Find Vacation Rentals in Middlesboro

We have 83 properties to choose from
Anytime
Guests
Anytime
Guests

Popular Middlesboro Vacation Rentals

Find the perfect Middlesboro vacation rental

Apartment Middlesboro
from $150 per night
4 guests ∙ 2 bedrooms

Apartment

4.9
Outstanding(32 ratings)
Middlesboro, Bell County, Kentucky, United States
Details
House Middlesboro
from $226 per night
House ∙ 9 guests ∙ 4 bedrooms

172 m² House

5.0
Outstanding(2 ratings)
Middlesboro, Bell County, Kentucky, United States
Details
Cottage Middlesboro
from $168 per night
7 guests ∙ 3 bedrooms

Cottage

4.7
Excellent(50 ratings)
Middlesboro, Bell County, Kentucky, United States
Details
House Middlesboro
from $223 per night
6 guests ∙ 3 bedrooms

House

4.9
Outstanding(98 ratings)
Middlesboro, Bell County, Kentucky, United States
Details
House Middlesboro
from $172 per night
8 guests ∙ 4 bedrooms

House

5.0
Outstanding(2 ratings)
Middlesboro, Bell County, Kentucky, United States
Details
Bed and breakfast Middlesboro
from $137 per night
Bed and breakfast ∙ 6 guests ∙ 1 bedroom

The Olde Mill Inn Bed & Breakfast

5.0
Outstanding
Middlesboro, Bell County, Kentucky, United States
Details
Motel Middlesboro
from $84 per night
4 guests ∙ 1 bedroom

Motel

3.5
Good(64 ratings)
Middlesboro, Bell County, Kentucky, United States
Details
Motel Middlesboro
from $86 per night
2 guests ∙ 1 bedroom

Motel

3.5
Good(65 ratings)
Middlesboro, Bell County, Kentucky, United States
Details
Motel Middlesboro
from $79 per night
4 guests ∙ 1 bedroom

Motel

3.5
Good(65 ratings)
Middlesboro, Bell County, Kentucky, United States
Details
Show more

Pet-Friendly Homes and Apartments

House  Middlesboro
from $165 per night
10 guests ∙ 3 bedrooms

House

4.6
Excellent(5 ratings)
Middlesboro, Bell County, Kentucky, United States
Pet-friendly
Details
House  Middlesboro
from $355 per night
12 guests ∙ 3 bedrooms

House

Middlesboro, Bell County, Kentucky, United States
Pet-friendly
Details
Motel  Middlesboro
from $120 per night
4 guests ∙ 1 bedroom

Motel

3.9
Good(555 ratings)
Middlesboro, Bell County, Kentucky, United States
Pet-friendly
Details
Show more

Vacation Homes With Terraces

Bed and breakfast  Middlesboro
from $158 per night
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

The Olde Mill Inn Bed & Breakfast

Middlesboro, Bell County, Kentucky, United States
Balcony/Patio
Details
Motel  Middlesboro
from $115 per night
2 guests ∙ 1 bedroom

Motel

Middlesboro, Bell County, Kentucky, United States
Balcony/Patio
Details
House  Middlesboro
from $139 per night
4 guests ∙ 2 bedrooms

House

5.0
Outstanding(8 ratings)
Middlesboro, Bell County, Kentucky, United States
Balcony/Patio
Details
Show more

Frequently Asked Questions

Can I find cheap vacation rentals in Middlesboro?

Accommodation in Middlesboro cost from $90 per night.

Is there a wide selection of vacation rentals in Middlesboro?

On tripping.com, you will find 84 available vacation rental offers in Middlesboro.

Finding the perfect vacation home has never been easier. Tripping.com searches the world's top vacation rental sites to find the best properties in 190 countries worldwide. One search lets you filter, compare and sort over 10 million available vacation rentals from trusted partners including HomeAway, VRBO, TripAdvisor, Booking.com and more. When you use Tripping.com to plan your trip and book your vacation rental, you never have to wonder if you're getting the best deal.

Vacation Rentals in Middlesboro

Looking for a vacation rental in Middlesboro? Tripping.com has 540 vacation rental homes available in Middlesboro. You'll find 0 studios, 129 1-bedroom, 37 2-bedroom and 374 rentals with 3 or more bedrooms ranging from $25 a night. For extra convenience, many of these vacation homes can be booked directly online. The average price of a nightly rental in Middlesboro is $299 while the average price of a weekly rental is $25. For those looking for more than a short term rental such as corporate rentals, extended stays or long term rentals, the average monthly price of a Middlesboro home is $25. Wondering if you can bring your dog or cat along with you? There are 77 pet-friendly vacation rentals available in Middlesboro. In addition to accommodating pets, Middlesboro rentals offer a variety of amenities. In particular, 445 rentals have Internet and WiFi, 446 have TV and/or cable and 141 have a pool or hot tub. Search properties from 6 vacation rental sites in Middlesboro where the top providers in that area are HomeAway, Expedia, and TripAdvisor. There are 365 HomeAway rentals, 102 Expedia short term rentals and 49 TripAdvisor vacation rentals.

Popular Day Trips Near Middlesboro

image-tag