Hot Winchester Cottage Rates

More Flash, Less Cash - Take advantage of our Price Pledge** (even on luxey stays)

We keep it easy with the option to pay now or later on select accommodation

Book up 'til the last second - millions of rooms to crash tonight^

Featured Cottages in Winchester

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

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

Lexington
With a stay at this cottage, you'll be centrally located in Lexington, within a 15-minute drive of University of Kentucky and Rupp Arena.
Charming Cottage Home On A Farm In The Kentucky Horse Country! Relax!
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, a 4-minute drive from Country Boy Brewing and 6 minutes from Toyota Visitor Center.
Cozy 1 bedroom cottage on picturesque horse farm
Mountaintop Cottage

Mountaintop Cottage

2 out of 5
Stanton
The price is AU$306 per night from 10 May to 11 May
AU$306
includes taxes & fees
10 May - 11 May
With a stay at this cottage in Stanton, you'll be 16 mi (25.7 km) from Red River Gorge and 16.7 mi (26.8 km) from Natural Bridge State Park.
Mountaintop Cottage
Save an average of 15% on thousands of hotels when you're signed in
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
Bungalow | 1 Bed, 0.5 Bath

Bungalow | 1 Bed, 0.5 Bath

Stanton
The price is AU$320 per night from 25 Apr to 26 Apr
AU$320
includes taxes & fees
25 Apr - 26 Apr
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
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
With a stay at this cottage in Clay City, you'll be in the mountains, and 22.3 mi (35.9 km) from Red River Gorge and 21.9 mi (35.2 km) from Natural Bridge State ...
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
The price is AU$214 per night from 27 Apr to 28 Apr
AU$214
includes taxes & fees
27 Apr - 28 Apr
With a stay at this cottage in Slade, you'll be within a 15-minute drive of Red River Gorge and Natural Bridge State Park.
Unique, Cozy Stay near Red River Gorge
Cozy Cottage Perfect for Girls Night Away

Cozy Cottage Perfect for Girls Night Away

Lexington
With a stay at this cottage in Lexington, you'll be within a 5-minute drive of Rupp Arena and University of Kentucky.
Cozy Cottage Perfect for Girls Night Away
Cottage is located on scenic byway in beautiful bluegrass region of Lexington KY

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

Lexington
Located in Lexington, this cottage is in a rural location, a 4-minute drive from Boone Station State Historic Site and 6 minutes from Lexington Sporting Club ...
Cottage is located on scenic byway in beautiful bluegrass region of Lexington KY
Don't see what you're looking for?
See all available properties in Winchester
View all properties
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
34 Cottages
Lowest Price
AU$107
Highest Price
AU$330
Popular accommodation
Charming Cottage Home On A Farm In The Kentucky Horse Country! Relax! , Cozy 1 bedroom cottage on picturesque horse farm, Mountaintop Cottage , Springside BoHo Getaway , Bungalow | 1 Bed, 0.5 Bath, 1,600 Acres | Pool | Pond | Fishing | | WiFi near Red River Gorge, KY!, Unique, Cozy Stay near Red River Gorge, Cozy Cottage Perfect for Girls Night Away, Cottage is located on scenic byway in beautiful bluegrass region of Lexington KY

Top trending hotels in Winchester

Baymont by Wyndham Winchester

Baymont by Wyndham Winchester

2.5 out of 5
960 Interstate Dr, Winchester, KY
Fully refundableReserve now, pay when you stay
The price is AU$138 per night from 11 May to 12 May
AU$138
includes taxes & fees
11 May - 12 May
With a stay at Baymont by Wyndham Winchester in Winchester, you'll be within a 5-minute drive of Lykins Park and The Holler.
Baymont by Wyndham Winchester
The Manchester

The Manchester

4 out of 5
941 Manchester St, Lexington, KY
Fully refundableReserve now, pay when you stay
The price is AU$330 per night from 5 May to 6 May
AU$330
includes taxes & fees
5 May - 6 May
With a stay at The Manchester in Lexington (Distillery District), you'll be within a 5-minute drive of Lexington Convention Center and Rupp Arena.
The Manchester
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$121 per night from 21 May to 22 May
AU$121
includes taxes & fees
21 May - 22 May
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
Save an average of 15% on thousands of hotels when you're signed in
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$107 per night from 25 May to 26 May
AU$107
includes taxes & fees
25 May - 26 May
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
Don't see what you're looking for?
See all available properties in Winchester
View all properties
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.

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.