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Chestertown Vacation Rentals

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Vacation Rentals in Chestertown

350 Acre Waterfront Farm; High Speed Internet, Pool, Pickleball & Private Dock
Pool | Outdoor pool
350 Acre Waterfront Farm; High Speed Internet, Pool, Pickleball & Private Dock
10.0 out of 10, Exceptional, 52 reviews
"My family of 4 stayed here. So many things to do outside-truly a good time. So many games and accessories to have an easy good time. Would definitely stay at this place again."
350 Acre Waterfront Farm; High Speed Internet, Pool, Pickleball & Private Dock
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
Fridge, microwave, oven, stovetop
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
10.0 out of 10, Exceptional, 4 reviews
"Wonderful place to stay and Erin was great. Asked about a Grill on the property and the next day we had a grill. The young adults loved the pool and water activities while the older adults enjoyed sitting on the docks watching the sunrise with a cuppa coffee. Would highly recommend this property."
The price is ￥98,898
￥226,025 total
includes taxes & fees
Jun 5 - Jun 6
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
Beach nearby, sun loungers
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
9.8 out of 10, Exceptional, 36 reviews
"Waterview cottage is comfortable and very clean. The accommodations look new and we had good sleep. The kitchen has most of the necessary equipment for meal preparation. A baking sheet pan is needed. WiFi and Roku TV was excellent. The primary bedroom bed was so tall/high my wife could not get in or out of it. That necessitated sleeping in the 2 twins. Plus, one of the twins was missing the top mini mattress. The view is mostly of the neighborhood street, nearby homes and their roofs and a small...
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
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The Heron's Nest at Atlantic Marina
Exterior
The Heron's Nest at Atlantic Marina
10.0 out of 10, Exceptional, 267 reviews
"Adorable cabin with an excellent view."
The Heron's Nest at Atlantic Marina
Directly Across from Gate One & Steps from the Waterfront
Fridge, microwave, oven, stovetop
Directly Across from Gate One & Steps from the Waterfront
10.0 out of 10, Exceptional, 180 reviews
"Charming spot in the heart of Annapolis, just a few moments walk from anything you might need."
Directly Across from Gate One & Steps from the Waterfront
Firefly Cottage at the Cape, HOT TUB, E.V. community beach, back yard fun
Property grounds
Firefly Cottage at the Cape, HOT TUB, E.V. community beach, back yard fun
10.0 out of 10, Exceptional, 61 reviews
"We had a great time at this very cute cottage and really appreciated the extra touches of the hosts, who were very helpful. The yard is truly a great place to hangout but there were also lots of places to enjoy close by."
Firefly Cottage at the Cape, HOT TUB, E.V. community beach, back yard fun
'At Fells Point' CitySide - 'Tons better than a hotel!'
'At Fells Point' CitySide - 'Tons better than a hotel!'
9.8 out of 10, Exceptional, 161 reviews
"This had everything we needed and Fells Point is a nice area!"
The price is ￥14,937
￥33,779 total
includes taxes & fees
Jun 5 - Jun 6
'At Fells Point' CitySide - 'Tons better than a hotel!'
A waterfront gem with dock, kayaks great water views. Sleeps up to 12.
Interior
A waterfront gem with dock, kayaks great water views. Sleeps up to 12.
9.8 out of 10, Exceptional, 14 reviews
"We really enjoyed our (much too short) stay at this waterfront gem!! The property was very clean, had all the amenities that we needed for our time away.... the only complaint is that we didn't have enough time to enjoy it all!! : ) thank you so much, we will be back!"
A waterfront gem with dock, kayaks great water views. Sleeps up to 12.
BAYSIDE BUNGALOW
Fridge, microwave, coffee/tea maker, toaster
BAYSIDE BUNGALOW
10.0 out of 10, Exceptional, 16 reviews
"We have been coming to Rock Hall for years and have stayed at the cottage the last two times and we have really enjoyed it. We will be back again and we will stay at this cottage again. My husband loves the sauna. Bill and Hannah"
The price is ￥27,515
￥42,832 total
includes taxes & fees
Jun 2 - Jun 3
BAYSIDE BUNGALOW
421 Irie: Simply Charming 2 Story Cottage!! Private Pool!! 1 Off Street Parking!
Fridge, microwave, oven, stovetop
421 Irie: Simply Charming 2 Story Cottage!! Private Pool!! 1 Off Street Parking!
10.0 out of 10, Exceptional, 81 reviews
"421Irie is a great property, well managed and maintained by Liz. It was perfect for a weekend of sailing, golf, family and friends. We hosted a small cookout for eight one night, and the cottage was just right for the group. The kitchen is well stocked, the big grill outside was just fine, and the multiple seating locations were ideal for the various attendees. We would love to stay at the cottage again next time we are in Annapolis"
421 Irie: Simply Charming 2 Story Cottage!! Private Pool!! 1 Off Street Parking!
Fully Equipped Docked Houseboat at Log Pond Marina in Havre de Grace, MD.
