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Browse Select Chester Condo Rentals

Annapolis Condominium in the heart of the historic center
Terrace/patio

Annapolis Condominium in the heart of the historic center

9.8 out of 10, Exceptional, (282)
"The location and amenities are great. The host are very friendly, helpful and easy to make contact with. My family used this location for commission week and could not have asked for more. "
Annapolis Condominium in the heart of the historic center
Beautiful Condo - Water View Near City Dock
Marina

Beautiful Condo - Water View Near City Dock

9.6 out of 10, Exceptional, (145)
"Clean, quiet, and very close to both downtown and Eastport restaurants."
Beautiful Condo - Water View Near City Dock
Waterfront 2-Bedroom Condo on Spa Creek
Smart TV

Waterfront 2-Bedroom Condo on Spa Creek

10.0 out of 10, Exceptional, (8)
"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
Waterfront Condo with Rooftop Pool, Spa Creek Views & Prime Eastport Location with Parking
Pool

Waterfront Condo with Rooftop Pool, Spa Creek Views & Prime Eastport Location with Parking

10.0 out of 10, Exceptional, (18)
"Can’t have a better location near everything in Eastport and Main St Annapolis!"
Waterfront Condo with Rooftop Pool, Spa Creek Views & Prime Eastport Location with Parking
Kent Island Waterfront Cottage
Fridge, microwave, oven, stovetop

Kent Island Waterfront Cottage

8.8 out of 10, Excellent, (11)
"Enjoyed fishing at the pier and sitting on the porch"
Kent Island Waterfront Cottage
Unbelievable beach views for 6
Property grounds

Unbelievable beach views for 6

2.0 star property
10.0 out of 10, Exceptional, (8)
"It was unbelievable stay with fantastic sunrise and moon rise on the day of the eclipse"
Unbelievable beach views for 6
New Downtown Annapolis Condo With Free Parking
Property grounds

New Downtown Annapolis Condo With Free Parking

10.0 out of 10, Exceptional, (27)
"Clean, modern apartment walking distance from all of Annapolis harbor and restaurants. "
New Downtown Annapolis Condo With Free Parking
Chic Condo w/ Balcony in the Heart of Annapolis!
Interior

Chic Condo w/ Balcony in the Heart of Annapolis!

9.8 out of 10, Exceptional, (58)
"This cute condo is as pictured; charming and clean. Nice bathrooms. Comfortable beds. Great location. Loved the parking ease as well. Host was very receptive and flexible with my arrival/departure times.Would highly recommend and would stay here again."
Chic Condo w/ Balcony in the Heart of Annapolis!
Unique 2-Bedroom Condo in Renovated Parish House
Marina

Unique 2-Bedroom Condo in Renovated Parish House

Unique 2-Bedroom Condo in Renovated Parish House
Upscale Condo in Annapolis
Terrace/patio

Upscale Condo in Annapolis

Upscale Condo in Annapolis
Waterfront condo. Completely renovated. Walk to Kent Island's best places
TV, fireplace

Waterfront condo. Completely renovated. Walk to Kent Island's best places

Waterfront condo. Completely renovated. Walk to Kent Island's best places
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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Top Chester Hotel Reviews

Graduate by Hilton Annapolis

Graduate by Hilton Annapolis

10/10 Excellent
"Every boat show this is my go to spot. "
Ezekiel 1-night trip
Posted 1 day ago
Graduate by Hilton Annapolis