---
title: "Middlesboro Vacation Packages & Trips 2026 from CA $1,690 | Expedia"
description: "FREE cancellation on select hotels Bundle Middlesboro flight and hotel to build your own Middlesboro vacation package & you can 𝘀𝗮𝘃𝗲 with Expedia! Choose from thousands of Middlesboro holiday trips & travel deals."
canonical: "https://www.expedia.ca/Middlesboro.d8853.Destination-Travel-Guides"
language: en-CA
market: CA
currency: CAD
prices_as_of: 2026-11-15T02:45:07Z
---

# Middlesboro Vacation Packages
![An aerial view of a town surrounded by mountains, with a mix of residential and commercial buildings, and a highway running through the center.](https://images.trvl-media.com/place/8853/4dcad675-90c8-4311-844e-cc929dfd2557.jpg?impolicy=fcrop&w=1200&h=300&q=medium)

## Book a Hotel + Flight or Car together to unlock savings

- ## Plan, book, travel with confidence
- ### Better together
Save up to CA $4,200 when you book a flight and hotel together\*
- ### Find the right fit
With over 300,000 hotels worldwide, it's easy to create a perfect package
- ### Rest easy
Plan, book, and manage your trip all in one place

#### Your Middlesboro Vacation

From its rich history to its spectacular views and beyond, there's a lot to like about Middlesboro. Discover the wonders of this interesting city with a Middlesboro vacation package that's made for you. If taking in sights is on the agenda during your trip to Middlesboro, check out popular attractions like [Cumberland Gap National Historical Park](https://www.expedia.ca/Cumberland-Gap-National-Historical-Park-Ewing.d6091497.Vacation-Attraction), [Middlesboro Mall](https://www.expedia.ca/Middlesboro-Mall-Middlesboro.d553248621561234928.Vacation-Attraction) and [Bell County Historical Society Museum](https://www.expedia.ca/Bell-County-Historical-Society-Museum-Middlesboro.d553248621561234927.Vacation-Attraction). Your ideal Middlesboro vacation is just clicks away. Browse accommodations, flights and more on Expedia for an adventure that's tailored to suit your travel style.

## Top Middlesboro vacation deals

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

Trip length

3 nights4 nights5 nights6-7 nights

Stars

5 star4 star & up3 star & up2 star & up

Flight class

EconomyPremium economyBusinessFirst class

Remove all filters

- ![A spacious room with large windows, wooden flooring, and a high ceiling.](https://images.trvl-media.com/lodging/5000000/4980000/4978700/4978639/b3824846.jpg?impolicy=fcrop&w=500&h=333&p=1&q=medium)
![A bear enclosure with a stone wall and metal railing.](https://images.trvl-media.com/lodging/5000000/4980000/4978700/4978639/96194a02.jpg?impolicy=fcrop&w=500&h=333&p=1&q=medium)

**Dec 26 - Jan 1**

### [Brookside Lodge + Flight](https://www.expedia.ca/go/package/search/FlightHotel/2026-12-26/2027-01-01/?FromAirport=YTO&Destination=TYS&NumRoom=1&NumAdult=2&NumChild=0&hotelId=4978639&dealMarker=&paandie=true&cabinClass=e)
Gatlinburg
6 nights

**8.6/10** \- Excellent (2,359 reviews)
Roundtrip • Toronto (YTO) - Knoxville (TYS)
YYZ - TYS • 1 stop TYS - YYZ • 1 stop
[~~CA $2,159~~](https://www.expedia.ca/)

**CA $1,690**
per traveller
found 1 day ago
- ![A rooftop bar with outdoor seating, a bar area, and a view of a forested hill.](https://images.trvl-media.com/lodging/120000000/119740000/119739400/119739309/dc2df088.jpg?impolicy=fcrop&w=500&h=333&p=1&q=medium)
![A modern restaurant with large windows, wooden floors, and unique spherical hanging lights.](https://images.trvl-media.com/lodging/120000000/119740000/119739400/119739309/78e15434.jpg?impolicy=fcrop&w=500&h=333&p=1&q=medium)

**Dec 26 - Jan 1**

### [Hotel Indigo Gatlinburg Downtown by IHG + Flight](https://www.expedia.ca/go/package/search/FlightHotel/2026-12-26/2027-01-01/?FromAirport=YTO&Destination=TYS&NumRoom=1&NumAdult=2&NumChild=0&hotelId=119739309&dealMarker=&paandie=true&cabinClass=e)
Downtown Gatlinburg
6 nights

**9.6/10** \- Exceptional (880 reviews)
"Great location, wonderful staff!"
Reviewed November 15, 2026
Roundtrip • Toronto (YTO) - Knoxville (TYS)
YYZ - TYS • 1 stop TYS - YYZ • 1 stop
[~~CA $2,714~~](https://www.expedia.ca/)

