A mountainous landscape with autumn foliage and a valley shrouded in mist.

Holiday Homes in Cumberland Gap

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Check prices for these dates

In two weeks
23 Oct - 25 Oct
In two months
4 Dec - 6 Dec
In three months
1 Jan - 3 Jan
In four months
29 Jan - 31 Jan

Our top choices for Cumberland Gap holiday homes

An aerial view of a campus with multiple buildings, a central tower, and a large open grassy area.

1. Blissful Bungalow across from LMU campus

Blissful Bungalow across from LMU campus
Harrogate
9.6 out of 10, Exceptional, (43 reviews)
"Very convenient to everything we needed to do, very clean and neat"
United States
Brandi L.
The price is NZ$396
includes taxes & fees
11 Oct - 12 Oct
Blissful Bungalow across from LMU campus
A modern kitchen with white cabinets, a central island with bar stools, a microwave, and a sign reading "EVERYDAY COOKING".

2. Harrogate Home Mountain View’s Dog Friendly

Harrogate Home Mountain View’s Dog Friendly
Harrogate
10.0 out of 10, Exceptional, (30 reviews)
"Great place to stay. "
United States
Jodi D.
The price is NZ$481
includes taxes & fees
21 Oct - 22 Oct
Harrogate Home Mountain View’s Dog Friendly
A living room with a stone fireplace, wooden walls, a sofa, a coffee table, and a TV mounted on the wall.

3. Gorgeous 4-bedroom house in Middlesboro KY with WiFi, AC. Minutes from LMU

Gorgeous 4-bedroom house in Middlesboro KY with WiFi, AC. Minutes from LMU
Middlesboro
10.0 out of 10, Exceptional, (19 reviews)
"Lots of room. Clean. Good host."
United States
Konnie D.
The price is NZ$604
includes taxes & fees
28 Oct - 29 Oct
Gorgeous 4-bedroom house in Middlesboro KY with WiFi, AC. Minutes from LMU
A dining area with a table set for four, a ceiling fan, and a sign above reading 'BE OUR GUEST'.

4. Private bungalow close to LMU, ARH, Cumberland Gap

Private bungalow close to LMU, ARH, Cumberland Gap
Middlesboro
8.0 out of 10, Very good, (1 review)
"This house was conveniently located. Upstairs bedroom was hot but everything else was nice."
United States
Leann L.
The price is NZ$594
includes taxes & fees
11 Oct - 12 Oct
Private bungalow close to LMU, ARH, Cumberland Gap
A bedroom with a bed, pillows, a nightstand, a lamp, a window with blinds, and a kitchen area with a refrigerator.

5. Charming 3-bedroom house in the Crater City near State Parks, LMU, & hospitals.

Charming 3-bedroom house in the Crater City near State Parks, LMU, & hospitals.
Middlesboro
9.0 out of 10, Wonderful, (8 reviews)
"We enjoyed our stay. "
United States
Emily S.
The price is NZ$687
includes taxes & fees
11 Oct - 12 Oct
Charming 3-bedroom house in the Crater City near State Parks, LMU, & hospitals.
A brick house with a covered porch, a front door, and a small garden area with potted plants.

6. Welcoming 3-bedroom house with AC in charming Middlesboro

Welcoming 3-bedroom house with AC in charming Middlesboro
Middlesboro
8.0 out of 10, Very good, (3 reviews)
"Great area to stay in "
United States
Corinna E.
The price is NZ$698
includes taxes & fees
8 Nov - 9 Nov
Welcoming 3-bedroom house with AC in charming Middlesboro
A living room with a TV on a wooden stand, a white chair, a small table, and a sofa.

7. House close to ARH Hospital, Tackett Creek & LMU!

House close to ARH Hospital, Tackett Creek & LMU!
Middlesboro
7.4 out of 10, Good, (3 reviews)
"Advertised would sleep 12, yes it had beds for 12, but I guess we were to share towels , could be cleaner, food and trash under sofa cushions. Had to hunt for the WiFi password."
United States
Elita W.
The price is NZ$710
includes taxes & fees
5 Nov - 6 Nov
House close to ARH Hospital, Tackett Creek & LMU!
A wooden deck with a railing, a brick building, and a door with a window.

8. Charming 3-bedroom house with WiFi, AC in Pineville Kentucky

Charming 3-bedroom house with WiFi, AC in Pineville Kentucky
Pineville
10.0 out of 10, Exceptional, (12 reviews)
"Clean and quiet place to stay when visiting the area. Will definitely consider this place again when we visit Pineville again! "
United States
seth r.
The price is NZ$506
includes taxes & fees
20 Oct - 21 Oct
Charming 3-bedroom house with WiFi, AC in Pineville Kentucky
A spacious living room with wooden beams, leather sofas, a wooden coffee table, and a mounted deer head.

