Chestertown Luxury Vacation Rentals
3 Mi To Washington College! Updated Home W/ Patio
- Cookware/ Kitchen utensils
- Free parking
- Express check-in/ -out
- Flat-screen TV
- Ironing facilities
- Terrace
Staying at the 3-bedroom 3 Mi To Washington College! Updated Home W/ Patio Chestertown, guests can visit Twigs & Teacups Gift Shop, which is about 10 minutes' drive away.
3 Mi To Washington College! Updated Home W/ Patio
- Cookware/ Kitchen utensils
- Free parking
- Express check-in/ -out
- Flat-screen TV
- Ironing facilities
- Terrace
3 Mi To Washington College! Updated Home W/ Patio
Staying at the 3-bedroom 3 Mi To Washington College! Updated Home W/ Patio Chestertown, guests can visit Twigs & Teacups Gift Shop, which is about 10 minutes' drive away.
Pet-Friendly Home On Chester River W/ Dock!
- Cookware/ Kitchen utensils
- Free parking
- Express check-in/ -out
- Flat-screen TV
- Ironing facilities
- Outdoor swimming pool
The 4-bedroom Pet-Friendly Home On Chester River W/ Dock! Chestertown is located 2.3 km from Twigs & Teacups Gift Shop and provides canyoning for active guests. The villa boasts a terrace and a patio, while Wilmer Park is about 10 minutes' drive away.
Pet-Friendly Home On Chester River W/ Dock!
- Cookware/ Kitchen utensils
- Free parking
- Express check-in/ -out
- Flat-screen TV
- Ironing facilities
- Outdoor swimming pool
Pet-Friendly Home On Chester River W/ Dock!
The 4-bedroom Pet-Friendly Home On Chester River W/ Dock! Chestertown is located 2.3 km from Twigs & Teacups Gift Shop and provides canyoning for active guests. The villa boasts a terrace and a patio, while Wilmer Park is about 10 minutes' drive away.
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Great deal
Walk To Historic Chestertown: Dog-Friendly Retreat
- Cookware/ Kitchen utensils
- Free parking
- Heating
Nestled just 11 minutes' walk from Twigs & Teacups Gift Shop, Walk To Historic Chestertown: Dog-Friendly Retreat villa entices guests to explore various tourist destinations nearby. With a maximum capacity of 6 guests, this 2-bedroom welcoming holiday home offers a car park.
Walk To Historic Chestertown: Dog-Friendly Retreat
- Cookware/ Kitchen utensils
- Free parking
- Heating
Walk To Historic Chestertown: Dog-Friendly Retreat
Nestled just 11 minutes' walk from Twigs & Teacups Gift Shop, Walk To Historic Chestertown: Dog-Friendly Retreat villa entices guests to explore various tourist destinations nearby. With a maximum capacity of 6 guests, this 2-bedroom welcoming holiday home offers a car park.
Cheap Vacation Rentals in Chestertown Maryland
Home Away
- Cookware/ Kitchen utensils
- Free parking
- VIP check-in/ -out
- Air conditioning
- Flat-screen TV
- Tea and coffee facilities
To enjoy your vacation in Hanover, stay at the 1-bedroom Home Away Hanover apartment, which is about 10 minutes by car from Orchid Gaming & Smoking Patio and 3.9 km from Jessup-Dorsey County Park. This spacious apartment can hold up to 2 guests.
Home Away
- Cookware/ Kitchen utensils
- Free parking
- VIP check-in/ -out
- Air conditioning
- Flat-screen TV
- Tea and coffee facilities
Home Away
To enjoy your vacation in Hanover, stay at the 1-bedroom Home Away Hanover apartment, which is about 10 minutes by car from Orchid Gaming & Smoking Patio and 3.9 km from Jessup-Dorsey County Park. This spacious apartment can hold up to 2 guests.
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Guest favorite
On Ensor
- Shared kitchen
- Free parking
- Air conditioning
- Flat-screen TV
- Mini-bar
- Ironing facilities
The 19th-century focused Peabody Research Library is approximately 25 minutes on foot from the 3-room On Ensor Apartment Baltimore, while Nazarene Baptist Church is situated nearby. Guests can make use of Wi-Fi for both business and leisure purposes.
On Ensor
- Shared kitchen
- Free parking
- Air conditioning
- Flat-screen TV
- Mini-bar
- Ironing facilities
On Ensor
The 19th-century focused Peabody Research Library is approximately 25 minutes on foot from the 3-room On Ensor Apartment Baltimore, while Nazarene Baptist Church is situated nearby. Guests can make use of Wi-Fi for both business and leisure purposes.
