Photo by Patricia Knorr

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Top hotels and accommodation in Chester

Holiday Inn Express Annapolis East-Kent Island by IHG

2.5 star property
9.2 out of 10, Wonderful, (878)
"Great stay beautiful view"
The price is AU$246
includes taxes & fees
17 Aug - 18 Aug
Holiday Inn Express Annapolis East-Kent Island by IHG

Hyatt Place Kent Narrows & Marina

3.0 star property
9.4 out of 10, Exceptional, (601)
"Great place to stay. "
The price is AU$275
includes taxes & fees
11 Aug - 12 Aug
Hyatt Place Kent Narrows & Marina

Hilton Garden Inn Kent Island Marina

3.0 star property
9.0 out of 10, Wonderful, (971)
"Friendly staff, nice environment"
The price is AU$284
includes taxes & fees
1 Sept - 2 Sept
Hilton Garden Inn Kent Island Marina

Hilton Garden Inn Annapolis

3.0 star property
8.2 out of 10, Very good, (1001)
"Great staff! Super clean."
The price is AU$161
includes taxes & fees
5 Aug - 6 Aug
Hilton Garden Inn Annapolis

The Westin Annapolis

4.0 star property
8.6 out of 10, Excellent, (1003)
"The Hotel was very clean and convenient to everything that we wanted to do!!!!"
The price is AU$281
includes taxes & fees
24 Aug - 25 Aug
The Westin Annapolis

Courtyard by Marriott Annapolis

3.0 star property
8.6 out of 10, Excellent, (1002)
"Great place and great staff "
The price is AU$177
includes taxes & fees
17 Aug - 18 Aug
Courtyard by Marriott Annapolis

Historic Inns of Annapolis

3.5 star property
9.0 out of 10, Wonderful, (1811)
"Loved the hotel-great location "
Historic Inns of Annapolis

Annapolis Waterfront Hotel, Autograph Collection

4.0 star property
8.8 out of 10, Excellent, (848)
"We were pleased with the staff, room and the view. We were disappointed that there was no restaurant or bar on the property as the description led us to believe."
The price is AU$389
includes taxes & fees
17 Aug - 18 Aug
Annapolis Waterfront Hotel, Autograph Collection

Hampton Inn & Suites Annapolis

2.5 star property
8.2 out of 10, Very good, (1002)
"Very nice stay. Front desk staff was friendly and the pool is a great bonus."
The price is AU$183
includes taxes & fees
17 Aug - 18 Aug
Hampton Inn & Suites Annapolis

The Inn at Chesapeake Bay Beach Club

4.0 star property
9.4 out of 10, Exceptional, (404)
"Staff was very polite and friendly. "
The price is AU$410
includes taxes & fees
20 Aug - 21 Aug
The Inn at Chesapeake Bay Beach Club

Wylder Tilghman Island

2.0 star property
8.6 out of 10, Excellent, (56)
"Good service and good options to enjoy the stays. "
The price is AU$361
includes taxes & fees
18 Aug - 19 Aug
Wylder Tilghman Island

Kent Island Resort

3.5 star property
9.2 out of 10, Wonderful, (106)
"Hotel was great and peaceful. This hotel was water front. Nice surroundings!! I enjoyed to stay here."
The price is AU$351
includes taxes & fees
1 Sept - 2 Sept
Kent Island Resort

DoubleTree by Hilton Hotel Annapolis

4.0 star property
8.6 out of 10, Excellent, (1002)
"Excellent hospitable staff made the stay even better!"
The price is AU$176
includes taxes & fees
17 Aug - 18 Aug
DoubleTree by Hilton Hotel Annapolis

SpringHill Suites by Marriott Annapolis

3.0 star property
9.0 out of 10, Wonderful, (1002)
"Property was clean, newer hotel and convenient location."
The price is AU$179
includes taxes & fees
17 Aug - 18 Aug
SpringHill Suites by Marriott Annapolis

Country Inn & Suites by Radisson, Annapolis, MD

3.0 star property
9.0 out of 10, Wonderful, (1002)
"Great location , perfect for my family stay."
The price is AU$171
includes taxes & fees
17 Aug - 18 Aug
Country Inn & Suites by Radisson, Annapolis, MD

Holiday Inn Express & Suites Annapolis by IHG

2.5 star property
8.2 out of 10, Very good, (1002)
"Bed was very comfortable "
The price is AU$165
includes taxes & fees
3 Aug - 4 Aug
Holiday Inn Express & Suites Annapolis by IHG

Sandaway Suites & Beach

3.0 star property
9.4 out of 10, Exceptional, (143)
"It was such a beautiful place to stay at!! We only spent one night but definitely can see myself coming back with my family here! The view is to DIE for too!"
The price is AU$489
includes taxes & fees
21 Aug - 22 Aug
Sandaway Suites & Beach

Crowne Plaza Annapolis by IHG

3.5 star property
8.8 out of 10, Excellent, (1001)
"Very clean and friendly staff. Best mattress and pillows have had in hotel."
The price is AU$172
includes taxes & fees
3 Aug - 4 Aug
Crowne Plaza Annapolis by IHG

Sonesta ES Suites Annapolis

3.0 star property
8.8 out of 10, Excellent, (847)
"Great room for a great price... Very friendly staff, too."
The price is AU$182
includes taxes & fees
3 Aug - 4 Aug
Sonesta ES Suites Annapolis

Hilton Garden Inn Annapolis Downtown

3.0 star property
8.6 out of 10, Excellent, (1010)
"Really nice place to stay and enjoy Annapolis "
The price is AU$180
includes taxes & fees
1 Sept - 2 Sept
Hilton Garden Inn Annapolis Downtown
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!

Photo by Patricia Knorr
Open Photo by Patricia Knorr

Top Chester Hotel Reviews

Find out more about 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.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

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.

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 Graduate by Hilton Annapolis and DoubleTree by Hilton Hotel Annapolis. See all available top hotels, or vacation rentals in Chester.

What are some of the best holiday rentals that Chester has to offer?

Directly Across from USNA Gate One & Steps from the Waterfront and Main Street! : This holiday home rental outside of Chester is located in the city centre, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a selection of games. 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 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: Features buffet, an indoor pool and free self parking. Best Western Annapolis and SpringHill Suites by Marriott Annapolis 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 16 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 Eastern Neck National Wildlife Refuge and Sandy Point Beach 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.