Winchester Vacation Rentals

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Check prices for these dates

In two weeks
Oct 31 - Nov 2
In two months
Dec 12 - Dec 14
In three months
Jan 9 - Jan 11
In four months
Feb 6 - Feb 8

Vacation Rentals in Winchester

Rustic Cabin with modern amenities and 1 acre stocked Fishing Lake !
Exterior
Rustic Cabin with modern amenities and 1 acre stocked Fishing Lake !
10.0 out of 10, Exceptional, (273)
"Great get away for few days. Cabin well stocked with everything you needed."
Rustic Cabin with modern amenities and 1 acre stocked Fishing Lake !
Cozy private getaway built for couples to reconnect !!
Interior
Cozy private getaway built for couples to reconnect !!
10.0 out of 10, Exceptional, (48)
"Beautiful home, quiet surroundings, awesome stay, loved this place."
Cozy private getaway built for couples to reconnect !!
Get away from it all! Restored 1800 log cabin on 40 acres - NO cleaning fee!
Outdoor dining
Get away from it all! Restored 1800 log cabin on 40 acres - NO cleaning fee!
10.0 out of 10, Exceptional, (336)
"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!
McKeever Mansion-9,000 sq ft. Perfect for corporate, families, or special events
Oven, stovetop, dishwasher
McKeever Mansion-9,000 sq ft. Perfect for corporate, families, or special events
10.0 out of 10, Exceptional, (41)
"Great place to host a reunion for large groups. Well stocked house. "Grandma's pizza" nearby has good pizza."
McKeever Mansion-9,000 sq ft. Perfect for corporate, families, or special events
Home away from Home! - 1BR apartment in Maysville
1 bedroom
Home away from Home! - 1BR apartment in Maysville
10.0 out of 10, Exceptional, (10)
"Wonderful apartment. Will book again next time we come to visit our family."
The price is ￥12,851
￥16,216 total
includes taxes & fees
Oct 16 - Oct 17
Home away from Home! - 1BR apartment in Maysville
The Angler
Microwave, oven, stovetop
The Angler
9.8 out of 10, Exceptional, (7)
"Outside not exactly what we were expecting, cabin was okay kitchen missing a few things but made do with what was there. Bedrooms looked to be somewhat under construction (screws sticking out, things laying around maybe wall decor or something missing). Beds and pillows very nice was comfortable. Host was very nice and answered my questions and such. Very noisy and loud on Saturday night into morning hours, maybe the time of year when we stayed. Overall decent place may stay again in a different...
The Angler
Cozy newly remodeled camper with hot tub and fire pit close to hiking/kayaking
Exterior
Cozy newly remodeled camper with hot tub and fire pit close to hiking/kayaking
10.0 out of 10, Exceptional, (40)
"Close to Serpent Mound. Relaxing and peaceful. "
Cozy newly remodeled camper with hot tub and fire pit close to hiking/kayaking
Private cabin on 80 acre farm in Adams County Ohio
1 bedroom, WiFi, bed sheets
Private cabin on 80 acre farm in Adams County Ohio
10.0 out of 10, Exceptional, (19)
"Beautiful cabin and property. Very peaceful and quiet."
Private cabin on 80 acre farm in Adams County Ohio
White Oak Cottage Sleeps 4
Property grounds
White Oak Cottage Sleeps 4
8.8 out of 10, Excellent, (5)
"The place was quaint, beautiful, and clean. The only reason I didn’t give 5 stars was the communication. Maybe it was a fluke, but I sent a message the morning of check in stating I never received an email with the check in information. After driving the 4 1/2 hours to the location, I had to finally look up the property name to call them and ask for information. I then did receive texts and the check in email. Other than that, we really enjoyed our stay, just not the stress of lack of contact...
White Oak Cottage Sleeps 4
Nature's Nook Cabin
Property grounds
Nature's Nook Cabin
9.8 out of 10, Exceptional, (79)
