Book Holiday Homes in Jackson

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Featured Holiday Homes in Jackson

Kentucky's Majestic Mountaintop Estate: The Bluegrass Palace

Kentucky's Majestic Mountaintop Estate: The Bluegrass Palace

Langley
Located in Langley, this vacation home is in the mountains, within a 15-minute drive of ARH Our Lady of the Way and McDowell ARH Hospital.
Kentucky's Majestic Mountaintop Estate: The Bluegrass Palace
Whistling Wind Cabin Unit 3 in RRG

Whistling Wind Cabin Unit 3 in RRG

Pine Ridge
With a stay at this vacation home in Pine Ridge, you'll be within a 15-minute drive of Natural Bridge State Park and Daniel Boone National Forest.
Whistling Wind Cabin Unit 3 in RRG
Robin's Nest luxury cabin, Red River Gorge

Robin's Nest luxury cabin, Red River Gorge

Slade
When you a stay at this vacation home in Slade, you'll be in the mountains, within a 5-minute walk of Daniel Boone National Forest and Kentucky Reptile Zoo.
Robin's Nest luxury cabin, Red River Gorge
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Looking Glass | 3 Bed, 1 Bath

Looking Glass | 3 Bed, 1 Bath

Campton
The price is AU$687 per night from 25 Dec to 26 Dec
AU$687
includes taxes & fees
25 Dec - 26 Dec
With a stay at this vacation home in Rogers, you'll be steps from Daniel Boone National Forest and a 4-minute drive from Natural Bridge State Park.
Looking Glass | 3 Bed, 1 Bath
Small Town Charmer - Rent Entire Home

Small Town Charmer - Rent Entire Home

Hazard
A stay at this vacation home places you in the heart of Hazard, within a 5-minute drive of Bobby Davis Museum and Hazard Community & Technical College.
Small Town Charmer - Rent Entire Home
'Grandma's Farm House' on 125 Acres w/ Fire Pit!

'Grandma's Farm House' on 125 Acres w/ Fire Pit!

Beattyville
When you stay at this vacation home in Beattyville, you'll be 5 minutes by car from Daniel Boone National Forest.
'Grandma's Farm House' on 125 Acres w/ Fire Pit!
Cozy Home in Heart of Prestonsburg

Cozy Home in Heart of Prestonsburg

Prestonsburg
The price is AU$311 per night from 1 Jan to 2 Jan
AU$311
includes taxes & fees
1 Jan - 2 Jan 2025
A stay at this vacation home places you in the heart of Prestonsburg, within a 5-minute drive of Samuel May House and Archer Park.
Cozy Home in Heart of Prestonsburg
Hot-Tub/WiFi /Secluded - A Red River Barnhouse

Hot-Tub/WiFi /Secluded - A Red River Barnhouse

Campton
The price is AU$648 per night from 1 Jan to 2 Jan
AU$648
includes taxes & fees
1 Jan - 2 Jan 2025
When you stay at this vacation home in Campton, you'll be in the mountains and within a 5-minute drive of Daniel Boone National Forest.
Hot-Tub/WiFi /Secluded - A Red River Barnhouse
Hillside Hideaway! NEW hot tub! Family sized loft cabin, RRG, Pets welcome.

Hillside Hideaway! NEW hot tub! Family sized loft cabin, RRG, Pets welcome.

Campton
Located in Campton, this vacation home is in the mountains, a 1-minute drive from Daniel Boone National Forest and 7 minutes from Red River Gorge Geological ...
Hillside Hideaway! NEW hot tub! Family sized loft cabin, RRG, Pets welcome.
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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.

Jackson Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Jackson vacation homes are the perfect way for you to wing it.

Holiday houses in Jackson let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Jackson in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Jackson adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Jackson with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Jackson vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Jackson Holiday Homes essential information

Accommodation
70 Holiday Homes
Lowest Price
AU$152
Highest Price
AU$687
Popular accommodation
Kentucky's Majestic Mountaintop Estate: The Bluegrass Palace, Whistling Wind Cabin Unit 3 in RRG, Robin's Nest luxury cabin, Red River Gorge, Looking Glass | 3 Bed, 1 Bath, Small Town Charmer - Rent Entire Home, 'Grandma's Farm House' on 125 Acres w/ Fire Pit!, Cozy Home in Heart of Prestonsburg, Hot-Tub/WiFi /Secluded - A Red River Barnhouse, Hillside Hideaway! NEW hot tub! Family sized loft cabin, RRG, Pets welcome.

Top trending hotels in Jackson

Secluded with best views in E. KY. Can see 3 states.You won’t be disappointed!!!

Secluded with best views in E. KY. Can see 3 states.You won’t be disappointed!!!

Jackson
When you stay at this cabin in Jackson, you'll be in the mountains and 13 minutes by car from Kentucky River Medical Center.
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

Secluded with amazing view from hot tub.Gated mountain top.Won’t be disappointed

Jackson
When you stay at this cabin in Jackson, you'll be in the mountains and 13 minutes by car from Kentucky River Medical Center.
Secluded with amazing view from hot tub.Gated mountain top.Won’t be disappointed
Natural Bridge State Resort Park

Natural Bridge State Resort Park

3.5 out of 5
2135 Natural Bridge Road, Slade, KY
Fully refundableReserve now, pay when you stay
The price is AU$152 per night from 6 Jan to 7 Jan
AU$152
includes taxes & fees
6 Jan - 7 Jan 2025
When you a stay at Natural Bridge State Resort Park in Slade, you'll be in a state park, just steps from Natural Bridge State Park and Daniel Boone National ...
Natural Bridge State Resort Park
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Black Bear Lodge Motel

Black Bear Lodge Motel

2.5 out of 5
781 Natural Bridge Rd, Slade, KY
The price is AU$159 per night from 25 Dec to 26 Dec
AU$159
includes taxes & fees
25 Dec - 26 Dec
When you a stay at Black Bear Lodge Motel in Slade, you'll be in the mountains, just steps from Natural Bridge State Park and Daniel Boone National Forest.
Black Bear Lodge Motel
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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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^Subject to availability and chosen travel dates.