Winchester Vacation Rentals

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Check prices for these dates

In two weeks
Mar 13 - Mar 15
In two months
Apr 24 - Apr 26
In three months
May 22 - May 24
In four months
Jun 19 - Jun 21

Our top choices for Winchester vacation rentals

Property grounds

Cabin in Green Township

Glamping Cabin | Huge Window | Over a Creek
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 ￥10,758
￥17,774 total
includes taxes & fees
Mar 4 - Mar 5
Glamping Cabin | Huge Window | Over a Creek
Property grounds

Cabin in Green Township

Glamping Cabin | Huge Window | Cliff and Animal Views
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 ￥10,758
￥17,774 total
includes taxes & fees
Mar 4 - Mar 5
Glamping Cabin | Huge Window | Cliff and Animal Views
Property grounds

Cabin in Green Township

Glamping Cabin | Huge Window | Tree House Feel
9.0 out of 10, Wonderful, (19 reviews)
"The perfect place to connect with nature and enjoy a beautiful landscape the attention was great the beautiful place the super comfortable cabin I would come back again"
Mexico
Víctor Manuel
The price is ￥10,758
￥17,774 total
includes taxes & fees
Mar 4 - Mar 5
Glamping Cabin | Huge Window | Tree House Feel
Interior

Cabin in Peebles

Secluded in Amish Country and peaceful
9.8 out of 10, Exceptional, (28 reviews)
"Excellent place "
United States
Casey J.
The price is ￥17,150
￥29,467 total
includes taxes & fees
Feb 27 - Feb 28
Secluded in Amish Country and peaceful
Interior

Cabin in Hamersville

Cowboy Saloon Cabin
9.4 out of 10, Exceptional, (20 reviews)
"Clean & cool little place."
United States
Stephen
The price is ￥21,048
￥32,133 total
includes taxes & fees
Feb 27 - Feb 28
Cowboy Saloon Cabin
Smart TV

Cabin in Hillsboro

The Angler
8.4 out of 10, Very Good, (10 reviews)
"Clean and great for a couple of fisherman enjoying the lake and surrounding area. "
United States
Jerry P.
The price is ￥15,589
￥19,838 total
includes taxes & fees
Mar 10 - Mar 11
The Angler
Interior

Cabin in West Union

Bear Necessities Cabin - What Else Do You Need?
10.0 out of 10, Exceptional, (9 reviews)
"Very clean cabin and very cozy!"
United States
Debbie F.
The price is ￥13,252
￥25,126 total
includes taxes & fees
Mar 4 - Mar 5
Bear Necessities Cabin - What Else Do You Need?
Fridge, microwave, oven, stovetop

Cabin in West Union

Griffis Game Hunting and/or Getaway
9.8 out of 10, Exceptional, (31 reviews)
"Super nice host, very clean cabin."
United States
BRAD T.
The price is ￥21,048
￥34,579 total
includes taxes & fees
Mar 4 - Mar 5
Griffis Game Hunting and/or Getaway
Living area

Cabin in Hillsboro

The White Stag
7.4 out of 10, Good, (8 reviews)
"We CD enjoyed our stay. It was spacious and cozy. The large bed is very tall so take a step stool. Mattresess are very confy. "
United States
Danelia
The price is ￥17,566
￥21,963 total
includes taxes & fees
Feb 27 - Feb 28
The White Stag
Exterior detail

Cabin in Hamersville

Big Mike's Cabin on the lake, next to ball diamonds nestled in 3 -cabin village
9.6 out of 10, Exceptional, (23 reviews)
"This was a great stay. The property owners were fabulous. Definitely coming back ."
United States
Atonenent R.
The price is ￥19,489
￥30,325 total
includes taxes & fees
Feb 27 - Feb 28
Big Mike's Cabin on the lake, next to ball diamonds nestled in 3 -cabin village
Fridge, microwave, oven

Cabin in Peebles

Country Cabin in Amish Country
9.8 out of 10, Exceptional, (13 reviews)
"Beautiful clean place "
United States
Casey J.
The price is ￥16,395
￥29,089 total
includes taxes & fees
Mar 22 - Mar 23
Country Cabin in Amish Country
Terrace/patio

