A historic downtown area with a prominent clock tower and a green-roofed building.

Winchester Holiday Rentals

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Our top choices for Winchester holiday rentals

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 NZ$200
includes taxes & fees
5 July - 6 July
Glamping Cabin | Huge Window | Over a Creek

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 NZ$200
includes taxes & fees
5 July - 6 July
Glamping Cabin | Huge Window | Cliff and Animal Views

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 NZ$315
includes taxes & fees
5 July - 6 July
Stout Cabin w/ Fire Pit: 1 Mi to Ohio River!

Glamping Cabin | Huge Window | Tree House Feel

Glamping Cabin | Huge Window | Tree House Feel
Blue Creek
8.6 out of 10, Excellent, (21 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 NZ$200
includes taxes & fees
5 July - 6 July
Glamping Cabin | Huge Window | Tree House Feel

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 NZ$316
includes taxes & fees
5 July - 6 July
Stout Cabin w/ Fire Pit: 1 Mi to Ohio River!

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 NZ$271
includes taxes & fees
6 July - 7 July
Sleeps 4| Private Bathroom | Stunning Views

Secluded in Amish Country and peaceful

Secluded in Amish Country and peaceful
Peebles
9.8 out of 10, Exceptional, (31 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 NZ$315
includes taxes & fees
3 Aug - 4 Aug
Secluded in Amish Country and peaceful

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 NZ$300
includes taxes & fees
6 July - 7 July
Bear Necessities Cabin - What Else Do You Need?

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 NZ$326
includes taxes & fees
15 July - 16 July
Country Cabin in Amish Country

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 NZ$380
includes taxes & fees
6 July - 7 July
Griffis Game Hunting and/or Getaway

1 Bed/1 Bath Guest House

1 Bed/1 Bath Guest House
Hillsboro
9.8 out of 10, Exceptional, (6 reviews)
The price is NZ$243
includes taxes & fees
9 July - 10 July
1 Bed/1 Bath Guest House

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 NZ$359
includes taxes & fees
5 July - 6 July
Cowboy Saloon Cabin

Old world charm, peace and quiet.

Old world charm, peace and quiet.
Dover
The price is NZ$287
includes taxes & fees
6 July - 7 July
Old world charm, peace and quiet.

Meadowview Guest House

Meadowview Guest House
Hillsboro
10.0 out of 10, Exceptional, (26 reviews)
"I was out there for a wedding and this place was great for a weekend trip."
United States
L
The price is NZ$306
includes taxes & fees
5 July - 6 July
Meadowview Guest House

Big Mike's Cabin on the lake, next to ball diamonds nestled in 3 -cabin village

Big Mike's Cabin on the lake, next to ball diamonds nestled in 3 -cabin village
Hamersville
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 NZ$339
includes taxes & fees
6 July - 7 July
Big Mike's Cabin on the lake, next to ball diamonds nestled in 3 -cabin village

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 NZ$297
includes taxes & fees
10 July - 11 July
The White Stag

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 NZ$410
includes taxes & fees
5 July - 6 July
The Cabin at 114 Main Street

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 NZ$206
includes taxes & fees
7 July - 8 July
The Huntsmen

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 NZ$707
includes taxes & fees
16 July - 17 July
Peaceful cabin with spectacular river and scenic views.

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 NZ$270
includes taxes & fees
7 July - 8 July
The Beach House
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

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, 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 NZ$200 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

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?

Perfect Tiny Home Getaway!: This holiday home rental outside of Winchester offers a patio, a garden and air conditioning to help you feel perfectly comfortable in your new surroundings. You and your friends and family can relax into your holiday with amenities such as 1 hot tub.

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.