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Find hotels in Chester, MD from ￥12,874

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Our top choices for Chester hotels

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Graduate by Hilton Annapolis

Graduate by Hilton Annapolis

Graduate by Hilton Annapolis
4.0 star property
Annapolis
9.4 out of 10, Exceptional, (1003)
This tranquil hotel offers a serene retreat with comfortable beds and stylish Trophy Room for dinner. Explore local attractions using free bike rentals, or unwind at the bar after a workout in the 24-hour fitness center.
"Pleasant staff. Good location to walk to restaurants, shops. "
United States
Beth
The price is ￥23,021
￥26,244 total
includes taxes & fees
Jan 11 - Jan 12
Graduate by Hilton Annapolis
View from property
The Westin Annapolis

The Westin Annapolis

The Westin Annapolis
4.0 star property
Annapolis
8.6 out of 10, Excellent, (1002)
Discover peaceful luxury in Annapolis with a full-service spa offering massages and facials. After enjoying Captain's Daughter restaurant, take a refreshing dip in the indoor pool or maintain your workout routine at the 24-hour fitness center.
"Great hotel love that they are pet friendly. Easy check in and valet parking staff great"
United States
Robert
The price is ￥21,801
￥24,854 total
includes taxes & fees
Jan 6 - Jan 7
The Westin Annapolis
Indoor pool
Crowne Plaza Annapolis by IHG

Crowne Plaza Annapolis by IHG

Crowne Plaza Annapolis by IHG
3.5 star property
Annapolis
8.8 out of 10, Excellent, (1018)
Dive into comfort at this Annapolis hotel with a serene indoor pool, onsite restaurant, and bar. Just 10 minutes from the Naval Academy and steps from Westfield Mall, guests love the peaceful atmosphere, attentive staff, and clean rooms.
"Very nice hotel. Very clean and quiet "
United States
Mary
The price is ￥17,252
￥19,668 total
includes taxes & fees
Jan 8 - Jan 9
Crowne Plaza Annapolis by IHG
Free daily self-serve breakfast
SpringHill Suites by Marriott Annapolis

SpringHill Suites by Marriott Annapolis

SpringHill Suites by Marriott Annapolis
3.0 star property
Annapolis
9.0 out of 10, Wonderful, (1002)
"Great location and friendly staff. "
United States
Shana
The price is ￥17,198
￥19,606 total
includes taxes & fees
Jan 11 - Jan 12
SpringHill Suites by Marriott Annapolis
Garden
DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis
4.0 star property
Annapolis
8.6 out of 10, Excellent, (1005)
Located just 5 minutes from U.S. Naval Academy, this hotel offers convenient access to Annapolis Harbor Center and Westfield Annapolis Mall. Enjoy the 24-hour fitness center, restaurant serving 3 meals daily, and garden. Guests particularly praise the helpful staff and prime location.
"Great stay "
United States
Jose Miguel
The price is ￥12,989
￥14,808 total
includes taxes & fees
Jan 11 - Jan 12
DoubleTree by Hilton Hotel Annapolis
Terrace/patio
Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina
3.0 star property
Grasonville
9.6 out of 10, Exceptional, (693)
Experience a refreshing stay at this waterfront hotel with an indoor pool and helpful staff. Just minutes from Chesapeake Bay Environmental Center and Paul Reed Smith Guitars, enjoy convenient access to local attractions with free WiFi and parking.
"Good breakfast, great view, clean and well run, pleasant staff, great dining options nearby. "
United States
Kevin
The price is ￥18,193
￥20,194 total
includes taxes & fees
Jan 19 - Jan 20
Hyatt Place Kent Narrows & Marina
Terrace/patio
Historic Inns of Annapolis

Historic Inns of Annapolis

Historic Inns of Annapolis
3.5 star property
Historic District
9.0 out of 10, Wonderful, (1908)
Immerse in Maryland's maritime heritage at this historic hotel with a 24-hour fitness center and garden terrace. Just a short walk from the U.S. Naval Academy and colonial attractions, this hotel offers comfortable beds and exceptional service.
" Great place to stay!"
United States
Lewis
Historic Inns of Annapolis
Front of property - evening/night
The Inn at Chesapeake Bay Beach Club

