Choose from 19 vacation rentals located in Chestertown, Maryland. Top filters in Chestertown include Air conditioner, Internet / Wifi, and Laundry. Prices range from $72 to $1,113 per night. Our most popular vacation rental types near Chestertown are Hotel and RV.

Top vacation rentals in Chestertown

Relaxation by the Chester River
5.0
Outstanding(80 Reviews)
House
 in Chestertown
Waterfront w/Deepwater Pier Walking Distance to Downtown Chestertown
8 guests · 4 bedrooms · 3 baths
Garden · Kitchen / Kitchenette · Air conditioner

Looking for the perfect place to call home during your trip to Chestertown? This House offers a comfort and style with top-notch amenities, including Air conditioner, Dishwasher and Fireplace, and more.

$$$$
vrbo logo
View deal
Property view
3.8
Good(250 Reviews)
Hotel
 in Chestertown
2star
Comfort Inn & Suites Chestertown
Pets allowed · Kitchen / Kitchenette · Air conditioner

Looking for a memorable stay in Chestertown? Our Hotel might just be what you're looking for. Enjoy amenities including Air conditioner, Internet / Wifi and Laundry, and more during your stay.

$$$$
booking logo
View deal
Property view
Motel
 in Chestertown
Driftwood Inn
Pets allowed · Kitchen / Kitchenette · Air conditioner

This inviting Motel in Chestertown can fit your needs for many types of vacations, at $73 per night.

$$$$
booking logo
View deal
Garden bridge
5.0
Outstanding(63 Reviews)
House
 in Chestertown
Country Estate in Historic District
10 guests · 5 bedrooms · 4 baths
Garden · Pets allowed · Kitchen / Kitchenette

This inviting House in Chestertown can fit your needs for many types of vacations, at $232 per night.

$$$$
vrbo logo
View deal

Search by property type

Search by amenity

Vacation rentals with air conditioning in Chestertown

Front door
4.8
Outstanding(24 Reviews)
House
 in Chestertown
Victorian Hideaway: Beautiful Exterior, Modern interior
8 guests · 4 bedrooms · 3 baths
Garden · Kitchen / Kitchenette · Air conditioner

Looking for a business stay, family stay, couples stay, getaway vacation, or traveling to Chestertown, at $667 per night for your next great vacation.

$$$$
vrbo logo
View deal
Property grounds
5.0
Outstanding(19 Reviews)
House
 in Chestertown
Beautiful, spacious waterfront home, an easy walk to historic Chestertown
14 guests · 6 bedrooms · 7 baths
Garden · Kitchen / Kitchenette · Air conditioner

This House for $1,113 in Chestertown, is perfect for your next (business stay, family stay, couples stay, getaway vacation, etc.)

$$$$
vrbo logo
View deal
Welcome to Pier Pleasure!
4.8
Outstanding(22 Reviews)
House
 in Chestertown
Private pier and pool at this waterfront Chestertown home
14 guests · 5 bedrooms · 5 baths
Garden · Pool · Pets allowed

House in Chestertown, for $834 per night is great for your next (business stay, family stays, couples stay, getaway vacation, etc.)

$$$$
vrbo logo
View deal
Property view
Hotel
 in Chestertown
2star
Red Roof Inn & Suites Chestertown
Air conditioner · Internet / Wifi · Parking

Experience the best of Chestertown with this Hotel available for $150. This property is equipped with amenities including Air conditioner, Fireplace and Internet / Wifi, and more.

$$$$
priceline logo
View deal
city photo
Chestertown

Chestertown travel guide

Let us help you plan your perfect Chestertown vacation. Our travel guide highlights things to do, places to see, favorite vacation rental amenities in Chestertown, and more.

Frequently asked questions

What is the price range for rentals in Chestertown?

Vacation rentals in Chestertown have a price range between $72-$1,113. The average price for rentals in Chestertown is $232 per night.

What are the top things to do in Chestertown, MD?

Chestertown, MD is a charming town with plenty of activities to explore. Here are the top four things to do in Chestertown, MD:

  • Visit the historic sites such as the Chester River Association and the Chestertown Tea Party Museum.
  • Take a leisurely stroll along the waterfront promenade.
  • Explore the shops and restaurants in downtown Chestertown.
  • Attend a performance at the Garfield Center for the Arts.

