Winchester Holiday Rentals from €57: 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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Our top choices for Winchester holiday rentals

Coffee/tea maker, fridge, microwave, oven

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

Winchester

Tim T.

includes taxes & fees

16 Aug - 17 Aug

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

16 Aug - 17 Aug

3. River Relaxation - Calm Riverfront Home in Winchester Kentucky

Winchester

Polly H.

includes taxes & fees

16 Aug - 17 Aug

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

Lexington

Anonymous traveller

includes taxes & fees

23 Aug - 24 Aug

Cabin, 2 Bedrooms, Kitchen | Living area

5. Natural Bridge State Resort Park

Slade

Jeff

includes taxes & fees

20 Aug - 21 Aug

6. 1800’s Historical Log Cabin near I-75 Interstate

Lexington

Laurie D.

includes taxes & fees

25 Aug - 26 Aug

7. Cabin in Kentucky Horse Country

Bourbon County

Siobann S.

includes taxes & fees

9 Sept - 10 Sept

8. Entire Home in Hamburg!

Liberty Area

Monte R.

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Top Winchester Hotel Reviews

Elwood Hotel & Suites

10/10 Excellent

"Excellent stay at this remodeled, non chain hotel, conveniently located and with free parking. Beds and lines are of a high quality, large room, wide selection of foods for breakfast (not included in the room price), very friendly personnel. Keep in mind that AC unit is rather loud. A writing desk in the room would be nice."

Country Inn & Suites by Radisson, Georgetown, KY

10/10 Excellent

"From arrival to departure, our stay was very good. The room was clean and well maintained. The staff was friendly and helpful. The breakfast was good and there was a staff member there to keep the dining area clean and the food stocked. A good stay!"

Holiday Inn Express Lexington - Horse Park Area by IHG

10/10 Excellent

"The room was exceptionally clean. The staff at the front desk, especially the guy who checked us in was very helpful and kind. We didn’t have the breakfast because we had to leave before breakfast started but we were made aware of the timeframe if we were able to eat. The parking was accessible and not too far of a walk if you had to park further away from the main door. Overall, our stay was great and we would stay again if we’re in the area and need a hotel!"

Embassy Suites by Hilton Lexington/UK Coldstream

8/10 Good

"The staff was amazing. One of our TVs didn’t work and the maintenance gentleman was so amazing. The you g lady at the front desk was sweet as well. I’m not sure what laundry soap they use but it does not smell good. In fact it stinks. A couple of our towels were not white and had hair in them. The sheets and blankets also smelled of whatever soap they use and its was not pleasant. The soap and shower gel also smell terrible. I have stayed and worse hotels with better scents. Breakfast was great. They should think about including turkey sausage and bacon as not everyone eats pork. This is my second stay here and I had the same experience. Thought the towels and bedding were a fluke the first time but nope, it’s how they roll. May need to try another hotel on my next trip to Lexington."

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 €57 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?

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?

Wiseman Park and Winchester Traveling Trail are a couple of scenic spots to enjoy the outdoors, whereas Bluegrass Heritage Museum is one of the cultural attractions. Winchester Opera House and Clark County Courthouse 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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Our top choices for Winchester holiday rentals