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Middlesboro Vacation Packages

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Middlesboro Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
River Edge Inn

River Edge Inn

2 out of 5
Price was $633, price is now $437 per person
$437
per person
May 29 - Jun 2
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Knoxville (TYS)
Stay at this hotel in Gatlinburg. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Great Smoky Mountains National Park and Dollywood are located nearby.
The Ramsey Hotel and Convention Center Pigeon Forge

The Ramsey Hotel and Convention Center Pigeon Forge

3 out of 5
Save 100% on your flight
Price was $1,090, price is now $720 per person
$720
per person
May 25 - Jun 1
found 24 hours ago
Roundtrip flight included
Chicago (ORD) to Knoxville (TYS)
Book a stay at this business-friendly hotel in Pigeon Forge. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Dollywood and Ripley's Aquarium of the Smokies are located nearby.
Sleeps 16 2 Cabins w/ Game Room, Hot Tub & Views Perfect & Perfect Too

Sleeps 16 2 Cabins w/ Game Room, Hot Tub & Views Perfect & Perfect Too

3 out of 5
Save 100% on your flight
Price was $3,868, price is now $2,653 per person
$2,653
per person
May 25 - Jun 1
found 24 hours ago
Roundtrip flight included
Chicago (ORD) to Knoxville (TYS)
Stay at this cottage in Gatlinburg. Enjoy free parking, a pool table, and patios. Popular attractions Ripley's Aquarium of the Smokies and Great Smoky Mountains National Park are located nearby.
Creekstone Inn

Creekstone Inn

2 out of 5
Price was $815, price is now $567 per person
$567
per person
May 25 - Jun 1
found 24 hours ago
Roundtrip flight included
Chicago (ORD) to Knoxville (TYS)
Stay at this hotel in Pigeon Forge. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Dollywood and Ripley's Aquarium of the Smokies are located nearby.
Club Wyndham Smoky Mountains

Club Wyndham Smoky Mountains

3 out of 5
Save 100% on your flight
Price was $1,284, price is now $921 per person
$921
per person
May 25 - Jun 1
found 24 hours ago
Roundtrip flight included
Chicago (ORD) to Knoxville (TYS)
Book a stay at this family-friendly hotel in Sevierville. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Dollywood and Titanic Museum are located nearby.
The Oliver Hotel

The Oliver Hotel

3.5 out of 5
Price was $1,252, price is now $903 per person
$903
per person
May 21 - May 24
found 4 hours ago
Roundtrip flight included
Chicago (ORD) to Knoxville (TYS)
Book a stay at this business-friendly hotel in Knoxville. Enjoy free WiFi, a fitness center, and valet parking (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Neyland Stadium and Thompson–Boling Arena are located nearby.
Fireflies and Moonshine

Fireflies and Moonshine

3.5 out of 5
Save 100% on your flight
Price was $1,649, price is now $1,205 per person
$1,205
per person
May 21 - May 26
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Knoxville (TYS)
Stay at this chalet in Gatlinburg. Enjoy free WiFi, free parking, and laundry facilities. Popular attractions Dollywood and Wild Bear Falls Indoor Water Park are located nearby.
Hot Tub, Game Room & Views Near Downtown Gatlinburg Perfect Too by Avantstay

Hot Tub, Game Room & Views Near Downtown Gatlinburg Perfect Too by Avantstay

3 out of 5
Save 100% on your flight
Price was $2,251, price is now $1,671 per person
$1,671
per person
May 25 - Jun 1
found 24 hours ago
Roundtrip flight included
Chicago (ORD) to Knoxville (TYS)
Enjoy free parking, a pool table, and patios. Popular attractions Great Smoky Mountains National Park and Dollywood are located nearby.

Middlesboro Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
River Edge Inn

River Edge Inn

2 out of 5
Downtown Gatlinburg
Price was $633, price is now $437 per person
$437
per person
May 29 - Jun 2
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Knoxville (TYS)
The Oliver Hotel

The Oliver Hotel

3.5 out of 5
Downtown Knoxville
Price was $1,252, price is now $903 per person
$903
per person
May 21 - May 24
found 4 hours ago
Roundtrip flight included
Chicago (ORD) to Knoxville (TYS)
The Historic Gatlinburg Inn

The Historic Gatlinburg Inn

2.5 out of 5
Downtown Gatlinburg
Price was $707, price is now $537 per person
$537
per person
May 29 - Jun 2
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Knoxville (TYS)
Park Grove Inn

Park Grove Inn

2.5 out of 5
Price was $802, price is now $611 per person
$611
per person
Apr 16 - Apr 19
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) to Knoxville (TYS)

Middlesboro Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
Creekstone Inn

Creekstone Inn

2 out of 5
Price was $815, price is now $567 per person
$567
per person
May 25 - Jun 1
found 24 hours ago
Roundtrip flight included
Chicago (ORD) to Knoxville (TYS)
The Ramsey Hotel and Convention Center Pigeon Forge

The Ramsey Hotel and Convention Center Pigeon Forge

3 out of 5
Downtown Pigeon Forge
Save 100% on your flight
Price was $1,090, price is now $720 per person
$720
per person
May 25 - Jun 1
found 24 hours ago
Roundtrip flight included
Chicago (ORD) to Knoxville (TYS)
River Edge Inn

River Edge Inn

2 out of 5
Downtown Gatlinburg
Save 100% on your flight
Price was $1,056, price is now $707 per person
$707
per person
May 21 - May 26
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Knoxville (TYS)
Sleeps 16 2 Cabins w/ Game Room, Hot Tub & Views Perfect & Perfect Too

Sleeps 16 2 Cabins w/ Game Room, Hot Tub & Views Perfect & Perfect Too

3 out of 5
Save 100% on your flight
Price was $3,868, price is now $2,653 per person
$2,653
per person
May 25 - Jun 1
found 24 hours ago
Roundtrip flight included
Chicago (ORD) to Knoxville (TYS)

Top Flight Deals

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Frontier Airlines
Sun, May 3 - Mon, May 11
TPA
Tampa Intl.
TYS
McGhee Tyson
$201 Roundtrip, found 12 hours ago
$201
Roundtrip
found 12 hours ago
Select Frontier Airlines flight, departing Sun, May 3 from Tampa Intl. to McGhee Tyson, returning Mon, May 11, priced at $201 found 12 hours ago
Frontier Airlines
Sun, Apr 26 - Thu, Apr 30
IAH
George Bush Intercontinental
TYS
McGhee Tyson
$232 Roundtrip, found 12 hours ago
$232
Roundtrip
found 12 hours ago
Select Frontier Airlines flight, departing Sun, Apr 26 from George Bush Intercontinental to McGhee Tyson, returning Thu, Apr 30, priced at $232 found 12 hours ago
American Airlines
Wed, Apr 8 - Thu, Apr 16
MCO
Orlando Intl.
TYS
McGhee Tyson
$243 Roundtrip, found 5 days ago
$243
Roundtrip
found 5 days ago
Select American Airlines flight, departing Wed, Apr 8 from Orlando Intl. to McGhee Tyson, returning Thu, Apr 16, priced at $243 found 5 days ago
Frontier Airlines
Mon, Apr 6 - Thu, Apr 16
LAX
Los Angeles Intl.
TYS
McGhee Tyson
$255 Roundtrip, found 1 day ago
$255
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Mon, Apr 6 from Los Angeles Intl. to McGhee Tyson, returning Thu, Apr 16, priced at $255 found 1 day ago