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

Middlesboro Vacation Rentals

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Check prices for these dates

In two weeks
21 Aug - 23 Aug
In two months
2 Oct - 4 Oct
In three months
30 Oct - 1 Nov
In four months
27 Nov - 29 Nov

Our top choices for Middlesboro vacation rentals

Desk, iron/ironing board, WiFi, bed sheets

1. 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 AED 750
AED 1,449 total
includes taxes & fees
7 Aug - 8 Aug
Charming 3-bedroom house in the Crater City near State Parks, LMU, & hospitals.
Exterior

2. 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 AED 739
AED 1,437 total
includes taxes & fees
7 Aug - 8 Aug
Welcoming 3-bedroom house with AC in charming Middlesboro
Desk, WiFi, bed sheets

3. 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 AED 662
AED 1,383 total
includes taxes & fees
20 Aug - 21 Aug
House close to ARH Hospital, Tackett Creek & LMU!
Dining

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

Private bungalow close to LMU, ARH, Cumberland Gap
Middlesboro
The price is AED 575
AED 1,227 total
includes taxes & fees
8 Aug - 9 Aug
Private bungalow close to LMU, ARH, Cumberland Gap
House (1 Bedroom) | Interior

5. Peaceful Mountain Cabin w/ Views in Williamsburg

Peaceful Mountain Cabin w/ Views in Williamsburg
2.0 star property
Williamsburg
2.0 out of 10, (1 review)
"The owners were very polite. The only issue I had was that the listing online did not say anything about it being fully solar powered with no electricity. We left in the middle of the night the first night because there was no power at all."
United States
Chandler
The price is AED 463
AED 1,253 total
includes taxes & fees
6 Aug - 7 Aug
Peaceful Mountain Cabin w/ Views in Williamsburg
Coffee/tea maker, fridge, microwave, oven

6. Harrogate Home Mountain View’s Dog Friendly

Harrogate Home Mountain View’s Dog Friendly
Harrogate
10.0 out of 10, Exceptional, (26 reviews)
"Great place to stay. "
United States
Jodi D.
The price is AED 509
AED 942 total
includes taxes & fees
11 Aug - 12 Aug
Harrogate Home Mountain View’s Dog Friendly
Exterior

7. Blissful Bungalow across from LMU campus

Blissful Bungalow across from LMU campus
Harrogate
9.6 out of 10, Exceptional, (39 reviews)
"Very convenient to everything we needed to do, very clean and neat"
United States
Brandi L.
The price is AED 400
AED 815 total
includes taxes & fees
6 Aug - 7 Aug
Blissful Bungalow across from LMU campus
Property grounds

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, (9 reviews)
"clean house very beautiful, host was amazing, scenery stunning. "
United States
Evelyn B.
The price is AED 585
AED 1,086 total
includes taxes & fees
6 Aug - 7 Aug
Charming 3-bedroom house with WiFi, AC in Pineville Kentucky
Outdoor dining

9. The House on Park Avenue-minutes to music venues Laurel Cove and Bell Theater!

The House on Park Avenue-minutes to music venues Laurel Cove and Bell Theater!
Pineville
9.4 out of 10, Exceptional, (6 reviews)
"The home was just perfect for what we needed. Looking forward to seeing how it comes out when all construction is finished! Host was very responsive. Will stay again"
United States
Kami L.
The price is AED 694
AED 1,377 total
includes taxes & fees
8 Aug - 9 Aug
The House on Park Avenue-minutes to music venues Laurel Cove and Bell Theater!
Dining

10. 2-bedroom loft apartment in adorable Pineville close to Pine Mountain State Park

2-bedroom loft apartment in adorable Pineville close to Pine Mountain State Park
Pineville
10.0 out of 10, Exceptional, (1 review)
"We stayed for the 95th Mountain Laurel Festival and LOVED the location, access to all festival activities, and how easy it was to communicate with the renter. We hope to make this a tradition and will stay here again!"
United States
jennifer w.
The price is AED 623
AED 1,286 total
includes taxes & fees
3 Sep - 4 Sep
2-bedroom loft apartment in adorable Pineville close to Pine Mountain State Park
Interior

11. Calm Country Oasis - Creek, ATV Trls & Norris Lake

Calm Country Oasis - Creek, ATV Trls & Norris Lake
Speedwell
9.6 out of 10, Exceptional, (25 reviews)
"Clean home, responsive host, beautiful location, family friendly."
United States
Anna S.
The price is AED 400
AED 964 total
includes taxes & fees
6 Aug - 7 Aug
Calm Country Oasis - Creek, ATV Trls & Norris Lake
Interior

12. Serenity Villa: Luxurious Retreat with Hot Tub, Rooftop Deck & Mountain View's

Serenity Villa: Luxurious Retreat with Hot Tub, Rooftop Deck & Mountain View's
Sharps Chapel
10.0 out of 10, Exceptional, (10 reviews)
"This was definitely the most romantic VRBO we’ve stayed at!!! Very clean, and the view from all of the balconies was incredible!!! "
United States
Stan N.
The price is AED 691
AED 1,261 total
includes taxes & fees
1 Sep - 2 Sep
Serenity Villa: Luxurious Retreat with Hot Tub, Rooftop Deck & Mountain View's
A wooden dock leading to a small wooden platform with a metal railing, surrounded by trees and a body of water.

