A coastal town with a marina, a bridge, and a highway.

Chester hotels from HK$660

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Check prices for these dates

Next weekend
13 Nov - 15 Nov
In two weeks
20 Nov - 22 Nov

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Our top choices for Chester hotels

A rooftop terrace with wicker furniture, a fire pit, and a view of a marina.

1. Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina
3.0 star property
Grasonville
9.4 out of 10, Exceptional, (857 reviews)
"Great place to stay"
United States
Michael
The price is HK$1,051
HK$1,167 total
includes taxes & fees
15 Nov - 16 Nov
Hyatt Place Kent Narrows & Marina
A gazebo with a view of a lake at dusk.

2. Holiday Inn Express Annapolis East-Kent Island by IHG

Holiday Inn Express Annapolis East-Kent Island by IHG
2.5 star property
Grasonville
9.2 out of 10, Wonderful, (1,002 reviews)
"A wonderful stay! Already planning a trip for next year!"
United States
Michelle
The price is HK$745
HK$827 total
includes taxes & fees
6 Dec - 7 Dec
Holiday Inn Express Annapolis East-Kent Island by IHG
A balcony with a view of a body of water, a row of buildings, and a chair.

3. Hilton Garden Inn Kent Island Marina

Hilton Garden Inn Kent Island Marina
3.0 star property
Grasonville
8.8 out of 10, Excellent, (1,002 reviews)
"Everything was fantastic"
United States
Gamil
The price is HK$939
HK$1,042 total
includes taxes & fees
18 Nov - 19 Nov
Hilton Garden Inn Kent Island Marina
A hotel entrance with a stone facade, large glass doors, and a sign indicating it is The Inn.

4. The Inn at Chesapeake Bay Beach Club

The Inn at Chesapeake Bay Beach Club
4.0 star property
Stevensville
9.4 out of 10, Exceptional, (512 reviews)
"Great property super friendly, helpful staff."
United States
scott
The price is HK$1,419
HK$1,775 total
includes taxes & fees
9 Dec - 10 Dec
The Inn at Chesapeake Bay Beach Club
A hotel room with a bed, a desk, a chair, and a nightstand.

5. Best Western Kent Narrows Inn

Best Western Kent Narrows Inn
2.5 star property
Grasonville
8.0 out of 10, Very good, (1,002 reviews)
"Nice location & stay"
United States
Holly
The price is HK$705
HK$782 total
includes taxes & fees
15 Nov - 16 Nov
Best Western Kent Narrows Inn
A spacious lobby with a staircase, a reception desk, and a dining area.

6. Quality Inn Grasonville near Kent Island

Quality Inn Grasonville near Kent Island
2.5 star property
Grasonville
7.8 out of 10, Good, (1,001 reviews)
"Clean room, friendly staff, great breakfast attendant"
United States
Crystal
The price is HK$658
HK$730 total
includes taxes & fees
29 Nov - 30 Nov
Quality Inn Grasonville near Kent Island
A large, two-story barn-style building with a covered front porch and a garage.

7. Kent Island Resort

Kent Island Resort
3.5 star property
Stevensville
9.2 out of 10, Wonderful, (190 reviews)
"Just a wonderful place, we had an amazing stay!"
United States
Bethany
The price is HK$959
HK$1,324 total
includes taxes & fees
30 Nov - 1 Dec
Kent Island Resort
A historic brick building with a corner turret and multiple windows, located on a city street with flags and street lamps.

8. Historic Inns of Annapolis

Historic Inns of Annapolis
3.5 star property
Historic District
9.0 out of 10, Wonderful, (2,062 reviews)
"Great location, excellent stay"
United States
Christiaan
The price is HK$559
HK$905 total
includes taxes & fees
17 Nov - 18 Nov
Historic Inns of Annapolis
A balcony with a table set for two, overlooking a marina with boats.

9. Annapolis Waterfront Hotel, Autograph Collection

Annapolis Waterfront Hotel, Autograph Collection
4.0 star property
Historic District
8.8 out of 10, Excellent, (1,000 reviews)
"Staff was Great, Great Location. Nice Restaurant Bartender was great!"
United States
Donna
The price is HK$1,687
HK$1,923 total
includes taxes & fees
23 Nov - 24 Nov
Annapolis Waterfront Hotel, Autograph Collection
A modern kitchen with grey cabinets, a white countertop, and various kitchen appliances.

10. SpringHill Suites by Marriott Annapolis

SpringHill Suites by Marriott Annapolis
3.0 star property
Annapolis
9.0 out of 10, Wonderful, (1,000 reviews)
"The hotel is close to lots of shopping and dining options."
United States
FRANK
The price is HK$793
HK$904 total
includes taxes & fees
29 Nov - 30 Nov
SpringHill Suites by Marriott Annapolis
A spacious lobby with a high ceiling, a reception desk, seating areas, and a central decorative piece.

