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21 Aug - 22 Aug
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Our top choices for Chester hotels

1. Laurel Grove Inn on the South

Laurel Grove Inn on the South
Annapolis
United States
Ruth
AU$288
includes taxes & fees
23 Aug - 24 Aug
Laurel Grove Inn on the South

2. Holiday Inn Express Annapolis East-Kent Island by IHG

Holiday Inn Express Annapolis East-Kent Island by IHG
Grasonville
United States
Jackie
AU$198
includes taxes & fees
7 Sept - 8 Sept
Holiday Inn Express Annapolis East-Kent Island by IHG

3. Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina
Grasonville
United States
Karen
AU$260
includes taxes & fees
8 Sept - 9 Sept
Hyatt Place Kent Narrows & Marina

4. Hilton Garden Inn Kent Island Marina

Hilton Garden Inn Kent Island Marina
Grasonville
United States
roney
AU$229
includes taxes & fees
30 Aug - 31 Aug
Hilton Garden Inn Kent Island Marina

5. Best Western Kent Narrows Inn

Best Western Kent Narrows Inn
Grasonville
United States
chanel
AU$198
includes taxes & fees
27 Aug - 28 Aug
Best Western Kent Narrows Inn

6. Quality Inn Grasonville near Kent Island

Quality Inn Grasonville near Kent Island
Grasonville
United States
Faezeh
AU$157
includes taxes & fees
10 Sept - 11 Sept
Quality Inn Grasonville near Kent Island

7. Kent Island Resort

Kent Island Resort
Stevensville
United States
Leigh
AU$288
includes taxes & fees
10 Sept - 11 Sept
Kent Island Resort

8. The Inn at Chesapeake Bay Beach Club

The Inn at Chesapeake Bay Beach Club
Stevensville
United Kingdom
Jamie
AU$372
includes taxes & fees
31 Aug - 1 Sept
The Inn at Chesapeake Bay Beach Club

9. DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis
Annapolis
United States
eliana
AU$156
includes taxes & fees
30 Aug - 31 Aug
DoubleTree by Hilton Hotel Annapolis

10. Historic Inns of Annapolis

Historic Inns of Annapolis
Historic District
United States
Stephanie
AU$195
includes taxes & fees
27 Aug - 28 Aug
Historic Inns of Annapolis

11. Fairfield Inn & Suites By Marriott Annapolis

Fairfield Inn & Suites By Marriott Annapolis
Annapolis
United States
Tola
AU$189
includes taxes & fees
25 Aug - 26 Aug
Fairfield Inn & Suites By Marriott Annapolis

12. Holiday Inn Express & Suites Annapolis by IHG

Holiday Inn Express & Suites Annapolis by IHG
Annapolis
United States
Frank
AU$162
includes taxes & fees
24 Aug - 25 Aug
Holiday Inn Express & Suites Annapolis by IHG

13. St Michaels Inn

St Michaels Inn
St. Michaels
United States
Karen
AU$128
includes taxes & fees
31 Aug - 1 Sept
St Michaels Inn

14. SpringHill Suites by Marriott Annapolis

SpringHill Suites by Marriott Annapolis
Annapolis
United States
Joshua
AU$190
includes taxes & fees
16 Sept - 17 Sept
SpringHill Suites by Marriott Annapolis

15. Best Western Annapolis

Best Western Annapolis
Annapolis
United States
George
AU$128
includes taxes & fees
23 Aug - 24 Aug
Best Western Annapolis

16. Best Western Plus Easton Inn & Suites

Best Western Plus Easton Inn & Suites
Easton
United States
Margaret
AU$215
includes taxes & fees
26 Aug - 27 Aug
Best Western Plus Easton Inn & Suites

17. Country Inn & Suites by Radisson, Annapolis, MD

Country Inn & Suites by Radisson, Annapolis, MD
Annapolis
United States
Leslie
AU$152
includes taxes & fees
13 Sept - 14 Sept
Country Inn & Suites by Radisson, Annapolis, MD