**CA $1,950**
per traveller
found 1 day ago
- ![A modern bathroom with a large bathtub, a shower area, and a window providing a view of greenery.](https://images.trvl-media.com/lodging/1000000/180000/172600/172522/27d7bc2d.jpg?impolicy=fcrop&w=500&h=333&p=1&q=medium)
![A hotel lobby with a large window offering a view of a mountain and a sign for Reagan Resorts.](https://images.trvl-media.com/lodging/1000000/180000/172600/172522/d21f3da1.jpg?impolicy=fcrop&w=500&h=333&p=1&q=medium)

**Dec 26 - Jan 1**

### [Reagan Resorts Inn + Flight](https://www.expedia.ca/go/package/search/FlightHotel/2026-12-26/2027-01-01/?FromAirport=YTO&Destination=TYS&NumRoom=1&NumAdult=2&NumChild=0&hotelId=172522&dealMarker=&paandie=true&cabinClass=e)
Downtown Gatlinburg
6 nights

**8.6/10** \- Excellent (1,771 reviews)
"Very clean and great location"
Reviewed November 14, 2026
Roundtrip • Toronto (YTO) - Knoxville (TYS)
YYZ - TYS • 1 stop TYS - YYZ • 1 stop
[~~CA $2,339~~](https://www.expedia.ca/)

**CA $1,754**
per traveller
found 1 day ago
- ![A deck with outdoor seating and a fire feature.](https://images.trvl-media.com/lodging/136000000/135480000/135478400/135478350/417156b1.jpg?impolicy=fcrop&w=500&h=333&p=1&q=medium)
![A large hotel complex with multiple buildings, a parking area, and a tennis court.](https://images.trvl-media.com/lodging/136000000/135480000/135478400/135478350/ce8ec77c.jpg?impolicy=fcrop&w=500&h=333&p=1&q=medium)

**Dec 26 - Jan 1**

### [Bear Ridge by Avantstay Smoky Views + Indoor Pool + Sauna & Spa Near Park Trails + Flight](https://www.expedia.ca/go/package/search/FlightHotel/2026-12-26/2027-01-01/?FromAirport=YTO&Destination=TYS&NumRoom=1&NumAdult=2&NumChild=0&hotelId=135478350&dealMarker=&paandie=true&cabinClass=e)
Gatlinburg
6 nights
Roundtrip • Toronto (YTO) - Knoxville (TYS)
YYZ - TYS • 1 stop TYS - YYZ • 1 stop
[~~CA $3,079~~](https://www.expedia.ca/)

**CA $2,479**
per traveller
found 1 day ago
- ![A deck with outdoor seating and a fire feature.](https://images.trvl-media.com/lodging/136000000/135480000/135478300/135478238/7a8473e7.jpg?impolicy=fcrop&w=500&h=333&p=1&q=medium)
![A large hotel complex with multiple buildings, a parking area, and a tennis court.](https://images.trvl-media.com/lodging/136000000/135480000/135478300/135478238/d67f68c2.jpg?impolicy=fcrop&w=500&h=333&p=1&q=medium)

**Dec 26 - Jan 1**

### [Lazy Bear by Avantstay Mountain Views + Indoor Pool + Hot Tub Access + Courts Near National Park + Flight](https://www.expedia.ca/go/package/search/FlightHotel/2026-12-26/2027-01-01/?FromAirport=YTO&Destination=TYS&NumRoom=1&NumAdult=2&NumChild=0&hotelId=135478238&dealMarker=&paandie=true&cabinClass=e)
Gatlinburg
6 nights
Roundtrip • Toronto (YTO) - Knoxville (TYS)
YYZ - TYS • 1 stop TYS - YYZ • 1 stop
[~~CA $2,928~~](https://www.expedia.ca/)

**CA $2,382**
per traveller
found 1 day ago

## Discover the most popular places to visit in Middlesboro

### Middlesboro Country Club

Enjoy a round of golf in Middlesboro at Middlesboro Country Club. Discover the mountain views while you're in the area.

[See properties](https://www.expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests&regionId=814064404147970048)

### Bell County Historical Society Museum

Rating: 8.2/10 (13 reviews)

You can spend an afternoon exploring the galleries in Bell County Historical Society Museum during your travels in Middlesboro. Discover the mountain views while you're in the area.

[See properties](https://www.expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests&regionId=553248621561234927)

### Middlesboro Mall

Rating: 7.6/10 (62 reviews)

You can search for that perfect souvenir at Middlesboro Mall during your visit to Middlesboro. Discover the mountain views while you're in the area.

