Title: Book the Best Middlesboro FAMILY FRIENDLY Hotels from CA $86 - 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) ![#Adventure #CumberlandGap #High #Trees #Highway](https://images.trvl-media.com/place/8853/b202c2ca-a802-49c4-b0c7-db992700a740.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Alexis Wyrick ![](https://images.trvl-media.com/place/8853/b202c2ca-a802-49c4-b0c7-db992700a740.jpg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](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 [Jan 30 - Jan 31](https://www.expedia.ca/Hotel-Search?regionId=8853&startDate=2026-01-30&endDate=2026-01-31&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=family_friendly) Tomorrow [Jan 31 - Feb 1](https://www.expedia.ca/Hotel-Search?regionId=8853&startDate=2026-01-31&endDate=2026-02-01&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=family_friendly) This weekend [Jan 30 - Feb 1](https://www.expedia.ca/Hotel-Search?regionId=8853&startDate=2026-01-30&endDate=2026-02-01&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=family_friendly) Next weekend [Feb 6 - Feb 8](https://www.expedia.ca/Hotel-Search?regionId=8853&startDate=2026-02-06&endDate=2026-02-08&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=family_friendly) ## Our top choices for Middlesboro family-friendly hotels ![In-room safe, desk, laptop workspace, blackout drapes](https://images.trvl-media.com/lodging/4000000/3930000/3929600/3929546/86beaca2.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) ![Exterior](https://images.trvl-media.com/lodging/4000000/3930000/3929600/3929546/5f493061.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free buffet breakfast](https://images.trvl-media.com/lodging/4000000/3930000/3929600/3929546/ff42faef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sleep Inn & Suites Middlesboro [](https://www.expedia.ca/Middlesboro-Hotels-Sleep-Inn-Suites.h3929546.Hotel-Information) Middlesboro 9.2/10 Wonderful (819 reviews) "Room was clean and comfortable. Staff was courteous. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Tommy CA $126 CA $139 total includes taxes & fees Feb 22 - Feb 23 [](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) ![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) ![Interior](https://images.trvl-media.com/lodging/111000000/110870000/110864800/110864705/fbc5418f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Charming 3-bedroom house in the Crater City near State Parks, LMU, & hospitals. [](https://www.expedia.ca/Middlesboro-Hotels-Charming-3-Bedroom-House-In-The-Crater-City-Near-State-Parks.h110864705.Hotel-Information) Middlesboro 9.2/10 Wonderful (5 reviews) "We enjoyed our stay. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Emily S. CA $236 CA $500 total includes taxes & fees Feb 1 - Feb 2 [](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) ![Lobby lounge](https://images.trvl-media.com/lodging/2000000/1110000/1109500/1109434/4a64fadc.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) ### Pine Mountain State Resort Park [](https://www.expedia.ca/Corbin-Hotels-Pine-Mountain-State-Resort-Park.h1109434.Hotel-Information) Pineville 9.0/10 Wonderful (680 reviews) "Cabin was clean and well furnished" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Marvin [](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) ![Exterior](https://images.trvl-media.com/lodging/24000000/23250000/23240900/23240809/ab1c94e5.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) ![Fitness facility](https://images.trvl-media.com/lodging/24000000/23250000/23240900/23240809/dec167ca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Express Williamsburg by IHG [](https://www.expedia.ca/Corbin-Hotels-Holiday-Inn-Express-Williamsburg.h23240809.Hotel-Information) Williamsburg 9.0/10 Wonderful (1,001 reviews) "Great staff, clean room and comfortable bed. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Beth CA $166 CA $188 total includes taxes & fees Feb 2 - Feb 3 [](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) ![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) ![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) ![Lobby lounge](https://images.trvl-media.com/lodging/1000000/20000/17000/16941/511d1b15.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Quality Inn Harlan [](https://www.expedia.ca/Harlan-Hotels-Quality-Inn.h16941.Hotel-Information) Harlan 8.6/10 Excellent (344 reviews) "Room was nice and clean, staff very courteous, breakfast very good." