A boat docked at a pier during twilight with a city skyline in the background.

Search and Rent Chester Condos

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Check prices for these dates

In two weeks
Sep 18 - Sep 20
In two months
Oct 30 - Nov 1
In three months
Nov 27 - Nov 29
In four months
Dec 25 - Dec 27

Our top choices for Chester condo rentals

A lobby with a reception desk, a blue sofa, a plant, and a door leading outside.

1. New Downtown Annapolis Condo With Free Parking

New Downtown Annapolis Condo With Free Parking
Historic District
10.0 out of 10, Exceptional, (43 reviews)
"Beautiful property, excellent location, and had a wonderful visit to Annapolis!"
United States
Darby F.
New Downtown Annapolis Condo With Free Parking
A patio with a round table and chairs, a grill, and a wooden fence.

2. Chapel Gate 3BR Steps to City Dock & Naval Academy

Chapel Gate 3BR Steps to City Dock & Naval Academy
Historic District
$461 nightly
The price is $522
Sep 1 - Sep 2
Total with taxes and fees
Chapel Gate 3BR Steps to City Dock & Naval Academy
A modern lobby with a blue sofa, two framed abstract paintings, a potted plant, and a marble floor.

3. Upscale Condo in Annapolis w/Private Parking

Upscale Condo in Annapolis w/Private Parking
Historic District
10.0 out of 10, Exceptional, (4 reviews)
"Great condo! Very clean and convenient to everything in Annapolis. We will definitely be back."
United States
Scott P.
$525 nightly
The price is $599
Sep 8 - Sep 9
Total with taxes and fees
Upscale Condo in Annapolis w/Private Parking
A living room with a fireplace, a television mounted above it displaying an airplane, and a glass coffee table.

4. Luxury Annapolis condo, fully remodeled, rooftop pool & marina, free parking, 0.3 mi to downtown. Perfect for Navy games, Academy visits, or a waterfront getaway.

Luxury Annapolis condo, fully remodeled, rooftop pool & marina, free parking, 0.3 mi to downtown. Perfect for Navy games, Academy visits, or a waterfront getaway.
Eastport
10.0 out of 10, Exceptional, (2 reviews)
"Excellent place to stay!"
United States
Michaell M.
$726 nightly
The price is $797
Sep 1 - Sep 2
Total with taxes and fees
Luxury Annapolis condo, fully remodeled, rooftop pool & marina, free parking, 0.3 mi to downtown. Perfect for Navy games, Academy visits, or a waterfront getaway.
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

DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis

10/10 Excellent
"Nice hotel for decent price!"
Chereis 2-night trip
Posted less than an hour ago
DoubleTree by Hilton Hotel Annapolis

Find out more about Chester

Chester Condo Rentals information

Number of reviews
49
Accommodation
10 Condo Rentals
Lowest Price
$522
Highest Price
$797

Frequently asked questions

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