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Search Condo Rentals in Chester

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Compare 12 Condo Rentals in Chester with updated reviews, rates, and availability.

Waterfront 2-Bedroom Condo on Spa Creek
Brand new kitchen combines white and color for a fun vibe

Waterfront 2-Bedroom Condo on Spa Creek

10.0 out of 10, Exceptional, (5)
"We had such an amazing time. It had a beautiful view and easy to walk everywhere :)"
Waterfront 2-Bedroom Condo on Spa Creek
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, (265)
"Great location. Clean and very roomy!"
Annapolis Condominium in the heart of the historic center
Eastport Condo in Building with Rooftop Water Views of Spa Creek!
Colorful nautical decor and comfy sofa bed. Unit is not water view.

Eastport Condo in Building with Rooftop 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."
Eastport Condo in Building with Rooftop Water Views of Spa Creek!
Downtown Annapolis Condo w/ Free Parking + Coffee
Living area

Downtown Annapolis Condo w/ Free Parking + Coffee

10.0 out of 10, Exceptional, (16)
"Very nice location and nice apartment!"
Downtown Annapolis Condo w/ Free Parking + Coffee
Walk to Main Street from Waterfront Condo w Pool and Parking
Gather around the living with views of the water at Liberty Lookout.

Walk to Main Street from Waterfront Condo w Pool and Parking

10.0 out of 10, Exceptional, (14)
"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!"
Walk to Main Street from Waterfront Condo w Pool and Parking
Beautiful Condo - Water View Near City Dock
Front gate of building

Beautiful Condo - Water View Near City Dock

9.6 out of 10, Exceptional, (137)
"I’ve stayed at several places around Annapolis and Eastport. This is on the top of my list to return. Great location to walk into DTA and Eastport. Just a five minute walk to the market. 7 minute walk to davis pub! Exactly as advertised, ample parking. Great communication. "
Beautiful Condo - Water View Near City Dock
Chic Condo w/ Balcony in the Heart of Annapolis!
Annapolis Vacation Rental | 2BR | 2BA | 991 Sq Ft | Step-Free Access

Chic Condo w/ Balcony in the Heart of Annapolis!

9.8 out of 10, Exceptional, (49)
"I love the location of the condo. It was in the downtown district of Annapolis. It can be a bit noisy, especially when you’re trying to sleep. If you like quietness while sleeping, this is not the place for you. I’m a city girl so I’m used to the noise. There are lots of coffee shops, bars and restaurants you can go to within walking distance. The condo was clean had everything I needed and the perk was a garage. Yes, I would definitely stay there again.."
Chic Condo w/ Balcony in the Heart of Annapolis!
Kent Island Waterfront Cottage
Miscellaneous

Kent Island Waterfront Cottage

9.2 out of 10, Wonderful, (7)
"We needed to de-stress and this bay-side home gave us all the peace and quiet we needed. It sits on a huge grassy lawn that slopes down to a dock. Geese and osprey kept us company, while motor noise was almost non-existent. It is still close to many amenities and historic towns, but tucked away from the hustle and bustle. There were a few things that needed attention, and Julie, the property manager, responded right away with great courtesy. We loved our stay. "
Kent Island Waterfront Cottage
Water-view condo with rooftop pool & balcony - minutes from downtown

Water-view condo with rooftop pool & balcony - minutes from downtown

9.2 out of 10, Wonderful, (9)
"I recently stayed at the USNA Getaway in Annapolis, MD, and it was fantastic! The location is perfect, right near the Naval Academy and downtown Annapolis. The property is immaculate and beautifully furnished, with a cozy living area, fully equipped kitchen, and a lovely outdoor patio. The bedroom was spacious and super comfortable. The host was incredibly responsive and made sure I had everything I needed. Check-in and check-out were smooth and easy. I highly recommend the USNA Getaway for...
Water-view condo with rooftop pool & balcony - minutes from downtown
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.
Unbelievable beach views for 6
You can't get much closer to the Chesapeake Bay than this 2-bed/1-bath gem that sleeps 6!

Unbelievable beach views for 6

2.0 star property
10.0 out of 10, Exceptional, (3)
"Very nice place in a great location!!!"
Unbelievable beach views for 6
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

Kent Island Time - Enjoy Kent Island Waterfront-Pet Friendly!
Ready to Relax and Enjoy the Water and Sunset Views?

Kent Island Time - Enjoy Kent Island Waterfront-Pet Friendly!

10.0 out of 10, Exceptional, (8)
"Overall it was a wonderful stay for me and 4 of my friends. Plenty of space for everyone to spread out and enjoy the wonderful view of the water while we were between wedding events. The home was off the beaten path, which added to the relaxing feeling of the house. Also it was never more than a 20 min drive to get to our events accross the island. The host was very responsive and more than accommodating for my group. The only very minor suggestion I'd like to make is that the trash in the...
Kent Island Time - Enjoy Kent Island Waterfront-Pet Friendly!
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
Private rear courtyard

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

10.0 out of 10, Exceptional, (202)
"This cozy home was perfect for my coaches & I that were in town for a lacrosse tourney @ the Naval Academy. This home is literally less than 100 steps from the gate of the Naval Base and same distance to dowtown Annapolis city docks, diming, shopping and sight-seeing. We will defintely be back! Thanks John!!"
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
Miscellaneous

Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably

10.0 out of 10, Exceptional, (20)
"Our group had an amazing time staying on this property. There are many areas inside the house as well as outside the house where you can gather with family and friends. It was very quick and easy to order Ubers/lyfts to the downtow Annapolis area whenever we needed. The house is also convientely located near a small shaping center less than a mile away. We would highly recommend this property!"
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
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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