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Find Family Hotels in Winchester, KY from CA $72

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Check availability on Winchester Family Hotels

Top Winchester Family Hotels

Hampton Inn Winchester
Suite, 1 King Bed, Non Smoking

Hampton Inn Winchester

2.5 star property
9.2 out of 10, Wonderful, (435)
"Property was nice"
The price is CA $164
CA $181 total
includes taxes & fees
Aug 31 - Sep 1
Hampton Inn Winchester
Hot Tub & WiFi - Family Log Cabin - Cozy Canopy - Red River Gorge, Kentucky!
TV, books

Hot Tub & WiFi - Family Log Cabin - Cozy Canopy - Red River Gorge, Kentucky!

9.6 out of 10, Exceptional, (297)
"The cabin is lovely! Everything was clean and all the extras provided made this a comfortable stay. "
The price is CA $144
CA $289 total
includes taxes & fees
Sep 10 - Sep 11
Hot Tub & WiFi - Family Log Cabin - Cozy Canopy - Red River Gorge, Kentucky!
Hot Tub - Tiny A-Frame Cabin - Haven at the Red - Red River Gorge, Kentucky!
Interior

Hot Tub - Tiny A-Frame Cabin - Haven at the Red - Red River Gorge, Kentucky!

8.4 out of 10, Very good, (123)
"This cabin is great! The wrap around deck is awesome for hanging out in the evenings, and the loft bedroom was super cool."
The price is CA $149
CA $297 total
includes taxes & fees
Aug 20 - Aug 21
Hot Tub - Tiny A-Frame Cabin - Haven at the Red - Red River Gorge, Kentucky!
Hot Tub & WiFi - Intimate Cabin - Snuggle Inn - Red River Gorge, Kentucky!
Terrace/patio

Hot Tub & WiFi - Intimate Cabin - Snuggle Inn - Red River Gorge, Kentucky!

9.4 out of 10, Exceptional, (124)
"We enjoyed the cabin it was a super cute place. My only complaint was when we arrived the couch was torn up and there was cookies all over it. Other than that it was a great place, close to everything you want to experience "
The price is CA $224
CA $409 total
includes taxes & fees
Aug 17 - Aug 18
Hot Tub & WiFi - Intimate Cabin - Snuggle Inn - Red River Gorge, Kentucky!
Hot Tub, WiFi, Pet-Friendly - Family Cabin - Sundance - Red River Gorge, Kentucky!
Exterior

Hot Tub, WiFi, Pet-Friendly - Family Cabin - Sundance - Red River Gorge, Kentucky!

9.4 out of 10, Exceptional, (130)
"We absolutely loved this property and wish we could’ve stayed longer. Very peaceful and quiet. Clean and cozy; private. Loved exploring the creek next to it. Just a perfect get away. "
The price is CA $226
CA $411 total
includes taxes & fees
Aug 26 - Aug 27
Hot Tub, WiFi, Pet-Friendly - Family Cabin - Sundance - Red River Gorge, Kentucky!
Hot Tub, WiFi, Pet-Friendly - Family Cabin - Mountain Spirit - Red River Gorge, Kentucky!
Smart TV, fireplace, DVD player, books

Hot Tub, WiFi, Pet-Friendly - Family Cabin - Mountain Spirit - Red River Gorge, Kentucky!

9.2 out of 10, Wonderful, (106)
"Cozy cabin! We enjoyed our stay"
The price is CA $202
CA $381 total
includes taxes & fees
Aug 26 - Aug 27
Hot Tub, WiFi, Pet-Friendly - Family Cabin - Mountain Spirit - Red River Gorge, Kentucky!
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, (151)
"Was an amazing stay"
The price is CA $164
CA $327 total
includes taxes & fees
Aug 28 - Aug 29
Hot Tub, WiFi & Pet-Friendly - Secluded Family Getaway - Pilot Point - Red River Gorge, Kentucky!
Sits on 8 private Acres, hiking trails at this secluded chalet! Wi-Fi, Hot Tub
Property grounds

Sits on 8 private Acres, hiking trails at this secluded chalet! Wi-Fi, Hot Tub

9.6 out of 10, Exceptional, (42)
"Loved the hot tub and sunsets "
Sits on 8 private Acres, hiking trails at this secluded chalet! Wi-Fi, Hot Tub
Artistic Lodging Queen suite
Interior

Artistic Lodging Queen suite

9.2 out of 10, Wonderful, (42)
"What an enjoyable experience! The home is beautiful and I love all the art!!!!"
The price is CA $103
CA $175 total
includes taxes & fees
Aug 31 - Sep 1
Artistic Lodging Queen suite
Artistic Lodging King Suite
1 bedroom, iron/ironing board, WiFi, bed sheets

Artistic Lodging King Suite

9.2 out of 10, Wonderful, (70)
"We were just passing through the area but this was a lovely stay, very comfortable and cute, and very clean!"
The price is CA $124
CA $197 total
includes taxes & fees
Aug 31 - Sep 1
Artistic Lodging King Suite
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.

Top Winchester Hotel Reviews

Hyatt Place Lexington

Hyatt Place Lexington

10/10 Excellent
"We had a great stay while passing through Kentucky on the way to Tennessee. Staff were very helpful and informative. We reported a window problem and we were told the hotel was going to be renovated later this fall. The small bar was nice. Lots of places to eat within walking distance. "
Kelly 1-night trip
Posted 9 hours ago
Hyatt Place Lexington

Frequently asked questions

What's Winchester like for family-friendly vacations?
The welcoming destination of Winchester is a great choice if you've been thinking about a vacation with the kids. The excursions, football games, and cafes are just some of the things that make this an attractive family vacation spot. Arrange a flight into Blue Grass Airport (LEX), which is located 23 mi (37.1 km) from the city center.
What's the best place to stay for families in Winchester?
Hampton Inn Winchester is a hotel with free parking and free breakfast, and it's a top choice on Expedia for families.
How many hotels that welcome families will I be able to find in Winchester?
Expedia has 6 family-friendly hotels and other accommodations in Winchester.
When's the best time to book a family-friendly vacation in Winchester?
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 38°F. Average annual precipitation for Winchester is 56 inches.
What's there to see and do with your family in Winchester?
While you are visiting Winchester, you might want to round up the kiddos and make time to see interesting attractions such as Clark County Public Library and Hamburg Pavilon. Make sure you have lots of time for activities like Hamburg Place and Claiborne Farm.