[See properties](https://www.expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests&regionId=553248621561234928)

## Middlesboro Hotel Deals

### [Holiday Inn Express Middlesboro by IHG](https://www.expedia.ca/Middlesboro-Hotels-Holiday-Inn-Express-Middlesboro.h60850.Hotel-Information)

![A hotel entrance with a covered walkway, potted plants, and a reception area.](https://images.trvl-media.com/lodging/1000000/70000/60900/60850/406e916d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Address: 1252 N 12th St, Middlesboro, KY, 40965, US
- Location: 1.9 km from Middlesboro
- Star rating: 2.5/5
- Guest rating: 9.6/10 (Exceptional, 751 reviews)
- Price: CA $176, CA $193 total, includes taxes & fees, Dec 13 - Dec 14

### [Sleep Inn & Suites Middlesboro](https://www.expedia.ca/Middlesboro-Hotels-Sleep-Inn-Suites.h3929546.Hotel-Information)

![A hotel room with a sofa, a coffee table, a bed with a canopy, a TV, and artwork on the walls.](https://images.trvl-media.com/lodging/4000000/3930000/3929600/3929546/86beaca2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Address: 1260 N, 12th Street, Middlesboro, KY, 40965, US
- Location: 2.3 km from Middlesboro
- Star rating: 2.5/5
- Guest rating: 9.2/10 (Wonderful, 958 reviews)
- Price: CA $141, CA $158 total, includes taxes & fees, Dec 6 - Dec 7
- Review: Very friendly staff

### [Econo Lodge Middlesboro](https://www.expedia.ca/Middlesboro-Hotels-Econo-Lodge.h15146.Hotel-Information)

![A hotel room with two beds, a sofa, a nightstand with a lamp, and a framed picture on the wall.](https://images.trvl-media.com/lodging/1000000/20000/15200/15146/79102e17.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Address: 1623 Cumberland Avenue, Middlesboro, KY, 40965, US
- Location: 0.8 km from Middlesboro
- Star rating: 2/5
- Guest rating: 7.4/10 (Good, 511 reviews)
- Price: CA $114, CA $126 total, includes taxes & fees, Nov 22 - Nov 23

### [Suburban Studios Middlesboro](https://www.expedia.ca/Middlesboro-Hotels-Suburban-Extended-Stay-Hotel.h69390006.Hotel-Information)

![A hotel room with a large bed, two bedside tables with lamps, a desk with a chair, a television, and a bathroom visible through an open door.](https://images.trvl-media.com/lodging/70000000/69400000/69390100/69390006/4f60a168.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Address: 1623 Cumberland Avenue Building B, Middlesboro, KY, 40965, US
- Location: 0.7 km from Middlesboro
- Star rating: 2/5
- Guest rating: 8.4/10 (Very good, 123 reviews)
- Price: CA $103, CA $114 total, includes taxes & fees, Dec 5 - Dec 6
- Review: Not well insulated and neighbors & dogs very loud.

### [Boone Trail Inn](https://www.expedia.ca/Middlesboro-Hotels-Boone-Trail-Inn.h34978817.Hotel-Information)

![A white portable air conditioner mounted on a wall with a control panel, a power outlet, and a plastic bag hanging from the bottom.](https://images.trvl-media.com/lodging/35000000/34980000/34978900/34978817/731be73a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Address: 2105 US HIGHWAY 25 E, Middlesboro, KY, 40965, US
- Location: 2.9 km from Middlesboro
- Star rating: 2/5
- Guest rating: 7.4/10 (Good, 127 reviews)
- Price: CA $111, CA $138 total, includes taxes & fees, Nov 16 - Nov 17

### [Pine Mountain State Resort Park](https://www.expedia.ca/Corbin-Hotels-Pine-Mountain-State-Resort-Park.h1109434.Hotel-Information)

![A natural setting with a clear pond surrounded by rocks and trees, and rows of blue chairs arranged for an event.](https://images.trvl-media.com/lodging/2000000/1110000/1109500/1109434/75b8d155.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Address: 1050 State Park Road, Pineville, KY, 40977, US
- Location: 15.5 km from Middlesboro
- Star rating: 3/5
- Guest rating: 9/10 (Wonderful, 785 reviews)
- Price: CA $137, CA $151 total, includes taxes & fees, Dec 10 - Dec 11
- Review: Great stay for nature lovers. Balcony nice feature.

