Winchester Holiday Rentals

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Check prices for these dates

In two weeks
5 Dec - 7 Dec
In two months
16 Jan - 18 Jan
In three months
13 Feb - 15 Feb
In four months
13 Mar - 15 Mar

Holiday Rentals in Winchester

Exterior
Rustic Cabin with modern amenities and 1 acre stocked Fishing Lake !

Cabin in Winchester

10.0 out of 10, Exceptional, (275)
"Easy check in .. hosts was very friendly and outgoing. Loved our stay and will be back !! "
United States
JAMES G.
Rustic Cabin with modern amenities and 1 acre stocked Fishing Lake !
Front of property
Ohio Starlight Glamping Cabins

Cabin in Rome

2.0 star property
10.0 out of 10, Exceptional, (1)
"This place is awesome. "
United States
Zacheryah
Ohio Starlight Glamping Cabins
Interior
Unique stay, hot tub, secluded

Holiday Home in Peebles

9.2 out of 10, Wonderful, (17)
"Property was clean and a unique property. "
United States
Robert
The price is HK$946
HK$1,991 total
includes taxes & fees
24 Nov - 25 Nov
Unique stay, hot tub, secluded
Terrace/patio
Cowboy Saloon Cabin

Cabin in Hamersville

9.6 out of 10, Exceptional, (17)
"Cute, cozy, and clean. Stayed 2 nights; enjoyed fishing off the back deck. "
United States
Cynthia C.
The price is HK$1,051
HK$1,541 total
includes taxes & fees
24 Nov - 25 Nov
Cowboy Saloon Cabin
Oven, stovetop, dishwasher
McKeever Mansion-9,000 sq ft. Perfect for corporate, families, or special events

Holiday Home in Williamsburg

10.0 out of 10, Exceptional, (42)
"Great place to host a reunion for large groups. Well stocked house. "Grandma's pizza" nearby has good pizza."
United States
Kaushik P.
McKeever Mansion-9,000 sq ft. Perfect for corporate, families, or special events
Fridge, microwave, stovetop, coffee/tea maker
Bear Necessities Cabin - What Else Do You Need?

Cabin in West Union

10.0 out of 10, Exceptional, (7)
"Great little spot! Cabin is super nice inside and out."
United States
Jason M.
The price is HK$662
HK$1,254 total
includes taxes & fees
24 Nov - 25 Nov
Bear Necessities Cabin - What Else Do You Need?
Outdoor dining
Get away from it all! Restored 1800 log cabin on 40 acres - NO cleaning fee!

Cabin in Blue Creek

10.0 out of 10, Exceptional, (338)
"This place is absolutely gorgeous! My parents fell in love with it! It is excellent for stargazing, and there are tons of butterflies and lightning bugs. There are beautiful deer that graze around. The hosts are very attentive and wonderful! "
United States
Whitney A.
Get away from it all! Restored 1800 log cabin on 40 acres - NO cleaning fee!
Terrace/patio
Sunset Cabin-Couple's only Hot Tub Getaway

Holiday Home in Hillsboro

9.6 out of 10, Exceptional, (5)
Sunset Cabin-Couple's only Hot Tub Getaway
Terrace/patio
Peaceful cabin with spectacular river and scenic views.

Cabin in Adams County

9.8 out of 10, Exceptional, (27)
"The cabin was very clean, comfortable and nicely furnished. The view of the river from the porch was spectacular, the hot tub was nice and clean and worked great. This was the most well stocked VRBO I have ever stayed in. Our host Christopher was very cool and hospitable. We'd definitely stay there again and recommend it to others. "
United States
Kimberly H.
The price is HK$1,695
HK$2,826 total
includes taxes & fees
24 Nov - 25 Nov
Peaceful cabin with spectacular river and scenic views.
Exterior
Flash Lodge Add-on Cabin-Pamela's Diamond

Cabin in Hamersville

9.6 out of 10, Exceptional, (27)
"The loveliest little cabin, all the extras to make your trip easy"
United States
jeanette
The price is HK$701
HK$1,168 total
includes taxes & fees
24 Nov - 25 Nov
Flash Lodge Add-on Cabin-Pamela's Diamond
Property grounds
Nature's Nook Cabin

