Photo by Patricia Knorr

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Top hotels and accommodation in Chester

Exterior
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, (921)
"The hotel was nice and clean and the staff was always polite and helpful. "
United States
William
The price is NZ$209
includes taxes & fees
15 Dec - 16 Dec
Holiday Inn Express Annapolis East-Kent Island by IHG
Terrace/patio
Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina

3.0 star property
Grasonville
9.4 out of 10, Exceptional, (655)
"My favorite hotel "
United States
Jen
The price is NZ$311
includes taxes & fees
17 Nov - 18 Nov
Hyatt Place Kent Narrows & Marina
View from property
The Westin Annapolis

The Westin Annapolis

4.0 star property
Annapolis
8.6 out of 10, Excellent, (1002)
"Great environment"
United States
Salvador E
The price is NZ$309
includes taxes & fees
14 Dec - 15 Dec
The Westin Annapolis
Terrace/patio
Hilton Garden Inn Kent Island Marina

Hilton Garden Inn Kent Island Marina

3.0 star property
Grasonville
9.0 out of 10, Wonderful, (1000)
"Our view was spectacular and the room was immaculate. Staff was friendly and welcoming. It was close to several restaurants. "
United States
Patricia
The price is NZ$199
includes taxes & fees
23 Nov - 24 Nov
Hilton Garden Inn Kent Island Marina
Aerial view
Kent Island Resort

Kent Island Resort

3.5 star property
Stevensville
9.2 out of 10, Wonderful, (124)
"The property is very charming and the staff was extremely attentive and friendly. It's a beautiful area. Close to Annapolis and a lot of fun things to do."
United States
Michael
The price is NZ$415
includes taxes & fees
1 Dec - 2 Dec
Kent Island Resort
Exterior
Courtyard by Marriott Annapolis

Courtyard by Marriott Annapolis

3.0 star property
Annapolis
8.6 out of 10, Excellent, (1004)
"Wonderful stay. "
United States
Angela
The price is NZ$201
includes taxes & fees
7 Dec - 8 Dec
Courtyard by Marriott Annapolis
1 bedroom, hypo-allergenic bedding, desk, blackout curtains
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, (1005)
"Wonderful country inn!"
United States
Jennifer
The price is NZ$186
includes taxes & fees
7 Dec - 8 Dec
Country Inn & Suites by Radisson, Annapolis, MD
Premium bedding, pillow-top beds, in-room safe, individually furnished
Hampton Inn & Suites Annapolis

Hampton Inn & Suites Annapolis

2.5 star property
Annapolis
8.2 out of 10, Very good, (1004)
"We had a nice stay. "
United States
L Craig
The price is NZ$193
includes taxes & fees
1 Dec - 2 Dec
Hampton Inn & Suites Annapolis
Indoor pool
Crowne Plaza Annapolis by IHG

Crowne Plaza Annapolis by IHG

3.5 star property
Annapolis
8.8 out of 10, Excellent, (1001)
"Nice and quiet, good and clean bed, big parking lot, exellent personel, not complains."
United States
martin
The price is NZ$187
includes taxes & fees
7 Dec - 8 Dec
Crowne Plaza Annapolis by IHG
Terrace/patio
Historic Inns of Annapolis

Historic Inns of Annapolis

3.5 star property
Historic District
9.0 out of 10, Wonderful, (1891)
"The location is excellent. "
United States
Lesa
Historic Inns of Annapolis
Hypo-allergenic bedding, in-room safe, desk, iron/ironing board
Hilton Garden Inn Annapolis

Hilton Garden Inn Annapolis

3.0 star property
Annapolis
8.2 out of 10, Very good, (1001)
"Our stay at the hotel was easy check in and check out. Quiet and great location for our stay."
United States
Patricia
The price is NZ$144
includes taxes & fees
30 Nov - 1 Dec
Hilton Garden Inn Annapolis
Garden
DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis

4.0 star property
Annapolis
8.6 out of 10, Excellent, (1006)
"Room was comfortable and the staff were courtesy!"
United States
Danny
The price is NZ$193
includes taxes & fees
30 Nov - 1 Dec
DoubleTree by Hilton Hotel Annapolis
Room, 2 Queen Beds, Non Smoking, Balcony
Annapolis Waterfront Hotel, Autograph Collection

Annapolis Waterfront Hotel, Autograph Collection

4.0 star property
Historic District
8.8 out of 10, Excellent, (876)
"Clean room. Friendly staff awesome location. "
United States
Brent
The price is NZ$339
includes taxes & fees
14 Dec - 15 Dec
Annapolis Waterfront Hotel, Autograph Collection
Egyptian cotton sheets, premium bedding, pillow-top beds, desk
Sonesta ES Suites Annapolis

