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Compare 35 Vacation Homes in Winchester with updated reviews, rates, and availability.

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

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

9.8 out of 10, Exceptional, (26)
"We had a large family reunion and we were all very comfortable from little kids to adults. Everything we could’ve possibly wanted …it was there. We had a very minor situation and it was corrected within 20 minutes. We would definitely return. Wonderful memories were made! Thank you for being a part of that!"
McKeever Mansion-9,000 sq ft. Perfect for corporate, families, or special events
THIS IS IT!! Large Private Home, 8 Acres Borders Forest; Includes All Amenities!
2800 sq. ft. 3-level Home, bordering Thousands of acres of Brush Creek Forest

THIS IS IT!! Large Private Home, 8 Acres Borders Forest; Includes All Amenities!

9.8 out of 10, Exceptional, (133)
"This is our second Thanksgiving stay with extended family. We love it!"
THIS IS IT!! Large Private Home, 8 Acres Borders Forest; Includes All Amenities!
The Manor at Maysville Golf Course View
Exterior

The Manor at Maysville Golf Course View

9.8 out of 10, Exceptional, (17)
"My family and friends had a fantastic stay at the Manor! The space offers plenty of room, making it perfect for relaxing or getting work done. The Wi-Fi was excellent, which was a huge plus. The host was incredibly responsive, ensuring a smooth and hassle-free experience. Plus, the location is awesome—close to everything you need. Highly recommend!"
The Manor at Maysville Golf Course View
LAKE HOUSE ON ROCKY FORK!
Aerial view

LAKE HOUSE ON ROCKY FORK!

9.4 out of 10, Exceptional, (23)
"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!
Hillsboro Hideaway w/ Private Hot Tub & Bunkhouse!
Hillsboro Vacation Rental | 1,400 Sq Ft | 4BR | 3BA | Stairs Required

Hillsboro Hideaway w/ Private Hot Tub & Bunkhouse!

8.8 out of 10, Excellent, (5)
"The house was very clean and cozy inside with many great features. Outside there were bees swarming around the front corner of the hot tub. The gas tank on the grill was empty and there were many bugs accumulated on the outside of the house near the doors that needed cleaned. . "
Hillsboro Hideaway w/ Private Hot Tub & Bunkhouse!
Tranquility Cottage | 3 Bed, 1.5 Bath
Exterior

Tranquility Cottage | 3 Bed, 1.5 Bath

9.0 out of 10, Wonderful, (11)
"I have stayed here before 2 years ago. Great location if hunting in Peebles. Other than the heating system being a bit clunky (noisy at night) when running. It’s a really well kept place. "
Tranquility Cottage | 3 Bed, 1.5 Bath
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, (22)
"The place was huge, clean, and amazing! Would recommend to anyone! "
Peaceful 8 Bedroom 5 Bath w/patio bar-grill and swimming pond
Quiet Country Home sleeps 22 people, perfect for Reunions, Teams, Retreats
Exterior

Quiet Country Home sleeps 22 people, perfect for Reunions, Teams, Retreats

10.0 out of 10, Exceptional, (60)
"Our family of 20 including 12 kids ages 1-12 was fun. The outside of the house looks small, but we had plenty of room inside. The only downside for a cold weather visit with kids is there is only one bathroom in the house. Other restrooms are in the adjacent shower house. So the short walk to the bathroom was a bit chilly. "
Quiet Country Home sleeps 22 people, perfect for Reunions, Teams, Retreats
Rustic Lodge with private cabins / 6 person hot tub and camp fire
Rustic Lodge with fireplace, WIFI, smarttv with Hulu, and massage chair.

Rustic Lodge with private cabins / 6 person hot tub and camp fire

10.0 out of 10, Exceptional, (31)
"Will definitely book again"
Rustic Lodge with private cabins / 6 person hot tub and camp fire
Luxurious & Modern newly renovated good for corporate housing & family functions
Exterior

Luxurious & Modern newly renovated good for corporate housing & family functions

9.6 out of 10, Exceptional, (4)
"it was great"
Luxurious & Modern newly renovated good for corporate housing & family functions
Unique stay, hot tub, secluded
Living area

Unique stay, hot tub, secluded

8.6 out of 10, Excellent, (4)
"Quiet, secluded, clean, plenty of room for a couple and ample kitchen space and equipment to cook meals... We did our annual couples retreat at Harvest Haven and really got the headspace for goalsetting and reviewing the past year. The rose petals on the bed were a nice touch. The skies were clear and we were able to see so many stars at night. The hottub was perfect. We visited Amish shops, a local diner, and Serpent Mound, but spent most of our time at the silo. It was wonderful to get away...
The price is SAR 413
SAR 948 total
includes taxes & fees
3 Mar - 4 Mar
Unique stay, hot tub, secluded
Experience Peace, Relaxation and Comfort in Kentucky with a touch of KENYA!
Exterior

Experience Peace, Relaxation and Comfort in Kentucky with a touch of KENYA!

