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Chestertown vacation rentals

We found 55 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.

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Find out more about Chestertown

Why visit Chestertown

  1. Historic charm: Explore the enchanting historic district, featuring stunning colonial architecture and a vibrant waterfront.
  2. Outdoor adventures: Chestertown is perfect for nature lovers, offering scenic beaches, parks, and marinas for relaxation and exploration.
  3. Family-friendly atmosphere: The welcoming neighbourhoods provide a warm environment, ideal for families seeking a tranquil getaway.
  4. Scenic surroundings: Discover picturesque views and delightful small towns in the vicinity, perfect for day trips.
  5. Diverse accommodations: Choose from charming cottages, vacation homes, and comfortable apartments to suit your needs.

Popular types of accommodation in Chestertown

Planning a getaway to Chestertown? The next step is selecting the perfect accommodation to suit your needs. Explore a variety of options, including houses, charming cottages, and comfortable apartments. Whether you're looking for rentals near Chestertown or specific vacation house rentals, we've got you covered with transparent information and great savings. Your ideal Chestertown vacation rental awaits!

  • Houses: The top choice for visitors seeking a homey experience, these rentals provide ample space and amenities for families or groups.
  • Cottages: Quaint and charming, cottages offer a cozy retreat, perfect for couples or those looking for a serene getaway.
  • Apartments: Ideal for solo travellers or small groups, apartments combine convenience with comfort in the heart of Chestertown.
  • Condos: These modern accommodations feature shared amenities and are great for those wanting a vibrant community atmosphere.
  • House Boats: A unique option, house boats provide a floating home experience, perfect for adventurers looking to explore the waterway.**

Top attractions in Chestertown

Chestertown, Maryland, is an ideal destination for outdoor enthusiasts and families seeking a beach getaway. Visitors can enjoy scenic views at local beaches, urban parks, and marinas. The area offers various attractions perfect for creating memorable experiences, making it a great spot for a trip. Whether you're looking to relax by the water or explore nature, Chestertown has something for everyone to enjoy.

  1. Washington College: A historic institution in Chestertown, Washington College offers a blend of rich heritage and academic culture. Visitors can enjoy beautiful campus architecture and engage in various cultural events throughout the year.
  2. Rolphs Wharf Marina: Perfect for outdoor enthusiasts, Rolphs Wharf Marina provides stunning waterfront views and opportunities for adventure. Enjoy activities like boating, fishing, and relaxing on the beach while soaking in the natural beauty.
  3. River Arts Chestertown: This vibrant arts centre showcases local talent and creativity, featuring exhibitions, workshops, and events that celebrate the arts. Immerse yourself in the artistic community and enjoy unique cultural experiences.

Things to do recommended for couples

For a romantic getaway in Chestertown, explore the enchanting Cassinelli Winery and Vineyards, only 11.3km away, or visit Crow Farm and Vineyard, 16.1km distant. Don't miss Tilmon's Island Winery, situated 17.7km away, each offering charming vibes and delightful experiences for couples.

Things to do recommended for groups

Experience the vibrant culture at the Garfield Center for the Arts, perfect for a family outing. For shopping enthusiasts, the Queenstown Premium Outlets offers a variety of stores, while sports lovers can enjoy a round of golf at Queenstown Harbor Golf Club, all within 111.3km of Chestertown.

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

If you're travelling with a group, family, pets, or seeking longer stays, it's important to prioritise your preferences when filtering options. Here are some helpful Vrbo booking tips for you.

  • Traveling to Chestertown with a group: Think about how many bedrooms you'll require, along with features like a full kitchen or outdoor space for group gatherings. Luckily, you can easily filter for these options and more on Vrbo.
  • Traveling to Chestertown with young kids: Traveling with young children can present its own set of challenges. It's important to prioritize their comfort and safety, which includes seeking out age-appropriate 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 companion. If that resonates with you, explore Vrbo listings that welcome pets. Many of these pet-friendly accommodations come equipped with feeding bowls and beds, ensuring that your entire family feels comfortable and at home.
  • Planning for a long term stay visiting Chestertown: If you’re in search of vacation rentals offering 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 accommodations. Don’t forget to include options like a parking space, a well-equipped kitchen, or a private pool in your search as well.

