MAY 9, 2023 - WINCHESTER, KENTUCKY - aerial view of historic small town of Winchester with Town Clocktower and historic storefronts and buildings

Winchester Vacation Rentals

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Check prices for these dates

In two weeks
3 Jul - 5 Jul
In two months
14 Aug - 16 Aug
In three months
11 Sep - 13 Sep
In four months
9 Oct - 11 Oct

Our top choices for Winchester vacation rentals

Property grounds

Glamping Cabin | Huge Window | Cliff and Animal Views

Glamping Cabin | Huge Window | Cliff and Animal Views
Green Township
10.0 out of 10, Exceptional, (2 reviews)
"We had a great stay, we loved the horse and goats. It was peaceful and beautiful, exactly what we needed! Will definitely stay again! "
United States
Callie J.
The price is AED 253
AED 419 total
includes taxes & fees
23 Jun - 24 Jun
Glamping Cabin | Huge Window | Cliff and Animal Views
Terrace/patio

Sleeps 4| Private Bathroom | Stunning Views

Sleeps 4| Private Bathroom | Stunning Views
Green Township
7.2 out of 10, Good, (5 reviews)
"We enjoyed staying at this unique cabin. Our children liked the animals and enjoyed petting some of them. "
United States
Al G.
The price is AED 496
AED 569 total
includes taxes & fees
22 Jun - 23 Jun
Sleeps 4| Private Bathroom | Stunning Views
Property grounds

Glamping Cabin | Huge Window | Over a Creek

Glamping Cabin | Huge Window | Over a Creek
Green Township
9.8 out of 10, Exceptional, (8 reviews)
"Had a wonderful time! Bathrooms and cabin were very clean and it was very quiet. Just what we needed."
United States
Kristen W.
The price is AED 253
AED 419 total
includes taxes & fees
22 Jun - 23 Jun
Glamping Cabin | Huge Window | Over a Creek
Fridge, microwave, oven

Country Cabin in Amish Country

Country Cabin in Amish Country
Peebles
9.8 out of 10, Exceptional, (16 reviews)
"Beautiful clean place "
United States
Casey J.
The price is AED 386
AED 684 total
includes taxes & fees
12 Jul - 13 Jul
Country Cabin in Amish Country
House (1 Bedroom) | Interior

Stout Cabin w/ Fire Pit: 1 Mi to Ohio River!

Stout Cabin w/ Fire Pit: 1 Mi to Ohio River!
3.0 star property
Rome
The price is AED 338
AED 658 total
includes taxes & fees
22 Jun - 23 Jun
Stout Cabin w/ Fire Pit: 1 Mi to Ohio River!
Interior

Secluded in Amish Country and peaceful

Secluded in Amish Country and peaceful
Peebles
9.8 out of 10, Exceptional, (30 reviews)
"Very cozy, warm an had everything we could possibly need, love the memory book left for guests to share, we were in Bunk House, would love to see each of the others recommend staying "
United States
Michael J.
The price is AED 422
AED 698 total
includes taxes & fees
22 Jun - 23 Jun
Secluded in Amish Country and peaceful
TV

Stout Cabin w/ Fire Pit: 1 Mi to Ohio River!

Stout Cabin w/ Fire Pit: 1 Mi to Ohio River!
Stout
10.0 out of 10, Exceptional, (8 reviews)
"Very peaceful, amazing veiw perfect getaway will definitely stay again. "
United States
Kenneth
The price is AED 301
AED 662 total
includes taxes & fees
22 Jun - 23 Jun
Stout Cabin w/ Fire Pit: 1 Mi to Ohio River!
Interior

Bear Necessities Cabin - What Else Do You Need?

Bear Necessities Cabin - What Else Do You Need?
West Union
10.0 out of 10, Exceptional, (12 reviews)
"Great little spot! Cabin is super nice inside and out."
United States
Jason M.
The price is AED 340
AED 622 total
includes taxes & fees
30 Jun - 1 Jul
Bear Necessities Cabin - What Else Do You Need?
Microwave, oven, stovetop

The Huntsmen

The Huntsmen
Hillsboro
6.4 out of 10, (5 reviews)
"A basic cabin in a good area for pets."
United States
Marcia
The price is AED 327
AED 424 total
includes taxes & fees
24 Jun - 25 Jun
The Huntsmen
Interior

1 Bed/1 Bath Guest House

1 Bed/1 Bath Guest House
Hillsboro
9.6 out of 10, Exceptional, (4 reviews)
"New and comfortable and private."
United States
Leigh K.
The price is AED 264
AED 456 total
includes taxes & fees
29 Jun - 30 Jun
1 Bed/1 Bath Guest House
Fridge, microwave, oven, stovetop

Griffis Game Hunting and/or Getaway

Griffis Game Hunting and/or Getaway
West Union
9.8 out of 10, Exceptional, (31 reviews)
"Super nice host, very clean cabin."
United States
BRAD T.
The price is AED 496
AED 789 total
includes taxes & fees
22 Jun - 23 Jun
Griffis Game Hunting and/or Getaway
Interior

