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Our top choices for Winchester vacation homes

4 Bed 3 bath clean , spacious all brick home , welcome families and work groups

4 Bed 3 bath clean , spacious all brick home , welcome families and work groups
Winchester
9.8 out of 10, Exceptional, (7 reviews)
"Very homey place to stay! Nice neighborhood!"
United States
Tim T.
The price is AED 545
AED 1,107 total
includes taxes & fees
19 Apr - 20 Apr
4 Bed 3 bath clean , spacious all brick home , welcome families and work groups

The Winchester

The Winchester
Winchester
8.4 out of 10, Very Good, (7 reviews)
"I rented this house for my bridesmaids. It was a great location and house. The owner was accommodating and replied quickly "
United States
Karissa A.
The price is AED 545
AED 1,136 total
includes taxes & fees
20 Apr - 21 Apr
The Winchester

River Relaxation - Calm Riverfront Home in Winchester Kentucky

River Relaxation - Calm Riverfront Home in Winchester Kentucky
Winchester
7.0 out of 10, Good, (4 reviews)
"We loved the house, the hosts were great and super communicative! The house is also close to Lexington and Winchester so we had plenty to do and places to eat out! "
United States
Maeve R.
The price is AED 536
AED 1,478 total
includes taxes & fees
20 Apr - 21 Apr
River Relaxation - Calm Riverfront Home in Winchester Kentucky

Peregrine Cabin - Off the Grid, hike-in cabin

Peregrine Cabin - Off the Grid, hike-in cabin
Stanton
10.0 out of 10, Exceptional, (13 reviews)
"Complete privacy, Awesome nature trails, Friendly Owners"
United States
Richard M.
The price is AED 380
AED 642 total
includes taxes & fees
20 Apr - 21 Apr
Peregrine Cabin - Off the Grid, hike-in cabin

Red River Gorge Cozy Glamping Tent for 4 • Heated, Fire Pit & Hot Tub

Red River Gorge Cozy Glamping Tent for 4 • Heated, Fire Pit & Hot Tub
Stanton
10.0 out of 10, Exceptional, (6 reviews)
"Yes, I brought my tiny dog and she loved it there as much as we did! "
United States
Kimberly J.
The price is AED 441
AED 1,121 total
includes taxes & fees
23 Apr - 24 Apr
Red River Gorge Cozy Glamping Tent for 4 • Heated, Fire Pit & Hot Tub

Cozy, Bright Home in Historic Downtown

Cozy, Bright Home in Historic Downtown
Mount Sterling
8.8 out of 10, Excellent, (21 reviews)
"Great stay as usual. Owners are super friendly & helpful. This was our 3rd time staying as we've made this our regular when visiting family in the area."
United States
Brittany K.
The price is AED 231
AED 458 total
includes taxes & fees
19 Apr - 20 Apr
Cozy, Bright Home in Historic Downtown

Canoe Believe It at The Ridge

Canoe Believe It at The Ridge
Powell County
10.0 out of 10, Exceptional, (1 review)
"Great place! Would stay again!"
United States
Rachel B.
The price is AED 455
AED 834 total
includes taxes & fees
22 Apr - 23 Apr
Canoe Believe It at The Ridge

New Barndo/Kayak Launch/ 2 Private Hot Tubs

New Barndo/Kayak Launch/ 2 Private Hot Tubs
Stanton
10.0 out of 10, Exceptional, (14 reviews)
"Great property and amenities "
United States
john o.
The price is AED 1,000
AED 2,649 total
includes taxes & fees
20 Apr - 21 Apr
New Barndo/Kayak Launch/ 2 Private Hot Tubs

‘Clara’ Just Off I-75! 2 Full Bedrooms!

‘Clara’ Just Off I-75! 2 Full Bedrooms!
Lexington
8.0 out of 10, Very Good, (22 reviews)
"Stayed with a friend for a convention. The house was clean and comfortable"
United States
Jennifer W.
The price is AED 209
AED 588 total
includes taxes & fees
19 Apr - 20 Apr
‘Clara’ Just Off I-75! 2 Full Bedrooms!

The Midland- 2 King Beds! Great Location!

The Midland- 2 King Beds! Great Location!
Lexington
9.2 out of 10, Wonderful, (26 reviews)
"Everything was very clean, comfortable and nicely decorated. Great location!"
United States
Megin K.
The price is AED 701
AED 1,577 total
includes taxes & fees
18 May - 19 May
The Midland- 2 King Beds! Great Location!

