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Winchester Holiday Rentals

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Holiday Rentals in Winchester

The Perch - NEW / Downtown!

Winchester
10.0 out of 10, Exceptional, (2)
"The place was amazing! Very clean and comfortable. Great Italian restaurant down the street. Delicious dounuts around the corner.We went down to go into Lexington for Bourbon and wine tours. Would have liked to have a folder/ binder with information on what is in the area ( we did explore downtown) and also for information about checking out.We had 4 adults and could have used more towels (had 1 towel for each person) But we did make due.All in all would give this place 5 stars! We will be...
United States
Angela G.
The price is NZ$456
includes taxes & fees
15 Dec - 16 Dec
The Perch - NEW / Downtown!

River Relaxation - Calm Riverfront Home in Winchester Kentucky

Winchester
7.0 out of 10, Good, (4)
"Stayed Thursday-Monday. I had a number of interactions with the owner’s representative who was responsive and timely. "
United States
Sue W.
The price is NZ$554
includes taxes & fees
16 Nov - 17 Nov
River Relaxation - Calm Riverfront Home in Winchester Kentucky

Furnished Glamping Tent/King Bed/Access to the Red River - Elusive Elk - #1

Stanton
10.0 out of 10, Exceptional, (24)
"We absolutely loved it! Definitely will be staying again! Check in was simple! The bathrooms and showers were extremely clean as well as our tent! "
United States
Lisa G.
The price is NZ$239
includes taxes & fees
19 Nov - 20 Nov
Furnished Glamping Tent/King Bed/Access to the Red River - Elusive Elk - #1

Conveniently Located ~ WiFi ~ Central Heat & Air.

Stanton
9.8 out of 10, Exceptional, (47)
"It was a clean and comfortable place to stay. The area around was so beautiful."
United States
George
The price is NZ$307
includes taxes & fees
16 Nov - 17 Nov
Conveniently Located ~ WiFi ~ Central Heat & Air.

Natural Bridge State Resort Park

3.5 star property
Slade
8.6 out of 10, Excellent, (1770)
"Beautiful autumn stay."
United States
Cheryl
Natural Bridge State Resort Park

Bring a Pet: Peaceful Frenchburg Cabin on 1 Acre

3.0 star property
Frenchburg
10.0 out of 10, Exceptional, (2)
"This cabin was 100% the cleanest and nicest I’ve ever stayed in. Adorable, had everything needed for a comfortable stay. "
United States
Amy
The price is NZ$421
includes taxes & fees
24 Nov - 25 Nov
Bring a Pet: Peaceful Frenchburg Cabin on 1 Acre

Unique, Cozy Stay near Red River Gorge

Slade
7.4 out of 10, Good, (9)
"Love it ❤️"
United States
Barbara S.
The price is NZ$256
includes taxes & fees
17 Nov - 18 Nov
Unique, Cozy Stay near Red River Gorge

Dappled Grey Cabin with hot tub at Red River Gorge

2.0 star property
Stanton
10.0 out of 10, Exceptional, (4)
"The property was in good condition. Everything was clean. The area was quiet. The driveway could use some smoothing out but we had a nice stay."
United States
Monica
The price is NZ$378
includes taxes & fees
17 Nov - 18 Nov
Dappled Grey Cabin with hot tub at Red River Gorge

Minutes to Nada Tunnel + Natural Bridge SP / Views - Hot Tub - Firepit

2.0 star property
Stanton
9.8 out of 10, Exceptional, (14)
"Easy access into the house. All information was provided by our host. Home has everything you need, it was clean and beds are comfortable. Restaurants close by and enjoyed our stay. We will definitely do this again "
United States
Leanne
The price is NZ$598
includes taxes & fees
19 Nov - 20 Nov
Minutes to Nada Tunnel + Natural Bridge SP / Views - Hot Tub - Firepit

Tranquil Getaway in the Woods ~ Sunset Ridge

Irvine
10.0 out of 10, Exceptional, (79)
"The stay was awesome! My husband asked if we could stay another night. It is so quiet and peaceful here. Awesome experience!"
United States
Marsha
The price is NZ$281
includes taxes & fees
14 Dec - 15 Dec
Tranquil Getaway in the Woods ~ Sunset Ridge

Mountaintop Cottage

2.0 star property
Stanton
10.0 out of 10, Exceptional, (25)
"The cabin was in an excellent location and was very clean! The host was super helpful with providing directions and answering questions."
United States
Brandylynn M.
The price is NZ$340
includes taxes & fees
16 Nov - 17 Nov
Mountaintop Cottage