11. The Westin Annapolis

The Westin Annapolis
4.0 star property
Annapolis
8.8 out of 10, Excellent, (1,002 reviews)
"This is a fabulous resort! Very clean, great location and the staff is great!"
United States
Bobbi
The price is HK$1,325
HK$1,510 total
includes taxes & fees
15 Nov - 16 Nov
The Westin Annapolis
A modern lounge area with a blue sofa, red chairs, and plaid armchairs. A coffee table with books and a vase of flowers is in the center. Large windows offer a view of a brick building with awnings.

12. Graduate by Hilton Annapolis

Graduate by Hilton Annapolis
4.0 star property
Annapolis
9.4 out of 10, Exceptional, (1,010 reviews)
"Brunch was the best we had the whole trip! Excellent food and wonderful staff."
United States
REBECCA
The price is HK$1,022
HK$1,165 total
includes taxes & fees
29 Nov - 30 Nov
Graduate by Hilton Annapolis
A hotel lobby with a reception desk, a large aquarium, and framed artwork on the walls.

13. DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis
4.0 star property
Annapolis
8.8 out of 10, Excellent, (1,273 reviews)
"Excellent staff & service!"
United States
Michele
The price is HK$701
HK$799 total
includes taxes & fees
10 Nov - 11 Nov
DoubleTree by Hilton Hotel Annapolis
A hotel with a covered entrance, large columns, and a brick facade.

14. Holiday Inn Express & Suites Annapolis by IHG

Holiday Inn Express & Suites Annapolis by IHG
2.5 star property
Annapolis
8.4 out of 10, Very good, (1,003 reviews)
"Great breakfast and hot tub"
United States
Marc
The price is HK$745
HK$849 total
includes taxes & fees
22 Nov - 23 Nov
Holiday Inn Express & Suites Annapolis by IHG
A swimming pool with a clear blue water, surrounded by lounge chairs and a glass wall.

15. Crowne Plaza Annapolis by IHG

Crowne Plaza Annapolis by IHG
3.5 star property
Annapolis
8.8 out of 10, Excellent, (1,010 reviews)
"Great location"
United States
Jose
The price is HK$808
HK$921 total
includes taxes & fees
6 Dec - 7 Dec
Crowne Plaza Annapolis by IHG
Lobby

16. Hilton Garden Inn Annapolis Downtown

Hilton Garden Inn Annapolis Downtown
3.0 star property
Annapolis
8.6 out of 10, Excellent, (1,007 reviews)
"Great location, friendly staff."
United States
Joel
The price is HK$765
HK$872 total
includes taxes & fees
22 Nov - 23 Nov
Hilton Garden Inn Annapolis Downtown
An outdoor patio with tables, chairs, and a fire feature.

17. Fairfield Inn & Suites By Marriott Annapolis

Fairfield Inn & Suites By Marriott Annapolis
3.0 star property
Annapolis
8.8 out of 10, Excellent, (250 reviews)
"Nice hotel"
United States
Imola
The price is HK$996
HK$1,135 total
includes taxes & fees
15 Nov - 16 Nov
Fairfield Inn & Suites By Marriott Annapolis
A room with a fireplace, a dining area with chairs, a large window with a view of the outside, and a cabinet with bottles.

18. Inn at Perry Cabin

Inn at Perry Cabin
5.0 star property
Downtown St. Michaels
9.6 out of 10, Exceptional, (407 reviews)
"Fantastic place; one of those that you don’t want to leave the property until the very sad time to go. Lovely staff, all of them, amazing food."
United States
Virgilio
The price is HK$3,414
HK$3,755 total
includes taxes & fees
9 Dec - 10 Dec
Inn at Perry Cabin
An outdoor patio with tables, chairs, and a fire feature.

19. Residence Inn By Marriott Annapolis

Residence Inn By Marriott Annapolis
3.0 star property
Annapolis
9.0 out of 10, Wonderful, (95 reviews)
"Amazing stay!"
United States
Caitlin
The price is HK$1,058
HK$1,207 total
includes taxes & fees
23 Nov - 24 Nov
Residence Inn By Marriott Annapolis
A spacious living room with a large wooden coffee table, a leather sofa, and a chandelier.

