Holiday Homes in Carlisle

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Check prices for these dates

Next weekend
15 Aug - 17 Aug
In two weeks
22 Aug - 24 Aug
In one month
5 Sept - 7 Sept
In two months
3 Oct - 5 Oct

Featured Holiday Homes in Carlisle and around

Sprawling Kentucky Getaway w/ Private Pool!
Stunning two-story house with a prominent tower and wrap-around porch, surrounded by a beautifully maintained lawn and outdoor recreational facilities.

Sprawling Kentucky Getaway w/ Private Pool!

2.0 star property
9.8 out of 10, Exceptional, (7)
"Enjoyed it"
Sprawling Kentucky Getaway w/ Private Pool!
Private Country Estate: 16 miles to Keeneland, 13 to KY Horse Park!
Traditional interior with a dining area, living room, and hallway, featuring a vaulted ceiling and large window.

Private Country Estate: 16 miles to Keeneland, 13 to KY Horse Park!

10.0 out of 10, Exceptional, (47)
"Our stay was relaxing and very comfortable. Would stay again "
Private Country Estate: 16 miles to Keeneland, 13 to KY Horse Park!
4 Bed 3 bath clean , spacious all brick home , welcome families and work groups
Enjoy cooking in this well-equipped kitchen with a stove, oven, and dishwasher.

4 Bed 3 bath clean , spacious all brick home , welcome families and work groups

10.0 out of 10, Exceptional, (3)
"Great accommodation. "
4 Bed 3 bath clean , spacious all brick home , welcome families and work groups
Modern Barndo/Hot Tub/Fire Pit/Rec Room/20min RRG
Property grounds

Modern Barndo/Hot Tub/Fire Pit/Rec Room/20min RRG

Modern Barndo/Hot Tub/Fire Pit/Rec Room/20min RRG
The Manor at Maysville Golf Course View
Cozy living room with a fireplace, sofa, and two side tables.

The Manor at Maysville Golf Course View

9.8 out of 10, Exceptional, (22)
"Our families got together for a lovely Christmas gathering here. The house was beautifully decorated!"
The Manor at Maysville Golf Course View
Cozy, Bright Home in Historic Downtown
Classic kitchen with white cabinetry, green countertop, double sink, and refrigerator.

Cozy, Bright Home in Historic Downtown

9.0 out of 10, Wonderful, (16)
"We loved it you are in downtown it a nice place to stay"
The price is €118
includes taxes & fees
11 Aug - 12 Aug
Cozy, Bright Home in Historic Downtown
Historic Mt Lebanon, The Governor’s Estate
Stately building with a symmetrical facade, surrounded by a well-maintained lawn and mature trees.

Historic Mt Lebanon, The Governor’s Estate

9.6 out of 10, Exceptional, (20)
"What a treat that this place is available to us to rent. The property is gorgeous and so peaceful (until a freight train surprises you!). My family absolutely loved every moment and the history is fascinating. We especially admired the old books and bibles throughout the house. Anne Marie may be the most responsive host ever! I’d give more stars if I could. Highly recommend!"
Historic Mt Lebanon, The Governor’s Estate
Barn! 2-Hole Golf Course, BBall, Wiffleball, Soccer, Theater, Arcade, 2 Hot Tubs
Relax in style with a hot tub and scenic views.

Barn! 2-Hole Golf Course, BBall, Wiffleball, Soccer, Theater, Arcade, 2 Hot Tubs

2.0 star property
9.8 out of 10, Exceptional, (6)
"The Barn and the grounds were out of this world! We had a blast and highly recommend! "
Barn! 2-Hole Golf Course, BBall, Wiffleball, Soccer, Theater, Arcade, 2 Hot Tubs
Colliver House at Claybank Farm
Enjoy a peaceful retreat in this single-story home surrounded by a lush lawn and garden.

Colliver House at Claybank Farm

10.0 out of 10, Exceptional, (58)
"Very nice old farm house on a working horse farm. A mare an it’s foal (1 week old) spent most of their day in the field next to the house and loved to visit with us when we went up to the fence. Host was wonderful and the house had all the amenities one would ever need. "
Colliver House at Claybank Farm
The Winchester
Compact kitchen area with a central island, microwave, stove, and coffee maker for basic meal preparation.

The Winchester

9.4 out of 10, Exceptional, (3)
"I rented this house for my bridesmaids. It was a great location and house. The owner was accommodating and replied quickly "
The Winchester
Spacious Ewing Retreat w/ Game Room & Fireplace!
Kitchen equipped with microwave, coffee maker, and sink with a window above.