The price is SAR 477
SAR 695 total
includes taxes & fees
25 Feb - 26 Feb
Experience Peace, Relaxation and Comfort in Kentucky with a touch of KENYA!
Beautiful Rocky Fork 2BR Cozy Cottage
Welcome to Blue Heaven Cottage

Beautiful Rocky Fork 2BR Cozy Cottage

10.0 out of 10, Exceptional, (106)
"We enjoyed our stay at Robin's cottage. Everything was clean and comfortable. Great communication. The kitchen had everything we needed. We really appreciated the fire pit and firewood. Self check-in was easy. Thank you for hosting us. "
Beautiful Rocky Fork 2BR Cozy Cottage
Relax and Unwind at River Front Oasis w/ Hot Tub
Interior

Relax and Unwind at River Front Oasis w/ Hot Tub

10.0 out of 10, Exceptional, (3)
"Awesome...."
Relax and Unwind at River Front Oasis w/ Hot Tub
URBAN GETAWAY - .6 Downtown Maysville/Entire House
Urban Getaway front porch - 535 Forest Av.

URBAN GETAWAY - .6 Downtown Maysville/Entire House

9.2 out of 10, Wonderful, (27)
"Love this house, we have stayed here 3 times. Clean, cozy "
URBAN GETAWAY - .6 Downtown Maysville/Entire House
Lake front 3-bedroom house @ Rocky Fork Lake with Private Dock
Miscellaneous

Lake front 3-bedroom house @ Rocky Fork Lake with Private Dock

2.0 star property
10.0 out of 10, Exceptional, (2)
"Nice place to stay. "
Lake front 3-bedroom house @ Rocky Fork Lake with Private Dock
Beautifully renovated unit in the downtown Maysville’s entertainment district
Room

Beautifully renovated unit in the downtown Maysville’s entertainment district

10.0 out of 10, Exceptional, (38)
"We came to Maysville from Indiana to celebrate a friend’s birthday whose family is from the area. I found the apartment on Vrbo and it was everything we expected and then some!! Beautiful apartment, quaint neighborhood, wonderful restaurants within walking distance, and the hosts were very welcoming and responsive. I will say the stairs are every bit as steep as everyone describes, but we managed without any issues. I do caution anyone with limited abilities to consider the stairs before...
Beautifully renovated unit in the downtown Maysville’s entertainment district
Manchester Getaway on Ohio River Scenic Byway
Manchester Vacation Rental | 3BR | 1.5BA | 1,500 Sq Ft | Stairs Required

Manchester Getaway on Ohio River Scenic Byway

8.0 out of 10, Very Good, (1)
"Definitely not the best to swim but great to fish cook and hangout with the family for some peaceful time"
Manchester Getaway on Ohio River Scenic Byway
Beautifully renovated 3BR house w/lake views
Front of house with fun directional sign

Beautifully renovated 3BR house w/lake views

10.0 out of 10, Exceptional, (24)
"Changes in Latitude was such a great find! The house has lots of room for friends and family to gather. It was clean and had everything you need for your stay. Robin was easy to communicate with and made the check in/check out process easy. "
Beautifully renovated 3BR house w/lake views
AFORDABLE & CHARMING HOME - Enjoy Urban Life & Nature! Hike, Bike, Shop & Dine!
Exterior

AFORDABLE & CHARMING HOME - Enjoy Urban Life & Nature! Hike, Bike, Shop & Dine!

10.0 out of 10, Exceptional, (1)
"Very happy with our stay! Right outside of a little downtown area and the police department is across the street. It was very quiet, which we enjoy. There are two bedrooms upstairs - queen bed and twin bed. Additionally the living room has a queen sleeper inside of the couch. Plenty of dishes, towels, and anything else you would need. Didn’t see a single bug, always a win in the middle of summer when we stay somewhere. Only two recommendations on the property are if you use the boiler setting on...
AFORDABLE & CHARMING HOME - Enjoy Urban Life & Nature! Hike, Bike, Shop & Dine!
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 property types in Winchester

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

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

10.0 out of 10, Exceptional, (257)
"The cabin was wonderful and the host was great! We got about 14 inches of snow while there and the views were absolutely gorgeous. Had a few hiccups but the host was right there when we needed him. He was extremely friendly and helpful. Will definitely stay again!"
Rustic Cabin with modern amenities and 1 acre stocked Fishing Lake !
McKeever Mansion-9,000 sq ft. Perfect for corporate, families, or special events
Exterior

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

9.8 out of 10, Exceptional, (26)
"We had a large family reunion and we were all very comfortable from little kids to adults. Everything we could’ve possibly wanted …it was there. We had a very minor situation and it was corrected within 20 minutes. We would definitely return. Wonderful memories were made! Thank you for being a part of that!"
McKeever Mansion-9,000 sq ft. Perfect for corporate, families, or special events
New 3 Bedroom Log Cabin nestled in the woods with one acre fishing lake .
Real authentic log cabin

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

10.0 out of 10, Exceptional, (126)
"This cabin was beautiful and clean and had all the accommodations needed! We will definitely be back! "
New 3 Bedroom Log Cabin nestled in the woods with one acre fishing lake .
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.