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Winchester Vacation Rentals

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Check prices for these dates

In two weeks
21 Aug - 23 Aug
In two months
2 Oct - 4 Oct
In three months
30 Oct - 1 Nov
In four months
27 Nov - 29 Nov

Our top choices for Winchester vacation rentals

Coffee/tea maker, fridge, microwave, oven

1. Two-story condo in luxury townhouse. Free parking.

Two-story condo in luxury townhouse. Free parking.
Downtown Wilmington
9.6 out of 10, Exceptional, (19 reviews)
"Comfortable place, wonderful amenities, and a gracious host. "
United States
Donald H.
The price is SAR 811
SAR 1,343 total
includes taxes & fees
10 Aug - 11 Aug
Two-story condo in luxury townhouse. Free parking.
Coffee/tea maker, fridge, microwave, oven

2. Entire two-unit four-story townhouse, for multi-family vacations; free parking

Entire two-unit four-story townhouse, for multi-family vacations; free parking
Downtown Wilmington
9.6 out of 10, Exceptional, (11 reviews)
"Good place to stay, well kept, spacious and updated. "
United States
Kevin L.
The price is SAR 2,078
SAR 3,208 total
includes taxes & fees
12 Aug - 13 Aug
Entire two-unit four-story townhouse, for multi-family vacations; free parking
Exterior detail

3. Modern Downtown 1BR | Free Garage Parking + Workspace

Modern Downtown 1BR | Free Garage Parking + Workspace
Downtown Wilmington
7.4 out of 10, Good, (3 reviews)
"We were in town for a wedding at Hotel DuPont. The proximity to the hotel was amazing! The apartment was cozy and clean. Felt very safe and loved that you needed a code just to enter the main door at the entrance to the building. The host was great and responded quickly to any questions. Having free parking was also a huge plus!! Definitely recommend and would stay again if ever in town."
United States
Aileen R.
The price is SAR 395
SAR 864 total
includes taxes & fees
1 Sep - 2 Sep
Modern Downtown 1BR | Free Garage Parking + Workspace
Exterior detail

4. Modern 1BR in Downtown Wilmington Near Riverwalk & Restaurants

Modern 1BR in Downtown Wilmington Near Riverwalk & Restaurants
Downtown Wilmington
10.0 out of 10, Exceptional, (1 review)
"Beautiful apartment with great dining choices not too far away. The host was very communicative. Will be coming back for sure!"
United States
Galen A.
The price is SAR 406
SAR 653 total
includes taxes & fees
27 Aug - 28 Aug
Modern 1BR in Downtown Wilmington Near Riverwalk & Restaurants
Property grounds

5. Entire place with private parking

Entire place with private parking
Hilltop
8.0 out of 10, Very Good, (11 reviews)
"great place very clean. Will stay again loved private parking "
United States
kennya J.
The price is SAR 360
SAR 583 total
includes taxes & fees
11 Aug - 12 Aug
Entire place with private parking
Property grounds

6. New Construction townhome close to everything downtown w/transparent pricing

New Construction townhome close to everything downtown w/transparent pricing
Hilltop
9.6 out of 10, Exceptional, (29 reviews)
"We love this townhouse, close to everything!"
United States
Judy P.
The price is SAR 422
SAR 712 total
includes taxes & fees
11 Aug - 12 Aug
New Construction townhome close to everything downtown w/transparent pricing
Smart TV, fireplace, DVD player, books

7. Harmony Family Estate A Beautiful 5-bedroom house in Wilmington for your group

Harmony Family Estate A Beautiful 5-bedroom house in Wilmington for your group
Wilmington
9.0 out of 10, Wonderful, (7 reviews)
"We very much enjoyed resting in the house between our activities. The kids loved the large room for watching a soccer match. The dining area is exceptionally nice for kids."
United States
Emily M.
The price is SAR 777
SAR 1,548 total
includes taxes & fees
7 Sep - 8 Sep
Harmony Family Estate A Beautiful 5-bedroom house in Wilmington for your group
Exterior

8. Elegant Family Stay • Quiet Neighborhood • Comfort

Elegant Family Stay • Quiet Neighborhood • Comfort
New Castle
10.0 out of 10, Exceptional, (12 reviews)
"Beautiful well kept property with lots of room to relax."
United States
Daniel J.
The price is SAR 1,200
SAR 1,618 total
includes taxes & fees
18 Aug - 19 Aug
Elegant Family Stay • Quiet Neighborhood • Comfort
Interior

9. New Construction 3-bedroom townhome 3 queen beds with central AC and WiFi

New Construction 3-bedroom townhome 3 queen beds with central AC and WiFi
Hilltop
10.0 out of 10, Exceptional, (1 review)
"If you are visiting the Chase fieldhouse for an event it is 10 minutes driving which is very convenient. The host was very accommodating for what me and my family needed. There was enough space for 5 of us to sleep comfortable."
United States
Alexis O.
The price is SAR 544
SAR 903 total
includes taxes & fees
11 Aug - 12 Aug
New Construction 3-bedroom townhome 3 queen beds with central AC and WiFi
TV, books, stereo

10. Cozy Pet Friendly House

Cozy Pet Friendly House
Wilmington
The price is SAR 558
SAR 699 total
includes taxes & fees
12 Aug - 13 Aug
Cozy Pet Friendly House
Terrace/patio

