Title: Book the Best Middlesboro FAMILY FRIENDLY Hotels from CA $99 - Kid-Friendly Hotels in Middlesboro, KY | Expedia.ca [Hotels in Middlesboro](https://expedia.ca/Middlesboro-Hotels.d8853.Travel-Guide-Hotels)[Vacation Rentals in Middlesboro](https://expedia.ca/Middlesboro-Vacation-Rentals.d8853.Travel-Guide-VacationRentals)[Flights to Middlesboro](https://expedia.ca/Cheap-Flights-To-Middlesboro.d8853.Travel-Guide-Flights)[Middlesboro Car Rentals](https://expedia.ca/Car-Rentals-In-Middlesboro.d8853.Car-Rental-Guide)[Middlesboro Vacation Packages](https://expedia.ca/Middlesboro.d8853.Destination-Travel-Guides) ![](https://mediaim.expedia.com/destination/2/aaf95e2362319d0be23171c8a72261cf.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Alexis Wyrick # Find Family Hotels in Middlesboro, KY from CA $99 ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Sign in to save 10% or more on thousands of hotels [Sign in](https://www.expedia.ca/login) ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check availability on Middlesboro Family Hotels Tonight [Oct 29 - Oct 30](https://www.expedia.ca/Hotel-Search?regionId=8853&startDate=2025-10-29&endDate=2025-10-30&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=family_friendly) Tomorrow [Oct 30 - Oct 31](https://www.expedia.ca/Hotel-Search?regionId=8853&startDate=2025-10-30&endDate=2025-10-31&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=family_friendly) This weekend [Oct 31 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=8853&startDate=2025-10-31&endDate=2025-11-02&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=family_friendly) Next weekend [Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=8853&startDate=2025-11-07&endDate=2025-11-09&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=family_friendly) ## Top Middlesboro Family Hotels ![Exterior](https://images.trvl-media.com/lodging/4000000/3930000/3929600/3929546/1cf62fd0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/4000000/3930000/3929600/3929546/650307df.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/4000000/3930000/3929600/3929546/78cde3c2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free buffet breakfast](https://images.trvl-media.com/lodging/4000000/3930000/3929600/3929546/29498a28.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sleep Inn & Suites Middlesboro Middlesboro 9.2/10 Wonderful (798) "Clean, super nice staff, bed comfortable " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kay CA $130 CA $144 total includes taxes & fees Nov 16 - Nov 17 [](https://www.expedia.ca/Middlesboro-Hotels-Sleep-Inn-Suites.h3929546.Hotel-Information) ![3 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/111000000/110870000/110864800/110864705/c11669c3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/111000000/110870000/110864800/110864705/cde6bef3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, books, stereo](https://images.trvl-media.com/lodging/111000000/110870000/110864800/110864705/a0ca2385.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/111000000/110870000/110864800/110864705/439f4fac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Charming 3-bedroom house in the Crater City near State Parks, LMU, & hospitals. Middlesboro 9.2/10 Wonderful (5) "We enjoyed our stay. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Emily S. CA $215 CA $481 total includes taxes & fees Nov 4 - Nov 5 [](https://www.expedia.ca/Middlesboro-Hotels-Charming-3-Bedroom-House-In-The-Crater-City-Near-State-Parks.h110864705.Hotel-Information) ![Outdoor pool, open 9:00 AM to 9:00 PM, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/2000000/1110000/1109500/1109434/9e293866.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor wedding area](https://images.trvl-media.com/lodging/2000000/1110000/1109500/1109434/75b8d155.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior entrance](https://images.trvl-media.com/lodging/2000000/1110000/1109500/1109434/4ec8d24c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby lounge](https://images.trvl-media.com/lodging/2000000/1110000/1109500/1109434/4a64fadc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Pine Mountain State Resort Park Pineville 9.0/10 Wonderful (643) "Great views, and wonderful trails, and pet-friendly." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Frederick CA $98 CA $108 total includes taxes & fees Oct 30 - Oct 31 [](https://www.expedia.ca/Corbin-Hotels-Pine-Mountain-State-Resort-Park.h1109434.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/24000000/23250000/23240900/23240809/7b78ad82.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, premium bedding, pillowtop beds, in-room safe](https://images.trvl-media.com/lodging/24000000/23250000/23240900/23240809/cf8d091b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/24000000/23250000/23240900/23240809/4cc09473.