Chestertown vacation rentals

We found 56 vacation rentals — enter your dates for availability

Discover a selection of 23 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.

Find spaces that suit your style

  • Peace of mind

    Our Book with Confidence guarantee gives you 24/7 support

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, yards and more

  • More for less

    More space, more privacy, more amenities — more value

  • A place for everyone

    We stand for diversity, inclusion and families everywhere.
    Learn more

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:

  • Crumpton Auction (8.4 mi / 13.5 km)
  • Queenstown Harbor Golf Club (16.7 mi / 26.9 km)
  • Queenstown Harbor Golf Links (16.7 mi / 26.9 km)
  • Bay Hills Golf Club (25 mi / 40.2 km)
  • Crow Farm and Vineyard (10.2 mi / 16.4 km)
  • Tilmon's Island Winery (11.1 mi / 17.9 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)
  • 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)
  • Belcamp Beach (19.2 mi / 30.9 km)
  • North East Beach Area (19.4 mi / 31.3 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 when booking a vacation rental?
When planning a vacation in Chestertown, Maryland, one of the best areas to consider for your stay is the charming historic district. This area is rich in history and offers a picturesque setting with well-preserved historic architecture. Staying here puts you within walking distance of several top attractions, such as the Chestertown Tea Party Festival, which celebrates the town's revolutionary history, and the beautiful Fountain Park, superb for leisurely strolls and enjoying the natural surroundings.

Another great option is the waterfront area along the Chester River. This picturesque setting not only provides stunning views but also easy access to activities like kayaking and boating. The nearby Wilmer Park offers a lovely spot for picnics, and you can often catch local events or markets in this vibrant community space. In terms of vacation rentals, the historic district typically features a wide range of properties, from cozy cottages to elegant homes, providing numerous options to suit various preferences and group sizes.
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, Maryland, travelers should focus on the areas along the Chester River and nearby Chesapeake Bay. The waterfront neighborhoods in Chestertown, particularly those close to the historic downtown area, provide charming vacation rentals with easy access to water activities and beautiful views. Many properties here come equipped with amenities such as private docks, outdoor decks, and spacious living areas, making them superb for families or groups looking for a relaxing getaway.

Additionally, the area around Wilmer Park offers picturesque settings where visitors can find beach houses that feature amenities like fire pits, barbecues, and direct access to the park's sandy beach area. This location is ideal for those who enjoy picnicking, kayaking, or simply lounging by the water.

Exploring the nearby Kent County offers more options, with properties that showcase the region's natural beauty, often featuring amenities such as screened porches, expansive yards, and proximity to walking trails. Travelers can enjoy both the tranquil ambiance of the river and the vibrant local culture, with shops and restaurants just a short drive away. Find your rental near the beach in Chestertown.
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 throughout the area. These houses often feature spacious layouts, multiple bedrooms, and fully equipped kitchens, making them ideal for families or groups. Many properties also include outdoor spaces like gardens or patios, superb for enjoying the picturesque views of the Chester River or the charming streets of the historic district. Additionally, there are several apartments, cottages, and cabins that provide alternative options for travelers seeking a cozier or more unique stay.
Are there any family house rentals in Chestertown?
In Chestertown, Maryland, families have a variety of rental options to choose from—around 24 homes available in the area. This charming town, located along the Chester River, is great for family getaways, offering properties that often include spacious living areas, fully equipped kitchens ideal for preparing meals together, and outdoor spaces for kids to enjoy. Many homes also feature amenities such as Wi-Fi and air conditioning, ensuring a comfortable stay for everyone.

Visitors can explore the picturesque downtown, where quaint shops and local eateries await. The nearby Washington College adds a cultural touch to the area, often hosting events that families can enjoy. Additionally, Chestertown's proximity to the river provides opportunities for outdoor activities like kayaking and fishing, making it a versatile destination for families looking to relax and engage with nature. See all family-friendly rentals in Chestertown.
Can I rent a vacation home with a pool or hot tub in Chestertown?
In Chestertown, Maryland, travelers can find several vacation homes available for rent that feature pools and hot tubs. This charming town, situated along the Chester River, offers a serene atmosphere great for relaxation. Many of these properties come equipped with private pools, spacious outdoor areas, and comfortable living spaces, ideal for families or groups looking to unwind.

