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Our top choices for Chester hotels

Holiday Inn Express Annapolis East-Kent Island by IHG

Holiday Inn Express Annapolis East-Kent Island by IHG
2.5 star property
Grasonville
9.2 out of 10, Wonderful, (961 reviews)
"Clean room, I enjoy staying here every time I'm in the area"
United States
Peter
The price is AU$150
includes taxes & fees
23 Feb - 24 Feb
Holiday Inn Express Annapolis East-Kent Island by IHG

Quality Inn

Quality Inn
2.5 star property
Easton
7.6 out of 10, Good, (845 reviews)
"Checkin staff was great. The motel is advertised as a HOTEL, and it very clearly is not."
United States
Jennifer
The price is AU$133
includes taxes & fees
8 Mar - 9 Mar
Quality Inn

Quality Inn Grasonville near Kent Island

Quality Inn Grasonville near Kent Island
2.5 star property
Grasonville
7.8 out of 10, Good, (875 reviews)
"Nice staff and rooms"
United States
Walter
The price is AU$132
includes taxes & fees
16 Mar - 17 Mar
Quality Inn Grasonville near Kent Island

Anchored Inn at Hidden Harbour Marina

Anchored Inn at Hidden Harbour Marina
2.5 star property
Deale
9.4 out of 10, Exceptional, (476 reviews)
"Beautiful place to stay, we stay their one to two times a year."
United States
Marjorie
The price is AU$217
includes taxes & fees
22 Feb - 23 Feb
Anchored Inn at Hidden Harbour Marina

Best Western Plus Easton Inn & Suites

Best Western Plus Easton Inn & Suites
2.5 star property
Easton
9.2 out of 10, Wonderful, (1,001 reviews)
"Nice friendly staff, clean room and lobby"
United States
Joi
The price is AU$186
includes taxes & fees
22 Feb - 23 Feb
Best Western Plus Easton Inn & Suites

Best Western Kent Narrows Inn

Best Western Kent Narrows Inn
2.5 star property
Grasonville
8.0 out of 10, Very good, (1,003 reviews)
"Nice breakfast, cleanroom. Great location."
United States
Wayne
The price is AU$148
includes taxes & fees
1 Mar - 2 Mar
Best Western Kent Narrows Inn

Knapps Narrows Marina & Inn

Knapps Narrows Marina & Inn
3.0 star property
Sherwood
9.4 out of 10, Exceptional, (370 reviews)
"Clean room, helpful staff, nice breakfast, beautiful views, excellent location."
United States
Denise
The price is AU$156
includes taxes & fees
24 Feb - 25 Feb
Knapps Narrows Marina & Inn

DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis
4.0 star property
Annapolis
8.6 out of 10, Excellent, (1,004 reviews)
"The staff were so nice and helpful and the amenities were great. The restaurant and bar were great especially the breakfast and of course the cookies. The shuttle was so convenient, fast, and super polite. Great stay. I recommend and will stay again next time I'm in town. "
United States
Kathy
The price is AU$134
includes taxes & fees
8 Mar - 9 Mar
DoubleTree by Hilton Hotel Annapolis

Wylder Tilghman Island

Wylder Tilghman Island
2.0 star property
Tilghman
8.8 out of 10, Excellent, (92 reviews)
"We were"
United States
Guevara
The price is AU$261
includes taxes & fees
1 Mar - 2 Mar
Wylder Tilghman Island

SpringHill Suites by Marriott Annapolis

SpringHill Suites by Marriott Annapolis
3.0 star property
Annapolis
9.0 out of 10, Wonderful, (1,001 reviews)
"Great location and friendly staff. "
United States
Shana
The price is AU$122
includes taxes & fees
8 Mar - 9 Mar
SpringHill Suites by Marriott Annapolis

Holiday Inn Express Easton by IHG

Holiday Inn Express Easton by IHG
3.0 star property
Easton
9.0 out of 10, Wonderful, (597 reviews)
"Everything was great!"
United States
HEATHER
The price is AU$201
includes taxes & fees
15 Mar - 16 Mar
Holiday Inn Express Easton by IHG

Hilton Garden Inn Kent Island Marina

Hilton Garden Inn Kent Island Marina
3.0 star property
Grasonville
9.0 out of 10, Wonderful, (1,000 reviews)
"Staff was friendly and rooms were clean. Beautiful area to visit. "
United States
Amy
The price is AU$179
includes taxes & fees
25 Feb - 26 Feb
Hilton Garden Inn Kent Island Marina