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily on-the-go breakfast](https://images.trvl-media.com/lodging/24000000/23250000/23240900/23240809/ae60acb7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Express Williamsburg by IHG Williamsburg 9.0/10 Wonderful (1000) "We really enjoyed our stay! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Andrea Strode CA $174 CA $197 total includes taxes & fees Nov 16 - Nov 17 [](https://www.expedia.ca/Corbin-Hotels-Holiday-Inn-Express-Williamsburg.h23240809.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/20000/17000/16941/b003bff0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![In-room safe, desk, laptop workspace, blackout drapes](https://images.trvl-media.com/lodging/1000000/20000/17000/16941/43d53c9f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily continental breakfast](https://images.trvl-media.com/lodging/1000000/20000/17000/16941/0451853f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/20000/17000/16941/e1327cb3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Quality Inn Harlan 8.6/10 Excellent (325) "The breakfast was great and the parking lot felt safe and had plenty of lighting. Overall a good stay." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) James CA $131 CA $148 total includes taxes & fees Nov 16 - Nov 17 [](https://www.expedia.ca/Harlan-Hotels-Quality-Inn.h16941.Hotel-Information) ![Honeymoon Suite, 1 King Bed](https://images.trvl-media.com/lodging/15000000/14800000/14794500/14794465/a3c8a3ba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Sundeck](https://images.trvl-media.com/lodging/15000000/14800000/14794500/14794465/08c2b2f6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Honeymoon Suite, 1 King Bed | Room amenity](https://images.trvl-media.com/lodging/15000000/14800000/14794500/14794465/a793dced.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Point of interest](https://images.trvl-media.com/lodging/15000000/14800000/14794500/14794465/e27de054.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cumberland Gap Inn Cumberland Gap 8.0/10 Very good (583) "The views around the area are beautiful and the town is peaceful and quiet " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Robert CA $137 CA $155 total includes taxes & fees Oct 30 - Oct 31 [](https://www.expedia.ca/Cumberland-Gap-Hotels-Cumberland-Gap-Inn.h14794465.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/84000000/83790000/83783900/83783898/1a7d1e20.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/84000000/83790000/83783900/83783898/2703de40.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/84000000/83790000/83783900/83783898/9e266762.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/84000000/83790000/83783900/83783898/fa489755.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy Cumberland Gap Cottage Near LMU & Nat’l Park Cumberland Gap 9.2/10 Wonderful (41) "Just as advertised. Very quiet and enjoyable stay!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Anonymous traveller CA $138 CA $297 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Cumberland-Gap-Hotels-Cozy-Cumberland-Gap-Cottage.h83783898.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/84000000/83700000/83695800/83695713/1534c84b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/84000000/83700000/83695800/83695713/f29dd9f3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/84000000/83700000/83695800/83695713/8c08cce2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/84000000/83700000/83695800/83695713/73174492.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Calm Country Oasis - Creek, ATV Trls & Norris Lake Speedwell 9.4/10 Exceptional (19) "We had a wonderful weekend:)" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Bobbi F. CA $159 CA $374 total includes taxes & fees Nov 5 - Nov 6 [](https://www.expedia.ca/Speedwell-Hotels-The-Cottage-At-Silver-Creek-Farms.h83695713.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/7000/6940/fe1198d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Soundproofing, iron/ironing board, free cribs/infant beds, free WiFi](https://images.trvl-media.com/lodging/1000000/10000/7000/6940/b5e2ff38.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![BBQ/picnic area](https://images.trvl-media.com/lodging/1000000/10000/7000/6940/938915dc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/10000/7000/6940/40201ce0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Super 8 by Wyndham Williamsburg Williamsburg 5.8/10 (752) "Love the Mint.." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Tracy CA $89 CA $99 total includes taxes & fees Nov 9 - Nov 10 [](https://www.expedia.ca/Corbin-Hotels-Super-8-By-Wyndham-Williamsburg.h6940.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/78000000/77970000/77968800/77968737/e3fab1a5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace, DVD player](https://images.trvl-media.com/lodging/78000000/77970000/77968800/77968737/a1947846.