Spacious Ewing Retreat w/ Game Room & Fireplace!

10.0 out of 10, Exceptional, (1)
"This was a very large farmhouse, that accommodated our group very well. Lots of beds, and large kitchen area made cooking and dining very easy for a large group! Plus, we were so far out in the country, the kids could make all the noise they wanted! Mark, our host, was on sight to check us in and explained where everything was located. Plus, he provided a list in the kitchen area, of local emergency contact phone numbers, that was very helpful. Having two kitchens / refrigerators was nice, for a...
Spacious Ewing Retreat w/ Game Room & Fireplace!
Quiet Kentucky Vacation Rental w/ Fire Pit
Relax on a wicker sofa overlooking a lush landscape with a distant building.

Quiet Kentucky Vacation Rental w/ Fire Pit

10.0 out of 10, Exceptional, (28)
"Everything was very nice. Would highly recommend."
Quiet Kentucky Vacation Rental w/ Fire Pit
Horse Heaven! Pet friendly farm stay
Cozy living area with a large dining table and staircase leading to an upper level.

Horse Heaven! Pet friendly farm stay

9.6 out of 10, Exceptional, (14)
"Perfect for our family getaway to horse country. Kids loved the horses here."
Horse Heaven! Pet friendly farm stay
Ljbak1987@icloud.com
Cozy cabin-style interior with a high ceiling and exposed beams, featuring a round table and comfortable seating area.

Ljbak1987@icloud.com

10.0 out of 10, Exceptional, (2)
"This cabin was absolutely beautiful and perfect in every way! It had everything we could have possibly needed — from a thoughtfully stocked kitchen to body wash and soap in the bathrooms, which was such a nice touch. The kids’ area was a huge bonus and kept our little ones happy and entertained.The setting was just magical — the creek outside was peaceful and lovely, and we spent a lot of time just enjoying the relaxing atmosphere. We were in town for a family reunion, and this cabin made the...
Ljbak1987@icloud.com
Welcome Hall 5 bedroom 1880’s home on 55 acres
Surrounded by mature trees, this two-story home offers a peaceful living environment with a wrap-around porch and covered entrance.

Welcome Hall 5 bedroom 1880’s home on 55 acres

9.8 out of 10, Exceptional, (28)
"The kids didn't want to leave!"
Welcome Hall 5 bedroom 1880’s home on 55 acres
Georgetown Home Near Kentucky Horse Park!
Dining

Georgetown Home Near Kentucky Horse Park!

Georgetown Home Near Kentucky Horse Park!
Charming country home on 433 acres
Escape to a serene natural oasis with a fenced field and a cozy dog house.

Charming country home on 433 acres

10.0 out of 10, Exceptional, (2)
The price is €113
includes taxes & fees
10 Aug - 11 Aug
Charming country home on 433 acres
Peaceful, historic 3-bedroom barn loft on a horse and flower farm in Paris.
Enjoy meals with family and friends in this spacious dining area, complete with a wooden table and six matching chairs.

Peaceful, historic 3-bedroom barn loft on a horse and flower farm in Paris.

10.0 out of 10, Exceptional, (1)
"We absolutely loved staying here, such a great place and so relaxing! A great Kentucky experience for sure, staying in an actual stable!"
Peaceful, historic 3-bedroom barn loft on a horse and flower farm in Paris.
Hilltop Farmhouse with sunrise sunset porch overlooking hills and holler
Stunning garden area with a large tree surrounded by vibrant flowers and natural borders.

Hilltop Farmhouse with sunrise sunset porch overlooking hills and holler

10.0 out of 10, Exceptional, (27)
"Everything was just as described? Had a great stay!"
Hilltop Farmhouse with sunrise sunset porch overlooking hills and holler
Furnished dormer room neighboring the Maysville Country Club.
Terrace/patio

Furnished dormer room neighboring the Maysville Country Club.

Furnished dormer room neighboring the Maysville Country Club.
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 Carlisle Hotel Reviews

Holiday Inn Express Lexington East - Winchester by IHG

Holiday Inn Express Lexington East - Winchester by IHG

10/10 Excellent
"The hotel was very nice and check-in staff were great. Overall, the hotel was very quiet. Great, free breakfast with lots of food options. Convenient parking and right off the interstate. There's even a movie theatre across the street if you want something to do!"
Brian 1-night trip
Posted 23 hours ago
Holiday Inn Express Lexington East - Winchester by IHG