Chestertown holiday homes

Why visit Chestertown

• Scenic Riverwalk: Enjoy leisurely strolls along Chestertown's picturesque Riverwalk, offering beautiful views of the water and surrounding landscape.
• Historic Charm: Wander through the historic streets, soaking in the rich heritage and unique architecture of this charming town.
• Family-Friendly Atmosphere: Chestertown is perfect for families, with vibrant community events and outdoor spaces for all ages to enjoy.
• Lush Parks: Explore the city's parks, providing ample opportunities for relaxation and outdoor activities amidst nature.
• Welcoming Community: Experience the warm hospitality of the local community, making your visit memorable and enjoyable.

Top attractions in and around Chestertown

Chestertown, Maryland, offers a charming blend of outdoor experiences and scenic beauty, making it an ideal destination for travellers seeking adventure. Explore its picturesque parks and enjoy leisurely strolls along the Chestertown Riverwalk. Families can revel in the vibrant atmosphere, while beach enthusiasts can appreciate the nearby waterfront. Whether you’re driving through or wandering on foot, Chestertown promises a delightful getaway filled with natural attractions and local charm.

• Mount Harmon Plantation: A historic house 21km from Chestertown, offering an authentic cultural experience steeped in history.
• Historical Society of Kent County Maryland: Situated within Chestertown, this history museum presents local heritage and artefacts that reveal the region’s past.
• Wilmer Park: Located in Chestertown, this urban park provides a family-friendly urban oasis with lush outdoor spaces and vibrant city energy.

Things to do recommended for couples

Discover Chestertown’s charm with scenic waterfront strolls and intimate dining experiences. Enjoy exploring historic streets and local art galleries, creating memories to cherish on your romantic getaway.

Things to do recommended for families

Families visiting Chestertown can explore charming local shops and enjoy waterfront picnics. They can also experience interactive exhibitions at local museums, offering engaging activities for kids and a taste of authentic American small-town life.

Things to do recommended for groups

Explore the historic streets of Chestertown, visit the local farmers' market for fresh produce, and enjoy a group kayak tour on the Chester River. Don't miss the chance to sample local craft beers at nearby breweries for a true taste of Maryland.

What do I need to keep in mind when booking a vacation in Chestertown

When planning your trip, whether you're travelling with a group, enjoying a family getaway, bringing along your pets, or seeking extended stays, it’s important to filter your options based on your key priorities. Here are some helpful Vrbo booking tips to consider.

• Traveling to Chestertown with a group: Think about how many bedrooms you'll require, along with features like a complete kitchen or outdoor areas for group gatherings. The good news is that you can easily filter for all of these options, and plenty more, on Vrbo.
• Traveling to Chestertown with young kids: Travelling with young children can present its challenges. It's important to prioritise their comfort and safety, alongside ensuring access to suitable amenities like a private swimming pool. Additionally, considering your closeness to family-friendly attractions can enhance your experience.
• Taking your pets with you to Chestertown: For many, a family getaway isn’t truly complete without their furry companion. If that resonates with you, take a look at Vrbo properties that welcome pets. Many of these pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone feels comfortable and at home.
• Planning for a long term stay visiting Chestertown: If you’re in search of holiday rentals that offer great deals for stays of a month or more, you’ve come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don’t forget to include options like a parking space, a well-equipped kitchen, or even a private pool in your search criteria.

Where to stay in and around Chestertown

Chestertown offers a charming blend of family-friendly history and scenic waterfront views. Enjoy leisurely strolls along the historic streets and take in the waterfront ambiance. With plenty of cosy neighbourhoods offering a budget-friendly and relaxed vibe, the city is perfect for exploring its rich heritage and lush outdoor attractions. Discover the unique experience of historic Chestertown while enjoying the welcoming local community.

• Queenstown: Queenstown is a vibrant city located 26km from Chestertown, offering an engaging blend of outdoor and family-friendly activities. The area is renowned for its scenic landscapes, inviting travellers to enjoy a day at the golf course or a leisurely visit to the shopping centre. With natural attractions such as the bay, beach, and park nearby, visitors can revel in the picturesque surroundings and embrace the local charm that reflects the quintessential outdoor experience.
• Worton: Worton is a welcoming city positioned 6km from Chestertown, perfect for those seeking a refreshing outdoor escape. The city's proximity to the beach, bay, and lake provides ample opportunities for soaking in the coastal scenery and enjoying recreational activities. With access to outdoor venues and educational spots, Worton offers a refreshing mix of nature and community engagement, ideal for a relaxed day exploring the local environment.
• Georgetown: Georgetown is a quaint village nestled in the Chestertown area, celebrated for its blend of outdoor, romantic, and entertainment-themed experiences. Visitors can explore local attractions such as the beach, marina, and national state park, which offer a diverse range of outdoor activities. The presence of a recreation centre, educational venues, and hiking trails further enhances the village's appeal, creating a well-rounded destination for those in search of both adventure and tranquillity.