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/78000000/77970000/77968800/77968737/e4e66de7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![4 bedrooms, iron/ironing board, internet, bed sheets](https://images.trvl-media.com/lodging/78000000/77970000/77968800/77968737/7504486e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 3-story lakefront rustic cabin w/pool table, private hot tub, gas fireplace, A/C New Tazewell 9.4/10 Exceptional (29) "One reason we chose this home is because it was only about 10 minutes from the cabin owned by my daughter. Her place was too small to accommodate more than a couple extra guests. Since we had 7 guests, we needed to rent a place. Views were very pretty and kitchen was stocked with accessories needed to prepare meals (grocery stores/restaurants and too far away so make sure you have everything you need. House is not soundproof (typical of this type of home) so any tv's, conversations, etc need... ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lynn P. CA $230 CA $828 total includes taxes & fees Nov 4 - Nov 5 [](https://www.expedia.ca/New-Tazewell-Hotels-2-Story-Lakefront-Rustic-Cabin-Wpool-Table.h77968737.Hotel-Information) 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. [View all properties](https://expedia.ca/Hotel-Search?startDate=2025-11-12&endDate=2025-11-13®ionId=8853&adults=2&travelerType=family_friendly&sort=RECOMMENDED&openPlayBack=true) ## Top Middlesboro Hotel Reviews ![Econo Lodge Middlesboro](//images.trvl-media.com/lodging/1000000/20000/15200/15146/853995b8_y.jpg) ### Econo Lodge Middlesboro 10/10 Excellent "Clean rooms" [](https://expedia.ca/Middlesboro-Hotels-Econo-Lodge.h15146.Hotel-Information) ![Quality Inn](//images.trvl-media.com/lodging/1000000/20000/17000/16941/b003bff0_y.jpg) ### Quality Inn 10/10 Excellent "I was visiting family in the Harlan area. I really liked this motel, convenient, quiet, safe and the breakfast was great. I would not hesitate to stay there again. " [](https://expedia.ca/Harlan-Hotels-Quality-Inn.h16941.Hotel-Information) ![Sleep Inn & Suites](//images.trvl-media.com/lodging/4000000/3930000/3929600/3929546/1cf62fd0_y.jpg) ### Sleep Inn & Suites 10/10 Excellent "Clean, super nice staff, bed comfortable " [](https://expedia.ca/Middlesboro-Hotels-Sleep-Inn-Suites.h3929546.Hotel-Information) ![Super 8 by Wyndham Williamsburg](//images.trvl-media.com/lodging/1000000/10000/7000/6940/fe1198d1_y.jpg) ### Super 8 by Wyndham Williamsburg 10/10 Excellent "Both visits were spectacular ..." [](https://expedia.ca/Corbin-Hotels-Super-8-By-Wyndham-Williamsburg.h6940.Hotel-Information) ![Holiday Inn Express Middlesboro by IHG](//images.trvl-media.com/lodging/1000000/70000/60900/60850/3963de73_y.jpg) ### Holiday Inn Express Middlesboro by IHG 10/10 Excellent "Great breakfast. Room was spacious, clean and the dove products in the bathroom were nice. Great stay. " [](https://expedia.ca/Middlesboro-Hotels-Holiday-Inn-Express-Middlesboro.h60850.Hotel-Information) ![Days Inn by Wyndham Jellico - Tennessee State Line](//images.trvl-media.com/lodging/1000000/10000/300/279/b362fe26_y.jpg) ### Days Inn by Wyndham Jellico - Tennessee State Line 10/10 Excellent "Clean newly remodeled spacious room. Comfortable bed. Parked at our door. Quiet. Friendly staff. Comfortable tub. Hot water plentiful. Serene surroundings. Cute small town. Could use more lighting around mirror at the sink. Good value. Highly recommended." [](https://expedia.ca/Caryville-Hotels-Days-Inn-By-Wyndham-Jellico-Tennessee-State-Line.h279.Hotel-Information) ![Quality Inn](//images.trvl-media.com/lodging/1000000/20000/17100/17023/150349c9_y.jpg) ### Quality Inn 10/10 Excellent "I recently stayed 2 nights here. My stay was wonderful. Everything was clean and fresh. I actually felt at home here. Great job!!!" [](https://expedia.ca/Corbin-Hotels-Best-Western-Wilderness-Trail-Inn.h17023.Hotel-Information) ## Frequently asked questions ### What's Middlesboro like for family-friendly vacations? > The destination of Middlesboro is a great choice if you've been thinking about a vacation with your kids. The wildlife, glaciers, and mountain views are just a few things that make this an attractive spot for a family vacation. ### What's the best accommodation for families in Middlesboro? > [Sleep Inn & Suites Middlesboro](https://www.expedia.ca/Middlesboro-Hotels-Sleep-Inn-Suites.h3929546.Hotel-Information) is a hotel with free parking and free buffet breakfast, and it's a top choice on Expedia for families. ### When's the best time to book a family-friendly vacation in Middlesboro? > The hottest months are usually July and August with an average temp of 72°F, while the coldest months are January and February with an average of 40°F. Average annual precipitation for Middlesboro is 62 inches. ### What's there to see and do with your family in Middlesboro? > Middlesboro Mall and Bell County Public Library Pineville Branch are interesting attractions you and your family might enjoy exploring while you are staying in Middlesboro. 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