All Vacation Rentals Chestertown
Chestertown
2 guests

Adults:

2

Children:

0

Child’s age:

Chestertown

Nov 12 - Nov 13 ·
2 guests

Chestertown Vacation Rentals

Chestertown
2 guests

Adults:

2

Children:

0

Child’s age:

Over 5 stays assessed to highlight the standout picks

Navigation

1. 3 Mi To Washington College! Updated Home W/ Patio

2. Pet-Friendly Home On Chester River W/ Dock!

3. Walk To Historic Chestertown: Dog-Friendly Retreat

4. Home Away

Cheap Vacation Rentals in Chestertown Maryland

5. On Ensor

6. Whispering Oak Mansion

7. Stylist Bedroom Central Of Baltimore

Pet Friendly Vacation Rentals Chestertown Maryland

8. Gaia House

9. Cozy Room In Baltimore City

10. House On The Gwynns Falls

Chestertown Luxury Vacation Rentals

3 Mi To Washington College! Updated Home W/ Patio 3 Mi To Washington College! Updated Home W/ Patio

3 Mi To Washington College! Updated Home W/ Patio

7413 Poplar Ave
3.2 km (2.0 mi) from city center
93
  • 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.

10
1 reviews

3 Mi To Washington College! Updated Home W/ Patio

3.2 km (2.0 mi) from city center
93
  • 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.

10
1 reviews
Pet-Friendly Home On Chester River W/ Dock! Pet-Friendly Home On Chester River W/ Dock!

Pet-Friendly Home On Chester River W/ Dock!

205 Fey Rd
1.3 km (0.8 mi) from city center
300
  • 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.

~ US$793 / night

Pet-Friendly Home On Chester River W/ Dock!

1.3 km (0.8 mi) from city center
300
  • 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.

From US$ 793 / night
  • Great deal
Walk To Historic Chestertown: Dog-Friendly Retreat Walk To Historic Chestertown: Dog-Friendly Retreat

Walk To Historic Chestertown: Dog-Friendly Retreat

709 High St
0.8 km (0.5 mi) from city center
90
  • 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

0.8 km (0.5 mi) from city center
90
  • 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.

Vacation rentals near Chestertown

Cheap Vacation Rentals in Chestertown Maryland

Home Away Home Away

Home Away

7916 Mine Run Road
60.1 km (37.3 mi) from Chestertown
70
  • 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.

9.7
72 reviews
~ US$76 / night

Home Away

60.1 km (37.3 mi) from Chestertown
70
  • 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.

9.7
72 reviews
From US$ 76 / night
  • Guest favorite
On Ensor On Ensor

On Ensor

1309 Ensor Street
47.5 km (29.5 mi) from Chestertown
  • 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.

8.9
226 reviews
~ US$80 / night

On Ensor

47.5 km (29.5 mi) from Chestertown
  • 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.

8.9
226 reviews
From US$ 80 / night
  • Best-rated
Whispering Oak Mansion Whispering Oak Mansion

Whispering Oak Mansion

3805 Kirkwood Saint Georges Road
51.2 km (31.8 mi) from Chestertown
  • 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.

8.9
153 reviews
~ US$157 / night

Whispering Oak Mansion

51.2 km (31.8 mi) from Chestertown
  • 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.

8.9
153 reviews
From US$ 157 / night

Pet Friendly Vacation Rentals Chestertown Maryland

  • Popular choice
Stylist Bedroom Central Of Baltimore Stylist Bedroom Central Of Baltimore

Stylist Bedroom Central Of Baltimore

137 South Central Avenue
46.7 km (29.0 mi) from Chestertown
28
  • 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.

7.8
406 reviews
~ US$62 / night

Stylist Bedroom Central Of Baltimore

46.7 km (29.0 mi) from Chestertown
28
  • 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.

7.8
406 reviews
From US$ 62 / night
Gaia House Gaia House

Gaia House

102 Louis Drive
47.3 km (29.4 mi) from Chestertown
9
  • 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.

9
57 reviews
~ US$137 / night

Gaia House

47.3 km (29.4 mi) from Chestertown
9
  • 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.

