Holiday Rentals in Winchester

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Our top choices for Winchester holiday rentals

10.0 out of 10, Exceptional, (9 reviews)
"Great little spot! Cabin is super nice inside and out."
United States
Jason M.
The price is €142
includes taxes & fees
15 Jan - 16 Jan
Bear Necessities Cabin - What Else Do You Need?
9.6 out of 10, Exceptional, (27 reviews)
"Thanks for the stay!"
United States
Matt B.
The price is €133
includes taxes & fees
25 Jan - 26 Jan
Flash Lodge Add-on Cabin-Pamela's Diamond
9.8 out of 10, Exceptional, (8 reviews)
"Had a wonderful time! Bathrooms and cabin were very clean and it was very quiet. Just what we needed."
United States
Kristen W.
The price is €102
includes taxes & fees
15 Jan - 16 Jan
Glamping Cabin | Huge Window | Over a Creek
9.8 out of 10, Exceptional, (13 reviews)
"Beautiful clean place "
United States
Casey J.
The price is €167
includes taxes & fees
15 Jan - 16 Jan
Country Cabin in Amish Country
10.0 out of 10, Exceptional, (2 reviews)
"We had a great stay, we loved the horse and goats. It was peaceful and beautiful, exactly what we needed! Will definitely stay again! "
United States
Callie J.
The price is €102
includes taxes & fees
15 Jan - 16 Jan
Glamping Cabin | Huge Window | Cliff and Animal Views
10.0 out of 10, Exceptional, (44 reviews)
"Beautiful cabin! "
United States
Anonymous traveller
The price is €167
includes taxes & fees
15 Jan - 16 Jan
Hunter Lodge (Secluded in Amish Country and peaceful)

Holiday Home in Peebles

Unique stay, hot tub, secluded
8.8 out of 10, Excellent, (18 reviews)
"This is an amazing property and we will be returning because it was so luxurious."
United States
Amy
The price is €229
includes taxes & fees
15 Jan - 16 Jan
Unique stay, hot tub, secluded
9.0 out of 10, Wonderful, (19 reviews)
"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
15 Jan - 16 Jan
Glamping Cabin | Huge Window | Tree House Feel
2.0 star property
10.0 out of 10, Exceptional, (1 review)
"Rodney and Ruth were very responsive. Adorable space within walking distance to the Augusta Distillery."
United States
Misty
The price is €154
includes taxes & fees
27 Jan - 28 Jan
Charming Retreat: Walk to Distillery & River

Cabin in Hamersville

Cowboy Saloon Cabin
9.4 out of 10, Exceptional, (20 reviews)
"Clean & cool little place."
United States
Stephen
The price is €176
includes taxes & fees
25 Jan - 26 Jan
Cowboy Saloon Cabin

Cabin in Hillsboro

The Huntsmen
6.0 out of 10, (1 review)
The price is €87
includes taxes & fees
15 Jan - 16 Jan
The Huntsmen
9.6 out of 10, Exceptional, (31 reviews)
"Very clean and neat, everything was as described, the grill was a bit rusty but overall was a wonderful experience!!"
United States
Troy B.
The price is €352
includes taxes & fees
18 Jan - 19 Jan
LAKE HOUSE ON ROCKY FORK LAKE MOUNTAIN VIEW DR!
10.0 out of 10, Exceptional, (7 reviews)
"This cabin was exactly what we were looking for: Cozy, peaceful, clean, comfortable and all the amenities. Located near several great hiking spots within a short drive. Great indoor and outdoor space. Host was very friendly and responsive. Highly recommend this place!"
United States
Amy H.
The price is €278
includes taxes & fees
15 Jan - 16 Jan
Sleeps 12| Private Bathroom | Stunning Views
9.6 out of 10, Exceptional, (4 reviews)
"Nicely decorated property. This was perfect for our family and we’d definitely stay hear again when in Ripley. "
United States
John and Chris S.
The price is €203
includes taxes & fees
27 Jan - 28 Jan
Spacious 3-bedroom apartment with WiFi, AC in charming Ripley

Cabin in Hillsboro

The Angler
9.2 out of 10, Wonderful, (9 reviews)
"Clean and great for a couple of fisherman enjoying the lake and surrounding area. "
United States
Jerry P.
The price is €113
includes taxes & fees
18 Jan - 19 Jan
The Angler
9.8 out of 10, Exceptional, (9 reviews)
"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
15 Jan - 16 Jan
Glamping Cabin | Huge Window | Nature Lovers Dream
6.8 out of 10, (3 reviews)
"Yes, it would have been perfect for leashed pets. Cabin was very cozy and fit our needs well. One thing we did notice that would've been great if they had some bowls for mixing pancakes and such. "
United States
Dane C.
The price is €137
includes taxes & fees
15 Jan - 16 Jan
Sleeps 4| Private Bathroom | Stunning Views
9.8 out of 10, Exceptional, (6 reviews)
"Was clean well stocked and everything wee we’re looking for "
United States
Antony W.
The price is €271
includes taxes & fees
15 Jan - 16 Jan
A Delightful A-Frame on 20-Acres with Hiking Trails, Hot Tub, Wifi, and More
10.0 out of 10, Exceptional, (2 reviews)
"Property owners were very welcoming. The tree house and property were well maintained. "
United States
Marci
The price is €102
includes taxes & fees
15 Jan - 16 Jan
Glamping Cabin | Huge Window | Valley and Cliff Views
9.8 out of 10, Exceptional, (38 reviews)
"Easy to stay"
United States
Max
The price is €162
includes taxes & fees
15 Jan - 16 Jan
The Bear Den (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, 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 €87 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?

Peaceful 8 Bedroom 5 Bath w/patio bar-grill and swimming pond: This holiday home rental outside of Winchester is located in a rural location, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 8 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games.

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 John Rankin House.

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.