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

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Check prices for these dates

In two weeks
21 Aug - 23 Aug
In two months
2 Oct - 4 Oct
In three months
30 Oct - 1 Nov
In four months
27 Nov - 29 Nov

Our top choices for Middlesboro cottages

Outdoor dining

1. The House on Park Avenue-minutes to music venues Laurel Cove and Bell Theater!

The House on Park Avenue-minutes to music venues Laurel Cove and Bell Theater!
Pineville
9.4 out of 10, Exceptional, (6 reviews)
"Such a cute little place we have stayed twice already"
United States
Cassie S.
The price is AED 694
AED 1,377 total
includes taxes & fees
8 Aug - 9 Aug
The House on Park Avenue-minutes to music venues Laurel Cove and Bell Theater!
Exterior

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

Calm Country Oasis - Creek, ATV Trls & Norris Lake
Speedwell
9.6 out of 10, Exceptional, (25 reviews)
"Clean home, responsive host, beautiful location, family friendly."
United States
Anna S.
The price is AED 400
AED 968 total
includes taxes & fees
18 Aug - 19 Aug
Calm Country Oasis - Creek, ATV Trls & Norris Lake
House (1 Bedroom) | Interior

3. 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 AED 463
AED 1,253 total
includes taxes & fees
8 Aug - 9 Aug
Peaceful Mountain Cabin w/ Views in Williamsburg
House (2 Bedrooms) | Front of property

4. Peaceful & Private! Pet-friendly Williamsburg Home

Peaceful & Private! Pet-friendly Williamsburg Home
3.0 star property
Williamsburg
The price is AED 463
AED 1,129 total
includes taxes & fees
22 Aug - 23 Aug
Peaceful & Private! Pet-friendly Williamsburg Home
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

Days Inn by Wyndham Jellico - Tennessee State Line

Days Inn by Wyndham Jellico - Tennessee State Line

8/10 Good
"No one was in office but a note was on the door - be back soon. Waited only a few minutes. Did not turn on the TV but the internet was fine. McDonalds at bottom of the hill and can be entered from motel drive, avoiding going back to the street. Did not do breakfast, can't rate it. Park in front of your door, which I like. It was comfortable."
John F 1-night trip
Posted 15 hours ago
Days Inn by Wyndham Jellico - Tennessee State Line

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