Holiday Rentals in Winchester

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Holiday Rentals in Winchester

Cabin in Chesapeake City

9.0 out of 10, Wonderful, (18)
"This place was very cute and clean, also convenient to Shaefers Marina. It was a perfect place for us to spend a weekend on the bay. "
United States
Benay N.
The price is €247
includes taxes & fees
29 Nov - 30 Nov
Historic Chesapeake City Stay

Apartment in Elkton

9.8 out of 10, Exceptional, (40)
"Perfect in every way… a great stay"
United States
Robert B.
The price is €100
includes taxes & fees
3 Dec - 4 Dec
Country Get Away 1 Bedroom Apartment

Holiday Home in Elkton

9.6 out of 10, Exceptional, (5)
"The owners were very attentive to our needs, and everything was exactly as advertised. We came up for a horse show in Maryland and the convenience to the grounds was exceptional, and everything was wonderful from the privacy to the beauty of the property."
United States
Rees L.
The price is €140
includes taxes & fees
1 Dec - 2 Dec
Summer Rustic Camping with AC and King Bed

Cottage in Port Deposit

10.0 out of 10, Exceptional, (11)
"Very clean, spacious, comfortable house. Would stay there again. Great communication with the hosts."
United States
Courtney W.
The price is €188
includes taxes & fees
30 Nov - 1 Dec
Quarry Landing - Center of Town & River View - 3 Bedroom

Holiday Home in Kennett Square

9.8 out of 10, Exceptional, (28)
"Great property. Good for dogs, full fenced in yard. "
United States
David R.
The price is €254
includes taxes & fees
30 Nov - 1 Dec
Underground Railroad Barn

Apartment in Kennett Square

10.0 out of 10, Exceptional, (11)
"Loved the property, had everything we needed and more.Plush towels, comfortable bed, wonderful environment filled with really cool art. "
United States
Valerie H.
The price is €147
includes taxes & fees
26 Dec - 27 Dec
Welcome to the Mushroom Capital of the World!

Holiday Home in Elkton

10.0 out of 10, Exceptional, (1)
"The house was clean and a nice place. The kitchen was nice. "
United States
Anthony C.
The price is €301
includes taxes & fees
29 Nov - 30 Nov
Family-Friendly 4BR Home in Elkton - AC, High-Speed WiFi & Relaxing Vibes

Cottage in Lincoln University

10.0 out of 10, Exceptional, (16)
"Our stay was perfect! We had a wonderful time with family celebrating our daughter's UD graduation."
United States
Heidi Z.
The price is €421
includes taxes & fees
1 Dec - 2 Dec
Thunder Hill Retreat - Spacious/Deck/Hot tub

Apartment in Bear

9.6 out of 10, Exceptional, (4)
"Second time staying in as many weeks. Place is spot on for what we needed for our quick trips. Close to food and shopping as well as easy access to highways if needed."
United States
Jeffrey R.
The price is €96
includes taxes & fees
30 Nov - 1 Dec
Cozy loft above ink shop

Cottage in Kennett Square

10.0 out of 10, Exceptional, (37)
"I love the open space and excellent kitchen. The location is walking distance to all Kennett Square has to offer. The host is kind and helpful."
United States
Laura D.
The price is €392
includes taxes & fees
3 Dec - 4 Dec
Charming Carriage House in the Heart of Kennett

Apartment in Elkton

2.0 star property
9.8 out of 10, Exceptional, (6)
"Great stay. Everything you need, quiet and clean. "
United States
Melissa J.
The price is €143
includes taxes & fees
8 Dec - 9 Dec
Cozy studio in charming Elkton with AC and WiFi included. 3 miles from Fair Hill

Holiday Home in Downtown Wilmington

9.4 out of 10, Exceptional, (11)
"Great little spot in a perfect location for us"
United States
j m.
The price is €252
includes taxes & fees
1 Dec - 2 Dec
Private townhouse near downtown and state park

Cottage in Port Deposit

10.0 out of 10, Exceptional, (30)
"Wow such a wonderful place, clean, warm, and full of everything you need."
United States
Oswaldo S.
The price is €187
includes taxes & fees
30 Nov - 1 Dec
Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland.

Apartment in Wilmington

2.0 star property
8.0 out of 10, Very good, (3)
"This unit is very much as depicted in photos on VRBO site. The neighborhood is interesting and feels safe, and the unit itself is very authentic to residential multi units built, I'm guessing, about 100 years ago. We recommend this place. "
United States
Thomas D.
The price is €319
includes taxes & fees
30 Nov - 1 Dec
The Gilpin Getaway | 2BR | Free Coffee | by RedAwning

Holiday Home in Elkton

8.0 out of 10, Very good, (9)
"Nice and quiet place to stay"
United States
Gary M.
The price is €248
includes taxes & fees
30 Nov - 1 Dec
Charming 3-bedroom house with WiFi, AC in peaceful Elk Neck

Holiday Home in Kennett Square

9.8 out of 10, Exceptional, (22)
"Very nice and clean! "
United States
Virginie M.
Underground Railroad 4 Bedroom Farmhouse

Apartment in Wilmington

3.0 star property
6.0 out of 10, (1)
"Be aware that there is on street parking that requires a permit from the city of Wilmington. Red Awni ng worked with me to resolve the issue but it took some time and a few texts to make it work.The on street parking placed me a block and half from the propery. No cost but need proof of renting the space. The GPS sent you down a one way street that does not bring by the front of the property. This was a problem finding the property after dark. No climate control of the rental unit. The bed was...
United States
Clifford
The price is €247
includes taxes & fees
11 Dec - 12 Dec
Trolley Teacup Charming Cozy Studio 1 Bedroom Apts by RedAwning

Holiday Home in Kennett Square

8.0 out of 10, Very good, (15)
"Great location with character! Host was friendly and communicated well."
United States
Ross G.
The price is €441
includes taxes & fees
8 Dec - 9 Dec
Kennett Square, Near Longwood Gardens & Downtown

Apartment in Newark

2.0 star property
10.0 out of 10, Exceptional, (3)
"Enjoyed our stay."
United States
Erik H.
The price is €262
includes taxes & fees
9 Dec - 10 Dec
Private Home + 3 Bed/1.5 Bath + 2MI - University of Delaware

Holiday Home in Elkton

2.0 star property
The price is €119
includes taxes & fees
1 Dec - 2 Dec
Room #3 in Elkton, MD – Easy Access to I-95
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

Find out more about Winchester

Everything you need to know about Winchester holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Winchester holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Winchester holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Winchester holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Winchester holiday rentals we have selected for you start as low as €112 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Winchester rentals

At Expedia, we put the best Winchester holiday 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 holiday.

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 holiday rentals in Winchester?

Yes, there are holiday rentals close to the most popular sights in Winchester, or you can select a more secluded option if you're looking for a relaxing stay.

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

Upper Chesapeake Bay 5 bedroom, 3 bath, Hot Tub, Waterfront: This holiday home rental outside of Winchester is located on a river, and has a patio, a garden and a BBQ to put you at ease in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a selection of games and 1 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. University of Delaware and University of Delaware Botanic Gardens are a couple of places you'll find in the wider area.

What are holiday rentals like in Winchester?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Winchester. Holiday rentals feature extras like kitchens and laundry facilities so you'll have everything you want. If you're concerned about a sanitised environment, holiday rentals can provide a sense of safety away from public hotel lifts and busy front desks while still allowing you to travel. You'll also get more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a popular choice for a small group gathering.