Search Middlesboro Cottage Rentals from CA $138

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Check prices for these dates

Next weekend
Nov 13 - Nov 15
In two weeks
Nov 20 - Nov 22
In one month
Dec 4 - Dec 6
In two months
Jan 1 - Jan 3

Our top choices for Middlesboro cottages

A single-story house with a porch, a mailbox, and a small garden.

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.
The price is CA $138
CA $287 total
includes taxes & fees
Nov 19 - Nov 20
Cozy Cumberland Gap Cottage Near LMU & Nat’l Park
A covered outdoor deck with wooden flooring and metal chairs.

2. Peaceful & Private! Pet-friendly Williamsburg Home

Peaceful & Private! Pet-friendly Williamsburg Home
3.0 star property
Williamsburg
The price is CA $176
CA $430 total
includes taxes & fees
Nov 7 - Nov 8
Peaceful & Private! Pet-friendly Williamsburg Home
A single-story house with a front porch, a large window, and a well-maintained lawn.

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
The price is CA $153
CA $353 total
includes taxes & fees
Nov 29 - Nov 30
Calm Country Oasis - Creek, ATV Trls & Norris Lake
Exterior

4. Robertson Ridge Hideaway Cottage

Robertson Ridge Hideaway Cottage
Hinkle
10.0 out of 10, Exceptional, (4 reviews)
"Beautiful place "
United States
Isaac L.
The price is CA $170
CA $210 total
includes taxes & fees
Nov 16 - Nov 17
Robertson Ridge Hideaway Cottage
A wooden cabin with a covered porch, furnished with wicker chairs and a glass table.

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
The price is CA $176
CA $477 total
includes taxes & fees
Nov 7 - Nov 8
Peaceful Mountain Cabin w/ Views in Williamsburg
A rural landscape with a small wooden house, a gravel path, and a forested hill in the background.

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

Studio 8 Mi to Norris Lake! Couples & Pets Welcome
3.0 star property
Tazewell
The price is CA $168
CA $342 total
includes taxes & fees
Nov 7 - Nov 8
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.
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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.

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

Frequently Asked Questions

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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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