Winchester Holiday Rentals from AU$93: Search Short-Term Rentals

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

Renovated train station on thoroughbred horse farm. : This holiday home rental outside of Winchester is located in the city centre, and has a garden, a BBQ and air conditioning to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop.

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In two weeks

In two months

In three months

In four months

Our top choices for Winchester holiday rentals

1. 4 Bed 3 bath clean , spacious all brick home , welcome families and work groups

Winchester

Tim T.

includes taxes & fees

7 Sept - 8 Sept

A black leather sofa with a center console, a glass table, and two boxes on the table.

2. The Winchester

Winchester

Gina

includes taxes & fees

7 Sept - 8 Sept

3. 1800’s Historical Log Cabin near I-75 Interstate

Lexington

Sarah

includes taxes & fees

7 Sept - 8 Sept

4. Unique Stay in a 1907 Log Cabin on The Kentucky River

Lexington

Anonymous traveller

includes taxes & fees

8 Sept - 9 Sept

5. Sunset Ridge Cabin – Hilltop Sunset Views Near Red River Gorge

Irvine

Emmalynn P.

includes taxes & fees

7 Sept - 8 Sept

6. 2 Full Beds | Non-Smoking, Micfridge

Lexington

Anonymous traveller

includes taxes & fees

7 Sept - 8 Sept

Cabin, 2 Bedrooms, Kitchen | Living area

7. Natural Bridge State Resort Park

Slade

Monty

includes taxes & fees

13 Sept - 14 Sept

8. Relaxing Hot Tub | S’mores Fire Pit | Garage

LEXINGTON

Lori M.

includes taxes & fees

7 Sept - 8 Sept

9. Cozy 1-bedroom in Lexington

Lexington

Renae

includes taxes & fees

14 Sept - 15 Sept

10. My Old Kentucky Home

Lexington

brian g.

includes taxes & fees

8 Sept - 9 Sept

11. Dappled Grey Cabin with hot tub at Red River Gorge

Stanton

Jessica

includes taxes & fees

7 Sept - 8 Sept

12. Luxury on Main / South

Richmond

Robert T.

includes taxes & fees

8 Sept - 9 Sept

13. Treetops Solar Sanctuary

Chevy Chase

Matthew Y.

includes taxes & fees

13 Sept - 14 Sept

14. Westfield Blue

Richmond

Keith G.

includes taxes & fees

7 Sept - 8 Sept

15. Conveniently Located ~ WiFi ~ Central Heat & Air.

Stanton

lisa s.

includes taxes & fees

7 Sept - 8 Sept

16. Mountaintop Cottage

Stanton

andymorg

includes taxes & fees

8 Sept - 9 Sept

17. Great Locatoin- Mins to Rupp-Kroger Field-Downtown Lexington- Modern Retro 70's

Lexington

Caroline B.

includes taxes & fees

7 Sept - 8 Sept

18. Mountain Memories Cabin

Stanton

Robert C.

includes taxes & fees

15 Sept - 16 Sept

19. This condominium is a 1 bedroom(s), 1 bathrooms, located in Lexington, KY.

Lexington

Andrew K.

includes taxes & fees

7 Sept - 8 Sept

20. Luxe Home Downtown - Sleeps 6. Off-street parking

Northside District

Tim M.

includes taxes & fees

9 Sept - 10 Sept

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Top Winchester Hotel Reviews

GuestHouse Lexington

10/10 Excellent

"Clean room! Nice staff !"

Holiday Inn Express Lexington - Horse Park Area by IHG

10/10 Excellent

"I enjoyed the modern and sleek design of the property in general and my room in particular. The room was both inviting and superbly designed for maxim utility of space without skimping on the amenities. Each staff member I encountered was kind. helpful, welcoming and professional, and was given the perfect room for my business trip. It had a super-comfortable pillow-top bed dressed in clean, crisp white sheets and bedding and I liked the use of the sliding barn-door style entrance to the bathroom. The modern design also incorporated laminate flooring which totally eliminated the icks I get from hotel carpets. This hotel seems to have been designed with the help of business-travelers by a company who listens to it's customers. The breakfast lobby was also inviting and well designed and had a great selection of food. This was the first time I have stayed at a Holiday Inn Express in a long time, but this property had everything I could ask for from a roadside hotel. I will definitely be seeking out this brand, if not this exact property on my next trip."

