Jackson Holiday Rentals
Cabin
- Kentucky
- ·
- Pine Ridge
- 0.85 mi to center
10.0Exceptional
(144 Reviews)
1 Bedroom
1 Bath
3 Guests
Parking
Balcony/Terrace
Kitchen
Air Conditioner
US $148/Night
7 Nights - US $1,038
Villa
10.0Exceptional
(7 Reviews)
3 Bedrooms
2 Baths
8 Guests
10763.91 ft²
Hot Tub- Parking
Pet Friendly
Child Friendly
US $375/Night
7 Nights - US $2,623
Cottage
10.0Exceptional
(8 Reviews)
1 Bedroom
1 Bath
- Parking
- Kitchen
- Air Conditioner
Internet
US $299/Night
7 Nights - US $2,095
Cabin
10.0Exceptional
(75 Reviews)
2 Bedrooms
1 Bath
6 Guests
900 ft²
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $343/Night
7 Nights - US $2,404
House
- Kentucky
- ·
- Heidelberg
- 0.45 mi to center
10.0Exceptional
(7 Reviews)
1 Bedroom
1 Bath
6 Guests
548.96 ft²
- Hot Tub
- Parking
- Balcony/Terrace
View
US $234/Night
7 Nights - US $1,635
Cabin
10.0Exceptional
(58 Reviews)
1 Bedroom
1 Bath
4 Guests
- Hot Tub
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $350/Night
7 Nights - US $2,453
Cabin
10.0Exceptional
(48 Reviews)
1 Bedroom
1 Bath
6 Guests
900 ft²
- Hot Tub
- Parking
- Kitchen
- Air Conditioner
US $310/Night
7 Nights - US $2,172
House
10.0Exceptional
(45 Reviews)
2 Bedrooms
1 Bath
4 Guests
1200 ft²
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $281/Night
7 Nights - US $1,970
Cabin
10.0Exceptional
(44 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
US $406/Night
7 Nights - US $2,840
Luxury Holiday Rentals in Jackson
Over 1114+ Luxury Holiday Rentals in or Near Jackson
House
9.8Exceptional
(21 Reviews)
12 Bedrooms
12 Baths
40 Guests
Private Pool- Hot Tub
- Parking
Pool
US $1,910/Night
7 Nights - US $13,368
House
12 Bedrooms
15 Baths
40 Guests
29999.02 ft²
- Private Pool
- Hot Tub
- Parking
- Pool
US $1,707/Night
7 Nights - US $11,947
New
House
4 Bedrooms
2 Baths
14 Guests
6565.99 ft²
- Hot Tub
- View
- Internet
- Pet Friendly
US $1,351/Night
7 Nights - US $9,459
Cabin
10.0Exceptional
(3 Reviews)
12 Bedrooms
9 Baths
30 Guests
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $1,247/Night
7 Nights - US $8,727
House
10.0Exceptional
(1 Review)
5 Bedrooms
5 Baths
14 Guests
4994 ft²
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $1,156/Night
7 Nights - US $8,093
House
5 Bedrooms
5 Baths
14 Guests
4994.45 ft²
- Hot Tub
- View
- Air Conditioner
- Internet
US $1,097/Night
7 Nights - US $7,679
New
House
6 Bedrooms
4 Baths
12 Guests
- Air Conditioner
- Internet
- Child Friendly
Laundry
US $911/Night
7 Nights - US $6,380
House
10.0Exceptional
(3 Reviews)
1 Bedroom
1 Bath
2 Guests
226.04 ft²
- Hot Tub
- Parking
- Balcony/Terrace
- Air Conditioner
US $870/Night
7 Nights - US $6,092
House
- Kentucky
- ·
- Pine Ridge
- 0.47 mi to center
10.0Exceptional
(5 Reviews)
5 Bedrooms
4 Baths
17 Guests
2200 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $868/Night
7 Nights - US $6,077
Top-Rated Holiday Rentals with a Pool in Jackson
Over 22+ The Best Private Villas and Holiday Rentals in Jackson with a Pool
New
Cabin
10.0Exceptional
(7 Reviews)
1 Bedroom
1 Bath
4 Guests
700 ft²
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
US $262/Night
7 Nights - US $1,832
Cabin
9.6Exceptional
(75 Reviews)
