Winchester Holiday Rentals from €143: Search Short-Term Rentals

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

LAKE HOUSE ON ROCKY FORK LAKE MOUNTAIN VIEW DR! : This holiday home rental outside of Winchester is located on a lake, and has a patio, a selection of games and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and an oven, so that you can cook with friends or family.

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Our top choices for Winchester holiday rentals

A two-story house with a front porch, a garage with two doors, and a small front yard with a flower decoration.

1. Quiet Farm Escape | Fishing, Nature & Views

Winchester

includes taxes & fees

14 Oct - 15 Oct

A cozy room with wooden walls, a ceiling fan, a window with a view of greenery, a lamp, and a chair with a deer pillow.

2. Deer Lodge (Secluded in Amish Country and peaceful)

Peebles

William B.

includes taxes & fees

14 Oct - 15 Oct

A cabin interior with a wooden dining table, chairs, a ceiling fan, a microwave, and an oven.

3. Griffis Game Hunting and/or Getaway

West Union

BRAD T.

includes taxes & fees

14 Oct - 15 Oct

A kitchen with wooden cabinets, a white refrigerator, a stove, and a microwave. There is a dining table with chairs and a small wooden stool.

4. Country Cabin in Amish Country

Peebles

Rodney C.

includes taxes & fees

1 Nov - 2 Nov

A small, single-story cabin with a porch, a front door, and a wreath decoration.

5. “Serenity Now” cozy 2BR country retreat in the heart of Amish Country and hiking

West Union

April V.

includes taxes & fees

22 Oct - 23 Oct

A cozy kitchen with wooden cabinets, a stove, and a refrigerator. There is a dining table with chairs and a window with blinds.

6. Hunter Lodge (Secluded in Amish Country and peaceful)

Peebles

kathy b.

includes taxes & fees

14 Oct - 15 Oct

A modern kitchen with a central island, bar stools, a hanging light fixture, and a fireplace.

7. Grain Bin - Unique Stay

Peebles

Jennifer J.

includes taxes & fees

14 Oct - 15 Oct

A wooden interior with a round dining table, chairs, a welcome sign, and a window with a view.

8. The Bear Den (Secluded in Amish Country and peaceful)

Peebles

Christy A.

includes taxes & fees

26 Oct - 27 Oct

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Top Winchester Hotel Reviews

French Quarter Inn

10/10 Excellent

"The staff was amazing! The area is so much fun to explore. The building was under construction, but it looked like it will be wonderful once completed. We will definitely be back."

McKeever Mansion-9,000 sq ft. Perfect for corporate, families, or special events

10/10 Excellent

"This place was awesome! We had a group of 43 and rented both the mansion and executive and it was perfect for our group. The place is beautiful, spacious and clean and Pamela is very responsive and kind. Her husband Michael and son Seth were doing some work around the property while we were there and we invited them for lunch and they were a joy to host (even tho they own the place lol). Michael even bought our group pickleball paddles for the local community pickleball courts. Would highly recommend!"

Nature's Nook Cabin

10/10 Excellent

"I really loved staying at this cute little cabin! The hot tub was an added bonus, and everything was so comfortable and homey when we arrived. It’s hidden away in the most beautiful little forest, and even though there is a road and houses nearby, it felt like we were a million miles from anywhere. It was so secluded and quiet."

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 €143 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

Can I find 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?

LAKE HOUSE ON ROCKY FORK LAKE MOUNTAIN VIEW DR!: This holiday home rental outside of Winchester is located on a lake, and has a patio, a selection of games and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and an oven, so that you can cook with friends or family.

What’s there to see and do in Winchester?

While you're exploring the area, Rocky Fork Lake and Ripley Lions Club Community Park are a couple of picturesque spots to get outside and enjoy nature. In the wider area, you’ll find Adams Lake State Park and Serpent Mound.

What’s a holiday rental in Winchester like?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Winchester. Holiday rentals feature amenities such as laundry facilities and kitchens so you'll feel just like you're staying in your own home. If you're concerned about a clean environment, holiday rentals can offer a sense of privacy away from public hotel lifts and lobbies packed with people while still allowing you the enjoyment of travel. You'll also find more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a popular option for families.

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Check prices for these dates

Our top choices for Winchester holiday rentals

1. Quiet Farm Escape | Fishing, Nature & Views