The Inn at Chesapeake Bay Beach Club

The Inn at Chesapeake Bay Beach Club
4.0 star property
Stevensville
9.4 out of 10, Exceptional, (433)
Located in Stevensville with easy access to Paul Reed Smith Guitars and Northern Chesapeake Bay, this hotel offers spa treatments, an outdoor pool, and a café. Enjoy free WiFi and parking while the helpful staff ensures a memorable stay.
"Very nice and clean! Only complaints A few stains on the couch And no body lotion. We really enjoyed our stay! "
United States
DEANNA
The price is ￥24,459
￥31,140 total
includes taxes & fees
Feb 1 - Feb 2
The Inn at Chesapeake Bay Beach Club
Hypo-allergenic bedding, desk, blackout drapes, iron/ironing board
Country Inn & Suites by Radisson, Annapolis, MD

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, (1006)
Just 10 minutes from the U.S. Naval Academy, this serene hotel offers free parking and WiFi. Unwind in the indoor pool and hot tub after exploring nearby Westfield Annapolis Mall and local restaurants. Guests consistently praise the peaceful atmosphere and attentive staff.
"Breakfast menu was great! Pool and hot tub were nice!"
United States
Terrence
The price is ￥15,170
￥17,294 total
includes taxes & fees
Jan 8 - Jan 9
Country Inn & Suites by Radisson, Annapolis, MD
Premium bedding, pillowtop beds, in-room safe, individually furnished
Hampton Inn & Suites Annapolis

Hampton Inn & Suites Annapolis

Hampton Inn & Suites Annapolis
2.5 star property
Annapolis
8.2 out of 10, Very Good, (1010)
Located within a 10-minute drive of U.S. Naval Academy, this hotel offers a seasonal outdoor pool and fitness center. Guests praise the helpful staff and free breakfast. Annapolis Harbor Center Shopping Center is nearby for all your needs.
"Appreciated that it was in a quiet area. Great hospitality! Will stay again when visiting Maryland."
United States
robin
The price is ￥14,018
￥15,980 total
includes taxes & fees
Jan 11 - Jan 12
Hampton Inn & Suites Annapolis
Premium Room | Frette Italian sheets, premium bedding, iron/ironing board, free WiFi
The Wildset

The Wildset

The Wildset
2.5 star property
Downtown St. Michaels
9.8 out of 10, Exceptional, (413)
Located in St. Michaels, this welcoming hotel offers free breakfast, WiFi, and parking. Enjoy drinks at the bar or grab a bite at the café. Nearby attractions include Higgins Yacht Yard and Muskrat Park, with attentive staff to enhance your stay.
"Everything was lovely. "
United States
Erin
The price is ￥28,074
￥34,331 total
includes taxes & fees
Jan 6 - Jan 7
The Wildset
Lobby
Best Western Plus Easton Inn & Suites

Best Western Plus Easton Inn & Suites

Best Western Plus Easton Inn & Suites
2.5 star property
Easton
9.2 out of 10, Wonderful, (1003)
Start your day with a refreshing swim in the indoor pool before exploring nearby Talbot Massage and Easton Cycle and Sport. Free WiFi, parking, and fitness center enhance your stay at this business-friendly hotel where helpful staff ensure comfort.
"Spacious room, friendly staff, nice bathroom. Everyone is very accommodating."
United States
DONNA
The price is ￥18,664
￥20,530 total
includes taxes & fees
Jan 6 - Jan 7
Best Western Plus Easton Inn & Suites
Suite, 1 Bedroom, Terrace | Living area | 42-inch LED TV with digital channels, TV
Hilton Garden Inn Annapolis Downtown

