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

Caribbean Pool Home <1 mile from Matapeake Beach!
Gorgeous pool in gigantic fenced in backyard
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 AED 1,359
AED 3,466 total
includes taxes & fees
24 Jun - 25 Jun
Caribbean Pool Home <1 mile from Matapeake Beach!
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
Private Pier
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
10.0 out of 10, Exceptional, (5)
"The property was beautiful. The property manager was available for any inquiries we had. My family and I enjoyed it immensely. The view of the water was wonderful whether sitting on the dock or sitting in the sunroom. We played indoor and outdoor games. Perfect place for family bonding. The weather was perfect for our stay."
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
Directly Across from Gate One & Steps from the Waterfront
Private rear courtyard
Directly Across from Gate One & Steps from the Waterfront
10.0 out of 10, Exceptional, (181)
"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
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Cozy Cape Cod nestled in the heart of Rock Hall, sleeps 10 with pond view!
Exterior
Cozy Cape Cod nestled in the heart of Rock Hall, sleeps 10 with pond view!
10.0 out of 10, Exceptional, (2)
"Beautiful property, both inside and out, which was comfortable for two families with numerous children. Hosts were kind enough to make amenities beyond the usual available, including yard games, fishing rods, fire pit, and bicycles. We were VERY comfortable throughout our stay and were appreciative of everything this charming house had to offer. Three out of the four bedrooms had enough space for a crib, and the last still had a queen size bed that fit perfectly in the space with room to move...
Cozy Cape Cod nestled in the heart of Rock Hall, sleeps 10 with pond view!
Suburban Retreat Near Baltimore Harbor
Private kitchen
Suburban Retreat Near Baltimore Harbor
10.0 out of 10, Exceptional, (9)
"It was perfect for what I needed. Everything was clean"
Suburban Retreat Near Baltimore Harbor
Popular Historic Firehouse fully renovated with Parking and Pet Friendly
Comfortable furniture in the family room and a spiral staircase goes down to 1st floor bedroom/bath/laundry room.
Popular Historic Firehouse fully renovated with Parking and Pet Friendly
10.0 out of 10, Exceptional, (51)
"I stayed at this property for a family wedding this last weekend with 5 other adult family members. The original spot we booked fell through last second and I found this unique property. It fit our needs perfectly. There was plenty of space. Everything was clean. The outdoor sitting areas were an added bonus. Plenty of parking. And the location in relation to downtown were perfect. I’d definitely stay here again."
Popular Historic Firehouse fully renovated with Parking and Pet Friendly
Pet Friendly - Stone's throw from Annapolis City Dock with private back patio
Welcome to the Helm on Fleet!
Pet Friendly - Stone's throw from Annapolis City Dock with private back patio
9.8 out of 10, Exceptional, (7)
"Super close to all downtown amenities. Would definitely return."
Pet Friendly - Stone's throw from Annapolis City Dock with private back patio
A waterfront gem with dock, kayaks great water views. Sleeps up to 12.
Waterfront with private pier and great views
A waterfront gem with dock, kayaks great water views. Sleeps up to 12.
9.8 out of 10, Exceptional, (15)
"My friends, our wives, and kids loved our stay. Everything exceeded expectations. We especially enjoyed the backyard where we played yard games, grilled, and enjoyed the river."
A waterfront gem with dock, kayaks great water views. Sleeps up to 12.
350 Acre Waterfront Farm; High Speed Internet, Pool, Pickleball & Private Dock
Pool
350 Acre Waterfront Farm; High Speed Internet, Pool, Pickleball & Private Dock
10.0 out of 10, Exceptional, (52)
"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
Beautiful Luxury waterfront Property,clean,Fully sterilized,Family oriented.
Come Relax,Enjoy,Experience,drink,and have a Exciting joyful Vacation
Beautiful Luxury waterfront Property,clean,Fully sterilized,Family oriented.
9.6 out of 10, Exceptional, (18)
"Had a nice stay. We would definitalty book again."
Beautiful Luxury waterfront Property,clean,Fully sterilized,Family oriented.
BAYSIDE BUNGALOW
Exterior
BAYSIDE BUNGALOW
10.0 out of 10, Exceptional, (18)
"This is a excellent cottage for a short getaway. As the listing states, the cottage is small so only big enough for 1-2 people. There is a nice refrigerator and microwave to heat things up but no facilities for cooking. Paul and Chris are very friendly and helpful. Their dog Vinny is also friendly. We came for a triathlon and the porch was a covered so we could keep our bikes there. The sauna was also great to use after our triathlon."
The price is AED 643
AED 989 total
includes taxes & fees
13 Jun - 14 Jun
BAYSIDE BUNGALOW
Cozy and peaceful BASEMENT in a house, close to different restaurants and a park
Interior
Cozy and peaceful BASEMENT in a house, close to different restaurants and a park
10.0 out of 10, Exceptional, (7)