11. Nature's Haven Tiny Home

Nature's Haven Tiny Home
Bear
10.0 out of 10, Exceptional, (4 reviews)
"Great place to relax after a while on the go. Karin was very friendly and informative about places to see in the area. Everything was great "
United States
Maxwell
The price is SAR 710
SAR 881 total
includes taxes & fees
10 Aug - 11 Aug
Nature's Haven Tiny Home
Terrace/patio

12. Tiny Home Tranquil Oasis

Tiny Home Tranquil Oasis
Bear
10.0 out of 10, Exceptional, (2 reviews)
"This was a stop over on our way to the beach- it was a convenient comfy space for our family."
United States
Erin C.
The price is SAR 710
SAR 903 total
includes taxes & fees
10 Aug - 11 Aug
Tiny Home Tranquil Oasis
Beach

13. Perfect for Groups! | Pool + Gym + Free Breakfast

Perfect for Groups! | Pool + Gym + Free Breakfast
Newark
The price is SAR 895
SAR 1,134 total
includes taxes & fees
12 Aug - 13 Aug
Perfect for Groups! | Pool + Gym + Free Breakfast
Interior

14. Come stay on our 40 Viking yacht - two bedrooms with restaurant and biking trail

Come stay on our 40 Viking yacht - two bedrooms with restaurant and biking trail
Bear
10.0 out of 10, Exceptional, (2 reviews)
"Great stay. Awesome owner. Nice restaurant right up the ramp. Would def recommend and do again if in the area!!!"
United States
Justin M.
The price is SAR 939
SAR 1,116 total
includes taxes & fees
12 Aug - 13 Aug
Come stay on our 40 Viking yacht - two bedrooms with restaurant and biking trail
Dining

15. Serene Townhome minutes away from Christiana Mall, DE Race Park and Univ. of DE

Serene Townhome minutes away from Christiana Mall, DE Race Park and Univ. of DE
Newark
9.6 out of 10, Exceptional, (24 reviews)
"Very nice property, just right size for our needs. Great neighborhood. Kitchen very nice, check in easy."
United States
Lori W.
The price is SAR 730
SAR 1,240 total
includes taxes & fees
19 Aug - 20 Aug
Serene Townhome minutes away from Christiana Mall, DE Race Park and Univ. of DE
Beach

16. Free Breakfast. Outdoor Pool. 10 Min from University of Delaware!

Free Breakfast. Outdoor Pool. 10 Min from University of Delaware!
Newark
The price is SAR 611
SAR 768 total
includes taxes & fees
12 Aug - 13 Aug
Free Breakfast. Outdoor Pool. 10 Min from University of Delaware!
Beach

17. Free Breakfast. Pool. 10 Min Drive to the University of Delaware!

Free Breakfast. Pool. 10 Min Drive to the University of Delaware!
Newark
The price is SAR 857
SAR 1,075 total
includes taxes & fees
12 Aug - 13 Aug
Free Breakfast. Pool. 10 Min Drive to the University of Delaware!
Terrace/patio

18. Private Home + 3 Bed/1.5 Bath + 2MI - University of Delaware

Private Home + 3 Bed/1.5 Bath + 2MI - University of Delaware
Newark
9.8 out of 10, Exceptional, (6 reviews)
"Enjoyed our stay."
United States
Erik H.
The price is SAR 535
SAR 1,324 total
includes taxes & fees
8 Sep - 9 Sep
Private Home + 3 Bed/1.5 Bath + 2MI - University of Delaware
Coffee/tea maker, fridge, microwave, oven

19. Underground Railroad 4 Bedroom Farmhouse

Underground Railroad 4 Bedroom Farmhouse
Kennett Square
10.0 out of 10, Exceptional, (34 reviews)
"Comfortable, clean, thoughtfully stocked property. We would definitely stay again!"
United States
Amy Y.
The price is SAR 713
SAR 1,489 total
includes taxes & fees
23 Aug - 24 Aug
Underground Railroad 4 Bedroom Farmhouse
Interior

20. Underground Railroad Barn

Underground Railroad Barn
Kennett Square
9.8 out of 10, Exceptional, (38 reviews)
"Very cool place! "
United States
Scott M.
The price is SAR 372
SAR 1,049 total
includes taxes & fees
10 Aug - 11 Aug
Underground Railroad Barn
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Winchester Hotel Reviews

Best Western Plus Newark/Christiana Inn

Best Western Plus Newark/Christiana Inn

10/10 Excellent
"Everybody was very professional. Excellent job"
James 1-night trip
Posted less than an hour ago
Best Western Plus Newark/Christiana Inn

Frequently asked questions

Are there vacation rentals in Winchester?

Yes, you can find vacation rentals near top local attractions in Winchester, or you can go with a secluded option if you're looking for a relaxing stay.

What are some of the best vacation rentals that Winchester has to offer?

*** NEWLY RENOVATED**** Escape to a Beautiful Getaway on the Chesapeake Bay: This vacation home near Winchester is located on a lake and has a patio, a garden, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a hot tub.

What can I see and do in Winchester?

While exploring the area, visit family-friendly sights like Fred Rust Ice Arena, or get outside and enjoy nature at Fair Hill State Natural Resources Management Area. Fair Hill Equestrian Center and University of Delaware are a couple of places you'll find in the larger area.

What are vacation rentals like in Winchester?

Vacation rentals are private accommodations you can stay in for several days or longer in Winchester. Vacation rentals feature amenities like kitchens and laundry facilities so you'll have a home away from home. If you're concerned about a clean environment, vacation rentals can offer a sense of privacy away from public hotel elevators and lobbies packed with people while still allowing you the enjoyment of travel. You'll also have more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a popular option for a small group gathering.