13. Norris Lake Butterfly Landing - Recently Updated 16 Guest Lakefront w Dock Home

Norris Lake Butterfly Landing - Recently Updated 16 Guest Lakefront w Dock Home
Flat Hollow Marina
9.8 out of 10, Exceptional, (42 reviews)
"Wonderful time at this property"
United States
Susan K.
Norris Lake Butterfly Landing - Recently Updated 16 Guest Lakefront w Dock Home
TV

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, (30 reviews)
"Beautiful home and location. Very spacious and clean."
United States
Christine G.
The price is AED 949
AED 1,954 total
includes taxes & fees
12 Aug - 13 Aug
MOUNTAIN TOP CABIN WITH PARTNERING MARINA ON NORRIS LAKE
Interior

15. The Highlands Cabin ~ Norris Lake Views & Modern Comfort

The Highlands Cabin ~ Norris Lake Views & Modern Comfort
New Tazewell
10.0 out of 10, Exceptional, (7 reviews)
"The cabin was clean, cozy, and overall amazing! "
United States
Fannie
The price is AED 479
AED 775 total
includes taxes & fees
6 Aug - 7 Aug
The Highlands Cabin ~ Norris Lake Views & Modern Comfort
Property grounds

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

Norris Lake Cabin – Game Room, Dock & Stunning Views
New Tazewell
9.8 out of 10, Exceptional, (16 reviews)
"Awesome place to stay. Friendly owners. Lake is beautiful. Would stay here again "
United States
Taryn T.
The price is AED 1,277
AED 2,861 total
includes taxes & fees
29 Aug - 30 Aug
Norris Lake Cabin – Game Room, Dock & Stunning Views
Terrace/patio

17. Peaceful cabin with AC in charming Tazewell. Welcome to relaxation!

Peaceful cabin with AC in charming Tazewell. Welcome to relaxation!
Tazewell
9.2 out of 10, Wonderful, (11 reviews)
"The hosts were wonderful, very accommodating and helpful through our stay. The cabin was clean and nicely put together for a relaxing visit."
United States
Sharon W.
The price is AED 349
AED 584 total
includes taxes & fees
9 Aug - 10 Aug
Peaceful cabin with AC in charming Tazewell. Welcome to relaxation!
Interior

18. One Bedroom Rustic Cabin

One Bedroom Rustic Cabin
Speedwell
The price is AED 180
AED 335 total
includes taxes & fees
6 Aug - 7 Aug
One Bedroom Rustic Cabin
Interior

19. The Lodge Cabin ~Norris Lake Views and Mountain Backdrops

The Lodge Cabin ~Norris Lake Views and Mountain Backdrops
New Tazewell
10.0 out of 10, Exceptional, (4 reviews)
"Everything was perfect!"
United States
Heather M.
The price is AED 479
AED 771 total
includes taxes & fees
10 Aug - 11 Aug
The Lodge Cabin ~Norris Lake Views and Mountain Backdrops
Coffee/tea maker, fridge, microwave, oven

20. Remodeled Western Country Getaway Near Lake & Trails

Remodeled Western Country Getaway Near Lake & Trails
LaFollette
10.0 out of 10, Exceptional, (4 reviews)
"Very clean and nice apartment. Just as advertised. Had everything we needed and we were very pleased. Great place! You will not be disappointed. We will definitely be going back!"
United States
Gregory T.
The price is AED 290
AED 686 total
includes taxes & fees
13 Aug - 14 Aug
Remodeled Western Country Getaway Near Lake & Trails
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 Middlesboro Hotel Reviews

Sleep Inn & Suites Middlesboro

Sleep Inn & Suites Middlesboro

10/10 Excellent
"It is a well maintained property and good value."
Lynn 2-night trip
Posted 19 hours ago
Sleep Inn & Suites Middlesboro

Frequently asked questions

Are there vacation rentals in Middlesboro?

Yes, we offer vacation rentals close to the most popular sights in Middlesboro, or you can choose a secluded option if you'd like a relaxing place to stay. Nature enthusiasts will enjoy the mountain landscape in Middlesboro. Make sure you have time to check out the churches while you're in the area.

What's the top vacation rental that Middlesboro has to offer?

Beautiful Norris Lake WATERFRONT. Near Flat Hollow Marina. Private dock.: This vacation home rental near Middlesboro is located on a lake and has a balcony, a selection of games, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a fridge, a stovetop, and a microwave, so you can cook with friends or family.

How many vacation rentals are there in Middlesboro?

With 6 Expedia vacation rentals, you're sure to find just the right place for your Middlesboro stay.

What’s there to see and do in Middlesboro?

Cultural attractions include Bell County Historical Society Museum, whereas Kentucky Ridge State Forest is a spot to enjoy nature. While here, Cumberland Gap National Historical Park and Middlesboro Country Club are other places worth a visit.

What’s a vacation rental in Middlesboro like?

Vacation rentals are private properties you can stay in for short or long periods in Middlesboro. Vacation rentals feature amenities such as kitchens and laundry facilities so you'll have everything you need. If you're concerned about a sanitized environment, vacation rentals can offer a sense of security away from public hotel elevators and lobbies bustling with people while still allowing you the experience of travel. You'll also have more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a popular choice for small groups.