Property grounds
Fully Equipped Docked Houseboat at Log Pond Marina in Havre de Grace, MD.
9.2 out of 10, Wonderful, 10 reviews
"This was my second time to the houseboat and it was wonderful! It is conveniently located and many small shops, restaurants, brewery/bars are walking distance, and a short drive to wineries. Also a park right across from the marina."
Fully Equipped Docked Houseboat at Log Pond Marina in Havre de Grace, MD.
Cozy and peaceful BASEMENT in a house, close to different restaurants and a park
1 bedroom, iron/ironing board, WiFi, bed sheets
Cozy and peaceful BASEMENT in a house, close to different restaurants and a park
10.0 out of 10, Exceptional, 6 reviews
"I couldn’t have found a better place this gave us a great nights rest every night. We had a lot planned and all turned out great. Our first night we didn’t stop to eat so we asked Jimmy where we can go he directed us to a great Chinese restaurant. We were right smack in the middle of all our plans. Friday night An Inner Harbor Dinner Cruise. Saturday night a Kenny Chesney Concert. Sunday a Bowie Baysocks game and Monday on our way home stopped at the B&O Railroad Museum. What a great time thank...
The price is ￥12,264
￥19,000 total
includes taxes & fees
Jun 7 - Jun 8
Cozy and peaceful BASEMENT in a house, close to different restaurants and a park
Annapolis Condominium in the heart of the historic center
Property grounds
Annapolis Condominium in the heart of the historic center
9.8 out of 10, Exceptional, 249 reviews
"Great location"
Annapolis Condominium in the heart of the historic center
Beautiful Luxury waterfront Property,clean,Fully sterilized,Family oriented.
Property grounds
Beautiful Luxury waterfront Property,clean,Fully sterilized,Family oriented.
9.6 out of 10, Exceptional, 18 reviews
"Had a nice stay. We would definitalty book again."
Beautiful Luxury waterfront Property,clean,Fully sterilized,Family oriented.
Pool and Bay Views on wrap around deck in Kent Island
Outdoor pool
Pool and Bay Views on wrap around deck in Kent Island
9.6 out of 10, Exceptional, 21 reviews
"Everyone really loved the house and the location. The pool was great"
Pool and Bay Views on wrap around deck in Kent Island
Chesapeake Houseboat Getaway on Kent Island, Maryland
Property grounds
Chesapeake Houseboat Getaway on Kent Island, Maryland
10.0 out of 10, Exceptional, 7 reviews
"My husband and I and our dog had a lovely getaway on "Julia's Arc". This was our first time on a Houseboat and it was a wonderful experience. So much light! And the movement of the boat was just enough to be comforting. The home was very clean and beautifully adorned with great attention to detail. Julia, the host, was very responsive and very generous in doing all she could to make our trip as comfortable and pleasurable as possible. The views over the water were gorgeous and we really...
Chesapeake Houseboat Getaway on Kent Island, Maryland
Luxe Houseboat with Epic 360 Views of Baltimore Harbor
Property grounds
Luxe Houseboat with Epic 360 Views of Baltimore Harbor
10.0 out of 10, Exceptional, 6 reviews
"We had the best time staying at this property. What a location! Gorgeous and private! The boat is stunning, immaculate, and well appointed. The beds are amazing. Brian was a wonderful host and helped us through a minor glitch with the lockbox with dedicated speed. The supplemental information is unparalleled! Stay here!"
The price is ￥57,933
￥112,467 total
includes taxes & fees
Jun 3 - Jun 4
Luxe Houseboat with Epic 360 Views of Baltimore Harbor
Bay View Studio Apartment
Outdoor spa tub
Bay View Studio Apartment
10.0 out of 10, Exceptional, 25 reviews
"If you are looking for a very spacious well-appointed one bedroom apt. style accommodation in a residential setting with lovely waterfront bay views, I highly recommend this place!"
Bay View Studio Apartment
Milton Manor: W/D, WiFi, Free Street Parking
Private kitchen
Milton Manor: W/D, WiFi, Free Street Parking
2.0 out of 10, 2 reviews
"Good day! I want to first start off by saying thank you for allowing us to stay in your place. However, I do have so things I want to bring to you attention before I leave a review. 1) There is only one Tv in thee entire place when there are two rooms. 2) The Tv that is there doesn’t even work. 3) The sink doesn’t drain and had old water sitting in it. So, we had to brush our teeth in the shower. 4) Very noisy area. Cars come by all day and night. The neighbors above are very loud not to mention...
The price is ￥10,220
￥33,960 total
includes taxes & fees
Jun 5 - Jun 6
Milton Manor: W/D, WiFi, Free Street Parking
Waterfront Home with Private Dock, Eastern shore, Betterton Chestertown MD.
Property grounds
Waterfront Home with Private Dock, Eastern shore, Betterton Chestertown MD.
9.8 out of 10, Exceptional, 80 reviews
"House was fine. Odd they did not provide sheets. Was difficult for folks who came from far away. But the house was lovely and we enjoyed our time there!!"
Waterfront Home with Private Dock, Eastern shore, Betterton Chestertown MD.
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See all available 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.