No matter what you choose to do, Chestertown, MD is sure to provide a memorable experience!

What are the most popular vacation rental amenities in Chestertown, MD?

The most popular vacation rental amenities in Chestertown, MD are:

  • Fully equipped kitchens
  • Outdoor space, such as patios, decks, and gardens
  • High-speed internet access
  • Air conditioning
  • Laundry facilities

These amenities provide vacationers with the comforts of home, while allowing them to enjoy the beauty of Chestertown and its surrounding areas.

Where is Chestertown, MD?

Chestertown, MD is a small town located on the Eastern Shore of Maryland. It is situated on the Chester River and is home to Washington College, a small liberal arts college. With its historic downtown, beautiful waterfront, and small-town charm, Chestertown is a great place to visit or live.

What are the best neighborhoods to visit in Chestertown, MD?

The best neighborhoods to visit in Chestertown, MD are:

  • High Street Historic District
  • Washington College
  • Fountain Park

High Street Historic District is a charming neighborhood with plenty of shops and restaurants to explore. Washington College is a great place to visit for its scenic views and historical significance. Fountain Park is a great spot to relax and take a break from the hustle and bustle of the city.

What are the popular shopping destinations in Chestertown, MD?

The popular shopping destinations in Chestertown, MD include:

  • The Bookplate
  • The Little Bookshop
  • Chestertown Natural Foods Co-Op
  • The Imperial Theater

From books to theater performances, Chestertown has something for everyone!

Is Chestertown, MD safe to travel to?

Chestertown, MD is generally a safe place to travel to. Here are a few safety tips to keep in mind:

  • Stay aware of your surroundings
  • Keep your valuables secure
  • Avoid walking alone at night

What is the culture like in Chestertown, MD?

Chestertown, Maryland is a small town located on the Eastern Shore of Maryland. It is known for its diverse culture, and for its friendly, welcoming atmosphere. Here are five aspects of the culture in Chestertown:

  • The town is known for its art scene, with many galleries, studios, and performing arts venues.
  • Chestertown is home to Washington College, which brings in a diverse student population.
  • Chestertown also has a vibrant music scene, with many live music venues and events.
  • The town has a strong sense of community, and many local businesses and organizations.
  • The town is also known for its historic architecture, with many buildings dating back to the 18th century.

Where can I find affordable accommodation in Chestertown, MD?

For affordable accommodation in Chestertown, MD, consider the Comfort Inn & Suites. This hotel offers a convenient location near the historic downtown area, with easy access to popular attractions and activities. It also features a range of amenities and services, including:

  • Free Wi-Fi
  • Complimentary hot breakfast
  • Fitness center
  • Indoor pool

How can I get around in Chestertown, MD?

You can get around Chestertown, MD by:

  • Walking
  • Biking
  • Public Transportation

Chestertown also has taxi services and multiple ride sharing options such as Uber and Lyft.

What are the must-visit tourist attractions in Chestertown, MD?

Chestertown, MD is a small town with a lot of charm and many must-visit tourist attractions! Here are some of the top attractions in the area:

  • Washington College
  • Historic Main Street
  • The Garfield Center for the Arts
  • Worton Creek Marina

Whether you're looking for a relaxing stroll down Main Street or a fun day out on the water, Chestertown has something for everyone! Be sure to check out these must-visit attractions when you visit.

What do I need to know before visiting Chestertown, MD?

Before visiting Chestertown, MD, there are a few things to keep in mind:

  • It is a small town, so be prepared for slower-paced activities.
  • The town is located on the banks of the Chester River, so there are plenty of outdoor activities to enjoy.
  • The town is home to many historical landmarks, so bring your camera!

Additionally, Chestertown is known for its vibrant arts and culture scene. There are several galleries, theaters, and museums to explore. Be sure to check out the Saturday morning farmers market for some local produce and goods!

What are the most popular vacation rental amenities in Chestertown?

  • Air conditioner
  • Internet / Wifi
  • Laundry

Explore near Chestertown

Rentals near top attractions

Related vacation destinations

Nearby vacation destinations

Travel inspiration

Keep exploring