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Holiday Homes in Middlesboro

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Check prices for these dates

Next weekend
17 Oct - 19 Oct
In two weeks
24 Oct - 26 Oct
In one month
7 Nov - 9 Nov
In two months
5 Dec - 7 Dec

Featured Holiday Homes in Middlesboro and around

4.6 miles from LMU. Cozy 2-bedroom Lustron home located in Middlesboro, Ky,
2 bedrooms, iron/ironing board, free WiFi, bed sheets

4.6 miles from LMU. Cozy 2-bedroom Lustron home located in Middlesboro, Ky,

10.0 out of 10, Exceptional, (16)
"Our group had a wonderful time staying at Uncle Ernie's! Everything was neat, tidy, and felt like home. We definitely will be back next time we are in the area!"
The price is €182
includes taxes & fees
14 Oct - 15 Oct
4.6 miles from LMU. Cozy 2-bedroom Lustron home located in Middlesboro, Ky,
Welcoming 3-bedroom house with AC in charming Middlesboro
Terrace/patio

Welcoming 3-bedroom house with AC in charming Middlesboro

The price is €214
includes taxes & fees
2 Nov - 3 Nov
Welcoming 3-bedroom house with AC in charming Middlesboro
Spacious Renovated Ranch Retreat near Tackett Creek & Cumberland Gap Park, & LMU
Microwave, oven, stovetop

Spacious Renovated Ranch Retreat near Tackett Creek & Cumberland Gap Park, & LMU

The price is €515
includes taxes & fees
7 Oct - 8 Oct
Spacious Renovated Ranch Retreat near Tackett Creek & Cumberland Gap Park, & LMU
Harrogate Home Mountain View’s Dog Friendly
Fridge, microwave, oven, stovetop

Harrogate Home Mountain View’s Dog Friendly

9.8 out of 10, Exceptional, (20)
"Good space for me, my family, and my dogs to crash while we did a quick visit to the Gap."
The price is €194
includes taxes & fees
7 Oct - 8 Oct
Harrogate Home Mountain View’s Dog Friendly
Charming 3-bedroom rustic cabin with WiFi in wonderful Williamsburg
Interior

Charming 3-bedroom rustic cabin with WiFi in wonderful Williamsburg

10.0 out of 10, Exceptional, (5)
"Beautiful home. Very nice location will stay here again "
The price is €287
includes taxes & fees
7 Oct - 8 Oct
Charming 3-bedroom rustic cabin with WiFi in wonderful Williamsburg
Charming 3-bedroom house with WiFi, AC in Pineville Kentucky
Property grounds

Charming 3-bedroom house with WiFi, AC in Pineville Kentucky

10.0 out of 10, Exceptional, (1)
The price is €217
includes taxes & fees
14 Oct - 15 Oct
Charming 3-bedroom house with WiFi, AC in Pineville Kentucky
Lake Front ★ No Wake w/ Dock ★ Gameroom ★ Carved FirePit ★ 2nd House Available
Property grounds

Lake Front ★ No Wake w/ Dock ★ Gameroom ★ Carved FirePit ★ 2nd House Available

10.0 out of 10, Exceptional, (45)
"The house was beautiful and had everything we needed. The owner was very responsive to all my questions. The kids loved the game room and ping pong table."
Lake Front ★ No Wake w/ Dock ★ Gameroom ★ Carved FirePit ★ 2nd House Available
Serenity Villa: Luxurious Retreat with Hot Tub, Rooftop Deck & Mountain View's
Outdoor spa tub

Serenity Villa: Luxurious Retreat with Hot Tub, Rooftop Deck & Mountain View's

10.0 out of 10, Exceptional, (3)
"This was definitely the most romantic VRBO we’ve stayed at!!! Very clean, and the view from all of the balconies was incredible!!! "
Serenity Villa: Luxurious Retreat with Hot Tub, Rooftop Deck & Mountain View's
The House on Park Avenue
Comfort House | Private kitchen

The House on Park Avenue

3.5 star property
The price is €340
includes taxes & fees
7 Oct - 8 Oct
The House on Park Avenue
Lake Escape at Powell Valley Marina
Fridge, microwave, oven, stovetop

Lake Escape at Powell Valley Marina

9.8 out of 10, Exceptional, (7)
"We were looking for easy access to Powell Valley Marina for our family. Very clean, really decorated nicely, just a little smaller than we expected but it worked for our 4 family members. I would definitely stay there again! We took our golf cart and could access the marina quickly!! "
The price is €470
includes taxes & fees
7 Oct - 8 Oct
Lake Escape at Powell Valley Marina
1928 Home in the heart of Cumberland Gap
Exterior

1928 Home in the heart of Cumberland Gap

9.8 out of 10, Exceptional, (91)
"Prominent house in historic Cumberland Gap.Family friendly and comfortable accommodations. Lots of different seating options inside and out. We would stay here again."
The price is €223
includes taxes & fees
3 Nov - 4 Nov
1928 Home in the heart of Cumberland Gap
Charming 2-bedroom bungalow with AC, WiFi in pleasant Pineville
Living area

Charming 2-bedroom bungalow with AC, WiFi in pleasant Pineville

10.0 out of 10, Exceptional, (1)
"Well cared for property with nice upgrades! Perfect for our stay, everything we needed, and accommodating. "
The price is €236
includes taxes & fees
7 Oct - 8 Oct
Charming 2-bedroom bungalow with AC, WiFi in pleasant Pineville
3-Bedroom Cottage, Peaceful setting, Close to Parks, 2 min. from Bell Theatre
Private kitchen

3-Bedroom Cottage, Peaceful setting, Close to Parks, 2 min. from Bell Theatre

4.8 out of 10, (3)
"I did not stay at this property due to a double booking. I stayed at a nearby house that needs to be cleaned better, specially the floors, a shower curtain needs to be added to the beautiful update in bathroom, some plates woukd be nice. House rules and check in, check out procedures, places to visit and eat nearby would have been helpful to have posted at the house. Overall was a decent place to stay, quiet neighborhood. I would at least consider staying again."
The price is €208
includes taxes & fees
7 Oct - 8 Oct
3-Bedroom Cottage, Peaceful setting, Close to Parks, 2 min. from Bell Theatre
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Middlesboro Hotel Reviews

Boone Trail Inn

Boone Trail Inn

10/10 Excellent
"Fine."
Thomas 1-night trip
Posted 2 days ago
Boone Trail Inn

Find out more about Middlesboro

Find out more about Middlesboro

Middlesboro Holiday Homes information

Number of reviews
137
Accommodation
174 Holiday Homes
Lowest Price
€182
Highest Price
€515

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