Chestertown holiday homes

We found 61 holiday rentals — enter your dates for availability
Discover a selection of 29 homes and other holiday rentals in Chestertown that are perfect for your trip. Holiday homes offer the best amenities for your stay with friends, family or just your pet, including parking and a garden. Whatever you're looking for, you'll be sure to find a property to rent to meet everyone's needs, including a place that's non-smoking or offers accessibility.

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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.

*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 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 iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
January34.2°F (1.2°C)Light RainMostly SunnySlightly Low
February36.9°F (2.7°C)Light RainMostly SunnyAverage
March43.7°F (6.5°C)Light RainMostly SunnyAverage
April54.3°F (12.4°C)Light RainMostly SunnySlightly High
May63.7°F (17.6°C)Light RainMostly SunnyAverage
June72.1°F (22.3°C)Light RainMostly SunnySlightly High
July77.4°F (25.2°C)Light RainMostly SunnySlightly High
August75.6°F (24.2°C)Light RainMostly SunnyAverage
September69.4°F (20.8°C)Light RainMostly SunnyAverage
October59.2°F (15.1°C)Light RainMostly SunnyAverage
November47.3°F (8.5°C)Light RainMostly SunnySlightly Low
December40.1°F (4.5°C)Light RainMostly SunnySlightly 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:

  • Queenstown Harbor Golf (16.7 mi / 26.9 km)
  • Bay Hills Golf Club (25 mi / 40.2 km)
  • Cassinelli Winery and Vineyards (7.1 mi / 11.3 km)
  • Crow Farm and Vineyard (10.2 mi / 16.4 km)
  • Paul Reed Smith Guitars (20.7 mi / 33.3 km)
  • Compass Pointe Golf Courses (23.8 mi / 38.2 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)
  • Sandy Point Beach (22.6 mi / 36.4 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.

