Find Vacation Rentals in Middlesboro

We have 78 properties to choose from
Middlesboro
Anytime
Guests

Popular Middlesboro Vacation Rentals

Find the perfect Middlesboro vacation rental

Motel Middlesboro
$108 per night
Motel ∙ 4 guests ∙ 1 bedroom
3.4
(372 ratings)
Middlesboro, Bell County, Kentucky, United States
Details
HomeToGo
Details
Details
Cottage Middlesboro
$132 per night
Cottage ∙ 6 guests ∙ 2 bedrooms
4.6
Excellent (21 ratings)
Middlesboro, Bell County, Kentucky, United States
Details
Vrbo
Details
Details
Apartment Middlesboro
$128 per night
Apartment ∙ 4 guests ∙ 1 bedroom
5.0
Outstanding (6 ratings)
Middlesboro, Bell County, Kentucky, United States
Details
Vrbo
Details
Details
Bed and breakfast Middlesboro
$169 per night
Bed and breakfast ∙ 2 guests ∙ 1 bedroom
4.8
Outstanding (155 ratings)
Middlesboro, Bell County, Kentucky, United States
Details
HomeToGo
Details
Details
Bed and breakfast Middlesboro
$223 per night
Bed and breakfast ∙ 2 guests ∙ 1 bedroom
4.8
Outstanding (155 ratings)
Middlesboro, Bell County, Kentucky, United States
Details
HomeToGo
Details
Details
Bed and breakfast Middlesboro
$169 per night
Bed and breakfast ∙ 2 guests ∙ 1 bedroom
4.8
Outstanding (155 ratings)
Middlesboro, Bell County, Kentucky, United States
Details
HomeToGo
Details
Details
Bed and breakfast Middlesboro
$205 per night
Bed and breakfast ∙ 2 guests ∙ 1 bedroom
4.8
Outstanding (155 ratings)
Middlesboro, Bell County, Kentucky, United States
Details
HomeToGo
Details
Details
Bed and breakfast Middlesboro
$192 per night
Bed and breakfast ∙ 2 guests ∙ 1 bedroom
4.8
Outstanding (155 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
4.8
Outstanding (155 ratings)
Middlesboro, Bell County, Kentucky, United States
Details
HomeToGo
Details
Details
View more

Recommended Rentals With Pools

Motel  Middlesboro
$68 per night
Motel ∙ 4 guests ∙ 1 bedroom
3.2
(53 ratings)
Middlesboro, Bell County, Kentucky, United States
Pool
Details
HomeToGo
Details
Details
Motel  Middlesboro
$102 per night
Motel ∙ 4 guests ∙ 1 bedroom
3.4
(372 ratings)
Middlesboro, Bell County, Kentucky, United States
Pool
Details
HomeToGo
Details
Details
Motel  Middlesboro
$108 per night
Motel ∙ 4 guests ∙ 1 bedroom
3.4
(372 ratings)
Middlesboro, Bell County, Kentucky, United States
Pool
Details
HomeToGo
Details
Details
View more

Best vacation rentals with a balcony

House  Middlesboro
$599 per night
House ∙ 12 guests ∙ 5 bedrooms
5.0
Outstanding (6 ratings)
Middlesboro, Bell County, Kentucky, United States
Balcony
Details
Vrbo
Details
Details
Motel  Middlesboro
$192 per night
Motel ∙ 2 guests ∙ 1 bedroom
4.0
Very good (597 ratings)
Middlesboro, Bell County, Kentucky, United States
Balcony
Details
HomeToGo
Details
Details
View more

Vacation Homes With Terraces

House  Middlesboro
$168 per night
House ∙ 8 guests ∙ 3 bedrooms
5.0
Outstanding (12 ratings)
Middlesboro, Bell County, Kentucky, United States
Balcony/Patio
Details
Vrbo
Details
Details
View more

Frequently Asked Questions

Can I find cheap vacation rentals in Middlesboro?

Accommodation in Middlesboro cost from $68 per night.

Is there a wide selection of vacation rentals in Middlesboro?

On tripping.com, you will find 78 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

Show more
image-tag