Photo by Patricia Knorr

Chester hotels from RM252

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Check prices for these dates

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9 Jul - 10 Jul
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11 Jul - 13 Jul
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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, (867)
"Great place"
The price is RM471
RM523 total
includes taxes & fees
20 Jul - 21 Jul
Holiday Inn Express Annapolis East-Kent Island by IHG
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 RM645
RM716 total
includes taxes & fees
4 Aug - 5 Aug
Hyatt Place Kent Narrows & Marina
Hilton Garden Inn Kent Island Marina
Terrace/patio

Hilton Garden Inn Kent Island Marina

3.0 star property
9.0 out of 10, Wonderful, (956)
"Great stay. We have stayed multiple times throughout the years and the quality has always been excellent."
The price is RM644
RM715 total
includes taxes & fees
20 Jul - 21 Jul
Hilton Garden Inn Kent Island Marina
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, (1000)
"I liked the spacious room and Jacuzzi. The free breakfast was good and staff was Amazing!"
The price is RM386
RM440 total
includes taxes & fees
20 Jul - 21 Jul
Hilton Garden Inn Annapolis
The Westin Annapolis
City view from property

The Westin Annapolis

4.0 star property
8.6 out of 10, Excellent, (1002)
"Easy downtown location, walkable to waterfront and great restaurants "
The price is RM695
RM792 total
includes taxes & fees
20 Jul - 21 Jul
The Westin Annapolis
Courtyard by Marriott Annapolis
Exterior

Courtyard by Marriott Annapolis

3.0 star property
8.6 out of 10, Excellent, (1003)
"Pleasant stay!!"
The price is RM424
RM483 total
includes taxes & fees
24 Jul - 25 Jul
Courtyard by Marriott Annapolis
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, (837)
"Front desk staff was very friendly and helpful."
The price is RM988
RM1,127 total
includes taxes & fees
24 Jul - 25 Jul
Annapolis Waterfront Hotel, Autograph Collection
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 RM403
RM459 total
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
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 RM437
RM498 total
includes taxes & fees
20 Jul - 21 Jul
Holiday Inn Express & Suites Annapolis by IHG
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 RM911
RM1,119 total
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 RM428
RM488 total
includes taxes & fees
20 Jul - 21 Jul
Country Inn & Suites by Radisson, Annapolis, MD
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 RM384
RM438 total
includes taxes & fees
24 Jul - 25 Jul
Hampton Inn & Suites Annapolis
SpringHill Suites by Marriott Annapolis
Exterior

SpringHill Suites by Marriott Annapolis

3.0 star property
9.0 out of 10, Wonderful, (1000)
"Great location , clean and friendly staff "
The price is RM414
RM472 total
includes taxes & fees
28 Jul - 29 Jul
SpringHill Suites by Marriott Annapolis
Wylder Tilghman Island
Living area

Wylder Tilghman Island

2.0 star property
8.8 out of 10, Excellent, (49)
"Excellent stay. Very relaxing and great facilities."
The price is RM762
RM1,008 total
includes taxes & fees
17 Jul - 18 Jul
Wylder Tilghman Island
Kent Island Resort
Aerial view

Kent Island Resort

3.5 star property
9.2 out of 10, Wonderful, (104)
"Welcoming and well-staffed property, in a lovely and tranquil setting. Staff was friendly and helpful. Restaurant/bar service and food were outstanding. Great quiet getaway weekend spot. "
The price is RM1,025
RM1,306 total
includes taxes & fees
22 Jul - 23 Jul
Kent Island Resort
Hilton Garden Inn Annapolis Downtown
Living area

Hilton Garden Inn Annapolis Downtown

3.0 star property
8.6 out of 10, Excellent, (1008)
"Really nice place to stay and enjoy Annapolis "
The price is RM421
RM480 total
includes taxes & fees
4 Aug - 5 Aug
Hilton Garden Inn Annapolis Downtown
Fairfield Inn & Suites By Marriott Annapolis
Property amenity

Fairfield Inn & Suites By Marriott Annapolis

3.0 star property
9.0 out of 10, Wonderful, (104)
"Wonderful stay. "
The price is RM538
RM613 total
includes taxes & fees
20 Jul - 21 Jul
Fairfield Inn & Suites By Marriott Annapolis
Crowne Plaza Annapolis by IHG
Pool

Crowne Plaza Annapolis by IHG

3.5 star property
8.8 out of 10, Excellent, (1004)
The price is RM457
RM521 total
includes taxes & fees
20 Jul - 21 Jul
Crowne Plaza Annapolis by IHG
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 RM420
RM479 total
includes taxes & fees
13 Jul - 14 Jul
Sonesta ES Suites 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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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.