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Our top choices for Chester hotels

Econo Lodge Easton Route 50

Econo Lodge Easton Route 50
2.5 star property
Easton
6.6 out of 10, (389 reviews)
"The parking was good but l didn't do breakfast "
United States
Tammy
The price is AU$129
includes taxes & fees
12 Apr - 13 Apr
Econo Lodge Easton Route 50

Hampton Inn Easton

Hampton Inn Easton
2.5 star property
Easton
9.0 out of 10, Wonderful, (561 reviews)
"all excellent with kudos to staff and the breakfast cook."
United States
JOSEPH
The price is AU$229
includes taxes & fees
9 Apr - 10 Apr
Hampton Inn Easton

Quality Inn

Quality Inn
2.5 star property
Easton
7.6 out of 10, Good, (854 reviews)
"Room was clean and staff was friendly and helpful."
United States
Constantine
The price is AU$129
includes taxes & fees
13 Apr - 14 Apr
Quality Inn

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)
"Fresh breakfast with a good variety, friendly staff that gave me an upgrade, clean cozy hotel, safe well-lighted parking area"
United States
Irene
The price is AU$174
includes taxes & fees
7 Apr - 8 Apr
Best Western Plus Easton Inn & Suites

Holiday Inn Express Easton by IHG

Holiday Inn Express Easton by IHG
3.0 star property
Easton
9.0 out of 10, Wonderful, (600 reviews)
"Everything was great!"
United States
HEATHER
The price is AU$247
includes taxes & fees
7 Apr - 8 Apr
Holiday Inn Express Easton by IHG

Fairfield Inn & Suites by Marriott Easton

Fairfield Inn & Suites by Marriott Easton
3.0 star property
Easton
9.6 out of 10, Exceptional, (370 reviews)
"Staff was very frienly and courteous. There were needed gluten-free breakfast items and if something wasn’t out the staff kindly went to storage to provide it. The room was spotless. I highly recommend staying there!"
United States
Karen
The price is AU$215
includes taxes & fees
12 Apr - 13 Apr
Fairfield Inn & Suites by Marriott Easton

Hummingbird Inn

Hummingbird Inn
3.5 star property
Easton
10.0 out of 10, Exceptional, (89 reviews)
" Staff is super friendly. The rooms were very clean and the breakfast was wonderful."
United States
Lewis
The price is AU$472
includes taxes & fees
7 Apr - 8 Apr
Hummingbird Inn

The Tidewater Inn

The Tidewater Inn
3.0 star property
Easton
8.8 out of 10, Excellent, (864 reviews)
"The property was beautiful and we enjoyed the room, the bar and the restaurant for breakfast. It is also in a great location in a very walkable town area."
United States
Linda
The price is AU$270
includes taxes & fees
8 Apr - 9 Apr
The Tidewater Inn

Sandaway Suites & Beach

Sandaway Suites & Beach
3.0 star property
Oxford
9.4 out of 10, Exceptional, (156 reviews)
"VERY pleasant stay at Sandaway! "
United States
Gilbert
The price is AU$286
includes taxes & fees
12 Apr - 13 Apr
Sandaway Suites & Beach

The Oaks Waterfront

The Oaks Waterfront
4.0 star property
Easton
10.0 out of 10, Exceptional, (41 reviews)
"Staff, breakfast, and room were all superb!"
United States
Jeffrey
The price is AU$702
includes taxes & fees
7 Apr - 8 Apr
The Oaks Waterfront

St Michaels Inn

St Michaels Inn
2.5 star property
St. Michaels
8.2 out of 10, Very good, (1,002 reviews)
" Great place,great location, was in town for St Michael Chocolate fest "
United States
Katherine
The price is AU$199
includes taxes & fees
8 Apr - 9 Apr
St Michaels Inn

Inn at Perry Cabin

Inn at Perry Cabin
5.0 star property
Downtown St. Michaels
9.6 out of 10, Exceptional, (379 reviews)
"everything was perfect!"
United States
John
The price is AU$912
includes taxes & fees
23 Apr - 24 Apr
Inn at Perry Cabin