18. Quality Inn

Quality Inn
Easton
United States
Karen
AU$175
includes taxes & fees
23 Aug - 24 Aug
Quality Inn

19. Hilton Garden Inn Annapolis Downtown

Hilton Garden Inn Annapolis Downtown
Annapolis
United States
Nelson
AU$164
includes taxes & fees
30 Aug - 31 Aug
Hilton Garden Inn Annapolis Downtown

20. Courtyard by Marriott Annapolis

Courtyard by Marriott Annapolis
Annapolis
United States
Phyllis
AU$147
includes taxes & fees
30 Aug - 31 Aug
Courtyard by Marriott Annapolis
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Stay near popular Chester attractions

Chesapeake Exploration Center

Learn about the events happening in 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
A boat docked at a pier during twilight with a city skyline in the background.
Photo by Patricia Knorr

Top Chester Hotel Reviews

Recent Reviews in Chester

Crowne Plaza Annapolis by IHG

Crowne Plaza Annapolis by IHG

10/10 Excellent
"We really wished the pool was opened"
India 2-night trip
Posted 5 hours ago
Crowne Plaza Annapolis by IHG
Holiday Inn Express Annapolis East-Kent Island by IHG

Holiday Inn Express Annapolis East-Kent Island by IHG

10/10 Excellent
"Spent one night. Friendly staff. Plenty of space and we had a view of the water."
Stacie 1-night trip
Posted 7 hours ago
Holiday Inn Express Annapolis East-Kent Island by IHG
Annapolis Waterfront Hotel, Autograph Collection

Annapolis Waterfront Hotel, Autograph Collection

10/10 Excellent
"Top notch staff from the front desk, housekeeping and valet. My only real complaint was the early AM construction in the hallway. But all the workers were friendly and courteous to me passing by to get to the elevator."
Erich 1-night trip
Posted 8 hours ago
Annapolis Waterfront Hotel, Autograph Collection
St Michaels Inn

St Michaels Inn

8/10 Good
"Property was a bit outdated but hopefully the construction will give it the update it needs."
David 2-night trip
Posted 9 hours ago
St Michaels Inn
Historic Inns of Annapolis

Historic Inns of Annapolis

10/10 Excellent
"A great property in a great location . The people we interacted with were friendly and helpful. I highly recommend Historic Inn in Annapolis"
Kenneth 1-night trip
Posted 11 hours ago
Historic Inns of Annapolis
Holiday Inn Express & Suites Annapolis by IHG

Holiday Inn Express & Suites Annapolis by IHG

8/10 Good
"Reasonable value for the money"
Frank 1-night trip
Posted 18 hours ago
Holiday Inn Express & Suites Annapolis by IHG
Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina

10/10 Excellent
"Property was well maintained and clean. Room was spacious and with a nice view. Parking is somewhat limited. Location is also central to area,attractions."
Michael 3-night trip
Posted 1 day ago
Hyatt Place Kent Narrows & Marina
DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis

10/10 Excellent
"Clean and comfortable room, helpful staff and great room service!"
Catherine 1-night trip
Posted 1 day ago
DoubleTree by Hilton Hotel Annapolis
Courtyard by Marriott Annapolis

Courtyard by Marriott Annapolis

10/10 Excellent
"Perfectly decent hotel for overnight stay during roadtrip."
Phyllis 1-night trip
Posted 2 days ago
Courtyard by Marriott Annapolis

More cheap accommodation in Chester

St Michaels Inn

St Michaels Inn

1228 S Talbot Street St. Michaels MD
AU$128
31 Aug - 1 Sept
includes taxes & fees
8.2/10 Very good! (1,006 reviews)
St Michaels Inn
Best Western Annapolis

Best Western Annapolis

2520 Riva Rd Annapolis MD
AU$128
23 Aug - 24 Aug
includes taxes & fees
7.8/10 Good! (1,008 reviews)
Best Western Annapolis
Hampton Inn & Suites Annapolis

