Title: Cumberland Gap Vacation Packages & Trips 2026 | Expedia.ca [Hotels in Cumberland Gap](https://expedia.ca/Cumberland-Gap-Hotels.d10457.Travel-Guide-Hotels)[Vacation Rentals in Cumberland Gap](https://expedia.ca/Cumberland-Gap-Vacation-Rentals.d10457.Travel-Guide-VacationRentals)[Flights to Cumberland Gap](https://expedia.ca/Cheap-Flights-To-Cumberland-Gap.d10457.Travel-Guide-Flights)[Cumberland Gap Car Rentals](https://expedia.ca/Car-Rentals-In-Cumberland-Gap.d10457.Car-Rental-Guide) ![](https://images.trvl-media.com/place/10457/b9a5f580-0eed-4840-8f10-7b325cc663dc.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Cumberland Gap Vacation Packages ## Book a Hotel + Flight or Car together to unlock savings - ## Plan, book, travel with confidence - ### Better together Save up to CA $1,096 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 Cumberland Gap Vacation Select a Cumberland Gap vacation package and focus on what matters — enjoying yourself. This means no more stressful planning, just lots more time to savor the delights of this lively city, such as its rich history and spectacular views. If your trip to Cumberland Gap includes a little sightseeing, visit 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). Whoever you're heading away with and whatever you want to spend, your dream Cumberland Gap vacation is only clicks away with Expedia. ## Ready to book your vacation to Cumberland Gap? Choose your dates ## Cumberland Gap Hotel Deals ![Cumberland Gap Inn](https://images.trvl-media.com/lodging/15000000/14800000/14794500/14794465/08c2b2f6_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Cumberland Gap Inn 630 Brooklyn Street Cumberland Gap TN 8/10 Very Good! (591 reviews) The lady that checked us in was very nice and welcoming. The room was clean and comfortable. It had a nice patio overlooking a creek; what a nice suprise. The bed was comfortable. The shower had good water pressure and plenty of hot water. I would stay here again. Reviewed on Feb 17, 2026 [Get rates](https://expedia.ca/Hotel-Search?startDate=09%2F04%2F2026&endDate=10%2F04%2F2026&selected=14794465&PinnedHotelID=14794465&HadPinnedHotel=true®ionId=10457) [](https://expedia.ca/Hotel-Search?startDate=09%2F04%2F2026&endDate=10%2F04%2F2026&selected=14794465&PinnedHotelID=14794465&HadPinnedHotel=true®ionId=10457) ![The Olde Mill Inn Bed & Breakfast](https://images.trvl-media.com/lodging/10000000/9090000/9083300/9083253/5d5e1e35_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### The Olde Mill Inn Bed & Breakfast 603 Pennlyn Avenue Cumberland Gap TN CA $274 CA $311 total Apr 7 - Apr 8 includes taxes & fees 9.2/10 Wonderful! (428 reviews) We enjoyed this cozy bed and breakfast. It's a great location - so beautiful! The staff was amazing - we had a meeting at LMU and were missing breakfast. So they packed us a breakfast and put it in the common area refrigerator for us to grab in the morning. It was also handy to fill our cups with ... Reviewed on Mar 2, 2026 [](https://expedia.ca/Hotel-Search?startDate=07%2F04%2F2026&endDate=08%2F04%2F2026&selected=9083253&PinnedHotelID=9083253&HadPinnedHotel=true®ionId=10457) ![Pine Mountain State Resort Park](https://images.trvl-media.com/lodging/2000000/1110000/1109500/1109434/75b8d155_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Pine Mountain State Resort Park 1050 State Park Road Pineville KY Fully refundableReserve now, pay when you stay CA $124 CA $136 total Apr 4 - Apr 5 includes taxes & fees 9/10 Wonderful! (696 reviews) This was an amazing experience !! Everything from the room to the staff and grounds were superb!!! We will definitely be returning to stay here it was so beautiful and relaxing !!!! Reviewed on Mar 24, 2026 [](https://expedia.ca/Hotel-Search?startDate=04%2F04%2F2026&endDate=05%2F04%2F2026&selected=1109434&PinnedHotelID=1109434&HadPinnedHotel=true®ionId=10457) [See all 458 properties in Cumberland Gap](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=27%2F03%2F2026&endDate=28%2F03%2F2026®ionId=10457) 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. ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/all-inclusive_holidays_US.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) All Inclusive Vacations [](https://expedia.ca/lp/theme-vacations/all-inclusive-vacations?rfrr=editorial.All_Inclusive%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/XPC_Beach_Overview_HR_v3.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Beach Vacations [](https://expedia.ca/lp/theme-vacations/beach-vacations?rfrr=editorial.Beach_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/Family_holidays_US_3_.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Family Vacations [](https://expedia.ca/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Family_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/04/29/frCA_Sejours_golf-Portugal.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Golf Vacations [](https://expedia.ca/lp/theme-vacations/golf-vacations?rfrr=editorial.Golf_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/07/15/US_Luxury_VR_Miami.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Luxury Vacations [](https://expedia.ca/lp/theme-vacations/luxury-vacations?rfrr=editorial.Luxury_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/29/romantic.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Romantic Vacations [](https://expedia.ca/lp/theme-vacations/romantic-vacations?rfrr=editorial.Romantic_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/31952_v1_atfraraski22_insta_4.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Ski Vacations [](https://expedia.ca/lp/theme-vacations/ski-vacations?rfrr=editorial.Ski_Vacations.click) ## Explore a world of travel with Expedia \* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. ![](https://a.travel-assets.com/mad-service/footer/bnaBanners/BEX_Footer.jpg) ## Go further with the Expedia app Save on select hotels and earn double points when you book on the app. Our app deals help you to save on trips so you can travel more and manage it all on the go. Scan the QR code with your device camera and download our app