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May 14 - May 15
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May 15 - May 16
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May 17 - May 19
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May 24 - May 26

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Top hotels and accommodation in Chester

Outdoor pool, a heated pool
Waterfront Oasis of Annapolis Star
10.0 out of 10, Exceptional, (59)
"Stayed here during wedding night. Host accommodated requests to make the night check in go smoothly. Property is amazing, the Star was everything we thought and more. Would absolutely stay again!"
The price is NZ$780
includes taxes & fees
28 May - 29 May
Waterfront Oasis of Annapolis Star
Smart TV
Cass-Away Luxury Houseboat
10.0 out of 10, Exceptional, (80)
"Very much enjoyed the houseboat. Perfect location - within walking distance of all local attractions / restaurants. Sunset view on the deck is amazing! Hope to come back soon!"
The price is NZ$703
includes taxes & fees
19 May - 20 May
Cass-Away Luxury Houseboat
Beach nearby
Inn at Horn Point
3.0 star property
9.6 out of 10, Exceptional, (18)
"I booked the trip to celebrate an anniversary weekend away with my husband. The property came up through a Yelp review so I checked it out. I was impressed with the location, the detail to cleanliness, and the commitment to the environment. Once I booked the room, the innkeepers were very helpful in offering things to do and places to eat, as well as offering to help make our anniversary stay more memorable. Once we arrived, Cory took the time to greet us as we came in and share some of the...
The price is NZ$613
includes taxes & fees
15 May - 16 May
Inn at Horn Point
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View from property
Graduate Annapolis
4.0 star property
9.4 out of 10, Exceptional, (1056)
"Quiet, clean, lovely!"
The price is NZ$325
includes taxes & fees
27 May - 28 May
Graduate Annapolis
Desk, iron/ironing board, free cots/infant beds, free WiFi
Courtyard by Marriott Bowie
3.0 star property
9.4 out of 10, Exceptional, (640)
"It was hassle free and the customer service was amazing 👏 "
The price is NZ$327
includes taxes & fees
26 May - 27 May
Courtyard by Marriott Bowie
Front of property
Anchored Inn at Hidden Harbour Marina
2.5 star property
9.4 out of 10, Exceptional, (363)
"Would stay here again "
The price is NZ$472
includes taxes & fees
15 May - 16 May
Anchored Inn at Hidden Harbour Marina
Front of property - evening/night
The Inn at Chesapeake Bay Beach Club
4.0 star property
9.4 out of 10, Exceptional, (341)
"Beautiful property very kind staff and wonderful amenities..would highly recommend"
The price is NZ$483
includes taxes & fees
15 May - 16 May
The Inn at Chesapeake Bay Beach Club
25-inch TV with cable channels
TownePlace Suites Bowie Town Center
2.5 star property
9.2 out of 10, Wonderful, (458)
"The best"
The price is NZ$205
includes taxes & fees
9 Jun - 10 Jun
TownePlace Suites Bowie Town Center
Indoor pool
Country Inn & Suites by Radisson, Annapolis, MD
3.0 star property
9.0 out of 10, Wonderful, (1000)
"Nice clean, large rooms. Thank you for an excellent stay. I would say the traffic around Annapolis is terrible as the only negative."
The price is NZ$205
includes taxes & fees
9 Jun - 10 Jun
Country Inn & Suites by Radisson, Annapolis, MD
Bar (on property)
Comfort Inn Conference Center
2.5 star property
9.0 out of 10, Wonderful, (1000)
"Staff"
The price is NZ$186
includes taxes & fees
9 Jun - 10 Jun
Comfort Inn Conference Center
Beach
Indulge or be still near Naval Academy/ Annapolis
9.0 out of 10, Wonderful, (8)
"Karen was absolutely wonderful! I had several questions and she responded within just a few moments. The place was immaculate, cozy it felt like it was a home away from home. Very close to anything you could possibly need and the view is absolutely breathtaking. The bed was so comfortable that I found out the type of mattress and I’ll be buying one. I highly recommend staying with Karen. I will certainly be booking again in the future. 5 Stars across the board!"
