Winchester Holiday Rentals

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Holiday Rentals in Winchester

Rustic Cabin with modern amenities and 1 acre stocked Fishing Lake !

10.0 out of 10, Exceptional, (273)
"Great get away for few days. Cabin well stocked with everything you needed."
Rustic Cabin with modern amenities and 1 acre stocked Fishing Lake !

Cozy private getaway built for couples to reconnect !!

10.0 out of 10, Exceptional, (47)
"Beautiful home, quiet surroundings, awesome stay, loved this place."
Cozy private getaway built for couples to reconnect !!

Get away from it all! Restored 1800 log cabin on 40 acres - NO cleaning fee!

10.0 out of 10, Exceptional, (333)
"Peaceful and beautiful. The cabin feels like home so comfortable And clean. If you want a quiet place away from the city this is a great place. "
Get away from it all! Restored 1800 log cabin on 40 acres - NO cleaning fee!

Peaceful cabin with spectacular river and scenic views.

9.8 out of 10, Exceptional, (21)
"Cozy cabin with a great view"
The price is AU$562
includes taxes & fees
29 Sept - 30 Sept
Peaceful cabin with spectacular river and scenic views.

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

9.8 out of 10, Exceptional, (40)
"Host is helpful and check in/out was a breeze!"
McKeever Mansion-9,000 sq ft. Perfect for corporate, families, or special events

Home away from Home! - 1BR apartment in Maysville

10.0 out of 10, Exceptional, (8)
"Wonderful apartment. Will book again next time we come to visit our family."
The price is AU$167
includes taxes & fees
7 Oct - 8 Oct
Home away from Home! - 1BR apartment in Maysville

Secluded cabin located in Amish country

10.0 out of 10, Exceptional, (89)
"Great place to getaway from it all! "
Secluded cabin located in Amish country

Unique stay, hot tub, secluded

9.4 out of 10, Exceptional, (13)
"We really enjoyed our stay! "
The price is AU$396
includes taxes & fees
29 Sept - 30 Sept
Unique stay, hot tub, secluded

Private cabin on 80 acre farm in Adams County Ohio

10.0 out of 10, Exceptional, (19)
"Beautiful cabin and property. Very peaceful and quiet."
Private cabin on 80 acre farm in Adams County Ohio

Cozy newly remodeled camper with hot tub and fire pit close to hiking/kayaking

10.0 out of 10, Exceptional, (39)
"Close to Serpent Mound. Relaxing and peaceful. "
Cozy newly remodeled camper with hot tub and fire pit close to hiking/kayaking

Peaceful historic log cabin getaway on 40 acres - NO cleaning fee!

10.0 out of 10, Exceptional, (107)
"Great place to get away. "
Peaceful historic log cabin getaway on 40 acres - NO cleaning fee!

Peaceful 8 Bedroom 5 Bath w/patio bar-grill and swimming pond

10.0 out of 10, Exceptional, (29)
"The place was huge, clean, and amazing! Would recommend to anyone! "
Peaceful 8 Bedroom 5 Bath w/patio bar-grill and swimming pond

Hunter Lodge (Secluded in Amish Country and peaceful)

10.0 out of 10, Exceptional, (39)
"Booked this place for my son and daughter in law for their honeymoon. He is in the Navy so he only had availability to go away for one night before he had to get back to his duty station. They really enjoyed the property and surrounding area. "
The price is AU$289
includes taxes & fees
29 Sept - 30 Sept
Hunter Lodge (Secluded in Amish Country and peaceful)

The Angler

9.8 out of 10, Exceptional, (7)
"The cabin was clean and the beds/pillows were very comfortable! It was perfect for our overnight stay. It was close to Serpent Mound which was the point of our visit.If fishing is your thing, this cabin is perfect! It’s right across the road from the marina and the check in area is in a bait shop.The owners were very friendly and helpful.The owners did a good job updating this cabin. It was apparent that there had been termites in the past from some damage to the walls, but the issue was...
The Angler

Glamping Cabin | Huge Window | Over a Creek

10.0 out of 10, Exceptional, (6)
"Beautiful location ."
The price is AU$177
includes taxes & fees
29 Sept - 30 Sept
Glamping Cabin | Huge Window | Over a Creek

Griffis Game Hunting and/or Getaway

9.8 out of 10, Exceptional, (27)
"Awesome cabin. Super clean and fun!"
The price is AU$338
includes taxes & fees
29 Sept - 30 Sept
Griffis Game Hunting and/or Getaway

Glamping Cabin | Huge Window | Tree House Feel

9.2 out of 10, Wonderful, (18)
"The perfect place to connect with nature and enjoy a beautiful landscape the attention was great the beautiful place the super comfortable cabin I would come back again"
The price is AU$177
includes taxes & fees
29 Sept - 30 Sept
Glamping Cabin | Huge Window | Tree House Feel

Secluded in Amish Country and peaceful

9.6 out of 10, Exceptional, (22)
"Nice clean quiet place to stay, would stay there again if in the area."
The price is AU$280
includes taxes & fees
29 Sept - 30 Sept
Secluded in Amish Country and peaceful

Secluded 3-Level Home! Luxury & Tranquility on 8 Acres Bordering Brush Creek!

9.8 out of 10, Exceptional, (142)
"The Sanctuary is our family go to place when we want to reconnect and relax. This was our 4th visit and it has always been clean, comfortable and has a well stocked kitchen for your cooking needs."
Secluded 3-Level Home! Luxury & Tranquility on 8 Acres Bordering Brush Creek!

Cowboy Saloon Cabin

9.4 out of 10, Exceptional, (16)
"The utensils were dirty, a lot of bugs, spider webs. I think the porch's should of been swept off and just cleaned a little better. Windows were dirty. Inside cabin was very nice and clean, except for the utensils. We will definately visit again. Thank you. Lianne"
The price is AU$301
includes taxes & fees
29 Sept - 30 Sept
Cowboy Saloon Cabin
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

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$167 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

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?

McKeever Mansion-9,000 sq ft. Perfect for corporate, families, or special events: This holiday home rental outside of Winchester comes with laundry facilities so that you can feel at home during your trip. Kitchen amenities such as a dishwasher and a stovetop can make your holiday run smoothly.

What’s there to see and do in Winchester?

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

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.