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1 Apr - 2 Apr
Tomorrow
2 Apr - 3 Apr
This weekend
3 Apr - 5 Apr
Next weekend
10 Apr - 12 Apr

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Our top choices for Chester hotels

Indoor pool

Best Western Kent Narrows Inn

Best Western Kent Narrows Inn
2.5 star property
Grasonville
8.0 out of 10, Very good, (1,000 reviews)
"Wonderful staff,Clean rooms and comfortable bed!!"
United States
Evette
The price is NZ$195
includes taxes & fees
7 Apr - 8 Apr
Best Western Kent Narrows Inn
Reception

Kent Island Resort

Kent Island Resort
3.5 star property
Stevensville
9.2 out of 10, Wonderful, (134 reviews)
"Beautiful hotel, nice staff"
United States
Kim
The price is NZ$284
includes taxes & fees
2 Apr - 3 Apr
Kent Island Resort
Suite, 1 Queen Bed, Non Smoking

Quality Inn Grasonville near Kent Island

Quality Inn Grasonville near Kent Island
2.5 star property
Grasonville
7.8 out of 10, Good, (886 reviews)
"Staff was nice and room was clean "
United States
Lauren
The price is NZ$189
includes taxes & fees
15 Apr - 16 Apr
Quality Inn Grasonville near Kent Island
Lobby

Best Western Plus Easton Inn & Suites

Best Western Plus Easton Inn & Suites
2.5 star property
Easton
9.2 out of 10, Wonderful, (1,006 reviews)
"Fresh breakfast with a good variety, friendly staff that gave me an upgrade, clean cozy hotel, safe well-lighted parking area"
United States
Irene
The price is NZ$209
includes taxes & fees
2 Apr - 3 Apr
Best Western Plus Easton Inn & Suites
Exterior

Quality Inn

Quality Inn
2.5 star property
Easton
7.6 out of 10, Good, (854 reviews)
"Room was clean and staff was friendly and helpful."
United States
Constantine
The price is NZ$163
includes taxes & fees
7 Apr - 8 Apr
Quality Inn
Exterior

Wylder Tilghman Island

Wylder Tilghman Island
2.0 star property
Tilghman
8.8 out of 10, Excellent, (93 reviews)
"We were"
United States
Guevara
The price is NZ$287
includes taxes & fees
7 Apr - 8 Apr
Wylder Tilghman Island
Exterior

Haven Point Inn and Gallery

Haven Point Inn and Gallery
2.0 star property
Rock Hall
The price is NZ$287
includes taxes & fees
22 Apr - 23 Apr
Haven Point Inn and Gallery
Front of property

Anchored Inn at Hidden Harbour Marina

Anchored Inn at Hidden Harbour Marina
2.5 star property
Deale
9.4 out of 10, Exceptional, (478 reviews)
"The Anchored Inn at Hidden Harbour Marina is a small gem of a hotel in Deale, Maryland. The staff was incredibly kind and professional. We were there "off season" and enjoyed the quiet. The room was a little small, but the bed was very comfortable. We would stay at the Anchored Inn again in a heartbeat!"
United States
Katey
The price is NZ$302
includes taxes & fees
2 Apr - 3 Apr
Anchored Inn at Hidden Harbour Marina
Exterior

George Brooks House B&B

George Brooks House B&B
3.0 star property
St. Michaels
8.8 out of 10, Excellent, (70 reviews)
"A beautiful renovated historical house with charm, clean rooms, decorative furnishings and a wonderful hot breakfast. What we enjoyed the most was the warm hospitality of Willard, Valerie, and the other staff. Very close to downtown St. Michael’s, but just far enough away to give a nice feel of natural serenity. Great for a quick getaway from the city. We will be back. "
United States
Charles
The price is NZ$325
includes taxes & fees
2 Apr - 3 Apr
George Brooks House B&B
Exterior

Knapps Narrows Marina & Inn

Knapps Narrows Marina & Inn
3.0 star property
Sherwood
9.4 out of 10, Exceptional, (376 reviews)
"Such a marvelous retreat! And the balcony facing the boats and the Bay at sunset is so welcome after exploring St Michael’s (a short 17 mins drive). Extremely friendly staff and good breakfast. Highly recommend to any nature lovers."
United States
Nadia
The price is NZ$287
includes taxes & fees
7 Apr - 8 Apr
Knapps Narrows Marina & Inn
Meeting facility