Hampton Inn & Suites Annapolis

124 Womack Dr Annapolis MD
AU$157
16 Sept - 17 Sept
includes taxes & fees
Hampton Inn & Suites Annapolis
Holiday Inn Express & Suites Annapolis by IHG

Holiday Inn Express & Suites Annapolis by IHG

2451 Riva Rd Annapolis MD
AU$162
24 Aug - 25 Aug
includes taxes & fees
8.4/10 Very good! (1,009 reviews)
Holiday Inn Express & Suites Annapolis by IHG
Holiday Inn Express Annapolis East-Kent Island by IHG

Holiday Inn Express Annapolis East-Kent Island by IHG

1020 Kent Narrows Rd Grasonville MD
AU$198
7 Sept - 8 Sept
includes taxes & fees
9.2/10 Wonderful! (1,008 reviews)
Holiday Inn Express Annapolis East-Kent Island by IHG
Best Western Kent Narrows Inn

Best Western Kent Narrows Inn

3101 Main Street Grasonville MD
AU$198
27 Aug - 28 Aug
includes taxes & fees
8/10 Very good! (1,001 reviews)
Best Western Kent Narrows Inn

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.

Frequently asked questions

What is the best area to stay in Chester?
For most visitors, the best area to stay in Chester is along Kent Narrows, which offers convenient access to the water and local amenities.This area is the main hub for visitors, with many hotels, restaurants, and marinas lining the waterfront. It's located directly on the Kent Narrows waterway, connecting the Chester River to the Chesapeake Bay. You'll find a mix of seafood restaurants, shops, and places to enjoy water activities. Most establishments are easily accessible from Kent Narrows Road.Couples looking for a relaxing getaway will appreciate the waterfront hotels in Kent Narrows. Many offer rooms with water views and balconies, providing a pleasant setting for unwinding. You can enjoy strolls along the docks, dine at restaurants with outdoor seating overlooking the water, and easily access boat tours or fishing charters.For travellers looking for a convenient base to explore the wider Eastern Shore, staying in Kent Narrows is also excellent.
When is the best time to go to Chester?
The best time to go to Chester, Maryland, is during the spring (late April to early June) and autumn (September to October) months. These periods offer pleasant weather ideal for exploring the area.Spring brings comfortable temperatures, typically ranging from 15°C to 25°C, and the landscape is lush with new growth. It's a great time for outdoor activities like cycling along the Cross Island Trail or visiting the local wineries. The breezes off the Chesapeake Bay are particularly refreshing.Autumn also provides agreeable weather, with temperatures usually between 10°C and 20°C, and the changing foliage creates a scenic backdrop. This season is superb for enjoying seafood festivals or simply taking a leisurely drive across the Kent Narrows Bridge to admire the views.
Can I cancel my hotel reservation on Expedia?
You can cancel your hotel reservation on Expedia, though it depends on the cancellation policy of your booking. Most bookings are refundable if cancelled within 24-48 hours of the scheduled arrival. Be sure to check your booking confirmation for the exact cancellation policy. If free cancellation is available, you can cancel directly through your Expedia account by logging in, going to "My Trips", and selecting your reservation. To find flexible deals, filter your search by "Fully refundable property" for hotels in Chester.
How can I save on a hotel booking in Chester with Expedia?
One Key™—Expedia's free travel rewards program—gives you instant access to discounts with Member Prices on Chester hotels. Plus, you'll earn OneKeyCash™* on eligible bookings to use on future trips. Booking an Expedia hotel and flight package is another great way to save, where bundling can result in significant savings. *Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia and other participating brands.
How much is the nightly rate for a hotel in Chester?
Prices for hotels in Chester often vary, but you can find a great deal from AU$128 on Expedia. All sorts of factors affect price, such as the time of year or the days of the week you choose for your stay. Find the best deals by being flexible with your dates, and sort search results by "Price: low to high" for our cheapest rates.

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