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Check prices for these dates

Next weekend
Dec 19 - Dec 21
In two weeks
Dec 26 - Dec 28
In one month
Jan 9 - Jan 11
In two months
Feb 6 - Feb 8
No exact matches found, but these alternatives could be just right

Recommended hotels in Winchester

Lobby
Days Inn by Wyndham Maysville Kentucky

Days Inn by Wyndham Maysville Kentucky

Days Inn by Wyndham Maysville Kentucky
2.5 star property
Maysville
7.0 out of 10, Good, (396)
"Nothing fancy but out of the way and quiet "
United States
david
$60 nightly
The price is $67
Jan 11 - Jan 12, 2026
Total with taxes and fees
Days Inn by Wyndham Maysville Kentucky
Exterior
Quality Inn Seaman

Quality Inn Seaman

Quality Inn Seaman
2.5 star property
Seaman
7.4 out of 10, Good, (293)
"Very helpful and friendly staff! We were in the area for a few days of hiking. This was a convenient place to stay with a very affordable price especially since breakfast was included."
United States
Douglas
$85 nightly
The price is $94
Jan 11 - Jan 12, 2026
Total with taxes and fees
Quality Inn Seaman
Standard Double Room | Desk, laptop workspace, blackout drapes, iron/ironing board
Country Nights Inn

Country Nights Inn

Country Nights Inn
2.5 star property
West Union
8.0 out of 10, Very Good, (46)
"For the price, one of the best stays I have had in a long time."
United States
Matt
$64 nightly
The price is $71
Jan 1 - Jan 2, 2026
Total with taxes and fees
Country Nights Inn
Front of property
French Quarter Inn

French Quarter Inn

French Quarter Inn
3.0 star property
Maysville
8.8 out of 10, Excellent, (760)
"Super clean room and amazing staff. Right by downtown maysville so we could walk everywhere "
United States
Roy
$110 nightly
The price is $122
Jan 1 - Jan 2, 2026
Total with taxes and fees
French Quarter Inn
BBQ/picnic area
Brown's Motel Aberdeen

Brown's Motel Aberdeen

Brown's Motel Aberdeen
2.0 star property
Aberdeen
7.4 out of 10, Good, (265)
"Very nice stay will stay again "
United States
Arthur
$50 nightly
The price is $56
Dec 12 - Dec 13
Total with taxes and fees
Brown's Motel Aberdeen
Front of property
Countryside Inn & Suites

Countryside Inn & Suites

Countryside Inn & Suites
2.5 star property
Mount Orab
7.2 out of 10, Good, (548)
"Great place, just the breakfast could've been better "
United States
SHAWN
$86 nightly
The price is $97
Dec 28 - Dec 29
Total with taxes and fees
Countryside Inn & Suites
Standard Penthouse, Pool View | Private kitchen | Mini-fridge, microwave
Beverly hills inn

Beverly hills inn

Beverly hills inn
2.5 star property
Aberdeen
8.6 out of 10, Excellent, (156)
"Nice place to stay "
United States
Deborah
$46 nightly
The price is $51
Jan 11 - Jan 12, 2026
Total with taxes and fees
Beverly hills inn
1 bedroom, free WiFi, bed sheets
Meadowview Guest House -Couple's Hot Tub Getaway-1 Bedroom Studio

Meadowview Guest House -Couple's Hot Tub Getaway-1 Bedroom Studio

Meadowview Guest House -Couple's Hot Tub Getaway-1 Bedroom Studio
Hillsboro
10.0 out of 10, Exceptional, (18)
"I was out there for a wedding and this place was great for a weekend trip."
United States
L
$157 nightly
The price is $157
Dec 14 - Dec 15
Total with taxes and fees
Meadowview Guest House -Couple's Hot Tub Getaway-1 Bedroom Studio
Standard Room, 2 Double Beds | Blackout drapes, soundproofing, free WiFi, bed sheets
Paragon Inn Hillsboro

Paragon Inn Hillsboro

Paragon Inn Hillsboro
2.0 star property
Hillsboro
7.6 out of 10, Good, (193)
"Staff very friendly and gave me a room with a walk in shower I really liked that. "
United States
Charles
$71 nightly
The price is $79
Dec 20 - Dec 21
Total with taxes and fees
Paragon Inn Hillsboro
Vending machine
Greystone Motel

Greystone Motel

Greystone Motel
2.5 star property
Hillsboro
6.6 out of 10, (176)
"The area is off the beaten path. It's quiet and I felt safe. It's pet friendly and I just needed a clean safe place to stay for an event nearby. I would stay here again."
United States
Jana
$63 nightly
The price is $70
Dec 12 - Dec 13
Total with taxes and fees
Greystone Motel
Studio Suite, 1 King Bed, Non Smoking | Desk, laptop workspace, blackout drapes, iron/ironing board
Days Inn by Wyndham Hillsboro

Days Inn by Wyndham Hillsboro

Days Inn by Wyndham Hillsboro
2.5 star property
Hillsboro
7.2 out of 10, Good, (278)
"Room very clean and comfortable "
United States
Robert
$98 nightly
The price is $108
Dec 14 - Dec 15
Total with taxes and fees
Days Inn by Wyndham Hillsboro
Double Room, 2 Double Beds | Desk, free cribs/infant beds, rollaway beds, free WiFi
Super 8 by Wyndham Maysville KY

