Hot Winchester Bed & Breakfast 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 B&B in Winchester

Blue Heron B&B and Retreat Center

Blue Heron B&B and Retreat Center

3.5 out of 5
270 E. Prong Road, Richmond, KY
With a stay at Blue Heron B&B and Retreat Center in Richmond, you'll be 5.9 mi (9.5 km) from Fort Boonesborough State Park and 9 mi (14.5 km) from Eastern Kentucky ...
Blue Heron B&B and Retreat Center
Lyndon House B&B

Lyndon House B&B

3 out of 5
507 N Broadway, Lexington, KY
The price is AU$452 per night from 6 Dec to 7 Dec
AU$452
includes taxes & fees
6 Dec - 7 Dec
With a stay at Lyndon House B&B in Lexington (Northside District), you'll be within a 5-minute drive of West Sixth Brewing and Lexington Brewing & Distilling ...
Lyndon House B&B
The Guesthouse at Rosecrest Farm

The Guesthouse at Rosecrest Farm

3 out of 5
1276 Winchester Road, Paris, KY
Located in Paris, The Guesthouse at Rosecrest Farm is a 3-minute drive from Claiborne Farm and 5 minutes from Hopewell Museum.
The Guesthouse at Rosecrest Farm
Save an average of 15% on thousands of hotels when you're signed in
Stylish Kentucky hospitality

Stylish Kentucky hospitality

Lexington
The price is AU$2,970 per night from 11 Nov to 12 Nov
AU$2,970
includes taxes & fees
11 Nov - 12 Nov
With a stay at this bed & breakfast, you'll be centrally located in Lexington, within a 5-minute drive of Rupp Arena and University of Kentucky.
Stylish Kentucky hospitality
Artistic Lodging Queen suite

Artistic Lodging Queen suite

Paris
With a stay at this bed & breakfast in Paris, you'll be within a 5-minute walk of Duncan Tavern Historic Center and Hopewell Museum.
Artistic Lodging Queen suite
The Bennett House Bed & Breakfast

The Bennett House Bed & Breakfast

3 out of 5
419 W Main St, Richmond, KY
Located in Richmond, The Bennett House Bed & Breakfast is in the historical district, within a 5-minute walk of Richmond Area Arts Center and Eastern Kentucky ...
The Bennett House Bed & Breakfast
Chateau Annette

Chateau Annette

3.5 out of 5
4950 Jennie Kate Lane, Lexington, KY
With a stay at Chateau Annette in Lexington, you'll be within a 10-minute drive of The Kentucky Castle and Keeneland Racing Course.
Chateau Annette
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.

B&Bs in Winchester

We know why you’re here. You forgot something, though we’re not sure what. A birthday or an anniversary, maybe. And this time, a bouquet of fresh flowers and a homemade breakfast in bed aren’t going to cut it. You’re determined your special someone is going to feel like the centre of the universe on whatever special day you have coming up—that’s where lastminute.com.au comes in, and that’s also where Winchester B&B accommodation comes in.

You can’t go wrong with a romantic getaway to a bed and breakfast. It’s the stuff of poetry, novels, and of course, any good rom-com. You can snuggle under the covers all morning if you like, although the delicious aromas of a home-cooked breakfast are likely to get you out of bed. Even a cheap B&B will have a delectable morning meal included—and you don’t have to make it yourself. After all, that’s kind of the whole point. Add in a boutique feel and the charming Winchester vibes, and you’ll get why B&Bs are great for couples, families, and even your doggo. Yes, pet-friendly B&Bs are a thing, and although we can’t guarantee the dog will get his own breakfast, you’re more than happy to share, aren’t you?

Hey, if you’re gonna stay in a B and B in Winchester, you want it to be awesome, don’t you? Well then, check out lastminute.com.au and get to planning. We’ve got everything from luxury to budget bed & breakfasts, and our great prices leave you plenty of cash to splash in Winchester. No need to thank us—we know how great we are.

Winchester B&B essential information

Accommodation
7 B&B
Lowest Price
AU$102
Highest Price
AU$2,970
Popular accommodation
Blue Heron B&B and Retreat Center, Lyndon House B&B, The Guesthouse at Rosecrest Farm, Stylish Kentucky hospitality, Artistic Lodging Queen suite, The Bennett House Bed & Breakfast, Chateau Annette

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$102 per night from 24 Nov to 25 Nov
AU$102
includes taxes & fees
24 Nov - 25 Nov
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$158 per night from 12 Nov to 13 Nov
AU$158
includes taxes & fees
12 Nov - 13 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$102 per night from 6 Nov to 7 Nov
AU$102
includes taxes & fees
6 Nov - 7 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
Save an average of 15% on thousands of hotels when you're signed in
Hilton Lexington/Downtown

Hilton Lexington/Downtown

3.5 out of 5
369 West Vine Street, Lexington, KY
The price is AU$230 per night from 27 Nov to 28 Nov
AU$230
includes taxes & fees
27 Nov - 28 Nov
Hilton Lexington/Downtown is centrally located in Lexington, a 3-minute walk from Lexington Opera House and 5 minutes by foot from Rupp Arena.
Hilton Lexington/Downtown
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.