Photo by Hyelsinta

Search Cottages in Winchester

  • Plan, book, stay with confidence

    • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Next weekend
25 Rab. II - 27 Rab. II
In two weeks
2 Jum. I - 4 Jum. I
In one month
16 Jum. I - 18 Jum. I
In two months
13 Jum. II - 15 Jum. II

Compare 34 Cottages in Winchester with updated reviews, rates, and availability.

Charming Cottage Home On A Farm In The Kentucky Horse Country! Relax!
Property grounds

Charming Cottage Home On A Farm In The Kentucky Horse Country! Relax!

10.0 out of 10, Exceptional, (263)
"Great, quiet, clean"
The price is SAR 657
SAR 1,158 total
includes taxes & fees
27 Apr - 28 Apr
Charming Cottage Home On A Farm In The Kentucky Horse Country! Relax!
Cozy 1 bedroom cottage on picturesque horse farm
Fridge, microwave, coffee/tea maker, toaster

Cozy 1 bedroom cottage on picturesque horse farm

10.0 out of 10, Exceptional, (27)
"Loved the cottage, super clean and fresh, very nicely updated, very classy. My only disappointment was that it was portayed (in my opinion) as if it was the only cottage there. There is one in close proximity behind the unit and it appears that there is one above the unit that we stayed in. I would not have booked if I had realized this. All that having been said, I'm glad that we stayed there. It was a very nice place to spend a few days - you won't find a cleaner VRBO or nicer setting."
Cozy 1 bedroom cottage on picturesque horse farm
1 bed cottage, grill, fire pit, Very close to Red River Gorge!!
Exterior detail

1 bed cottage, grill, fire pit, Very close to Red River Gorge!!

8.8 out of 10, Excellent, (15)
"We enjoyed our stay. The cottage had everything we needed and a great price. "
1 bed cottage, grill, fire pit, Very close to Red River Gorge!!
Mountaintop Cottage
Terrace/patio

Mountaintop Cottage

2.0 star property
10.0 out of 10, Exceptional, (8)
"We appreciated the communication and comfort of the home. Definitely one of our top favorites we have rented on vrbo! The house is in a very remote location however the drive is worth it! "
The price is SAR 507
SAR 724 total
includes taxes & fees
10 May - 11 May
Mountaintop Cottage
Springside BoHo Getaway
3 bedrooms, iron/ironing board, free WiFi, bed sheets

Springside BoHo Getaway

10.0 out of 10, Exceptional, (40)
"We enjoyed the property, we were comfortable and felt safe there. Fun boho environment with good food across from the street. Host was available, kind and great communication."
The price is SAR 563
SAR 1,059 total
includes taxes & fees
21 Apr - 22 Apr
Springside BoHo Getaway
Bungalow | 1 Bed, 0.5 Bath
Interior

Bungalow | 1 Bed, 0.5 Bath

10.0 out of 10, Exceptional, (3)
"If you're looking for an off grid sleeping porch in the red river gorge, this one has a nice wooded view."
Bungalow | 1 Bed, 0.5 Bath
1,600 Acres | Pool | Pond | Fishing | | WiFi near Red River Gorge, KY!
Pool

1,600 Acres | Pool | Pond | Fishing | | WiFi near Red River Gorge, KY!

8.4 out of 10, Very Good, (15)
"Everything was great, except for the pool that wasn't clean"
1,600 Acres | Pool | Pond | Fishing | | WiFi near Red River Gorge, KY!
Unique, Cozy Stay near Red River Gorge
Exterior

Unique, Cozy Stay near Red River Gorge

9.0 out of 10, Wonderful, (2)
"Love it ❤️"
The price is SAR 272
SAR 504 total
includes taxes & fees
20 Apr - 21 Apr
Unique, Cozy Stay near Red River Gorge
Cozy Cottage Perfect for Girls Night Away
Interior

Cozy Cottage Perfect for Girls Night Away

10.0 out of 10, Exceptional, (8)
"We rented this house for a 30th birthday weekend. It was as adorable as pictured with the girliest small touches that really set it apart from other options. We walked several places for shopping and eating. I hadn’t realized there was only one shower but it worked out just fine. Would definitely stay again. "
The price is SAR 1,857
SAR 3,307 total
includes taxes & fees
20 Apr - 21 Apr
Cozy Cottage Perfect for Girls Night Away
Cottage is located on scenic byway in beautiful bluegrass region of Lexington KY
Interior

Cottage is located on scenic byway in beautiful bluegrass region of Lexington KY

10.0 out of 10, Exceptional, (13)
"The house was awesome. It was perfect for the two of us the detail everything was pointed so nicely down to the coffee cups. Definitely staying in this place again if I could give it more than five stars, I would clean."
Cottage is located on scenic byway in beautiful bluegrass region of Lexington KY
Peaceful Mt Sterling Cabin: Deck & Fire Pit!
House (2 Bedrooms) | Private kitchen | Microwave, oven, stovetop, highchair

Peaceful Mt Sterling Cabin: Deck & Fire Pit!