"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 AED 286
AED 444 total
includes taxes & fees
16 Jun - 17 Jun
Cozy and peaceful BASEMENT in a house, close to different restaurants and a park
Glen Burnie Escape - Pet friendly with easy access to multiple attractions.
Private kitchen
Glen Burnie Escape - Pet friendly with easy access to multiple attractions.
10.0 out of 10, Exceptional, (4)
"The pictures of this property don’t do it justice AT ALL. This house is amazing!!! It’s so cozy, spacious and stocked with so many amenities. The host was amazing to communicate with, the location was great and quiet. I could really go on and on about this property. I can’t wait to stay here again! Loved it so much!!"
The price is AED 918
AED 1,193 total
includes taxes & fees
25 Jun - 26 Jun
Glen Burnie Escape - Pet friendly with easy access to multiple attractions.
Entire Townhouse in Rock Hall
Exterior
Entire Townhouse in Rock Hall
10.0 out of 10, Exceptional, (16)
"We have stayed in this neighborhood before on a previous visit, we enjoyed how quiet and friendly the neighborhood is. We will definitely visit again. The house is very, very clean, cozy, and well stocked with all the supplies you could possibly need. We enjoyed sitting out in the evenings and watching the stars!!! Thanks for making our visit complete!!!"
Entire Townhouse in Rock Hall
Miller's Cottage
Property grounds
Miller's Cottage
10.0 out of 10, Exceptional, (24)
"We are from NY and had a major surgery at Johns Hopkins. Miller's Cottage was the perfect location for us to spend the week post-op prior to returning home to NY. Miller's cottage was clean, comfortable and very well equipped. There was outside seating which allowed us to enjoy the fresh air while recovering."
Miller's Cottage
Close to US Naval Academy, downtown Annapolis, Maryland Live Casino, BWI Airport
Property grounds
Close to US Naval Academy, downtown Annapolis, Maryland Live Casino, BWI Airport
10.0 out of 10, Exceptional, (7)
"We had a family reunion in the area and my brother, and I and our spouses spent 4 nights. It was a perfect fit for our needs. Extremely clean and well appointed. Even the coffee was great. Thanks so much."
Close to US Naval Academy, downtown Annapolis, Maryland Live Casino, BWI Airport
Johns Hopkins Historic Renovated home - Location!
Room
Johns Hopkins Historic Renovated home - Location!
10.0 out of 10, Exceptional, (2)
"Beautiful historic home"
The price is AED 533
AED 1,147 total
includes taxes & fees
10 Jul - 11 Jul
Johns Hopkins Historic Renovated home - Location!
421 Irie: Simply Charming 2 Story Cottage!! Private Pool!! 1 Off Street Parking!
Exterior
421 Irie: Simply Charming 2 Story Cottage!! Private Pool!! 1 Off Street Parking!
10.0 out of 10, Exceptional, (83)
"421 Irie was the perfect perch in Annapolis for our son's wedding weekend, exceeding all of our expectations. Liz made us feel incredibly welcome from the moment we booked with her lightning-quick responses, warm hospitality, and thoughtful personal touches. The home was immaculate and had every amenity we could have wished for. Its convenient location made it easy for us to navigate to and from wedding events, while the comfort and coziness of the house made it the ideal place to relax and...
421 Irie: Simply Charming 2 Story Cottage!! Private Pool!! 1 Off Street Parking!
Waterfront Home with Private Dock, Eastern shore, Betterton Chestertown MD.
Front of House Facing the Water.
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.
Historic Annapolis Home 1.5 blocks from center of town.
Exterior
Historic Annapolis Home 1.5 blocks from center of town.
9.8 out of 10, Exceptional, (20)
"The house was super cute and the host was great!"
Historic Annapolis Home 1.5 blocks from center of town.
Don't see what you're looking for?
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

350 Acre Waterfront Farm; High Speed Internet, Pool, Pickleball & Private Dock
Pool
350 Acre Waterfront Farm; High Speed Internet, Pool, Pickleball & Private Dock
10.0 out of 10, Exceptional, (52)
"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
Private Pier
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
10.0 out of 10, Exceptional, (5)
"The property was beautiful. The property manager was available for any inquiries we had. My family and I enjoyed it immensely. The view of the water was wonderful whether sitting on the dock or sitting in the sunroom. We played indoor and outdoor games. Perfect place for family bonding. The weather was perfect for our stay."
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
Beach
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
9.8 out of 10, Exceptional, (36)
"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
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.

Recent reviews of Chestertown hotels
Expedia verified reviews

La Quinta Inn & Suites by Wyndham Baltimore S. Glen Burnie

La Quinta Inn & Suites by Wyndham Baltimore S. Glen Burnie

5/5 Excellent
"💯💪"
A verified traveler stayed at La Quinta Inn & Suites by Wyndham Baltimore S. Glen Burnie
Posted 2 days ago
La Quinta Inn & Suites by Wyndham Baltimore S. Glen Burnie