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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
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
Miscellaneous

Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!

10.0 out of 10, Exceptional, (205)
"A great experience all around"
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
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, (23)
"Fifteen ladies from my church stayed at this Vrbo for a weekend conference in Annapolis. We enjoyed the property and the house! We had a beautiful weekend and even got on the water, played pickle ball, and enjoyed the views. The house is beautiful! The kitchen is well stocked and the house is comfortable and there is plenty of parking. Since it was November, the heated sunroom floors were a wonderful bonus. Thank you for the memories and a wonderful stay!"
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
'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, (181)
"2nd time here and love it! "
The price is HK$683
HK$1,579 total
includes taxes & fees
6 Jan - 7 Jan 2025
'At Fells Point' CitySide - 'Tons better than a hotel!'
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, (75)
"We had a great two days here! House has everything you need. We really enjoyed the hot tub! We were lucky the weather was so warm and we could just sit outside all day looking at the water and end the day with gorgeous sunsets. We would definitely come back!"
Waterfront Cabin With Spectacular Sunsets Overlooking The Chesapeake Bay
A waterfront gem with dock, kayaks great water views. Sleeps up to 12.
Smart TV, books

A waterfront gem with dock, kayaks great water views. Sleeps up to 12.

10.0 out of 10, Exceptional, (24)
"Very nice house to stay for the holiday. Perfect layout. Great communication with the owners. View gorgeous. "
A waterfront gem with dock, kayaks great water views. Sleeps up to 12.
Relax on Kent Island in 3 Bedroom Home w/Waterview
Marina

Relax on Kent Island in 3 Bedroom Home w/Waterview

9.8 out of 10, Exceptional, (32)
"Perfect for our weekend stay. Checkin was easy and communication with the owner was great! Definitely would stay again. Kentmoor restaurant was awesome. Filled with locals who were friendly and welcoming! Food was great!"
The price is HK$644
HK$2,025 total
includes taxes & fees
12 Jan - 13 Jan 2025
Relax on Kent Island in 3 Bedroom Home w/Waterview
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
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, (28)
"This VRBO is in a great neighborhood down by Baltimore's harbor, close to trendy Fells Point. Walking distance to everything. The home is quite large and was in excellent shape. Ray was a very accommodating host. Communication with him was great, and we had no complaints."
Beautiful Luxury waterfront Property,clean,Fully sterilized,Family oriented.
Firefly Cottage at the Cape, community beach, Hot tub, USNA games, Holidays,
Exterior

Firefly Cottage at the Cape, community beach, Hot tub, USNA games, Holidays,

10.0 out of 10, Exceptional, (82)
"A very nice and well-maintained cottage in the Cape St. Clair neighborhood where family members live. The owners have done a great job of provisioning the cottage both inside and outside, for recreational opportunities and enjoyment (barbecuing and relaxing). The backyard is very large and great for games provided with the property, like corn hole. There is also a hot tub. The owners have found the right balance for being responsive when you need them, while leaving you in peace otherwise....
Firefly Cottage at the Cape, community beach, Hot tub, USNA games, Holidays,
Waterfront w/upper sundeck and private pier located near Rock Hall, sleeps 18.
Fridge, microwave, oven, stovetop

Waterfront w/upper sundeck and private pier located near Rock Hall, sleeps 18.

9.8 out of 10, Exceptional, (50)
" We ( a group of 16 women) enjoyed having our annual retreat at Nauti or Knot. We stayed for a weekend and the accommodations could not have been better! The bedrooms and bathrooms were wonderful. The living room was able to sit 16 comfortably and the dining room table was big enough for all of us to have dinner together. This is an excellent house!! Our only complaint and it’s minor is that the freezer door was really hard to open."
Waterfront w/upper sundeck and private pier located near Rock Hall, sleeps 18.
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, (267)
"I booked this property for a girls weekend with my college roommates and we had the BEST time. The location is great; right off the main shopping/restaurant area. Also the bedroom layouts (4 single beds & 1 queen) made it easy to accommodate and sleep the 6 of us. Christina was great & easy to contact. We’d love to come back in the summer! Highly recommend this spot. "
Annapolis Condominium in the heart of the historic center
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.
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)
"Felt like home as soon as we walked in...except it was CLEANER than home :-) Comfortable, spacious, well-stocked. Hosts were attentive & quick to answer messages. Great experience!"
Excellent Location, Super Clean, Super Spacious, Near Bay & Downtown Annapolis
Amazing views, short walks to great dining!
View from property

Amazing views, short walks to great dining!