9. Peaceful ‘Mountain Cabin’ w/ Views in Williamsburg

Peaceful ‘Mountain Cabin’ w/ Views in Williamsburg
Williamsburg
10.0 out of 10, Exceptional, (1 review)
"Had a wonderful stay at this cabin. It was very beautiful and the location was very peaceful and quiet but not too far from other things. Would definitely need a 4 wheel drive vehicle to get to the cabin. The host was very nice and had great communication. Definitely recommend this cabin for anyone looking to relax and enjoy nature."
United States
Nancy A.
The price is NZ$616
includes taxes & fees
12 Oct - 13 Oct
Peaceful ‘Mountain Cabin’ w/ Views in Williamsburg
A covered outdoor seating area with a sofa, chairs, and planters.

10. LMU Pine Mtn State Park Cumberland Gap Laurel Cove

LMU Pine Mtn State Park Cumberland Gap Laurel Cove
Pineville
10.0 out of 10, Exceptional, (1 review)
"Well cared for property with nice upgrades! Perfect for our stay, everything we needed, and accommodating. "
United States
Hope C.
The price is NZ$627
includes taxes & fees
5 Nov - 6 Nov
LMU Pine Mtn State Park Cumberland Gap Laurel Cove
An outdoor patio with a fire pit, surrounded by chairs and a pergola with string lights.

11. Home in Powell Valley Shores Close to Flat Hollow Marina & Powell Valley Marina

Home in Powell Valley Shores Close to Flat Hollow Marina & Powell Valley Marina
Speedwell
9.2 out of 10, Wonderful, (28 reviews)
"The property was ideal. It was affordable, not too remote and had everything we needed."
United States
Julie R.
The price is NZ$312
includes taxes & fees
11 Oct - 12 Oct
Home in Powell Valley Shores Close to Flat Hollow Marina & Powell Valley Marina
A covered outdoor deck with wooden flooring and metal chairs.

12. Peaceful & Private! Pet-Friendly Williamsburg Home

Peaceful & Private! Pet-Friendly Williamsburg Home
Williamsburg
10.0 out of 10, Exceptional, (5 reviews)
"Beautiful peaceful setting, great views! Host was very nice and helpful! Home was very clean and comfortable. Pet friendly, and kid friendly :)Highly recommend!"
United States
Alicia M.
The price is NZ$547
includes taxes & fees
9 Nov - 10 Nov
Peaceful & Private! Pet-Friendly Williamsburg Home
A modern kitchen with white cabinets, a stainless steel refrigerator, a wooden island with chairs, and a window providing natural light.

13. Norris Lake Cabin Getaway, Sleeps 6・View・Fire pit

Norris Lake Cabin Getaway, Sleeps 6・View・Fire pit
New Tazewell
8.0 out of 10, Very good, (1 review)
"It is a lovely dated home. We felt comfortable in our stay. It is situated between two curves so pulling in and out with a truck and trailer is a bit difficult as cars fly on that road. Other then that it had everything we needed for our short visit to town"
United States
Lauren W.
The price is NZ$1,050
includes taxes & fees
23 Oct - 24 Oct
Norris Lake Cabin Getaway, Sleeps 6・View・Fire pit
A spacious loft-style room with a high ceiling, large windows, a fireplace, and a cozy seating area.

14. MOUNTAIN TOP CABIN WITH PARTNERING MARINA ON NORRIS LAKE

MOUNTAIN TOP CABIN WITH PARTNERING MARINA ON NORRIS LAKE
Rock Harbor
9.6 out of 10, Exceptional, (32 reviews)
"The cabin is awesome. The marina is right down the road. Everything was great, I would definitely stay here again"
United States
Robert R.
The price is NZ$1,090
includes taxes & fees
3 Nov - 4 Nov
MOUNTAIN TOP CABIN WITH PARTNERING MARINA ON NORRIS LAKE
A wooden deck with wicker furniture, a view of a river, and a bridge in the distance.

15. Lake Front ★ No Wake w/ Dock ★ Gameroom ★ Carved FirePit ★ 2nd House Available

Lake Front ★ No Wake w/ Dock ★ Gameroom ★ Carved FirePit ★ 2nd House Available
LaFollette
10.0 out of 10, Exceptional, (50 reviews)
"House was spectacular, beds were very comfortable, plenty to do in the area and the lake was just beautiful. Would definitely stay here again!"
United States
Brooke R.
The price is NZ$1,366
includes taxes & fees
19 Oct - 20 Oct
Lake Front ★ No Wake w/ Dock ★ Gameroom ★ Carved FirePit ★ 2nd House Available
A two-story house with a balcony, a visible number '121' on the side, and a small garden area with shrubs.

16. Norris Lake retreat with boat slip in Deerfield

Norris Lake retreat with boat slip in Deerfield
LaFollette
The price is NZ$1,402
includes taxes & fees
9 Nov - 10 Nov
Norris Lake retreat with boat slip in Deerfield
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 Cumberland Gap Hotel Reviews

Sleep Inn & Suites Middlesboro

Sleep Inn & Suites Middlesboro

10/10 Excellent
"Room is very clean and staff is very friendly. Plenty of parking."
Cheryl 1-night trip
Posted 18 hours ago
Sleep Inn & Suites Middlesboro

Find out more about Cumberland Gap

Cumberland Gap Holiday Homes information

Number of reviews
232
Accommodation
232 Holiday Homes
Lowest Price
NZ$312
Highest Price
NZ$1,402