A coastal town with a marina, a bridge, and a highway.

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Check prices for these dates

In two weeks
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

Our top choices for Chester condo rentals

A living room with a dining table, two sofas, a coffee table, and a patterned rug.

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

Chapel Gate 3BR Steps to City Dock & Naval Academy
Historic District
10.0 out of 10, Exceptional, (1 review)
"Very cute home in great proximity to naval academy"
United States
JENNIFER E.
$432 nightly
The price is $489
Nov 4 - Nov 5
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.

2. 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.
$452 nightly
The price is $515
Nov 2 - Nov 3
Total with taxes and fees
Upscale Condo in Annapolis w/Private Parking
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

The Inn at Chesapeake Bay Beach Club

The Inn at Chesapeake Bay Beach Club

10/10 Excellent
"The staff was awesome. Very professional and helpful. Our room was cleaned and well maintained. The food was great and the spa service was awesome as well."
Lamont 3-night trip
Posted 6 hours ago
The Inn at Chesapeake Bay Beach Club

Find out more about Chester

Chester Condo Rentals information

Number of reviews
5
Accommodation
11 Condo Rentals
Lowest Price
$489
Highest Price
$515

Frequently asked questions

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