The Tilghman Island Inn

The Tilghman Island Inn
3.5 star property
Tilghman
9.6 out of 10, Exceptional, (121 reviews)
"Great room and water view! Staff is very friendly and welcoming. "
United States
Nicole
The price is AU$242
includes taxes & fees
21 Feb - 22 Feb
The Tilghman Island Inn

St Michaels Inn

St Michaels Inn
2.5 star property
St. Michaels
8.2 out of 10, Very good, (1,001 reviews)
"Good value and close to downtown."
United States
John
St Michaels Inn

The Tidewater Inn

The Tidewater Inn
3.0 star property
Easton
8.8 out of 10, Excellent, (853 reviews)
"Friendly staff, spotless room, great location. "
United States
Steven
The price is AU$271
includes taxes & fees
8 Mar - 9 Mar
The Tidewater Inn

Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina
3.0 star property
Grasonville
9.6 out of 10, Exceptional, (717 reviews)
"Amazing location and staff!"
United States
Bobbi J.
The price is AU$182
includes taxes & fees
2 Mar - 3 Mar
Hyatt Place Kent Narrows & Marina

Hampton Inn Easton

Hampton Inn Easton
2.5 star property
Easton
9.0 out of 10, Wonderful, (559 reviews)
"all excellent with kudos to staff and the breakfast cook."
United States
JOSEPH
The price is AU$184
includes taxes & fees
8 Mar - 9 Mar
Hampton Inn Easton

The Wildset

The Wildset
2.5 star property
Downtown St. Michaels
9.8 out of 10, Exceptional, (417 reviews)
"Clean rooms, great staff, awesome restaurant on site called Ruse & right in downtown. "
United States
Fred
The price is AU$310
includes taxes & fees
1 Mar - 2 Mar
The Wildset

Fairfield Inn & Suites By Marriott Annapolis

Fairfield Inn & Suites By Marriott Annapolis
3.0 star property
Annapolis
8.8 out of 10, Excellent, (178 reviews)
"Room was very nice and clean. Only thing that needs to change is the parking situation. They need more parking spaces. And they charge $30 for parking. "
United States
Cecilia
The price is AU$178
includes taxes & fees
25 Feb - 26 Feb
Fairfield Inn & Suites By Marriott Annapolis

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, (1,000 reviews)
"Wonderful staff, great options for breakfast, room is perfect and quiet and clean. The amenities work nicely, gym is great and Thai is where I would stay again in the future. "
United States
Amanda
The price is AU$147
includes taxes & fees
15 Mar - 16 Mar
Country Inn & Suites by Radisson, Annapolis, MD
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

Learn more about Chester

Chester awaits: its island views, sunny weather, golf and more!

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

Recent Reviews in Chester

More cheap accommodation in Chester

Find out more about Chester

Top reasons to visit Chester

  • Scenic Outdoor Activities: Chester offers a variety of outdoor pursuits, including beautiful beaches and recreational areas perfect for families.
  • Family-Friendly Attractions: Enjoy top spots like Chester Zoo and local parks, ensuring fun for all ages.
  • Rich Historical Exploration: Delve into Chester's intriguing history through its architectural sites and museums.
  • Charming Accommodation: From cosy B&Bs to family-friendly hotels, Chester has diverse lodging options to suit every traveller.
  • Nearby Countryside Escapes: Explore the picturesque Cheshire countryside for a relaxing day trip.

Find great hotels near Chester

Discover a charming selection of accommodation options in Chester, Maryland, perfect for every type of traveller. Whether you're seeking a family-friendly hotel, a cosy bed and breakfast, or a pet-friendly retreat, Chester has you covered. Enjoy convenient amenities tailored for business trips or leisurely holidays, ensuring a memorable stay in this picturesque town.

