Photo by Assya A

Chestertown holiday lettings

We found 61 holiday rentals — enter your dates for availability

Discover a selection of 25 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.

Holiday rentals with weekly discounts - Chestertown

Showing deals for:7 Nov - 14 Nov

Image gallery for Beautiful, spacious waterfront home, an easy walk to historic Chestertown

Exterior
9.8 out of 10 rating
Exceptional
(22 reviews)

Beautiful, spacious waterfront home, an easy walk to historic Chestertown

Chestertown, MD

8% off
Price is £6,735
£962 per night
includes taxes & fees
Beautiful, spacious waterfront home, an easy walk to historic Chestertown

Find spaces that suit your style

  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Find out more about Chestertown

Find out more about Chestertown

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 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)
  • Cassinelli Winery and Vineyards (7.1 mi / 11.3 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 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)
  • 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)
  • Rocky Point Park and Beach (18.1 mi / 29.2 km)
  • Belcamp Beach (19.2 mi / 30.9 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 an excellent choice. This charming area is known for its well-preserved historic architecture and vibrant atmosphere. Staying here places you within walking distance of top attractions such as the Chestertown Tea Party Festival and the Kent County Arts Council, both of which showcase the town's rich history and cultural offerings. The Historic District is dotted with quaint shops, inviting cafés, and lovely gardens, making it a delightful area to explore.

Another appealing option is the waterfront area along the Chester River. This picturesque setting offers beautiful views and a relaxed vibe, superb for those looking to unwind by the water. You can easily access the Chestertown Marina and enjoy activities like kayaking or simply strolling along the riverside. This neighbourhood typically features a variety of rental properties, allowing visitors to choose from quaint cottages to larger homes, suiting different tastes and group sizes.
How much does it cost to rent a holiday home in Chestertown?
Prices for holiday 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 holiday 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, travellers should consider the serene surroundings of the Chester River, which offers picturesque views and a tranquil atmosphere. The area near the public landing provides access to the water, where you can find charming rental properties featuring amenities such as private docks, outdoor seating areas, and fully equipped kitchens, great for enjoying leisurely family meals or entertaining guests.

Additionally, the historic district of Chestertown offers a selection of homes that combine modern comforts with classic architecture. These properties often come with spacious gardens, fireplaces, and proximity to local shops and eateries, allowing guests to immerse themselves in the quaint, small-town vibe. Visitors can explore the nearby waterfront parks, which are ideal for picnics and leisurely strolls along the riverside.
What is the most popular type of holiday rental accomodation in Chestertown?
In Chestertown, holiday houses are the most common type of rental accommodation, with about 24 available throughout the charming town. These properties typically feature multiple bedrooms, fully equipped kitchens, and inviting living spaces, making them suitable for families or groups seeking a comfortable stay. Many also offer outdoor areas, such as patios or gardens, superb for relaxing after a day of exploring local attractions like the historic downtown area and the picturesque waterfront.
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 near the scenic Chester River, offers a delightful mix of history and outdoor activities, making it an excellent choice for families.

Visitors can find spacious homes that often come equipped with full kitchens, allowing for the preparation of family meals, and comfortable living areas where everyone can gather. Many properties also feature outdoor spaces, great for children to play, as well as amenities like Wi-Fi and air conditioning for added comfort during your stay.
Can I rent a holiday home with a pool or hot tub in Chestertown?
In Chestertown, Maryland, there are several holiday homes available for rent that feature pools and hot tubs. This charming town along the Chester River provides a picturesque setting for a relaxing getaway. Many of these rentals can be found in residential areas that offer tranquility while still being close to the town's historical attractions and vibrant local culture.
Can I find long-stay holiday rentals in Chestertown?
A long-stay holiday 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, with about 14 options to choose from. The charming historic district of Chestertown features properties that often come with modern amenities such as fully equipped kitchens, spacious living areas, and outdoor spaces, making them ideal for families or groups travelling with pets.
Are there any remote work holiday rentals in Chestertown?
In Chestertown, Maryland, there are a variety of remote work holiday rentals available, with around 31 options to choose from. This charming town offers a unique blend of historic charm and modern conveniences, making it an ideal spot for those looking to work remotely while enjoying a scenic environment. Many of the properties come equipped with dedicated workspaces, including desks and comfortable chairs, as well as high-speed Wi-Fi to ensure a productive experience. Some rentals also feature additional amenities such as computer monitors and safes for added convenience and security. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Chestertown holiday rentals with parking?
Vrbo offers a wide selection of holiday 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 holiday 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 holiday rental?
July is the most popular time to visit Chestertown, Maryland, as it falls within the peak season from June to August. During these months, visitors flock to this charming town to enjoy a variety of outdoor activities and local events. The warm summer temperatures, often reaching the low 30s Celsius, create a superb setting for exploring the picturesque waterfront, indulging in local cuisine, and participating in community festivals.

