Winter Park Villas - Vacation Rentals in Historical Society of Kent County Maryland
House
10.0
(
96 Reviews
)
3 Bedrooms
2 Bathrooms
10 Guests
-
Parking -
Spa -
Ocean View -
Balcony/Terrace
US $512
/Night
7 Nights - $3,585
Bed & Breakfast
9.6
(
19 Reviews
)
13 Bedrooms
13 Bathrooms
26 Guests
457.05 ft²
-
Breakfast -
Parking
-
Balcony/Terrace
-
View
US $359
/Night
7 Nights - $2,510
US $119
/Night
7 Nights - $833
House
10.0
(
90 Reviews
)
4 Bedrooms
2 Bathrooms
6 Guests
-
Parking
-
Balcony/Terrace
-
Kitchen -
Air Conditioner
US $387
/Night
7 Nights - $2,712
House
4 Bedrooms
5 Bathrooms
14 Guests
3229.17 ft²
-
Parking
-
Pool -
Balcony/Terrace
-
Internet
US $829
/Night
7 Nights - $5,803
Hotel
7.2
(
489 Reviews
)
-
Parking
-
Kitchen
-
Air Conditioner
-
Internet
US $80
/Night
7 Nights - $559
House
10.0
(
75 Reviews
)
5 Bedrooms
4 Bathrooms
10 Guests
-
Parking
-
Ocean View
-
Balcony/Terrace
-
View
US $481
/Night
7 Nights - $3,369
House
3 Bedrooms
1 Bathroom
6 Guests
1001.04 ft²
-
Parking
-
Balcony/Terrace
-
Internet
-
Security/Safety
US $285
/Night
7 Nights - $1,995
Apartment
10.0
(
57 Reviews
)
1 Bedroom
1 Bathroom
2 Guests
525 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $212
/Night
7 Nights - $1,482
Apartment
10.0
(
33 Reviews
)
2 Bedrooms
1 Bathroom
4 Guests
-
Parking
-
Kitchen
-
Air Conditioner
-
Internet
US $352
/Night
7 Nights - $2,465
House
10.0
(
31 Reviews
)
3 Bedrooms
2 Bathrooms
10 Guests
-
Oceanfront -
Hot Tub -
Parking
-
Ocean View
US $574
/Night
7 Nights - $4,015
House
10.0
(
31 Reviews
)
3 Bedrooms
2 Bathrooms
7 Guests
1440 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $289
/Night
7 Nights - $2,023
House
10.0
(
9 Reviews
)
2 Bedrooms
2 Bathrooms
6 Guests
967 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $265
/Night
7 Nights - $1,853
House
10.0
(
7 Reviews
)
3 Bedrooms
3 Bathrooms
8 Guests
-
Air Conditioner
-
Internet
-
Child Friendly -
Laundry
US $605
/Night
7 Nights - $4,237
House
10.0
(
7 Reviews
)
3 Bedrooms
3 Bathrooms
8 Guests
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $545
/Night
7 Nights - $3,814
Apartment
10.0
(
2 Reviews
)
2 Bedrooms
1 Bathroom
2 Guests
-
Parking
-
Kitchen
-
Air Conditioner
-
Internet
US $274
/Night
7 Nights - $1,918
Apartment
9.8
(
125 Reviews
)
1 Bedroom
1 Bathroom
3 Guests
-
Private Pool -
Parking
-
Pool
-
Ocean View
US $159
/Night
7 Nights - $1,112
House
9.8
(
25 Reviews
)
6 Bedrooms
6 Bathrooms
14 Guests
-
Hot Tub
-
Parking
-
Ocean View
-
Balcony/Terrace
US $1,659
/Night
7 Nights - $11,611
House
9.4
(
26 Reviews
)
4 Bedrooms
4 Bathrooms
14 Guests
3232 ft²
-
Private Pool
-
Parking
-
Pool
-
Balcony/Terrace
US $1,033
/Night
7 Nights - $7,232
House
7.4
(
3 Reviews
)
3 Bedrooms
1 Bathroom
6 Guests
1000 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $303
/Night
7 Nights - $2,118
House
3 Bedrooms
2 Bathrooms
10 Guests
-
Hot Tub
-
Parking
-
Ocean View
-
Balcony/Terrace
US $498
/Night
7 Nights - $3,485
New
House
1 Bedroom
1 Bathroom
4 Guests
1200 ft²
-
Oceanfront
-
Parking
-
Pool
-
Ocean View
US $323
/Night
7 Nights - $2,263
House
10.0
(
116 Reviews
)
4 Bedrooms
3 Bathrooms
8 Guests
2100 ft²
-
Hot Tub
-
Parking
-
Balcony/Terrace
-
View
US $542
/Night
7 Nights - $3,792
House
9.8
(
24 Reviews
)
4 Bedrooms
2 Bathrooms
8 Guests
-
Hot Tub
-
Parking
-
Balcony/Terrace
-
Kitchen
US $608
/Night
7 Nights - $4,259
★ Pro Tip: Winterparkvillas makes it easy to compare the best listings on Winterparkvillas homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Winterparkvillas homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Historical Society of Kent County Maryland.
Weather in Historical Society of Kent County Maryland
View the weather forecast for Historical Society of Kent County Maryland before booking your Historical Society of Kent County Maryland Vacation Rentals to confirm your best time to go.
December - February
High 56°F Low 33°F
March - May
High 73°F Low 38°F
June - August
High 90°F Low 69°F
September - November
High 80°F Low 42°F
Historical Society of Kent County Maryland Vacation Rental Frequently Asked Questions
What are the top vacation rentals in Historical Society of Kent County Maryland?
There are a lot of options in Historical Society of Kent County Maryland. If you plan on staying in the Historical Society of Kent County Maryland area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Historical Society of Kent County Maryland:
- Waterfront w/Deepwater Pier Walking Distance to Downtown Chestertown
- Private Waterfront Paradise w/Pier - Kayak to Historic Chestertown!
- Circa 1900 Home in the Heart of Historic Downtown Chestertown
- Wren Retweet- Country Estate in Center of C’Town
- Historic Downtown Garden Oasis with Private Patio
- Breathtaking waterfront home on the Chester River
- Newly restored apartment in the heart of Chestertown
- Harbor View Haven | Waterfront w/Hot Tub + Dock!
- Lovely Home in Chestertown - Free EV Charging for guests
- Walk to Historic Chestertown: Dog-Friendly Retreat
How many vacation rentals are available in Historical Society of Kent County Maryland?
Currently, the total number of properties listed in 2026 is over 48 in the Historical Society of Kent County Maryland area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Historical Society of Kent County Maryland.
