Holiday Rentals in Winchester

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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, (270)
"Lovely home fully stocked to cover all your needs. "
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, (46)
"My only concern about the property would be that there is another rental property prerty close. The property is very new, clean and well kept. Been to many properties and this is one of the very best. We will definitely be back for this property and would love to rent the other property as well."
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, (329)
"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!

Cowboy Saloon Cabin

9.4 out of 10, Exceptional, (15)
"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 €176
includes taxes & fees
27 Aug - 28 Aug
Cowboy Saloon Cabin

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

10.0 out of 10, Exceptional, (35)
"I had a great time while I was there. Nice and peaceful. Ken and Cindy and the dogs are awesome hosts. I'd definitely go again. "
Cozy newly remodeled camper with hot tub and fire pit close to hiking/kayaking

The Angler

9.8 out of 10, Exceptional, (6)
The Angler

Unique stay, hot tub, secluded

9.4 out of 10, Exceptional, (11)
"Comfy beds and great hottub. It was so cute and unique to stay in a grain bin. Very nicely decorated and clean. "
The price is €225
includes taxes & fees
27 Aug - 28 Aug
Unique stay, hot tub, secluded

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

10.0 out of 10, Exceptional, (105)
"Great place to get away. "
Peaceful historic log cabin getaway on 40 acres - NO cleaning fee!

New 3 Bedroom Log Cabin nestled in the woods with one acre fishing lake .

10.0 out of 10, Exceptional, (142)
"Completely set up for all your conveniences very comfortable furniture! Ease of check in and check out!"
New 3 Bedroom Log Cabin nestled in the woods with one acre fishing lake .

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

9.8 out of 10, Exceptional, (39)
"Host is helpful and check in/out was a breeze!"
McKeever Mansion-9,000 sq ft. Perfect for corporate, families, or special events

Amish-built cabin, serene and peaceful with pond and private dock for fishing.

10.0 out of 10, Exceptional, (21)
"The property was beautiful. The cabin was clean and well maintained. "
Amish-built cabin, serene and peaceful with pond and private dock for fishing.

Spacious 4-bedroom 19th Century home in historic downtown Maysville!

10.0 out of 10, Exceptional, (2)
"We were overly impressed by this property and the location. The house was emasculate and had such great character in every room. Check in and communication with the property own were top notch. The main areas in the town are all within short walking distance of the home. We will definitely look for this home again next year when we come back to Maysville. We won Oktoberfest king 2025 so we’ll definitely be back!"
Spacious 4-bedroom 19th Century home in historic downtown Maysville!

Secluded cabin located in Amish country

10.0 out of 10, Exceptional, (88)
"Thank you for our stay. Your place is beautiful and such a great location. Booking for October "
Secluded cabin located in Amish country

Bear Necessities Cabin - What Else Do You Need?

10.0 out of 10, Exceptional, (1)
"Great little spot! Cabin is super nice inside and out."
The price is €144
includes taxes & fees
27 Aug - 28 Aug
Bear Necessities Cabin - What Else Do You Need?

Experience Peace, Relaxation and Comfort in Kentucky with a touch of KENYA!

9.4 out of 10, Exceptional, (3)
"This was a great stay. Very easy to find and in a good area. Very clean and nice. "
The price is €240
includes taxes & fees
27 Aug - 28 Aug
Experience Peace, Relaxation and Comfort in Kentucky with a touch of KENYA!

Private cabin on 80 acre farm in Adams County Ohio

10.0 out of 10, Exceptional, (18)
"The property was beautiful. The cabin was clean and well maintained. "
Private cabin on 80 acre farm in Adams County Ohio

Enjoy a Secluded Amish-Built Cabin with Pond & Firepit on 6 Private Acres

10.0 out of 10, Exceptional, (108)
"so beautiful and peaceful!"
Enjoy a Secluded Amish-Built Cabin with Pond & Firepit on 6 Private Acres

LAKE HOUSE ON ROCKY FORK!

9.4 out of 10, Exceptional, (30)
"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 €351
includes taxes & fees
27 Aug - 28 Aug
LAKE HOUSE ON ROCKY FORK!

Lakeside Escape ~ Waterfront w/Hot Tub (NEW DOCK!)

10.0 out of 10, Exceptional, (4)
"Had everything we needed with easy access. Perfect environment for a weekend getaway. Having our own private dock made it even better, an overall fantastic experience"
Lakeside Escape ~ Waterfront w/Hot Tub (NEW DOCK!)

Glamping Cabin | Huge Window | Over a Creek

10.0 out of 10, Exceptional, (5)
"Beautiful location ."
The price is €110
includes taxes & fees
10 Sept - 11 Sept
Glamping Cabin | Huge Window | Over a Creek
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, 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 €110 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 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.