Title: Book the Best Middlesboro FAMILY FRIENDLY Hotels from CA $89 - 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 $89 ![calendar shield illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation ![deals illustration](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) ![bed illustration](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 6 - Oct 7](https://www.expedia.ca/Hotel-Search?regionId=8853&startDate=2025-10-06&endDate=2025-10-07&adults=2&travelerType=FAMILY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 7 - Oct 8](https://www.expedia.ca/Hotel-Search?regionId=8853&startDate=2025-10-07&endDate=2025-10-08&adults=2&travelerType=FAMILY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 10 - Oct 12](https://www.expedia.ca/Hotel-Search?regionId=8853&startDate=2025-10-10&endDate=2025-10-12&adults=2&travelerType=FAMILY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=8853&startDate=2025-10-17&endDate=2025-10-19&adults=2&travelerType=FAMILY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Middlesboro Family Hotels ![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) ![Lobby lounge](https://images.trvl-media.com/lodging/2000000/1110000/1109500/1109434/4a64fadc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, Balcony, Mountain View | Aerial view](https://images.trvl-media.com/lodging/2000000/1110000/1109500/1109434/d38a5bd3.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) ### Pine Mountain State Resort Park Pineville 9.0/10 Wonderful (624) "Great place to stay on a weekend trip" CA $118 CA $130 total includes taxes & fees Oct 7 - Oct 8 [](https://www.expedia.ca/Corbin-Hotels-Pine-Mountain-State-Resort-Park.h1109434.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/4000000/3930000/3929600/3929546/1cf62fd0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 2 Queen Beds, Accessible, Non Smoking](https://images.trvl-media.com/lodging/4000000/3930000/3929600/3929546/80a66b59.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 9.2/10 Wonderful (783) "Great stay. Good breakfast. Friendly staff. Fabulous coffee!" CA $136 CA $150 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Middlesboro-Hotels-Sleep-Inn-Suites.h3929546.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) ![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) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/20000/17000/16941/94a0b136.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) ### Quality Inn Harlan 8.6/10 Excellent (320) "Wonderful stay and amenities " CA $144 CA $163 total includes taxes & fees Nov 2 - Nov 3 [](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) ![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) ![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 | Living area](https://images.trvl-media.com/lodging/15000000/14800000/14794500/14794465/e0dcd922.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cumberland Gap Inn Cumberland Gap 8.0/10 Very good (582) "The views around the area are beautiful and the town is peaceful and quiet " CA $137 CA $155 total includes taxes & fees Oct 7 - Oct 8 [](https://www.expedia.ca/Cumberland-Gap-Hotels-Cumberland-Gap-Inn.h14794465.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) ![Indoor pool](https://images.trvl-media.com/lodging/24000000/23250000/23240900/23240809/7f7a598a.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) ### Holiday Inn Express Williamsburg by IHG Williamsburg 9.0/10 Wonderful (1001) "We really enjoyed our stay! " CA $174 CA $197 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Corbin-Hotels-Holiday-Inn-Express-Williamsburg.h23240809.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/70000000/69640000/69639000/69638999/w1236h852x0y25-342874ae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, desk, free WiFi, bed sheets](https://images.trvl-media.com/lodging/70000000/69640000/69639000/69638999/c3d1b6aa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, DVD player](https://images.trvl-media.com/lodging/70000000/69640000/69639000/69638999/w1135h1684x74y0-ee937d77.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/70000000/69640000/69639000/69638999/w1272h853x0y0-6c67c5bd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Harrogate Home Mountain View’s Dog Friendly Harrogate 9.8/10 Exceptional (20) "Good space for me, my family, and my dogs to crash while we did a quick visit to the Gap." CA $139 CA $312 total includes taxes & fees Oct 7 - Oct 8 [](https://www.expedia.ca/Harrogate-Hotels-Harrogate-Home-Mountain-Views-Dog-Friendly.h69638999.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) ![Lobby](https://images.trvl-media.com/lodging/1000000/10000/7000/6940/40201ce0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![BBQ/picnic area](https://images.trvl-media.com/lodging/1000000/10000/7000/6940/7bf57be7.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) ### Super 8 by Wyndham Williamsburg Williamsburg 5.8/10 (741) "Stains on the couch, bathroom was disgusting (didn't even want to take a shower) thin sheets and blanket...very small pillows..no ice machine...broken fridge, poorly maintained" CA $89 CA $99 total includes taxes & fees Oct 12 - Oct 13 [](https://www.expedia.ca/Corbin-Hotels-Super-8-By-Wyndham-Williamsburg.h6940.