Chestertown's vibrant atmosphere during July is complemented by numerous activities, including kayaking on the Chester River and strolling through the historic district, where you'll find beautifully preserved 18th-century buildings. The town's lively events, such as the annual Chestertown Tea Party Festival, draw crowds and offer a taste of local culture.

If you're seeking a more budget-friendly option, consider planning your visit in November. This month showcases the stunning autumn scenery, with the leaves turning vibrant shades of orange and gold. The quieter streets allow for leisurely exploration of local shops and galleries, and the fall weather is still quite pleasant for outdoor strolls.
How early should I book a Chestertown holiday rental?
Book your Chestertown holiday 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 holiday 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 charming waterfront. The historic district features beautifully preserved 18th-century buildings, and a stroll along High Street will reveal quaint shops, galleries, and cafes. The Chestertown Tea Party Festival celebrates the town's revolutionary history, while the nearby Washington College offers cultural events and art exhibitions.
Can I change or cancel my Chestertown home rental booking on Vrbo?
To find Chestertown holiday 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 flat or a countryside retreat, you can turn your space into a standout destination—become a host and let Vrbo handle the heavy lifting to help you thrive.
Are all fees included in the Chestertown holiday 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.

More Holiday Rentals ideas

Olney Holiday Rentals
Standard Link for Olney
Lusby Holiday Rentals
Standard Link for Lusby
Tilghman Holiday Rentals
Standard Link for Tilghman
Ocean City Holiday Rentals
Standard Link for Ocean City
St. Michaels Holiday Rentals
Standard Link for St. Michaels
Key West Holiday Rentals
Standard Link for Key West
Hagerstown Holiday Rentals
Standard Link for Hagerstown
Sarasota Holiday Rentals
Standard Link for Sarasota
San Diego Holiday Rentals
Standard Link for San Diego
Davenport Holiday Rentals
Standard Link for Davenport
Gambrills Holiday Rentals
Standard Link for Gambrills
Adamstown Holiday Rentals
Standard Link for Adamstown
North East Holiday Rentals
Standard Link for North East
Salisbury Holiday Rentals
Standard Link for Salisbury
Destin Holiday Rentals
Standard Link for Destin
Crumpton Auction Holiday Rentals
Standard Link for Crumpton Auction
Taylors Island Holiday Rentals
Standard Link for Taylors Island
Stowe Holiday Rentals
Standard Link for Stowe
Naples Holiday Rentals
Standard Link for Naples
Annapolis Holiday Rentals
Standard Link for Annapolis
Chesapeake Beach Holiday Rentals
Standard Link for Chesapeake Beach
Rockville Holiday Rentals
Standard Link for Rockville
Berlin Holiday Rentals
Standard Link for Berlin
Severna Park Holiday Rentals
Standard Link for Severna Park
Gaithersburg Holiday Rentals
Standard Link for Gaithersburg
Friendsville Holiday Rentals
Standard Link for Friendsville
Palm Springs Holiday Rentals
Standard Link for Palm Springs
McHenry Holiday Rentals
Standard Link for McHenry

People also search for

Rockville Apartments
Standard Link for Rockville
Gatlinburg Cabin Rentals
Standard Link for Gatlinburg