Photo by Patricia Knorr

Chester Hotels from S$84

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9 Jul - 10 Jul
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10 Jul - 11 Jul
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11 Jul - 13 Jul
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18 Jul - 20 Jul

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Top 10 trending Chester hotels

The Wildset
1 bedroom, Frette Italian sheets, premium bedding, iron/ironing board

The Wildset

2.5 star property
9.8 out of 10, Exceptional, (333)
"The room was lovely - comfortable beds, it bathroom, nice toiletries. It’s quiet yet right in the center of town so you can walk to all the shops and restaurants. "
The price is S$336
includes taxes & fees
15 Jul - 16 Jul
The Wildset
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, (400)
"Staff was very polite and friendly. "
The price is S$338
includes taxes & fees
22 Jul - 23 Jul
The Inn at Chesapeake Bay Beach Club
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, (1001)
"Great location , perfect for my family stay."
The price is S$148
includes taxes & fees
16 Jul - 17 Jul
Country Inn & Suites by Radisson, Annapolis, MD
Graduate by Hilton Annapolis
View from property

Graduate by Hilton Annapolis

4.0 star property
9.4 out of 10, Exceptional, (1005)
"Loved our stay here, perfect place for an Annapolis weekend!"
The price is S$226
includes taxes & fees
3 Aug - 4 Aug
Graduate by Hilton Annapolis
Candlewood Suites Annapolis by IHG
Exterior

Candlewood Suites Annapolis by IHG

2.5 star property
8.6 out of 10, Excellent, (69)
"Great stay"
The price is S$133
includes taxes & fees
13 Jul - 14 Jul
Candlewood Suites Annapolis by IHG
Holiday Inn Express & Suites Annapolis by IHG
1 bedroom, in-room safe, desk, laptop workspace

Holiday Inn Express & Suites Annapolis by IHG

2.5 star property
8.2 out of 10, Very good, (1000)
"Decent property "
The price is S$150
includes taxes & fees
24 Jul - 25 Jul
Holiday Inn Express & Suites Annapolis by IHG
Knapps Narrows Marina & Inn
Exterior

Knapps Narrows Marina & Inn

3.0 star property
9.4 out of 10, Exceptional, (334)
"Extremely clean, wonderful place "
The price is S$310
includes taxes & fees
15 Jul - 16 Jul
Knapps Narrows Marina & Inn
Parsonage Inn
Porch

Parsonage Inn

3.5 star property
9.2 out of 10, Wonderful, (128)
"Beautiful Victorian Cottage Home. Outstanding service and breakfast. Wonderful hosts made us feel right @ home!"
The price is S$366
includes taxes & fees
10 Jul - 11 Jul
Parsonage Inn
St Michaels Inn
Front of property

St Michaels Inn

2.5 star property
8.2 out of 10, Very good, (1002)
"Great spot to be close to town for a modest price. "
The price is S$158
includes taxes & fees
21 Jul - 22 Jul
St Michaels Inn
Hyatt Place Kent Narrows & Marina
Terrace/patio

Hyatt Place Kent Narrows & Marina

3.0 star property
9.4 out of 10, Exceptional, (576)
"Great place to stay. "
The price is S$216
includes taxes & fees
4 Aug - 5 Aug
Hyatt Place Kent Narrows & Marina
Best Western Kent Narrows Inn
In-room safe, individually decorated, individually furnished, desk

Best Western Kent Narrows Inn

2.5 star property
8.2 out of 10, Very good, (1000)
"Second time staying, it’s priced right, great staff, and amazing restaurants right across the street, quiet area right by the bay bridge. "
The price is S$180
includes taxes & fees
24 Jul - 25 Jul
Best Western Kent Narrows Inn
TownePlace Suites by Marriott Annapolis
Exterior

