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
2 Oct - 4 Oct
In two months
13 Nov - 15 Nov
In three months
11 Dec - 13 Dec
In four months
8 Jan - 10 Jan

Our top choices for Cumberland Gap holiday homes

Exterior

1. Blissful Bungalow across from LMU campus

Blissful Bungalow across from LMU campus
Harrogate
9.6 out of 10, Exceptional, (42 reviews)
"Very convenient to everything we needed to do, very clean and neat"
United States
Brandi L.
The price is AU$314
includes taxes & fees
20 Sept - 21 Sept
Blissful Bungalow across from LMU campus
Private kitchen

2. Harrogate Home Mountain View’s Dog Friendly

Harrogate Home Mountain View’s Dog Friendly
Harrogate
10.0 out of 10, Exceptional, (28 reviews)
"Great place to stay. "
United States
Jodi D.
The price is AU$384
includes taxes & fees
22 Sept - 23 Sept
Harrogate Home Mountain View’s Dog Friendly
Terrace/patio

3. 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, (26 reviews)
"The property was ideal. It was affordable, not too remote and had everything we needed."
United States
Julie R.
The price is AU$242
includes taxes & fees
22 Sept - 23 Sept
Home in Powell Valley Shores Close to Flat Hollow Marina & Powell Valley Marina
Dining

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

Private bungalow close to LMU, ARH, Cumberland Gap
Middlesboro
The price is AU$466
includes taxes & fees
21 Sept - 22 Sept
Private bungalow close to LMU, ARH, Cumberland Gap
Living area

5. 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 AU$533
includes taxes & fees
8 Oct - 9 Oct
Gorgeous 4-bedroom house in Middlesboro KY with WiFi, AC. Minutes from LMU
Property grounds

6. 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 AU$398
includes taxes & fees
29 Sept - 30 Sept
Charming 3-bedroom house with WiFi, AC in Pineville Kentucky
Room

7. 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
9.2 out of 10, Wonderful, (7 reviews)
"We enjoyed our stay. "
United States
Emily S.
The price is AU$542
includes taxes & fees
29 Sept - 30 Sept
Charming 3-bedroom house in the Crater City near State Parks, LMU, & hospitals.
Terrace/patio

8. 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 AU$424
includes taxes & fees
18 Sept - 19 Sept
Peaceful & Private! Pet-Friendly Williamsburg Home
Exterior

9. 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 AU$539
includes taxes & fees
19 Sept - 20 Sept
Welcoming 3-bedroom house with AC in charming Middlesboro
Living area

10. 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 AU$470
includes taxes & fees
18 Sept - 19 Sept
Peaceful ‘Mountain Cabin’ w/ Views in Williamsburg
Room

11. 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 AU$619
includes taxes & fees
22 Sept - 23 Sept
House close to ARH Hospital, Tackett Creek & LMU!
Private kitchen

12. 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 AU$686
includes taxes & fees
25 Sept - 26 Sept
Norris Lake Cabin Getaway, Sleeps 6・View・Fire pit
Terrace/patio

13. 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, (49 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 AU$996
includes taxes & fees
29 Sept - 30 Sept
Lake Front ★ No Wake w/ Dock ★ Gameroom ★ Carved FirePit ★ 2nd House Available
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

Holiday Inn Express Middlesboro by IHG

Holiday Inn Express Middlesboro by IHG

10/10 Excellent
"We had a wonderful stay at the Holiday Inn Express in Middlesboro, KY. The staff truly made our visit special—they were incredibly pleasant, helpful, and always made sure all of our needs were met. Every single day, we were greeted with warm smiles and friendly faces. They even went out of their way to give us excellent local recommendations for dinner. Their outstanding customer service made us feel right at home. We highly recommend this hotel to anyone visiting the area!"
Tolly 5-night trip
Posted 20 hours ago
Holiday Inn Express Middlesboro by IHG

Find out more about Cumberland Gap

Cumberland Gap Holiday Homes information

Number of reviews
142
Accommodation
236 Holiday Homes
Lowest Price
AU$242
Highest Price
AU$996