The Tidewater Inn

The Tidewater Inn
3.0 star property
Easton
8.8 out of 10, Excellent, (863 reviews)
"The property was beautiful and we enjoyed the room, the bar and the restaurant for breakfast. It is also in a great location in a very walkable town area."
United States
Linda
The price is NZ$324
includes taxes & fees
6 Apr - 7 Apr
The Tidewater Inn
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, (977 reviews)
"Very nice hotel, good breakfast selection, clean rooms."
United States
Linda
The price is NZ$213
includes taxes & fees
12 Apr - 13 Apr
Holiday Inn Express Annapolis East-Kent Island by IHG
Front of property

St Michaels Inn

St Michaels Inn
2.5 star property
St. Michaels
8.2 out of 10, Very good, (1,000 reviews)
" Great place,great location, was in town for St Michael Chocolate fest "
United States
Katherine
The price is NZ$233
includes taxes & fees
5 Apr - 6 Apr
St Michaels Inn
Lake

Inn at Huntingfield Creek

Inn at Huntingfield Creek
3.5 star property
Rock Hall
10.0 out of 10, Exceptional, (62 reviews)
"The owners and staff were very courteous and nice. The room layout was great and thoughtfully designed and decorated."
United States
Sandra
The price is NZ$271
includes taxes & fees
5 Apr - 6 Apr
Inn at Huntingfield Creek
Front of property

The Wildset

The Wildset
2.5 star property
Downtown St. Michaels
9.8 out of 10, Exceptional, (429 reviews)
"Best HOTEL EVER!!!"
United States
Ama
The price is NZ$458
includes taxes & fees
7 Apr - 8 Apr
The Wildset
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, (1,000 reviews)
"Beautiful area"
United States
Dan
The price is NZ$268
includes taxes & fees
9 Apr - 10 Apr
Hilton Garden Inn Kent Island Marina
Porch

Parsonage Inn

Parsonage Inn
3.5 star property
Downtown St. Michaels
9.2 out of 10, Wonderful, (131 reviews)
"Hosts were wonderful, breakfast was delicious, everything was walkable "
United States
Nathaly
The price is NZ$285
includes taxes & fees
2 Apr - 3 Apr
Parsonage Inn
Lobby

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, (1,001 reviews)
"I had a great stay & everything was great"
United States
Timothy L
The price is NZ$197
includes taxes & fees
26 Apr - 27 Apr
Country Inn & Suites by Radisson, Annapolis, MD
Lobby

Candlewood Suites Annapolis by IHG

Candlewood Suites Annapolis by IHG
2.5 star property
Annapolis
8.8 out of 10, Excellent, (223 reviews)
"Hotel was clean staff was friendly"
United States
Kim
The price is NZ$175
includes taxes & fees
4 Apr - 5 Apr
Candlewood Suites Annapolis by IHG
Reception

DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis
4.0 star property
Annapolis
8.6 out of 10, Excellent, (1,010 reviews)
"Wonderful and clean accommodations "
United States
Emily
The price is NZ$200
includes taxes & fees
5 Apr - 6 Apr
DoubleTree by Hilton Hotel 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.
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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
Photo by Patricia Knorr
Open Photo by Patricia Knorr

Top Chester Hotel Reviews

Hilton Garden Inn Annapolis Downtown

Hilton Garden Inn Annapolis Downtown

10/10 Excellent
"Great location "
Brent 2-night trip
Posted 5 hours ago
Hilton Garden Inn Annapolis Downtown

More cheap accommodation in Chester

Candlewood Suites Annapolis by IHG

Candlewood Suites Annapolis by IHG

1 Womack Dr Annapolis MD
The price is NZ$175 per night from 4 Apr to 5 Apr
NZ$175
4 Apr - 5 Apr
includes taxes & fees
8.8/10 Excellent! (223 reviews)

Frequently asked questions

What's the best place to stay in Chester?
Located 11.2 mi (18 km) from the heart of Chester, Graduate by Hilton Annapolis is a top choice for your stay, based on our traveller data. Two other options for your stay in the area are Crowne Plaza Annapolis by IHG and Historic Inns of Annapolis. See all available top hotels, or vacation rentals in Chester.
What are some of the best holiday rentals that Chester has to offer?
Waterfront Home On 3 Acres. Fish,crab, & kayak from the pier + great sunsets!: This highly rated holiday home rental in Chester is located on the waterfront, 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 dishwasher, a fridge and a stovetop, 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 selection of games. Our travellers also rate Waterfront Sunset Bayview: sleeps 6 as a favourite home for rent in Chester. 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. Features free self parking, an indoor pool and complimentary wireless Internet access. Sonesta ES Suites Annapolis and Country Inn & Suites by Radisson, Annapolis, MD 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 10 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 Chesapeake Bay Environmental Center. You'll also find Love Point State Park and Eastern Neck National Wildlife Refuge 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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