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Winchester Vacation Rentals

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Check prices for these dates

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

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.
$348 nightly
The price is $358
Aug 9 - Aug 10
Total with taxes and fees
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.
$811 nightly
The price is $851
Aug 10 - Aug 11
Total with taxes and fees
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.
$218 nightly
The price is $226
Aug 31 - Sep 1
Total with taxes and fees
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.
$169 nightly
The price is $174
Aug 27 - Aug 28
Total with taxes and fees
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.
$151 nightly
The price is $155
Aug 9 - Aug 10
Total with taxes and fees
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)
"There were 3 of us ladies for the week. Lisa was a great host and recommendations were all perfect. We will definitely be back. Everything was clean and neat. We loved staying there. "
United States
Bonnie W.
$185 nightly
The price is $190
Aug 11 - Aug 12
Total with taxes and fees
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
9.8 out of 10, Exceptional, (6 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.
$406 nightly
The price is $415
Sep 1 - Sep 2
Total with taxes and fees
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.
$396 nightly
The price is $409
Aug 31 - Sep 1
Total with taxes and fees
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.
$234 nightly
The price is $240
Aug 11 - Aug 12
Total with taxes and fees
New Construction 3-bedroom townhome 3 queen beds with central AC and WiFi
Coffee/tea maker, fridge, microwave, oven

10. Cozy Pet Friendly House

Cozy Pet Friendly House
Wilmington
$181 nightly
The price is $187
Aug 24 - Aug 25
Total with taxes and fees
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
$224 nightly
The price is $233
Aug 7 - Aug 8
Total with taxes and fees
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.
$228 nightly
The price is $237
Aug 7 - Aug 8
Total with taxes and fees
Tiny Home Tranquil Oasis
Beach

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

Perfect for Groups! | Pool + Gym + Free Breakfast
Newark
$274 nightly
The price is $300
Aug 10 - Aug 11
Total with taxes and fees
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.
$285 nightly
The price is $296
Aug 9 - Aug 10
Total with taxes and fees
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.
$321 nightly
The price is $330
Aug 19 - Aug 20
Total with taxes and fees
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
$186 nightly
The price is $204
Aug 9 - Aug 10
Total with taxes and fees
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
$261 nightly
The price is $286
Aug 10 - Aug 11
Total with taxes and fees
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.
$366 nightly
The price is $366
Sep 1 - Sep 2
Total with taxes and fees
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.
$304 nightly
The price is $345
Aug 12 - Aug 13
Total with taxes and fees
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.
$246 nightly
The price is $279
Aug 10 - Aug 11
Total with taxes and fees
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

Sheraton Suites Wilmington Downtown

Sheraton Suites Wilmington Downtown

10/10 Excellent
"Amazing room. King suite is what I had. Very clean will definitely come back!"
michael 1-night trip
Posted 7 hours ago
Sheraton Suites Wilmington Downtown

Find out more about Winchester

Everything you need to know about Winchester vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Winchester vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Winchester vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Winchester vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Winchester. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Winchester in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $184 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Winchester rentals

At Expedia, we put the best Winchester vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Winchester rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Winchester vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Winchester. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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?

Sunset River Cottage: This vacation home rental near Winchester is located on a lake and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. It offers a garden, a selection of games, and a hot tub so you can immerse yourself in your vacation.

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. Christiana Mall and Meadow Park 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.