An aerial view of a historic town with a prominent clock tower, narrow streets lined with historic buildings, and a mix of commercial and residential areas.

Holiday Rentals in Winchester

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Our top choices for Winchester holiday rentals

River Relaxation - Calm Riverfront Home in Winchester Kentucky

River Relaxation - Calm Riverfront Home in Winchester Kentucky
Winchester
7.6 out of 10, Good, (5 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 €357
includes taxes & fees
29 Jul - 30 Jul
River Relaxation - Calm Riverfront Home in Winchester Kentucky

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
9.8 out of 10, Exceptional, (9 reviews)
"Very homey place to stay! Nice neighborhood!"
United States
Tim T.
The price is €272
includes taxes & fees
29 Jun - 30 Jun
4 Bed 3 bath clean , spacious all brick home , welcome families and work groups

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, (50 reviews)
"A great place to stay while exploring the area"
United States
lisa s.
The price is €189
includes taxes & fees
29 Jun - 30 Jun
Conveniently Located ~ WiFi ~ Central Heat & Air.

Natural Bridge State Resort Park

Natural Bridge State Resort Park
3.5 star property
Slade
8.6 out of 10, Excellent, (1,940 reviews)
"Great area Nice place to stay"
United States
Julie
The price is €123
includes taxes & fees
12 Jul - 13 Jul
Natural Bridge State Resort Park

BEST CABIN EVER!-IN THE WOODS-SUPER CLEAN-HOT TUB-PAVED ROAD-NATURAL BRIDGE PARK

BEST CABIN EVER!-IN THE WOODS-SUPER CLEAN-HOT TUB-PAVED ROAD-NATURAL BRIDGE PARK
Stanton
10.0 out of 10, Exceptional, (326 reviews)
"Wonderful place to stay. We loved it!"
United States
Jamie B.
The price is €277
includes taxes & fees
30 Jun - 1 Jul
BEST CABIN EVER!-IN THE WOODS-SUPER CLEAN-HOT TUB-PAVED ROAD-NATURAL BRIDGE PARK

YOU WILL LOVE THIS ONE!-SUPER CLEAN-KING BEDS-HOT TUB-VIEW-HI SPEED WIFI-BOOK IT

YOU WILL LOVE THIS ONE!-SUPER CLEAN-KING BEDS-HOT TUB-VIEW-HI SPEED WIFI-BOOK IT
Stanton
10.0 out of 10, Exceptional, (367 reviews)
"Great spot for weekend getaway. "
United States
Liz A.
The price is €285
includes taxes & fees
2 Jul - 3 Jul
YOU WILL LOVE THIS ONE!-SUPER CLEAN-KING BEDS-HOT TUB-VIEW-HI SPEED WIFI-BOOK IT

Hot Tub + Fire Pit: Frenchburg Cabin on 1 Acre

Hot Tub + Fire Pit: 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 €275
includes taxes & fees
29 Jun - 30 Jun
Hot Tub + Fire Pit: Frenchburg Cabin on 1 Acre

Mountain Memories Cabin

Mountain Memories Cabin
Stanton
10.0 out of 10, Exceptional, (78 reviews)
"Would stay again. Responsive host, property was very clean and host had left nice touches / decorations for valentines day weekend visit."
United States
Robert C.
The price is €174
includes taxes & fees
29 Jun - 30 Jun
Mountain Memories Cabin

Mountaintop Cottage

Mountaintop Cottage
Stanton
10.0 out of 10, Exceptional, (37 reviews)
"Great stay! Beautiful property and an awesome donkey"
United States
andymorg
The price is €169
includes taxes & fees
29 Jun - 30 Jun
Mountaintop Cottage

Briar Patch Cabin RRG: Firepit, Sunset, WIFI

Briar Patch Cabin RRG: Firepit, Sunset, WIFI
Stanton
10.0 out of 10, Exceptional, (48 reviews)
"The cabin was beautiful. We had a peaceful stay with everything we needed."
United States
Jennifer B.
The price is €188
includes taxes & fees
5 Jul - 6 Jul
Briar Patch Cabin RRG: Firepit, Sunset, WIFI