Other types of properties in Chestertown you may be interested in

Comfort Inn & Suites Chestertown
Lobby
Comfort Inn & Suites Chestertown
2.5 star property
8.6 out of 10, Excellent, 677 reviews
"Breakfast area and food was below expectations"
The price is ￥20,588
￥22,853 total
includes taxes & fees
Jun 2 - Jun 3
Comfort Inn & Suites Chestertown
Red Roof Inn & Suites Chestertown
Suite, Multiple Beds, Non Smoking | Desk, laptop workspace, blackout drapes, iron/ironing board
Red Roof Inn & Suites Chestertown
2.0 star property
7.4 out of 10, Good, 271 reviews
"Property was OK, would stay again"
The price is ￥16,882
￥18,738 total
includes taxes & fees
Jun 5 - Jun 6
Red Roof Inn & Suites Chestertown
Historic Inns of Annapolis
Exterior
Historic Inns of Annapolis
3.5 star property
9.0 out of 10, Wonderful, 1,616 reviews
"Absolutely love these properties and the so-rounding area! Great places to eat and shop all within walking distance. "
The price is ￥23,999
￥30,953 total
includes taxes & fees
Jun 16 - Jun 17
Historic Inns of Annapolis
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.

Search for holiday rentals in Chestertown on Expedia! You can easily find your home rentals, villas, holiday apartments in Chestertown using one of the methods below:

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Look no further and take a look at our great range of rental properties in Chestertown!

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?

Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably: This vacation home rental outside of Chestertown offers a balcony, a garden, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 6 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Make the most of the spa tub in this rental home to help you unwind.

How many vacation rentals are there in Chestertown?

Expedia has 30 vacation rentals for your stay in Chestertown.

What can I see and do in Chestertown?

Cultural attractions include Historical Society of Kent County Maryland and Garfield Center for the Arts at the Prince Theater, whereas Wilmer Park is one spot to enjoy nature. Rolphs Wharf Marina and Crumpton Auction 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.

Recent reviews of Chestertown properties
Expedia verified reviews

Holiday Inn Express White Marsh, An IHG Hotel

Holiday Inn Express White Marsh, An IHG Hotel

5/5 Excellent
"They don’t tell you about paying a deposit until you get there… which was a big inconvenience!"
A verified traveler stayed at Holiday Inn Express White Marsh, An IHG Hotel
Posted 2 days ago
Holiday Inn Express White Marsh, An IHG Hotel