Chester Holidays

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Your Chester Holiday

When a city getaway is calling, answer it with a holiday package to Chester. The neighbourhood of Kent Narrows, which is good for cycling, views and nature, makes a great base for your adventures. You'll want to do a little exploring during your trip to Chester. Drop by popular attractions like Chesapeake Bay Environmental Centre, Eastern Neck National Wildlife Refuge and Matapeake State Park. Check out Expedia's extensive range of travel options and start planning your perfect holiday to Chester today.

Chester Holiday

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.

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

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.

Chester Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Baltimore Washington Intl. Thurgood Marshall Airport (BWI)
Population
4,200
Max Temp Winter
7ºC
Max Temp Summer
27ºC
Top Sights
Sandy Point State Park, Sandy Point Beach and Matapeake State Park

Our pick of the best Chester Hotel Deals

Historic Inns of Annapolis

Historic Inns of Annapolis

3.5 out of 5
58 State Circle, Annapolis, MD
Fully refundableReserve now, pay when you stay
8.8/10 Excellent! (1,866 reviews)
All was very good except: no soap at sink in bathroom and none could be “found.” There was a coffee pot that had to be replaced with one that could work with the type coffee pods provided. Promptly replaced, but how could housekeeping have an outdated coffee maker for older-type coffee filter ...

Reviewed on 28 Oct 2025

Historic Inns of Annapolis
Country Inn & Suites by Radisson, Annapolis, MD

Country Inn & Suites by Radisson, Annapolis, MD

3 out of 5
2600 Housley Road, Annapolis, MD
Fully refundable
The price is AU$169 per night from 9 Nov to 10 Nov
AU$169
9 Nov - 10 Nov
includes taxes & fees
8.8/10 Excellent! (1,012 reviews)
Country Inn and Suites, Annapolis MD
The breakfast could be better. The eggs did not taste like real eggs. Maybe the food was just not cooked right. I was pleased with it. I had to clean the hot tub before we used it.

Reviewed on 27 Oct 2025

Country Inn & Suites by Radisson, Annapolis, MD
Sonesta ES Suites Annapolis

Sonesta ES Suites Annapolis

3 out of 5
170 Admiral Cochrane Dr, Edgewater, MD
Fully refundableReserve now, pay when you stay
The price is AU$148 per night from 16 Nov to 17 Nov
AU$148
16 Nov - 17 Nov
includes taxes & fees
8.8/10 Excellent! (930 reviews)
Room was very clean.

Reviewed on 26 Oct 2025

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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