Chestertown vacation rentals

We found 56 vacation rentals — enter your dates for availability

Discover a selection of 24 homes and other vacation rentals in Chestertown that are perfect for your trip. Vacation homes provide the amenities you need and want for you and your friends, family, or even pets, including parking and a garden. At the end of the day, you'll be able to choose a rental for everyone's needs, including accessible or non-smoking choices.

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Find out more about Chestertown

Why visit Chestertown

  • Scenic Outdoor Spaces: Experience the natural beauty of Chestertown with its urban parks, marinas, and beautiful beaches.
  • Charming Downtown: Explore quaint shops and cafes in the historic downtown area, perfect for leisurely strolls.
  • Waterfront Views: Enjoy stunning views along the scenic riverfront, ideal for family outings and relaxation.
  • Diverse Accommodations: Choose from cozy vacation homes, charming cottages, or modern apartments to suit your stay.
  • Rich Heritage: Immerse yourself in the local history and culture that adds to Chestertown's unique charm.

Popular types of accommodation in Chestertown

Discover the charm of Chestertown, MD, with a variety of vacation rentals that cater to every traveler’s needs. From cozy houses and charming cottages to modern apartments, you'll find the perfect place to unwind and explore. Whether you’re seeking a spacious house rental or a quaint cottage for a peaceful getaway, Chestertown offers a delightful selection to ensure a memorable stay in this picturesque town.

  • Houses: The top choice for visitors seeking a home-away-from-home experience in Chestertown, perfect for families and groups.
  • Cottages: A charming option that offers a cozy atmosphere, ideal for a romantic getaway or a peaceful retreat.
  • Apartments: Conveniently located and fully equipped, apartments are great for those wanting a more urban living experience.
  • Condos: Offering modern amenities and community features, condos provide a comfortable stay with easy access to local attractions.
  • House Boats: For a unique experience, house boats offer a delightful stay on the water, combining adventure with relaxation.**

Top attractions in Chestertown

Chestertown, Maryland, is perfect for a scenic outdoor vacation, offering a blend of urban parks, marinas, and beautiful beaches. Whether you're traveling with family or friends, you'll find plenty of attractions to enjoy. Explore the local parks and waterfront areas to fully experience the natural beauty and charm this quaint town has to offer. Don't miss out on the outdoor adventures that await you in and around Chestertown.

  • Washington College: Nestled in the heart of Chestertown, Washington College offers a rich history and vibrant campus life. Explore its charming architecture, art galleries, and engage with cultural events that reflect the college's commitment to liberal arts education.
  • Rolphs Wharf Marina: Experience outdoor adventures at Rolphs Wharf Marina. Enjoy boating, kayaking, and fishing while soaking in the beautiful waterfront views. It's a perfect spot for relaxation and fun activities in a picturesque setting.
  • Historical Society of Kent County Maryland: Immerse yourself in the local history at the Historical Society of Kent County. Discover fascinating exhibits and artifacts that showcase the region's heritage, making it a cultural gem in Chestertown.

Things to do recommended for couples

For a romantic getaway in Chestertown, explore the enchanting Cassinelli Winery and Vineyards, only 7 miles away. Delight in the charming Crow Farm and Vineyard, 10 miles out, or savor the atmosphere at Tilmon's Island Winery, located 11 miles from town. Perfect for couples seeking local experiences.

Things to do recommended for families

Families will love exploring the historic Chestertown waterfront, taking a scenic kayak tour on the Chester River, or visiting the nearby Sultana Education Foundation for hands-on maritime activities. Don't miss the local farmers' market for fresh produce and unique crafts.

Things to do recommended for groups

In Chestertown, your group can enjoy a captivating performance at the Garfield Center for the Arts, indulge in shopping at the Queenstown Premium Outlets, or play a round of golf at the scenic Queenstown Harbor Golf Club, all while soaking up the local culture and vibes.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

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

When planning your trip—whether you're traveling with friends, family, pets, or seeking extended stays—be sure to prioritize your filters accordingly. Here are some helpful Vrbo booking tips 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 area for group gatherings. Thankfully, you can easily filter for these options and many more on Vrbo.
  • Traveling to Chestertown with young kids: Traveling with young kids can present its own set of challenges. It's important to prioritize their comfort and safety, along with ensuring access to age-appropriate amenities like a private pool. Additionally, being close to family-friendly attractions is worth considering.
  • Taking your pets with you to Chestertown: For many families, a vacation isn’t truly a getaway without their furry companion. If that resonates with you, explore Vrbo listings that welcome pets. Most pet-friendly properties come equipped with feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Chestertown: If you're searching for vacation rentals with discounts 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 a private pool in your search criteria as well.