Cabin in Hillsboro

9.8 out of 10, Exceptional, (80)
"One of our favorite places to stay!"
United States
Susan Z.
Nature's Nook Cabin
Property grounds
Glamping Cabin | Huge Window | Over a Creek

Cabin in Green Township

9.8 out of 10, Exceptional, (7)
"Beautiful location ."
United States
Shelly R.
The price is HK$537
HK$887 total
includes taxes & fees
24 Nov - 25 Nov
Glamping Cabin | Huge Window | Over a Creek
Exterior
Griffis Game Hunting and/or Getaway

Cabin in West Union

9.8 out of 10, Exceptional, (27)
"Awesome cabin. Super clean and fun!"
United States
Phillip M.
The price is HK$1,051
HK$1,726 total
includes taxes & fees
3 Dec - 4 Dec
Griffis Game Hunting and/or Getaway
Exterior
Glamping Cabin | Huge Window | Cliff and Animal Views

Cabin in Green Township

10.0 out of 10, Exceptional, (1)
"We had a lovely time at this cabin -- I stayed with my sweetheart and our doberman puppy, and the place was quiet, rustic, beautiful. I would be happy to come back here again. Our dog met goats for the first time! That was hilarious and unexpected. There's a beautiful horse on the property, and we had a nice time giving him scritches on the neck. The price was lovely for the accommodation, and the huge window looking out on the wooded cliff was a wonderful bonus. Thank you!"
United States
Olga
The price is HK$537
HK$887 total
includes taxes & fees
24 Nov - 25 Nov
Glamping Cabin | Huge Window | Cliff and Animal Views
Exterior
Peaceful historic log cabin getaway on 40 acres - NO cleaning fee!

Cabin in Blue Creek

10.0 out of 10, Exceptional, (110)
"Great place to get away. "
United States
JASON
Peaceful historic log cabin getaway on 40 acres - NO cleaning fee!
Exterior
Peaceful 8 Bedroom 5 Bath w/patio bar-grill and swimming pond

Holiday Home in Peebles

10.0 out of 10, Exceptional, (33)
"The house was as good as advertised. Everything was clean and ready to go when we arrived. Plenty of room for everyone, and tons of amenities. "
United States
Nick B.
Peaceful 8 Bedroom 5 Bath w/patio bar-grill and swimming pond
Microwave, oven, stovetop
The Angler

Cabin in Hillsboro

9.8 out of 10, Exceptional, (7)
"The property was clean and furnishings simple but comfortable."
United States
Margie R.
The price is HK$778
HK$990 total
includes taxes & fees
9 Dec - 10 Dec
The Angler
Interior
Sleepy Hollow Large 4 Bedroom Lakefront House in Rocky Fork Lake

Cabin in Hillsboro

2.0 star property
Sleepy Hollow Large 4 Bedroom Lakefront House in Rocky Fork Lake
Property grounds
Hunter Lodge (Secluded in Amish Country and peaceful)

Cabin in Peebles

10.0 out of 10, Exceptional, (40)
"The cabin was perfect for our short stay."
United States
Beth R.
The price is HK$973
HK$1,603 total
includes taxes & fees
24 Nov - 25 Nov
Hunter Lodge (Secluded in Amish Country and peaceful)
Interior
Cozy private getaway built for couples to reconnect !!

Cabin in West Union

10.0 out of 10, Exceptional, (51)
"Beautiful place to stay for a secluded weekend! The place was very clean and the hosts were very kind and accommodating, providing everything we need for the weekend as well as a few extras! Would definitely stay again!"
United States
Emily s.
Cozy private getaway built for couples to reconnect !!
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

10/10 Excellent
"Yes"
RICKEY 1-night trip
Posted 3 days ago
Super 8 by Wyndham Maysville KY

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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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 stay, hot tub, secluded: This holiday home rental outside of Winchester is located in the city centre, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. Make the most of Access to hot tub in this rental home to help you unwind.

What’s there to see and do in Winchester?

While you're exploring the area, Rocky Fork Lake State Park and Rocky Fork Lake 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.