3.0 star property
10.0 out of 10, Exceptional, (1)
Peaceful Mt Sterling Cabin: Deck & Fire Pit!
Historic JC Cock House - Downtown Lexington KY
Fridge, oven, stovetop, dishwasher

Historic JC Cock House - Downtown Lexington KY

10.0 out of 10, Exceptional, (1)
"Our family loved staying at the historic home in Lexington. The house and gardens are beautiful. John is a wonderful host who thought of everything for the house. Decorating is tops. Gardens are lovey and lush. Great stop for our weekend trip to KY."
Historic JC Cock House - Downtown Lexington KY
Georgetown Home ~ 6 Mi to Kentucky Horse Park!
Dishwasher, paper towels

Georgetown Home ~ 6 Mi to Kentucky Horse Park!

3.0 star property
Georgetown Home ~ 6 Mi to Kentucky Horse Park!
Lexington Getaway w/ Backyard Deck < 2 Mi to UK!
Interior

Lexington Getaway w/ Backyard Deck < 2 Mi to UK!

3.0 star property
Lexington Getaway w/ Backyard Deck < 2 Mi to UK!
~ 2 Mi From UK: Gorgeous Lexington Retreat!
Interior

~ 2 Mi From UK: Gorgeous Lexington Retreat!

3.0 star property
10.0 out of 10, Exceptional, (1)
"The house is charming, extremely clean and comfy. The linens and access to helpful kitchen items is a bonus. The ease of booking and gaining access waa seamless. The only little thing was that the sofa bed was in the same room with queen bed. We didnt need to use it but if our other guest had joined the trip it would have been difficult. The king and queen beds are very comfy. "
~ 2 Mi From UK: Gorgeous Lexington Retreat!
Lexington Home ~ 2 Mi to University of Kentucky!
House (3 Bedrooms) | Private kitchen | Microwave, oven, stovetop, dishwasher

Lexington Home ~ 2 Mi to University of Kentucky!

3.0 star property
Lexington Home ~ 2 Mi to University of Kentucky!
Quaint Creekside Cottage w/ Porch & Backyard!
Miscellaneous

Quaint Creekside Cottage w/ Porch & Backyard!

3.0 star property
Quaint Creekside Cottage w/ Porch & Backyard!
Lexington Home ~ 5 Mi to University of Kentucky!
House (3 Bedrooms) | Private kitchen | Oven, stovetop, dishwasher, blender

Lexington Home ~ 5 Mi to University of Kentucky!

3.0 star property
Lexington Home ~ 5 Mi to University of Kentucky!
Cozy Georgetown Cottage on a Working Horse Farm!
TV

Cozy Georgetown Cottage on a Working Horse Farm!

10.0 out of 10, Exceptional, (1)
Cozy Georgetown Cottage on a Working Horse Farm!
Family Home w/ Ping-pong & Fire Pit in Lexington
Interior

Family Home w/ Ping-pong & Fire Pit in Lexington

3.0 star property
Family Home w/ Ping-pong & Fire Pit in Lexington
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.
Don't see what you're looking for?
See all available properties in Winchester
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Other property types in Winchester

Natural Bridge State Resort Park
Seasonal outdoor pool

Natural Bridge State Resort Park

3.5 star property
8.6 out of 10, Excellent, (1526)
"We stayed in a cottage. The cottage needs a lot of repairs. We had to climb 36 stairs in rainy conditions to reach our cabin. The complimentary breakfast was nice. The staff were all friendly and helpful. The walk to the restaurant from the cottages was outstanding and fun. Despite the state of disrepair to our cabin, we would still recommend this location as a must-do family adventure and destination."
The price is SAR 435
SAR 480 total
includes taxes & fees
29 Apr - 30 Apr
Natural Bridge State Resort Park
Hot Tub, WiFi & Pet-Friendly - Secluded Family Getaway - Pilot Point - Red River Gorge, Kentucky!
Outdoor spa tub

Hot Tub, WiFi & Pet-Friendly - Secluded Family Getaway - Pilot Point - Red River Gorge, Kentucky!

9.6 out of 10, Exceptional, (141)
"Cozy, clean and comfortable cabin!"
The price is SAR 425
SAR 864 total
includes taxes & fees
11 May - 12 May
Hot Tub, WiFi & Pet-Friendly - Secluded Family Getaway - Pilot Point - Red River Gorge, Kentucky!
Tranquil Getaway in the Woods ~ Sunset Ridge
Terrace/patio

Tranquil Getaway in the Woods ~ Sunset Ridge

9.8 out of 10, Exceptional, (53)
"My girlfriends and I loved the quaint cabin. The firepit was great! Beds are comfortable and comes with plenty of kitchen amenities! I would recommend adding a curtain option for the bed by the window.. Though it's off the beaten path, we were removed enough from others and no issue of safety."
The price is SAR 394
SAR 558 total
includes taxes & fees
22 Apr - 23 Apr
Tranquil Getaway in the Woods ~ Sunset Ridge
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.