Where to stay in and around Chestertown

Chestertown, Maryland, offers a delightful blend of history and outdoor beauty. Explore the charming downtown area with its quaint shops and cafes, or take in stunning waterfront views. Perfect for family outings, visitors can enjoy relaxing strolls along the historic streets and scenic riverfront. Whether you're seeking a budget-friendly getaway or a family-friendly adventure, Chestertown's welcoming atmosphere and rich heritage promise an unforgettable vacation experience.

  • Worton: Located a mere 4 miles from Chestertown, Worton is a charming city that offers an array of outdoor adventures and scenic beauty. Known for its recreational areas and educational opportunities, visitors can enjoy activities such as hiking and boating at nearby landmarks like the national state park and the marina. The beautiful beaches and lush landscapes make Worton an ideal spot for those seeking relaxation in nature, making it a great destination for families and outdoor enthusiasts alike.
  • Georgetown: Nestled close to Chestertown, Georgetown is a delightful village perfect for travelers in search of outdoor adventures and romantic getaways. With access to a recreational area and a recreation center, visitors can partake in various activities, including sports at the local stadium. The nearby national state park offers stunning views and hiking opportunities, making it an ideal location for couples and adventurers looking to explore the great outdoors together.
  • Tolchester Beach: This picturesque village near Chestertown is a haven for beach lovers and outdoor aficionados. Known for its stunning scenery and recreational areas, Tolchester Beach boasts beautiful beaches and a charming boardwalk, perfect for leisurely strolls. The marina and proximity to the national state park provide ample opportunities for water sports, picnics, and exploring nature. Whether you’re looking to relax by the shore or enjoy outdoor activities, Tolchester Beach is a must-visit destination for your vacation.

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.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January34.2°F (1.2°C)Light RainMostly SunnySlightly LowSlightly Low
February36.9°F (2.7°C)Light RainMostly SunnyAverageSlightly Low
March43.7°F (6.5°C)Light RainMostly SunnyAverageSlightly Low
April54.3°F (12.4°C)Light RainMostly SunnySlightly HighAverage
May63.7°F (17.6°C)Light RainMostly SunnyAverageSlightly High
June72.1°F (22.3°C)Light RainMostly SunnySlightly HighAverage
July77.4°F (25.2°C)Light RainMostly SunnySlightly HighSlightly High
August75.6°F (24.2°C)Light RainMostly SunnyAverageSlightly High
September69.4°F (20.8°C)Light RainMostly SunnyAverageAverage
October59.2°F (15.1°C)Light RainMostly SunnyAverageAverage
November47.3°F (8.5°C)Light RainMostly SunnySlightly LowAverage
December40.1°F (4.5°C)Light RainMostly SunnySlightly LowAverage

Booking with Vrbo is simple

Looking to save on your upcoming trip? Consider being flexible with your travel dates, as this can lead to significant price differences. Plus, extending your stay often results in even greater savings. To discover the ideal Vrbo property that fits your budget, utilize our filters to sort by price, location, and type of vacation rental.

Unlock savings with One Key

Plan your group trip by booking an eligible Vrbo and earn OneKeyCash on the total amount of your reservation. Being the planner truly has its rewards. When you join our travel rewards program, One Key, you’ll gain access to exclusive discounts and accumulate OneKeyCash on qualifying bookings. Sign up today and begin enjoying your savings.

Vrbo Trips: Effortless planning

Vrbo's cutting-edge Trip Board offers you a dedicated space to plan new getaways, pick up right where you left off, and manage all your travel arrangements. You can easily access the properties you've saved or booked, now organized under Potential, Upcoming, or Current Trips. To explore Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

Why people love visiting cozy Chestertown

Take a vacation 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 vacation rentals feature full kitchens and laundry facilities.