Unique Stay in a 1907 Log Cabin on The Kentucky River

Lexington
9.6 out of 10, Exceptional, (107)
"Great experience!"
United States
Gregory S.
The price is NZ$317
includes taxes & fees
24 Nov - 25 Nov
Unique Stay in a 1907 Log Cabin on The Kentucky River

Blue Sky Cabin Red River Gorge - Hot Tub Wi-Fi

Frenchburg
9.8 out of 10, Exceptional, (15)
"Place is absolutely beautiful! We absolutely loved it!would absolutely stay again"
United States
John M.
The price is NZ$477
includes taxes & fees
17 Nov - 18 Nov
Blue Sky Cabin Red River Gorge - Hot Tub Wi-Fi

"Valley View Lodge" - Modern Spacious Stay RRG - Slade

Stanton
9.8 out of 10, Exceptional, (28)
"Nice clean place to stay"
United States
Logan R.
The price is NZ$446
includes taxes & fees
17 Nov - 18 Nov
"Valley View Lodge" - Modern Spacious Stay RRG - Slade

Mountain Memories Cabin

Stanton
10.0 out of 10, Exceptional, (58)
"We had a wonderful stay! Clean, safe and excellent hospitality! "
United States
Matthew K.
The price is NZ$340
includes taxes & fees
16 Nov - 17 Nov
Mountain Memories Cabin

1800’s Historical Log Cabin near I-75 Interstate

Lexington
9.2 out of 10, Wonderful, (52)
"We loved this cozy old fashion and restored cabin. Since we were doing a tour of president's sites, it fit right in with our theme"
United States
Amanda B.
The price is NZ$415
includes taxes & fees
24 Nov - 25 Nov
1800’s Historical Log Cabin near I-75 Interstate

Cozy upstairs 2 bed/1 bath Richmond apt near EKU

Richmond
10.0 out of 10, Exceptional, (32)
"Always a great stay. We’ve stayed here several times, and will continue to do so when we visit our daughter at EKU. "
United States
Angela B.
The price is NZ$236
includes taxes & fees
21 Nov - 22 Nov
Cozy upstairs 2 bed/1 bath Richmond apt near EKU

My Old Kentucky Home

Lexington
10.0 out of 10, Exceptional, (27)
"It was easy to get in and the temp inside was great. The bedrooms were large! The bathroom was very small. The loft looked to be a decent size, but was only my wife and I so we didn’t use it. Overall a good place to stay. Close to campus and other places to shop and eat. "
United States
Ryan M.
The price is NZ$494
includes taxes & fees
16 Nov - 17 Nov
My Old Kentucky Home

This house is a 2 bedroom(s), 1 bathrooms, located in Georgetown, KY.

Georgetown
8.4 out of 10, Very good, (32)
"Host very helpful answered all questions. House very nice host goes above and beyond"
United States
Samantha W.
The price is NZ$312
includes taxes & fees
14 Dec - 15 Dec
This house is a 2 bedroom(s), 1 bathrooms, located in Georgetown, KY.

East Suite-🕊️ Bleubird Studio + Suites -Art Gallery • Yoga • Boutique Stay

Georgetown
10.0 out of 10, Exceptional, (60)
"Wonderful and quaint stay at a lovely home. Jane is fabtastic!"
United States
Ashley M.
The price is NZ$409
includes taxes & fees
14 Dec - 15 Dec
East Suite-🕊️ Bleubird Studio + Suites -Art Gallery • Yoga • Boutique Stay
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 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$239 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

Are there 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. Our travellers say Winchester has a good selection of restaurants. Make sure you have time to check out the coffee shops and shopping during your trip.

What are some of the best holiday rentals that Winchester has to offer?

Morrison Cabin Offers The Finest Interiors, Unique History & Very Best Location: This holiday home rental outside of Winchester is located in the city centre, and has a fireplace, a patio and air conditioning to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

How many holiday rentals are there in Winchester?

Expedia has 6 holiday rentals for your stay in Winchester.

What can I see and do in Winchester?

College Park and GRCHS Baseball Field are a couple of scenic spots to enjoy the outdoors, whereas Bluegrass Heritage Museum is one of the cultural attractions. Cassell Creek Golf Course and Winchester Opera House are other places to visit while you're in town.

What are holiday rentals like in Winchester?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Winchester. Holiday rentals offer amenities like kitchens and laundry facilities so you'll have everything you want. If you're concerned about cleanliness, a holiday rental can offer a sense of privacy away from public hotel lifts and busy reception areas while still allowing you a great travel experience. You'll also have more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a popular choice for family trips.