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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 1,132 total
includes taxes & fees
26 Apr - 27 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 496
AED 1,073 total
includes taxes & fees
7 May - 8 May
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 558
AED 1,514 total
includes taxes & fees
26 Apr - 27 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 453
AED 724 total
includes taxes & fees
26 Apr - 27 Apr
Peregrine Cabin - Off the Grid, hike-in cabin

Canoe Believe It at The Ridge

Canoe Believe It at The Ridge
Powell County
10.0 out of 10, Exceptional, (2 reviews)
"Great place! Would stay again!"
United States
Rachel B.
The price is AED 459
AED 859 total
includes taxes & fees
4 May - 5 May
Canoe Believe It at The Ridge

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, (7 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 1,105 total
includes taxes & fees
27 Apr - 28 Apr
Red River Gorge Cozy Glamping Tent for 4 • Heated, Fire Pit & Hot Tub

Boulder View - Hot Tub/Fire Pit

Boulder View - Hot Tub/Fire Pit
Stanton
The price is AED 428
AED 1,096 total
includes taxes & fees
26 Apr - 27 Apr
Boulder View - Hot Tub/Fire Pit

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 901
AED 2,503 total
includes taxes & fees
27 Apr - 28 Apr
New Barndo/Kayak Launch/ 2 Private Hot Tubs

Cozy, Bright Home in Historic Downtown

Cozy, Bright Home in Historic Downtown
Mount Sterling
8.4 out of 10, Very Good, (22 reviews)
"We did not stay. Nothing had been cleaned. Asked for a refund"
United States
Ginger
The price is AED 231
AED 458 total
includes taxes & fees
27 Apr - 28 Apr
Cozy, Bright Home in Historic Downtown

Theodore Tiny Cabin- RRG Hot Tub! Pet Friendly!

Theodore Tiny Cabin- RRG Hot Tub! Pet Friendly!
Powell County
9.4 out of 10, Exceptional, (39 reviews)
"What a fun experience this tiny house was! It was exactly like the pictures and exceeded our expectations. We highly recommend if you’re looking for something different. "
United States
Danielle
The price is AED 470
AED 853 total
includes taxes & fees
11 May - 12 May
Theodore Tiny Cabin- RRG Hot Tub! Pet Friendly!

Modern 3bed 2bath, short drive to RRG, walk to stores and restaurants! So clean!

Modern 3bed 2bath, short drive to RRG, walk to stores and restaurants! So clean!
Stanton
10.0 out of 10, Exceptional, (44 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 407
AED 869 total
includes taxes & fees
7 May - 8 May
Modern 3bed 2bath, short drive to RRG, walk to stores and restaurants! So clean!

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
10 May - 11 May
This house is a 2 bedroom(s), 1 bathrooms, located in Georgetown, KY.

Kim's Retreat: 3-BR Cabin w/ Hot Tub near Natural Bridge & Red River Gorge

Kim's Retreat: 3-BR Cabin w/ Hot Tub near Natural Bridge & Red River Gorge
Stanton
9.0 out of 10, Wonderful, (18 reviews)
"Great service and clean cozy cabin "
United States
Melissa G.
The price is AED 595
AED 1,173 total
includes taxes & fees
25 Apr - 26 Apr
Kim's Retreat: 3-BR Cabin w/ Hot Tub near Natural Bridge & Red River Gorge

Quiet Two Bedroom House

Quiet Two Bedroom House
Lexington
9.6 out of 10, Exceptional, (13 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
30 Apr - 1 May
Quiet Two Bedroom House

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 463
AED 1,085 total
includes taxes & fees
27 Apr - 28 Apr
Pet-Friendly Bluegrass Retreat w/ Fenced Yard

Hot Tub Glow Hill Home Near KY Horse Park, Ark and Rupp Arena

Hot Tub Glow Hill Home Near KY Horse Park, Ark and Rupp Arena
Georgetown
10.0 out of 10, Exceptional, (4 reviews)
"Enjoyed my stay. Hosts were easy to communicate with and the rental was clean and quiet. "
United States
Barton
The price is AED 397
AED 822 total
includes taxes & fees
27 Apr - 28 Apr
Hot Tub Glow Hill Home Near KY Horse Park, Ark and Rupp Arena

Game Room | King Suite | Firepit | Patio | Grill

Game Room | King Suite | Firepit | Patio | Grill
Georgetown
9.6 out of 10, Exceptional, (12 reviews)
"Very nice and clean home. And was equipped with what we needed. Would stay again if in that area."
United States
Pamela L.
The price is AED 395
AED 1,168 total
includes taxes & fees
27 Apr - 28 Apr
Game Room | King Suite | Firepit | Patio | Grill

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 1,437 total
includes taxes & fees
27 Apr - 28 Apr
Bourbon Run - HotTub/ Ark 30min/ Horse Park 12min/ Walk Downtown/ 4BR Sleeps 8

‘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 231
AED 614 total
includes taxes & fees
27 Apr - 28 Apr
‘Clara’ Just Off I-75! 2 Full Bedrooms!

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, (44 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
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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