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Best-rated
Whispering Oak Mansion
- Free parking
- VIP check-in/ -out
- Air conditioning
- Flat-screen TV
- Sauna
- Terrace
Overlooking the garden, the 10-room Whispering Oak Mansion Apartment Bear is within 6 km of Hullabaloo Amusement Center in Bear. The homestay boasts a sauna and a foot bath offering a more peaceful experience.
Local sports activities include lawn tennis, ping-pong, and billiard.
Whispering Oak Mansion
- Free parking
- VIP check-in/ -out
- Air conditioning
- Flat-screen TV
- Sauna
- Terrace
Whispering Oak Mansion
Overlooking the garden, the 10-room Whispering Oak Mansion Apartment Bear is within 6 km of Hullabaloo Amusement Center in Bear. The homestay boasts a sauna and a foot bath offering a more peaceful experience.
Local sports activities include lawn tennis, ping-pong, and billiard.
Pet Friendly Vacation Rentals Chestertown Maryland
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Popular choice
Stylist Bedroom Central Of Baltimore
- Cookware/ Kitchen utensils
- Air conditioning
- Flat-screen TV
- Heating
Located 2.4 km from Baltimore - Penn railway station, the spacious Stylist Bedroom Central Of Baltimore apartment is merely a 7-minute walk from Little Italy. Wi-Fi and a car park are also available at the homestay.
Stylist Bedroom Central Of Baltimore
- Cookware/ Kitchen utensils
- Air conditioning
- Flat-screen TV
- Heating
Stylist Bedroom Central Of Baltimore
Located 2.4 km from Baltimore - Penn railway station, the spacious Stylist Bedroom Central Of Baltimore apartment is merely a 7-minute walk from Little Italy. Wi-Fi and a car park are also available at the homestay.
Gaia House
- Free parking
- VIP check-in/ -out
- Air conditioning
- Flat-screen TV
- Tea and coffee facilities
- Terrace
The 2-bedroom Gaia House Villa Annapolis is located within 5 minutes' walk of Capitol Church of Christ and provides guests with a terrace and a patio to ensure a memorable stay. Featuring a private parking lot, this Annapolis villa is located 2.8 km from Maryland Federation of Art.
Gaia House
- Free parking
- VIP check-in/ -out
- Air conditioning
- Flat-screen TV
- Tea and coffee facilities
- Terrace
Gaia House
The 2-bedroom Gaia House Villa Annapolis is located within 5 minutes' walk of Capitol Church of Christ and provides guests with a terrace and a patio to ensure a memorable stay. Featuring a private parking lot, this Annapolis villa is located 2.8 km from Maryland Federation of Art.
Cozy Room In Baltimore City
- Shared kitchen
- Free parking
- Security
- Air conditioning
- Flat-screen TV
- Leisure/ TV room
Cozy Room In Baltimore City offers proximity to such tourist attractions as Hilton Recreation Center, situated around 5 minutes' walk away. Wi-Fi and parking are also available at this homestay.
Cozy Room In Baltimore City
- Shared kitchen
- Free parking
- Security
- Air conditioning
- Flat-screen TV
- Leisure/ TV room
Cozy Room In Baltimore City
Cozy Room In Baltimore City offers proximity to such tourist attractions as Hilton Recreation Center, situated around 5 minutes' walk away. Wi-Fi and parking are also available at this homestay.
Chestertown Vacation Rentals Oceanfront
House On The Gwynns Falls
- Cookware/ Kitchen utensils
- Free parking
- 24-hour reception
- Air conditioning
- Golf centre
- Sun terrace
The 3-bedroom House On The Gwynns Falls Baltimore villa is situated only a few steps from Dickeyville and boasts yoga instruction for active guests. The Baltimore villa can host up to 2 guests and offers quick access to Dickey Memorial Presbyterian Church, located about a 5-minute stroll away.
A sun deck, a picnic area, and a golf course are available at House On The Gwynns Falls villa, while sport lovers can try hiking, lawn tennis, and cycling.
House On The Gwynns Falls
- Cookware/ Kitchen utensils
- Free parking
- 24-hour reception
- Air conditioning
- Golf centre
- Sun terrace
House On The Gwynns Falls
The 3-bedroom House On The Gwynns Falls Baltimore villa is situated only a few steps from Dickeyville and boasts yoga instruction for active guests. The Baltimore villa can host up to 2 guests and offers quick access to Dickey Memorial Presbyterian Church, located about a 5-minute stroll away.
