Winchester Holiday Rentals from AU$301: Search Short-Term Rentals

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

Sailor's Sunrise Cottage - Chesapeake Bay : This holiday home rental outside of Winchester is located on a lake, and has a fireplace, a garden and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a fridge, a stovetop and a microwave, so that you can cook with friends or family. Kick off your shoes and enjoy yourself with a selection of games and 1 hot tub.

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Our top choices for Winchester holiday rentals

A modern kitchen with dark cabinets, a stainless steel refrigerator, and a wooden floor.

1. Family-Friendly 4BR Home in Elkton - AC, High-Speed WiFi & Relaxing Vibes

Elkton

Shana G.

includes taxes & fees

20 Oct - 21 Oct

A residential house with a brick exterior, a dark roof, and a front porch with a bench.

2. Cozy studio in charming Elkton with AC and WiFi included. 3 miles from Fair Hill

Elkton

Melissa J.

includes taxes & fees

18 Oct - 19 Oct

A compact kitchen with dark cabinets, a stainless steel refrigerator, a microwave, and a stove.

3. Cozy 1-bedroom apartment in Lincoln University

Lincoln University

Zachary Z.

includes taxes & fees

15 Oct - 16 Oct

A wooden cabin with a porch, surrounded by dense forest.

4. Country Get Away Studio Apartment

Elkton

JAMES V.

includes taxes & fees

27 Oct - 28 Oct

A riverside dock with boats, a covered seating area, and a bridge in the background.

5. Historic Chesapeake City Stay

Chesapeake City

Martha J.

includes taxes & fees

15 Oct - 16 Oct

A patio with a table and chairs, an umbrella, and a view of a grassy yard and trees.

6. Amish Countryside Escape at Forest Edge Farm

Nottingham

jckglss6 G.

includes taxes & fees

9 Nov - 10 Nov

A two-story house with a deck, a barbecue grill, and a covered patio area.

7. Thunder Hill Retreat - Spacious/Deck/Hot tub

Lincoln University

Arthur B.

includes taxes & fees

19 Oct - 20 Oct

A covered outdoor seating area with a fire pit, wicker furniture, and a Netflix sign.

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

Newark

Erik H.

includes taxes & fees

3 Nov - 4 Nov

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Top Winchester Hotel Reviews

Great Wolf Lodge Perryville

10/10 Excellent

"Just come and relax"

Sonesta Select Newark Christiana Mall

8/10 Good

"The hotel has obviously been newly refurbished. The rooms are spacious, well appointed, clean, and well designed. They had a small continental breakfast with coffee, juices, and pastries which was a nice touch and the staff said that they are planning to have a breakfast with more options in the coming weeks. The lobby and breakfast area were really nice. Beds were comfortable, but pillows were the basic small, square pillows that most hotels have decided to go with these days. Our "ding" for this property is that the doors seem to be having issues (we really had to push to get our room door to open both entering and exiting.) Staff said that because they are new, the seals are extra stiff so hopefully this is something that will improve over time. Overall, this is one of the nicer hotels in this area, and we would stay here again if in the area."

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, 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 favourite 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 depend 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 AU$301 per night. Entering your travel dates in the search wizard might find you 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?

Sailor's Sunrise Cottage - Chesapeake Bay: This holiday home rental outside of Winchester is located on a lake, and has a fireplace, a garden and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a fridge, a stovetop and a microwave, so that you can cook with friends or family. Kick off your shoes and enjoy yourself 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.

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Check prices for these dates

Our top choices for Winchester holiday rentals

1. Family-Friendly 4BR Home in Elkton - AC, High-Speed WiFi & Relaxing Vibes

2. Cozy studio in charming Elkton with AC and WiFi included. 3 miles from Fair Hill

3. Cozy 1-bedroom apartment in Lincoln University

4. Country Get Away Studio Apartment

5. Historic Chesapeake City Stay

6. Amish Countryside Escape at Forest Edge Farm

7. Thunder Hill Retreat - Spacious/Deck/Hot tub

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

9. Woodland Retreat at Fair Hill- Hot Tub, Pool, and Sport Court

10. Winery & Vineyard Loft with 1000+ acres of hiking. Farm with Goats & Horses

11. Charming Water-Front Cottage Perfectly Suited for Rest, Relaxation, and Leisure

12. 5-bedroom vacation home 5 minutes from historic Charlestown

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

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

15. Luxury Bed and Breakfast for a Weekend Getaway near Susquehanna State Park, Maryland

16. Kennett Square, Near Longwood Gardens & Downtown

17. Nature's Haven Tiny Home

18. Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland.

19. Tiny Home Tranquil Oasis

20. Private 3 room Queen Suite w/Kitchenette

Find holiday rentals that suit your style

Top Winchester Hotel Reviews

Great Wolf Lodge Perryville

Sonesta Select Newark Christiana Mall

Sheraton Suites Wilmington Downtown

Travel Inn

Ramada by Wyndham Newark/Wilmington

Find out more about Winchester

Frequently asked questions

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