Sonesta ES Suites Annapolis

3.0 star property
Edgewater
8.8 out of 10, Excellent, (949)
"Nice breakfast, clean room, great parking"
United States
Amy
The price is NZ$167
includes taxes & fees
7 Dec - 8 Dec
Sonesta ES Suites Annapolis
Front of property – evening/night
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, (426)
"Very nice atmosphere. Fall decor, multiple outdoor fireplaces, water fountains, everything clean, tidy, cozy, and all staff professionally courteous. Just very pleasant all around."
United States
Warren
The price is NZ$404
includes taxes & fees
1 Dec - 2 Dec
The Inn at Chesapeake Bay Beach Club
Suite, 1 Bedroom, Terrace | Living area
Hilton Garden Inn Annapolis Downtown

Hilton Garden Inn Annapolis Downtown

3.0 star property
Annapolis
8.6 out of 10, Excellent, (1001)
"The room was very clean, the staff were very nice. Great location."
United States
Joseph
The price is NZ$159
includes taxes & fees
24 Nov - 25 Nov
Hilton Garden Inn Annapolis Downtown
Free daily self-service breakfast
SpringHill Suites by Marriott Annapolis

SpringHill Suites by Marriott Annapolis

3.0 star property
Annapolis
9.0 out of 10, Wonderful, (1002)
"Clean room, Good breakfast and friendly staff."
United States
Margaret C
The price is NZ$203
includes taxes & fees
24 Nov - 25 Nov
SpringHill Suites by Marriott Annapolis
Free daily buffet breakfast
Holiday Inn Express & Suites Annapolis by IHG

Holiday Inn Express & Suites Annapolis by IHG

2.5 star property
Annapolis
8.2 out of 10, Very good, (1000)
"Staff at front desk were incredibly friendly and helpful!"
United States
Nina
The price is NZ$187
includes taxes & fees
29 Nov - 30 Nov
Holiday Inn Express & Suites Annapolis by IHG
View from property
Graduate by Hilton Annapolis

Graduate by Hilton Annapolis

4.0 star property
Annapolis
9.4 out of 10, Exceptional, (1000)
"Nice big rooms, comfortable beds. Well maintained. "
United States
Margaret
The price is NZ$283
includes taxes & fees
15 Dec - 16 Dec
Graduate by Hilton Annapolis
Outdoor banquet area
The Tilghman Island Inn

The Tilghman Island Inn

3.5 star property
Tilghman
9.6 out of 10, Exceptional, (118)
"Great staff and food!"
United States
Natalie
The price is NZ$387
includes taxes & fees
17 Nov - 18 Nov
The Tilghman Island Inn
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.
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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
Kent Narrows Maryland, USA, the narrows are just north of the Chesapeake bay and about an hour from Washington DC. Here the crabs are abundant and we had a great pick and peel crab dinner and Harrah's Crab house. Boats along this area go out each morning and pick the crabs out of the crab cages and get the catch of the day out in the Chesapeake bay . The Route 50 bridge is directly straight ahead, it the route into the Chesapeake bay bridge which is at least 3 miles long.
Photo by Patricia Knorr
Open Photo by Patricia Knorr

Top Chester Hotel Reviews

Historic Inns of Annapolis

Historic Inns of Annapolis

10/10 Excellent
"Every aspect of my stay was excellent. The staff was exceptional."
Susan 3-night trip
Posted 2 days ago
Historic Inns of Annapolis

More cheap accommodation in Chester

Best Western Annapolis

Best Western Annapolis

2520 Riva Rd, Annapolis, MD
The price is NZ$146 per night from 23 Nov to 24 Nov
NZ$146
23 Nov - 24 Nov
includes taxes & fees
7.6/10 Good! (1,000 reviews)

Frequently asked questions

What's the best place to stay in Chester?
Located 10.8 mi (17.3 km) from the heart of Chester, Historic Inns of Annapolis is a top choice for your stay, based on our traveller data. Two other options for your stay in the area are Country Inn & Suites by Radisson, Annapolis, MD and Sonesta ES Suites Annapolis. See all available top hotels, or vacation rentals in Chester.
What are some of the best holiday rentals that Chester has to offer?
Woodland Retreat on Kent Island: 5 beds, 5 miles from Bay Bridge, on 5 acres.: This holiday home rental outside of Chester is located next to a golf course, and has a patio, a garden and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a fridge, a stovetop and a microwave, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a pool table. 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?
Country Inn & Suites by Radisson, Annapolis, MD: Offers buffet, an indoor pool and free self parking. Sonesta ES Suites Annapolis and Crowne Plaza Annapolis by IHG 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 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 Northern Chesapeake Bay, Matapeake State Park and Love Point State Park. You'll also find Eastern Neck National Wildlife Refuge and Sandy Point Beach 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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