Chester Holiday Packages
Save when you book Chester package deals
Book your Chester holiday
Wotif is here to help you save your hard-earned cash.
Roll your flights and hotels into one easy package deal.
With your extra funds, you won't run out of things to do in Chester.
You could gain savings of up to . Also, with more than 550 airlines and 665,000 worldwide properties, it's easy to craft your perfect holiday.
With Wotif's competitive prices, you'll be zipping up your suitcase and hitting the skies before you know it.
Chester Accommodation
You're out of luck if you were hoping to secure accommodations in Chester. However, there are 6 properties just a quick car trip away. Have a squiz at your choices on Wotif.
Can't decide on where to get your shut-eye? Then let us help. The Waterfront Historic Kent Manor Inn (500 Kent Manor Dr) and The Inn at Chesapeake Bay Beach Club (180 Pier One Road) are some decent places not too far away.
Car Hire in Chester
Collecting a vehicle directly from Baltimore Washington International Thurgood Marshall Airport means that you don't need to bother with public buses or taxis. Hertz is just a quick walk from the luggage carousel.Eager to hire a car in the centre of town? Enterprise (1418 Main St) is the closest rental company available. It's only 3 kilometres away.
Holidays to Chester
Counting down the days until you can kick back and chill out in Chester? We hear ya. Get there faster, or at least a bit more clued in, by reading up on this thrilling destination.Chester is a neighbourhood in the Maryland state capital of Annapolis. You can find it 19 kilometres east of the centre of the city.
Want to learn how many people reside in Annapolis? At last count, it was around 38 000.
Top Chester hotels
Waterfront Sunset Bayview: sleeps 6
"Very nice host and beautiful modern house! Close to town and had a dock right there to sit out on and enjoy a cup or coffee! Only complaint was one shower never got hot or warm but we just used one and it was fine"
Reviewed on 22 May 2026
Historic Inns of Annapolis
"First room had non-functional ac in 90+ heat. Went to dinner while it was worked on. Was notified during dinner that it couldn't be repaired and to expect a new room upon return. Eventually got a room but had to wait 10 minutes in heat although they knew we were coming back. The staff member was ..."
Reviewed on 12 June 2026
Crowne Plaza Annapolis by IHG
"The hot tub was out of service. The restaurant was never open when we wanted to dine there. The bathroom in the room had an odor. Otherwise the stay was suitable for the couple of nights my husband and I stayed."
Reviewed on 9 June 2026
