Accommodations, Farm stays, Cottages, Lodgings, Places to stay
Review score
1 reviews
AC, Barbecue, Crib, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry
Exceptional
18 reviews
Accommodations, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Places to stay, Family
Exceptional
2 reviews
Barbecue, Fireplace, Free Parking, Heater, Internet, Kitchen, Living Area, Microwave, No Smoking
Exceptional
53 reviews
Cheap, Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Places to stay, Family
Exceptional
2 reviews
Barbecue, Dryer, Fireplace, Free Parking, Heater, Kitchen, Laundry, Living Area, Microwave
Exceptional
43 reviews
Parking, Balcony/Terrace, Internet, Pet Friendly, Child Friendly
AC, Barbecue, Crib, Dryer, Fireplace, Free Parking, Heater, Kitchen, Laundry
Exceptional
2 reviews
Apartments, Accommodations, Parking, Lodgings, Places to stay, Family
AC, Barbecue, Free Parking, Heater, Kitchen, Microwave, No Smoking, Outdoor Space, TV
Accommodations, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Beach, Places to stay, Family
Fabulous
5 reviews
Barbecue, Free Parking, Heater, Internet, Kitchen, Living Area, Microwave, No Smoking, Patio
Exceptional
31 reviews
Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Places to stay
Balcony, Barbecue, Dryer, Fireplace, Free Parking, Heater, Kitchen, Living Area, Microwave
Good
1 reviews
Accommodations, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Beach, Places to stay, Beach rentals
AC, Arcade, Balcony, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet
Exceptional
16 reviews
Cheap, Accommodations, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Places to stay
Superb
2 reviews
AC, Barbecue, Dryer, Extra Bed, Free Parking, Heater, Internet, Kitchen, Laundry
Exceptional
13 reviews
Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Jacuzzis, Places to stay
Dryer, Free Parking, Heater, Kitchen, Laundry, Living Area, Microwave, No Smoking, Outdoor Space
Fabulous
35 reviews
AC, Barbecue, Free Parking, Internet, Kitchen, Living Area, Microwave, No Smoking, Outdoor Space
Exceptional
10 reviews
AC, Balcony, Barbecue, Dryer, Extra Bed, Free Parking, Heater, Internet, Kitchen
Very Good
46 reviews
AC, Arcade, Barbecue, Fireplace, Free Parking, Heater, Internet, Kitchen, Living Area
Fabulous
3 reviews
AC, Balcony, Extra Bed, Fireplace, Free Parking, Heater, Kitchen, Living Area, Microwave
Superb
6 reviews
AC, Arcade, Barbecue, Fireplace, Free Parking, Heater, Hot Tub, Internet, Kitchen
Exceptional
7 reviews
AC, Arcade, Barbecue, Fireplace, Free Parking, Heater, Internet, Kitchen, Living Area
Exceptional
12 reviews
AC, Arcade, Barbecue, Fireplace, Free Parking, Heater, Internet, Kitchen, Living Area
Exceptional
22 reviews
Pro Tip:
VacationByOwnerRentals aggregates the best inventory from leading travel sites, including Booking.com, Agoda.com, Expedia.com, Vrbo.com, and Airbnb.com. Use our Advanced Filters to compare verified homes, villas, cabins, condos, cottages, vacation rentals, hotels, and eco-friendly stays. Our goal is to help you find the absolute best Vacation Rentals in Chestertown.
VacationByOwnerRentals can help you find hotels, resorts, and rentals near many of 's top attractions, neighborhoods, and points of interest.
Some of the best vacation rentals in Chestertown are:
You can explore 159 verified vacation rentals in Chestertown. Our listings are sourced from a range of trusted providers, giving you access to a wide selection of private homes, apartments, and unique stays—all in one place.
Vacation rental prices in Chestertown vary depending on the season, property size, and location. Rates typically start from around $146 per night, with higher prices for larger homes or peak travel periods. Comparing available options can help you find a stay that matches both your budget and travel plans.
Most vacation rentals in Chestertown include fully equipped kitchens, making it easy to prepare meals and enjoy a more flexible stay. This is especially useful for families, longer stays, or travelers who prefer a home-like experience.
Yes, many vacation rentals in Chestertown welcome pets. Currently, 20 listings allow pets, although specific policies may vary by property. You can filter for pet-friendly options to quickly find suitable accommodations.
For popular travel periods such as holidays or peak seasons, it’s recommended to book your vacation rental 60 to 90 days in advance to secure the best options. During quieter times, you may still find good availability closer to your travel dates.
Vacation rentals in Chestertown often include amenities such as Fireplace/Heating, Internet, and Balcony/Terrace. These features provide added comfort and convenience, making them a popular choice for travelers seeking more space and privacy.
You can use filters to narrow down your search by criteria such as number of bedrooms, guest ratings, or specific amenities like private pools or beachfront access. This makes it easier to find a property that fits your exact needs and preferences.