Super 8 by Wyndham Maysville KY

Super 8 by Wyndham Maysville KY
2.0 star property
Maysville
7.0 out of 10, Good, (416)
"Quiet area, easy parking "
United States
Dan
$69 nightly
The price is $77
Dec 14 - Dec 15
Total with taxes and fees
Super 8 by Wyndham Maysville KY
Exterior
Glamping Cabin | Huge Window | Cliff and Animal Views

Glamping Cabin | Huge Window | Cliff and Animal Views

Glamping Cabin | Huge Window | Cliff and Animal Views
Green Township
10.0 out of 10, Exceptional, (2)
"We had a great stay, we loved the horse and goats. It was peaceful and beautiful, exactly what we needed! Will definitely stay again! "
United States
Callie J.
$114 nightly
The price is $114
Dec 14 - Dec 15
Total with taxes and fees
Glamping Cabin | Huge Window | Cliff and Animal Views
Desk, free WiFi, bed sheets
Quality Inn Maysville

Quality Inn Maysville

Quality Inn Maysville
2.5 star property
Maysville
6.2 out of 10, (189)
"Clean place staff awesome and mazing "
Canada
martin
$69 nightly
The price is $77
Dec 14 - Dec 15
Total with taxes and fees
Quality Inn Maysville
Property grounds
Glamping Cabin | Huge Window | Over a Creek

Glamping Cabin | Huge Window | Over a Creek

Glamping Cabin | Huge Window | Over a Creek
Green Township
9.8 out of 10, Exceptional, (8)
"Had a wonderful time! Bathrooms and cabin were very clean and it was very quiet. Just what we needed."
United States
Kristen W.
$114 nightly
The price is $114
Dec 14 - Dec 15
Total with taxes and fees
Glamping Cabin | Huge Window | Over a Creek
Fridge, microwave, stovetop, coffee/tea maker
Bear Necessities Cabin - What Else Do You Need?

Bear Necessities Cabin - What Else Do You Need?

Bear Necessities Cabin - What Else Do You Need?
West Union
10.0 out of 10, Exceptional, (9)
"Great little spot! Cabin is super nice inside and out."
United States
Jason M.
$155 nightly
The price is $161
Dec 12 - Dec 13
Total with taxes and fees
Bear Necessities Cabin - What Else Do You Need?
Room, 2 Queen Beds | Desk, rollaway beds, free WiFi, bed sheets
Hillsboro Inn & Suites

Hillsboro Inn & Suites

Hillsboro Inn & Suites
2.0 star property
Hillsboro
6.4 out of 10, (39)
"Very nice room for the price"
United States
James
$72 nightly
The price is $79
Dec 12 - Dec 13
Total with taxes and fees
Hillsboro Inn & Suites
1 bedroom, WiFi
Home away from Home! - 1BR apartment in Maysville

Home away from Home! - 1BR apartment in Maysville

Home away from Home! - 1BR apartment in Maysville
Maysville
10.0 out of 10, Exceptional, (13)
"Amazing stay. We would definitely recommend this place to anyone!"
United States
John H.
$105 nightly
The price is $107
Dec 12 - Dec 13
Total with taxes and fees
Home away from Home! - 1BR apartment in Maysville
Fridge, stovetop, toaster, cookware/dishes/utensils
Sleeps 4| Private Bathroom | Stunning Views

Sleeps 4| Private Bathroom | Stunning Views

Sleeps 4| Private Bathroom | Stunning Views
Green Township
10.0 out of 10, Exceptional, (1)
$155 nightly
The price is $155
Dec 14 - Dec 15
Total with taxes and fees
Sleeps 4| Private Bathroom | Stunning Views
Property grounds
Glamping Cabin | Huge Window | Tree House Feel

Glamping Cabin | Huge Window | Tree House Feel

Glamping Cabin | Huge Window | Tree House Feel
Green Township
9.0 out of 10, Wonderful, (19)
"The perfect place to connect with nature and enjoy a beautiful landscape the attention was great the beautiful place the super comfortable cabin I would come back again"
Mexico
Víctor Manuel
$114 nightly
The price is $114
Dec 14 - Dec 15
Total with taxes and fees
Glamping Cabin | Huge Window | Tree House Feel
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

French Quarter Inn

French Quarter Inn

10/10 Excellent
"Super clean room and amazing staff. Right by downtown maysville so we could walk everywhere "
Roy 1-night trip
Posted 5 days ago
French Quarter Inn

Find out more about Winchester

Winchester B&B information

Number of reviews
3,815
Accommodation
1 B&B
Lowest Price
$51
Highest Price
$161

Frequently asked questions

Searching for B&Bs in Winchester?
If you're looking for something a little quirkier than your standard hotel experience, a bed and breakfast might be the perfect option for your vacation.
How do you know if a B&B is a good option for your stay?
With attentive service, opportunities to socialize with other guests, and tasty breakfasts, B&Bs offer a unique setting.
What's the best time of year to book my B&B in Winchester?
When you're dreaming of a trip to Winchester, year-round temperatures and rainfall may be important factors to consider. The hottest months are usually July and August with an average temp of 72°F, while the coldest months are January and February with an average of 37°F. Average annual precipitation for Winchester is 50 inches.
How can I get to and around Winchester?
Mapping out your trip in and around Winchester is easy with these transportation options. Fly into Cincinnati, OH (LUK-Cincinnati Municipal - Lunken Field), which is located 43.2 mi (69.6 km) away from the city center. You can also search for flights into Cincinnati-Northern Kentucky Int'l Airport (CVG), which is 54.6 mi (87.9 km) away. If you'd like to explore around the area, consider renting a car to take in more sights.

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