Marriott Lexington Griffin Gate Golf Resort & Spa

8/10 Good

"It was good but lots of construction or I’d give it 5 stars. The best part was the indoor pool which was the perfect temperature. Most the time hotel pools are way too cold but it was perfect. I so wish the hot tub was not under construction. However, they also had an outdoor pool and hot tub. The gym was on the small side but who cares when you can do laps in the perfect temperature pool lol."

Natural Bridge State Resort Park

10/10 Excellent

"We went there for our 58th anniversary. The place fit right into the Red River Gorge area. The view of the trees from our room was beautiful. The room had a little musty smell but it seemed to fit the atmosphere of the area. From the dinning room you could watch the squirrels and birds enjoy the feeders The food and the staff were great! To sum it up the Lodge was not real fancy but just prefect for us"

Fairfield Inn & Suites by Marriott Lexington North

10/10 Excellent

"Melissa and Louis at the front desk are exceptional employees. They welcomed me in the most personal way and helped me with directions and everything I needed. My room was conveniently close to the front desk and the breakfast was fuller (with more items and options) than other comparable hotels I have stayed in. My room did not have a luggage rack but Melissa quickly found one for me. The WiFi was a bit slow, but I still was able to do my work. The only problem I encountered during the stay was lack of parking close to the front desk and obstructions due to the concrete work going on blocking the front entrance entirely on my departure day and also blocking the side entrance with workers standing around, making backing out of my parking place challenging. I was glad my key worked to get in the side door, but I don't know what I would have done if I had found the entrance completely blocked off if the day prior when I was checking in. But overall, the location was perfect as was the room and breakfast and the help at the front desk was EXTRAORDINARY. Those two employees deserve kudos for service."

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 favourite 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 depend 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 AU$93 per night. Entering your travel dates in the search wizard might find you 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?

Renovated train station on thoroughbred horse farm.: This holiday home rental outside of Winchester is located in the city centre, and has a garden, a BBQ and air conditioning to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop.

How many holiday rentals are there in Winchester?

Expedia has 8 holiday rentals for your stay in Winchester.

What can I see and do in Winchester?

Community Park and College Park 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.

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Check prices for these dates

Our top choices for Winchester holiday rentals

1. 4 Bed 3 bath clean , spacious all brick home , welcome families and work groups

2. The Winchester

3. 1800’s Historical Log Cabin near I-75 Interstate

4. Unique Stay in a 1907 Log Cabin on The Kentucky River

5. Sunset Ridge Cabin – Hilltop Sunset Views Near Red River Gorge

6. 2 Full Beds | Non-Smoking, Micfridge

7. Natural Bridge State Resort Park

8. Relaxing Hot Tub | S’mores Fire Pit | Garage

9. Cozy 1-bedroom in Lexington

10. My Old Kentucky Home

11. Dappled Grey Cabin with hot tub at Red River Gorge

12. Luxury on Main / South

13. Treetops Solar Sanctuary

14. Westfield Blue

15. Conveniently Located ~ WiFi ~ Central Heat & Air.

16. Mountaintop Cottage

17. Great Locatoin- Mins to Rupp-Kroger Field-Downtown Lexington- Modern Retro 70's

18. Mountain Memories Cabin

19. This condominium is a 1 bedroom(s), 1 bathrooms, located in Lexington, KY.

20. Luxe Home Downtown - Sleeps 6. Off-street parking

Find holiday rentals that suit your style

Top Winchester Hotel Reviews

GuestHouse Lexington

Holiday Inn Express Lexington - Horse Park Area by IHG

Marriott Lexington Griffin Gate Golf Resort & Spa

Spark by Hilton Lexington Hamburg

Natural Bridge State Resort Park

Embassy Suites by Hilton Lexington Green

Country Inn & Suites by Radisson, Georgetown, KY

Fairfield Inn & Suites by Marriott Lexington North

Find out more about Winchester

Frequently asked questions

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