Carlisle Holiday Rentals

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Check prices for these dates

In two weeks
5 Sept - 7 Sept
In two months
17 Oct - 19 Oct
In three months
14 Nov - 16 Nov
In four months
12 Dec - 14 Dec

Holiday Rentals in Carlisle

Hilltop Farmhouse with sunrise sunset porch overlooking hills and holler
Exterior detail

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
Tiny Cabin - A Frame of Mind - near Red River Gorge Kentucky!
Exterior

Tiny Cabin - A Frame of Mind - near Red River Gorge Kentucky!

9.2 out of 10, Wonderful, (67)
"The cabin was very clean and comfortable!! It was in a very quiet setting. Perfect place to rest and unwind! "
The price is HK$760
HK$1,440 total
includes taxes & fees
25 Aug - 26 Aug
Tiny Cabin - A Frame of Mind - near Red River Gorge Kentucky!
4 Bed 3 bath clean , spacious all brick home , welcome families and work groups
Fridge, microwave, oven, stovetop

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

10.0 out of 10, Exceptional, (5)
"We came into town for a work event in Lexington and Wayne was an outstanding host. Beautiful home with plenty of bedrooms to sleep a big group. Wayne was very accommodating and checked in with us throughout the stay. They made sure to provide extra towels/linens/garbage bags knowing we had a large group! I would absolutely recommend this home if you are looking in this area!"
4 Bed 3 bath clean , spacious all brick home , welcome families and work groups
Peaceful, historic 3-bedroom barn loft on a horse and flower farm in Paris.
Dining

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.
Cabin on 80 acre farm with donkeys, cows and goats
Microwave, oven, stovetop, coffee/tea maker

Cabin on 80 acre farm with donkeys, cows and goats

10.0 out of 10, Exceptional, (114)
"Amazing stay, highly recommend "
The price is HK$879
HK$1,552 total
includes taxes & fees
24 Aug - 25 Aug
Cabin on 80 acre farm with donkeys, cows and goats
Spacious 4-bedroom 19th Century home in historic downtown Maysville!
Fridge, microwave, oven, stovetop

Spacious 4-bedroom 19th Century home in historic downtown Maysville!

10.0 out of 10, Exceptional, (2)
"We were overly impressed by this property and the location. The house was emasculate and had such great character in every room. Check in and communication with the property own were top notch. The main areas in the town are all within short walking distance of the home. We will definitely look for this home again next year when we come back to Maysville. We won Oktoberfest king 2025 so we’ll definitely be back!"
Spacious 4-bedroom 19th Century home in historic downtown Maysville!
Beautiful Country Sunsets I
Interior

Beautiful Country Sunsets I

9.8 out of 10, Exceptional, (65)
"Relaxing, beautiful view, feeding the horses and listening to bull frog..."
The price is HK$664
HK$1,129 total
includes taxes & fees
26 Aug - 27 Aug
Beautiful Country Sunsets I
Barn! 2-Hole Golf Course, BBall, Wiffleball, Soccer, Theater, Arcade, 2 Hot Tubs
Terrace/patio

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
The Winchester
Fridge, microwave, oven, stovetop

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
Quiet Kentucky Vacation Rental w/ Fire Pit
Interior

Quiet Kentucky Vacation Rental w/ Fire Pit

3.0 star property
10.0 out of 10, Exceptional, (1)
"Amazing and relaxing stay! Place was beautiful, clean, and peaceful. Bunnies and horses greeted us as we arrived and throughout our stay. Keyless entry was convenient and owner was communicative and friendly. Even though I would recommend this place, I would say one downside is the location of the property. I have motion sickness and the drive to and from the location included lots of windy back roads for 20+ minutes which made me sick. Additionally, the closest convenience store is 15...
Quiet Kentucky Vacation Rental w/ Fire Pit
Sprawling Kentucky Getaway w/ Pool & Hot Tub!
Fridge, microwave, stovetop, dishwasher

Sprawling Kentucky Getaway w/ Pool & Hot Tub!

