What are the top rated Winter Rentals in Middlesboro?

There are a lot of options in Middlesboro. If you plan on staying in the Middlesboro area, consider making a reservation for a few nights at one of these properties as these have been rated the top Winter Rentals in Middlesboro: Minutes from LMU, ARH, and Cumberland Gap National Historic Park, Laurel Cove Music Festival, and Pine Mountain State Resort Park Holiday Inn Express Middlesboro by IHG Luxury Brooklyn St APT - Near LMU & Nat’l Park Blissful Bungalow across from LMU campus Holiday Inn Express Middlesboro by IHG Cozy Cumberland Gap Cottage Near LMU & Nat’l Park Mountain View Retreat 5 min to LMU The Cottage by ARH Hospital, ATV Trails, and LMU! Sleep Inn & Suites Middlesboro Econo Lodge Middlesboro

How much does it cost to rent a place to stay near Middlesboro in the wintertime?

The average cost for winter rentals in Middlesboro is $190 per night. StayAndPlay.com has a wide list of great winter places to stay near Middlesboro that would suit your preferences. There are single and multiple rooms for solo trips or family vacations.

Are there any winter cottages/chalets in Middlesboro that allow pets?

Yes, here are the top cottage/chalet rentals in Middlesboro that allow you to bring your pet or dog: 1928 Home in the heart of Cumberland Gap Charming 3-bedroom house in the Crater City near State Parks, LMU, & hospitals. Historic Cabin on the Tolliver Manor Luxury Brooklyn St APT - Near LMU & Nat’l Park Minutes from LMU, ARH, and Cumberland Gap National Historic Park, Laurel Cove Music Festival, and Pine Mountain State Resort Park Holiday Inn Express Middlesboro by IHG Cozy Cumberland Gap Cottage Near LMU & Nat’l Park See all pet-friendly vacation rentals in Middlesboro on StayAndPlay

Do you have any winter rentals in Middlesboro that are suitable for families?

Most of our rentals homes are suitable for families. Check out the complete list of places to stay in Middlesboro to find what works for you.

Are there winter accommodations in Middlesboro that have indoor swimming pools?

As of 2025, the data from StayAndPlay shows that there are over 3 private swimming pools or indoor pools accommodations near Middlesboro along with other great amenities.

Do any winter holiday rentals in Middlesboro have hot tubs?

About 3 holiday rentals in Middlesboro boast of premium hot tubs. Some of the popular winter places to stay with hot tubs include: Middlesboro Rentals with hot tub

Are there luxury winter rentals in Middlesboro?

Yes, there are many luxury places to stay in Middlesboro for the winter season. Find out more luxury, lakefront, winter, & last-minute rental homes near Middlesboro with all the best amenities for your next trip.