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Browse Select Winchester Vacation Homes

Spacious 4-bedroom 19th Century home in historic downtown Maysville!

10.0 out of 10, Exceptional, (1)
"Gorgeous home located steps away from Maysville night life. Ample parking and the neighborhood felt safe. The kitchen was huge and had everything you would need. I only wish I could have actually had time to use it. Plenty of bathrooms, all updated and nicely decorated. The host sent all the instructions for checking in and out before I arrived, which made the process a breeze. I will definitely be staying here again."
Spacious 4-bedroom 19th Century home in historic downtown Maysville!

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

10.0 out of 10, Exceptional, (27)
"The place was huge, clean, and amazing! Would recommend to anyone! "
Peaceful 8 Bedroom 5 Bath w/patio bar-grill and swimming pond

The Manor at Maysville Golf Course View

9.8 out of 10, Exceptional, (22)
"Our families got together for a lovely Christmas gathering here. The house was beautifully decorated!"
The Manor at Maysville Golf Course View

10 min to Rocky Fork Lake ⏐ Gorgeous Peaceful Farm for Large Groups - two houses

10.0 out of 10, Exceptional, (2)
"We had the absolute best experience during our stay. The hosts’ incredible hospitality and servant hearted care for our group was stunning. We immediately booked another stay before we even checked out. It’s beautiful. It’s peaceful. It’s serene. Is an oasis to take a deep breath. We are so thankful to have found it. "
10 min to Rocky Fork Lake ⏐ Gorgeous Peaceful Farm for Large Groups - two houses

Sleeps 8. Quiet village street. Historic Ripley OH

10.0 out of 10, Exceptional, (1)
"It was excellent and very clean . We could have stayed a couple of more days due to finding different things to do . "
Sleeps 8. Quiet village street. Historic Ripley OH

White Oak Cottage Sleeps 4

8.0 out of 10, Very good, (1)
"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

LAKE HOUSE ON ROCKY FORK!

9.4 out of 10, Exceptional, (30)
"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!

Unique stay, hot tub, secluded

9.4 out of 10, Exceptional, (10)
"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 $352 total
includes taxes & fees
Aug 14 - Aug 15
Unique stay, hot tub, secluded

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

9.4 out of 10, Exceptional, (3)
"This was a great stay. Very easy to find and in a good area. Very clean and nice. "
The price is CA $279
CA $378 total
includes taxes & fees
Aug 10 - Aug 11
Experience Peace, Relaxation and Comfort in Kentucky with a touch of KENYA!

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

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

10.0 out of 10, Exceptional, (3)
"This was a really nice home. Very nicely decorated and very clean. The town was super cute and the people were friendly. Really enjoyed our stay and would stay here again. Highly recommend! "
AFORDABLE & CHARMING HOME - Enjoy Urban Life & Nature! Hike, Bike, Shop & Dine!

Peaceful Country Retreat 20 acres Private Pond

9.8 out of 10, Exceptional, (22)
"We enjoyed the stay here. I would recommend this place for its quiet atmosphere and great host"
Peaceful Country Retreat 20 acres Private Pond

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

9.8 out of 10, Exceptional, (6)
"The property was beautiful and peaceful. We loved relaxing in the hot tub and watching all the birds. We'd love to come back when it's not so rainy and do some more exploring! "
A Delightful A-Frame on 20-Acres with Hiking Trails, Hot Tub, Wifi, and More

Country Cornerstone Retreat, Pool | Game Room | Theater | Hot Tub | Massage

The price is CA $636
CA $1,166 total
includes taxes & fees
Aug 13 - Aug 14
Country Cornerstone Retreat, Pool | Game Room | Theater | Hot Tub | Massage

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

9.8 out of 10, Exceptional, (38)
"Host is helpful and check in/out was a breeze!"
McKeever Mansion-9,000 sq ft. Perfect for corporate, families, or special events

SECLUDED PARADISE!!! Tranquility on 8 Acres Bordering Brush Creek Forest!!

9.8 out of 10, Exceptional, (139)
"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."
SECLUDED PARADISE!!! Tranquility on 8 Acres Bordering Brush Creek Forest!!

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

2.0 star property
8.4 out of 10, Very good, (5)
"nice property, easy check in/out and responsive host. "
Lake front 3-bedroom house @ Rocky Fork Lake with Private Dock

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

10.0 out of 10, Exceptional, (63)
"Good space for family gatherings!"
Quiet Country Home sleeps 22 people, perfect for Reunions, Teams, Retreats

Lakeside Escape ~ Waterfront w/Hot Tub (NEW DOCK!)

10.0 out of 10, Exceptional, (3)
"Great property on the water. The place had everything we needed. "
Lakeside Escape ~ Waterfront w/Hot Tub (NEW DOCK!)

Beautiful Rocky Fork 2BR Cozy Cottage

10.0 out of 10, Exceptional, (111)
"Great stay for my sisters graduation weekend!"
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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