Quiet Two Bedroom House

Quiet Two Bedroom House
Lexington
9.6 out of 10, Exceptional, (12 reviews)
"Great property, very clean, scenic views and great value! Will stay again!"
United States
Rob S.
The price is AED 808
AED 1,045 total
includes taxes & fees
29 Apr - 30 Apr
Quiet Two Bedroom House

This house is a 2 bedroom(s), 1 bathrooms, located in Georgetown, KY.

This house is a 2 bedroom(s), 1 bathrooms, located in Georgetown, KY.
Georgetown
8.6 out of 10, Excellent, (33 reviews)
"We had a beautiful stay. This house has a wonderful home feel! It was clean and had everything we needed. We will be back! "
United States
Corrie S.
The price is AED 294
AED 650 total
includes taxes & fees
19 Apr - 20 Apr
This house is a 2 bedroom(s), 1 bathrooms, located in Georgetown, KY.

Boulder View - Hot Tub/Fire Pit

Boulder View - Hot Tub/Fire Pit
Stanton
The price is AED 428
AED 1,072 total
includes taxes & fees
30 Apr - 1 May
Boulder View - Hot Tub/Fire Pit

Cozy Modern 3-bd, Pet Friendly, 12 miles from RRG!

Cozy Modern 3-bd, Pet Friendly, 12 miles from RRG!
Stanton
10.0 out of 10, Exceptional, (43 reviews)
"It was a nice comfortable cottage with all the amenities we needed to make our stay like home."
United States
Martha I.
Cozy Modern 3-bd, Pet Friendly, 12 miles from RRG!

Hot Tub! Fire pit! Picnic area & Grill! View! Hardwicks Creek Haven@RRG

Hot Tub! Fire pit! Picnic area & Grill! View! Hardwicks Creek Haven@RRG
Clay City
10.0 out of 10, Exceptional, (43 reviews)
"The hot tub was very nice and the property was so beautiful!!"
United States
April
Hot Tub! Fire pit! Picnic area & Grill! View! Hardwicks Creek Haven@RRG

New Barndo/ATV Trailer Park/Outdoor Shower/HotTub

New Barndo/ATV Trailer Park/Outdoor Shower/HotTub
Stanton
10.0 out of 10, Exceptional, (11 reviews)
"We loved our stay at the Barndo!! It was far enough away from the main roads to feel remote, but close enough to not be far away."
United States
steve
New Barndo/ATV Trailer Park/Outdoor Shower/HotTub

Beautiful 4-bedroom home, close to Downtown/UK

Beautiful 4-bedroom home, close to Downtown/UK
Lexington
10.0 out of 10, Exceptional, (4 reviews)
"We had a great stay at this property. The house was clean and 100% ready to go. Great location. "
United States
Jonathan H.
The price is AED 452
AED 1,095 total
includes taxes & fees
11 May - 12 May
Beautiful 4-bedroom home, close to Downtown/UK

Relaxing Hot Tub | S’mores Fire Pit | Garage

Relaxing Hot Tub | S’mores Fire Pit | Garage
LEXINGTON
9.2 out of 10, Wonderful, (48 reviews)
"Communication with the host was very timely, and all accommodations were clean and working. We had a great stay!"
United States
Francesca A.
The price is AED 482
AED 1,166 total
includes taxes & fees
10 May - 11 May
Relaxing Hot Tub | S’mores Fire Pit | Garage

Pet-Friendly Bluegrass Retreat w/ Fenced Yard

Pet-Friendly Bluegrass Retreat w/ Fenced Yard
Georgetown
9.2 out of 10, Wonderful, (31 reviews)
"Stayed one night while traveling with our dog. Great set up, very comfortable. Fenced yard was spacious and lovely. Neighborhood felt safe and secure. Visited the cows in the nearby field. Would definitely stay again!"
United States
Elaine H.
The price is AED 551
AED 1,211 total
includes taxes & fees
29 Apr - 30 Apr
Pet-Friendly Bluegrass Retreat w/ Fenced Yard

Westwood Luxury Ranch Home includes washer/dryer

Westwood Luxury Ranch Home includes washer/dryer
Richmond
10.0 out of 10, Exceptional, (44 reviews)
"Great place, very comfortable. "
United States
Rebecca V.
The price is AED 562
AED 1,219 total
includes taxes & fees
20 Apr - 21 Apr
Westwood Luxury Ranch Home includes washer/dryer
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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Top Winchester Hotel Reviews

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