Holiday Rentals in Winchester

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Our top choices for Winchester holiday rentals

The Perch - NEW / Downtown!

The Perch - NEW / Downtown!
Winchester
10.0 out of 10, Exceptional, (2 reviews)
"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 Perch - NEW / Downtown!

4 Bed 3 bath clean , spacious all brick home , welcome families and work groups

4 Bed 3 bath clean , spacious all brick home , welcome families and work groups
Winchester
10.0 out of 10, Exceptional, (6 reviews)
"Easy check in, Clean and close to everything. "
United States
Vicky R.
4 Bed 3 bath clean , spacious all brick home , welcome families and work groups

River Relaxation - Calm Riverfront Home in Winchester Kentucky

River Relaxation - Calm Riverfront Home in Winchester Kentucky
Winchester
7.0 out of 10, Good, (4 reviews)
"We loved the house, the hosts were great and super communicative! The house is also close to Lexington and Winchester so we had plenty to do and places to eat out! "
United States
Maeve R.
The price is €267
includes taxes & fees
8 Feb - 9 Feb
River Relaxation - Calm Riverfront Home in Winchester Kentucky

The Winchester

The Winchester
Winchester
8.4 out of 10, Very good, (7 reviews)
"I rented this house for my bridesmaids. It was a great location and house. The owner was accommodating and replied quickly "
United States
Karissa A.
The Winchester

Conveniently Located ~ WiFi ~ Central Heat & Air.

Conveniently Located ~ WiFi ~ Central Heat & Air.
Stanton
9.8 out of 10, Exceptional, (47 reviews)
"A great place to stay while exploring the area"
United States
lisa s.
Conveniently Located ~ WiFi ~ Central Heat & Air.

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

Furnished Glamping Tent/King Bed/Access to the Red River - Elusive Elk - #1
Stanton
10.0 out of 10, Exceptional, (24 reviews)
"Loved our stay. Most definitely coming back, had everything you needed for "
United States
cristal l.
The price is €119
includes taxes & fees
11 Feb - 12 Feb
Furnished Glamping Tent/King Bed/Access to the Red River - Elusive Elk - #1

Relaxing, cozy cabin in the heart of the Red River Gorge!

Relaxing, cozy cabin in the heart of the Red River Gorge!
Stanton
10.0 out of 10, Exceptional, (128 reviews)
"If you’re looking for a nice quiet get away this place is great! All the amenities of home are here and the cabin was very clean! We had a great time!"
United States
Sherri M.
The price is €215
includes taxes & fees
19 Feb - 20 Feb
Relaxing, cozy cabin in the heart of the Red River Gorge!

Natural Bridge State Resort Park

Natural Bridge State Resort Park
3.5 star property
Slade
8.6 out of 10, Excellent, (1,800 reviews)
"Friendly staff, convenient the have a restaurant and tavern on site. There is great hiking right out the back door. Appreciated a quiet stay."
United States
Kimberly
Natural Bridge State Resort Park

Bring a Pet: Peaceful Frenchburg Cabin on 1 Acre

Bring a Pet: Peaceful Frenchburg Cabin on 1 Acre
3.0 star property
Frenchburg
10.0 out of 10, Exceptional, (2 reviews)
"The cabin was adorable and had everything we needed for a weekend getaway. The host was very responsive, and we had a wonderful trip! "
United States
Anonymous traveller
The price is €223
includes taxes & fees
16 Feb - 17 Feb
Bring a Pet: Peaceful Frenchburg Cabin on 1 Acre

Secluded & Tranquil Cabin ~ Near Red River Gorge

Secluded & Tranquil Cabin ~ Near Red River Gorge
Irvine
10.0 out of 10, Exceptional, (58 reviews)
"Super inviting and felt like home. . ."
United States
Janet B.
The price is €224
includes taxes & fees
8 Feb - 9 Feb
Secluded & Tranquil Cabin ~ Near Red River Gorge