  • Country Inn & Suites by Radisson, Annapolis, MD: Embrace a warm and welcoming atmosphere at Country Inn & Suites by Radisson, Annapolis, MD. This charming 3-star hotel, located 22.5km from Chester, caters to diverse travelers, including those from the LGBTQIA community. Ideal for business trips, the hotel features multiple meeting rooms, a fully accessible business centre, and conference spaces. Pet lovers will appreciate the pet-friendly policy, complete with dog exercise areas and waived fees for service animals. The inviting environment and comprehensive business amenities make this hotel a comfortable choice for both work and leisure.
  • Graduate by Hilton Annapolis: Step into a world of collegiate charm at the Graduate by Hilton Annapolis, a 4-star establishment situated 17.7km from Chester. This hotel is perfect for LGBTQIA travellers and business professionals alike, offering a vibrant atmosphere inspired by university life. With modern meeting facilities and a business district location, it’s well-suited for corporate events. The hotel also welcomes pets, ensuring a delightful stay for all family members. With food and water bowls provided for furry friends, this property combines comfort, style, and functionality for a memorable experience.
  • Sonesta ES Suites Annapolis: Experience the comfort of home at Sonesta ES Suites Annapolis, a 3-star hotel located 22.5km from Chester. This property is designed for travellers seeking a pet-friendly and business-oriented environment. With a 24-hour business centre, meeting rooms, and a prime business location, it caters to professionals on the go. Guests with dogs will find ample amenities, including a dog exercise area and a welcoming pet policy. The inviting suites and thoughtful features ensure a relaxing and productive stay in Annapolis.

Where to stay near Chester

Chester, Maryland, is a delightful destination for outdoor enthusiasts and families seeking a beach vacation. With its sunny weather and friendly atmosphere, you'll find plenty of attractions to explore. Nearby, the charming Cheshire countryside offers a relaxing escape, while local shopping complexes cater to all your needs. Whether you're looking for historical sites or family-friendly activities, Chester and its surroundings promise a memorable experience for every traveller.

  • Annapolis: Situated 17.7km from Chester, Annapolis is a charming city that offers a blend of historical significance and modern attractions. Known for its vibrant waterfront, it draws visitors year-round, with peak times in May, July, and October. Families and outdoor enthusiasts flock here to enjoy educational sites, numerous shopping centres, and scenic lakeside views. Notable landmarks include the United States Naval Academy and the beautiful Sandy Point State Park, where you can bask on the beach or stroll along picturesque trails.
  • Stevensville: Just 1.6km away from Chester, Stevensville is a delightful town known for its picturesque scenery and outdoor activities. Visitors often come in April and June to July, attracted by its family-friendly atmosphere and recreational areas. The vibrant boardwalk offers stunning views and a taste of local culture, while nearby attractions like the picturesque beaches and the Chesapeake Bay Environmental Center provide ample opportunities for exploration and relaxation. Whether you're cycling along the shore or enjoying a picnic in a national state park, Stevensville is a must-visit.
  • Grasonville: Located 6.4km from Chester, Grasonville welcomes visitors with its appealing combination of outdoor adventures and city-like amenities. Peak travel occurs from June to August, making it an ideal summer getaway for families. The town features a lively boardwalk and recreational areas perfect for picnics and play. Highlights include the nearby beaches and the stunning scenery of the national state park, where you can hike or simply unwind. Grasonville is a great base for those looking to explore the natural beauty of Maryland while enjoying its local charm.

Things to do near Chester

Chester, Maryland, is ideal for a family beach getaway, offering a range of outdoor activities. Visitors can enjoy the scenic recreational areas and engage in a round of golf at the local courses. Whether you're looking to relax by the water or get active in nature, Chester promises a delightful experience for all ages.

Shopping

For gifts and souvenirs, visit Paul Reed Smith Guitars, only 3.2km from Chester. If you're up for a drive, check out Queenstown Premium Outlets, 11.3km away, or the Annapolis Harbour Center, located 22.5km from Chester, both offering a mix of shopping and entertainment.

Recreation

Navy-Marine Corps Memorial Stadium, 19.3km from Chester, offers an energetic atmosphere for sports enthusiasts. Nearby, Queenstown Harbor Golf Club, 11.3km away, provides a picturesque outdoor golfing experience. For a cultural touch, the Ballet Theater of Maryland, also 19.3km from Chester, showcases captivating performances that evoke romance and creativity.

Adventure

Experience the thrill of sailing at Annapolis Sailing School, located 16.1km from Chester, where you can embrace the outdoor vibes on the water. For tennis enthusiasts, Tose Family Tennis Center offers a vibrant adventure atmosphere, also 16.1km away. Don’t miss the fun at Chesapeake Beach Water Park, 38.6km away, perfect for family adventures.

Nightlife

Experience the vibrant nightlife in Chester by catching a show at the Avalon Theatre, just 29.0km away, or enjoy family fun at Annapolis Bowl, located 22.5km away. Don’t miss The Colonial Players, 17.7km from Chester, for an entertaining night filled with culture and romance.

