Find the best cottages in Middlesboro - We found 2 exact matches
About Middlesboro Cottage Rentals on Vacation Cottage
For travelers seeking a comfortable and luxurious retreat in Middlesboro, Vacation Cottage has you covered. Opt for a cottage rental, lake house retreat, or summer home resort and enjoy the flexibility of a hotel. With over 2 options available in Middlesboro on Vacation Cottage, we can assist you in finding the perfect accommodation.
Elevate your next vacation with a picturesque cottage rental in Middlesboro, offering top-notch amenities such as swimming pools, fitness centers, Wi-Fi, luxury suites, and fully-equipped kitchens. Discover unbeatable deals on outdoor vacation cottages, lake houses, and summer home retreats. Start planning your trip to Middlesboro today and secure your accommodation in minutes on our website.
Whether it's a short-term getaway or a long-term seasonal stay, find the perfect cottage rental, lake house, or summer home for your favorite travel destinations. Compare options with Vacation Cottage and stay close to nature.
Frequently Asked Questions About Middlesboro Rental Cottages
What are the top rated Cottage 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 Cottage Rentals in Middlesboro:
- 4.6 miles from LMU. Cozy 2-bedroom Lustron home located in Middlesboro, Ky,
- Gorgeous 4-bedroom house in Middlesboro KY with WiFi, AC. Minutes from LMU
- Minutes from LMU, ARH, and Cumberland Gap National Historic Park, Laurel Cove Music Festival, and Pine Mountain State Resort Park
- Spacious Renovated Ranch Retreat near Tackett Creek & Cumberland Gap Park, & LMU
- 1928 Home in the heart of Cumberland Gap
- Mountain Views - LMU 1 1/2
- Holiday Inn Express Middlesboro by IHG
- Blissful Bungalow across from LMU campus
- Luxury Brooklyn St APT - Near LMU & Nat’l Park
- Sleep Inn & Suites Middlesboro
How much does it cost to rent a cottage in Middlesboro?
The average cost for a cottage rental in Middlesboro is $212 per night. Vacation Cottage has a wide list of great cottages near Middlesboro that would suit your needs. There are single and multiple rooms for solo trips or family vacations.
Are there any cottages in Middlesboro that allow pets?
Yes, here are the top cottage rentals in Middlesboro that allow you to bring your pet:
- Cozy Cumberland Gap Cottage Near LMU & Nat’l Park
- The Cottage by ARH Hospital, ATV Trails, and LMU!
- Mountain Views - LMU 1 1/2
- Minutes from LMU, ARH, and Cumberland Gap National Historic Park, Laurel Cove Music Festival, and Pine Mountain State Resort Park
- The Olde Mill Inn Bed & Breakfast
- Luxury Brooklyn St APT - Near LMU & Nat’l Park
See all pet-friendly vacation rentals in Middlesboro on Vacation Cottage
Do you have any rental cottages in Middlesboro that are suitable for families?
Most of our listed cottages are suitable for families. Check out the complete list of cottages in Middlesboro to find one that works for you.
Are there quality cottages in Middlesboro that have indoor swimming pools?
As of 2026, the data from Vacation Cottage shows that there are Over 2 private swimming pools or cottages with indoor pools in the Middlesboro area along with other great amenities.
Do any cottages in Middlesboro have hot tubs?
About 2 cottages in Middlesboro boast of premium hot tubs. Some of the popular places to stay with hot tubs include:
See all holiday vacation rentals in Middlesboro on Vacation CottageAre there luxury cottages in Middlesboro?
Yes, there are luxury cottages in Middlesboro. Find more luxury, lakefront, winter, & last-minute cottage rentals near Middlesboro.

