Hilton Garden Inn Annapolis Downtown

Hilton Garden Inn Annapolis Downtown
3.0 star property
Annapolis
8.6 out of 10, Excellent, (1007)
Experience Art Deco style at this downtown Annapolis hotel, just minutes from the U.S. Naval Academy. Enjoy regional cuisine at Kitchen on West St, unwind at the bar/lounge, or maintain your routine in the 24-hour fitness center.
"Great value for stay with breakfast included "
United States
Aisling
The price is ￥14,439
￥16,460 total
includes taxes & fees
Jan 26 - Jan 27
Hilton Garden Inn Annapolis Downtown
Terrace/patio
Hilton Garden Inn Kent Island Marina

Hilton Garden Inn Kent Island Marina

Hilton Garden Inn Kent Island Marina
3.0 star property
Grasonville
9.0 out of 10, Wonderful, (1001)
Overlooking the bay in Grasonville, this hotel offers an indoor pool and fitness center for active travelers. Explore nearby Chesapeake Bay Environmental Center, then unwind with drinks at the bar. Rooms include microwaves and refrigerators for added convenience.
"Clean and friendly staff"
United States
Lisa
The price is ￥19,163
￥21,271 total
includes taxes & fees
Jan 11 - Jan 12
Hilton Garden Inn Kent Island Marina
Room, 2 Queen Beds, Balcony | Premium bedding, down comforters, pillowtop beds, in-room safe
Annapolis Waterfront Hotel, Autograph Collection

Annapolis Waterfront Hotel, Autograph Collection

Annapolis Waterfront Hotel, Autograph Collection
4.0 star property
Historic District
8.8 out of 10, Excellent, (896)
Located steps from Ego Alley and Susan Campbell Park, this hotel offers Caribbean cuisine at Pussers Grille and panoramic harbor views. Enjoy luxury yacht sightings, a 24-hour fitness center, and quick access to the U.S. Naval Academy.
"Great location, nice and clean "
United States
Micah
The price is ￥29,196
￥33,283 total
includes taxes & fees
Jan 11 - Jan 12
Annapolis Waterfront Hotel, Autograph Collection
Porch
Hummingbird Inn

Hummingbird Inn

Hummingbird Inn
3.5 star property
Easton
10.0 out of 10, Exceptional, (86)
Relax at this enchanting Victorian B&B with pampering spa massages and a 24-hour fitness center. Located near Easton Rail Depot and Avalon Theatre, guests enjoy in-room refrigerators, microwaves, and a rejuvenating hot tub, plus free breakfast, WiFi, and parking.
"This place is the cutest and they are the nicest people! The breakfast is delicious!!"
Canada
Chrystine
Hummingbird Inn
Exterior
Knapps Narrows Marina & Inn

Knapps Narrows Marina & Inn

Knapps Narrows Marina & Inn
3.0 star property
Tilghman
9.4 out of 10, Exceptional, (364)
Discover serenity on the water at this Tilghman hotel with marina access, seasonal outdoor pool, and complimentary kayaking adventures. Comfortable rooms include refrigerators and microwaves, while free breakfast, WiFi and parking enhance your Chesapeake Bay getaway.
"nice clean room staff very nice would stay again "
United States
mario
The price is ￥15,684
￥17,252 total
includes taxes & fees
Jan 6 - Jan 7
Knapps Narrows Marina & Inn
Exterior
Courtyard by Marriott Annapolis

Courtyard by Marriott Annapolis

Courtyard by Marriott Annapolis
3.0 star property
Annapolis
8.6 out of 10, Excellent, (1004)
Situated just a short drive from the U.S. Naval Academy, this hotel offers American cuisine at The Bistro. Guests praise the peaceful atmosphere, helpful staff, and clean rooms. Free WiFi and parking enhance your stay near Annapolis Harbor Center.
"We keep coming back to the hotel with every visit to Annapolis. "
United States
Catherine
The price is ￥13,175
￥15,019 total
includes taxes & fees
Jan 25 - Jan 26
Courtyard by Marriott Annapolis
Free daily buffet breakfast
Holiday Inn Express & Suites Annapolis by IHG