9
57 reviews
From US$ 137 / night
Cozy Room In Baltimore City Cozy Room In Baltimore City

Cozy Room In Baltimore City

41 North Ellamont Street
52.7 km (32.7 mi) from Chestertown
6
  • 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.

8.8
51 reviews
~ US$58 / night

Cozy Room In Baltimore City

52.7 km (32.7 mi) from Chestertown
6
  • 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.

8.8
51 reviews
From US$ 58 / night

Chestertown Vacation Rentals Oceanfront

House On The Gwynns Falls House On The Gwynns Falls

House On The Gwynns Falls

5017 Wetheredsville Rd
56.0 km (34.8 mi) from Chestertown
167
  • 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.

9.2
27 reviews
~ US$194 / night

House On The Gwynns Falls

56.0 km (34.8 mi) from Chestertown
167
  • 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.

9.2
27 reviews
From US$ 194 / night
Watch Deer From A Farm Cottage Watch Deer From A Farm Cottage

Watch Deer From A Farm Cottage

715 Cedar Lane
38.1 km (23.7 mi) from Chestertown
102
  • 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.

10
13 reviews
~ US$262 / night

Watch Deer From A Farm Cottage

38.1 km (23.7 mi) from Chestertown
102
  • 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.

10
13 reviews
From US$ 262 / night
King Suite And Sofa Bed Fast Wi-Fi Easy Dc Access King Suite And Sofa Bed Fast Wi-Fi Easy Dc Access

King Suite And Sofa Bed Fast Wi-Fi Easy Dc Access

1705 Berry Ln
79.3 km (49.3 mi) from Chestertown
56
  • 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.

9.2
32 reviews
~ US$77 / night

King Suite And Sofa Bed Fast Wi-Fi Easy Dc Access

79.3 km (49.3 mi) from Chestertown
56
  • 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.

9.2
32 reviews
From US$ 77 / night

Chestertown Vacation Rentals with Private Pool

Small House On Gentleman'S Farm Small House On Gentleman'S Farm

Small House On Gentleman'S Farm

711 Cedar Lane
38.2 km (23.7 mi) from Chestertown
84
  • 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.

10
6 reviews
~ US$205 / night

Small House On Gentleman'S Farm

38.2 km (23.7 mi) from Chestertown
84
  • 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.

10
6 reviews
From US$ 205 / night
Baltimore Abode, Walk To Cross Street Market! Baltimore Abode, Walk To Cross Street Market!

Baltimore Abode, Walk To Cross Street Market!

1332 South Hanover Street
47.8 km (29.7 mi) from Chestertown
195
  • 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.

9.4
38 reviews
~ US$400 / night

Baltimore Abode, Walk To Cross Street Market!

47.8 km (29.7 mi) from Chestertown
195
  • 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.

9.4
38 reviews
From US$ 400 / night
Pet-Friendly Delta Cabin W/ Private Hot Tub! Pet-Friendly Delta Cabin W/ Private Hot Tub!

Pet-Friendly Delta Cabin W/ Private Hot Tub!

252 Mccall Rd
65.1 km (40.5 mi) from Chestertown
93
  • 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.

10
3 reviews
~ US$152 / night

Pet-Friendly Delta Cabin W/ Private Hot Tub!

65.1 km (40.5 mi) from Chestertown
93
  • 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.

10
3 reviews
From US$ 152 / night
Luxury Apartment In Historic Carriage House Luxury Apartment In Historic Carriage House

Luxury Apartment In Historic Carriage House

226 Maiden Lane
77.2 km (48.0 mi) from Chestertown
93
  • 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.

9.8
11 reviews
~ US$252 / night

Luxury Apartment In Historic Carriage House

77.2 km (48.0 mi) from Chestertown
93
  • 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.

9.8
11 reviews
From US$ 252 / night

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.

Tip:

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.

Tip:

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.

Tip:

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.

Tip:

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.

Tip:

Visit the pool area after 4pm for a more relaxing experience when it's less crowded.

Are there affordable vacation rentals for families in Chestertown?

Home Away and On Ensor are budget-friendly options great for families. They have ample space and a kitchen for cooking meals.

Tip:

Plan to eat breakfast at the rental to save on dining costs during your stay.

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.

Tip:

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.

Tip:

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.

Tip:

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.

Tip:

Bring comfortable shoes and plan your walking route to maximize your time.

Location