Photo by Patricia Knorr

Search Condo Rentals in Chester

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Compare 10 Condo Rentals in Chester with updated reviews, rates, and availability.

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
Chic Condo w/ Balcony in the Heart of Annapolis!
9.8 out of 10, Exceptional, (43)
"Everything at this property was wonderful with one big exception. The owner provides you with only one FOB to enter the building. We had 4 adults coming and going at all different hours. It was hectic to “trade off” the FOB to enter the condo. This was very INCONVENIENT when members of our family would go to the condo to take a nap and then have to be woken up to let the rest of the group in. We had plenty of occurrences like this."
Chic Condo w/ Balcony in the Heart of Annapolis!
Waterfront 2-Bedroom Condo on Spa Creek
Waterfront 2-Bedroom Condo on Spa Creek
Save an average of 15% on thousands of hotels when you're signed in
Pool, Parking and Walk to Main Street from Waterfront Condo
10.0 out of 10, Exceptional, (8)
"I lived in the Annapolis area for 2 decades in my 50s and 60s. This property is a true slice of the good life in Annapolis - upscale but family friendly location, with top-notch restaurants within walking distance (2-5 blocks) waterview with charming glimpses of the capitol dome and St Mary's church steeple, boats and paddlers going by for entertainment, boat tours and adventures nearby. The unit is newly renovated/updated, as pictured but even better in person."
Pool, Parking and Walk to Main Street from Waterfront Condo
Downtown Annapolis Condo w/ Free Parking + Coffee
10.0 out of 10, Exceptional, (12)
"All in one word - spoiled!! Accommodations, Location, amenities, everything was perfect!"
Downtown Annapolis Condo w/ Free Parking + Coffee
Beautiful Condo - Water View Near City Dock
9.6 out of 10, Exceptional, (128)
"This property was perfect for what we needed! It's small but that's all we needed for 2 of us. The view from the rooftop was amazing and we spent every morning and evening up there watching the sunrise/sunset."
Beautiful Condo - Water View Near City Dock
Eastport Condo in Building with Rooftop Water Views of Spa Creek!
10.0 out of 10, Exceptional, (6)
"Very good except for toilet problems"
Eastport Condo in Building with Rooftop Water Views of Spa Creek!
Luxury Waterfront home with private pier and guest house
10.0 out of 10, Exceptional, (3)
Luxury Waterfront home with private pier and guest house
Water-view condo with rooftop pool & balcony - minutes from downtown
10.0 out of 10, Exceptional, (4)
Water-view condo with rooftop pool & balcony - minutes from downtown
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.
Don't see what you're looking for?
See all available properties in Chester
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 Chester

Kent Island Time - Enjoy Kent Island Waterfront-Pet Friendly!
10.0 out of 10, Exceptional, (6)
"My sisters and I (5 total) visited in early November. Kent Island Time was a perfect fit. We were impressed by the cleanliness, spacious rooms, and well-equipped common areas. The best feature was the waterfront location. Even in November, we were able to sit outside on the patio and enjoy a glass of wine as we watched the amazing sunset. We all agreed we would absolutely stay again in the future."
Kent Island Time - Enjoy Kent Island Waterfront-Pet Friendly!
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
Cozy place close to the city dock
10.0 out of 10, Exceptional, (55)
"We enjoyed our 2 nights at Cozy Place Close to the docks. Easy access and personalized connection with Nathalie were appreciated! We enjoyed the French and sail boating themes in the apartment, aligned the Annapolis maritime history! The docks are a short drive and old Town Annapolis was pleasant and historical! We recommend Cozy Place to others!"
Cozy place close to the city 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.

Recent reviews of Chester hotels
Expedia verified reviews