Photo by Patricia Knorr

Chester Holiday Rentals

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Check prices for these dates

In two weeks
12 Dec - 14 Dec
In two months
23 Jan - 25 Jan
In three months
20 Feb - 22 Feb
In four months
20 Mar - 22 Mar

Holiday Rentals in Chester

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Top Chester Hotel Reviews

Graduate by Hilton Annapolis

Graduate by Hilton Annapolis

10/10 Excellent
"Love this hotel and its location. Walkable to downtown, the USNA and the football field. However I think the price per room is excessive especially on football weekends."
Deb 3-night trip
Posted 1 day ago
Graduate by Hilton Annapolis

Frequently asked questions

Can I find holiday rentals in Chester?

Yes, there are holiday rentals close to the most popular sights in Chester, or you can select a more secluded option if you're looking for a relaxing stay. Chester is known for its waterfront and seafood restaurants. Make sure you have time to check out the golf courses while you're in the area.

How many holiday rentals will I find in Chester?

Choose from 11 Expedia holiday rentals in Chester for a memorable holiday.

What’s there to see and do in Chester?

Explore the area and family-friendly sights such as Annapolis Maritime Museum, or get out into nature at a spot like Northern Chesapeake Bay. Matapeake State Park and Love Point State Park are a couple of places you'll find in the wider area.

What’s a holiday rental in Chester like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Chester. Holiday rentals provide amenities such as kitchens and laundry facilities so you'll have all the conveniences of home. If you're concerned about a clean environment, a holiday rental can provide a sense of safety away from shared hotel lifts and busy lobbies while still allowing you the enjoyment of travel. You'll also find more space in a holiday rental than in a traditional hotel, which makes a holiday rental a great option for family trips or small group gatherings.