Winchester Holiday Rentals

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Check prices for these dates

In two weeks
12 Jun - 14 Jun
In two months
24 Jul - 26 Jul
In three months
21 Aug - 23 Aug
In four months
18 Sept - 20 Sept

Our top choices for Winchester holiday rentals

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 HK$721
HK$1,404 total
includes taxes & fees
30 May - 31 May
Stout Cabin w/ Fire Pit: 1 Mi to Ohio River!
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)
"Loved watching the storm through the big window and listening to the rain on the roof. "
United States
Crystal A.
The price is HK$541
HK$893 total
includes taxes & fees
31 May - 1 Jun
Glamping Cabin | Huge Window | Over a Creek
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 HK$541
HK$893 total
includes taxes & fees
31 May - 1 Jun
Glamping Cabin | Huge Window | Cliff and Animal Views
Property grounds

Glamping Cabin | Huge Window | Tree House Feel

Glamping Cabin | Huge Window | Tree House Feel
Green Township
8.8 out of 10, Excellent, (20 reviews)
"The property is very remote, secluded and quiet. It is a pet friendly property that our dog very much enjoyed. For hikers this is a great location. We were very unlucky with the weather, so no fire pit or BBQing due to torrential rain (no one can control that). Amenities are solid. It is glamping. There is a gas station approx. 10 minutes away that serves some solid breakfast…Portsmouth is about 45 minutes away for some dinner options."
United States
Stuart
The price is HK$541
HK$893 total
includes taxes & fees
31 May - 1 Jun
Glamping Cabin | Huge Window | Tree House Feel
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 HK$642
HK$1,411 total
includes taxes & fees
30 May - 31 May
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 HK$620
HK$1,214 total
includes taxes & fees
1 Jun - 2 Jun
Bear Necessities Cabin - What Else Do You Need?
Interior

Secluded in Amish Country and peaceful

Secluded in Amish Country and peaceful
Peebles
9.8 out of 10, Exceptional, (29 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 HK$823
HK$1,410 total
includes taxes & fees
31 May - 1 Jun
Secluded in Amish Country and peaceful
1 bedroom, WiFi

Home away from Home! - 1BR apartment in Maysville

Home away from Home! - 1BR apartment in Maysville
Maysville
10.0 out of 10, Exceptional, (14 reviews)
"Amazing stay. We would definitely recommend this place to anyone!"
United States
John H.
The price is HK$666
HK$840 total
includes taxes & fees
12 Jun - 13 Jun
Home away from Home! - 1BR apartment in Maysville
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 HK$529
HK$934 total
includes taxes & fees
1 Jun - 2 Jun
1 Bed/1 Bath Guest House
Terrace/patio

Sleeps 4| Private Bathroom | Stunning Views

Sleeps 4| Private Bathroom | Stunning Views
Green Township
7.2 out of 10, Good, (5 reviews)
"Yes, it would have been perfect for leashed pets. Cabin was very cozy and fit our needs well. One thing we did notice that would've been great if they had some bowls for mixing pancakes and such. "
United States
Dane C.
The price is HK$1,058
HK$1,214 total
includes taxes & fees
31 May - 1 Jun
Sleeps 4| Private Bathroom | Stunning Views
Fridge, microwave, oven

Country Cabin in Amish Country

Country Cabin in Amish Country
Peebles
9.8 out of 10, Exceptional, (15 reviews)
"Beautiful clean place "
United States
Casey J.
The price is HK$823
HK$1,459 total
includes taxes & fees
31 May - 1 Jun
Country Cabin in Amish Country
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 HK$1,058
HK$1,714 total
includes taxes & fees
1 Jun - 2 Jun
Griffis Game Hunting and/or Getaway
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 HK$705
HK$1,300 total
includes taxes & fees
31 May - 1 Jun
Meadowview Guest House
Exterior

“Serenity Now” a 2BR country home in the heart of Amish Country

“Serenity Now” a 2BR country home in the heart of Amish Country
West Union
The price is HK$635
HK$1,239 total
includes taxes & fees
25 Jun - 26 Jun
“Serenity Now” a 2BR country home in the heart of Amish Country
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 HK$1,058
HK$1,622 total
includes taxes & fees
2 Jun - 3 Jun
Cowboy Saloon Cabin
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, (30 reviews)
"Great location. "
United States
John S.
The price is HK$1,706
HK$2,844 total
includes taxes & fees
2 Jun - 3 Jun
Peaceful cabin with spectacular river and scenic views.
Interior

Harvest Haven Grain Bin

Harvest Haven Grain Bin
Peebles
9.0 out of 10, Wonderful, (23 reviews)
"Very nice stay. "
United States
Jennifer J.
The price is HK$1,046
HK$2,064 total
includes taxes & fees
22 Jun - 23 Jun
Harvest Haven Grain Bin
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 HK$697
HK$904 total
includes taxes & fees
2 Jun - 3 Jun
The Huntsmen
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 HK$1,058
HK$1,291 total
includes taxes & fees
31 May - 1 Jun
The White Stag
TV

The Outdoorsman

The Outdoorsman
Hillsboro
8.0 out of 10, Very good, (9 reviews)
"Clean and very quiet stay"
United States
Mindy
The Outdoorsman
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

Beverly hills inn

Beverly hills inn

4/10 Poor
"Greatly aging facility. Price was great, but room was not. Fairly clean in main area, but bathroom was not. Decided to forego the restaurant—in general the area was run down enough that we began to not trust the cleanliness."
Carla 1-night trip
Posted 3 hours ago
Beverly hills inn

Find out more about Winchester

Search for holiday rentals in Winchester on Expedia! You can easily find your home rentals, villas, holiday apartments in Winchester using one of the methods below:

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Look no further and take a look at our great range of rental properties in Winchester!

Frequently asked questions

Can I find 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.

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

Unique and secluded A frame home on 31 acres with hot tub.: This holiday home rental outside of Winchester is located on a river, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a stovetop and a microwave, so that you can cook with friends or family. It offers a garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday.

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 wider area, you’ll find Adams Lake State Park and Serpent Mound.

What’s a holiday rental in Winchester like?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Winchester. Holiday rentals feature amenities such as laundry facilities and kitchens so you'll feel just like you're staying in your own home. If you're concerned about a clean environment, holiday rentals can offer a sense of privacy away from public hotel lifts and lobbies packed with people while still allowing you the enjoyment of travel. You'll also find more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a popular option for families.