An aerial view of a town surrounded by mountains, with a mix of residential and commercial buildings, and a highway running through the center.

Search Holiday Homes in Middlesboro

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Save instantly and earn perks with One Key
    Learn about One Key

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
18 Sept - 20 Sept
In two months
30 Oct - 1 Nov
In three months
27 Nov - 29 Nov
In four months
25 Dec - 27 Dec

Our top choices for Middlesboro holiday homes

Dining

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

Private bungalow close to LMU, ARH, Cumberland Gap
Middlesboro
The price is £250
includes taxes & fees
6 Sept - 7 Sept
Private bungalow close to LMU, ARH, Cumberland Gap
Room

2. 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, (6 reviews)
"We enjoyed our stay. "
United States
Emily S.
The price is £299
includes taxes & fees
3 Oct - 4 Oct
Charming 3-bedroom house in the Crater City near State Parks, LMU, & hospitals.
Exterior

3. 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 £279
includes taxes & fees
4 Sept - 5 Sept
Welcoming 3-bedroom house with AC in charming Middlesboro
Room

4. 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 £306
includes taxes & fees
15 Sept - 16 Sept
House close to ARH Hospital, Tackett Creek & LMU!
Exterior

5. 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 £166
includes taxes & fees
7 Sept - 8 Sept
Blissful Bungalow across from LMU campus
Private kitchen

6. 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 £220
includes taxes & fees
8 Sept - 9 Sept
Harrogate Home Mountain View’s Dog Friendly
Terrace/patio

7. Peaceful & Private! Pet-Friendly Williamsburg Home

Peaceful & Private! Pet-Friendly Williamsburg Home
Williamsburg
10.0 out of 10, Exceptional, (4 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 £230
includes taxes & fees
7 Sept - 8 Sept
Peaceful & Private! Pet-Friendly Williamsburg Home
Living area

8. 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 £263
includes taxes & fees
3 Sept - 4 Sept
Peaceful ‘Mountain Cabin’ w/ Views in Williamsburg
Exterior detail

9. Min. to Laurel Cove, LMU & Union, & Bell Theater

Min. to Laurel Cove, LMU & Union, & Bell Theater
Pineville
4.8 out of 10, (3 reviews)
"I did not stay at this property due to a double booking. I stayed at a nearby house that needs to be cleaned better, specially the floors, a shower curtain needs to be added to the beautiful update in bathroom, some plates woukd be nice. House rules and check in, check out procedures, places to visit and eat nearby would have been helpful to have posted at the house. Overall was a decent place to stay, quiet neighborhood. I would at least consider staying again."
United States
Stephanie F.
The price is £197
includes taxes & fees
4 Sept - 5 Sept
Min. to Laurel Cove, LMU & Union, & Bell Theater
Living area

10. 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, (31 reviews)
"Beautiful home and location. Very spacious and clean."
United States
Christine G.
The price is £438
includes taxes & fees
16 Sept - 17 Sept
MOUNTAIN TOP CABIN WITH PARTNERING MARINA ON NORRIS LAKE
Property grounds

11. Norris Lake Cabin – Game Room, Dock & Stunning Views

Norris Lake Cabin – Game Room, Dock & Stunning Views
New Tazewell
9.8 out of 10, Exceptional, (17 reviews)
"Awesome place to stay. Friendly owners. Lake is beautiful. Would stay here again "
United States
Taryn T.
The price is £490
includes taxes & fees
21 Sept - 22 Sept
Norris Lake Cabin – Game Room, Dock & Stunning Views
Terrace/patio

12. 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 £586
includes taxes & fees
9 Sept - 10 Sept
Lake Front ★ No Wake w/ Dock ★ Gameroom ★ Carved FirePit ★ 2nd House Available
Property grounds

13. 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, (11 reviews)
"Beautiful house. Great stay"
United States
Kevin S.
The price is £217
includes taxes & fees
12 Sept - 13 Sept
Charming 3-bedroom house with WiFi, AC in Pineville Kentucky
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Middlesboro Hotel Reviews

Sleep Inn & Suites Middlesboro

Sleep Inn & Suites Middlesboro

10/10 Excellent
"Clean room, comfy bed…worked for us just passing through for the night. Staff was great."
Leia 1-night trip
Posted 12 hours ago
Sleep Inn & Suites Middlesboro

Find out more about Middlesboro

Middlesboro Holiday Homes information

Number of reviews
150
Accommodation
182 Holiday Homes
Lowest Price
£166
Highest Price
£586