Winchester Vacation Rentals from $133: Search Short-Term Rentals

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

Mid-Century 3 BR In Heart of Downtown Lex : Visitors like this Winchester vacation home rental. It is located in the city center and has a patio, a selection of games, 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 you can cook with friends or family.

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In two weeks

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Our top choices for Winchester vacation rentals

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

Winchester

Tim T.

The Winchester

Winchester

Karissa A.

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

Stanton

cristal l.

$130 nightly

Jun 1 - Jun 2

Total with taxes and fees

Conveniently Located ~ WiFi ~ Central Heat & Air.

Stanton

lisa s.

$184 nightly

May 28 - May 29

Total with taxes and fees

Cabin, 2 Bedrooms, Kitchen | Living area | 32-inch flat-screen TV with cable channels, TV

Natural Bridge State Resort Park

Slade

Coty jay

$121 nightly

Jun 14 - Jun 15

Total with taxes and fees

Sunset Ridge Cabin – Hilltop Sunset Views Near Red River Gorge

Irvine

Ben H.

$175 nightly

May 27 - May 28

Total with taxes and fees

Larkspur Cabin with Hot Tub near Red River Gorge

Stanton

ElyCilia

$146 nightly

May 28 - May 29

Total with taxes and fees

Muddy Boots Hideout l Cozy 2BR l 15 min to RRG l WI-FI

Stanton

david

$151 nightly

May 27 - May 28

Total with taxes and fees

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Top Winchester Hotel Reviews

La Quinta Inn & Suites by Wyndham Lexington South / Hamburg

10/10 Excellent

"Quiet, safe, good breakfast, clean room, and friendly staff"

Country Inn & Suites by Radisson, Georgetown, KY

6/10 Okay

"The property in general is showing signs of age particularly in the pool area. It really needs a complete renovation. Our bathtub had rust stains and the caulking in areas looks roughly done. Also there were hairs around the base of the toilet. Our room was on the first floor near the pool and breakfast area. It was quite noisy. Our room looked out into the parking lot so we had to keep the blind shut and the room was quite dark. The breakfast was great. The eating area was clean. The staff was lovely and had fresh baked cookies available. The price was very reasonable compared to similar other places we stayed at."

The Manchester

10/10 Excellent

"The Manchester is a charming curated hotel with a refined but unpretentious aesthetic and vibe. The room was comfortable, considered, and full of character. The staff was warm, professional, and attentive without feeling overly formal. I’d say it has a distinctive southern charm that feels elevated without being contrived."

Natural Bridge State Resort Park

10/10 Excellent

"This place is awesome! You literally can hike to the bridge right out of the parking lot. The restaurant is good for a quick bite and reasonably priced. There is also a bar on premises. Room was clean and comfortable. Close to good motorcycle rides. Rode up there with a group of guys and had a great time!"

The Campbell House Lexington, Curio Collection by Hilton

6/10 Okay

"We’ve stayed in this hotel before and it’s very large. Perhaps it was the location of our room this time, which was in an older back hallway, that added to the less than desirable experience. The room was musty and smelled terrible. The entry door didn’t latch and needed to be locked to stay closed. The staff member who checked us in had the personality of cardboard. After waiting several minutes to check out, we just used the app - no one showed up. It’s decorated beautifully with great atmosphere and the restaurant was good, but overall didn’t measure up and not worth the $$. I’ll look elsewhere next time."

Hyatt Regency Lexington

4/10 Poor

"Below average rooms. Perhaps the heavy use by the various groups attending sporting events and conventions makes it difficult to keep the rooms in top working order. To be a Hyatt property the quality of the experience is way off. The common areas were nice enough, but the room itself was long past its prime. Banged up, roughed up, worn down/out. The only thing you get is location; unless you’re attending something at Rupp or the convention center there is no bang for your buck. Staff at registration truly struggled with their computer system which caused delay in getting checked in. Parking is very inconvenient especially if the weather isn’t perfect…crossing a busy roadway to your vehicle and a ticketing system that requires a validation every time you want to leave the property. A very poor overall experience for the price paid. Stay elsewhere if you’re seeking a quality experience. There’s certainly no luxury at this location."

Find out more about Winchester

Everything you need to know about Winchester vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Winchester vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Winchester vacation 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 low season months. For more hustle and bustle, you may prefer to visit Winchester in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $133 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Winchester rentals

At Expedia, we put the best Winchester vacation 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 vacation.

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.

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Frequently asked questions

Are there vacation rentals in Winchester?

Yes, we offer vacation rentals close to top points of interest in Winchester, or you can choose a more secluded option if you want a relaxing place to stay. Our travelers say Winchester has a good selection of restaurants. Make sure you have time to check out the coffeehouses and shopping during your trip.

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

Mid-Century 3 BR In Heart of Downtown Lex: Visitors like this Winchester vacation home rental. It is located in the city center and has a patio, a selection of games, 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 you can cook with friends or family.

How many vacation rentals are there in Winchester?

Expedia has 5 vacation rentals for your stay in Winchester.

What can I see and do in Winchester?

Winchester Traveling Trail and Lykins Park 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 vacation rentals like in Winchester?

Vacation rentals are privately owned properties you can reserve for a short or long stay in Winchester. Vacation rentals feature amenities like kitchens and laundry facilities so you'll have everything you need. If you're concerned about a sanitized environment, a vacation rental can offer a sense of privacy away from public hotel elevators and busy lobbies while still allowing you the excitement and enjoyment of travel. You'll also have more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a great option for a small group gathering.

Winchester Vacation Rentals

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Check prices for these dates

Our top choices for Winchester vacation rentals

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

The Winchester

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

Conveniently Located ~ WiFi ~ Central Heat & Air.

Natural Bridge State Resort Park

Sunset Ridge Cabin – Hilltop Sunset Views Near Red River Gorge

Larkspur Cabin with Hot Tub near Red River Gorge

Muddy Boots Hideout l Cozy 2BR l 15 min to RRG l WI-FI

The Lazy Hiker l Cozy 2BR l 15 min to RRG l WI-FI

Mountaintop Cottage

"Cloud Chaser" - Overlook Dome 005 in RRG

Hot Tub + Fire Pit: Frenchburg Cabin on 1 Acre

Mountain Memories Cabin

Hot Tub + Fire Pit: Frenchburg Cabin on 1 Acre

"Rocky Top" - Cozy RRG Cabin

THIS IS THE ONE! SHIPPING CONTAINER CABIN-VIEW-WIFI-NATURAL BRIDGE-NADA TUNNEL

"Cardinal Crest" - Overlook Dome 002 in RRG

3 Miles Hollerwood/ATV Parking/Mountain Views

Briar Patch Cabin RRG: Firepit, Sunset, WIFI

Where urban meets horses and bourbon , is exactly where you will find this adorable Lexington home in 40514. Sky Beauty is a 3 bedroom, 2 bathroom home features a fenced in backyard, updated kitchen, comfortable living room, Apple TV, and so much mor

Find vacation rentals that suit your style

Top Winchester Hotel Reviews

La Quinta Inn & Suites by Wyndham Lexington South / Hamburg

Find out more about Winchester

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