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Chestertown Holiday Rentals

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Holiday Rentals in Chestertown

350 Acre Waterfront Farm; High Speed Internet, Pool, Pickleball & Private Dock
Outdoor pool
350 Acre Waterfront Farm; High Speed Internet, Pool, Pickleball & Private Dock
10.0 out of 10, Exceptional, (61)
"Great!"
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, (20)
"Our annual girls weekend was held at this property. The house was perfect. there were enough beds and Comfortable relaxing places to sit and view the lake relax around the pool Or just sit quietly and read a book. The property manager, Erin Was so helpful through the entire process And I do think the pictures did not do justice to the lovely appointed decor. "
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
Directly Across from Gate One & Steps from the Waterfront
Miscellaneous
Directly Across from Gate One & Steps from the Waterfront
10.0 out of 10, Exceptional, (200)
"Incredible location! The process was easy and the house completely suited our needs! We would definitely stay again!"
Directly Across from Gate One & Steps from the Waterfront
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, (44)
"it being off season,very quiet. the people in the surrounding neighborhood were very friendly, we had a great time, ash and christine were awsome host. we will deffinately go back again!"
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
'At Fells Point' CitySide - 'Tons better than a hotel!'
Marina
'At Fells Point' CitySide - 'Tons better than a hotel!'
9.8 out of 10, Exceptional, (175)
"Super cute department. Has everything that you need and is very comfortable. Lots of super cute touches. In an awesome neighborhood, super walkable and close to all of the fun things and Fells Point."
The price is HK$684
HK$1,580 total
includes taxes & fees
19 Nov - 20 Nov
'At Fells Point' CitySide - 'Tons better than a hotel!'
Firefly Cottage at the Cape, community beach, Hot tub USNA, pets, Holidays, Fun
Exterior
Firefly Cottage at the Cape, community beach, Hot tub USNA, pets, Holidays, Fun
10.0 out of 10, Exceptional, (79)
"Firefly Cottage is a wonderful cottage! It’s clean, beautifully decorated, has high quality linens & finishes & fabulous outdoor living spaces. Pat & Ken’s hospitality & thoughtfulness helped to make our stay just perfect. "
Firefly Cottage at the Cape, community beach, Hot tub USNA, pets, Holidays, Fun
Charming garden row home, easy 4 block walk to the heart of Annapolis.
Exterior
Charming garden row home, easy 4 block walk to the heart of Annapolis.
10.0 out of 10, Exceptional, (108)
"We have stayed at this property multiple times since we have a son at the Naval Academy. This place is beautiful, well appointed and comfortable. The hosts are very responsive and they go out of their way to make their guests feel extra special- we will be back. "
Charming garden row home, easy 4 block walk to the heart of Annapolis.
Beautiful Luxury waterfront Property,clean,Fully sterilized,Family oriented.
Terrace/patio
Beautiful Luxury waterfront Property,clean,Fully sterilized,Family oriented.
9.4 out of 10, Exceptional, (23)
"We had a great stay. Ray, the host was easy to communicate with and very hands-on and helpful. The place exceeded expectations. Really a lot of room. The garage was nice to have. Only thing the Rooftop deck needs some sprucing up and some better outdoor furniture. Otherwise the place was Great."
Beautiful Luxury waterfront Property,clean,Fully sterilized,Family oriented.
Waterfront w/private pier located near Rock Hall, REMODEDLED and ENLARGED for 16
Fridge, microwave, stovetop, dishwasher
Waterfront w/private pier located near Rock Hall, REMODEDLED and ENLARGED for 16
10.0 out of 10, Exceptional, (47)
"Beautiful views and spacious comfortable living space. Well supplied kitchen. "
Waterfront w/private pier located near Rock Hall, REMODEDLED and ENLARGED for 16
Chesapeake Houseboat Getaway on Kent Island, Maryland
Marina
Chesapeake Houseboat Getaway on Kent Island, Maryland
9.6 out of 10, Exceptional, (20)
"We loved our stay. It was particularly nice to get away from all the "hustle and bustle" of the Sailboat Show. The unit was well-equipped and comfortable. We loved the upper deck! In fact, we had morning coffee, on day, and watched 2 eagles in a nearby tree. "
Chesapeake Houseboat Getaway on Kent Island, Maryland
Waterfront house with amazing views. Top of the Chesapeake
On the beach, sun-loungers, beach towels
Waterfront house with amazing views. Top of the Chesapeake
10.0 out of 10, Exceptional, (94)
"Cute, up-to-date house, peaceful location, beautiful views. Well supplied kitchen, including sharp knives! Excellent communication with owner – prompt and helpful. Fast internet. Could use more bathroom surface areas; a few more hooks to hang clothes and towels; and an additional umbrella or two outside for shade. My mom, sister, and I thoroughly enjoyed our stay."
Waterfront house with amazing views. Top of the Chesapeake
Cass-N-Reel Luxury Houseboat
Smart TV
Cass-N-Reel Luxury Houseboat
10.0 out of 10, Exceptional, (17)
"Bought it for friends and didn't stay myself. They said it was perfect."
The price is HK$933
HK$2,298 total
includes taxes & fees
27 Nov - 28 Nov
