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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 Terrace Resort & Convention Center

River Terrace Resort & Convention Center

3.5 out of 5
Price was $534, price is now $375 per person
$375
per person
Apr 25 - Apr 27
found 2 hours ago
Roundtrip flight included
Houston (IAH) to Knoxville (TYS)
Stay at this resort 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 Oliver Hotel

The Oliver Hotel

3.5 out of 5
Save 100% on your flight
Price was $1,704, price is now $1,127 per person
$1,127
per person
May 28 - May 31
found 1 day ago
Roundtrip non-stop flight included
Houston (IAH) 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.
Hilton Knoxville

Hilton Knoxville

3.5 out of 5
Price was $1,311, price is now $1,004 per person
$1,004
per person
Apr 26 - May 2
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Knoxville (TYS)
Book a stay at this business-friendly hotel in Knoxville. Enjoy free WiFi, an outdoor pool, and room service. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Neyland Stadium and Thompson–Boling Arena are located nearby.
The Ramsey Hotel and Convention Center Pigeon Forge

The Ramsey Hotel and Convention Center Pigeon Forge

3 out of 5
Price was $904, price is now $697 per person
$697
per person
May 1 - May 4
found 1 hour ago
Roundtrip non-stop flight included
Boston (BOS) 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.
Club Wyndham Smoky Mountains

Club Wyndham Smoky Mountains

3 out of 5
Price was $1,497, price is now $1,179 per person
$1,179
per person
Jun 5 - Jun 12
found 5 hours ago
Roundtrip non-stop flight included
Boston (BOS) 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 Resort at Governor's Crossing

The Resort at Governor's Crossing

3.5 out of 5
Price was $1,048, price is now $830 per person
$830
per person
May 23 - May 30
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Knoxville (TYS)
Book a stay at this family-friendly hotel in Sevierville. Enjoy free WiFi, free parking, and free water park access. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Dollywood and Titanic Museum are located nearby.
Margaritaville Island Hotel

Margaritaville Island Hotel

4 out of 5
Price was $1,081, price is now $857 per person
$857
per person
May 6 - May 10
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Knoxville (TYS)
Book a stay at this spa hotel in Pigeon Forge. Enjoy free WiFi, a full-service spa, and room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Dollywood and Island at Pigeon Forge are located nearby.
The Lodge at Camp Margaritaville

The Lodge at Camp Margaritaville

3 out of 5
Price was $1,581, price is now $1,297 per person
$1,297
per person
Jun 5 - Jun 12
found 4 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Knoxville (TYS)
Book a stay at this family-friendly hotel in Pigeon Forge. Enjoy free WiFi, an outdoor pool, and 2 outdoor pickleball courts. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Dollywood and Dolly Parton's Stampede Dinner Attraction are located nearby.

Middlesboro Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
The Ramsey Hotel and Convention Center Pigeon Forge

The Ramsey Hotel and Convention Center Pigeon Forge

3 out of 5
Downtown Pigeon Forge
Price was $904, price is now $697 per person
$697
per person
May 1 - May 4
found 1 hour ago
Roundtrip non-stop flight included
Boston (BOS) to Knoxville (TYS)
The Oliver Hotel

The Oliver Hotel

3.5 out of 5
Downtown Knoxville
Save 100% on your flight
Price was $1,704, price is now $1,127 per person
$1,127
per person
May 28 - May 31
found 1 day ago
Roundtrip non-stop flight included
Houston (IAH) to Knoxville (TYS)
Margaritaville Island Hotel

Margaritaville Island Hotel

4 out of 5
Downtown Pigeon Forge
Price was $1,081, price is now $857 per person
$857
per person
May 6 - May 10
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Knoxville (TYS)
THE TENNESSEAN Hotel

THE TENNESSEAN Hotel

4 out of 5
Downtown Knoxville
Price was $1,065, price is now $846 per person
$846
per person
May 6 - May 10
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Knoxville (TYS)

Middlesboro Vacation Packages 5-7 Night Stays

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

Park Grove Inn

2.5 out of 5
Price was $963, price is now $714 per person
$714
per person
May 23 - May 30
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Knoxville (TYS)
The Oliver Hotel

The Oliver Hotel

3.5 out of 5
Downtown Knoxville
Save 100% on your flight
Price was $1,301, price is now $869 per person
$869
per person
Apr 26 - May 2
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Knoxville (TYS)
Hilton Knoxville

Hilton Knoxville

3.5 out of 5
Downtown Knoxville
Price was $1,311, price is now $1,004 per person
$1,004
per person
Apr 26 - May 2
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Knoxville (TYS)
River Edge Inn

River Edge Inn

2 out of 5
Downtown Gatlinburg
Price was $1,326, price is now $1,016 per person
$1,016
per person
Apr 25 - May 2
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) 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, Apr 26 - Thu, Apr 30
IAH
George Bush Intercontinental
TYS
McGhee Tyson
$186 Roundtrip, found 8 hours ago
$186
Roundtrip
found 8 hours ago
Select Frontier Airlines flight, departing Sun, Apr 26 from George Bush Intercontinental to McGhee Tyson, returning Thu, Apr 30, priced at $186 found 8 hours ago
American Airlines
Wed, May 27 - Tue, Jun 2
MCO
Orlando Intl.
TYS
McGhee Tyson
$241 Roundtrip, found 14 hours ago
$241
Roundtrip
found 14 hours ago
Select American Airlines flight, departing Wed, May 27 from Orlando Intl. to McGhee Tyson, returning Tue, Jun 2, priced at $241 found 14 hours ago
American Airlines
Wed, Apr 29 - Wed, May 6
MSY
Louis Armstrong New Orleans Intl.
TYS
McGhee Tyson
$242 Roundtrip, found 3 hours ago
$242
Roundtrip
found 3 hours ago
Select American Airlines flight, departing Wed, Apr 29 from Louis Armstrong New Orleans Intl. to McGhee Tyson, returning Wed, May 6, priced at $242 found 3 hours ago
Frontier Airlines
Sun, Apr 26 - Thu, Apr 30
LAX
Los Angeles Intl.
TYS
McGhee Tyson
$256 Roundtrip, found 1 day ago
$256
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Sun, Apr 26 from Los Angeles Intl. to McGhee Tyson, returning Thu, Apr 30, priced at $256 found 1 day ago