Activities and attractions in Chestertown

Do you want to find top things to see and do while you're in the area? Venture out of your vacation home and experience everything that makes Chestertown a one-of-a-kind vacation spot. These are some of the most popular attractions to put on your list, all within 30 miles (48.2 km) of the city center:

  • Queenstown Harbor Golf Club (16.7 mi / 26.9 km)
  • Queenstown Harbor Golf Links (16.7 mi / 26.9 km)
  • Paul Reed Smith Guitars (20.7 mi / 33.3 km)
  • Compass Pointe Golf Courses (23.8 mi / 38.2 km)
  • Bay Hills Golf Club (25 mi / 40.2 km)
  • Cassinelli Winery and Vineyards (7.1 mi / 11.3 km)

Exploring the natural landscape of Chestertown

Whether you're an adventurous traveler or just want to spend some time taking in the scenery, Chestertown is a great place to spend some time outside. Here are some of the area’s noteworthy sights, all within 30 miles (48.2 km) of the city center:

  • Betterton Beach (10.5 mi / 16.9 km)
  • Ferry Park (11.5 mi / 18.5 km)
  • Eastern Neck National Wildlife Refuge (15.4 mi / 24.8 km)
  • Miami Beach (17.2 mi / 27.7 km)
  • Cuckold Point (17.7 mi / 28.5 km)
  • Rocky Point Park and Beach (18.1 mi / 29.2 km)

Transportation 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 center. If you can't find a flight that's convenient for your trip, you could also fly into Easton, MD (ESN-Easton - Newnam), which is 28.2 mi (45.3 km) away.

Frequently asked questions

What is the best area to stay in Chestertown, Maryland, United States of America when booking a vacation rental?
When considering the best area to stay in Chestertown, Maryland, you should definitely look into the historic downtown neighborhood. This charming area is known for its picturesque streets and well-preserved buildings that reflect the town's rich history. Staying here places you within walking distance of several top attractions, including the beautiful Chestertown waterfront, where you can enjoy scenic views and leisurely strolls along the banks of the Chester River. Additionally, the nearby historic courthouse and the lively Farmers Market provide a taste of local culture and community spirit.

Another appealing option is the area surrounding Washington College, which not only adds a youthful vibe to the town but also features beautiful campus grounds that can be enjoyed by visitors. This location is convenient for exploring local art galleries, boutique shops, and delightful restaurants that showcase the area's culinary scene.
How much does it cost to rent a vacation home in Chestertown?
Prices for vacation rentals in Chestertown vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Chestertown to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Chestertown vacation house rentals?
You can find great discounts on house rentals in Chestertown on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Where are the best areas for renting a beach house in Chestertown?
For renting a beach house in Chestertown, the area along the Chesapeake Bay offers some delightful options. The waterfront properties near the Chestertown Marina provide easy access to the bay, with many rentals featuring amenities such as private docks, outdoor decks, and spacious living areas, ideal for families or groups looking to enjoy water activities and stunning views of the bay.

In addition, the nearby community of Rock Hall, just a short drive away, is known for its charming beach homes. Here, travelers can find rentals equipped with outdoor grills, fire pits, and sandy beach access, superb for evening gatherings and enjoying the coastal atmosphere. The local fishing spots and recreational opportunities, such as kayaking or paddleboarding, further enhance the beach experience in this region.

For those who enjoy exploring local attractions, Chestertown itself offers a historic downtown area with quaint shops, galleries, and restaurants, all within reach from various vacation rentals. Properties in this area often come with amenities that cater to relaxation and comfort, including cozy porches and fully equipped kitchens, making it a superb destination for a beach getaway on the Eastern Shore.
What is the most popular type of vacation rental accomodation in Chestertown?
In Chestertown, vacation houses are the most popular type of rental, with about 23 available in the area. These homes typically feature multiple bedrooms, fully equipped kitchens, and spacious living areas, making them ideal for families or groups. Many of these properties also include outdoor spaces such as gardens or porches, great for enjoying the pleasant Maryland weather. Additionally, there are several apartments, cottages, and cabins available, offering various options for travelers looking for a cozy stay near the historic downtown and the scenic Chester River.
Are there any family house rentals in Chestertown?
In Chestertown, Maryland, there are numerous family-friendly house rentals available—around 25 options throughout the area. This charming town, known for its historic architecture and waterfront views, provides a great backdrop for family gatherings. Many homes offer spacious living areas, fully equipped kitchens superb for preparing family meals, and outdoor spaces where children can enjoy the fresh air. Amenities such as Wi-Fi and air conditioning are typically included, ensuring a comfortable stay for everyone.

Visitors can explore nearby attractions like the Chestertown Historic District, which is rich in history and culture, or take a relaxing stroll along the Chester River. The town also features parks and recreational areas, ideal for outdoor activities and family picnics.
Can I rent a vacation home with a pool or hot tub in Chestertown?
In Chestertown, Maryland, there are several vacation homes available for rent that feature pools and hot tubs. This charming town, located along the Chester River, offers a picturesque setting for travelers looking to relax and unwind. Many of the rentals in the area come equipped with private pools, hot tubs, and spacious outdoor areas, superb for enjoying the beautiful Maryland weather.

