Photo by Patricia Knorr

Chester Vacation Rentals

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Check prices for these dates

Tonight
Feb 16 - Feb 17
Tomorrow
Feb 17 - Feb 18
Next weekend
Feb 21 - Feb 23
In two weeks
Feb 28 - Mar 2

Vacation Rentals in Chester

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Other types of properties in Chester you may be interested in

DoubleTree by Hilton Hotel Annapolis
Lobby

DoubleTree by Hilton Hotel Annapolis

4.0 star property
8.6 out of 10, Excellent, (1005)
"Pretty quiet "
The price is P5,039
P5,745 total
includes taxes & fees
Feb 22 - Feb 23
DoubleTree by Hilton Hotel Annapolis
Graduate by Hilton Annapolis
View from property

Graduate by Hilton Annapolis

4.0 star property
9.4 out of 10, Exceptional, (1009)
"Very walkable. Close to a lot of restaurants and bars. 15-20 walk to the waterfront. "
The price is P8,801
P10,033 total
includes taxes & fees
Mar 16 - Mar 17
Graduate by Hilton Annapolis
Historic Inns of Annapolis
Exterior

Historic Inns of Annapolis

3.5 star property
9.0 out of 10, Wonderful, (1732)
"Beautiful inn."
The price is P8,361
P11,443 total
includes taxes & fees
Feb 25 - Feb 26
Historic Inns of 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.

Frequently asked questions

Can I find vacation rentals in Chester?

Yes, we give you a choice of vacation rentals near well known sights in Chester, or you can go with a secluded option if you'd like a relaxing place to 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 vacation rentals will I find in Chester?

Choose from 8 Expedia vacation rentals in Chester for a memorable vacation.

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 Chesapeake Bay Environmental Center. Love Point State Park and Eastern Neck National Wildlife Refuge are a couple of places you'll find in the larger area.

What’s a vacation rental in Chester like?

Vacation rentals are privately owned properties you can stay in for a couple of days or more in Chester. Vacation rentals offer amenities such as hot tubs, fire pits, and patios so you'll feel just like you're at home. If you're concerned about a sanitized environment, a vacation rental can provide a sense of safety away from shared hotel elevators and lobbies bustling with people while still allowing you to travel. You'll also find more space in a vacation rental than in a traditional hotel, which makes a vacation rental a popular option for a small group gathering.