Where to stay in Chestertown

Chestertown, Maryland, is a charming destination perfect for those seeking outdoor adventures and historical exploration. Stroll through the historic district to admire beautiful colonial architecture and visit the lively waterfront. Nearby, you'll find family-friendly neighbourhoods that offer a warm, inviting atmosphere, ideal for relaxation. Don't miss the opportunity to explore the scenic towns and picturesque views that surround Chestertown, making it a delightful spot for your vacation.

  • Georgetown: Nestled within the Chestertown area, Georgetown is a charming village that draws visitors seeking outdoor adventures and romantic escapes. The village's scenic surroundings offer a plethora of recreational activities, making it a perfect spot for nature lovers. Here, you can explore educational facilities and recreational areas that cater to both relaxation and adventure. Notable landmarks nearby include a sports facility stadium and a national state park, providing ample opportunities for outdoor activities like hiking, picnicking, and enjoying local wildlife.
  • Tolchester Beach: Located close to Chestertown, Tolchester Beach is a delightful village that promises a picturesque beach experience. Travelers flock here for its stunning scenery, boardwalks, and outdoor recreational opportunities. The beach is perfect for sunbathing, swimming, and beachcombing, while the marina offers various water activities. The nearby national state park adds to the allure, allowing visitors to immerse themselves in nature through hiking trails and scenic vistas. Tolchester Beach is an ideal destination for those looking to unwind by the water and soak in the breathtaking views.
  • Pomona: Pomona is a quaint village situated near Chestertown, offering a unique blend of beach, culture, and outdoor experiences. Visitors can enjoy the vibrant local arts scene at the local arts centre or take advantage of educational opportunities available in the area. The village is also home to beautiful beaches and a charming marina, making it an excellent location for water activities and leisurely strolls by the harbour. Pomona’s rich cultural experiences and stunning natural landscapes make it a must-visit for anyone looking to appreciate the beauty of Maryland's Eastern Shore.

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 iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
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

Are you hoping to save on your upcoming journey? Being flexible with your travel dates can make a difference, as prices often fluctuate. Additionally, planning for a longer stay can lead to considerable savings. To discover a Vrbo property that suits your budget, take advantage of our filters to sort by price, location, and type of vacation rental.

Vrbo Trips: Planning made easy

Vrbo's cutting-edge Trip Board offers you a dedicated area to plan new journeys, pick up from where you last stopped, or easily review and arrange your travel plans. You can now access previously saved and booked properties in the sections for Potential, Upcoming, or Current Trips. To explore the Trip Boards, simply visit: https://www.vrbo.com/en-ca/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)
  • Hazel Miner Monument (12 mi / 19.3 km)
  • Queenstown Harbor Golf Club (16.7 mi / 26.9 km)
  • Queenstown Harbor Golf Links (16.7 mi / 26.9 km)
  • Compass Pointe Golf Courses (23.8 mi / 38.2 km)
  • Bay Hills Golf Club (25 mi / 40.2 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)
  • North East Beach Area (19.4 mi / 31.3 km)
  • Chesapeake Bay Environmental Center (20.6 mi / 33.1 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 considering a vacation rental in Chestertown, Maryland, a popular area to stay is the historic downtown district. This charming area is rich in history and features picturesque streets lined with beautifully preserved 18th and 19th-century buildings. Staying here puts you within walking distance of delightful shops, cafes, and restaurants, allowing you to fully immerse yourself in the local culture. A key attraction in the downtown area is the Custom House, which offers insights into the town's maritime heritage and serves as a visitor centre.

Another excellent option is the waterfront area along the Chester River. This scenic locale provides stunning views and the opportunity for various recreational activities, such as kayaking and fishing. The nearby Wilmer Park is a lovely spot for a leisurely stroll or a picnic, and it often hosts community events and festivals. The waterfront area typically features a variety of vacation rental properties, suiting different preferences and budgets.
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 travelling 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.
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, the best options can be found along the scenic shores of the Chesapeake Bay. The area around Betterton Beach offers charming waterfront properties that provide direct access to sandy beaches and stunning sunset views. Many of these rentals come equipped with amenities such as outdoor decks, barbecue grills, and spacious living areas, making them great for families or groups looking to enjoy a relaxing getaway by the water.

