Book Holiday Homes in Wellington

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Featured Holiday Homes in Wellington

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

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

2 out of 5
Mount Sterling KY
Located in Mount Sterling, this vacation home is within a 15-minute drive of Mount Sterling Library and CHI Saint Joseph Health - Saint Joseph Mount ...
Opens in a new windowBarn! 2-Hole Golf Course, BBall, Wiffleball, Soccer, Theater, Arcade, 2 Hot Tubs
Overlook Oasis! RRG, A-frame Cabin, NEW HOT TUB, Grill! Pet friendly

Overlook Oasis! RRG, A-frame Cabin, NEW HOT TUB, Grill! Pet friendly

Campton, KY
The price is AU$454 per night from 16 Dec to 17 Dec
AU$454
16 Dec - 17 Dec
includes taxes & fees
Located in Campton, this vacation home is in a rural location, within a 15-minute drive of Red River Gorge Geological Area and Muir Valley.
Opens in a new windowOverlook Oasis! RRG, A-frame Cabin, NEW HOT TUB, Grill! Pet friendly
Hot Tub! Fire pit! Picnic area & Grill! Dog friendly Hardwicks Creek Haven@RRG

Hot Tub! Fire pit! Picnic area & Grill! Dog friendly Hardwicks Creek Haven@RRG

Clay City KY
The price is AU$402 per night from 4 Jan to 5 Jan
AU$402
4 Jan - 5 Jan 2026
includes taxes & fees
With a stay at this vacation home in Clay City, you'll be 15.6 mi (25.1 km) from Mercy Health - Marcum and Wallace Hospital and 15.9 mi (25.5 km) from Veterans ...
Opens in a new windowHot Tub! Fire pit! Picnic area & Grill! Dog friendly Hardwicks Creek Haven@RRG
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Sugarloaf Mountain Escape
Secluded 3 bedroom, 5 acres, ATV, RV and boat storage.

Sugarloaf Mountain Escape Secluded 3 bedroom, 5 acres, ATV, RV and boat storage.

Morehead KY
When you stay at this vacation home in Morehead, you'll be in the mountains and 13 minutes by car from Zane Collins Community Park.
Opens in a new windowSugarloaf Mountain Escape Secluded 3 bedroom, 5 acres, ATV, RV and boat storage.
Tiny Home in the Heart of Red River Gorge

Tiny Home in the Heart of Red River Gorge

2 out of 5
Stanton KY
Located in Stanton, this vacation home is within a 10-minute drive of Kentucky Reptile Zoo and Osborne Bend Trail.
Opens in a new windowTiny Home in the Heart of Red River Gorge
Red River Duplex - Unit 5 - 12 miles to the Gorge!

Red River Duplex - Unit 5 - 12 miles to the Gorge!

Stanton KY
Located in Stanton, this vacation home is within a 15-minute drive of Kentucky Reptile Zoo and Osborne Bend Trail.
Opens in a new windowRed River Duplex - Unit 5 - 12 miles to the Gorge!
New Barndominium /Sleeps 24/ 4 Kitchens / 4 Hot Tubs / 4 Firepits

New Barndominium /Sleeps 24/ 4 Kitchens / 4 Hot Tubs / 4 Firepits

Stanton KY
The price is AU$1,702 per night from 16 Dec to 17 Dec
AU$1,702
16 Dec - 17 Dec
includes taxes & fees
Located in Stanton, this vacation home is within a 15-minute drive of Kentucky Reptile Zoo and Natural Bridge State Park.
Opens in a new windowNew Barndominium /Sleeps 24/ 4 Kitchens / 4 Hot Tubs / 4 Firepits
Treetop Escape | Hot Tub | Fire Pit & Epic Views

Treetop Escape | Hot Tub | Fire Pit & Epic Views

Rogers KY
The price is AU$414 per night from 16 Dec to 17 Dec
AU$414
16 Dec - 17 Dec
includes taxes & fees
Located in Rogers, this vacation home is in the mountains, within a 15-minute drive of Graining Fork Nature Preserve and Ashland Wildlife Management Area.
Opens in a new windowTreetop Escape | Hot Tub | Fire Pit & Epic Views
Kim's Retreat: 3-BR Cabin w/ Hot Tub near Natural Bridge & Red River Gorge

Kim's Retreat: 3-BR Cabin w/ Hot Tub near Natural Bridge & Red River Gorge

Stanton KY
The price is AU$395 per night from 16 Dec to 17 Dec
AU$395
16 Dec - 17 Dec
includes taxes & fees
With a stay at this vacation home in Stanton, you'll be 7.7 mi (12.3 km) from Osborne Bend Trail and 8.9 mi (14.3 km) from Kentucky Reptile Zoo.
Opens in a new windowKim's Retreat: 3-BR Cabin w/ Hot Tub near Natural Bridge & Red River Gorge
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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.

Wellington 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 Wellington vacation homes are the perfect way for you to wing it.

Holiday houses in Wellington 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 Wellington 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 Wellington adventures, obvs.

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

Wellington Holiday Homes essential information

Accommodation
112 Holiday Homes
Lowest Price
AU$246
Highest Price
AU$1,702
Popular accommodation
Barn! 2-Hole Golf Course, BBall, Wiffleball, Soccer, Theater, Arcade, 2 Hot Tubs, Overlook Oasis! RRG, A-frame Cabin, NEW HOT TUB, Grill! Pet friendly, Hot Tub! Fire pit! Picnic area & Grill! Dog friendly Hardwicks Creek Haven@RRG, Sugarloaf Mountain Escape Secluded 3 bedroom, 5 acres, ATV, RV and boat storage., Tiny Home in the Heart of Red River Gorge, Red River Duplex - Unit 5 - 12 miles to the Gorge!, New Barndominium /Sleeps 24/ 4 Kitchens / 4 Hot Tubs / 4 Firepits, Treetop Escape | Hot Tub | Fire Pit & Epic Views, Kim's Retreat: 3-BR Cabin w/ Hot Tub near Natural Bridge & Red River Gorge

Top trending hotels in Wellington

Newly renovated 2 bedroom cabin near Cave Run Lake & Red River Gorge

Newly renovated 2 bedroom cabin near Cave Run Lake & Red River Gorge

2 out of 5
Wellington KY
The price is AU$337 per night from 15 Jan to 16 Jan
AU$337
15 Jan - 16 Jan 2026
includes taxes & fees
When you stay at this cabin in Wellington, you'll be within a 5-minute drive of Cave Run Lake.
Opens in a new windowNewly renovated 2 bedroom cabin near Cave Run Lake & Red River Gorge
The Cozy Den

The Cozy Den

Wellington KY
The price is AU$246 per night from 25 Dec to 26 Dec
AU$246
25 Dec - 26 Dec
includes taxes & fees
When you stay at this cabin in Wellington, you'll be within a 5-minute drive of Cave Run Lake.
Opens in a new windowThe Cozy Den
Primrose - Cave Run Lake OR Red River Gorge KY

Primrose - Cave Run Lake OR Red River Gorge KY

Wellington KY
When you stay at this chalet in Wellington, you'll be on a lake and 10 minutes by car from Menifee County Park.
Opens in a new windowPrimrose - Cave Run Lake OR Red River Gorge KY
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Natural Bridge State Resort Park

Natural Bridge State Resort Park

3.5 out of 5
2135 Natural Bridge Road Slade KY
With a stay at Natural Bridge State Resort Park in Slade, you'll be in a state park, just a 1-minute walk from Natural Bridge State Park and 7 minutes by foot ...
Opens in a new windowNatural Bridge State Resort Park
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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.

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.