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Check prices for these dates

Next weekend
21 Mar - 23 Mar
In two weeks
28 Mar - 30 Mar
In one month
11 Apr - 13 Apr
In two months
9 May - 11 May

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
Oven, stovetop, dishwasher

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!
Outdoor dining

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

9.8 out of 10, Exceptional, (134)
"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
Smart TV, fireplace, stereo, computer monitors

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
A Delightful A-Frame on 20-Acres with Hiking Trails, Hot Tub, Wifi, and More
Exterior

A Delightful A-Frame on 20-Acres with Hiking Trails, Hot Tub, Wifi, and More

A Delightful A-Frame on 20-Acres with Hiking Trails, Hot Tub, Wifi, and More
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
Peaceful Country Retreat 20 acres Private Pond
Exterior

Peaceful Country Retreat 20 acres Private Pond

9.8 out of 10, Exceptional, (20)
"Great place to stay! Very serene. It was tough to get a comfortable temperature in all areas of the home at the same time & the water pressure isn’t great, but otherwise we had a very nice stay there. "
Peaceful Country Retreat 20 acres Private Pond
Luxurious & Modern newly renovated good for corporate housing & family functions
Interior

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
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!
Tranquility Cottage | 3 Bed, 1.5 Bath
Fridge, microwave, oven, stovetop

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

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

10.0 out of 10, Exceptional, (32)
"Booked this place for a board game retreat and will be back! Great communication before and during with the hosts. Huge kitchen, very well-maintained hot tub, and massage chair! PRO: it's one large room!CON: it's one large room!If your group has both early risers AND late risers, I would recommend separating them so one group has the separate small cabins and the other group takes the beds above the lodge.5 actual beds, the rest are (very comfy) pull-out couches. No one in our group sharing the...
Rustic Lodge with private cabins / 6 person hot tub and camp fire
Quiet Country Home sleeps 22 people, perfect for Reunions, Teams, Retreats
Outdoor dining

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
~Lakeside Oasis~ Waterfront w/HotTub, Sauna & Dock
Outdoor dining

~Lakeside Oasis~ Waterfront w/HotTub, Sauna & Dock

10.0 out of 10, Exceptional, (2)
"A group of us stayed for a hiking weekend, and we absolutely loved the place. It was one I’ve the best rentals I’ve stayed at. "
~Lakeside Oasis~ Waterfront w/HotTub, Sauna & Dock
Unique stay, hot tub, secluded
Interior

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 AED 404
AED 936 total
includes taxes & fees
13 Mar - 14 Mar
Unique stay, hot tub, secluded
Experience Peace, Relaxation and Comfort in Kentucky with a touch of KENYA!
Fridge, microwave, oven, stovetop

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

The price is AED 683
AED 924 total
includes taxes & fees
1 Apr - 2 Apr
Experience Peace, Relaxation and Comfort in Kentucky with a touch of KENYA!
Hillsboro Hideaway w/ Private Hot Tub & Bunkhouse!
Microwave, stovetop, toaster, cookware/dishes/utensils

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!
Relax and Unwind at River Front Oasis w/ Hot Tub
Miscellaneous

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
Manchester Getaway on Ohio River Scenic Byway
Miscellaneous

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
~Lakeside Escape ~ Waterfront w/Hot Tub
Outdoor dining

~Lakeside Escape ~ Waterfront w/Hot Tub

~Lakeside Escape ~ Waterfront w/Hot Tub
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
Beautiful Rocky Fork 2BR Cozy Cottage
Terrace/patio

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
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 !
Exterior

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 !
New 3 Bedroom Log Cabin nestled in the woods with one acre fishing lake .
Fridge, microwave, oven, stovetop

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

10.0 out of 10, Exceptional, (127)
"The cabin is modern, cozy and clean and comes with everything you need!"
New 3 Bedroom Log Cabin nestled in the woods with one acre fishing lake .
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

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
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.