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Vacation Homes in Pennington Gap

Charming 1-bedroom house in welcoming Big Stone Gap Virginia!
Enjoy cooking in this well-equipped kitchen with a microwave, oven, dishwasher, and sink.

Charming 1-bedroom house in welcoming Big Stone Gap Virginia!

10.0 out of 10, Exceptional, (2)
"This newly remodeled home was perfect for our family. There were four of us but there was room for two more to sleep. Everything was so clean! We loved the fact that the owner immediately responded when we had questions. The house is walking distance to the cute main street in Big Stone Gap and there are lots of beautiful hiking paths in the nearby mountains. We would definitely stay here again. "
Charming 1-bedroom house in welcoming Big Stone Gap Virginia!
Handicapped Friendly House in the peaceful country side
Relax on the deck with Adirondack chairs and a small table, surrounded by trees.

Handicapped Friendly House in the peaceful country side

10.0 out of 10, Exceptional, (25)
"Check in is easy and Nell is very responsive. This was my family's second time staying here and we will definitely stay again. "
Handicapped Friendly House in the peaceful country side
Welcome to The Mayor's Retreat! 4-bedroom house in Evarts KY. Book now
Enjoy outdoor dining or relaxation on the patio with a metal table and chairs.

Welcome to The Mayor's Retreat! 4-bedroom house in Evarts KY. Book now

10.0 out of 10, Exceptional, (3)
"Great location very close to Black Mountain. Host was awesome"
Welcome to The Mayor's Retreat! 4-bedroom house in Evarts KY. Book now
Bed and Biscuit Inn Pet friendly ! Near Kingdom come park & Pine mtn.
Relax by the fire pit surrounded by comfortable Adirondack chairs and a cozy rug.

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

9.8 out of 10, Exceptional, (6)
"Perfect little place to hang with the pups and use as a base camp for lots of great hiking in the area. "
Bed and Biscuit Inn Pet friendly ! Near Kingdom come park & Pine mtn.
Harlan, KY Modern Private Guesthouse 302 Historic Downtown (Vela's Villas)
Stroll up to the charming single-story house with a front door and small porch area.

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

8.8 out of 10, Excellent, (3)
"We will rent this property again :)"
Harlan, KY Modern Private Guesthouse 302 Historic Downtown (Vela's Villas)
Harlan, KY GuestHouse 300 Vacation/Weddings/Events (Cole Mansion)
Stunning two-story home with a symmetrical facade, featuring a brick and stone exterior, and a charming porch area.

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

10.0 out of 10, Exceptional, (1)
"Had a few issues but they were resolved."
Harlan, KY GuestHouse 300 Vacation/Weddings/Events (Cole Mansion)
Modern Appalachian Vacation Rental w/ River Access
Relax in this spacious living area with a high ceiling, featuring a sofa and fireplace.

Modern Appalachian Vacation Rental w/ River Access

9.8 out of 10, Exceptional, (8)
"We had a very beautiful and restful stay, thank you!"
Modern Appalachian Vacation Rental w/ River Access
Appalachian country views and hikes.
Relax in this inviting living space, featuring a comfortable sofa, coffee table, and area rug.

Appalachian country views and hikes.

9.6 out of 10, Exceptional, (14)
"What a lovely place. Everything we needed and then some. Would stay here again. So relaxing. The view, ping pong, & super happy to discover puzzles for us to do on the rainy day!(Only issue we had was it was wasp season & they kept getting in. Glad they were slow ones!)"
Appalachian country views and hikes.
Roomy 1896 Victorian Farmhouse Farm Stay in Lee Virginia
Stunning two-story house with a central chimney and gabled roof, offering a serene outdoor space with patio and lawn.

Roomy 1896 Victorian Farmhouse Farm Stay in Lee Virginia

10.0 out of 10, Exceptional, (9)
"We enjoyed our stay at the farmhouse. Close enough to Pennington Gap for groceries and restaurants. "
Roomy 1896 Victorian Farmhouse Farm Stay in Lee Virginia
Gorgeous Historic Haven downtown (Rare find)
Situated on a well-maintained lawn, this charming home features a front porch and patio area perfect for relaxation or entertaining.

Gorgeous Historic Haven downtown (Rare find)

Gorgeous Historic Haven downtown (Rare find)
Perfect location above Big Cherry Brewing
Welcome to BIG CHERRY, a charming corner building with a glass door entrance.

Perfect location above Big Cherry Brewing

Perfect location above Big Cherry Brewing
Harlan, Ky Modern Private Guesthouse 304 Historic Downtown (Vela's Villas)
Stunning single-story home with a central entrance and two windows on each side, set amidst a beautifully manicured lawn.

Harlan, Ky Modern Private Guesthouse 304 Historic Downtown (Vela's Villas)

10.0 out of 10, Exceptional, (1)
"We loved our stay at Vela’s Villa! We had a family gathering and it was wonderful for us to all be together we had a family reunion and it was such a great stay! thanks so much"
Harlan, Ky Modern Private Guesthouse 304 Historic Downtown (Vela's Villas)
Unreal Bungalow downtown (Perfect location)
Stylish home with a front porch, white door, and well-manicured lawn.

Unreal Bungalow downtown (Perfect location)

Unreal Bungalow downtown (Perfect location)
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 Pennington Gap Hotel Reviews

Quality Inn

Quality Inn

10/10 Excellent
"Great value"
herbert 1-night trip
Posted 2 days ago
Quality Inn