Chestertown vacation rentals

Why visit Chestertown

1. Outdoor Adventures: Enjoy a variety of outdoor activities, including exploring scenic parks and beautiful beaches.
2. Rich History: Discover Chestertown's charming homes and delve into its local culture and history.
3. Waterfront Views: Take in stunning views along the waterfront while strolling through family-friendly neighborhoods.
4. Art and Culture: Experience local art galleries and cultural events just a short distance from downtown.
5. Diverse Accommodations: Choose from charming vacation rentals and cozy cottages to suit your travel needs.

Popular types of accommodation in Chestertown

Ready to explore Chestertown? The first step is finding the perfect place to stay. From charming houses and cozy cottages to modern apartments, Chestertown offers a variety of vacation rentals to suit every traveler's needs. Discover the best home rentals and unique accommodations that provide comfort and convenience during your visit. Start planning your getaway with our selection of Chestertown vacation rentals today!

• Houses: These spacious and fully-equipped homes are the top choice for families or groups seeking comfort and convenience during their stay in Chestertown.
• Cottages: Quaint and charming, cottages offer a cozy atmosphere perfect for romantic getaways or peaceful retreats.
• Apartments: Ideal for solo travelers or couples, apartments provide a home-like environment with essential amenities.
• Condos: These modern accommodations offer great amenities and often come with stunning views, perfect for a relaxing vacation.
• House Boats: Experience a unique stay on the water with houseboats, providing both adventure and comfort in Chestertown.**

Top attractions in Chestertown

Chestertown, Maryland, is ideal for outdoor enthusiasts and beach lovers alike. Visitors can explore various attractions, including beautiful beaches, scenic parks, and urban parks perfect for family outings. The area offers a blend of nature and leisure, making it a great destination for those seeking a relaxing vacation. Don't miss the chance to discover the charming homes and local culture that Chestertown has to offer.

1. Washington College: A historic institution with a charming campus, Washington College offers rich culture and vibrant student life. Explore its beautiful architecture and engage with the local academic community.
2. Rolphs Wharf Marina: This picturesque marina invites outdoor enthusiasts with its beach access and adventure opportunities. Enjoy boating, fishing, or simply relaxing by the water while soaking in the natural beauty.
3. River Arts Chestertown: An inspiring arts center fostering creativity, River Arts features local artwork and hosts community events. Immerse yourself in the vibrant arts scene and discover unique pieces from talented artists.

Things to do recommended for couples

For a romantic getaway in Chestertown, visit Cassinelli Winery and Vineyards, just 7 miles away, for a charming atmosphere. Explore Tilmon's Island Winery at 11 miles, or enjoy the scenic Crow Farm and Vineyard located 10 miles from town. Each offers delightful entertainment and a lovely vibe for couples.

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

When planning your travel, whether you're going with a group, family, pets, or seeking extended stays, it's important to prioritize your filters accordingly. Here are some helpful booking tips for Vrbo to assist you.

• Traveling to Chestertown with a group: Think about how many bedrooms you'll require, along with features like a full kitchen or outdoor areas for group gatherings. The good news is that you can easily filter for these options and many more on Vrbo.
• Traveling to Chestertown with young kids: Traveling with young kids can be quite demanding. It's important to prioritize their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, it's wise to think about how close you are to family-friendly attractions.
• Taking your pets with you to Chestertown: For many families, a vacation wouldn't be the same without their furry companions. If you relate to this, explore Vrbo listings that welcome pets. Many of these pet-friendly accommodations come equipped with feeding bowls and beds, ensuring that every member of your family feels comfortable and at home.
• Planning for a long term stay visiting Chestertown: If you're in search of vacation rentals offering special rates 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 rental options. Don't forget to include amenities like parking, a well-equipped kitchen, or a private pool in your search for the perfect getaway.

Where to stay in Chestertown

Chestertown, Maryland, offers a delightful blend of outdoor adventures and rich history. Explore family-friendly neighborhoods with charming homes while enjoying the scenic views along the waterfront. Just a short distance from downtown, you can experience local art and culture, as well as relaxing transit options. Nearby areas provide a welcoming atmosphere perfect for budget-conscious travelers and families alike, making Chestertown an ideal destination for your next vacation.

• Georgetown: Nestled within the Chestertown area, Georgetown is a charming village renowned for its outdoor adventures and romantic atmosphere. Visitors are drawn to its educational and recreational areas, perfect for families and couples alike. The local stadium and sports facility provide ample opportunities for sports enthusiasts, while the nearby national state park offers picturesque hiking trails and natural beauty. Whether you’re enjoying a leisurely picnic or exploring the scenic surroundings, Georgetown promises a refreshing travel experience.
• Tolchester Beach: Located just a short drive from Chestertown, Tolchester Beach is a delightful seaside village that captures the essence of beach life. Known for its stunning scenery and outdoor activities, this destination features a lively boardwalk and recreational spaces ideal for sunbathing, swimming, and beach games. With its proximity to the marina and national state park, you can enjoy water sports or a peaceful stroll along the shore. Tolchester Beach is perfect for those looking to unwind and soak up the sun.
• Pomona: A quaint village situated near Chestertown, Pomona offers a unique blend of beach culture and artistic charm. Travelers flock to Pomona for its vibrant arts center and educational opportunities, making it an excellent spot for culture enthusiasts. The local marina and harbor provide stunning views and access to various water activities, while the nearby beach invites relaxation and exploration. With its inviting atmosphere, Pomona is an ideal destination for those seeking a combination of outdoor fun and cultural experiences.

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. Peak season runs in April and June to July, while off-peak times, like November to January tend to have fewer bookings and better deals.

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

Booking with Vrbo is a breeze

Looking to save on your next vacation? Consider being flexible with your travel dates, as prices can fluctuate. Plus, opting for a longer stay can often result in significant savings. To discover the ideal Vrbo property that fits your budget, utilize our filters to narrow down your search by price, location, and type of vacation rental.

Unlock savings with One Key

Reserve a qualifying Vrbo for your group getaway and earn OneKeyCash™ on your booking. Being the planner truly has its rewards! When you join our travel rewards program, One Key, you’ll gain immediate access to member savings and can earn and redeem OneKeyCash™ on eligible reservations. Sign up today to start enjoying your savings!

Vrbo Trips: Planning as easy as it gets

Vrbo's cutting-edge Trip Board offers you a convenient platform to plan new trips, pick up where you left off, or manage and organize your travel plans. You can easily access the properties you've saved or booked in the sections for Potential, Upcoming, or Current Trips. To start using Trip Boards, simply visit: https://www.vrbo.com/en-ca/trips.