Chester

Travel Guide

A coastal town with a marina, a bridge, and a highway.
A calm lake with reflections of the sky, surrounded by a forested area.
A boat docked at a pier during twilight with a city skyline in the background.
Historic Inns of Annapolis

Historic Inns of Annapolis

3.5 out of 5
58 State Circle Annapolis MD
The price is €105 per night from 23 Nov to 24 Nov
€105
23 Nov - 24 Nov
includes taxes & fees
Stay at this historic hotel in Annapolis. Enjoy free Wi-Fi, room service and a 24-hour fitness centre. Our guests praise the helpful staff and the clean rooms ...
9/10 Wonderful! (2,072 reviews)
"Positives included being close to the sites and Annapolis history, a very attentive hotel and valet parking staff with quick response to requests. Negatives included a noisy refrigerator, no microwave and a restaurant nearby playing loud music into the late evening. The only real choice was using ..."

Reviewed on 14 Nov 2026

Historic Inns of Annapolis
Crowne Plaza Annapolis by IHG

Crowne Plaza Annapolis by IHG

3.5 out of 5
173 Jennifer Rd Annapolis MD
Fully refundable
The price is €102 per night from 16 Dec to 17 Dec
€102
16 Dec - 17 Dec
includes taxes & fees
Stay at this business-friendly hotel in Annapolis. Enjoy free Wi-Fi, free parking and breakfast (surcharge). Our guests praise the helpful staff and the clean ...
Crowne Plaza Annapolis by IHG
Sonesta ES Suites Annapolis

Sonesta ES Suites Annapolis

3 out of 5
170 Admiral Cochrane Dr Edgewater MD
The price is €83 per night from 24 Nov to 25 Nov
€83
24 Nov - 25 Nov
includes taxes & fees
Stay at this business-friendly hotel in Edgewater. Enjoy free breakfast, free Wi-Fi and an outdoor pool. Our guests praise the helpful staff and the clean rooms ...
8.8/10 Excellent! (1,006 reviews)
"The room was great had everything we needed fridge, stovetop, dishwasher. It was A very nice suite. The staff and property were great"

Reviewed on 14 Nov 2026

Sonesta ES Suites Annapolis
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.
Crab Alley | Bayfront Hot Tub & Game Room

Crab Alley | Bayfront Hot Tub & Game Room

Chester MD
Stay at this holiday home in Chester. Enjoy free Wi-Fi, laundry facilities and a pool table. Popular attractions Bodkin Island and Chesapeake Bay Environmental ...
10/10 Exceptional! (7 reviews)
"Great place with lots of amenities! :)"

Reviewed on 31 Oct 2026

Crab Alley | Bayfront Hot Tub & Game Room
Waterfront Estate Renting 4BR Guest Cottage w/waterviews of Magothy River

Waterfront Estate Renting 4BR Guest Cottage w/waterviews of Magothy River

Arnold MD
Stay at this cottage in Arnold. Enjoy free Wi-Fi, a fitness centre and a garden. Popular attractions Annapolis City Dock and Bay Hills Golf Club are located ...
10/10 Exceptional! (6 reviews)
"Great for 4 of us! Huge kitchen area and comfortable beds!"

Reviewed on 9 Nov 2026

Waterfront Estate Renting 4BR Guest Cottage w/waterviews of Magothy River
Cute, Cozy 2-bedroom house near Annapolis with water access

Cute, Cozy 2-bedroom house near Annapolis with water access

Crownsville MD
Stay at this holiday home in Crownsville. Enjoy free Wi-Fi, a garden and laundry facilities. Popular attractions Joyces Marina and B&A Trail are located ...
9.8/10 Exceptional! (31 reviews)
"Very nice place, clean and updated! We enjoyed our time there"

Reviewed on 1 Nov 2026

Cute, Cozy 2-bedroom house near Annapolis with water access
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.

Stay near popular Chester attractions

Things to do