Holiday Inn Express & Suites Annapolis by IHG

Holiday Inn Express & Suites Annapolis by IHG
2.5 star property
Annapolis
8.2 out of 10, Very Good, (1003)
Wake up to a delicious buffet breakfast at this Annapolis hotel, just 5 minutes from the U.S. Naval Academy. Enjoy complimentary WiFi and parking, plus a 24-hour fitness center. Located within easy walking distance to restaurants and shops.
"Clean room and friendly staff! "
United States
Silvia
The price is ￥12,547
￥14,304 total
includes taxes & fees
Jan 10 - Jan 11
Holiday Inn Express & Suites Annapolis by IHG
Exterior
Hampton Inn Easton

Hampton Inn Easton

Hampton Inn Easton
2.5 star property
Easton
9.0 out of 10, Wonderful, (557)
Wake up to a complimentary breakfast before exploring nearby Easton Cycle and Sport. This hotel offers an indoor pool for year-round swimming and a fitness center. Business travelers appreciate the free WiFi and parking with helpful staff.
"all excellent with kudos to staff and the breakfast cook."
United States
JOSEPH
The price is ￥18,291
￥20,120 total
includes taxes & fees
Jan 29 - Jan 30
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.
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Stay near popular Chester attractions

Chesapeake Exploration Center

Learn about the events happening at 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
Kent Narrows Maryland, USA, the narrows are just north of the Chesapeake bay and about an hour from Washington DC. Here the crabs are abundant and we had a great pick and peel crab dinner and Harrah's Crab house. Boats along this area go out each morning and pick the crabs out of the crab cages and get the catch of the day out in the Chesapeake bay . The Route 50 bridge is directly straight ahead, it the route into the Chesapeake bay bridge which is at least 3 miles long.
Photo by Patricia Knorr
Open Photo by Patricia Knorr

Top Chester Hotel Reviews

Sonesta ES Suites Annapolis

Sonesta ES Suites Annapolis

10/10 Excellent
"Staff was extremely friendly and helpful. Breakfast was delicious. Hotel was very clean and comfortable. We loved our room. Kitchen very useful as we brought leftovers and were able to heat them up in room and didn't need to go out to restaurant. Very comfortable mattress. All in all an excellent stay."
Linda Ann 2-night trip
Posted 1 day ago
Sonesta ES Suites Annapolis

More cheap stays in Chester

Best Western Annapolis

Best Western Annapolis

2520 Riva Rd Annapolis MD
The price is ￥11,292 per night from Jan 10 to Jan 11
￥11,292
￥12,874 total
Jan 10 - Jan 11
includes taxes & fees
7.6/10 Good! (1,005 reviews)

Frequently asked questions

What's the best place to stay in Chester?
Located 13.8 mi (22.2 km) from the heart of Chester, DoubleTree by Hilton Hotel Annapolis is a top choice for your stay based on our traveler data. Other good choices for your visit to the area are Historic Inns of Annapolis and Crowne Plaza Annapolis by IHG. See all available top hotels, or vacation rentals in Chester.
What's the top vacation rental in Chester?
Woodland Retreat on Kent Island: 5 beds, 5 miles from Bay Bridge, on 5 acres.: You might want to consider this vacation home rental near Chester, which is located on a river and has a patio, a garden, and a barbecue grill to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a fridge, a stovetop, and a microwave, so you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a pool table. 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 room reservations are fully refundable if you cancel before the accommodation's cancellation deadline, which is usually within 24-48 hours of your check-in date. If your reservation is non-refundable, you might be able to still cancel and receive a refund within a 24-hour period of booking. Filter your search by fully refundable to find flexible hotel deals in Chester.
Where can I learn more about changing or cancelling my trip to Chester?
To find more details about rescheduling or cancelling your trip to Chester, head over to our customer service page.
What are some accommodations with pools in Chester?
Crowne Plaza Annapolis by IHG: Hotel located near U.S. Naval Academy. Provides free self parking, an indoor pool, and complimentary wireless internet access. Country Inn & Suites by Radisson, Annapolis, MD and The Westin Annapolis are a couple of other choices with an onsite 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 11 hotels and other accommodations 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. Check out what more 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 temp of 74°F, while the coldest months are January and February with an average of 39°F. Average annual precipitation for Chester is 56 inches.

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