The Wildset

The Wildset
2.5 star property
Downtown St. Michaels
9.8 out of 10, Exceptional, (431 reviews)
"Best HOTEL EVER!!!"
United States
Ama
The price is AU$381
includes taxes & fees
7 Apr - 8 Apr
The Wildset

Parsonage Inn

Parsonage Inn
3.5 star property
Downtown St. Michaels
9.2 out of 10, Wonderful, (133 reviews)
"Hosts were wonderful, breakfast was delicious, everything was walkable "
United States
Nathaly
The price is AU$399
includes taxes & fees
7 Apr - 8 Apr
Parsonage Inn

George Brooks House B&B

George Brooks House B&B
3.0 star property
St. Michaels
8.8 out of 10, Excellent, (70 reviews)
"A beautiful renovated historical house with charm, clean rooms, decorative furnishings and a wonderful hot breakfast. What we enjoyed the most was the warm hospitality of Willard, Valerie, and the other staff. Very close to downtown St. Michael’s, but just far enough away to give a nice feel of natural serenity. Great for a quick getaway from the city. We will be back. "
United States
Charles
The price is AU$271
includes taxes & fees
7 Apr - 8 Apr
George Brooks House B&B

Quality Inn Grasonville near Kent Island

Quality Inn Grasonville near Kent Island
2.5 star property
Grasonville
7.8 out of 10, Good, (887 reviews)
"Staff was nice and room was clean "
United States
Lauren
The price is AU$157
includes taxes & fees
9 Apr - 10 Apr
Quality Inn Grasonville near Kent Island

Hilton Garden Inn Kent Island Marina

Hilton Garden Inn Kent Island Marina
3.0 star property
Grasonville
9.0 out of 10, Wonderful, (1,003 reviews)
"Beautiful area"
United States
Dan
The price is AU$223
includes taxes & fees
13 Apr - 14 Apr
Hilton Garden Inn Kent Island Marina

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, (978 reviews)
"Very nice hotel, good breakfast selection, clean rooms."
United States
Linda
The price is AU$187
includes taxes & fees
20 Apr - 21 Apr
Holiday Inn Express Annapolis East-Kent Island by IHG

Best Western Kent Narrows Inn

Best Western Kent Narrows Inn
2.5 star property
Grasonville
8.0 out of 10, Very good, (1,002 reviews)
"Wonderful staff,Clean rooms and comfortable bed!!"
United States
Evette
The price is AU$160
includes taxes & fees
14 Apr - 15 Apr
Best Western Kent Narrows Inn

Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina
3.0 star property
Grasonville
9.6 out of 10, Exceptional, (734 reviews)
"Clean hotel all around. Friendly stafff and comfortable environment."
United States
Jillian
The price is AU$240
includes taxes & fees
8 Apr - 9 Apr
Hyatt Place Kent Narrows & Marina
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!

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.

Frequently asked questions

What's the best place to stay in Chester?
Located 11.2 mi (18 km) from the heart of Chester, Graduate by Hilton Annapolis is a top choice for your stay, based on our traveller data. Two other options for your stay in the area are Historic Inns of Annapolis and Crowne Plaza Annapolis by IHG. See all available top hotels, or vacation rentals in Chester.
What are some of the best holiday rentals that Chester has to offer?
Waterfront Sunset Bayview: sleeps 6: This highly rated holiday home rental in Chester is located on the waterfront, and offers a patio, air conditioning and laundry facilities to help you feel perfectly comfortable 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. 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?
Crowne Plaza Annapolis by IHG: Hotel located near U.S. Naval Academy. Offers free self parking, an indoor pool and complimentary wireless Internet access. Sonesta ES Suites Annapolis and Country Inn & Suites by Radisson, Annapolis, MD 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 10 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 Northern Chesapeake Bay, Matapeake State Park and Chesapeake Bay Environmental Center. You'll also find Love Point State Park 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.

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