A sun deck, a picnic area, and a golf course are available at House On The Gwynns Falls villa, while sport lovers can try hiking, lawn tennis, and cycling.
Watch Deer From A Farm Cottage
- Air conditioning
- Flat-screen TV
- Tea and coffee facilities
- Garden area
Situated about 7 km from Harford Artists Gallery, the 102 m² Watch Deer From A Farm Cottage Bel Air can host up to 6 guests in Bel Air. At the spacious 3-room apartment, Wi-Fi and a car park are also provided.
Watch Deer From A Farm Cottage
- Air conditioning
- Flat-screen TV
- Tea and coffee facilities
- Garden area
Watch Deer From A Farm Cottage
Situated about 7 km from Harford Artists Gallery, the 102 m² Watch Deer From A Farm Cottage Bel Air can host up to 6 guests in Bel Air. At the spacious 3-room apartment, Wi-Fi and a car park are also provided.
King Suite And Sofa Bed Fast Wi-Fi Easy Dc Access
- Cookware/ Kitchen utensils
- Free parking
- Air conditioning
- Flat-screen TV
- Ironing facilities
- Tea and coffee facilities
Situated 4.2 km from Suitland Bog Natural Area, the 56 m² King Suite And Sofa Bed Fast Wi-Fi Easy Dc Access District Heights can host up to 4 guests in District Heights. At this 1-bedroom apartment, Wi-Fi and parking are also provided.
King Suite And Sofa Bed Fast Wi-Fi Easy Dc Access
- Cookware/ Kitchen utensils
- Free parking
- Air conditioning
- Flat-screen TV
- Ironing facilities
- Tea and coffee facilities
King Suite And Sofa Bed Fast Wi-Fi Easy Dc Access
Situated 4.2 km from Suitland Bog Natural Area, the 56 m² King Suite And Sofa Bed Fast Wi-Fi Easy Dc Access District Heights can host up to 4 guests in District Heights. At this 1-bedroom apartment, Wi-Fi and parking are also provided.
Chestertown Vacation Rentals with Private Pool
Small House On Gentleman'S Farm
- Air conditioning
- Flat-screen TV
- Tea and coffee facilities
- Garden area
Located 6 km from Tudor Hall Museum, Small House On Gentleman'S Farm Bel Air villa gives access to various tourist sites in the vicinity. The 2-bedroom holiday home hosts up to 5 guests and provides them with parking.
Small House On Gentleman'S Farm
- Air conditioning
- Flat-screen TV
- Tea and coffee facilities
- Garden area
Small House On Gentleman'S Farm
Located 6 km from Tudor Hall Museum, Small House On Gentleman'S Farm Bel Air villa gives access to various tourist sites in the vicinity. The 2-bedroom holiday home hosts up to 5 guests and provides them with parking.
Baltimore Abode, Walk To Cross Street Market!
- Cookware/ Kitchen utensils
- Free parking
- 24-hour reception
- Air conditioning
- Entertainment
- Garden area
The 3-bedroom Baltimore Abode, Walk To Cross Street Market! villa offers quick access to such city attractions as Grace United Church of Christ, located approximately a 5-minute walk away. Providing guests with Wi-Fi and a car park, the property is merely 550 metres from Leadenhall Baptist Church.
Baltimore Abode, Walk To Cross Street Market!
- Cookware/ Kitchen utensils
- Free parking
- 24-hour reception
- Air conditioning
- Entertainment
- Garden area
Baltimore Abode, Walk To Cross Street Market!
The 3-bedroom Baltimore Abode, Walk To Cross Street Market! villa offers quick access to such city attractions as Grace United Church of Christ, located approximately a 5-minute walk away. Providing guests with Wi-Fi and a car park, the property is merely 550 metres from Leadenhall Baptist Church.
Pet-Friendly Delta Cabin W/ Private Hot Tub!
- Cookware/ Kitchen utensils
- Free parking
- Express check-in/ -out
- Ironing facilities
- Heating
- Jacuzzi
Offering a Jacuzzi, the welcoming Pet-Friendly Delta Cabin W/ Private Hot Tub! is located 3.4 km from Old Line Museum. With a maximum capacity of 4 guests, this 1-bedroom holiday home offers a car park.
Pet-Friendly Delta Cabin W/ Private Hot Tub!
