Winchester Holiday Rentals

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Holiday Rentals in Winchester

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

Winchester
10.0 out of 10, Exceptional, (275)
"Check-in was easy and convenient. Kitchen was well stocked had everything we needed. The cabin was beautiful and clean."
United States
Gail M.
Rustic Cabin with modern amenities and 1 acre stocked Fishing Lake !

Ohio Starlight Glamping Cabins

2.0 star property
Rome
10.0 out of 10, Exceptional, (1)
"This place is awesome. "
United States
Zacheryah
Ohio Starlight Glamping Cabins

Bear Necessities Cabin - What Else Do You Need?

West Union
10.0 out of 10, Exceptional, (7)
"Great little spot! Cabin is super nice inside and out."
United States
Jason M.
The price is AU$250
includes taxes & fees
18 Nov - 19 Nov
Bear Necessities Cabin - What Else Do You Need?

Unique stay, hot tub, secluded

Peebles
9.2 out of 10, Wonderful, (17)
"This is an amazing property and we will be returning because it was so luxurious."
United States
Amy
The price is AU$396
includes taxes & fees
18 Nov - 19 Nov
Unique stay, hot tub, secluded

Cowboy Saloon Cabin

Hamersville
9.6 out of 10, Exceptional, (17)
"Cute, cozy, and clean. Stayed 2 nights; enjoyed fishing off the back deck. "
United States
Cynthia C.
The price is AU$308
includes taxes & fees
18 Nov - 19 Nov
Cowboy Saloon Cabin

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

Williamsburg
10.0 out of 10, Exceptional, (42)
"Host is helpful and check in/out was a breeze!"
United States
Emily G.
McKeever Mansion-9,000 sq ft. Perfect for corporate, families, or special events

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

Blue Creek
10.0 out of 10, Exceptional, (338)
"Beautifully done!"
United States
Shauna H.
Get away from it all! Restored 1800 log cabin on 40 acres - NO cleaning fee!

Griffis Game Hunting and/or Getaway

West Union
9.8 out of 10, Exceptional, (27)
"We really enjoyed staying here. The weather was very nice. The cabin is very cozy and enough room for a few. Thank you Jennifer and Brian for sharing your beautiful place! I’ll definitely be going back!"
United States
BRADLEY T.
The price is AU$343
includes taxes & fees
24 Nov - 25 Nov
Griffis Game Hunting and/or Getaway

Secluded cabin located in Amish country

West Union
10.0 out of 10, Exceptional, (93)
"Great location. Secluded, but still within 15 or 20 minutes of everything you need. The cabin was exceptionally clean and well maintained. We had a wonderful time disconnecting and recharging here. Thank you for your hospitality Frank!"
United States
Kelly A.
Secluded cabin located in Amish country

Peaceful cabin with spectacular river and scenic views.

Adams County
9.8 out of 10, Exceptional, (27)
"Cozy cabin with a great view"
United States
Beth S.
The price is AU$562
includes taxes & fees
18 Nov - 19 Nov
Peaceful cabin with spectacular river and scenic views.

Sunset Cabin-Couple's only Hot Tub Getaway

Hillsboro
9.6 out of 10, Exceptional, (5)
Sunset Cabin-Couple's only Hot Tub Getaway

Flash Lodge Add-on Cabin-Pamela's Diamond

Hamersville
9.4 out of 10, Exceptional, (26)
"Perfect for a couple or just one person as amenities were nice and convenient. We had the lodge and added the cabin for additional room "
United States
Tom S.
The price is AU$232
includes taxes & fees
18 Nov - 19 Nov
Flash Lodge Add-on Cabin-Pamela's Diamond

Nature's Nook Cabin

Hillsboro
9.8 out of 10, Exceptional, (80)
"Cozy little place for 2"
United States
Christopher Z.
Nature's Nook Cabin

Glamping Cabin | Huge Window | Over a Creek

Green Township
9.8 out of 10, Exceptional, (7)
"Beautiful location ."
United States
Shelly R.
The price is AU$177
includes taxes & fees
20 Nov - 21 Nov
Glamping Cabin | Huge Window | Over a Creek

Glamping Cabin | Huge Window | Cliff and Animal Views

Green Township
10.0 out of 10, Exceptional, (1)
"We had a lovely time at this cabin -- I stayed with my sweetheart and our doberman puppy, and the place was quiet, rustic, beautiful. I would be happy to come back here again. Our dog met goats for the first time! That was hilarious and unexpected. There's a beautiful horse on the property, and we had a nice time giving him scritches on the neck. The price was lovely for the accommodation, and the huge window looking out on the wooded cliff was a wonderful bonus. Thank you!"
United States
Olga
The price is AU$177
includes taxes & fees
18 Nov - 19 Nov
Glamping Cabin | Huge Window | Cliff and Animal Views

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

Blue Creek
10.0 out of 10, Exceptional, (109)
"We have been here before and it is always wonderful! If you need to get off the grid and sneak away to peaceful then this is your place!! Did I mention CLEAN! Enjoy! "
United States
Lisa S.
Peaceful historic log cabin getaway on 40 acres - NO cleaning fee!

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

Peebles
10.0 out of 10, Exceptional, (33)
"The house was as good as advertised. Everything was clean and ready to go when we arrived. Plenty of room for everyone, and tons of amenities. "
United States
Nick B.
Peaceful 8 Bedroom 5 Bath w/patio bar-grill and swimming pond

The Angler

Hillsboro
9.8 out of 10, Exceptional, (7)
"Very enjoyable weekend. Very peaceful cute little place "
United States
Angie C.
The price is AU$198
includes taxes & fees
9 Dec - 10 Dec
The Angler

Sleepy Hollow Large 4 Bedroom Lakefront House in Rocky Fork Lake

2.0 star property
Hillsboro
Sleepy Hollow Large 4 Bedroom Lakefront House in Rocky Fork Lake

Hunter Lodge (Secluded in Amish Country and peaceful)

Peebles
10.0 out of 10, Exceptional, (40)
"The cabin was perfect for our short stay."
United States
Beth R.
The price is AU$319
includes taxes & fees
18 Nov - 19 Nov
Hunter Lodge (Secluded in Amish Country and peaceful)
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, 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$177 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 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.