Holiday Rentals in Winchester

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Holiday Rentals in Winchester

Cabin in 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 €102
includes taxes & fees
30 Nov - 1 Dec
Glamping Cabin | Huge Window | Cliff and Animal Views

Cabin in Green Township

9.8 out of 10, Exceptional, (7)
"Beautiful location ."
United States
Shelly R.
The price is €102
includes taxes & fees
7 Dec - 8 Dec
Glamping Cabin | Huge Window | Over a Creek

Apartment in Maysville

10.0 out of 10, Exceptional, (13)
"Amazing stay. We would definitely recommend this place to anyone!"
United States
John H.
The price is €96
includes taxes & fees
13 Dec - 14 Dec
Home away from Home! - 1BR apartment in Maysville

Cabin in Green Township

10.0 out of 10, Exceptional, (1)
The price is €138
includes taxes & fees
1 Dec - 2 Dec
Sleeps 4| Private Bathroom | Stunning Views

Cabin in Green Township

9.0 out of 10, Wonderful, (19)
"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"
Mexico
Víctor Manuel
The price is €102
includes taxes & fees
30 Nov - 1 Dec
Glamping Cabin | Huge Window | Tree House Feel

Cabin in 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 €143
includes taxes & fees
5 Dec - 6 Dec
Bear Necessities Cabin - What Else Do You Need?

Cabin in Hillsboro

The Huntsmen

Cabin in Peebles

10.0 out of 10, Exceptional, (42)
"The cabin was perfect for our short stay."
United States
Beth R.
The price is €183
includes taxes & fees
7 Dec - 8 Dec
Hunter Lodge (Secluded in Amish Country and peaceful)

Cabin in Peebles

9.8 out of 10, Exceptional, (12)
"Loved the cabin and the peace and quiet was over the top! We came for a family reunion and found this by accident; so glad we did! Highly recommend! Very responsive owner and staff!"
United States
Bernie L.
The price is €189
includes taxes & fees
4 Dec - 5 Dec
Country Cabin in Amish Country

Cabin in Hamersville

9.6 out of 10, Exceptional, (27)
"The loveliest little cabin, all the extras to make your trip easy"
United States
jeanette
The price is €133
includes taxes & fees
30 Nov - 1 Dec
Flash Lodge Add-on Cabin-Pamela's Diamond

Cabin in Hillsboro

9.6 out of 10, Exceptional, (8)
"The property was clean and furnishings simple but comfortable."
United States
Margie R.
The price is €114
includes taxes & fees
9 Dec - 10 Dec
The Angler

Cabin in Green Township

9.8 out of 10, Exceptional, (9)
"We had a spectacular stay! Comfortable, Quiet, and Clean!Only a small suggestion Put a handle on the inside of the screen door and WD-40 the big door on cabin 1."
United Kingdom
Abby M.
The price is €102
includes taxes & fees
1 Dec - 2 Dec
Glamping Cabin | Huge Window | Nature Lovers Dream

Cabin in 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 €177
includes taxes & fees
17 Dec - 18 Dec
Cowboy Saloon Cabin

Cabin in Green Township

10.0 out of 10, Exceptional, (2)
"Property owners were very welcoming. The tree house and property were well maintained. "
United States
Marci
The price is €102
includes taxes & fees
30 Nov - 1 Dec
Glamping Cabin | Huge Window | Valley and Cliff Views

Holiday Home in Peebles

8.8 out of 10, Excellent, (18)
"Property was clean and a unique property. "
United States
Robert
The price is €227
includes taxes & fees
1 Dec - 2 Dec
Unique stay, hot tub, secluded

Cabin in West Union

9.8 out of 10, Exceptional, (27)
"Awesome cabin. Super clean and fun!"
United States
Phillip M.
The price is €197
includes taxes & fees
3 Dec - 4 Dec
Griffis Game Hunting and/or Getaway

Apartment in Augusta

2.0 star property
The price is €157
includes taxes & fees
30 Nov - 1 Dec
Charming Retreat: Walk to Distillery & River

Cabin in Hamersville

10.0 out of 10, Exceptional, (13)
"Very cute cabin on the lake! Great stay while at the ball fields! "
United States
Malia P.
The price is €198
includes taxes & fees
20 Dec - 21 Dec
Tom & Jerri's Rustic Cabin located on the lake

Cabin in Hillsboro

7.4 out of 10, Good, (8)
"We CD enjoyed our stay. It was spacious and cozy. The large bed is very tall so take a step stool. Mattresess are very confy. "
United States
Danelia
The price is €125
includes taxes & fees
9 Dec - 10 Dec
The White Stag

Cabin in Adams County

9.8 out of 10, Exceptional, (27)
"This property is very secluded for those who need a getaway from the hustle and bustle. Beautiful views."
United States
Michelle S.
The price is €322
includes taxes & fees
30 Nov - 1 Dec
Peaceful cabin with spectacular river and scenic views.
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 €102 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?

Unique stay, hot tub, secluded: This holiday home rental outside of Winchester is located in the city centre, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. Make the most of Access to hot tub in this rental home to help you unwind.

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.