Mountaintop Cottage

Mountaintop Cottage
Stanton
10.0 out of 10, Exceptional, (27 reviews)
"I cannot say enough how CUTE this was we were so happy we found it. Loved the animals and will definitely stay again."
United States
Jessica H.
The price is €167
includes taxes & fees
10 Mar - 11 Mar
Mountaintop Cottage

Mountain Memories Cabin

Mountain Memories Cabin
Stanton
10.0 out of 10, Exceptional, (63 reviews)
"Great cabin!!"
United States
Amanda S.
The price is €177
includes taxes & fees
13 Feb - 14 Feb
Mountain Memories Cabin

Dappled Grey Cabin with hot tub at Red River Gorge

Dappled Grey Cabin with hot tub at Red River Gorge
Stanton
10.0 out of 10, Exceptional, (6 reviews)
"Great location, nice amentities (loved the hot tub), loved seeing the chickens and the dog that came to say hi"
United States
Jessica
The price is €299
includes taxes & fees
7 Mar - 8 Mar
Dappled Grey Cabin with hot tub at Red River Gorge

240 Sq Ft Tiny Home w/ WIFI in Irvine

240 Sq Ft Tiny Home w/ WIFI in Irvine
Irvine
10.0 out of 10, Exceptional, (11 reviews)
"We love our vacations simple and this place made just that happen! Close enough to get to places to see yet far enough away for perfect privacy! We really enjoyed our stay! "
United States
Samantha M.
The price is €182
includes taxes & fees
1 Mar - 2 Mar
240 Sq Ft Tiny Home w/ WIFI in Irvine

Unique Stay in a 1907 Log Cabin on The Kentucky River

Unique Stay in a 1907 Log Cabin on The Kentucky River
Lexington
9.6 out of 10, Exceptional, (108 reviews)
"Stayed for one night to ease a long drive to Florida. Would recommend and dog friendly."
United States
Ashley G.
The price is €157
includes taxes & fees
1 Mar - 2 Mar
Unique Stay in a 1907 Log Cabin on The Kentucky River

1800’s Historical Log Cabin near I-75 Interstate

1800’s Historical Log Cabin near I-75 Interstate
Lexington
9.4 out of 10, Exceptional, (59 reviews)
"Friendly host, warm welcoming home. Loved all the antiques and it was very comfortable!"
United States
J K.
The price is €204
includes taxes & fees
1 Mar - 2 Mar
1800’s Historical Log Cabin near I-75 Interstate

Cozy upstairs 2 bed/1 bath Richmond apt near EKU

Cozy upstairs 2 bed/1 bath Richmond apt near EKU
Richmond
10.0 out of 10, Exceptional, (33 reviews)
"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 €118
includes taxes & fees
13 Feb - 14 Feb
Cozy upstairs 2 bed/1 bath Richmond apt near EKU

Luxury on Main / South

Luxury on Main / South
Richmond
10.0 out of 10, Exceptional, (44 reviews)
"Great place for a quick weekend getaway."
United States
Jennifer
The price is €146
includes taxes & fees
8 Feb - 9 Feb
Luxury on Main / South

Modern 2bd 2ba - Near I75, No Steps, Free Wifi

Modern 2bd 2ba - Near I75, No Steps, Free Wifi
Richmond
9.8 out of 10, Exceptional, (85 reviews)
"Clean, close to campus . Would definitely stay again. "
United States
Christina K.
The price is €176
includes taxes & fees
8 Feb - 9 Feb
Modern 2bd 2ba - Near I75, No Steps, Free Wifi

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

East Suite-🕊️ Bleubird Studio + Suites -Art Gallery • Yoga • Boutique Stay
Georgetown
10.0 out of 10, Exceptional, (60 reviews)
"Great place to stay -- perfect location, wonderful host, beautiful accomodations, and sweet welcome dog on top of it all! Highly recommended. "
United States
l v.
The price is €196
includes taxes & fees
1 Mar - 2 Mar
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, 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 €115 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?

Lykins Park and College Park are a couple of scenic spots to enjoy the outdoors, whereas Bluegrass Heritage Museum is one of the cultural attractions. Southwind 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.