1 Bedroom
1 Bath
4 Guests
- Hot Tub
- Pool
- Balcony/Terrace
- Kitchen
US $243/Night
7 Nights - US $1,698
Hotel
- Hazard
- ·
- Gays Creek
- 1.89 mi to center
9.0Exceptional
(219 Reviews)
1 Bath
Breakfast- Parking
- Pool
- Balcony/Terrace
US $128/Night
7 Nights - US $899
Cabin
9.0Exceptional
(41 Reviews)
2 Bedrooms
2 Baths
9 Guests
- Private Pool
- Hot Tub
- Pool
- Balcony/Terrace
US $380/Night
7 Nights - US $2,660
Cabin
8.6Fabulous
(1943 Reviews)
1 Bedroom
1 Bath
- Breakfast
- Parking
- Pool
- Balcony/Terrace
US $155/Night
7 Nights - US $1,088
Hotel
- Kentucky
- ·
- Prestonsburg
- 1.44 mi to center
8.6Fabulous
(748 Reviews)
1 Bath
- Breakfast
- Parking
- Pool
- Kitchen
US $124/Night
7 Nights - US $871
Hotel
7.8Very Good
(423 Reviews)
1 Bath
- Breakfast
- Parking
- Pool
- Balcony/Terrace
US $102/Night
7 Nights - US $713
Hotel
6.6Good
(131 Reviews)
8 Baths
330.61 ft²
- Private Pool
Oceanfront- Parking
- Pool
US $131/Night
7 Nights - US $915
House
4 Bedrooms
5 Baths
14 Guests
462.85 ft²
- Hot Tub
- Pool
- View
- Air Conditioner
US $862/Night
7 Nights - US $6,032
Pet-Friendly Holiday Rentals in Jackson
Over 567+ Pet-Friendly Holiday Rentals in or Near Jackson
Cabin
- Pine Ridge
- ·
- Rogers
- 0.36 mi to center
10.0Exceptional
(36 Reviews)
2 Bedrooms
1 Bath
4 Guests
398 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $249/Night
7 Nights - US $1,742
House
10.0Exceptional
(7 Reviews)
2 Bedrooms
1 Bath
6 Guests
1302.43 ft²
- Parking
- Pet Friendly
- Child Friendly
Sports/Activities
US $165/Night
7 Nights - US $1,155
Cabin
- Kentucky
- ·
- Beattyville
- 1.64 mi to center
10.0Exceptional
(7 Reviews)
1 Bedroom
1 Bath
- Parking
- Balcony/Terrace
- Internet
- Pet Friendly
US $296/Night
7 Nights - US $2,073
Cabin
- Pine Ridge
- ·
- Rogers
- 0.36 mi to center
10.0Exceptional
(34 Reviews)
2 Bedrooms
2 Baths
4 Guests
958 ft²
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $405/Night
7 Nights - US $2,836
House
- Kentucky
- ·
- Heidelberg
- 4.83 mi to center
10.0Exceptional
(7 Reviews)
3 Bedrooms
1 Bath
6 Guests
1054.86 ft²
- Parking
- Internet
- Pet Friendly
- Child Friendly
US $159/Night
7 Nights - US $1,111
Cabin
10.0Exceptional
(31 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $228/Night
7 Nights - US $1,596
Cabin
- Kentucky
- ·
- Pine Ridge
- 2.36 mi to center
10.0Exceptional
(27 Reviews)
1 Bedroom
1 Bath
2 Guests
- Hot Tub
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $384/Night
7 Nights - US $2,685
Cabin
10.0Exceptional
(26 Reviews)
1 Bedroom
1 Bath
2 Guests
- Kitchen
- Air Conditioner
- Internet
- Pet Friendly
US $317/Night
7 Nights - US $2,217
Cabin
10.0Exceptional
(25 Reviews)
2 Bedrooms
1 Bath
7 Guests
- Hot Tub
- Kitchen
- Air Conditioner
- Internet
US $331/Night
7 Nights - US $2,315
Large Holiday Rentals and Private Villas in Jackson
Over 120+ Large Holiday Rentals and Private Villas in or Near Jackson
Cabin
10.0Exceptional
(187 Reviews)
4 Bedrooms
4 Baths
14 Guests
2200 ft²
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $553/Night
7 Nights - US $3,874
House
10.0Exceptional
(3 Reviews)
4 Bedrooms
3 Baths
14 Guests
2002.09 ft²
- Hot Tub
- Parking
- Balcony/Terrace
- Internet
US $342/Night