Cabin in Kentucky Horse Country

Cabin in Kentucky Horse Country
Bourbon County
10.0 out of 10, Exceptional, (81 reviews)
"Beautiful cabin with wonderful views in a peaceful setting"
United Kingdom
Siobann S.
The price is €430
includes taxes & fees
29 Jun - 30 Jun
Cabin in Kentucky Horse Country

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, (70 reviews)
"Excellent stopover. "
United States
Robert W.
The price is €218
includes taxes & fees
5 Jul - 6 Jul
1800’s Historical Log Cabin near I-75 Interstate

East Suite-🕊️ at Bleubird Studio, Walk to Downtown

East Suite-🕊️ at Bleubird Studio, Walk to Downtown
Georgetown
10.0 out of 10, Exceptional, (66 reviews)
"Absolutely beautiful accommodations that are within walking distance to the downtown Georgetown area. Jane and her pooch Sandy were divine. Will stay there again in the future."
United States
Laura ..
The price is €206
includes taxes & fees
29 Jun - 30 Jun
East Suite-🕊️ at Bleubird Studio, Walk to Downtown

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
Dappled Grey Cabin with hot tub at Red River Gorge

Hot Tub! Fire pit! Picnic area & Grill! View Hardwicks Creek Haven@RRG

Hot Tub! Fire pit! Picnic area & Grill! View Hardwicks Creek Haven@RRG
Clay City
10.0 out of 10, Exceptional, (51 reviews)
"The hot tub was very nice and the property was so beautiful!!"
United States
April
Hot Tub! Fire pit! Picnic area & Grill! View Hardwicks Creek Haven@RRG

Bourbon Run - HotTub/ Ark 30min/ Horse Park 12min/ Walk Downtown/ 4BR Sleeps 8

Bourbon Run - HotTub/ Ark 30min/ Horse Park 12min/ Walk Downtown/ 4BR Sleeps 8
Georgetown
10.0 out of 10, Exceptional, (40 reviews)
"Great (house), clean rooms, clean bathrooms, fully furnished kitchen, quick response by host. "
United States
Leslie S.
Bourbon Run - HotTub/ Ark 30min/ Horse Park 12min/ Walk Downtown/ 4BR Sleeps 8

STOP SCROLLING!-HOT TUB-HIGH SPEED WIFI-SUPER CLEAN-NATURAL BRIDGE-NADA TUNNEL

STOP SCROLLING!-HOT TUB-HIGH SPEED WIFI-SUPER CLEAN-NATURAL BRIDGE-NADA TUNNEL
Stanton
10.0 out of 10, Exceptional, (165 reviews)
"The place was great!! Hot tub was a nice addition. The property was clean, quiet and relaxing! I would stay again if in the area!!"
United States
Denise M.
The price is €251
includes taxes & fees
29 Jun - 30 Jun
STOP SCROLLING!-HOT TUB-HIGH SPEED WIFI-SUPER CLEAN-NATURAL BRIDGE-NADA TUNNEL

Spacious Secluded Cabin on 100 Acres Near Red River Gorge

Spacious Secluded Cabin on 100 Acres Near Red River Gorge
Irvine
10.0 out of 10, Exceptional, (78 reviews)
The price is €228
includes taxes & fees
30 Jun - 1 Jul
Spacious Secluded Cabin on 100 Acres Near Red River Gorge

Stargazer Cabin-Look Up. Relax. Repeat.

Stargazer Cabin-Look Up. Relax. Repeat.
Irvine
10.0 out of 10, Exceptional, (23 reviews)
"Great cabin, beautiful views. Great roads for riding motorcycles in the hills of Ky. "
United States
James D.
The price is €303
includes taxes & fees
1 Jul - 2 Jul
Stargazer Cabin-Look Up. Relax. Repeat.
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 €123 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?

This bungalow is a 2 bedroom(s), 1 bathrooms, located in Lexington, KY.: This holiday home rental outside of Winchester is equipped with a garden, air conditioning and laundry facilities to help you feel comfortable during your stay. Kitchen amenities include a fridge to make your meal-planning easier.

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?

Community Park and The Holler are a couple of scenic spots to enjoy the outdoors, whereas Bluegrass Heritage Museum is one of the cultural attractions. Wiseman Park and Winchester Traveling Trail 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.