Photo by Patricia Knorr

Chester Hotels from S$83

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Tonight
15 Jun - 16 Jun
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16 Jun - 17 Jun
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20 Jun - 22 Jun
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27 Jun - 29 Jun

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Top 10 trending Chester hotels

Mariners Motel
Outdoor pool

Mariners Motel

2.0 star property
9.4 out of 10, Exceptional, (89)
"Very nice old school motel just about on the water in Rock Hall. Perfect if you’re in town for marina stuff. "
The price is S$221
includes taxes & fees
18 Jun - 19 Jun
Mariners Motel
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, (391)
"Beautiful place, quiet and clean. "
The price is S$324
includes taxes & fees
9 Jul - 10 Jul
The Inn at Chesapeake Bay Beach Club
Graduate by Hilton Annapolis
View from property

Graduate by Hilton Annapolis

4.0 star property
9.4 out of 10, Exceptional, (1001)
"Loved our stay here, perfect place for an Annapolis weekend!"
The price is S$227
includes taxes & fees
6 Jul - 7 Jul
Graduate by Hilton Annapolis
Hyatt Place Kent Narrows & Marina
Terrace/patio

Hyatt Place Kent Narrows & Marina

3.0 star property
9.6 out of 10, Exceptional, (552)
"Clean, nice rooms and nice views"
The price is S$222
includes taxes & fees
15 Jul - 16 Jul
Hyatt Place Kent Narrows & Marina
Best Western Plus Easton Inn & Suites
Lobby

Best Western Plus Easton Inn & Suites

2.5 star property
9.4 out of 10, Exceptional, (1004)
"Great value!"
The price is S$182
includes taxes & fees
16 Jun - 17 Jun
Best Western Plus Easton Inn & Suites
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, (434)
"Beautiful hotel inside and out "
The price is S$354
includes taxes & fees
16 Jun - 17 Jun
Anchored Inn at Hidden Harbour Marina
Knapps Narrows Marina & Inn
Exterior

Knapps Narrows Marina & Inn

3.0 star property
9.4 out of 10, Exceptional, (332)
"Extremely clean, wonderful place "
The price is S$212
includes taxes & fees
16 Jun - 17 Jun
Knapps Narrows Marina & Inn
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$517
includes taxes & fees
7 Jul - 8 Jul
Inn at Horn Point
Hilton Garden Inn Kent Island Marina
Terrace/patio

Hilton Garden Inn Kent Island Marina

3.0 star property
9.0 out of 10, Wonderful, (939)
"Very nice place to stay. Will definitely stay there again!"
The price is S$205
includes taxes & fees
29 Jun - 30 Jun
Hilton Garden Inn Kent Island Marina
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, (848)
"Lovely place and stay…"
The price is S$164
includes taxes & fees
13 Jul - 14 Jul
Holiday Inn Express Annapolis East-Kent Island by IHG
The Tidewater Inn
Terrace/patio

The Tidewater Inn

3.0 star property
8.8 out of 10, Excellent, (799)
"Nice place"
The price is S$238
includes taxes & fees
30 Jun - 1 Jul
The Tidewater Inn
Inn at Huntingfield Creek
Lake

Inn at Huntingfield Creek

3.5 star property
10.0 out of 10, Exceptional, (50)
"Lovely property with wonderful owners and staff, including three very welcoming dogs. We had a perfect weekend getaway."
Inn at Huntingfield Creek
Historic Inns of Annapolis
Exterior

Historic Inns of Annapolis

3.5 star property
9.0 out of 10, Wonderful, (1776)
"Nice historic hotel close to Main Street. "
Historic Inns of Annapolis
Candlewood Suites Annapolis by IHG
Exterior

Candlewood Suites Annapolis by IHG

2.5 star property
8.6 out of 10, Excellent, (52)
"Great location"
The price is S$143
includes taxes & fees
18 Jun - 19 Jun
Candlewood Suites Annapolis by IHG
Wylder Tilghman Island
Living area

Wylder Tilghman Island

2.0 star property
8.8 out of 10, Excellent, (40)
"Always love staying here. This was my third visit. "
The price is S$292
includes taxes & fees
23 Jun - 24 Jun
Wylder Tilghman Island
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)
"One of the homiest Inn in the area "
The price is S$148
includes taxes & fees
2 Jul - 3 Jul
Country Inn & Suites by Radisson, Annapolis, MD
Inn at Perry Cabin
Breakfast, lunch, dinner served; sea views

Inn at Perry Cabin

5.0 star property
9.6 out of 10, Exceptional, (347)
"Very enjoyable stay."
The price is S$1,247
includes taxes & fees
24 Jun - 25 Jun
Inn at Perry Cabin
Crowne Plaza Annapolis by IHG
Pool

Crowne Plaza Annapolis by IHG

3.5 star property
8.8 out of 10, Excellent, (1001)
"Great bar and buffet. Open early for breakfast if you’re in a hurry. "
The price is S$158
includes taxes & fees
18 Jun - 19 Jun
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, (821)
"Big rooms and easy access to main road and highways."
The price is S$157
includes taxes & fees
17 Jun - 18 Jun
Sonesta ES Suites Annapolis
134 Prince - Luxury Boutique Hotel
Front of property

134 Prince - Luxury Boutique Hotel

2.5 star property
9.6 out of 10, Exceptional, (20)
"Great boutique hotel for an overnight. Terrific location and accommodating staff. Couldn't have been a better stay. "
134 Prince - Luxury Boutique Hotel
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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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

More cheap stays in Chester

More cheap stays in Chester

Candlewood Suites Annapolis by IHG

Candlewood Suites Annapolis by IHG

1 Womack Dr, Annapolis, MD
The price is S$143 per night from 18 Jun to 19 Jun
S$143
18 Jun - 19 Jun
includes taxes & fees
8.6/10 Excellent! (50 reviews)

Hotels near Chester Attractions

Hotels near Chester Attractions

Recent Reviews in Chester

Recent Reviews in Chester

Historic Inns of Annapolis

Historic Inns of Annapolis

5/5 Excellent
"Great location near the dock! "
A verified traveller stayed at Historic Inns of Annapolis
Posted 1 day ago
Historic Inns of Annapolis

Explore a world of travel with Expedia

Explore a world of travel with Expedia

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 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 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. SpringHill Suites by Marriott Annapolis and Hyatt Place Kent Narrows & Marina 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 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.