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, (254)
"Our stay at this cabin was great! It had everything we needed and more. The location was very peaceful. We saw deer in the backyard. The cabin was beautiful. I highly recommend staying here! The only thing it needs is curtains in the bedrooms. Otherwise everything was fantastic and we would stay here again! Thanks so much! "
Rustic Cabin with modern amenities and 1 acre stocked Fishing Lake !
New 3 Bedroom Log Cabin nestled in the woods with one acre fishing lake .
10.0 out of 10, Exceptional, (117)
"We had a lovely stay in a very beautiful and clean cabin. Thank you!"
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, (316)
"Unbelievably quiet. Gorgeous location and cabin. Everything one needs is there. Smallest details thought of. Just lovely! We will be returning in the Winter. "
Get away from it all! Restored 1800 log cabin on 40 acres - NO cleaning fee!
The Bear Den (Secluded in Amish Country and peaceful)
9.8 out of 10, Exceptional, (24)
"Adequate"
The price is CA $181
CA $292 total
includes taxes & fees
Nov 17 - Nov 18
The Bear Den (Secluded in Amish Country and peaceful)
Your luxury cottage in the country - Murphin Ridge - Amish built
9.8 out of 10, Exceptional, (93)
"We found this place three weeks ago and stayed there for a four day extended weekend. We like it so much we came back for another four days. The place is beautiful very clean comfortable and extremely secluded. My only regret is that we didn’t wait a couple more weeks for the leaves to change more. Who knows, maybe will go back in another three weeks! "
The price is CA $181
CA $321 total
includes taxes & fees
Nov 14 - Nov 15
Your luxury cottage in the country - Murphin Ridge - Amish built
URBAN GETAWAY - .6 Downtown Maysville/Entire House
9.6 out of 10, Exceptional, (24)
"Very nice air B&B for the price. I needed a place that would allow pets and this property popped up first. We were happy with our stay and would rent again. Only downfall was it sits at a noisy intersection. "
The price is CA $110
CA $169 total
includes taxes & fees
Nov 3 - Nov 4
URBAN GETAWAY - .6 Downtown Maysville/Entire House
Hunter Lodge (Secluded in Amish Country and peaceful)
10.0 out of 10, Exceptional, (28)
"An oasis in an area devoid of decent motels or hotels. So glad we found this B&B."
The price is CA $182
CA $294 total
includes taxes & fees
Nov 16 - Nov 17
Hunter Lodge (Secluded in Amish Country and peaceful)
Quiet Country Home sleeps 22 people, perfect for Reunions, Teams, Retreats
10.0 out of 10, Exceptional, (56)
"Looking forward to booking again for next summer. Perfect property and plenty of space!"
Quiet Country Home sleeps 22 people, perfect for Reunions, Teams, Retreats
Rustic Lodge with private cabins / 6 person hot tub and camp fire
10.0 out of 10, Exceptional, (29)
"Perfect place to unwind after work. Will definitely book again. "
Rustic Lodge with private cabins / 6 person hot tub and camp fire
Secluded cabin located in Amish country
10.0 out of 10, Exceptional, (74)
"This property exceeded our expectations for sure. While it is a cabin, it has everything up to date and with quality amenities. We couldn't have been happier and got to spend some relaxing time around the fire pit. Frank is an awesome host."
Secluded cabin located in Amish country
Secluded in Amish Country and peaceful
9.6 out of 10, Exceptional, (15)
"Very good and an awesome place to stay!"
The price is CA $174
CA $285 total
includes taxes & fees
Nov 21 - Nov 22
Secluded in Amish Country and peaceful
Flash Lodge Add-on Cabin-Pamela's Diamond
9.4 out of 10, Exceptional, (23)
"Very nice very hard to find"
The price is CA $125
CA $209 total
includes taxes & fees
Nov 3 - Nov 4
Flash Lodge Add-on Cabin-Pamela's Diamond
Cozy newly remodeled camper with hot tub and fire pit close to hiking/kayaking
10.0 out of 10, Exceptional, (24)
"Great stay"
Cozy newly remodeled camper with hot tub and fire pit close to hiking/kayaking
Peaceful Country Retreat 20 acres Private Pond
9.8 out of 10, Exceptional, (17)
"This property is absolutely stunning! It was more than enough room for our family of 7, with room to spare. We all really enjoyed fishing in the pond, there are tons of fish, and a giant snapping turtle that my youngest unintentionally caught. There really is no need to leave the house, there is plenty to do on the property. We had a blast and made so many memories!"
Peaceful Country Retreat 20 acres Private Pond
The Manor at Maysville Golf Course View
9.6 out of 10, Exceptional, (15)
"This was our 2nd time staying at The Moss Manor and once again our stay was great. When we come back home to Ky if this property is available we will be staying again. Also very nice upgrades done in the house since our last stay. "
The price is CA $487
CA $974 total
includes taxes & fees
Nov 15 - Nov 16
The Manor at Maysville Golf Course View
Cowboy Saloon Cabin
9.6 out of 10, Exceptional, (10)
"I booked this cabin as a place to stay the night after travelling three hours to a catering event. It was perfect for my daughter and I. Close to town for gas, food. Cabin was well equipped with everything we could need. Wished we stayed longer to enjoy the deck on the back and front. It was peaceful. Highly recommend this place! Open communication with owners, easy check in. Very clean! "
The price is CA $188
CA $275 total
includes taxes & fees
Nov 22 - Nov 23
Cowboy Saloon Cabin
'Small Town Getaway'
9.8 out of 10, Exceptional, (8)
"House was very nice and clean. Only complaint i have is not enough towels and wash rags. Many people dont reuse the wash rag after showering. I find that gross. If you dont want to add more. Get a washer/dryee so we could wash "
'Small Town Getaway'
McKeever Mansion-9,000 sq ft. Perfect for corporate, families, or special events
10.0 out of 10, Exceptional, (20)
"The house was perfect for our needs. Immediate family and a few extended family members stayed for our daughter's wedding which took place only 15 minutes from the house. The location was ideal. The large kitchen made it great for family breakfast and lunch on the go. The kitchen was well stocked and had everything we needed. I will say I have stayed at a lot of places and these beds were very comfortable. The host took care of a couple of issues very quickly. The lock box was easy for...
McKeever Mansion-9,000 sq ft. Perfect for corporate, families, or special events
Amish-built cabin, serene and peaceful with pond and private dock for fishing.
10.0 out of 10, Exceptional, (13)
"Property and cabin was beautiful, very relaxing. "
Amish-built cabin, serene and peaceful with pond and private dock for fishing.
Peaceful 8 Bedroom 5 Bath w/patio bar-grill and swimming pond
10.0 out of 10, Exceptional, (19)
"This beautiful property was perfect for our family of 17 to meet together from points east and west. Sharon is a wonderful host, responding quickly to our questions and needs. The huge indoor kitchen was well-equipped to cook full meals for a big group. Two full-sized refrigerators were a big plus! We also enjoyed using the outdoor kitchen and fire pit. The game room, pond, boats, playhouse, and room to run were all hits with the children! So clean and well-maintained!"
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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Other types of properties in Winchester you may be interested in

