Find Vacation Rentals in Middlesboro

We have 82 properties to choose from
Middlesboro
Anytime
Guests
Middlesboro
Anytime
Guests

Popular Middlesboro Vacation Rentals

Find the perfect Middlesboro vacation rental

Bed and breakfast Middlesboro
$168 per night
Bed and breakfast ∙ 6 guests ∙ 1 bedroom
5.0
Outstanding
Middlesboro, Bell County, Kentucky, United States
Details
Agoda
Details
Details
Bed and breakfast Middlesboro
$157 per night
Bed and breakfast ∙ 8 guests ∙ 1 bedroom
4.5
Excellent (394 ratings)
Middlesboro, Bell County, Kentucky, United States
Details
Expedia
Details
Details
House Middlesboro
$250 per night
House ∙ 6 guests ∙ 3 bedrooms
4.9
Outstanding (87 ratings)
Middlesboro, Bell County, Kentucky, United States
Details
Vrbo
Details
Details
Apartment Middlesboro
$111 per night
Apartment ∙ 4 guests ∙ 1 bedroom
4.9
Outstanding (19 ratings)
Middlesboro, Bell County, Kentucky, United States
Details
Vrbo
Details
Details
Cottage Middlesboro
$171 per night
Cottage ∙ 7 guests ∙ 2 bedrooms
4.5
Excellent (33 ratings)
Middlesboro, Bell County, Kentucky, United States
Details
Vrbo
Details
Details
Bed and breakfast Middlesboro
$63 per night
Bed and breakfast ∙ 2 guests ∙ 1 bedroom
4.7
Excellent (119 ratings)
Middlesboro, Bell County, Kentucky, United States
Details
HomeToGo
Details
Details
Bed and breakfast Middlesboro
$230 per night
Bed and breakfast ∙ 2 guests ∙ 1 bedroom
4.7
Excellent (119 ratings)
Middlesboro, Bell County, Kentucky, United States
Details
HomeToGo
Details
Details
Bed and breakfast Middlesboro
$215 per night
Bed and breakfast ∙ 4 guests ∙ 1 bedroom
4.7
Excellent (119 ratings)
Middlesboro, Bell County, Kentucky, United States
Details
HomeToGo
Details
Details
Bed and breakfast Middlesboro
$203 per night
Bed and breakfast ∙ 5 guests ∙ 1 bedroom
4.7
Excellent (119 ratings)
Middlesboro, Bell County, Kentucky, United States
Details
HomeToGo
Details
Details
View more

Vacation rentals and apartments with air conditioning

Motel  Middlesboro
$113 per night
Motel ∙ 8 guests ∙ 1 bedroom
4.0
Very good (541 ratings)
Middlesboro, Bell County, Kentucky, United States
Air conditioning
Details
Expedia
Details
Details
Motel  Middlesboro
$76 per night
Motel ∙ 8 guests ∙ 1 bedroom
3.6
Good (63 ratings)
Middlesboro, Bell County, Kentucky, United States
Air conditioning
Details
Expedia
Details
Details
Motel  Middlesboro
$84 per night
Motel ∙ 2 guests ∙ 1 bedroom
3.4
(50 ratings)
Middlesboro, Bell County, Kentucky, United States
Air conditioning
Details
HomeToGo
Details
Details
View more

Vacation rentals with Wi-Fi

Bed and breakfast  Middlesboro
$203 per night
Bed and breakfast ∙ 2 guests ∙ 1 bedroom
4.7
Excellent (119 ratings)
Middlesboro, Bell County, Kentucky, United States
Internet
Details
HomeToGo
Details
Details
Bed and breakfast  Middlesboro
$172 per night
Bed and breakfast ∙ 2 guests ∙ 1 bedroom
4.7
Excellent (119 ratings)
Middlesboro, Bell County, Kentucky, United States
Internet
Details
HomeToGo
Details
Details
Bed and breakfast  Middlesboro
$192 per night
Bed and breakfast ∙ 2 guests ∙ 1 bedroom
4.7
Excellent (119 ratings)
Middlesboro, Bell County, Kentucky, United States
Internet
Details
HomeToGo
Details
Details
View more

Best vacation rentals with a balcony

Motel  Middlesboro
$113 per night
Motel ∙ 2 guests ∙ 1 bedroom
3.9
Good (530 ratings)
Middlesboro, Bell County, Kentucky, United States
Balcony
Details
HomeToGo
Details
Details
Motel  Middlesboro
$198 per night
Motel ∙ 2 guests ∙ 1 bedroom
3.9
Good (530 ratings)
Middlesboro, Bell County, Kentucky, United States
Balcony
Details
HomeToGo
Details
Details
Motel  Middlesboro
$113 per night
Motel ∙ 4 guests ∙ 1 bedroom
3.9
Good (530 ratings)
Middlesboro, Bell County, Kentucky, United States
Balcony
Details
HomeToGo
Details
Details
View more

Frequently Asked Questions

Can I find cheap vacation rentals in Middlesboro?

Accommodation in Middlesboro cost from $63 per night.

Is there a wide selection of vacation rentals in Middlesboro?

On tripping.com, you will find 82 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