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Search Vacation Homes in Chestertown

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Compare 367 Vacation Homes in Chestertown with updated reviews, rates, and availability.

Fridge, microwave, oven, stovetop
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
10.0 out of 10, Exceptional, (3)
"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 $629
$1,417 total
includes taxes & fees
Jun 4 - Jun 5
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
4 bedrooms, desk, iron/ironing board, travel crib
Caribbean Pool Home <1 mile from Matapeake Beach!
10.0 out of 10, Exceptional, (1)
"The house was exactly as promised! We were very happy with the accommodations!"
The price is $253
$795 total
includes taxes & fees
May 28 - May 29
Caribbean Pool Home <1 mile from Matapeake Beach!
Fridge, microwave, coffee/tea maker, toaster
BAYSIDE BUNGALOW
10.0 out of 10, Exceptional, (16)
"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 $175
$271 total
includes taxes & fees
May 17 - May 18
BAYSIDE BUNGALOW
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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, (4)
"Mr Jimmy's place was great clean and just like the pics .....We would stay here again and again ..I loved the entertainment center 📺📺📺📺"
The price is $78
$121 total
includes taxes & fees
May 18 - May 19
Cozy and peaceful BASEMENT in a house, close to different restaurants and a park
Fridge, microwave, oven, stovetop
Charming Historic Townhouse Steps From USNA
10.0 out of 10, Exceptional, (12)
"My sister and I stayed while attending an event at the US Naval Academy. It was a quick, pleasant walk back and forth and always refreshing to come "home" and spend some quiet relaxing time together after a day out in town. Like a mini refuge!"
Charming Historic Townhouse Steps From USNA
Smart TV, DVD player, table tennis, music library
Hidden gem with water and golf course views! Bike ride to downtown!
10.0 out of 10, Exceptional, (25)
"Back in C’town to attend senior day lacrosse game and fish fry! Absolutely gorgeous, peaceful property close to town. Will definitely seek this place out for another adventure! 😀"
Hidden gem with water and golf course views! Bike ride to downtown!
Property grounds
Waterfront w/Deepwater Pier Walking Distance to Downtown Chestertown
10.0 out of 10, Exceptional, (84)
"This house is a gem! The property is fantastic, with such a beautiful backyard."
Waterfront w/Deepwater Pier Walking Distance to Downtown Chestertown
Fridge, microwave, oven, stovetop
Directly Across from Gate One & Steps from the Waterfront
10.0 out of 10, Exceptional, (179)
"This home is a charming and cozy historic property with a private courtyard in back with garden lights. The location is perfect right across from the Naval Academy and a couple blocks walk to the waterfront and center of town."
Directly Across from Gate One & Steps from the Waterfront
Property grounds
Riverfront home with multiple decks, central AC, washer/dryer - two dogs OK
10.0 out of 10, Exceptional, (31)
"Spotless. Cozy views of the water. We stayed here in March so we weren’t able to access the water but thoroughly enjoyed our stay. Convenient to everything’s we needed. Would definitely recommend."
Riverfront home with multiple decks, central AC, washer/dryer - two dogs OK
Pool
Grasonville Home w/ Private Pool on the Water
10.0 out of 10, Exceptional, (12)
"We were in town for a family wedding. The house was spotless, well-stocked and centrally located for our trip. We recommend the property and would come again!"
Grasonville Home w/ Private Pool on the Water
Property grounds
Glen Burnie Escape - Pet friendly with easy access to multiple attractions.
10.0 out of 10, Exceptional, (3)
"Convenient location. Nice house in quiet neighborhood. Spacious. Comfortable. Large sunroom. Wonderfully stocked. Lots of nice little amenities."
The price is $250
$325 total
includes taxes & fees
May 27 - May 28
Glen Burnie Escape - Pet friendly with easy access to multiple attractions.
Property grounds
Free parking Historic Union House Downtown with private patio
10.0 out of 10, Exceptional, (20)
"We were in town for a wedding, and this house was a wonderful place to stay for the festivities. There were 4 adults in our group. We were hardly at the house, so didn’t get to take advantage of some amenities. Beds were very comfortable, towels were large, soft, and plentiful. The house was well appointed and very clean. Only drawbacks were the small size of the downstairs bathroom, and distance to the parking garage. If you don’t need your car at all while in town, it’s not a big deal. If...
Free parking Historic Union House Downtown with private patio
Fridge, microwave, stovetop, dishwasher
Bright Townhome: Walk to Johns Hopkins Bayview!
10.0 out of 10, Exceptional, (8)
"The property was perfect for our party of 6. We were able to spread out and be comfortable. The house was very clean and the host was easily available when we had a question. We would definitely stay again."
Bright Townhome: Walk to Johns Hopkins Bayview!
Beach
Riverfront Country House on The Sassafras River
10.0 out of 10, Exceptional, (12)
"My family had a relaxing, fun weekend at the house. My 20-something children all loved the window seat where they curled up and read. We enjoyed time on the river with the kayaks and paddleboards. The beds were comfy, kitchen well stocked and overall the house is cozy. It was the perfect get-away for our family!"
The price is $500
$603 total
includes taxes & fees
May 17 - May 18
Riverfront Country House on The Sassafras River
TV, fireplace
Langford Creek Estate | Waterfront w/ HOT TUB + Deck!
10.0 out of 10, Exceptional, (3)
"Love the seclusion of the property and close proximity to the lake. Not to mention the nice amenities of the deck. Home was well equipped and overall we enjoyed our trip!"
Langford Creek Estate | Waterfront w/ HOT TUB + Deck!
Fridge, microwave, oven, stovetop
421 Irie: Simply Charming 2 Story Cottage!! Private Pool!! 1 Off Street Parking!
10.0 out of 10, Exceptional, (79)
"Excellent stay."
421 Irie: Simply Charming 2 Story Cottage!! Private Pool!! 1 Off Street Parking!
Property grounds
Waterfront Home with Private Dock, Eastern shore, Betterton Chestertown MD.
9.8 out of 10, Exceptional, (80)
"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.
Exterior
Relax on Kent Island in 3 Bedroom Home w/Waterview
9.8 out of 10, Exceptional, (19)
"We have nothing but great things to say about Adam and his beautiful home! He was so accommodating and the home was comfortable and spacious for our family of 5! Couldn’t have had a better experience :)"
The price is $156
$358 total
includes taxes & fees
May 27 - May 28
Relax on Kent Island in 3 Bedroom Home w/Waterview
Interior
Historic Annapolis Home 1.5 blocks from center of town.
9.8 out of 10, Exceptional, (19)
"We found the house as described and the location was excellent. We had some questions for the owner and he was responsive and helpful. Definitely a historic home. Really enjoyed the outdoor space."
Historic Annapolis Home 1.5 blocks from center of town.
Fridge, microwave, oven, stovetop
Fantastic Spacious Eastport Home Easy Walk to Everything & Parking for 6 Cars!
9.6 out of 10, Exceptional, (98)
"This property is ideal for a family. Very nicely decorated and ample room. The off street parking in Eastport is rare and makes this property well worth a stay."
Fantastic Spacious Eastport Home Easy Walk to Everything & Parking for 6 Cars!
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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 property types in Chestertown