Booking tips and Expedia advantages for Chester

For a budget-friendly trip to Chester, Maryland, consider visiting between December and February when prices are lower. Booking your stay on a Monday can also save you money compared to Saturday. Use Expedia to refine your accommodation search and look for eco-friendly options. Combining your hotel, flights, and activities into a package can lead to significant savings. Don't forget to explore free local activities and utilise public transport for cost-effective travel around the area.

  • The most and least expensive months on average to stay in a hotel: The cheapest months to stay in Chester are December to February, where the prices are slightly lower. This is in comparison to May and September to October, where prices are slightly higher.
  • The most and least expensive days on average to stay in a hotel: The least expensive day to stay in Chester is Monday. The most expensive day to stay in Chester is Saturday.
  • Find cheap hotels on Expedia: Utilise Expedia’s search tool to refine your preferences, such as your budget, preferred location, and type of accommodation you desire. For instance, selecting the Eco-certified filter will showcase sustainable and eco-friendly hotels that are currently available. To find the best bargains, simply sort the price filter from lowest to highest.
  • Consider bundling your trip: You can save some dollars by combining your Chester hotel reservation with your flights and activities through an Expedia package.

Find the best attractions near Chester

Chester, Maryland, is perfect for outdoor and family beach holidays, offering a mix of urban parks, picturesque beaches, and national parks. Visitors can explore top attractions like the Chester Zoo, Chester Cathedral, and the Chester Racecourse, as well as delve into the town's rich history. This charming locale provides an array of experiences that cater to both adventure seekers and culture lovers alike.

  • U.S. Naval Academy: Located 17.7km from Chester, the U.S. Naval Academy offers a deep dive into American naval history. Explore its stunning architecture and picturesque grounds while enjoying the serene atmosphere that reflects the pride and tradition of the U.S. Navy.
  • Sandy Point State Park: Just 11.3km from Chester, this national park is a haven for outdoor enthusiasts. Experience a range of adventures, from hiking and biking to picnicking amidst beautiful scenery, all while soaking in the natural beauty of the Chesapeake Bay.
  • Sandy Point Beach: Situated 9.7km away, Sandy Point Beach is perfect for a classic beach day. Relax on the sandy shores, swim in the refreshing waters, or indulge in beach activities, making it a great spot to unwind and soak up the sun.

Best time to go to Chester

The best time to visit Chester can depend on the weather and when visitor numbers rise and fall. The hottest average temperature in Chester falls in July, when visitor numbers are slightly high and weather is mostly sunny with light rain. The coolest average temperature in Chester falls in January, visitor numbers are slightly low and weather is mostly sunny with light rain.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January35.1°F (1.7°C)Light RainMostly SunnySlightly LowSlightly Low
February37.4°F (3.0°C)Light RainMostly SunnySlightly LowSlightly Low
March43.9°F (6.6°C)Light RainMostly SunnyAverageAverage
April54.1°F (12.3°C)Light RainMostly SunnyAverageAverage
May63.5°F (17.5°C)Light RainMostly SunnySlightly HighSlightly High
June72.3°F (22.4°C)Light RainMostly SunnyAverageAverage
July77.9°F (25.5°C)Light RainMostly SunnySlightly HighAverage
August76.3°F (24.6°C)Light RainMostly SunnySlightly HighAverage
September70.5°F (21.4°C)Light RainMostly SunnyAverageSlightly High
October60.3°F (15.7°C)Light RainMostly SunnyAverageSlightly High
November48.7°F (9.3°C)Light RainMostly SunnyAverageAverage
December41.0°F (5.0°C)Light RainMostly SunnySlightly LowSlightly Low

The nearest major airports for your trip to Chester

To reach Chester, Maryland, you can fly into three major airports. Washington, DC (DCA-Ronald Reagan Washington National) is approximately 66.0km away, with luxurious options like the 5-star Salamander Washington DC and InterContinental Washington D.C. - The Wharf, both just 3.2km from the airport. Baltimore, MD (BWI-Baltimore Washington Intl. Thurgood Marshall) is closer at 40.2km, offering excellent stays like the Four Seasons Hotel Baltimore and Sagamore Pendry Baltimore, which provide airport shuttle services. Additionally, Baltimore, MD (MTN-Martin State) is also 40.2km away, with hotels like Canopy by Hilton Baltimore Harbor Point and Hyatt Place Baltimore Inner Harbor, ensuring comfortable access to your travels.