Book Holiday Homes in Winchester

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Featured Holiday Homes in Winchester

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

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

Williamsburg
Located in Williamsburg, this vacation home is a 3-minute drive from Williamsburg Branch Public Library and 7 minutes from East Fork State Park.
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!

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

Peebles
When you stay at this vacation home in Peebles, you'll be in the mountains and steps from Brush Creek State Forest.
THIS IS IT!! Large Private Home, 8 Acres Borders Forest; Includes All Amenities!
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

Peebles
With a stay at this vacation home in Peebles, you'll be within a 15-minute drive of Serpent Mound and Brush Creek State Forest.
A Delightful A-Frame on 20-Acres with Hiking Trails, Hot Tub, Wifi, and More
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Peaceful 8 Bedroom 5 Bath w/patio bar-grill and swimming pond

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

Peebles
When you stay at this vacation home in Peebles, you'll be 7 minutes by foot from Brush Creek State Forest.
Peaceful 8 Bedroom 5 Bath w/patio bar-grill and swimming pond
LAKE HOUSE ON ROCKY FORK!

LAKE HOUSE ON ROCKY FORK!

Hillsboro
When you stay at this vacation home in Hillsboro, you'll be on a lake, within a 5-minute drive of Rocky Fork Lake and Rocky Fork State Park.
LAKE HOUSE ON ROCKY FORK!
Peaceful Country Retreat 20 acres Private Pond

Peaceful Country Retreat 20 acres Private Pond

Sardinia
With a stay at this vacation home in Sardinia, you'll be 31.7 mi (51.1 km) from EastGate Mall and 15.4 mi (24.8 km) from Meranda-Nixon Winery.
Peaceful Country Retreat 20 acres Private Pond
'Small Town Getaway'

'Small Town Getaway'

Sardinia
With a stay at this vacation home in Sardinia, you'll be 27.3 mi (43.9 km) from EastGate Mall and 14.1 mi (22.8 km) from Grant Boyhood Home.
'Small Town Getaway'
Tranquility Cottage | 3 Bed, 1.5 Bath

Tranquility Cottage | 3 Bed, 1.5 Bath

West Union
A stay at this vacation home places you in the heart of West Union, and within a 15-minute drive of Adams Lake State Park.
Tranquility Cottage | 3 Bed, 1.5 Bath
 Quiet Country Home sleeps 22 people, perfect for Reunions, Teams, Retreats

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

Hamersville
Located in Hamersville, this vacation home is on a lake, within a 10-minute drive of Burke Park and Acord Park.
Quiet Country Home sleeps 22 people, perfect for Reunions, Teams, Retreats
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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.

Winchester Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Winchester vacation homes are the perfect way for you to wing it.

Holiday houses in Winchester let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Winchester in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Winchester adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Winchester with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Winchester vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Winchester Holiday Homes essential information

Accommodation
46 Holiday Homes
Lowest Price
AU$89
Highest Price
AU$196
Popular accommodation
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!, 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, LAKE HOUSE ON ROCKY FORK!, Peaceful Country Retreat 20 acres Private Pond, 'Small Town Getaway', Tranquility Cottage | 3 Bed, 1.5 Bath, Quiet Country Home sleeps 22 people, perfect for Reunions, Teams, Retreats

Top trending hotels in Winchester

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

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

Winchester
When you stay at this cabin in Winchester, you'll be on a lake and 11 minutes by car from Adams Lake State Park.
Rustic Cabin with modern amenities and 1 acre stocked Fishing Lake !
Countryside Inn & Suites

Countryside Inn & Suites

2.5 out of 5
100 Leininger Street, Mount Orab, OH
Fully refundableReserve now, pay when you stay
The price is AU$156 per night from 17 Apr to 18 Apr
AU$156
includes taxes & fees
17 Apr - 18 Apr
With a stay at Countryside Inn & Suites in Mount Orab, you'll be 20.2 mi (32.5 km) from EastGate Mall and 31.3 mi (50.4 km) from Riverbend Music Center.
Countryside Inn & Suites
French Quarter Inn

French Quarter Inn

3 out of 5
25 East McDonald Parkway, Maysville, KY
Fully refundableReserve now, pay when you stay
The price is AU$196 per night from 14 Apr to 15 Apr
AU$196
includes taxes & fees
14 Apr - 15 Apr
With a stay at French Quarter Inn in Maysville, you'll be within a 5-minute walk of Russell Theatre and Kentucky Gateway Museum Center.
French Quarter Inn
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Beverly hills inn

Beverly hills inn

2.5 out of 5
1830 U.S. 52, Aberdeen, OH
Fully refundableReserve now, pay when you stay
The price is AU$89 per night from 4 Apr to 5 Apr
AU$89
includes taxes & fees
4 Apr - 5 Apr
Located in Aberdeen, Beverly hills inn is within a 5-minute drive of Ohio River and National Underground Railroad Museum.
Beverly hills inn
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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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^Subject to availability and chosen travel dates.