Middlesboro Vacation Rentals from ￥28,628: Search Short-Term Rentals

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Our top choices for Middlesboro vacation rentals

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

Middlesboro

￥53,845 total

includes taxes & fees

Sep 8 - Sep 9

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

Middlesboro

Emily S.

￥63,303 total

includes taxes & fees

Sep 8 - Sep 9

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

Middlesboro

Corinna E.

￥62,952 total

includes taxes & fees

Sep 8 - Sep 9

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

Middlesboro

Elita W.

￥62,776 total

includes taxes & fees

Aug 27 - Aug 28

5. Blissful Bungalow across from LMU campus

Harrogate

Brandi L.

￥36,102 total

includes taxes & fees

Sep 8 - Sep 9

6. Harrogate Hideaway - 5 Min to LMU & Nat`l Park

Harrogate

Amy C.

￥33,721 total

includes taxes & fees

Sep 15 - Sep 16

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

Speedwell

Anna S.

￥41,787 total

includes taxes & fees

Sep 7 - Sep 8

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

Tazewell

Carla C.

￥27,291 total

includes taxes & fees

Aug 27 - Aug 28

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Top Middlesboro Hotel Reviews

Holiday Inn Express Middlesboro by IHG

10/10 Excellent

"This is my absolute favorite place to stay on my route from Ohio to East Tennessee and back.. the staff is very friendly the hotel is always clean breakfast is wonderful and I'm picky.. I used to manage nights in hotels so I have experience in the hospitality industry and I absolutely love this location."

Beautiful Norris Lake WATERFRONT. Near Flat Hollow Marina. Private dock.

10/10 Excellent

"We had an amazing time staying here. We really enjoyed using the boat for a day and getting out on the water. Carmen was a great host and very prompt at communicating if we needed anything. We highly recommend anyone that wants to come enjoy a lake getaway."

Serene cabin with dock/swim platform in charming Speedwell

10/10 Excellent

"The cabin is in a great location. It’s close to the Flat Hollow Marina and is not too close to the nearby houses. It has everything you would need including two coffee makers; a regular basket one and one that takes pods. We would definitely stay here again."

Brand New, Spacious 9 bedroom, 9 1/2 bath Waterfront house in Lakeside Estates

10/10 Excellent

"Property was gorgeous. The balconies on all floors were more expansive than other properties we have rented before and had plenty of seating for all. I should also mention the new Weber Grill and hot tub. Nancy was a great host and promptly responded with any questions. The game room included a ping pong table, pop-a-shot basketball, and many board games for all ages and was a family favorite. If you are looking for a great spot for a family weekend at the lake, this spot."

Find out more about Middlesboro

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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 Mall 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.

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Check prices for these dates

Our top choices for Middlesboro vacation rentals

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

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

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

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

5. Blissful Bungalow across from LMU campus

6. Harrogate Hideaway - 5 Min to LMU & Nat`l Park

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

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

9. Harrogate Home Mountain View’s Dog Friendly

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

11. One Bedroom Rustic Cabin

12. Quaint Studio APT Near ATV Trails & Norris Lake

13. Peaceful & Private! Pet-Friendly Williamsburg Home

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

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

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

17. 2-bedroom loft apartment in adorable Pineville close to Pine Mountain State Park

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

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

20. Peaceful & Private! Pet-friendly Williamsburg Home

Find vacation rentals that suit your style

Top Middlesboro Hotel Reviews

Holiday Inn Express Middlesboro by IHG

Holiday Inn Express Williamsburg by IHG

Midnight Mooring

Imperial Inn Tazewell

Beautiful Norris Lake WATERFRONT. Near Flat Hollow Marina. Private dock.

Suburban Studios Middlesboro

Serene cabin with dock/swim platform in charming Speedwell

Quality Inn Harlan

Brand New, Spacious 9 bedroom, 9 1/2 bath Waterfront house in Lakeside Estates

Find out more about Middlesboro

Frequently asked questions

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