Best time to go to Chestertown

If you're planning a trip to Chestertown, it's a good idea to check both the weather and property rates. The warmest month is July.

Calendar Month	Temperature	Precipitation	Cloudiness	Occupancy	Pricing
January	34.2°F (1.2°C)	Light Rain	Mostly Sunny	Slightly Low
February	36.9°F (2.7°C)	Light Rain	Mostly Sunny	Average
March	43.7°F (6.5°C)	Light Rain	Mostly Sunny	Average
April	54.3°F (12.4°C)	Light Rain	Mostly Sunny	Slightly High
May	63.7°F (17.6°C)	Light Rain	Mostly Sunny	Average
June	72.1°F (22.3°C)	Light Rain	Mostly Sunny	Slightly High
July	77.4°F (25.2°C)	Light Rain	Mostly Sunny	Slightly High
August	75.6°F (24.2°C)	Light Rain	Mostly Sunny	Average
September	69.4°F (20.8°C)	Light Rain	Mostly Sunny	Average
October	59.2°F (15.1°C)	Light Rain	Mostly Sunny	Average
November	47.3°F (8.5°C)	Light Rain	Mostly Sunny	Slightly Low
December	40.1°F (4.5°C)	Light Rain	Mostly Sunny	Slightly Low

Booking with Vrbo is simple

Looking to trim costs on your next adventure? Keeping your travel dates flexible might just be your ticket, as rates can fluctuate. You could also unlock considerable savings by opting for a longer stay. To discover a Vrbo property that suits your budget, simply use our filters to sort by price, location, and holiday rental type.

Vrbo Trips: Planning made easy

Vrbo’s Trip Board offers a handy space to start planning new trips, continue planning where you last paused, or review and organise your travel plans. Here, you can find properties you’ve either saved or booked, neatly sorted into Potential, Upcoming, or Current Trips. To begin using Trip Boards, visit: https://www.bookabach.co.nz/trips.

**Based on Vrbo properties bookings.

Why people love visiting cosy Chestertown

Take a holiday to Chestertown and enjoy the area's festivals, history and art galleries. This city's sporting events, university setting and boating draw many visitors. Are you looking for specific amenities for your getaway? Many of our holiday rentals feature full kitchens and laundry facilities.

Activities and attractions in Chestertown

Do you want to discover top things to see and do while you're in town? Venture out of your cosy holiday rental and experience everything that makes Chestertown a one-of-a-kind holiday spot. These are some of the major attractions to see, all within 30 miles (48.2 km) of the city centre:

• Crow Farm and Vineyard (10.2 mi / 16.4 km)
• Queenstown Harbor Golf (16.7 mi / 26.9 km)
• Paul Reed Smith Guitars (20.7 mi / 33.3 km)
• Bay Hills Golf Club (25 mi / 40.2 km)
• Rocky Point Golf Course (18.6 mi / 30 km)
• Cassinelli Winery and Vineyards (7.1 mi / 11.3 km)

Exploring the natural landscape of Chestertown

Whether you're looking for fun outdoor activities or just want to appreciate the scenery, Chestertown is a great place to get out in nature. Here are a few of the area's most stunning natural features, all within 30 miles (48.2 km) of the city centre:

• Betterton Beach (10.5 mi / 16.9 km)
• Eastern Neck National Wildlife Refuge (15.4 mi / 24.8 km)
• Miami Beach (17.2 mi / 27.7 km)
• Rocky Point Park and Beach (18.1 mi / 29.2 km)
• North East Beach Area (19.4 mi / 31.3 km)
• Chesapeake Bay Environmental Center (20.6 mi / 33.1 km)

Transport options to and around Chestertown

The nearest airport is in Baltimore, MD (MTN-Martin State), located 20.3 mi (32.7 km) from the city centre. If you can't find a flight that works for your travel itinerary, you could also fly into Easton, MD (ESN-Easton - Newnam), which is 28.2 mi (45.3 km) away.