7 Nights - US $2,392
Cabin
4 Bedrooms
2 Baths
12 Guests
1750 ft²
US $348/Night
7 Nights - US $2,433
Cabin
10.0Exceptional
(25 Reviews)
4 Bedrooms
3 Baths
12 Guests
1600 ft²
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $474/Night
7 Nights - US $3,315
Villa
10.0Exceptional
(2 Reviews)
3 Bedrooms
2 Baths
8 Guests
1302.43 ft²
EV Charge Station- Parking
- View
- Air Conditioner
US $393/Night
7 Nights - US $2,754
Cabin
10.0Exceptional
(19 Reviews)
5 Bedrooms
4 Baths
15 Guests
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $603/Night
7 Nights - US $4,221
House
10.0Exceptional
(19 Reviews)
5 Bedrooms
3 Baths
12 Guests
3000 ft²
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $526/Night
7 Nights - US $3,685
Cabin
10.0Exceptional
(13 Reviews)
4 Bedrooms
3 Baths
10 Guests
2300 ft²
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $529/Night
7 Nights - US $3,704
Cabin
10.0Exceptional
(10 Reviews)
4 Bedrooms
3 Baths
12 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $561/Night
7 Nights - US $3,928
Wheelchair Accessible Holiday Homes in Jackson
Over 20+ Wheelchair Accessible Holiday Homes in or Near Jackson
Apartment
- Kentucky
- ·
- Pine Ridge
- 0.36 mi to center
9.6Exceptional
(59 Reviews)
1 Bedroom
1 Bath
4 Guests
850 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $205/Night
7 Nights - US $1,434
New
Hotel
- Kentucky
- ·
- Prestonsburg
- 1.01 mi to center
10.0Exceptional
(3 Reviews)
6 Baths
301.39 ft²
- Parking
- Air Conditioner
- Internet
- Pet Friendly
US $104/Night
7 Nights - US $728
Hotel
- Kentucky
- ·
- Prestonsburg
- 1.35 mi to center
8.0Excellent
(397 Reviews)
1 Bath
- Breakfast
- Parking
- Balcony/Terrace
- Kitchen
US $116/Night
7 Nights - US $810
Cabin
9.4Exceptional
(288 Reviews)
1 Bedroom
1 Bath
4 Guests
600 ft²
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $171/Night
7 Nights - US $1,196
Hotel
- Kentucky
- ·
- Prestonsburg
- 1.35 mi to center
8.6Fabulous
(223 Reviews)
3 Baths
215.28 ft²
- Parking
- Kitchen
- Air Conditioner
- Internet
US $117/Night
7 Nights - US $821
Cabin
8.6Fabulous
(22 Reviews)
1 Bedroom
1 Bath
6 Guests
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
US $181/Night
7 Nights - US $1,267
Cabin
9.0Exceptional
(40 Reviews)
3 Bedrooms
1 Bath
6 Guests
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $323/Night
7 Nights - US $2,258
Cabin
8.2Excellent
(47 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Hot Tub
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $232/Night
7 Nights - US $1,626
Cabin
8.0Excellent
(39 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Hot Tub
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $235/Night
7 Nights - US $1,647
Jackson Private Villas and Holiday Homes Under $200
Over 312+ Jackson Private Villas and Holiday Homes Under $200
Cottage
10.0Exceptional
(35 Reviews)
2 Bedrooms
1 Bath
4 Guests
1000 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $162/Night
7 Nights - US $1,136
House
10.0Exceptional
(7 Reviews)
2 Bedrooms
2 Baths
6 Guests
1097.92 ft²
- Hot Tub
- Parking
- Balcony/Terrace
- Air Conditioner
US $149/Night
7 Nights - US $1,042
RV Rental
- Kentucky
- ·
- Heidelberg
- 4.04 mi to center
9.2Exceptional
(113 Reviews)