2.0 star property
9.8 out of 10, Exceptional, (8)
"Enjoyed it"
Sprawling Kentucky Getaway w/ Pool & Hot Tub!
The Manor at Maysville Golf Course View
Smart TV, fireplace, stereo, computer monitors

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
Colliver House at Claybank Farm
Exterior

Colliver House at Claybank Farm

10.0 out of 10, Exceptional, (58)
"Wonderful place to stay!"
Colliver House at Claybank Farm
Cozy Sunset Cottage on the family farm near Cave Run Lake and Morehead State
Fridge, microwave, oven, stovetop

Cozy Sunset Cottage on the family farm near Cave Run Lake and Morehead State

10.0 out of 10, Exceptional, (30)
"I loved everything about this place. Peaceful and quiet. I definitely want to come back and stay longer. "
The price is HK$938
HK$1,506 total
includes taxes & fees
3 Sept - 4 Sept
Cozy Sunset Cottage on the family farm near Cave Run Lake and Morehead State
Private Country Estate: 16 miles to Keeneland, 13 to KY Horse Park!
Dining

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!
Charming 2-bedroom Tiny House with WiFi, AC in relaxing Brooksville
Exterior

Charming 2-bedroom Tiny House with WiFi, AC in relaxing Brooksville

10.0 out of 10, Exceptional, (1)
Charming 2-bedroom Tiny House with WiFi, AC in relaxing Brooksville
In the Heart of Historic Downtown Paris KY
Terrace/patio

In the Heart of Historic Downtown Paris KY

9.8 out of 10, Exceptional, (15)
"The property was right on the main drag of the quaint town of Paris. It was charming, quiet, and a short beautiful drive away from Lexington. I highly recommend staying here if you're in the area."
In the Heart of Historic Downtown Paris KY
Charming & Inviting Apartment in Historic Downtown Paris, Ky.
Exterior detail

Charming & Inviting Apartment in Historic Downtown Paris, Ky.

9.8 out of 10, Exceptional, (112)
"Property is spacious and period architecture. Road noise can be a bit much unless you are an early riser. Very close to Secretariat park (walking) and Claiborne farms. Easy drive to Kentucky Horse Park. Upstairs above business on the Main Street of Paris. Enjoyed the space and location. "
Charming & Inviting Apartment in Historic Downtown Paris, Ky.
Beautiful country sunsets II
Exterior

Beautiful country sunsets II

10.0 out of 10, Exceptional, (30)
"Cozy. Clean and had everything we needed"
Beautiful country sunsets II
Large Downtown Artist's Loft, 30 min to Lexington, Horse, Bourbon, R River Gorge
Microwave, dishwasher, coffee/tea maker, cookware/dishes/utensils

Large Downtown Artist's Loft, 30 min to Lexington, Horse, Bourbon, R River Gorge

9.8 out of 10, Exceptional, (6)
"Stayed on business. Everything you need and great area"
Large Downtown Artist's Loft, 30 min to Lexington, Horse, Bourbon, R River Gorge
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

Comfort Inn and Suites

Comfort Inn and Suites

10/10 Excellent
"It was clean"
Tyler 1-night trip
Posted 2 days ago
Comfort Inn and Suites

Frequently asked questions

Are there holiday rentals in Carlisle?

Yes, there are holiday rentals close to the most popular sights in Carlisle, or you can select a more secluded option if you're looking for a relaxing stay. Carlisle is known for its forests and restaurants.

What are some of the best holiday rentals that Carlisle has to offer?

Spacious 4-bedroom 19th Century home in historic downtown Maysville!: This holiday home rental outside of Carlisle is located on a river, and offers a patio, air conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

What can I see and do in Carlisle?

While you're exploring the area, Lake Carnico and Bourbon County Park are a couple of picturesque spots to get outside and enjoy nature. In the wider area, you’ll find Blue Licks Battlefield State Park and The Cane Ridge Meeting House.

What are holiday rentals like in Carlisle?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Carlisle. Holiday rentals offer extras like kitchens and laundry facilities so you'll be comfy for your stay. If you're concerned about cleanliness, holiday rentals can offer a sense of safety away from public hotel lifts and busy lobbies while still allowing you the excitement and enjoyment of travel. You'll also find more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a great choice for a family trip.