Additionally, the nearby town of Rock Hall is known for its quaint atmosphere and offers a variety of vacation rentals, including cottages and larger homes that often feature kayaks or paddleboards for guests to explore the bay. Many properties in Rock Hall come with modern kitchens, fire pits, and private gardens, ideal for outdoor dining and socialising after a day spent on the beach.
What is the most popular type of vacation rental accomodation in Chestertown?
In Chestertown, vacation houses are the most popular rental option, with about 24 available throughout the town. These properties provide a spacious and comfortable environment, often featuring multiple bedrooms, fully equipped kitchens, and outdoor areas such as gardens or patios—ideal for families or groups looking to enjoy the local charm. Additionally, there are several apartments, cottages, and cabins that cater to different preferences. Many of these rentals are situated close to historical sites and the beautiful waterfront along the Chester River, allowing guests to immerse themselves in the area's rich history and scenic views.
Are there any family house rentals in Chestertown?
In Chestertown, Maryland, there are a variety of family-friendly house rentals available, with around 29 options to choose from. This charming town, located along the Chester River, offers a delightful blend of history and outdoor activities, making it an ideal destination for families. Properties often feature spacious living areas, fully equipped kitchens, and outdoor spaces superb for children to play and explore. Many homes also provide amenities like Wi-Fi and air conditioning, ensuring a comfortable stay for all.
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 scenic Chester River, offers a relaxed atmosphere great for a getaway. Many properties come with amenities such as private swimming pools, hot tubs for soothing relaxation, and spacious outdoor areas ideal for family gatherings or entertaining friends. Inside, travellers can expect fully equipped kitchens, comfortable living spaces, and often multiple bedrooms to accommodate larger groups.
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. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Are there pet-friendly house rentals in Chestertown?
In Chestertown, there are several pet-friendly house rentals available, providing a welcoming environment for travellers with furry companions. Many of these rentals typically feature amenities such as spacious backyards, modern kitchens, and comfortable living areas, allowing for a relaxing stay.
Are there any remote work vacation rentals in Chestertown?
In Chestertown, Maryland, there are numerous remote work vacation rentals available, with around 31 options to choose from. This charming town, known for its historic downtown and scenic waterfront along the Chester River, offers a variety of properties that cater to remote workers. Many of these rentals come equipped with essential amenities such as Wi-Fi, designated workspaces featuring desks and ergonomic chairs, and some even include computer monitors for added convenience. 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 travellers 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 vacation rental amenities typically include fully equipped kitchens, which allow travellers to prepare their own meals during their stay. Most rentals feature microwaves, cookware, dishware, and utensils, providing everything necessary for a comfortable and self-sufficient experience. Additionally, many properties come with refrigerators, ensuring guests can store food and drinks conveniently.
When is the best time to visit Chestertown for a vacation rental?
The best time to book a vacation rental in Chestertown is during the peak summer months of June to August, with July being the most popular. This vibrant season draws visitors seeking to enjoy the beautiful waterfront, explore charming historic sites, and indulge in local festivals that celebrate the town's rich culture. With comfortably warm temperatures averaging around 30°C, it's an ideal time for outdoor activities such as kayaking on the Chester River or strolling through the picturesque streets lined with boutique shops and cafes.

For those looking for a quieter experience, November presents a fantastic opportunity to appreciate the serene beauty of Chestertown. The autumn colours create a stunning backdrop for leisurely walks and scenic drives, allowing visitors to immerse themselves in the peaceful ambiance of the town. This off-peak month is also a great time to find more affordable rental options without compromising on quality.
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 enjoy a variety of attractions that highlight the town's rich history and scenic beauty. The historic district features charming historic architecture, with the Chestertown Tea Party Museum offering insights into the area's maritime heritage. The nearby Washington College, with its picturesque campus, often hosts events and exhibitions that are 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 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 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, Vrbo 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 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.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, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way.Vrbo 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.
Can I plan a group trip on Vrbo?
Vrbo'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 favorites, and build the perfect itinerary together.

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