Book Holiday Homes in Pennington Gap

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Featured Holiday Homes in Pennington Gap

Harlan, KY Modern Private Guesthouse 302 Historic Downtown (Vela's Villas)

Harlan, KY Modern Private Guesthouse 302 Historic Downtown (Vela's Villas)

Harlan
Stay at this vacation home in Harlan. Enjoy a water park, a garden, and cable/satellite TV service. Popular attraction Rapid River Lodge & Water Park is located ...
Harlan, KY Modern Private Guesthouse 302 Historic Downtown (Vela's Villas)
Harlan, KY GuestHouse 300 Vacation/Weddings/Events (Cole Mansion)

Harlan, KY GuestHouse 300 Vacation/Weddings/Events (Cole Mansion)

Harlan
Stay at this vacation home in Harlan. Enjoy a water park, a garden, and patios. Popular attraction Rapid River Lodge & Water Park is located nearby.
Harlan, KY GuestHouse 300 Vacation/Weddings/Events (Cole Mansion)
Modern Appalachian Vacation Rental w/ River Access

Modern Appalachian Vacation Rental w/ River Access

Pennington Gap
Stay at this vacation home in Pennington Gap. Enjoy patios, cable/satellite TV service, and an in-room coffeemaker. Popular attraction Cave Spring Park is located ...
Modern Appalachian Vacation Rental w/ River Access
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Posh Mountain Camping w/ 120" Screen Theater ·Hot-Tub · Firepit

Posh Mountain Camping w/ 120" Screen Theater ·Hot-Tub · Firepit

Jonesville
The price is NZ$418 per night from 24 Dec to 25 Dec
NZ$418
includes taxes & fees
24 Dec - 25 Dec
Stay at this vacation home in Jonesville. Enjoy free WiFi, a garden, and patios.
Posh Mountain Camping w/ 120" Screen Theater ·Hot-Tub · Firepit
1896 Victorian Farmhouse

1896 Victorian Farmhouse

Dryden
Stay at this vacation home in Dryden. Enjoy free WiFi, a garden, and balconies or patios. Popular attraction Cave Spring Park is located nearby.
1896 Victorian Farmhouse
Handicapped Friendly House in the peaceful country side

Handicapped Friendly House in the peaceful country side

Jonesville
Book a stay at this family-friendly vacation home in Jonesville. Enjoy free WiFi, a garden, and patios.
Handicapped Friendly House in the peaceful country side
Gated Mansion: Tennis Court, Movie Theater, Views, Pool, & free vineyard tours !

Gated Mansion: Tennis Court, Movie Theater, Views, Pool, & free vineyard tours !

Big Stone Gap
Book a stay at this family-friendly vacation home in Big Stone Gap. Enjoy free WiFi, a garden, and tennis courts. Popular attractions High Knob and Crooked Road ...
Gated Mansion: Tennis Court, Movie Theater, Views, Pool, & free vineyard tours !
Appalachian country views and hikes.

Appalachian country views and hikes.

Sneedville
Stay at this vacation home in Blackwater. Enjoy free WiFi, a garden, and patios. Popular attraction Elrod Falls is located nearby.
Appalachian country views and hikes.
Bed and Biscuit Inn 
Pet friendly !
Near Kingdom come park & Pine mtn.

Bed and Biscuit Inn Pet friendly ! Near Kingdom come park & Pine mtn.

Partridge
Stay at this vacation home in Letcher County. Enjoy an in-room coffeemaker and air conditioning. Popular attraction Kingdom Come State Park is located ...
Bed and Biscuit Inn Pet friendly ! Near Kingdom come park & Pine mtn.
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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.

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

Holiday houses in Pennington Gap 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 Pennington Gap 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 Pennington Gap adventures, obvs.

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

Pennington Gap Holiday Homes essential information

Accommodation
13 Holiday Homes
Lowest Price
NZ$140
Highest Price
NZ$418
Popular accommodation
Harlan, KY Modern Private Guesthouse 302 Historic Downtown (Vela's Villas), Harlan, KY GuestHouse 300 Vacation/Weddings/Events (Cole Mansion), Modern Appalachian Vacation Rental w/ River Access, Posh Mountain Camping w/ 120" Screen Theater ·Hot-Tub · Firepit , 1896 Victorian Farmhouse, Handicapped Friendly House in the peaceful country side, Gated Mansion: Tennis Court, Movie Theater, Views, Pool, & free vineyard tours !, Appalachian country views and hikes., Bed and Biscuit Inn Pet friendly ! Near Kingdom come park & Pine mtn.

Top trending hotels in Pennington Gap

Modern Appalachian Vacation Rental w/ River Access

Modern Appalachian Vacation Rental w/ River Access

Pennington Gap
Stay at this vacation home in Pennington Gap. Enjoy patios, cable/satellite TV service, and an in-room coffeemaker. Popular attraction Cave Spring Park is located ...
Modern Appalachian Vacation Rental w/ River Access
Modern Appalachian Vacation Rental w/ River Access

Modern Appalachian Vacation Rental w/ River Access

3 out of 5
385 Screech Trl, Pennington Gap, VA
Stay at this 3-star cottage in Pennington Gap. Enjoy free parking, in-room fireplaces, and air conditioning. Popular attraction Cave Spring Park is located ...
Modern Appalachian Vacation Rental w/ River Access
Quality Inn & Suites

Quality Inn & Suites

2.5 out of 5
4609 Aerial Way, Big Stone Gap, VA
Fully refundableReserve now, pay when you stay
The price is NZ$140 per night from 5 Jan to 6 Jan
NZ$140
includes taxes & fees
5 Jan - 6 Jan 2025
Stay at this hotel in Big Stone Gap. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions ...
Quality Inn & Suites
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Comfort Inn & Suites

Comfort Inn & Suites

2.5 out of 5
128 James Richardson Lane, Rogersville, TN
Fully refundableReserve now, pay when you stay
The price is NZ$166 per night from 9 Jan to 10 Jan
NZ$166
includes taxes & fees
9 Jan - 10 Jan 2025
Book a stay at this golf hotel in Rogersville. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular ...
Comfort Inn & Suites
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See all available properties in Pennington Gap
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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.