Photo by Patricia Knorr

Chester Hotels from S$117

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12 Oct - 13 Oct
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Top 10 trending Chester hotels

Holiday Inn Express Annapolis East-Kent Island by IHG
Exterior

Holiday Inn Express Annapolis East-Kent Island by IHG

2.5 star property
9.2 out of 10, Wonderful, (906)
"Nice Holiday Inn Express with great water views."
The price is S$171
includes taxes & fees
10 Nov - 11 Nov
Holiday Inn Express Annapolis East-Kent Island by IHG
The Westin Annapolis
View from property

The Westin Annapolis

4.0 star property
8.6 out of 10, Excellent, (1003)
"Would stay there again very soon "
The price is S$288
includes taxes & fees
2 Nov - 3 Nov
The Westin Annapolis
Hyatt Place Kent Narrows & Marina
Terrace/patio

Hyatt Place Kent Narrows & Marina

3.0 star property
9.4 out of 10, Exceptional, (638)
"Great location and rooms. Great place!"
The price is S$207
includes taxes & fees
21 Oct - 22 Oct
Hyatt Place Kent Narrows & Marina
Kent Island Resort
Aerial view

Kent Island Resort

3.5 star property
9.2 out of 10, Wonderful, (114)
"Great INN super nice staff"
The price is S$317
includes taxes & fees
13 Oct - 14 Oct
Kent Island Resort
Hilton Garden Inn Kent Island Marina
Terrace/patio

Hilton Garden Inn Kent Island Marina

3.0 star property
9.0 out of 10, Wonderful, (1003)
"Hotel was great, beautiful location near the water"
The price is S$211
includes taxes & fees
26 Oct - 27 Oct
Hilton Garden Inn Kent Island Marina
Courtyard by Marriott Annapolis
Exterior

Courtyard by Marriott Annapolis

3.0 star property
8.6 out of 10, Excellent, (1001)
"The room was great, and the staff was great. "
The price is S$161
includes taxes & fees
2 Nov - 3 Nov
Courtyard by Marriott Annapolis
Hilton Garden Inn Annapolis
Hypo-allergenic bedding, in-room safe, desk, iron/ironing board

Hilton Garden Inn Annapolis

3.0 star property
8.2 out of 10, Very good, (1007)
"Our stay at the hotel was easy check in and check out. Quiet and great location for our stay."
The price is S$135
includes taxes & fees
2 Nov - 3 Nov
Hilton Garden Inn Annapolis
Hampton Inn & Suites Annapolis
Premium bedding, pillow-top beds, in-room safe, individually furnished

Hampton Inn & Suites Annapolis

2.5 star property
8.2 out of 10, Very good, (1008)
"We had a nice stay. "
The price is S$139
includes taxes & fees
2 Nov - 3 Nov
Hampton Inn & Suites Annapolis
Historic Inns of Annapolis
Terrace/patio

Historic Inns of Annapolis

3.5 star property
9.0 out of 10, Wonderful, (1846)
"Perfect location…terrific staff…spacious room with a king sized bed! "
Historic Inns of Annapolis
Country Inn & Suites by Radisson, Annapolis, MD
1 bedroom, hypo-allergenic bedding, desk, blackout curtains

Country Inn & Suites by Radisson, Annapolis, MD

3.0 star property
9.0 out of 10, Wonderful, (1010)
"Great place to stay Friendly staff secure rooms Thank you "
The price is S$143
includes taxes & fees
2 Nov - 3 Nov
Country Inn & Suites by Radisson, Annapolis, MD
DoubleTree by Hilton Hotel Annapolis
Garden

DoubleTree by Hilton Hotel Annapolis

4.0 star property
8.6 out of 10, Excellent, (1014)
"Comfortable place to stay, nice shopping area close by. "
The price is S$157
includes taxes & fees
3 Nov - 4 Nov
DoubleTree by Hilton Hotel Annapolis
Crowne Plaza Annapolis by IHG
Indoor pool

Crowne Plaza Annapolis by IHG

3.5 star property
8.8 out of 10, Excellent, (1002)
"Good location"
The price is S$148
includes taxes & fees
3 Nov - 4 Nov
Crowne Plaza Annapolis by IHG
Sonesta ES Suites Annapolis
Egyptian cotton sheets, premium bedding, pillow-top beds, desk

Sonesta ES Suites Annapolis

3.0 star property
8.8 out of 10, Excellent, (912)
"Had a great stay."
The price is S$129
includes taxes & fees
9 Nov - 10 Nov
Sonesta ES Suites Annapolis
Village Inn Annapolis MD
Reception

Village Inn Annapolis MD

2.0 star property
6.2 out of 10, (504)
"The room was very nice, clean and quiet. Great location"
The price is S$123
includes taxes & fees
2 Nov - 3 Nov
Village Inn Annapolis MD
Annapolis Waterfront Hotel, Autograph Collection
Premium bedding, down duvets, pillow-top beds, in-room safe

Annapolis Waterfront Hotel, Autograph Collection

4.0 star property
8.8 out of 10, Excellent, (871)
"Clean room. Friendly staff awesome location. "
The price is S$300
includes taxes & fees
9 Nov - 10 Nov
Annapolis Waterfront Hotel, Autograph Collection
SpringHill Suites by Marriott Annapolis
Free daily self-service breakfast

SpringHill Suites by Marriott Annapolis

3.0 star property
9.0 out of 10, Wonderful, (1005)
"Clean room, Good breakfast and friendly staff."
The price is S$156
includes taxes & fees
2 Nov - 3 Nov
SpringHill Suites by Marriott Annapolis
The Inn at Chesapeake Bay Beach Club
Front of property – evening/night

The Inn at Chesapeake Bay Beach Club

4.0 star property
9.4 out of 10, Exceptional, (421)
"Beautiful hotel with friendly staff and great food! Comfortable bed, stayed at the Barn. "
The price is S$312
includes taxes & fees
9 Nov - 10 Nov
The Inn at Chesapeake Bay Beach Club
The Tilghman Island Inn
Outdoor banquet area

The Tilghman Island Inn

3.5 star property
9.6 out of 10, Exceptional, (114)
"Great staff and food!"
The price is S$285
includes taxes & fees
2 Nov - 3 Nov
The Tilghman Island Inn
Graduate by Hilton Annapolis
View from property

Graduate by Hilton Annapolis

4.0 star property
9.4 out of 10, Exceptional, (1007)
"Great area and it was a perfect hotel for our trip. "
The price is S$229
includes taxes & fees
10 Nov - 11 Nov
Graduate by Hilton Annapolis
Holiday Inn Express & Suites Annapolis by IHG
Free daily buffet breakfast

Holiday Inn Express & Suites Annapolis by IHG

2.5 star property
8.2 out of 10, Very good, (1000)
"Great location. "
The price is S$159
includes taxes & fees
26 Oct - 27 Oct
Holiday Inn Express & Suites Annapolis by IHG
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

The Westin Annapolis

The Westin Annapolis

10/10 Excellent
"excellent service for our Remodelers Advantage Conference. Food was delicious and service to the rooms for snacks was great as well"
Jennifer 2-night trip
Posted 3 days ago
The Westin Annapolis

More cheap stays in Chester

Best Western Annapolis

Best Western Annapolis

2520 Riva Rd, Annapolis, MD
The price is S$117 per night from 9 Nov to 10 Nov
S$117
9 Nov - 10 Nov
includes taxes & fees
7.6/10 Good! (1,004 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 Sonesta ES Suites Annapolis and Country Inn & Suites by Radisson, Annapolis, MD. 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 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?
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 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 15 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 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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