### [Imperial Inn Tazewell](https://www.expedia.ca/Tazewell-Hotels-Imperial-Inn-Tazewell.h113960224.Hotel-Information)

![A bedroom with a bed, a TV, a desk, and a chair.](https://images.trvl-media.com/lodging/114000000/113970000/113960300/113960224/f7338edd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Address: 2196 Highway 25E, Tazewell, TN, 37879, US
- Location: 20.5 km from Middlesboro
- Star rating: 2.5/5
- Guest rating: 8.8/10 (Excellent, 97 reviews)
- Price: CA $111, CA $129 total, includes taxes & fees, Nov 16 - Nov 17
- Review: This is our go to spot for staying in Tazwell. The rooms are newly remodeled and clean and the staff is always kind and polite.

### [Holiday Inn Express Williamsburg by IHG](https://www.expedia.ca/Corbin-Hotels-Holiday-Inn-Express-Williamsburg.h23240809.Hotel-Information)

![A hotel entrance with a covered parking area, stone pillars, and a blue-lit facade.](https://images.trvl-media.com/lodging/24000000/23250000/23240900/23240809/21b9e921.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Address: 56 West Highway 92, Williamsburg, KY, 40769, US
- Location: 41.9 km from Middlesboro
- Star rating: 2.5/5
- Guest rating: 9/10 (Wonderful, 1001 reviews)
- Price: CA $168, CA $187 total, includes taxes & fees, Nov 22 - Nov 23
- Review: "The location of this property is very good and easy to access. Room was spacious and well-equipped except for a coffee maker. Our room happened to be just above the roof top for the front entrance leaving an unattractive view. Also, the darker shade on the window would not close leaving the room well-lit all night from bright lights outside. And cars turning at an intersection not far away had their headlights aimed directly at the window, which was a little annoying. The best part of our...

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.

[See all properties in Middlesboro](https://www.expedia.ca/Hotel-Search?startDate=2026-11-29&endDate=2026-11-30&regionId=8853&adults=2&sort=RECOMMENDED&openPlayBack=true)

## Frequently Asked Questions

### How much does a Middlesboro vacation package cost?

You'll find cheap prices from CA $1,690 on Expedia for your Middlesboro getaway. However, factors like the hotel choice, length of stay and season will influence how much your vacation to Middlesboro costs.

### What are the cheapest months to go to Middlesboro?

You can usually find reduced prices and better availability in January, February and November. Check out our cheap Middlesboro vacation packages and you could score some excellent off-season deals.

### How many days is enough for Middlesboro?

With a well-planned schedule, you can easily visit the main Middlesboro sights in a handful of days. But if you'd like to discover lesser-known spots or take day trips, think about booking your Middlesboro vacation for longer.

### How to find the best Middlesboro package deals?

Start your search for a Middlesboro package deal by entering your destination and preferred travel dates under our "Packages" tab. Then add some filters, like "Guest rating" and "Property type," to fine-tune the results to your exact needs. You can also sort by "Package discount" and discover offers that come with huge savings. If you don't find the perfect Middlesboro package deal right away, just play around with your dates and search again. Bear in mind that deals are only available for a limited time, so book early and get your Middlesboro adventure off to a flying start.

### Is it cheaper to book a Middlesboro vacation as a package?

You can enjoy significant savings on your next Middlesboro break by booking a personalized vacation package. Check the "Package" heading, then select your travel dates and destination to browse some great hotel and flight prices. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a rental car and you may land a better deal.

### When to book a vacation package to Middlesboro?

Enjoy incredible discounts by reserving your flights early with Expedia. If spontaneity is more your thing, take advantage of our last-minute deals for a spur-of-the-moment Middlesboro break.

### How to plan a trip to Middlesboro?

1. Choose your dates: The things you want to do in Middlesboro and your favourite season will help you decide when to go.
2. Set a budget: Factor in expenses like flights, transportation and food when working out how much to set aside for your trip to Middlesboro. Then, select a hotel that works with your budget, whether that's a wallet-friendly option or a more upscale retreat.
3. Decide how many days away: Start by compiling a list of the sights and activities you'd like to experience in Middlesboro. Then, estimate how long you'll need at each, as well as any travel time.
4. Bundle your airfare and accommodations: After you've nailed down your dates and duration, book the ideal Middlesboro vacation package for you.

\* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.

## Other language versions

```yaml
hreflang:
  x-default: https://www.expedia.com/Middlesboro.d8853.Destination-Travel-Guides
  zh-CN: https://www.expedia.com/cn/Middlesboro.d8853.Travel
  en-MY: https://www.expedia.com.my/Middlesboro.d8853.Travel
  en-GB: https://www.expedia.co.uk/Middlesboro.d8853.Holidays-City-Breaks
  en-US: https://www.expedia.com/Middlesboro.d8853.Destination-Travel-Guides
  es: https://www.expedia.com/es/Middlesboro.d8853.Guia-de-vacaciones
```