Jan 2026
Hudson house

Holiday Home in 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.
The price is AU$490
includes taxes & fees
1 Jan - 2 Jan 2026
Entire House by the Fells Point, JHU.

Holiday Home in 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.

Cottage in Rosedale

3.0 star property
10.0 out of 10, Exceptional, (1)
The price is AU$760
includes taxes & fees
8 Dec - 9 Dec
5 Mi to Downtown Baltimore: Quiet Home w/ Porch

Houseboat in 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

Cottage in Pasadena

9.6 out of 10, Exceptional, (22)
"Excellent Property"
United States
Buu T.
The price is AU$1,026
includes taxes & fees
4 Dec - 5 Dec
Chesapeake Cottages- 2 Quaint Waterfront Retreats

Houseboat in Baltimore

10.0 out of 10, Exceptional, (11)
"Everything was wonderful - the boat was just as described, even wit a few extra touches that meant a lot - snacks, water bottles, shampoo/conditioner, plenty of hangers, and the SUPER clean, just to name a few! We would love to stay again! Thank you so much!"
United States
Maggie P.
The price is AU$825
includes taxes & fees
8 Dec - 9 Dec
Luxe Houseboat with Epic 360 Views of Baltimore Harbor

Holiday Home in Upper Fells Point

10.0 out of 10, Exceptional, (33)
"Awesome place.. take advice on parking when offered "
United States
Steven B.
The price is AU$282
includes taxes & fees
8 Dec - 9 Dec
Romantic Hot Tub Getaway, Walking Distance to Fells Point

Holiday Home in Glen Burnie

9.8 out of 10, Exceptional, (21)
"Quiet area house was clean close to everything we needed"
United States
Kimberly S.
The price is AU$739
includes taxes & fees
3 Dec - 4 Dec
Cozy Private Family Palace near BWI, Pet-Friendly

Apartment in 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

Holiday Home in Glen Burnie

2.0 star property
10.0 out of 10, Exceptional, (1)
"Everything was clean and comfortable, and the slight door code issue at check in was quickly resolved."
United States
Quinn S.
Charming 2-bedroom house with fitness room and AC in Glen Burnie

Holiday Home in Glen Burnie

8.0 out of 10, Very good, (2)
"No problems close to everything, only gripe was it being a basement and little feet upstairs tend to be a bit lohd. However, just the bathroom alone made this property worth another stay"
United States
James D.
The price is AU$194
includes taxes & fees
3 Dec - 4 Dec
Cozy Private Suite Gated Entry, Driveway Parking & Quiet Stay

Holiday Home in Historic District

9.4 out of 10, Exceptional, (19)
"Great place, excellent location!"
United States
Joseph C.
The price is AU$1,831
includes taxes & fees
8 Dec - 9 Dec
Spacious historic home downtown Annapolis Main St. Book for Commissioning Week!

Holiday Home in Perryville

9.8 out of 10, Exceptional, (146)
"Beautiful home right on the North East River. Comfortable and peaceful. We would definitely stay here again."
United States
Cara R.
The price is AU$916
includes taxes & fees
10 Dec - 11 Dec
5-bedroom vacation home 5 minutes from historic Charlestown
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$194 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 Crumpton Auction, 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?

Upper Chesapeake Bay 5 bedroom, 3 bath, Hot Tub, Waterfront: This holiday home rental outside of Chestertown is located on a river, and has a patio, a garden and a BBQ 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 that you can cook with friends or family. You can relax into your holiday with a selection of games and 1 hot tub.

How many holiday rentals are there in Chestertown?

Expedia has 23 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.