TownePlace Suites by Marriott Annapolis

3.0 star property
9.0 out of 10, Wonderful, (13)
"Everyone at the front desk was extremely friendly and helpful."
The price is S$147
includes taxes & fees
24 Jul - 25 Jul
TownePlace Suites by Marriott Annapolis
Anchored Inn at Hidden Harbour Marina
Front of property

Anchored Inn at Hidden Harbour Marina

2.5 star property
9.4 out of 10, Exceptional, (439)
"The staff specifically Victoria was impeccable! "
The price is S$353
includes taxes & fees
17 Jul - 18 Jul
Anchored Inn at Hidden Harbour Marina
DoubleTree by Hilton Hotel Annapolis
Lobby

DoubleTree by Hilton Hotel Annapolis

4.0 star property
8.6 out of 10, Excellent, (1000)
"Excellent hospitable staff made the stay even better!"
The price is S$139
includes taxes & fees
3 Aug - 4 Aug
DoubleTree by Hilton Hotel Annapolis
Historic Inns of Annapolis
Exterior

Historic Inns of Annapolis

3.5 star property
9.0 out of 10, Wonderful, (1795)
"Wonderful stay!"
Historic Inns of 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, (1004)
"Clean and comfortable room a with friendly service. Also in a great location to access the surrounding area. "
The price is S$132
includes taxes & fees
24 Jul - 25 Jul
Hampton Inn & Suites Annapolis
Inn at Perry Cabin
Breakfast, lunch, dinner served; sea views

Inn at Perry Cabin

5.0 star property
9.6 out of 10, Exceptional, (353)
"Grounds are beautiful. Staff very friendly and attentive "
The price is S$968
includes taxes & fees
13 Jul - 14 Jul
Inn at Perry Cabin
86 State Circle - Luxury Boutique Hotel
Exterior

86 State Circle - Luxury Boutique Hotel

2.0 star property
10.0 out of 10, Exceptional, (1)
The price is S$370
includes taxes & fees
13 Jul - 14 Jul
86 State Circle - Luxury Boutique Hotel
Sonesta ES Suites Annapolis
1 bedroom, Egyptian cotton sheets, premium bedding, pillow-top beds

Sonesta ES Suites Annapolis

3.0 star property
8.8 out of 10, Excellent, (834)
"Room was large & bed very comfortable. Very pleasant stay"
The price is S$144
includes taxes & fees
13 Jul - 14 Jul
Sonesta ES Suites Annapolis
Inn at Horn Point
Beach nearby

Inn at Horn Point

3.0 star property
9.4 out of 10, Exceptional, (19)
"This B&B was centrally located, clean,safe and quiet. However, even though I knew there would be no breakfast, I thought that like most B&B’s there would be the possibility of coffee or tea in the morning. There was no one home to welcome us or give information about nearby restaurants, etc. Why take the reservation if you can’t provide the amenities most B&B’s feature?"
The price is S$516
includes taxes & fees
4 Aug - 5 Aug
Inn at Horn Point
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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Family-friendly hotels in Chester you'll enjoy

Hampton Inn Easton
Exterior

Hampton Inn Easton

2.5 star property
9.0 out of 10, Wonderful, (516)
The price is S$210
includes taxes & fees
14 Jul - 15 Jul
Hampton Inn Easton

Hotels with a spa in Chester may fit your trip

Hummingbird Inn
Porch

Hummingbird Inn

3.5 star property
10.0 out of 10, Exceptional, (76)
Hummingbird Inn

Check out pet-friendly hotels in Chester

Hampton Inn Easton
Exterior

Hampton Inn Easton

2.5 star property
9.0 out of 10, Wonderful, (516)
The price is S$210
includes taxes & fees
14 Jul - 15 Jul
Hampton Inn Easton
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.

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

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 DoubleTree by Hilton Hotel Annapolis and Hilton Garden Inn Annapolis Downtown. 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. Best Western 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 14 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 Sandy Point Beach and Queenstown Harbor Golf Club 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.