Rustic Cabin with modern amenities and 1 acre stocked Fishing Lake !
10.0 out of 10, Exceptional, (254)
"Our stay at this cabin was great! It had everything we needed and more. The location was very peaceful. We saw deer in the backyard. The cabin was beautiful. I highly recommend staying here! The only thing it needs is curtains in the bedrooms. Otherwise everything was fantastic and we would stay here again! Thanks so much! "
Rustic Cabin with modern amenities and 1 acre stocked Fishing Lake !
Countryside Inn & Suites
2.5 star property
7.0 out of 10, Good, (459)
"My stay was great girl at desk was kinda rude "
The price is CA $120
CA $136 total
includes taxes & fees
Nov 14 - Nov 15
Countryside Inn & Suites
French Quarter Inn
3.0 star property
8.8 out of 10, Excellent, (661)
"It was right on the river and the views, both night and day, were lovely."
The price is CA $138
CA $153 total
includes taxes & fees
Nov 3 - Nov 4
French Quarter Inn
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.

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?

URBAN GETAWAY - .6 Downtown Maysville/Entire House: Visitors like this Winchester vacation home rental. It is located on a river and has a patio, a garden, and air-conditioning to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a microwave.

What’s there to see and do in Winchester?

While you're exploring the area, Adams Lake State Park and Rocky Fork Lake State Park are a couple of picturesque spots to get outside and enjoy nature. In the larger area, you’ll find Serpent Mound and Rocky Fork State Park.

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.