Search Deals onMiddlesboro Vacation Packages
Middlesboro Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Creekstone Inn
Price was $754, price is now $555 per person
$555
per person
Sep 21 - Sep 27
found 1 day ago
Roundtrip flight included
Detroit (DTW) 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 Island at Pigeon Forge are located nearby.
Quiet and clean. Lov the balcony and the creek.
Reviewed on Jul 19, 2026
River Terrace Resort & Convention Center
Save 100% on your flight
Price was $1,010, price is now $576 per person
$576
per person
Sep 21 - Sep 27
found 1 day ago
Roundtrip flight included
Detroit (DTW) 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 Ripley's Aquarium of the Smokies and Anakeesta are located nearby.
The room was older but had been remodeled. very clean. Newer AC. We were on the first level so there was no place to sit outside which was disappointing but it was easy to get to. The WiFi was not good, signal was poor.
Reviewed on Jul 18, 2026
The Ramsey Hotel and Convention Center Pigeon Forge
Save 100% on your flight
Price was $1,221, price is now $848 per person
$848
per person
Sep 21 - Sep 27
found 1 day ago
Roundtrip flight included
Detroit (DTW) 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 Island at Pigeon Forge and Dollywood are located nearby.
Clean and friendly environment overall. Mostly enjoyed the 24hr pool and large buffet style breakfast. Kids also enjoyed the poolside movie nights.
Reviewed on Jul 19, 2026
The Resort at Governor's Crossing
Save 100% on your flight
Price was $1,009, price is now $730 per person
$730
per person
Sep 21 - Sep 27
found 1 day ago
Roundtrip flight included
Detroit (DTW) 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 Titanic Museum and Island at Pigeon Forge are located nearby.
Laurel Point Resort
Price was $853, price is now $622 per person
$622
per person
Oct 13 - Oct 17
found 1 day ago
Roundtrip non-stop flight included
Houston (IAH) to Knoxville (TYS)
Stay at this aparthotel in Gatlinburg. Enjoy free WiFi, free parking, and a fitness center. Popular attractions Ripley's Aquarium of the Smokies and Great Smoky Mountains National Park are located nearby.
Great location, great room from a family of six, very clean, great amenities!
Reviewed on Jul 19, 2026
The Oliver Hotel
Save 100% on your flight
Price was $1,527, price is now $1,126 per person
$1,126
per person
Oct 8 - Oct 13
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Knoxville (TYS)
Book a stay at this business-friendly hotel in Knoxville. Enjoy free WiFi, free bicycles on site, and valet parking (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Market Square and Neyland Stadium are located nearby.
The Lodge at Camp Margaritaville
Price was $984, price is now $728 per person
$728
per person
Sep 21 - Sep 27
found 1 day ago
Roundtrip flight included
Detroit (DTW) 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 Island at Pigeon Forge are located nearby.
My kids had a blast on the waterslide. Jessica was so friendly and helped my little one so I could catch her. They played until it closed. There was something on the bed but they gave us new bedding. There were also hidden fees I didn’t know about for the amenities. Would stay again though.
Reviewed on Jul 17, 2026
Reagan Resorts Inn
Price was $802, price is now $599 per person
$599
per person
Oct 13 - Oct 17
found 1 day ago
Roundtrip non-stop flight included
Houston (IAH) to Knoxville (TYS)
Stay at this hotel in Gatlinburg. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Ripley's Aquarium of the Smokies and Anakeesta are located nearby.
Middlesboro Vacation Packages 3-4 Night Stays
Price found within the past 48 hours. Click for updated prices.
Middlesboro Vacation Packages 5-7 Night Stays
Price found within the past 48 hours. Click for updated prices.
Top Flight Deals
Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.
Mon, Sep 21 - Wed, Sep 30
MCO
Orlando Intl.
TYS
McGhee Tyson
$98 Roundtrip, found 14 hours ago
$98
Roundtrip
found 14 hours ago
Mon, Aug 10 - Mon, Aug 24
FLL
Fort Lauderdale - Hollywood Intl.
TYS
McGhee Tyson
$107 Roundtrip, found 14 hours ago
$107
Roundtrip
found 14 hours ago
Thu, Nov 26 - Wed, Dec 2
PIE
St. Petersburg-Clearwater Intl.
TYS
McGhee Tyson
$109 Roundtrip, found 14 hours ago
$109
Roundtrip
found 14 hours ago
Sat, Aug 8 - Mon, Aug 10
DFW
Dallas-Fort Worth Intl.
TYS
McGhee Tyson
$235 Roundtrip, found 4 days ago
$235
Roundtrip
found 4 days ago
Discover Other Travel Deals
- Middlesboro Country Club Vacations
- Middlesboro Mall Vacations
- Bell County Historical Society Museum Vacations
- Cumberland River Vacations
- Cumberland Gap National Historical Park Vacations
- University of the Cumberlands Vacations
- Pine Mountain State Resort Park Vacations
- Lincoln Memorial University Vacations
- Indian Mountain State Park Vacations
- Lone Mountain Boat Dock Vacations
- Straight Creek Boat Dock Vacations
- Las Vegas Vacations
- Cancun Vacations
- Miami Vacations
- Corona Vacations
- Cabo San Lucas Vacations
- Disneyland Park Vacations
- New York Vacations
- Honolulu Vacations
- Los Angeles Vacations
- Maui Vacations
- Orlando Vacations
- New Orleans Vacations
- Canada Vacations
- Tulum Vacations
- Bali Vacations
- Maldives Vacations
- Clearwater Beach Vacations
- Denver Vacations
- South Beach Vacations
- Key West Vacations
