Apartment
10.0(12 Reviews)
2 Bedrooms
4 Guests
Ocean View
View
Kitchen
Air Conditioner
US $170/Night
7 Nights - US $1,187
Middlesboro Holiday Rentals
We compare holiday rentals from owners across Booking.com, Vrbo and Expedia.
- Up-front pricing
- No markup
- Trusted partners
Compare Holiday Rentals, Villas & Resorts in Middlesboro
10.0
House
10.0(7 Reviews)
1 Bedroom
21 Guests
Parking- View
- Air Conditioner
Internet
US $254/Night
7 Nights - US $1,781
Hotel
9.6(749 Reviews)
Breakfast- Parking
Pool
Balcony/Terrace
US $158/Night
7 Nights - US $1,103
Cottage
9.4(51 Reviews)
2 Bedrooms
7 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $256/Night
7 Nights - US $1,791
Apartment
9.5(4 Reviews)
2 Bedrooms
4 Guests
- Parking
- Balcony/Terrace
- Air Conditioner
- Internet
US $142/Night
7 Nights - US $991
US $128/Night
7 Nights - US $893
House
9.8(102 Reviews)
3 Bedrooms
6 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $282/Night
7 Nights - US $1,976
House
8.0(5 Reviews)
1 Bedroom
8 Guests
- Parking
- Balcony/Terrace
- Air Conditioner
- Internet
US $189/Night
7 Nights - US $1,321
US $96/Night
7 Nights - US $672
House
9.6(42 Reviews)
3 Bedrooms
8 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $221/Night
7 Nights - US $1,547
House
1 Bedroom
10 Guests
- Internet
Pet Friendly
Security/Safety
US $323/Night
7 Nights - US $2,263
US $98/Night
7 Nights - US $688
House
10.0(19 Reviews)
4 Bedrooms
10 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $386/Night
7 Nights - US $2,701
Villa
1 Bedroom
12 Guests
- Parking
- Air Conditioner
- Internet
- Pet Friendly
US $201/Night
7 Nights - US $1,409
US $94/Night
7 Nights - US $660
House
9.2(7 Reviews)
1 Bedroom
10 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $395/Night
7 Nights - US $2,762
Hotel
9.0(308 Reviews)
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $102/Night
7 Nights - US $715
Bed & Breakfast
9.2(428 Reviews)
1 Bedroom
- Breakfast
- Parking
- Balcony/Terrace
- Internet
US $236/Night
7 Nights - US $1,653
House
8.0(3 Reviews)
1 Bedroom
10 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $346/Night
7 Nights - US $2,420
US $142/Night
7 Nights - US $992
US $111/Night
7 Nights - US $777
House
7.4(3 Reviews)
1 Bedroom
12 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $372/Night
7 Nights - US $2,604
US $95/Night
7 Nights - US $666
House
1 Bedroom
10 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $334/Night
7 Nights - US $2,338
US $80/Night
7 Nights - US $561
Apartment
9.8(28 Reviews)
1 Bedroom
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $169/Night
7 Nights - US $1,182
US $79/Night
7 Nights - US $552
House
9.0(43 Reviews)
1 Bedroom
6 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $110/Night
7 Nights - US $770
House
8.8(25 Reviews)
5 Bedrooms
14 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $608/Night
7 Nights - US $4,258
House
10.0(33 Reviews)
2 Bedrooms
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $203/Night
7 Nights - US $1,420
House
9.8(6 Reviews)
4 Bedrooms
8 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $273/Night
7 Nights - US $1,910
House
5.0(5 Reviews)
5 Bedrooms
12 Guests
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
US $500/Night
7 Nights - US $3,500
House
4.9(17 Reviews)
3 Bedrooms
10 Guests
- Kitchen
- Air Conditioner
- Internet
- Pet Friendly
US $177/Night
7 Nights - US $1,239
House
5.0(1 Review)
8 Bedrooms
22 Guests
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Pet Friendly
US $1,000/Night
7 Nights - US $7,000
House
3 Bedrooms
7 Guests
- Air Conditioner
- Internet
Bedding/Linens
Designated Smoking Area
US $140/Night
7 Nights - US $977
About Casai's Private Villas and Holiday Rentals in Middlesboro
Discover more than 35 vacation rentals available in Middlesboro. These rentals, ranging from vacation rentals to Casai Homes and other short-term private accommodations, offer top-notch amenities with unbeatable value, ensuring both comfort and luxury. Enjoy more space and value when you stay at a Casai property in Middlesboro.
Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Middlesboro, you can effortlessly compare various deals with just a click. Whether you're looking for a Casai with exceptional swimming pools, hot tubs, pet-friendly options, or large master suite bedrooms equipped with large screen televisions, you'll find a variety of options near Middlesboro. On average, places to stay near Middlesboro offer 2028.26 ft², with nightly prices averaging US $242.
With Casai, finding and comparing holiday rentals in Middlesboro is easy and secure, often at a 30-40% discount compared to hotel prices. Simply search for your destination and secure your reservation today.
Other Places to Stay in Middlesboro, KY
There are 35 Middlesboro, KY Vacation Rentals
- Prices for a holiday home in Middlesboro start at US $79
- Top rated vacation home in Middlesboro is Gorgeous 4-bedroom house in Middlesboro KY with WiFi, AC. Minutes from LMU
- Most popular short term in Middlesboro is Sleep Inn & Suites Middlesboro
- Cheapest place to stay in Middlesboro is Boone trail inn
- Most expensive holiday rental in Middlesboro is Charming 3-bedroom house in the Crater City near State Parks, LMU, & hospitals.
Recently Booked Hotels, Resorts, or Rentals in Middlesboro
Frequently Asked Questions About Middlesboro?
What are the top holiday rentals in Middlesboro?
With numerous options available in Middlesboro, planning to stay in the area? Consider booking a few nights at one of these properties, rated as the Top Holiday Rentals in Middlesboro:
- Gorgeous 4-bedroom house in Middlesboro KY with WiFi, AC. Minutes from 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
- 1928 Home in the heart of Cumberland Gap
- Holiday Inn Express Middlesboro by IHG
- Blissful Bungalow across from LMU campus
- Mountain View Retreat 5 min to LMU
- Cozy Cumberland Gap Cottage Near LMU & Nat’l Park
- Sleep Inn & Suites Middlesboro
- Charming 3-bedroom house in the Crater City near State Parks, LMU, & hospitals.
How many Casai.nz holiday rentals are available in Middlesboro?
As of 2026, Casai boasts over 35 properties listed in the Middlesboro area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Middlesboro.
