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Top Holiday Rentals in Winchester

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

10.0 out of 10, Exceptional, (270)
"Lovely home fully stocked to cover all your needs. "
Rustic Cabin with modern amenities and 1 acre stocked Fishing Lake !

Get away from it all! Restored 1800 log cabin on 40 acres - NO cleaning fee!

10.0 out of 10, Exceptional, (329)
"Peaceful and beautiful. The cabin feels like home so comfortable And clean. If you want a quiet place away from the city this is a great place. "
Get away from it all! Restored 1800 log cabin on 40 acres - NO cleaning fee!

Cowboy Saloon Cabin

9.4 out of 10, Exceptional, (15)
"The utensils were dirty, a lot of bugs, spider webs. I think the porch's should of been swept off and just cleaned a little better. Windows were dirty. Inside cabin was very nice and clean, except for the utensils. We will definately visit again. Thank you. Lianne"
The price is £152
includes taxes & fees
13 Aug - 14 Aug
Cowboy Saloon Cabin

Cozy private getaway built for couples to reconnect !!

10.0 out of 10, Exceptional, (45)
"It’s a great place in the countryside nice and peaceful. You don’t have the traffic or street lights great place to relax."
Cozy private getaway built for couples to reconnect !!

Cozy newly remodeled camper with hot tub and fire pit close to hiking/kayaking

10.0 out of 10, Exceptional, (35)
"Ken & Cindy were gracious hosts who thought of everything for their guests. They were very thoughtful in what they stocked for guests. Their dogs frequently came to visit- a joy for our pup! Wonderful little place to stay. We would definitely stay here again. "
Cozy newly remodeled camper with hot tub and fire pit close to hiking/kayaking

The Angler

10.0 out of 10, Exceptional, (5)
The Angler

New 3 Bedroom Log Cabin nestled in the woods with one acre fishing lake .

10.0 out of 10, Exceptional, (139)
"Completely set up for all your conveniences very comfortable furniture! Ease of check in and check out!"
New 3 Bedroom Log Cabin nestled in the woods with one acre fishing lake .

Spacious 4-bedroom 19th Century home in historic downtown Maysville!

10.0 out of 10, Exceptional, (2)
"We were overly impressed by this property and the location. The house was emasculate and had such great character in every room. Check in and communication with the property own were top notch. The main areas in the town are all within short walking distance of the home. We will definitely look for this home again next year when we come back to Maysville. We won Oktoberfest king 2025 so we’ll definitely be back!"
Spacious 4-bedroom 19th Century home in historic downtown Maysville!

Peaceful historic log cabin getaway on 40 acres - NO cleaning fee!

10.0 out of 10, Exceptional, (104)
"Everything was great! Would stay here again. "
Peaceful historic log cabin getaway on 40 acres - NO cleaning fee!

Cozy Country Cabin close to West Union!

2.0 star property
10.0 out of 10, Exceptional, (19)
"The property was very clean and had everything we needed. We would stay again. "
Cozy Country Cabin close to West Union!

Tom & Jerri's Rustic Cabin located on the lake

10.0 out of 10, Exceptional, (13)
"Very cute cabin on the lake! Great stay while at the ball fields! "
Tom & Jerri's Rustic Cabin located on the lake

Peaceful 8 Bedroom 5 Bath w/patio bar-grill and swimming pond

10.0 out of 10, Exceptional, (27)
"The place was huge, clean, and amazing! Would recommend to anyone! "
Peaceful 8 Bedroom 5 Bath w/patio bar-grill and swimming pond

Private cabin on 80 acre farm in Adams County Ohio

10.0 out of 10, Exceptional, (18)
"The property was beautiful. The cabin was clean and well maintained. "
Private cabin on 80 acre farm in Adams County Ohio

TRANQUILITY AT ITS BEST!!! Amish-Built, Pond & Firepit on 6 Private Acres

10.0 out of 10, Exceptional, (108)
"so beautiful and peaceful!"
TRANQUILITY AT ITS BEST!!! Amish-Built, Pond & Firepit on 6 Private Acres

LAKE HOUSE ON ROCKY FORK!

9.4 out of 10, Exceptional, (30)
"Perfect spot for my family to get together for Christmas! Easy to get to, cozy and nice backyard cause I have dogs. Just a great place to stay!"
LAKE HOUSE ON ROCKY FORK!

The Manor at Maysville Golf Course View

9.8 out of 10, Exceptional, (22)
"Our families got together for a lovely Christmas gathering here. The house was beautifully decorated!"
The Manor at Maysville Golf Course View

10 min to Rocky Fork Lake ⏐ Gorgeous Peaceful Farm for Large Groups - two houses

10.0 out of 10, Exceptional, (2)
"We had the absolute best experience during our stay. The hosts’ incredible hospitality and servant hearted care for our group was stunning. We immediately booked another stay before we even checked out. It’s beautiful. It’s peaceful. It’s serene. Is an oasis to take a deep breath. We are so thankful to have found it. "
10 min to Rocky Fork Lake ⏐ Gorgeous Peaceful Farm for Large Groups - two houses

Amish-built cabin, serene and peaceful with pond and private dock for fishing.

10.0 out of 10, Exceptional, (21)
"The property was beautiful. The cabin was clean and well maintained. "
Amish-built cabin, serene and peaceful with pond and private dock for fishing.

Hunter Lodge (Secluded in Amish Country and peaceful)

10.0 out of 10, Exceptional, (36)
"Booked this place for my son and daughter in law for their honeymoon. He is in the Navy so he only had availability to go away for one night before he had to get back to his duty station. They really enjoyed the property and surrounding area. "
The price is £144
includes taxes & fees
17 Aug - 18 Aug
Hunter Lodge (Secluded in Amish Country and peaceful)

Unique stay, hot tub, secluded

9.4 out of 10, Exceptional, (11)
"Comfy beds and great hottub. It was so cute and unique to stay in a grain bin. Very nicely decorated and clean. "
The price is £195
includes taxes & fees
19 Aug - 20 Aug
Unique stay, hot tub, secluded
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

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?

Spacious 4-bedroom 19th Century home in historic downtown Maysville!: This holiday home rental outside of Winchester is located on a river, and offers a patio, air conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that 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 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 Serpent Mound and Hillsboro Elks Country Club.

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.