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Our top choices for Middlesboro cottages

1. Cozy Cumberland Gap Cottage Near LMU & Nat’l Park

Cozy Cumberland Gap Cottage Near LMU & Nat’l Park
Cumberland Gap
9.4 out of 10, Exceptional, (52 reviews)
"The house was nice and clean and ready for us. When we checked in, the location was absolutely perfect from downtown, Everything worked out the way it should be. If we go back to Cumberland Gap, which I hope we will we will try to stay in the same location."
United States
JOHN H.
$181 nightly
The price is $203
Nov 19 - Nov 20
Total with taxes and fees
Cozy Cumberland Gap Cottage Near LMU & Nat’l Park

2. Peaceful & Private! Pet-friendly Williamsburg Home

Peaceful & Private! Pet-friendly Williamsburg Home
3.0 star property
Williamsburg
$279 nightly
The price is $307
Nov 7 - Nov 8
Total with taxes and fees
Peaceful & Private! Pet-friendly Williamsburg Home

3. Calm Country Oasis - Creek, ATV Trls & Norris Lake

Calm Country Oasis - Creek, ATV Trls & Norris Lake
Speedwell
9.6 out of 10, Exceptional, (29 reviews)
"Loved the creek and inside decor. Roomy house!"
United States
Sandra
$224 nightly
The price is $249
Nov 29 - Nov 30
Total with taxes and fees
Calm Country Oasis - Creek, ATV Trls & Norris Lake

4. Robertson Ridge Hideaway Cottage

Robertson Ridge Hideaway Cottage
Hinkle
10.0 out of 10, Exceptional, (4 reviews)
"Beautiful place "
United States
Isaac L.
$137 nightly
The price is $150
Nov 16 - Nov 17
Total with taxes and fees
Robertson Ridge Hideaway Cottage

5. Peaceful Mountain Cabin w/ Views in Williamsburg

Peaceful Mountain Cabin w/ Views in Williamsburg
2.0 star property
Williamsburg
2.0 out of 10, (1 review)
"The owners were very polite. The only issue I had was that the listing online did not say anything about it being fully solar powered with no electricity. We left in the middle of the night the first night because there was no power at all."
United States
Chandler
$310 nightly
The price is $341
Nov 7 - Nov 8
Total with taxes and fees
Peaceful Mountain Cabin w/ Views in Williamsburg

6. Studio 8 Mi to Norris Lake! Couples & Pets Welcome

Studio 8 Mi to Norris Lake! Couples & Pets Welcome
3.0 star property
Tazewell
$218 nightly
The price is $245
Nov 7 - Nov 8
Total with taxes and fees
Studio 8 Mi to Norris Lake! Couples & Pets Welcome
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.

Learn more about Middlesboro

Nestled in the Appalachian Mountains, Middlesboro invites you to explore the historic Cumberland Gap National Historical Park. Tee off at the scenic Middlesboro Country Club or delve into local heritage at the Bell County Historical Society Museum.

An aerial view of a town surrounded by mountains, with a mix of residential and commercial buildings, and a highway running through the center.

Top reviews in Middlesboro

Frequently Asked Questions

Why book your cottage in Middlesboro with Expedia?

We think that a vacation should be hassle-free, so if you're searching for cottages in Middlesboro at a great price, Expedia has your back. Keep the budget under control and stay in an inexpensive option surrounded by nature, or splurge on a 5-star cottage to spoil your favorite people.

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What is there to do in Middlesboro near my cottage?

The most useful travel accessory is a well-planned to-do list. Middlesboro Mall is a wonderful place to begin your adventures in Middlesboro.

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