Cowboy Saloon Cabin

Cowboy Saloon Cabin
Hamersville
9.6 out of 10, Exceptional, (22 reviews)
"Absolutely Wonderful. & Plan to return this Summer."
United States
Jared
The price is AED 496
AED 753 total
includes taxes & fees
22 Jun - 23 Jun
Cowboy Saloon Cabin
Outdoor spa tub

Meadowview Guest House

Meadowview Guest House
Hillsboro
10.0 out of 10, Exceptional, (25 reviews)
"Amazing place to stay! Cozy, quiet, everything needed for a relaxing overnight stay! This trip was for a quick work things, but we’ll definitely be finding the time to come back to relax and take in the sights! Will definitely plan to stay here again! "
United States
Stephen W.
The price is AED 367
AED 643 total
includes taxes & fees
23 Jun - 24 Jun
Meadowview Guest House
TV

The Outdoorsman

The Outdoorsman
Hillsboro
8.0 out of 10, Very Good, (10 reviews)
"Clean and very quiet stay"
United States
Mindy
The price is AED 514
AED 625 total
includes taxes & fees
22 Jun - 23 Jun
The Outdoorsman
Terrace/patio

Peaceful cabin with spectacular river and scenic views.

Peaceful cabin with spectacular river and scenic views.
Adams County
9.8 out of 10, Exceptional, (33 reviews)
"Great location. "
United States
John S.
The price is AED 889
AED 1,517 total
includes taxes & fees
29 Jun - 30 Jun
Peaceful cabin with spectacular river and scenic views.
Terrace/patio

The Cabin at 114 Main Street

The Cabin at 114 Main Street
Augusta
9.6 out of 10, Exceptional, (36 reviews)
"I have stayed here twice and bother stays were great"
United States
Tiffany B.
The price is AED 511
AED 848 total
includes taxes & fees
23 Jun - 24 Jun
The Cabin at 114 Main Street
Smart TV

The Beach House

The Beach House
Hillsboro
7.8 out of 10, Good, (7 reviews)
"Great place to stay for a couple or just a single person weekend hunting or fishing trip!"
United States
Austin B.
The price is AED 459
AED 566 total
includes taxes & fees
22 Jun - 23 Jun
The Beach House
Living area

The White Stag

The White Stag
Hillsboro
7.6 out of 10, Good, (9 reviews)
"Place was cozy and beds were comfortable."
United States
Gavin D.
The price is AED 496
AED 605 total
includes taxes & fees
28 Jun - 29 Jun
The White Stag
Exterior

Glamping Cabin | Huge Window | Nature Lovers Dream

Glamping Cabin | Huge Window | Nature Lovers Dream
Green Township
9.8 out of 10, Exceptional, (9 reviews)
"We had a spectacular stay! Comfortable, Quiet, and Clean!Only a small suggestion Put a handle on the inside of the screen door and WD-40 the big door on cabin 1."
United Kingdom
Abby M.
The price is AED 253
AED 419 total
includes taxes & fees
22 Jun - 23 Jun
Glamping Cabin | Huge Window | Nature Lovers Dream
Interior

Tom & Jerri's Rustic Cabin located on the lake

Tom & Jerri's Rustic Cabin located on the lake
Hamersville
10.0 out of 10, Exceptional, (14 reviews)
"Very cute cabin on the lake! Great stay while at the ball fields! "
United States
Malia P.
The price is AED 569
AED 839 total
includes taxes & fees
25 Jun - 26 Jun
Tom & Jerri's Rustic Cabin located on the lake
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

Super 8 by Wyndham Maysville KY

Super 8 by Wyndham Maysville KY

8/10 Good
"This property is exactly what one would expect for the price. No frills. The morning breakfast was nice as was the coffee."
douglas 1-night trip
Posted 1 hour ago
Super 8 by Wyndham Maysville KY

Frequently asked questions

Can I find vacation rentals in Winchester?

Yes, we offer vacation rentals close to top attractions in Winchester, or you can go with a more secluded option if you want a relaxing place to stay.

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

LAKE HOUSE ON ROCKY FORK LAKE MOUNTAIN VIEW DR!: Visitors like this Winchester vacation home rental. It is located on a lake and has a patio, a selection of games, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and an oven, so you can cook with friends or family.

What’s there to see and do in Winchester?

While you're exploring the area, Rocky Fork Lake and Ripley Lions Club Community Park are a couple of picturesque spots to get outside and enjoy nature. In the larger area, you’ll find Adams Lake State Park and Serpent Mound.

What’s a vacation rental in Winchester like?

Vacation rentals are private properties you can stay in for a few days or a quick weekend in Winchester. Vacation rentals offer extras like kitchens and laundry facilities so you'll feel right at home. If you're concerned about cleanliness, vacation rentals can offer a sense of seclusion away from public hotel elevators and lobbies bustling with people while still allowing you the experience of travel. You'll also get more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is an attractive choice for small groups.