Hot Winchester Cottage Rates

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Featured Cottages in Winchester

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

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

Stanton
Located in Stanton, this cottage is within a 15-minute drive of Daniel Boone National Forest and Kentucky Reptile Zoo.
1 bed cottage, grill, fire pit, Very close to Red River Gorge!!
Homey Horse Farm Hideaway ~ 6 Mi to KY Horse Park!

Homey Horse Farm Hideaway ~ 6 Mi to KY Horse Park!

Lexington
With a stay at this cottage in Lexington, you'll be within a 10-minute drive of Kentucky Horse Park and Rupp Arena.
Homey Horse Farm Hideaway ~ 6 Mi to KY Horse Park!
Springside BoHo Getaway

Springside BoHo Getaway

Georgetown
With a stay at this cottage, you'll be centrally located in Georgetown, within a 10-minute drive of Kentucky Horse Park and Georgetown College.
Springside BoHo Getaway
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Mountaintop Cottage

Mountaintop Cottage

2 out of 5
Stanton
When you stay at this cottage in Stanton, you'll be steps from Daniel Boone National Forest.
Mountaintop Cottage
Bungalow | 1 Bed, 0.5 Bath

Bungalow | 1 Bed, 0.5 Bath

Stanton
The price is AU$314 per night from 23 Nov to 24 Nov
AU$314
includes taxes & fees
23 Nov - 24 Nov
With a stay at this cottage in Stanton, you'll be within a 15-minute drive of Red River Gorge and Natural Bridge State Park.
Bungalow | 1 Bed, 0.5 Bath
Cozy 1 bedroom cottage on picturesque horse farm

Cozy 1 bedroom cottage on picturesque horse farm

Georgetown
Located in Georgetown, this cottage is in a rural location, within a 10-minute drive of Toyota Visitor Center and Cherry Blossom Golf and Country Club.
Cozy 1 bedroom cottage on picturesque horse farm
1,600 Acres | Pool | Pond | Fishing | | WiFi near Red River Gorge, KY!

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

Clay City
When you stay at this cottage in Clay City, you'll be in the mountains and steps from Daniel Boone National Forest.
1,600 Acres | Pool | Pond | Fishing | | WiFi near Red River Gorge, KY!
Unique, Cozy Stay near Red River Gorge

Unique, Cozy Stay near Red River Gorge

Slade
With a stay at this cottage in Slade, you'll be within a 15-minute drive of Natural Bridge State Park and Red River Gorge.
Unique, Cozy Stay near Red River Gorge
Cozy Georgetown Cottage on a Working Horse Farm!

Cozy Georgetown Cottage on a Working Horse Farm!

Georgetown
With a stay at this cottage in Paris, you'll be 10.7 mi (17.2 km) from Kentucky Horse Park and 25.6 mi (41.2 km) from Rupp Arena.
Cozy Georgetown Cottage on a Working Horse Farm!
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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 Budget-Friendly Cottage Accommodation

Adulting can be rough. You love your job, and your sweetheart is the best, but next time someone says “think outside the box” or “we’ll park that”, you just might throw a fit. When was the last time you had one of those really deep convos with your person, anyway? It sounds like you need a holiday, and you’ve come to the right place. Budget-friendly cottage accommodation in Winchester will have you feeling like your SO is the peanut butter to your jelly again in no time.

We’re not here to tell you what you want—we think you already know. You want a spot that’s totally relaxing, but still has plenty of things to do, you know, if you feel like it. You want great scenery, and you want food that’s worthy of your number one hashtag: #nomnom. Cottage getaways to Winchester definitely fit the bill.

Yes, the scenery is stunning, but on a romantic cottage holiday, it’s what’s inside that counts. Today’s cottages are filled with those little touches of luxury, like fine bath amenities and gourmet kitchens. You know the saying about how the way to someone’s heart is through their stomach? Don’t miss your chance to impress this holiday—even if that just means remembering their favourite wine. (Hey, that still counts!)

Before you can check out entirely, you’ve got a few last bits of adulting to take care of: pick your perfect cheap country cottage in Winchester, then type up that email to your boss and request your annual leave. We’re sure they’ll understand.

Winchester Cottages essential information

Accommodation
28 Cottages
Lowest Price
AU$105
Highest Price
AU$314
Popular accommodation
1 bed cottage, grill, fire pit, Very close to Red River Gorge!!, Homey Horse Farm Hideaway ~ 6 Mi to KY Horse Park!, Springside BoHo Getaway , Mountaintop Cottage , Bungalow | 1 Bed, 0.5 Bath, Cozy 1 bedroom cottage on picturesque horse farm, 1,600 Acres | Pool | Pond | Fishing | | WiFi near Red River Gorge, KY!, Unique, Cozy Stay near Red River Gorge, Cozy Georgetown Cottage on a Working Horse Farm!

Top trending hotels in Winchester

Quality Inn Lexington -Horse Park

Quality Inn Lexington -Horse Park

2.5 out of 5
1938 Stanton Way, Bldg A, Lexington, KY
Fully refundableReserve now, pay when you stay
The price is AU$105 per night from 8 Dec to 9 Dec
AU$105
includes taxes & fees
8 Dec - 9 Dec
Located in Lexington, Quality Inn Lexington -Horse Park is within a 10-minute drive of Lexington Convention Center and Rupp Arena.
Quality Inn Lexington -Horse Park
GLō Best Western Lexington

GLō Best Western Lexington

3 out of 5
1935 Stanton Way, Lexington, KY
Fully refundableReserve now, pay when you stay
The price is AU$141 per night from 25 Nov to 26 Nov
AU$141
includes taxes & fees
25 Nov - 26 Nov
Located in Lexington, GLō Best Western Lexington is in the business district, within a 10-minute drive of Lexington Convention Center and Lexington Brewing & ...
GLō Best Western Lexington
GuestHouse Lexington

GuestHouse Lexington

2.5 out of 5
2261 Elkhorn Road, Lexington, KY
Fully refundableReserve now, pay when you stay
The price is AU$120 per night from 24 Nov to 25 Nov
AU$120
includes taxes & fees
24 Nov - 25 Nov
When you stay at GuestHouse Lexington in Lexington, you'll be in a shopping district, within a 10-minute drive of Rupp Arena and University of Kentucky.
GuestHouse Lexington
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The Manchester

The Manchester

4 out of 5
941 Manchester St, Lexington, KY
Fully refundableReserve now, pay when you stay
The price is AU$287 per night from 23 Dec to 24 Dec
AU$287
includes taxes & fees
23 Dec - 24 Dec
With a stay at The Manchester in Lexington, you'll be in the historical district, within a 15-minute walk of Rupp Arena and Lexington Convention Center.
The Manchester
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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.