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

Property grounds
Walk to Main Street from Waterfront Condo with pool and parking
10.0 out of 10, Exceptional, (7)
"In an older apartment building, this condo is situated over the creek with views to the bridge and beyond. Everything is new and I would highly recommend."
Walk to Main Street from Waterfront Condo with pool and parking
Interior
Chic Condo w/ Balcony in the Heart of Annapolis!
10.0 out of 10, Exceptional, (41)
"The owner responded to emails promptly- the place was extremely clean and well decorated. The amount of extras was amazing- hair dryers, steamers, free coffee, soaps, paper towels, etc. thank you!"
Chic Condo w/ Balcony in the Heart of Annapolis!
TV
Water-view condo with rooftop pool & balcony - minutes from downtown
10.0 out of 10, Exceptional, (2)
Water-view condo with rooftop pool & balcony - minutes from downtown
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Pool
Eastport Condo in Building with Rooftop Water Views of Spa Creek!
10.0 out of 10, Exceptional, (5)
"Small place but perfect for 2 people wanting to go to the boat show as it is a 10 minute walk away and comes with an assigned parking spot."
Eastport Condo in Building with Rooftop Water Views of Spa Creek!
Fridge, microwave, oven, stovetop
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
Property grounds
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
Property grounds
Annapolis Condominium in the heart of the historic center
9.8 out of 10, Exceptional, (248)
"Great location"
Annapolis Condominium in the heart of the historic center
Property grounds
Beautiful Condo - Water View Near City Dock
9.6 out of 10, Exceptional, (127)
"Location location location! This comfortable condo is in our favorite part of Annapolis, Eastport, just across the drawbridge from Main Street, Ego Alley, and the USNA. It is a great destination for walkers (and others - free easy parking). We made use of the kitchen for a couple of dinners. There are also amazing views from the rooftop. Thanks!"
Beautiful Condo - Water View Near City Dock
Fridge, microwave, oven, stovetop
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.
Fridge, microwave, oven, stovetop
Waterfront 2-Bedroom Condo on Spa Creek
Waterfront 2-Bedroom Condo on Spa Creek
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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 Chester

Interior
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!
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
Fridge, microwave, oven, stovetop
Directly Across from Gate One & Steps from the Waterfront
10.0 out of 10, Exceptional, (180)
"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
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.

Chester Condo Rentals information

Number of reviews
365
Accommodation
10 Condo Rentals
Lowest Price
Highest Price

Frequently asked questions

Why book your condo in Chester with Expedia?
We think that vacations shouldn’t be complicated, so if you’re on the lookout for condos at the perfect price, Expedia delivers. Stick to the budget and go for something small and cozy, or book a 5-star condo and spoil the ones you love most. Use our convenient search filters to find an escape in Chester that fits your needs.
How can I find cheap condos in Chester?
The best way to locate cheap condos in Chester is with Expedia’s handy filter tool. Narrow your search by amenities, budget and star rating to access unbeatable deals in just a few clicks.
What is there to do in Chester near my condo?
Chester has enough sights and activities to keep you going for weeks (or months!), starting with Sandy Point State Park. Sandy Point Beach, Matapeake State Park and Love Point State Park are other impressive attractions. If you’re in town a while, Bay Ridge Beach and Queenstown Harbor Golf Club will round off your itinerary nicely.

Recent reviews of Chester hotels
Expedia verified reviews

Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina

5/5 Excellent
"Great! Staff was friendly and courteous, facility was clean and better than expectations. I will stay again for sure!"
A verified traveler stayed at Hyatt Place Kent Narrows & Marina
Posted 2 days ago
Hyatt Place Kent Narrows & Marina