Indulge or be still near Naval Academy/ Annapolis
Pool
Crowne Plaza Annapolis, an IHG Hotel
3.5 star property
8.8 out of 10, Excellent, (1002)
"Parking limited on weekend evenings "
The price is NZ$273
includes taxes & fees
19 May - 20 May
Crowne Plaza Annapolis, an IHG Hotel
Exterior
Microtel Inn & Suites by Wyndham Gambrills
2.0 star property
8.8 out of 10, Excellent, (723)
"Great location, clean, "
The price is NZ$175
includes taxes & fees
16 May - 17 May
Microtel Inn & Suites by Wyndham Gambrills
Room, 2 Queen Beds, Balcony
Annapolis Waterfront Hotel, Autograph Collection
4.0 star property
8.8 out of 10, Excellent, (710)
"I like everything about this property!"
The price is NZ$468
includes taxes & fees
27 May - 28 May
Annapolis Waterfront Hotel, Autograph Collection
Property amenity
Staybridge Suites Washington DC East - Largo, an IHG Hotel
3.0 star property
8.8 out of 10, Excellent, (417)
"No need to look any further! This place is everything you need or want. Friendly staff, so clean, close to Washington DC. "
The price is NZ$284
includes taxes & fees
19 May - 20 May
Staybridge Suites Washington DC East - Largo, an IHG Hotel
Egyptian cotton sheets, premium bedding, pillow-top beds, desk
Sonesta ES Suites Annapolis
3.0 star property
8.8 out of 10, Excellent, (616)
"We had a great stay bad weather and all. The room was very comfortable and inviting. Enjoyed good eats from the local restaurant and had some drinks at the bar."
The price is NZ$232
includes taxes & fees
28 May - 29 May
Sonesta ES Suites Annapolis
Lobby
DoubleTree by Hilton Hotel Annapolis
4.0 star property
8.6 out of 10, Excellent, (1008)
"Beautiful and convenient suite. Very helpful staff. Thank you!"
The price is NZ$216
includes taxes & fees
26 May - 27 May
DoubleTree by Hilton Hotel Annapolis
Exterior
Courtyard by Marriott Annapolis
3.0 star property
8.6 out of 10, Excellent, (856)
"Marriott rarely disappoints. Good, well maintained, comfortable hotel with a nice courtyard with a fireplace, seating areas, etc. Large enough room, comfortable, clean."
The price is NZ$263
includes taxes & fees
26 May - 27 May
Courtyard by Marriott Annapolis
Suite, 1 Bedroom, Terrace | Living area
Hilton Garden Inn Annapolis Downtown
3.0 star property
8.6 out of 10, Excellent, (846)
"Very close to shopping, dining, and night life. Parking was tight and we actually had to pay $25"
The price is NZ$263
includes taxes & fees
27 May - 28 May
Hilton Garden Inn Annapolis Downtown
Exterior
Lower Level Loft - Adorable Studio Apt. Near BWI
8.6 out of 10, Excellent, (4)
"Very nice for a short stay"
The price is NZ$208
includes taxes & fees
18 May - 19 May
Lower Level Loft - Adorable Studio Apt. Near BWI
Don't see what you're looking for?
See all available properties in Chester
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

If I need to cancel my hotel reservation in Chester, will I receive a refund?

Yes! You'll find that most hotel bookings are refundable if you cancel before the accommodation's cancellation deadline, which is usually within 24-48 hours of check in. If you booked a non-refundable reservation, it may still be possible to cancel it and receive a refund within 24 hours of booking. Filter your search by fully refundable to find flexible hotel deals in Chester.

What is staying in Chester like?

Visitors can enjoy all that Chester has to offer, including the waterfront, seafood restaurants and golf courses. In Chester, there are 12 hotels and other accommodation options to choose from. Find out more about Chester.

What is there to see in Chester?

Places to visit in the wider area include Matapeake State Park, Chesapeake Bay Environmental Center and Sandy Point Beach. You'll also find Queenstown Harbor Golf Club and Chesapeake Bay Bridge in the area. Take a look at what more there is to see and do in Expedia's Chester guide.

What's the weather like in Chester?

The hottest months are usually July and August, with an average temperature of 23°C, while the coldest months are January and February, with an average of 4°C. Average annual precipitation for Chester is 1414 mm.