- Cookware/ Kitchen utensils
- Free parking
- Express check-in/ -out
- Ironing facilities
- Heating
- Jacuzzi
Pet-Friendly Delta Cabin W/ Private Hot Tub!
Offering a Jacuzzi, the welcoming Pet-Friendly Delta Cabin W/ Private Hot Tub! is located 3.4 km from Old Line Museum. With a maximum capacity of 4 guests, this 1-bedroom holiday home offers a car park.
Luxury Apartment In Historic Carriage House
- Cookware/ Kitchen utensils
- Free parking
- Air conditioning
- Ironing facilities
- Tea and coffee facilities
- Heating
Episcopal Church of the Advent is only 0.6 km from the spacious 2-bedroom Luxury Apartment In Historic Carriage House Kennett Square, while Presbyterian Church of Kennett Square is situated nearby. This 93 m² apartment offers modern facilities, such as Wi-Fi and essentials like a car park for car travellers.
Luxury Apartment In Historic Carriage House
- Cookware/ Kitchen utensils
- Free parking
- Air conditioning
- Ironing facilities
- Tea and coffee facilities
- Heating
Luxury Apartment In Historic Carriage House
Episcopal Church of the Advent is only 0.6 km from the spacious 2-bedroom Luxury Apartment In Historic Carriage House Kennett Square, while Presbyterian Church of Kennett Square is situated nearby. This 93 m² apartment offers modern facilities, such as Wi-Fi and essentials like a car park for car travellers.
Are you in a hurry?
Here is a quick list of Vacation Rentals in Chestertown, selected based on their rating
| Name of hotel | Accommodation Rating | Price, $ | |
| Home Away |
9.7 / 10 (72 Reviews) |
From 76$ | |
| On Ensor |
8.9 / 10 (226 Reviews) |
From 80$ | |
| Whispering Oak Mansion |
8.9 / 10 (153 Reviews) |
From 157$ | |
| Stylist Bedroom Central Of Baltimore |
7.8 / 10 (406 Reviews) |
From 62$ | |
| Gaia House |
9.0 / 10 (57 Reviews) |
From 137$ |
Frequently Asked Questions
Which vacation rentals near downtown Chestertown offer great access to local attractions?
The Whispering Oak Mansion and House On The Gwynns Falls are both centrally located. They are walking distance to local shops and restaurants.
Explore the Chestertown Marina area before 11am for peaceful views and fewer crowds.
What vacation rentals near the historic district are good for exploring?
The Cozy Room In Baltimore City and Watch Deer From A Farm Cottage offer easy access to the historic district. You can enjoy local architecture and museums nearby.
Visit the historical sites in the morning to avoid crowds, particularly on weekends.
Are there romantic vacation rentals in Chestertown with a hot tub?
The Pet-Friendly Delta Cabin W/ Private Hot Tub! is a great choice for couples. It offers a relaxing atmosphere with stunning views.
Book during the off-peak season for lower prices and a quieter stay.
Which pet-friendly vacation rentals in Chestertown are close to the river?
The Pet-Friendly Home On Chester River W/ Dock! is perfect for those with dogs. It offers easy access to outdoor activities on the water.
Take your dog for a walk along the riverbank in the early morning when it's less busy.
Which vacation rentals have pools for families in Chestertown?
The Luxury Apartment In Historic Carriage House features a pool. It's a fun addition for families looking to cool off.
Visit the pool area after 4pm for a more relaxing experience when it's less crowded.
Which vacation rentals in Chestertown are best for extended stays?
Gaia House and King Suite And Sofa Bed Fast Wi-Fi Easy Dc Access are ideal for longer visits. They offer comfortable living spaces and essential amenities.
Consider rentals with kitchen facilities to make longer stays more convenient and economical.
What seasonal events should I expect in Chestertown?
The Chestertown Tea Party is a notable spring event featuring a parade and reenactments. It's a great way to experience local culture.
Arrive early for best parking options and to enjoy the food vendors before the crowds.
What are the best local places to eat near vacation rentals in Chestertown?
Try the Fish Whistle and Evergrain Bread Company for delicious local meals. Both are popular and offer a taste of regional cuisine.
Dinner during weekdays is usually less crowded and might feature special menu items.
How can I get around Chestertown easily during my stay?
Walking is often the best way to explore Chestertown. Many attractions are close together, making it easy to enjoy the scenery.
Bring comfortable shoes and plan your walking route to maximize your time.