Cass-N-Reel Luxury Houseboat
Firepit, Beach, Pier and Gorgeous views without leaving your home ! ! !
Lake
Firepit, Beach, Pier and Gorgeous views without leaving your home ! ! !
9.4 out of 10, Exceptional, (87)
"This was our 1st time in Maryland. We wanted a place on the water and that was able sleeps 8 adults and 5 children ages 5-16 comfortably. This home was perfect! The home was situated on the lake with a dock. It had 5 bedrooms (4 bedrooms with king size beds) and a sleeper in the living room area. Plenty of beach towels, fishing rods, access to canoe and kayak. Easy communication with owner and hassle free check-in. We would return and recommend this home to anyone looking for a relaxing...
Firepit, Beach, Pier and Gorgeous views without leaving your home ! ! !
Annapolis Condominium in the heart of the historic center
Terrace/patio
Annapolis Condominium in the heart of the historic center
9.8 out of 10, Exceptional, (264)
"Great location, clean, excellent communication with owner. Everything we needed for a perfect trip to Annapolis."
Annapolis Condominium in the heart of the historic center
Exceptional River Front Family Retreat! - Dock, Private Beach & Bungalows
Exterior
Exceptional River Front Family Retreat! - Dock, Private Beach & Bungalows
10.0 out of 10, Exceptional, (51)
"The house is roomy and was clean and well stocked."
Exceptional River Front Family Retreat! - Dock, Private Beach & Bungalows
Excellent Location, Super Clean, Super Spacious, Near Bay & Downtown Annapolis
Miscellaneous
Excellent Location, Super Clean, Super Spacious, Near Bay & Downtown Annapolis
9.8 out of 10, Exceptional, (27)
"We were in Annapolis for a wedding and we had 14 members of our family coming from all over. The house was perfect and the host could not have been more accommodating It was a quick 14 minutes to downtown Annapolis and there were a number of small stores 1/2 mile from the house. My only regret was that we did not book an extra day to just enjoy the house and the area. . "
Excellent Location, Super Clean, Super Spacious, Near Bay & Downtown Annapolis
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, (24)
"We loved everything about the Kent Island House! Would book again in a hot minute"
Pool and Bay Views on wrap around deck in Kent Island
USNA Quintessential Charm ~ Downtown Annapolis.
Fridge, microwave, oven, stovetop
USNA Quintessential Charm ~ Downtown Annapolis.
9.8 out of 10, Exceptional, (6)
"Limited living room seating for family of 5"
The price is HK$1,477
HK$3,448 total
includes taxes & fees
11 Nov - 12 Nov
USNA Quintessential Charm ~ Downtown Annapolis.
Waterfront Cabin With Spectacular Sunsets Overlooking The Chesapeake Bay
Terrace/patio
Waterfront Cabin With Spectacular Sunsets Overlooking The Chesapeake Bay
10.0 out of 10, Exceptional, (74)
"The property and Sue are amazing! Perfect weekend getaway. 10 out of 10!! "
Waterfront Cabin With Spectacular Sunsets Overlooking The Chesapeake Bay
Amazing views, short walks to great dining!
View from property
Amazing views, short walks to great dining!
10.0 out of 10, Exceptional, (72)
"The place is very comfortable and tucked away on the creek with nice water views. The host was accessible but I didn’t need a thing! The screened porch is a wonderful spot to enjoy my scone and tea fresh from the Great Harvest bakery just up the road. The golden sunset was a bonus each evening. "
Amazing views, short walks to great dining!
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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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, (723)
"Very clean and comfortable home away from home, and breakfast in the morning, too. Perfect place to stay to enjoy the Sultana Downrigging Festival, just a short drive away. And, Chestertown is a beautiful and friendly town, too!"
The price is HK$829
HK$920 total
includes taxes & fees
4 Dec - 5 Dec
Comfort Inn & Suites Chestertown
Red Roof Inn & Suites Chestertown
Desk, laptop workspace, blackout curtains, iron/ironing board
Red Roof Inn & Suites Chestertown
2.0 star property
7.2 out of 10, Good, (316)
"Room was ok, needed a little maintenance and TLC but was clean. Pool was closed indefinitely, and only 1 ice machine for the whole hotel. Doesn't appear owners are putting much $ into the place to keep it up."
The price is HK$615
HK$683 total
includes taxes & fees
2 Dec - 3 Dec
Red Roof Inn & Suites Chestertown
350 Acre Waterfront Farm; High Speed Internet, Pool, Pickleball & Private Dock
Outdoor pool
350 Acre Waterfront Farm; High Speed Internet, Pool, Pickleball & Private Dock
10.0 out of 10, Exceptional, (61)
"Great!"
350 Acre Waterfront Farm; High Speed Internet, Pool, Pickleball & Private Dock
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.

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?

Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably: This holiday home rental outside of Chestertown offers a balcony, a garden and a BBQ 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 that you can cook with friends or family. Make the most of Access to hot tub in this rental home to help you unwind.

How many holiday rentals are there in Chestertown?

Expedia has 30 holiday 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 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.