You can expect amenities such as fully equipped kitchens for preparing meals, comfortable living spaces, and often additional features like outdoor patios or decks for entertaining.
Can I find long-stay vacation rentals in Chestertown?
A long-stay vacation rental in Chestertown is the best way to experience local living. Plus, you can make the most of long-stay discounts. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Are there pet-friendly house rentals in Chestertown?
In Chestertown, there are several pet-friendly house rentals available, with a total of 13 options for travelers to consider. The town is known for its charming historic district, where visitors can find rentals that offer amenities such as fully equipped kitchens, spacious living areas, and outdoor spaces like patios or gardens, great for pets to enjoy.

Chestertown is conveniently located near scenic parks and waterfront areas. The Chestertown Riverwalk offers picturesque views and opportunities for leisurely strolls with pets along the banks of the Chester River. Additionally, nearby parks provide open spaces for pet-friendly activities, ensuring that both travelers and their furry companions have plenty of options for outdoor enjoyment.
Are there any remote work vacation rentals in Chestertown?
In Chestertown, Maryland, there are numerous remote work-friendly vacation rentals available, with about 32 options for travelers to choose from. Many of these properties cater specifically to those looking to balance work and leisure, offering amenities such as high-speed Wi-Fi, dedicated workspaces, and comfortable living areas conducive to productivity.

Travelers can expect a variety of accommodations, including cozy cottages and spacious homes, often featuring fully equipped kitchens for convenient meal preparation and outdoor spaces for relaxation during breaks. The town's charming historic district provides a picturesque backdrop, with local shops and eateries just a short stroll away. Chestertown also boasts nearby attractions such as the Chester River, superb for enjoying nature and outdoor activities on downtime. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Chestertown vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Chestertown with parking available—perfect for families or travelers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
What are popular rental amenities in Chestertown?
In Chestertown, travelers can expect a variety of popular rental amenities that enhance their stay. Most vacation rentals feature fully equipped kitchens, allowing guests to prepare their own meals. Many properties also include outdoor spaces like decks or patios, superb for enjoying the pleasant Maryland weather. Onsite parking is commonly available, providing convenience for those traveling with vehicles.
When is the best time to visit Chestertown for a vacation rental?
The best time to visit Chestertown for a vacation rental is during the summer months, particularly in July. This period marks the peak travel season, when visitors flock to this charming town to enjoy the warm weather, vibrant community events, and scenic waterfront views. With temperatures typically ranging from the mid-70s to low 90s Fahrenheit, it's an ideal time for outdoor activities such as kayaking, cycling, and strolling along the picturesque streets filled with historic homes.

Chestertown comes alive in July, offering a lively option with a variety of local festivals and cultural happenings. This is a fantastic time for families and groups looking to engage in outdoor adventures or simply relax by the Chester River. The summer months also provide ample opportunities for sightseeing, including visits to local galleries, shops, and the renowned Chestertown Farmers Market.

For travelers seeking a more budget-friendly option, consider visiting in November. While this is a quieter time, it offers a unique charm with fewer crowds and the chance to experience the town's beautiful fall scenery and local traditions without the hustle of peak season.
How early should I book a Chestertown vacation rental?
Book your Chestertown vacation rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Chestertown, Maryland, United States of America?
In Chestertown, visitors can explore a variety of charming attractions that highlight the town's historical and cultural significance. The historic district features beautifully preserved 18th-century buildings, with the Chestertown Tea Party Festival commemorating the town's role in the American Revolution. Nearby, the Washington College campus offers picturesque grounds and art galleries, including the Kohl Gallery, which showcases contemporary art.

The waterfront area along the Chester River is ideal for leisurely strolls, where you can enjoy views of the water and watch boats pass by. The RiverArts organization frequently hosts events and exhibits, allowing visitors to engage with local artists and craftspeople. For outdoor enthusiasts, the nearby Eastern Neck National Wildlife Refuge provides opportunities for hiking, bird watching, and enjoying nature.
Can I change or cancel my Chestertown home rental booking on Vrbo?
To find Chestertown vacation rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travelers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cozy cabin or a beach condo, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.

Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Chestertown vacation rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable.

If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively.

Vrbo also offers support via live chat through our Help Center, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organizing group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

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