Winchester Holiday Rentals

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Check prices for these dates

In two weeks
31 Oct - 2 Nov
In two months
12 Dec - 14 Dec
In three months
9 Jan - 11 Jan
In four months
6 Feb - 8 Feb

Holiday Rentals in Winchester

Exterior
Glamping Cabin | Huge Window | Cliff and Animal Views
Glamping Cabin | Huge Window | Cliff and Animal Views
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!"
The price is NZ$199
includes taxes & fees
21 Oct - 22 Oct
Glamping Cabin | Huge Window | Cliff and Animal Views
Property grounds
Glamping Cabin | Huge Window | Over a Creek
Glamping Cabin | Huge Window | Over a Creek
10.0 out of 10, Exceptional, (6)
"Beautiful location ."
The price is NZ$199
includes taxes & fees
22 Oct - 23 Oct
Glamping Cabin | Huge Window | Over a Creek
1 bedroom
Home away from Home! - 1BR apartment in Maysville
Home away from Home! - 1BR apartment in Maysville
10.0 out of 10, Exceptional, (10)
"Wonderful apartment. Will book again next time we come to visit our family."
The price is NZ$187
includes taxes & fees
14 Nov - 15 Nov
Home away from Home! - 1BR apartment in Maysville
Front of property
Ohio Starlight Glamping Cabins
Ohio Starlight Glamping Cabins
2.0 star property
The price is NZ$218
includes taxes & fees
17 Nov - 18 Nov
Ohio Starlight Glamping Cabins
Fridge, microwave, stovetop, coffee/tea maker
Bear Necessities Cabin - What Else Do You Need?
Bear Necessities Cabin - What Else Do You Need?
10.0 out of 10, Exceptional, (4)
"Great little spot! Cabin is super nice inside and out."
The price is NZ$282
includes taxes & fees
19 Oct - 20 Oct
Bear Necessities Cabin - What Else Do You Need?
Property grounds
Glamping Cabin | Huge Window | Tree House Feel
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 NZ$199
includes taxes & fees
22 Oct - 23 Oct
Glamping Cabin | Huge Window | Tree House Feel
Fridge, microwave, oven
Country Cabin in Amish Country
Country Cabin in Amish Country
9.8 out of 10, Exceptional, (11)
"The cabin was absolutely gorgeous. I would recommend it to all of my friends "
The price is NZ$373
includes taxes & fees
16 Nov - 17 Nov
Country Cabin in Amish Country
Living area
Sleeps 4| Private Bathroom | Stunning Views
Sleeps 4| Private Bathroom | Stunning Views
The price is NZ$271
includes taxes & fees
19 Oct - 20 Oct
Sleeps 4| Private Bathroom | Stunning Views
Property grounds
Hunter Lodge (Secluded in Amish Country and peaceful)
Hunter Lodge (Secluded in Amish Country and peaceful)
10.0 out of 10, Exceptional, (39)
"Very peaceful and clean. Plenty of room. Beats the local motel by a mile. Not even comparable."
The price is NZ$360
includes taxes & fees
16 Nov - 17 Nov
Hunter Lodge (Secluded in Amish Country and peaceful)
Exterior
Flash Lodge Add-on Cabin-Pamela's Diamond
Flash Lodge Add-on Cabin-Pamela's Diamond
9.4 out of 10, Exceptional, (26)
"Thanks for the stay!"
The price is NZ$262
includes taxes & fees
20 Oct - 21 Oct
Flash Lodge Add-on Cabin-Pamela's Diamond
Smart TV
The Beach House
The Beach House
9.0 out of 10, Wonderful, (4)
"They were double booked but cleaned the cabin next door for us. Fireworks were amazing, watched from the back yard of the campsite the cabin was on. "
The price is NZ$269
includes taxes & fees
19 Oct - 20 Oct
The Beach House
Interior
Unique stay, hot tub, secluded
Unique stay, hot tub, secluded
9.2 out of 10, Wonderful, (15)
"Property was clean and a unique property. "
The price is NZ$447
includes taxes & fees
20 Oct - 21 Oct
Unique stay, hot tub, secluded
Terrace/patio
Cowboy Saloon Cabin
Cowboy Saloon Cabin
9.4 out of 10, Exceptional, (16)
"Cute, cozy, and clean. Stayed 2 nights; enjoyed fishing off the back deck. "
The price is NZ$349
includes taxes & fees
17 Nov - 18 Nov
Cowboy Saloon Cabin
Exterior
Griffis Game Hunting and/or Getaway
Griffis Game Hunting and/or Getaway
9.8 out of 10, Exceptional, (27)
"Awesome cabin. Super clean and fun!"
The price is NZ$386
includes taxes & fees
27 Oct - 28 Oct
Griffis Game Hunting and/or Getaway
Exterior
Glamping Cabin | Huge Window | Valley and Cliff Views
Glamping Cabin | Huge Window | Valley and Cliff Views
10.0 out of 10, Exceptional, (2)
"Property owners were very welcoming. The tree house and property were well maintained. "
The price is NZ$199
includes taxes & fees
19 Oct - 20 Oct
Glamping Cabin | Huge Window | Valley and Cliff Views
Interior
The Lake House
The Lake House
8.0 out of 10, Very good, (1)
"The place just smells clean! Bed is very comfortable & so is the furniture in the living area. Very relaxing atmosphere. My only wish is that the handrail going up the stairs of the door entrance, on the side, were more stable- it gives a false sense of security. Not a deal breaker, by any means, but, it could be an issue for older folks, depending on it. Again, a very relaxing atmosphere & would stay, again."
The price is NZ$269
includes taxes & fees
29 Oct - 30 Oct
The Lake House
Terrace/patio
Peaceful cabin with spectacular river and scenic views.
Peaceful cabin with spectacular river and scenic views.
9.8 out of 10, Exceptional, (23)
"Cozy cabin with a great view"
The price is NZ$635
includes taxes & fees
20 Oct - 21 Oct
Peaceful cabin with spectacular river and scenic views.
Exterior
Glamping Cabin | Huge Window | Nature Lovers Dream
Glamping Cabin | Huge Window | Nature Lovers Dream
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."
The price is NZ$199
includes taxes & fees
12 Nov - 13 Nov
Glamping Cabin | Huge Window | Nature Lovers Dream
Property grounds
Sleeps 12| Private Bathroom | Stunning Views
Sleeps 12| Private Bathroom | Stunning Views
10.0 out of 10, Exceptional, (6)
"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!"
Sleeps 12| Private Bathroom | Stunning Views
Property grounds
LAKE HOUSE ON ROCKY FORK LAKE MOUNTAIN VIEW DR!
LAKE HOUSE ON ROCKY FORK LAKE MOUNTAIN VIEW DR!
9.6 out of 10, Exceptional, (31)
"Super clean, comfortable and convenient to visit the Arc of Appalachia preserves nearby. There are several beautiful ones including the Highland Nature Sanctuary. The pups loved it too. The kitchen was well-stocked, beds comfortable and nice sun-room and back-yard."
The price is NZ$698
includes taxes & fees
28 Oct - 29 Oct
LAKE HOUSE ON ROCKY FORK LAKE MOUNTAIN VIEW DR!
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

Country Nights Inn

Country Nights Inn

10/10 Excellent
"This place was great for an overnight stay. Clean and comfortable. The owners were very proactive in communication and made sure we had what we needed. The internet was just a touch slow but could easily run a Zoom meeting or video calls. "
Michael 1-night trip
Posted 16 hours ago
Country Nights Inn

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 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 NZ$187 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?

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.