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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 1,144 total
includes taxes & fees
11 Apr - 12 Apr
4 Bed 3 bath clean , spacious all brick home , welcome families and work groups

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.
River Relaxation - Calm Riverfront Home in Winchester Kentucky

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
21 Apr - 22 Apr
The Winchester

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 422
AED 1,105 total
includes taxes & fees
12 Apr - 13 Apr
Red River Gorge Cozy Glamping Tent for 4 • Heated, Fire Pit & Hot Tub

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 419
AED 795 total
includes taxes & fees
6 May - 7 May
This house is a 2 bedroom(s), 1 bathrooms, located in Georgetown, KY.

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
16 Apr - 17 Apr
Canoe Believe It at The Ridge

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
12 Apr - 13 Apr
Cozy, Bright Home in Historic Downtown

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.
The price is AED 380
AED 831 total
includes taxes & fees
14 Apr - 15 Apr
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, (41 reviews)
"The hot tub was very nice and the property was so beautiful!!"
United States
April
The price is AED 430
AED 984 total
includes taxes & fees
19 Apr - 20 Apr
Hot Tub! Fire pit! Picnic area & Grill! View! Hardwicks Creek Haven@RRG

East Suite-🕊️ at Bleubird Studio, Walk to Downtown

East Suite-🕊️ at Bleubird Studio, Walk to Downtown
Georgetown
10.0 out of 10, Exceptional, (61 reviews)
"Great place to stay -- perfect location, wonderful host, beautiful accomodations, and sweet welcome dog on top of it all! Highly recommended. "
United States
l v.
The price is AED 459
AED 830 total
includes taxes & fees
28 Apr - 29 Apr
East Suite-🕊️ at Bleubird Studio, Walk to Downtown

Cozy 1-bedroom ranch house in Georgetown on 10 acres with horse paddock.

Cozy 1-bedroom ranch house in Georgetown on 10 acres with horse paddock.
Georgetown
10.0 out of 10, Exceptional, (3 reviews)
"Mitzi is a great host, and her place is clean and cozy. We would definitely stay here again. "
United States
Shelley M.
The price is AED 415
AED 745 total
includes taxes & fees
6 May - 7 May
Cozy 1-bedroom ranch house in Georgetown on 10 acres with horse paddock.

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.
Quiet Two Bedroom House

New Barndo/Kayak Launch/ 2 Private Hot Tubs

New Barndo/Kayak Launch/ 2 Private Hot Tubs
Stanton
10.0 out of 10, Exceptional, (13 reviews)
"Great property and amenities "
United States
john o.
The price is AED 1,095
AED 2,766 total
includes taxes & fees
13 Apr - 14 Apr
New Barndo/Kayak Launch/ 2 Private Hot Tubs

Bourbon Run - HotTub/ Ark 30min/ Horse Park 12min/ Walk Downtown/ 4BR Sleeps 8

Bourbon Run - HotTub/ Ark 30min/ Horse Park 12min/ Walk Downtown/ 4BR Sleeps 8
Georgetown
10.0 out of 10, Exceptional, (37 reviews)
"The host was very helpful and stayed in touch the whole stay and it was clean and everything worked like it should "
United States
Dustin W.
The price is AED 698
AED 1,438 total
includes taxes & fees
28 Apr - 29 Apr
Bourbon Run - HotTub/ Ark 30min/ Horse Park 12min/ Walk Downtown/ 4BR Sleeps 8

Bourbon Chaser- Horse Park 12min, Ark 30min, Hot Tub, 4 Bedrooms, Walk Downtown

Bourbon Chaser- Horse Park 12min, Ark 30min, Hot Tub, 4 Bedrooms, Walk Downtown
Georgetown
10.0 out of 10, Exceptional, (29 reviews)
"Great host and home. Enjoyed the hot tub with all the snow. Will definitely stay again"
United States
Rebecca F.
The price is AED 698
AED 1,438 total
includes taxes & fees
13 Apr - 14 Apr
Bourbon Chaser- Horse Park 12min, Ark 30min, Hot Tub, 4 Bedrooms, Walk Downtown

Retro Home Near Horse Park and Ark, Pet Friendly

Retro Home Near Horse Park and Ark, Pet Friendly
Georgetown
10.0 out of 10, Exceptional, (13 reviews)
"Great Location! Family friendly "
United States
Amanda C.
Retro Home Near Horse Park and Ark, Pet Friendly

New Barndo/Kayak Launch/ 2 Private Hot Tubs

New Barndo/Kayak Launch/ 2 Private Hot Tubs
Stanton
9.2 out of 10, Wonderful, (9 reviews)
"Amazing place! Super clean- all amenities taken care of! Would totally stay here again!"
United States
Laura P.
The price is AED 1,289
AED 3,013 total
includes taxes & fees
13 Apr - 14 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.
‘Clara’ Just Off I-75! 2 Full Bedrooms!

Tail End at The Ridge

Tail End at The Ridge
Powell County
10.0 out of 10, Exceptional, (2 reviews)
"We stayed a coupled nights and very much enjoyed it. Quiet area, far enough from the road. Hot tub was great to come back to after days on trails!"
United Kingdom
Eric P.
The price is AED 455
AED 936 total
includes taxes & fees
12 Apr - 13 Apr
Tail End at The Ridge

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 Midland- 2 King Beds! Great Location!
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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