10.0 out of 10, Exceptional, (76)
"Very well-maintained property in a quiet neighborhood. Although we didn't need anything, host was always available."
Amazing views, short walks to great dining!
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, (102)
"Awesome House Awesome neighborhood Awesome Host(ess). 10 out of 10"
The price is HK$3,107
HK$4,029 total
includes taxes & fees
12 Jan - 13 Jan 2025
421 Irie: Simply Charming 2 Story Cottage!! Private Pool!! 1 Off Street Parking!
USNA Quintessential Charm ~ Downtown Annapolis.
Fridge, microwave, oven, stovetop

USNA Quintessential Charm ~ Downtown Annapolis.

9.8 out of 10, Exceptional, (7)
"We really enjoyed this property. It was clean and tidy. Checking in was simple. Parking was straightforward once we noticed the markers giving us clear instructions. The kitchen has everything you need. I stayed in the downstairs bedroom, and the bed and pillows were very comfortable. The downstairs shower is small, but the water pressure is good. Everyone who stayed upstairs enjoyed the amenities. Definitely will try to rent this again for the next time we visit Annapolis."
The price is HK$1,351
HK$3,285 total
includes taxes & fees
29 Dec - 30 Dec
USNA Quintessential Charm ~ Downtown Annapolis.
Renovated Row Home in the heart of Downtown Annapolis.Two blocks to everything
Fridge, microwave, oven, stovetop

Renovated Row Home in the heart of Downtown Annapolis.Two blocks to everything

9.6 out of 10, Exceptional, (12)
"The home was wonderfully situated in Annapolis. Will is terrific and a helpful communicator as property owner. We enjoyed our Thanksgiving away! Many thanks. "
Renovated Row Home in the heart of Downtown Annapolis.Two blocks to everything
Freshly renovated 3-story home 1 block from USNA!
Fridge, microwave, oven, stovetop

Freshly renovated 3-story home 1 block from USNA!

10.0 out of 10, Exceptional, (28)
"What a fantastic location, central to everything in the city. Parked the car and walked everywhere. The house is perfect!!"
The price is HK$1,150
HK$4,952 total
includes taxes & fees
2 Jan - 3 Jan 2025
Freshly renovated 3-story home 1 block from USNA!
The Heron's Nest at Atlantic Marina
Exterior

The Heron's Nest at Atlantic Marina

10.0 out of 10, Exceptional, (286)
"We booked this property, along with the other property at the marina for our wedding weekend and WOW - we LOVED our stay. The views from this cute little cottage are phenomenal. We woke up each morning to watch the sunrise. The hosts were extremely accommodating and even helped secure our cake topper that we accidentally left behind in the whirlwind of check-out. This was the perfect spot for our first look as well. I would highly recommend booking this place for a cute romantic stay!"
The Heron's Nest at Atlantic Marina
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, (735)
"Front desk staff was welcoming and friendly. We had a suite so I am guessing it was a bit larger than a regular room but it was really wonderful to have the extra space. The room was clean and the breakfast was decent (the coffee was good for hotel coffee). Would certainly stay here again when I am in the area. "
The price is HK$794
HK$881 total
includes taxes & fees
1 Jan - 2 Jan 2025
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
7.4 out of 10, Good, (322)
"Staff was very friendly "
The price is HK$531
HK$590 total
includes taxes & fees
1 Jan - 2 Jan 2025
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?

350 Acre Waterfront Farm; High Speed Internet, Pool, Pickleball & Private Dock : This highly rated holiday home rental in Chestertown is located on a lake, and has an outdoor pool, a fireplace and a BBQ to put you at ease in your new surroundings. It has 4 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 26 holiday rentals for your stay in Chestertown.

What can I see and do in Chestertown?

Enjoy the outdoors at Wilmer Park and Rolling Road Park, or simply take in cultural attractions like Historical Society of Kent County Maryland and Garfield Center for the Arts at the Prince Theater. 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.