Photo by Patricia Knorr

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Compare 11 Condo Rentals in Chester with updated reviews, rates, and availability.

Downtown Annapolis Condo w/ Free Parking + Coffee

10.0 out of 10, Exceptional, (19)
"Great condominium at a great location. Reserved parking. We were impressed with the owners’ approach—a lot of very nice small details. Beautifully decorated. "
Downtown Annapolis Condo w/ Free Parking + Coffee

Annapolis Condominium in the heart of the historic center

9.8 out of 10, Exceptional, (269)
"This property is just steps from Main Street. It was the perfect location for exploring town and enjoying all that Annapolis had to offer during the holiday season. "
Annapolis Condominium in the heart of the historic center

Book for CW 2025 Walk to Main Street restaurants and shops from waterfront Condo w Pool and Parking

10.0 out of 10, Exceptional, (15)
"The property was outstanding in proximity to the USNA and downtown Annapolis. We were able to walk to a fabulous bakery and good restaurants. The apartment was well appointed. The King-sized bed was exceptionally comfortable. We will return to this location!"
Book for CW 2025 Walk to Main Street restaurants and shops from waterfront Condo w Pool and Parking

Beautiful Condo - Water View Near City Dock

9.6 out of 10, Exceptional, (140)
"I currently live in this complex, and I rented this condo for my parents to come stay a few days while I recovered from surgery. Joe and Beth were extremely accommodating and kept communication with my parents while they stayed (but also didn't bug them!). I was thankful to have such an easy process for my older parents and they are already talking about coming back down again because they enjoyed their stay so much!"
Beautiful Condo - Water View Near City Dock

Prime Viewing for Blue Angels -Rooftop Deck and Water Views of Spa Creek!

10.0 out of 10, Exceptional, (9)
"We enjoyed our visit with our son at USNA. Easy walk to DTA and great restaurants in Eastport. View from rooftop was spectacular!! Beds were comfortable."
Prime Viewing for Blue Angels -Rooftop Deck and Water Views of Spa Creek!

Chic Condo w/ Balcony in the Heart of Annapolis!

9.8 out of 10, Exceptional, (55)
"We have stayed in this building 3 times, and the location and the set up of the units are excellent. The complex is safe, quiet and is in a great location. It also is very accessible for handicap and having a secure parking spot is advantageous. "
Chic Condo w/ Balcony in the Heart of Annapolis!

Unbelievable beach views for 6

2.0 star property
10.0 out of 10, Exceptional, (6)
"This was our 5th trip to North Beach and our 4th time at a condo in Southwinds, and we have never been disappointed. Jenn and Mike, our hosts this time, provided all the information we needed to feel comfortable in their home. We found it exactly as pictured. NB has 5 good restaurants within walking distance and at least 2 more within a 5 minute drive. The boardwalk is great for walking at anytime of day. The new library is a jewel with special sections for all ages and a “makers” room. Teens...
Unbelievable beach views for 6

Kent Island Waterfront Cottage

9.4 out of 10, Exceptional, (8)
"My husband and I stayed here for a quick weekend getaway to celebrate our anniversary. We appreciated the host being able to accommodate us an earlier check in and later check out time to maximize our short time away. They only charged us a small fee. The place was clean. So clean that I didn't feel I needed to wipe anything down, which is usually the case when we go to other places. The view was stunning and we had nice weather. We loved being able to walk out onto the dock as well as sit out...
Kent Island Waterfront Cottage

Waterfront 2-Bedroom Condo on Spa Creek

10.0 out of 10, Exceptional, (7)
"This is a great location. Walking distance to everything. Near all the sailing clubs! Property manager was the best we have ever experienced."
Waterfront 2-Bedroom Condo on Spa Creek

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.

Unique 2-Bedroom Condo in Renovated Church Parish House

Unique 2-Bedroom Condo in Renovated Church Parish House
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 property types in Chester

Waterfront Sunset Bayview: sleeps 6

10.0 out of 10, Exceptional, (12)
"Great house, great owner, family had a blast! Thank you!"
Waterfront Sunset Bayview: sleeps 6

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

10.0 out of 10, Exceptional, (210)
"We loved our visit to Annapolis, and our stay at 10 Randall was all that we’d imagined it would be.We wish the weather has been a tad warmer, but I don’t think John could have fixed that .We highly recommend this charming home."
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!

240' Private Beachfront @Kent Island Love Point - Great for Large Groups

10.0 out of 10, Exceptional, (180)
"This house was so cozy yet spacious! The house was amply stocked with just about everything you would want or need. The owner responded to our inquiries immediately! I hope we go back there again! "
240' Private Beachfront @Kent Island Love Point - Great for Large Groups
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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