"This is the 3rd time we stay at this cabins clean, comfortable, Jacuzzi, fire pit amazing!!"
Nature's Nook Cabin
Peaceful cabin with spectacular river and scenic views.
Terrace/patio
Peaceful cabin with spectacular river and scenic views.
9.8 out of 10, Exceptional, (23)
"Cozy cabin with a great view"
The price is ￥32,929
￥54,889 total
includes taxes & fees
Oct 16 - Oct 17
Peaceful cabin with spectacular river and scenic views.
Peaceful historic log cabin getaway on 40 acres - NO cleaning fee!
Exterior
Peaceful historic log cabin getaway on 40 acres - NO cleaning fee!
10.0 out of 10, Exceptional, (108)
"Great place to get away. "
Peaceful historic log cabin getaway on 40 acres - NO cleaning fee!
Unique stay, hot tub, secluded
Interior
Unique stay, hot tub, secluded
9.2 out of 10, Wonderful, (15)
"Property was clean and a unique property. "
The price is ￥18,377
￥38,682 total
includes taxes & fees
Oct 15 - Oct 16
Unique stay, hot tub, secluded
Country Cabin in Amish Country
Fridge, microwave, oven
Country Cabin in Amish Country
9.8 out of 10, Exceptional, (11)
"The cabin was absolutely gorgeous. I would recommend it to all of my friends "
The price is ￥18,899
￥31,977 total
includes taxes & fees
Oct 19 - Oct 20
Country Cabin in Amish Country
Secluded in Amish Country and peaceful
Books
Secluded in Amish Country and peaceful
9.6 out of 10, Exceptional, (25)
"Nice clean quiet place to stay, would stay there again if in the area."
The price is ￥18,899
￥30,994 total
includes taxes & fees
Oct 23 - Oct 24
Secluded in Amish Country and peaceful
Secluded cabin located in Amish country
Property grounds
Secluded cabin located in Amish country
10.0 out of 10, Exceptional, (91)
"Great place to getaway from it all! "
Secluded cabin located in Amish country
Glamping Cabin | Huge Window | Tree House Feel
Property grounds
Glamping Cabin | Huge Window | Tree House Feel
9.2 out of 10, Wonderful, (18)
"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"
The price is ￥10,432
￥17,236 total
includes taxes & fees
Oct 15 - Oct 16
Glamping Cabin | Huge Window | Tree House Feel
Glamping Cabin | Huge Window | Over a Creek
Property grounds
Glamping Cabin | Huge Window | Over a Creek
10.0 out of 10, Exceptional, (6)
"Beautiful location ."
The price is ￥10,432
￥17,236 total
includes taxes & fees
Oct 15 - Oct 16
Glamping Cabin | Huge Window | Over a Creek
Griffis Game Hunting and/or Getaway
Exterior
Griffis Game Hunting and/or Getaway
9.8 out of 10, Exceptional, (27)
"Awesome cabin. Super clean and fun!"
The price is ￥20,565
￥33,329 total
includes taxes & fees
Oct 15 - Oct 16
Griffis Game Hunting and/or Getaway
Peaceful 8 Bedroom 5 Bath w/patio bar-grill and swimming pond
Exterior
Peaceful 8 Bedroom 5 Bath w/patio bar-grill and swimming pond
10.0 out of 10, Exceptional, (29)
"The house was great especially for such a large group. We do family vacation every year and this is definitely one we would stay at again "
Peaceful 8 Bedroom 5 Bath w/patio bar-grill and swimming pond
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

Peaceful cabin with spectacular river and scenic views.

Peaceful cabin with spectacular river and scenic views.

10/10 Excellent
"Great location. "
John S. 2-night trip
Posted 2 days ago
Peaceful cabin with spectacular river and scenic views.

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?

McKeever Mansion-9,000 sq ft. Perfect for corporate, families, or special events: Visitors like this Winchester vacation home rental. It comes with laundry facilities so you can feel at home during your trip. Kitchen amenities like a dishwasher and a stovetop can make your vacation run smoothly.

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 Serpent Mound and Hillsboro Elks Country Club.

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.