Winchester Vacation Rentals

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Vacation Rentals in Winchester

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

10.0 out of 10, Exceptional, (267)
"Lovely home fully stocked to cover all your needs. "
Rustic Cabin with modern amenities and 1 acre stocked Fishing Lake !

Cozy private getaway built for couples to reconnect !!

10.0 out of 10, Exceptional, (41)
"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 !!

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

10.0 out of 10, Exceptional, (137)
"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 .

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

10.0 out of 10, Exceptional, (327)
"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!

Secluded cabin located in Amish country

10.0 out of 10, Exceptional, (86)
"The cabin was beautiful as shown in the pics. It was stocked very well with anything you may need. I loved how it sits in the woods a bit. It’s a very relaxing setting, we enjoyed it very much. Very well kept inside and out. "
Secluded cabin located in Amish country

THE HEIGHT OF SERENITY!! Very Private, Pond & Firepit on 6 Acres. FREE WiFi

10.0 out of 10, Exceptional, (108)
"so beautiful and peaceful!"
THE HEIGHT OF SERENITY!! Very Private, Pond & Firepit on 6 Acres. FREE WiFi

Unique stay, hot tub, secluded

9.4 out of 10, Exceptional, (8)
"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 CA $167
CA $351 total
includes taxes & fees
Jul 30 - Jul 31
Unique stay, hot tub, secluded

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

10.0 out of 10, Exceptional, (26)
"The place was huge, clean, and amazing! Would recommend to anyone! "
Peaceful 8 Bedroom 5 Bath w/patio bar-grill and swimming pond

Cowboy Saloon Cabin

9.4 out of 10, Exceptional, (14)
"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 CA $185
CA $274 total
includes taxes & fees
Jul 29 - Jul 30
Cowboy Saloon Cabin

The Angler

10.0 out of 10, Exceptional, (4)
"The place was nice. The people who ran the place were very friendly and helpful "
The Angler

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

McKeever Mansion-9,000 sq ft. Perfect for corporate, families, or special events

10.0 out of 10, Exceptional, (37)
"Host is helpful and check in/out was a breeze!"
McKeever Mansion-9,000 sq ft. Perfect for corporate, families, or special events

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

10.0 out of 10, Exceptional, (102)
"Everything was great! Would stay here again. "
Peaceful historic log cabin getaway on 40 acres - NO cleaning fee!

The White Stag

7.0 out of 10, Good, (6)
"Very clean and felt safe. "
The White Stag

Peaceful cabin with spectacular river and scenic views.

9.8 out of 10, Exceptional, (15)
"Cozy cabin with a great view"
The price is CA $332
CA $537 total
includes taxes & fees
Aug 17 - Aug 18
Peaceful cabin with spectacular river and scenic views.

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

10.0 out of 10, Exceptional, (33)
"A great experience. Cindy Ken and the pups were great. Beautiful spot and Serpent Mound stones throw away. We'll be back."
Cozy newly remodeled camper with hot tub and fire pit close to hiking/kayaking

Glamping Cabin | Huge Window | Over a Creek

10.0 out of 10, Exceptional, (4)
"Beautiful location ."
The price is CA $130
CA $192 total
includes taxes & fees
Jul 29 - Jul 30
Glamping Cabin | Huge Window | Over a Creek

RELAXATION AT ITS BEST! Paradise & Tranquility Bordering Brush Creek Forest!!

9.8 out of 10, Exceptional, (138)
"The Sanctuary is our family go to place when we want to reconnect and relax. This was our 4th visit and it has always been clean, comfortable and has a well stocked kitchen for your cooking needs."
RELAXATION AT ITS BEST! Paradise & Tranquility Bordering Brush Creek Forest!!

LAKE HOUSE ON ROCKY FORK!

9.4 out of 10, Exceptional, (28)
"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 Bear Den (Secluded in Amish Country and peaceful)

10.0 out of 10, Exceptional, (33)
"Very clean. Great location "
The price is CA $144
CA $251 total
includes taxes & fees
Aug 3 - Aug 4
The Bear Den (Secluded in Amish Country and peaceful)
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 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?

Peaceful 8 Bedroom 5 Bath w/patio bar-grill and swimming pond: Visitors like this Winchester vacation home rental. It is located in a rural location and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 9 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games.

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 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.