Photo by Patricia Knorr

Chester Hotels

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Nov 22 - Nov 23
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Top 10 trending Chester hotels

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, (924)
"nice, clean, up to date, budget friendly hotel"
United States
mike
The price is P5,602
P6,218 total
includes taxes & fees
Dec 14 - Dec 15
Holiday Inn Express Annapolis East-Kent Island by IHG
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, (1001)
"Easy parking and check in. Conveniently located within walking distance of some great seafood restaurants. Always an enjoyable stay"
United States
Roberta
The price is P7,014
P7,786 total
includes taxes & fees
Dec 21 - Dec 22
Hilton Garden Inn Kent Island Marina
Terrace/patio
Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina

3.0 star property
Grasonville
9.4 out of 10, Exceptional, (658)
"My favorite hotel "
United States
Jen
The price is P8,315
P9,229 total
includes taxes & fees
Nov 24 - Nov 25
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, (1001)
"Great environment"
United States
Salvador E
The price is P9,062
P10,331 total
includes taxes & fees
Dec 15 - Dec 16
The Westin Annapolis
1 bedroom, hypo-allergenic bedding, desk, blackout drapes
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, (1003)
"Wonderful country inn!"
United States
Jennifer
The price is P5,202
P5,930 total
includes taxes & fees
Dec 21 - Dec 22
Country Inn & Suites by Radisson, Annapolis, MD
Exterior
Courtyard by Marriott Annapolis

Courtyard by Marriott Annapolis

3.0 star property
Annapolis
8.6 out of 10, Excellent, (1002)
"Wonderful stay. "
United States
Angela
The price is P5,708
P6,507 total
includes taxes & fees
Dec 7 - Dec 8
Courtyard by Marriott Annapolis
Aerial view
Kent Island Resort

Kent Island Resort

3.5 star property
Stevensville
9.2 out of 10, Wonderful, (125)
"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 P7,373
P10,244 total
includes taxes & fees
Dec 17 - Dec 18
Kent Island Resort
Premium bedding, pillowtop 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, (1006)
"I had a great experience at my stay at Hampton "
United States
Idris O
The price is P5,649
P6,440 total
includes taxes & fees
Dec 15 - Dec 16
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, (1008)
"Clean, easy parking, nice staff but over priced breakfast"
United States
Gabrielle
The price is P5,837
P6,655 total
includes taxes & fees
Dec 21 - Dec 22
Crowne Plaza Annapolis by IHG
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)
"I had a lovely stay."
United States
Kalynn
The price is P3,954
P4,508 total
includes taxes & fees
Dec 21 - Dec 22
Hilton Garden Inn Annapolis
Terrace/patio
Historic Inns of Annapolis

Historic Inns of Annapolis

3.5 star property
Historic District
9.0 out of 10, Wonderful, (1901)
"Front desk staff was very helpful, and the location was perfect for exploring downtown Annapolis!"
United States
Christine
The price is P6,550
P9,479 total
includes taxes & fees
Nov 30 - Dec 1
Historic Inns of Annapolis
Premium bedding, down comforters, pillowtop beds, in-room safe
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 P8,609
P9,814 total
includes taxes & fees
Dec 18 - Dec 19
Annapolis Waterfront Hotel, Autograph Collection
Living area
Hilton Garden Inn Annapolis Downtown

Hilton Garden Inn Annapolis Downtown

3.0 star property
Annapolis
8.6 out of 10, Excellent, (1007)
"Clean room, great staff, great breakfast "
United States
Susanne
The price is P4,284
P4,884 total
includes taxes & fees
Dec 7 - Dec 8
Hilton Garden Inn Annapolis Downtown
Garden
DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis

4.0 star property
Annapolis
8.6 out of 10, Excellent, (1013)
"Room was comfortable and the staff were courtesy!"
United States
Danny
The price is P3,634
P4,143 total
includes taxes & fees
Dec 21 - Dec 22
DoubleTree by Hilton Hotel 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, (427)
"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 P10,818
P13,505 total
includes taxes & fees
Dec 21 - Dec 22
The Inn at Chesapeake Bay Beach Club
Egyptian cotton sheets, premium bedding, pillowtop beds, desk
Sonesta ES Suites Annapolis

Sonesta ES Suites Annapolis

3.0 star property
Edgewater
8.8 out of 10, Excellent, (952)
"Nice breakfast, clean room, great parking"
United States
Amy
The price is P4,884
P5,568 total
includes taxes & fees
Dec 21 - Dec 22
Sonesta ES Suites Annapolis
Free daily self-serve breakfast
SpringHill Suites by Marriott Annapolis

SpringHill Suites by Marriott Annapolis

3.0 star property
Annapolis
9.0 out of 10, Wonderful, (1000)
"Friendly staff and comfortable rooms. We love staying here when we visit the area as a family."
United States
Jennifer
The price is P5,452
P6,215 total
includes taxes & fees
Nov 30 - Dec 1
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, (1001)
"Staff at front desk were incredibly friendly and helpful!"
United States
Nina
The price is P4,425
P5,045 total
includes taxes & fees
Dec 20 - Dec 21
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, (1002)
"Nice big rooms, comfortable beds. Well maintained. "
United States
Margaret
The price is P7,962
P9,076 total
includes taxes & fees
Dec 21 - Dec 22
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 room and water view! Staff is very friendly and welcoming. "
United States
Nicole
The price is P11,769
P12,946 total
includes taxes & fees
Nov 25 - Nov 26
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 at 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
"Good location"
RANDOLPH 2-night trip
Posted 2 days ago
Historic Inns of Annapolis

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 traveler data. Other good choices for your visit to the area are DoubleTree by Hilton Hotel Annapolis and Graduate by Hilton Annapolis. See all available top hotels, or 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 room reservations are fully refundable if you cancel before the accommodation's cancellation deadline, which is usually within 24-48 hours of your check-in date. If your reservation is non-refundable, you might be able to still cancel and receive a refund within a 24-hour period of booking. Filter your search by fully refundable to find flexible hotel deals in Chester.
What are some accommodations with pools in Chester?
Sonesta ES Suites Annapolis: Offers buffet, a seasonal outdoor pool, and complimentary wireless internet access. Country Inn & Suites by Radisson, Annapolis, MD and Crowne Plaza Annapolis by IHG are a couple of other choices with an onsite 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 accommodations 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 Club in the area. Check out what more 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 temp of 74°F, while the coldest months are January and February with an average of 39°F. Average annual precipitation for Chester is 56 inches.

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