1 Bedroom
1 Bath
- Breakfast
- Parking
- Balcony/Terrace
- View
US $120/Night
7 Nights - US $840
Cabin
10.0Exceptional
(17 Reviews)
1 Bedroom
1 Bath
2 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $168/Night
7 Nights - US $1,176
House
- Kentucky
- ·
- Beattyville
- 1.54 mi to center
10.0Exceptional
(5 Reviews)
2 Bedrooms
1 Bath
4 Guests
581.25 ft²
- Parking
- Balcony/Terrace
- Internet
- Child Friendly
US $160/Night
7 Nights - US $1,120
Cabin
10.0Exceptional
(15 Reviews)
2 Bedrooms
1 Bath
4 Guests
560 ft²
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $185/Night
7 Nights - US $1,298
House
- Kentucky
- ·
- Pine Ridge
- 1.53 mi to center
10.0Exceptional
(4 Reviews)
2 Bedrooms
1 Bath
6 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $123/Night
7 Nights - US $864
Cabin
10.0Exceptional
(1 Review)
1 Bedroom
1 Bath
2 Guests
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $188/Night
7 Nights - US $1,313
Cabin
- Kentucky
- ·
- Pine Ridge
- 0.85 mi to center
9.8Exceptional
(113 Reviews)
2 Bedrooms
1 Bath
5 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $185/Night
7 Nights - US $1,298
Instantly Bookable Holiday Homes in Jackson
Over 736+ Instantly Bookable Holiday Homes in or Near Jackson
House
10.0Exceptional
(26 Reviews)
2 Bedrooms
1 Bath
4 Guests
1200 ft²
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $278/Night
7 Nights - US $1,946
Apartment
- Kentucky
- ·
- Pine Ridge
- 0.52 mi to center
9.6Exceptional
(99 Reviews)
1 Bedroom
1 Bath
4 Guests
700 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $268/Night
7 Nights - US $1,875
Cabin
10.0Exceptional
(24 Reviews)
2 Bedrooms
2 Baths
8 Guests
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $333/Night
7 Nights - US $2,331
Cabin
- Pine Ridge
- ·
- Rogers
- 1.31 mi to center
10.0Exceptional
(21 Reviews)
1 Bedroom
1 Bath
2 Guests
1000 ft²
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $355/Night
7 Nights - US $2,488
Cabin
10.0Exceptional
(20 Reviews)
2 Bedrooms
1 Bath
6 Guests
10764 ft²
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $305/Night
7 Nights - US $2,136
Cabin
- Pine Ridge
- ·
- Rogers
- 0.95 mi to center
10.0Exceptional
(19 Reviews)
2 Bedrooms
2 Baths
7 Guests
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $329/Night
7 Nights - US $2,303
Cabin
10.0Exceptional
(17 Reviews)
1 Bedroom
1 Bath
2 Guests
- Hot Tub
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $526/Night
7 Nights - US $3,683
Cabin
10.0Exceptional
(16 Reviews)
2 Bedrooms
1 Bath
4 Guests
398 ft²
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $403/Night
7 Nights - US $2,822
Cabin
10.0Exceptional
(16 Reviews)
1 Bedroom
1 Bath
2 Guests
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
US $319/Night
7 Nights - US $2,231
Book a Last Minute Place to Stay in Jackson
About Casai's Private Villas and Holiday Rentals in Jackson
Discover more than 1123 vacation rentals available in Jackson. These rentals, ranging from vacation rentals to Casai Homes and other short-term private accommodations, offer top-notch amenities with unbeatable value, ensuring both comfort and luxury. Enjoy more space and value when you stay at a Casai property in Jackson.
Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Jackson, you can effortlessly compare various deals with just a click. Whether you're looking for a Casai with exceptional swimming pools, hot tubs, pet-friendly options, or large master suite bedrooms equipped with large screen televisions, you'll find a variety of options near Jackson. On average, places to stay near Jackson offer 910.12 ft², with nightly prices averaging US $301.
With Casai, finding and comparing holiday rentals in Jackson is easy and secure, often at a 30-40% discount compared to hotel prices. Simply search for your destination and secure your reservation today.
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Top Accommodation Types in Jackson
| Type | Count |
|---|---|
| Vacation Homes | 376 |
| Holiday Apartments | 36 |
| Cottages | 18 |
| Villas | 2 |
Use these Quick Filters to Find a Holiday Rental in Jackson
★ Pro Tip: Casai simplifies the process of comparing the finest listings across various online vacation rental platforms, including Booking.com and more. Utilize the Advanced Filter feature located at the top to effortlessly switch between Casai homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals, eco-friendly properties, and different property types. Explore various cancellation policies, prices, and numerous options to find the ideal accommodation for your next vacation in Jackson.
Weather in Jackson, KY
View the weather forecast for Jackson before booking your Jackson Vacation Rentals to confirm your best time to go.
December - February
High 60°F Low 26°F
March - May
High 77°F Low 40°F
June - August
High 91°F Low 64°F
September - November
High 84°F Low 38°F
Top Attractions Around Jackson, KY
Casai offers a large selection of top attractions around Jackson . Research things to do on your vacation before you visit Jackson.
Other Places to Stay in Jackson, KY
Frequently Asked Questions About Jackson?
What are the top holiday rentals in Jackson?
With numerous options available in Jackson, planning to stay in the area? Consider booking a few nights at one of these properties, rated as the Top Holiday Rentals in Jackson:
- Secluded with best views in E. KY. Can see 3 states.You won’t be disappointed!
- Secluded with amazing view from hot tub.Gated mountain top.Won’t be disappointed
- Your search ends with KSW Cabin. All a group needs, incl. 5 bathrooms. Sleeps 14
- Sleepy Bear: Luxe cabin, private lake, hottub, caves, fast WiFi @ BearTrackLake
- TURNING LEAF Cozy Cabin in the RRG Couples Retreat
- Hike & Zip-Line: Red River Gorge Cabin w/Hot Tub!
- Sneaky Bear: Luxe lakeview cabin, caves, trails, fast WiFi @ BearTrackLake
- 6 BR 3 bath Elegant farmhouse
- 'Grandma's Farm House' on 125 Acres w/Fire Pit!
- Trailseeker Cabin King Bed, WiFi, Hot Tub at Red River Gorge - Natural Bridge
How many holiday rentals have private pools in Jackson?
Discover a selection of holiday rentals with private pools near Jackson with Casai. Experience the epitome of luxury and relaxation in our top-rated villas and holiday homes, where you can enjoy exclusive access to refreshing swimming pools.
Which holiday homes in Jackson are best for families?
If you're searching for a family-friendly holiday home in Jackson, consider one of the following properties. Each comes highly recommended, with excellent reviews for families or groups staying in Jackson:
- Red River Gorge Turtle Falls Hot Tub Firepit Wi-Fi
- S'more Memories-Cold Plunge, Sauna, Hot Tub Wellness Retreat
- Campton 3040 KY-11
How many Casai.nz holiday rentals are available in Jackson?
As of 2026, Casai boasts over 1123 properties listed in the Jackson area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Jackson.
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