Frequently asked questions

What is the best area to stay in Chestertown when booking a holiday rental?
When considering a holiday rental in Chestertown, Maryland, the historic district is the best area to stay. This charming neighbourhood is known for its stunning historic architecture and picturesque streets, making it a delightful spot for visitors. With a variety of properties ranging from quaint cottages to elegant homes, you'll find numerous options that cater to different tastes and budgets.One of the top attractions in this area is the Chestertown Tea Party Festival, which celebrates the town's rich history and community spirit. Additionally, the beautiful waterfront along the Chester River offers opportunities for leisurely strolls and scenic views. The nearby Historical Society of Kent County provides insights into the local heritage, making it a must-visit for history enthusiasts.
Where are the best areas for renting a beach house in Chestertown?
For renting a beach house in Chestertown, the nearby areas along the Chesapeake Bay offer picturesque options. The town of Rock Hall, located just a short drive away, features charming waterfront properties with stunning views of the bay. Many of these rentals come equipped with amenities such as private docks, outdoor grilling areas, and spacious decks, superb for enjoying the serene surroundings and sunset vistas.In addition, the Kent Narrows area provides further beach house opportunities, where visitors can find properties that often include amenities like kayaks or paddleboards for guests to use, allowing for easy exploration of the waterways. The proximity to local seafood restaurants and shops adds to the convenience for holidayers looking to immerse themselves in the local culture.For those interested in a more tranquil setting, the Kent County area boasts rental homes surrounded by nature, often featuring private gardens, fire pits, and easy access to walking trails along the water.
What is the most popular type of holiday rental accomodation in Chestertown?
In Chestertown, holiday houses are the most popular type of holiday rental, with about 46 available in various charming neighbourhoods. These homes typically feature multiple bedrooms, spacious living areas, and fully equipped kitchens, making them ideal for families or groups looking for a comfortable stay. Additionally, many holiday houses offer outdoor spaces such as patios or gardens, great for enjoying the pleasant Maryland weather. There are also around 12 apartments, which provide a more compact and easy-to-manage option, often situated near the town centre and local attractions. For those seeking a quaint experience, several cottages and cabins are available as well, offering a unique and cosy ambiance in a picturesque setting.
Are there any family house rentals in Chestertown?
In Chestertown, Maryland, there are plenty of family-friendly holiday rentals available, with around 25 options to choose from. The charming downtown area is a delightful spot for families, offering a mix of historic architecture and waterfront views along the Chester River. Many of the homes in this locale feature spacious living areas, full kitchens superb for preparing family meals, and outdoor spaces for children to play.Visitors can enjoy amenities such as air conditioning, Wi-Fi, and some properties even boast private gardens or patios for relaxation. Nearby attractions include the beautiful Chestertown Historic District, where families can explore shops, cafes, and art galleries. Additionally, the waterfront provides opportunities for kayaking and fishing, making it a great destination for outdoor activities.
Can I rent a holiday home with a pool or hot tub in Chestertown?
In Chestertown, Maryland, several holiday homes are available for rent that feature pools or hot tubs. This charming town, located along the picturesque Chester River, offers a lovely setting for relaxation and leisure. Travellers can expect amenities such as private pools, outdoor seating areas, and hot tubs, ideal for unwinding after a day of exploring the local attractions. Many properties also come equipped with fully furnished kitchens, spacious living areas, and often include access to beautiful outdoor spaces, great for family gatherings or socialising with friends.
Are there pet-friendly house rentals in Chestertown?
In Chestertown, there are several pet-friendly house rentals available, allowing travellers to enjoy this charming town alongside their furry companions. Many of these homes come equipped with amenities such as fully equipped kitchens, spacious living areas, and outdoor spaces, great for relaxing after a day of exploring.The town's historic district offers a delightful atmosphere with its quaint streets, and several properties are within walking distance of local shops and restaurants that welcome pets. Additionally, the nearby Chesapeake Bay provides beautiful waterfront parks, where you can enjoy leisurely strolls with your pets while taking in scenic views.
Are there any remote work holiday rentals in Chestertown?
In Chestertown, Maryland, there are numerous options for remote work holiday rentals, with around 64 available throughout the area. This charming town, known for its historic waterfront and vibrant arts scene, offers a variety of properties suitable for those looking to combine work and leisure. Many of these rentals feature essential amenities such as high-speed Wi-Fi, dedicated workspaces, and comfortable living areas that allow for a productive environment.Travellers can expect to find properties equipped with desks, free in-room Wi-Fi, and other conveniences conducive to remote work. Additionally, the picturesque surroundings provide a relaxing backdrop for after-work activities, with nearby attractions such as the Chestertown Historic District and the scenic Chester River. To help narrow your search, insert your dates and apply the "WiFi" filter on Bookabach.
What are popular rental amenities in Chestertown?
In Chestertown, popular rental amenities include fully equipped kitchens, allowing guests to prepare their own meals. Many properties feature decks or patios, providing outdoor space to relax and enjoy the surrounding scenery. Onsite parking is also commonly available, making it convenient for those travelling by car. Additionally, rentals often come with coffee and tea makers, as well as blenders for those who enjoy morning beverages or smoothies.
When is the best time to visit Chestertown for a holiday rental?
July is the most popular time to visit Chestertown, Maryland, drawing in families and holidaymakers eager to soak up the summer sun and the charming atmosphere of this historic town. The peak season, spanning from June to August, offers an array of outdoor activities, including leisurely strolls along the waterfront, kayaking on the Chester River, and exploring the vibrant local shops.During this busy period, temperatures typically hover around the mid to high 20s Celsius, making it ideal for enjoying al fresco dining and the various festivals hosted in the area. The lively energy of summer is palpable, with events such as the Chestertown Tea Party Festival, which celebrates the town's rich history.For those looking for a more tranquil experience, consider visiting in November. This month presents a wonderful opportunity to enjoy the beauty of Chestertown in a quieter setting, with fewer crowds allowing for a more relaxed exploration of the town's picturesque streets. The autumn foliage adds a stunning backdrop for scenic walks and photography.
What are the top attractions in Chestertown?
In Chestertown, visitors can explore a charming array of attractions that showcase the town's rich history and scenic beauty. The historic district, with its well-preserved 18th-century buildings, is superb for leisurely strolls, allowing tourists to appreciate the local architecture and visit the Chestertown Tea Party Festival site.The waterfront along the Chester River offers picturesque views, and the nearby Fountain Park provides a lovely green space for relaxation or picnics. Art enthusiasts can enjoy the various galleries, including the RiverArts Gallery, which often features local artists and rotating exhibitions.For those interested in history, the Custom House and the Historical Society of Kent County offer insights into the region's past, while the nearby Washington College adds a vibrant setting with its beautiful campus and cultural events.
Are all fees included in the Chestertown holiday homes prices shown on Bookabach?
Bookabach 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.
Are there any Chestertown holiday homes with parking?
Bookabach offers a wide selection of holiday homes in Chestertown with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details 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.
Are there any discounts for Chestertown holiday homes?
You can find great discounts on holiday homes in Chestertown on Bookabach, 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.
Can I change or cancel my Chestertown holiday home booking on Bookabach?
To find Chestertown holiday rentals with free cancellation, just use Bookabach'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". Whether you're adjusting your plans or looking for flexible payment options, Bookabach makes it easy to book with confidence.
Can I find long-stay holiday homes in Chestertown?
A long-stay holiday home in Chestertown is the best way to experience local living. Plus, you can make the most of long-stay discounts. 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.
Can I plan a group trip on Bookabach?
Bookabach's Trip Planner makes organising 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 favourites, and build the perfect itinerary together.
How early should I book a Chestertown holiday home?
Book your Chestertown holiday home 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 Bookabach booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Chestertown?
Prices for holiday homes 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 travelling solo, as a couple, with family, or in a group. Bookabach offers something for every taste and budget, from affordable homes in Chestertown to more spacious homes.
What can I expect from Bookabach customer service and Bookabach Care™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, Bookabach Care™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Bookabach customer service is available 24/7 to support you every step of the way. Bookabach also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is Bookabach Care™ and how does it work?
Bookabach's mission is to help guests relax, reconnect, and enjoy precious time together. With Bookabach Care™, 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.
Why should I join Bookabach as a host?
Joining Bookabach as a host opens the door to a global community of travellers 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, Bookabach makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Bookabach handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

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