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Search Condo Rentals in Chestertown

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Compare Condo Rentals in Chestertown with updated reviews, rates, and availability.

Annapolis Condominium in the heart of the historic center
Deck view
Annapolis Condominium in the heart of the historic center
9.8 out of 10, Exceptional, (251)
"Perfect location to walk to the pre-wedding and wedding venues. The condo is very charming. The kitchen had everything we needed. The outdoor rooftop deck was amazing! Annapolis is a charming town and this condo was a good place to take it all in."
Annapolis Condominium in the heart of the historic center
BEACH WITHOUT THE BUSTLE
Aerial view of condo, beach and bay.
BEACH WITHOUT THE BUSTLE
10.0 out of 10, Exceptional, (22)
"We needed tranquility after returning from a deployment in the Mideast. All was perfect for my team and I."
BEACH WITHOUT THE BUSTLE
Unobstructed view of the Chesapeake Bay, w/ a beach!
Property grounds
Unobstructed view of the Chesapeake Bay, w/ a beach!
10.0 out of 10, Exceptional, (16)
"The property is really wonderful. The kitchen is well-equipped and clean, the beds are comfortable, as are the gathering spaces, the owner is extremely accommodating, and the view is hard to beat. We were one step away from a perfect stay as there had been a pet in the apartment prior to our visit, and this triggered one of our party's allergies. Once her medication kicked in, everyone was quite happy with our stay and would gladly return."
Unobstructed view of the Chesapeake Bay, w/ a beach!
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2939 Liberty Basement NEW!! · Convenient & Affordable Dundalk Studio!
2939 Liberty Basement NEW!! · Convenient & Affordable Dundalk Studio!
5.0 out of 10, (2)
"We were looking for a dog friendly flat on one level. The Dundalk location was good, and the overall condition of the flat was good, despite the tiny bathroom. Everything was fine except for the upstairs neighbors. We had no way of knowing that they would be a bunch of immature, loud young men. This almost ruined our stay!"
2939 Liberty Basement NEW!! · Convenient & Affordable Dundalk Studio!
Delightful little Historic District gem - for the antique lover and history buff.
View from entrance into living room and kitchen
Delightful little Historic District gem - for the antique lover and history buff.
9.0 out of 10, Wonderful, (4)
"Excellent location for all things USNA and downtown Annapolis. We walked everywhere. The second bedroom was a little warm but it was unseasonably hot while we were there. There is a K cup coffeemaker but you’ll need to bring everything to enjoy a cup. Would definitely stay again!"
Delightful little Historic District gem - for the antique lover and history buff.
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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, (53)
"Good location. House well stocked. Great pool. Short hike to river. Lots of kayaks ,a canoe and paddle boards"
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
9.8 out of 10, Exceptional, (6)
"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

Best Western Plus Hotel & Conference Center

Best Western Plus Hotel & Conference Center

5/5 Excellent
4-night family trip
"We just completed a 4-night family trip for Father's Day. With 2 young kids and an old dog, we had a great time! The rooms were comfortable and quiet, for the most part. Breakfast was good and the restaurant has pretty decent food for room-service. It's quick and not too pricey! There's a lot to do that's not too far away. We would definitely look here first if we ever take another trip to Baltimore."
A verified traveler stayed at Best Western Plus Hotel & Conference Center
Posted 6 hours ago
Best Western Plus Hotel & Conference Center