20. Country Inn & Suites by Radisson, Annapolis, MD

Country Inn & Suites by Radisson, Annapolis, MD
3.0 star property
Annapolis
9.0 out of 10, Wonderful, (1,060 reviews)
"I have stayed here before. Very nice hotel cause it is in a great location."
United States
Michael
The price is HK$684
HK$779 total
includes taxes & fees
29 Nov - 30 Nov
Country Inn & Suites by Radisson, Annapolis, MD
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.
View all properties

Compare top hotels in Chester

A rooftop terrace with wicker furniture, a fire pit, and a view of a marina.

Hyatt Place Kent Narrows & Marina

3.0 star property
Grasonville
View
A gazebo with a view of a lake at dusk.

Holiday Inn Express Annapolis East-Kent Island by IHG

2.5 star property
Grasonville
View
A balcony with a view of a body of water, a row of buildings, and a chair.

Hilton Garden Inn Kent Island Marina

3.0 star property
Grasonville
View
A hotel entrance with a stone facade, large glass doors, and a sign indicating it is The Inn.

The Inn at Chesapeake Bay Beach Club

4.0 star property
Stevensville
View
A hotel room with a bed, a desk, a chair, and a nightstand.

Best Western Kent Narrows Inn

2.5 star property
Grasonville
View
9.4
Exceptional
857 reviews
9.2
Wonderful
1,002 reviews
8.8
Excellent
1,002 reviews
9.4
Exceptional
512 reviews
8.0
Very good
1,002 reviews
The price is HK$1,051
HK$1,167 total
includes taxes & fees
15 Nov - 16 Nov
The price is HK$745
HK$827 total
includes taxes & fees
6 Dec - 7 Dec
The price is HK$939
HK$1,042 total
includes taxes & fees
18 Nov - 19 Nov
The price is HK$1,419
HK$1,775 total
includes taxes & fees
9 Dec - 10 Dec
The price is HK$705
HK$782 total
includes taxes & fees
15 Nov - 16 Nov
  • Yes, Breakfast included
  • Yes, Pool
  • No Spa
  • Yes, Pet-friendly
  • Yes, WiFi included
  • Yes, Parking
  • Yes, Breakfast included
  • Yes, Pool
  • No Spa
  • Yes, Pet-friendly
  • Yes, WiFi included
  • Yes, Parking
  • No Breakfast included
  • Yes, Pool
  • No Spa
  • Yes, Pet-friendly
  • No WiFi included
  • Yes, Parking
  • No Breakfast included
  • Yes, Pool
  • Yes, Spa
  • No Pet-friendly
  • Yes, WiFi included
  • Yes, Parking
  • Yes, Breakfast included
  • Yes, Pool
  • No Spa
  • Yes, Pet-friendly
  • Yes, WiFi included
  • Yes, Parking
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Stay near popular Chester attractions

Chesapeake Exploration Center

Learn about the events happening in Chesapeake Exploration Center during your trip to Kent Narrows. Stroll along the area's marina or simply enjoy its seafood restaurants.
See properties

Learn more about Chester

Chester awaits: its island views, sunny weather, golf and more!

See all hotels in Chester
A coastal town with a marina, a bridge, and a highway.

Top Chester Hotel Reviews

Historic Inns of Annapolis

Historic Inns of Annapolis

10/10 Excellent
"Beautiful inns. Well maintained. Walking distance to the heart of Annapolis."
Eleni 3-night trip
Posted 8 hours ago
Historic Inns of Annapolis

More cheap stays in Chester

St Michaels Inn

St Michaels Inn

1228 S Talbot Street St. Michaels MD
The price is HK$600 per night from 1 Dec to 2 Dec
HK$600
HK$660 total
1 Dec - 2 Dec
includes taxes & fees

Hotels in Chester with star-rating

Frequently asked questions

What's the best place to stay in Chester?
Located 13.8 mi (22.2 km) from the heart of Chester, DoubleTree by Hilton Hotel Annapolis is a top choice for your stay, based on our traveller data. Two other options for your stay in the area are Historic Inns of Annapolis and Crowne Plaza Annapolis by IHG. See all available top hotels, or vacation rentals in Chester.
What are some of the best holiday rentals that Chester has to offer?
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach: This holiday home rental outside of Chester is located near the beach, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday. See all vacation rentals in Chester.
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 are some accommodation options with pools in Chester?
Crowne Plaza Annapolis by IHG: Hotel located near U.S. Naval Academy. Provides free self parking, an indoor pool and complimentary wireless Internet access. St Michaels Inn and Sonesta ES Suites Annapolis are a couple of other choices that offer an on-site pool. View all hotels with pools 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 9 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 Northern Chesapeake Bay, Matapeake State Park and Eastern Neck National Wildlife Refuge. You'll also find Sandy Point Beach and Queenstown Harbor Golf 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.

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