Cabin in Green Township

Sleeps 4| Private Bathroom | Stunning Views
6.8 out of 10, (3 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 ￥21,048
￥24,166 total
includes taxes & fees
Mar 3 - Mar 4
Sleeps 4| Private Bathroom | Stunning Views
Outdoor spa tub

Vacation Home in Georgetown

White Oak Cottage Sleeps 4
9.2 out of 10, Wonderful, (9 reviews)
"I truly enjoyed how clean and stocked the cabin was they had everything you could possibly need and some me and my family fully enjoyed the stay "
United States
Austin C.
The price is ￥17,025
￥28,095 total
includes taxes & fees
Mar 2 - Mar 3
White Oak Cottage Sleeps 4
Terrace/patio

Cabin in Adams County

Peaceful cabin with spectacular river and scenic views.
9.8 out of 10, Exceptional, (29 reviews)
"Great location. "
United States
John S.
The price is ￥37,730
￥60,795 total
includes taxes & fees
Feb 27 - Feb 28
Peaceful cabin with spectacular river and scenic views.
Outdoor spa tub

Guesthouse in Hillsboro

Meadowview Guest House
10.0 out of 10, Exceptional, (22 reviews)
"I was out there for a wedding and this place was great for a weekend trip."
United States
L
The price is ￥18,241
￥30,090 total
includes taxes & fees
Mar 1 - Mar 2
Meadowview Guest House
Interior

Cabin in Hamersville

Tom & Jerri's Rustic Cabin located on the lake
10.0 out of 10, Exceptional, (13 reviews)
"Very cute cabin on the lake! Great stay while at the ball fields! "
United States
Malia P.
The price is ￥24,166
￥35,126 total
includes taxes & fees
Feb 27 - Feb 28
Tom & Jerri's Rustic Cabin located on the lake
Exterior

Cabin in Green Township

Glamping Cabin | Huge Window | Nature Lovers Dream
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 ￥10,758
￥17,774 total
includes taxes & fees
Mar 4 - Mar 5
Glamping Cabin | Huge Window | Nature Lovers Dream
Property grounds

Cabin in Blue Creek

Sleeps 12| Private Bathroom | Stunning Views
10.0 out of 10, Exceptional, (7 reviews)
"This cabin was exactly what we were looking for: Cozy, peaceful, clean, comfortable and all the amenities. Located near several great hiking spots within a short drive. Great indoor and outdoor space. Host was very friendly and responsive. Highly recommend this place!"
United States
Amy H.
The price is ￥38,978
￥48,021 total
includes taxes & fees
Mar 19 - Mar 20
Sleeps 12| Private Bathroom | Stunning Views
Exterior

Cabin in Green Township

Glamping Cabin | Huge Window | Valley and Cliff Views
10.0 out of 10, Exceptional, (2 reviews)
"Property owners were very welcoming. The tree house and property were well maintained. "
United States
Marci
The price is ￥10,758
￥17,774 total
includes taxes & fees
Mar 1 - Mar 2
Glamping Cabin | Huge Window | Valley and Cliff Views
Living area

Apartment in Augusta

Charming Retreat: Walk to Distillery & River
10.0 out of 10, Exceptional, (2 reviews)
"Rodney and Ruth were very responsive. Adorable space within walking distance to the Augusta Distillery."
United States
Misty
The price is ￥16,994
￥27,374 total
includes taxes & fees
Mar 5 - Mar 6
Charming Retreat: Walk to Distillery & River
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

Days Inn by Wyndham Hillsboro

Days Inn by Wyndham Hillsboro

10/10 Excellent
"Good room staff was very helpful. Nice place to stay!"
Jill 1-night trip
Posted 6 days ago
Days Inn by Wyndham Hillsboro

Find out more about Winchester

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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?

Unique and secluded A frame home on 31 acres with hot tub.: Visitors like this Winchester vacation home rental. It is located on a river and has a fireplace, a balcony, 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 stovetop, and a microwave, so you can cook with friends or family. It offers a garden, a selection of games, and a hot tub so you can immerse yourself in your vacation.

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.