Pool | Outdoor pool
350 Acre Waterfront Farm; High Speed Internet, Pool, Pickleball & Private Dock
10.0 out of 10, Exceptional, (50)
"Had an excellent time at this beautiful and secluded property on the Chester River. Although very private and a lot of outside space to roam, we were still very close to all that Chestertown has to offer. So, it was the best of both worlds. Plenty of amazing scenery and wildlife to enjoy around the property, and Beth is an excellent communicator. If you're a wine drinker, check out a number of close-by wineries like: Casa Carmen, Bu-De, Broken Spoke and Crow Vineyards. Would highly recommend...
350 Acre Waterfront Farm; High Speed Internet, Pool, Pickleball & Private Dock
Fridge, microwave, oven, stovetop
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
10.0 out of 10, Exceptional, (3)
"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 $629
$1,417 total
includes taxes & fees
Jun 4 - Jun 5
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
Exterior
The Heron's Nest at Atlantic Marina
10.0 out of 10, Exceptional, (264)
"Cute little cottage with a beautiful view! Forgot to account for the mini fridge with the food we brought, but besides that, everything went great for our short 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.

Chestertown Vacation Homes information

Number of reviews
570
Accommodation
367 Vacation Homes
Lowest Price
$78
Highest Price
$629

Recent reviews of Chestertown hotels
Expedia verified reviews