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/9000000/8450000/8445600/8445506/b7b25f30.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/9000000/8450000/8445600/8445506/b203d6f3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property - evening/night](https://images.trvl-media.com/lodging/9000000/8450000/8445600/8445506/e6ebe849.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast area](https://images.trvl-media.com/lodging/9000000/8450000/8445600/8445506/77fb6beb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Rodeway Inn Harlan 5.6/10 (223) "Rundown dirty and porrly operated" CA $79 CA $89 total includes taxes & fees Nov 5 - Nov 6 [](https://www.expedia.ca/Harlan-Hotels-Mount-Aire-Motel.h8445506.Hotel-Information) ![Game room](https://images.trvl-media.com/lodging/39000000/38440000/38431000/38430925/47d50a8f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Game room](https://images.trvl-media.com/lodging/39000000/38440000/38431000/38430925/777c12ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/39000000/38440000/38431000/38430925/0f725117.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/39000000/38440000/38431000/38430925/7748d7ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Lake Front ★ No Wake w/ Dock ★ Gameroom ★ Carved FirePit ★ 2nd House Available LaFollette 10/10 Exceptional (45) "The house was beautiful and had everything we needed. The owner was very responsive to all my questions. The kids loved the game room and ping pong table." CA $345 CA $1,026 total includes taxes & fees Oct 19 - Oct 20 [](https://www.expedia.ca/Caryville-Hotels-Brand-New-Norris-Lakefront-Custom-Home.h38430925.Hotel-Information) ![Exterior detail](https://images.trvl-media.com/lodging/104000000/103940000/103938700/103938609/89fe5d47.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/104000000/103940000/103938700/103938609/19af1c21.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/104000000/103940000/103938700/103938609/e1250de4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/104000000/103940000/103938700/103938609/eb4e93a2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The House on Park Avenue-minutes to music venues Laurel Cove and Bell Theater! Pineville 9.0/10 Wonderful (2) "The home was just perfect for what we needed. Looking forward to seeing how it comes out when all construction is finished! Host was very responsive. Will stay again" CA $360 CA $542 total includes taxes & fees Oct 7 - Oct 8 [](https://www.expedia.ca/Pineville-Hotels-The-House-On-Park-Avenue-Minutes-To-Music-Venues-Laurel-Cove-And-Bell-Theater.h103938609.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=2025-10-20&endDate=2025-10-21®ionId=8853&adults=2&travelerType=family_friendly&sort=RECOMMENDED&openPlayBack=true) ## Top Middlesboro Hotel Reviews ![Sleep Inn & Suites](//images.trvl-media.com/lodging/4000000/3930000/3929600/3929546/1cf62fd0_y.jpg) ### Sleep Inn & Suites 10/10 Excellent "Beautiful setting." [](https://expedia.ca/Middlesboro-Hotels-Sleep-Inn-Suites.h3929546.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 "Clean room Great breakfast Staff friendly and helpful " [](https://expedia.ca/Middlesboro-Hotels-Holiday-Inn-Express-Middlesboro.h60850.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 "Ok" [](https://expedia.ca/Corbin-Hotels-Super-8-By-Wyndham-Williamsburg.h6940.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) ![Econo Lodge Middlesboro](//images.trvl-media.com/lodging/1000000/20000/15200/15146/853995b8_y.jpg) ### Econo Lodge Middlesboro 10/10 Excellent "Great" [](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 "Wonderful hotel. Friendly staff, well-maintained facilities, clean & comfy room. Nice hot breakfast." [](https://expedia.ca/Harlan-Hotels-Quality-Inn.h16941.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](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. Make sure you have lots of time for activities like Kentucky Ridge State Forest and Boone's Ridge Wildlife Park. ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - More ways to book - [Artemus Hotels](https://www.expedia.ca/Artemus-Hotels.d3000347263.Travel-Guide-Hotels) - [Cheap Hotels in Barbourville](https://www.expedia.ca/Barbourville-Hotels-Cheap-Hotels.0-0-d6267-tCheapHotels.Travel-Guide-Filter-Hotels) - [Barbourville Hotels](https://www.expedia.ca/Barbourville-Hotels.d6267.Travel-Guide-Hotels) - [Motels in Barbourville](https://www.expedia.ca/Barbourville-Motels.d6267-aaMotels.Travel-Guide-Accommodation) - [Bimble Hotels](https://www.expedia.ca/Bimble-Hotels.d3000347273.Travel-Guide-Hotels) - [Hotels near Black Mountain](https://www.expedia.ca/Black-Mountain-Hotels.0-l6091535-0.Travel-Guide-Filter-Hotels) - [Hotels near Boone's Ridge Wildlife Park](https://www.expedia.ca/Boones-Ridge-Wildlife-Park-Hotels.0-l814992773973426176-0.Travel-Guide-Filter-Hotels) - 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