Rentals may also include amenities such as fully equipped kitchens for home-cooked meals, outdoor lounges for entertaining, and beautiful gardens to enjoy the picturesque surroundings. Find your rental in Chestertown with a pool or a hot tub.
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, providing a welcoming environment for travelers with furry companions. Many of these vacation homes come equipped with desirable amenities such as spacious backyards, modern kitchens, and cozy living areas, making them suitable for family gatherings or a peaceful retreat.

The town itself is known for its historic charm, and visitors can enjoy leisurely strolls along the waterfront or explore the quaint downtown area filled with local shops and eateries. Nearby parks, such as Wilmer Park, offer open spaces for pets to roam and enjoy the outdoors, enhancing the overall pet-friendly experience. Chestertown's proximity to the Chesapeake Bay also allows for exciting outdoor activities, including kayaking and fishing, which can be enjoyed with pets in tow. See all pet-friendly rentals in Chestertown.
Are there any remote work vacation rentals in Chestertown?
In Chestertown, Maryland, there are several remote work vacation rentals available, with around 29 options to choose from. This charming town, known for its historic waterfront and vibrant arts scene, offers a variety of properties that cater to remote workers. Many of these rentals come equipped with essential amenities such as dedicated workspaces, high-speed Wi-Fi, and comfortable desk chairs, ensuring a productive environment. Some properties may also feature additional conveniences like laptop workspaces and safe storage for personal items.

The town itself provides a picturesque backdrop for work and leisure, with nearby attractions including the scenic Chester River and local parks superb for a break from work. Additionally, Chestertown's quaint downtown area offers a selection of cafes and shops, making it easy to take a stroll or grab a quick bite between remote work sessions. 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, popular rental amenities include WiFi, kitchens, and outdoor patios, making it easy for guests to stay connected and enjoy meals at their convenience. Many rentals also feature a blender for preparing smoothies or other snacks, along with coffee and tea makers for a warm beverage at any time of day.
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 peak season from June to August, with July being the most popular month. This vibrant period draws visitors eager to experience the charming waterfront town, known for its rich history and cultural events. Perfectly suited for travelers looking for outdoor activities, this season offers warm temperatures, typically in the mid-70s to low 90s Fahrenheit, ideal for exploring local attractions, enjoying water sports, or simply strolling through the beautiful historic district.

During the summer, Chestertown hosts various festivals and events, creating a lively atmosphere that enhances your experience. Whether you're dining at quaint waterfront restaurants or attending art shows, the summer months provide ample opportunities for engagement with the local community and the surrounding natural beauty.

For those who prefer a quieter experience while still enjoying the beauty of Chestertown, consider visiting in November. This month offers a tranquil setting, superb for savoring the fall colors and indulging in leisurely walks along the Chester River. The milder temperatures and fewer crowds make it an attractive option for travelers seeking relaxation and a slower pace.

Ultimately, your choice may depend on whether you're looking to immerse yourself in the vibrant summer festivities or to enjoy a peaceful getaway as the seasons change.
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?
In Chestertown, visitors can engage in a rich blend of history and culture. The historic downtown area, with its charming 18th-century architecture, is home to the National Historic Landmark District, where travelers can explore unique boutiques, art galleries, and local eateries. The Chestertown Tea Party Festival celebrates the town's history and offers a vibrant atmosphere for visitors.

The waterfront along the Chester River is a prime spot for enjoying scenic views, and vacation rentals here often provide easy access to activities like kayaking, sailing, and fishing. Nearby, the Washington College campus adds a youthful energy to the area, with events and exhibitions open to the public.
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.

More Vacation Ideas