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Gary CA $126 CA $143 total includes taxes & fees Feb 6 - Feb 7 [](https://www.expedia.ca/Harlan-Hotels-Quality-Inn.h16941.Hotel-Information) ![Sundeck](https://images.trvl-media.com/lodging/15000000/14800000/14794500/14794465/08c2b2f6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Classic Room, 1 King Bed | Living area](https://images.trvl-media.com/lodging/15000000/14800000/14794500/14794465/963fd71e.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) ![Classic Room, 2 Queen Beds](https://images.trvl-media.com/lodging/15000000/14800000/14794500/14794465/4cd50e3f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cumberland Gap Inn [](https://www.expedia.ca/Cumberland-Gap-Hotels-Cumberland-Gap-Inn.h14794465.Hotel-Information) Cumberland Gap 8.0/10 Very good (588 reviews) "Clean love the people we always stay there when we travel south" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Christopher CA $132 CA $150 total includes taxes & fees Feb 1 - Feb 2 [](https://www.expedia.ca/Cumberland-Gap-Hotels-Cumberland-Gap-Inn.h14794465.Hotel-Information) ![House (2 Bedrooms) | Front of property](https://images.trvl-media.com/lodging/122000000/121200000/121199100/121199061/7b8fb7b1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (2 Bedrooms) | Interior](https://images.trvl-media.com/lodging/122000000/121200000/121199100/121199061/2fd54d29.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (2 Bedrooms) | Interior](https://images.trvl-media.com/lodging/122000000/121200000/121199100/121199061/e44cf9e8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (2 Bedrooms) | Interior](https://images.trvl-media.com/lodging/122000000/121200000/121199100/121199061/3ebc65a6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Peaceful & Private! Pet-friendly Williamsburg Home [](https://www.expedia.ca/Williamsburg-Hotels-Peaceful-Private-Pet-Friendly-Williamsburg-Home.h121199061.Hotel-Information) Williamsburg CA $132 CA $414 total includes taxes & fees Feb 1 - Feb 2 [](https://www.expedia.ca/Williamsburg-Hotels-Peaceful-Private-Pet-Friendly-Williamsburg-Home.h121199061.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/84000000/83700000/83695800/83695713/f29dd9f3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/84000000/83700000/83695800/83695713/23f18363.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/c3ca0191.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Calm Country Oasis - Creek, ATV Trls & Norris Lake [](https://www.expedia.ca/Speedwell-Hotels-The-Cottage-At-Silver-Creek-Farms.h83695713.Hotel-Information) Speedwell 9.4/10 Exceptional (22 reviews) " Clean rooms" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jorge h. CA $147 CA $354 total includes taxes & fees Feb 1 - Feb 2 [](https://www.expedia.ca/Speedwell-Hotels-The-Cottage-At-Silver-Creek-Farms.h83695713.Hotel-Information) ![Room, 2 Double Beds, Accessible, Non Smoking](https://images.trvl-media.com/lodging/1000000/10000/7000/6940/a5cd488f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/7000/6940/fe1198d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Seasonal outdoor pool, sun loungers](https://images.trvl-media.com/lodging/1000000/10000/7000/6940/9977ad8b.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 [](https://www.expedia.ca/Corbin-Hotels-Super-8-By-Wyndham-Williamsburg.h6940.Hotel-Information) Williamsburg 5.8/10 (784 reviews) "Clean room, friendly- helpful staff " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Melissa CA $77 CA $86 total includes taxes & fees Feb 8 - Feb 9 [](https://www.expedia.ca/Corbin-Hotels-Super-8-By-Wyndham-Williamsburg.h6940.Hotel-Information) ![Children's area](https://images.trvl-media.com/lodging/97000000/96180000/96170700/96170662/06f6fe73.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/97000000/96180000/96170700/96170662/b6eaddcc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/97000000/96180000/96170700/96170662/29f8852b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/97000000/96180000/96170700/96170662/069d1721.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Home in Powell Valley Shores Close to Flat Hollow Marina & Powell Valley Marina [](https://www.expedia.ca/Speedwell-Hotels-Home-In-Powell-Valley-Shores-Close-To-Flat-Hollow-Marina-Powell-Valley-Marina.h96170662.Hotel-Information) Speedwell 9.4/10 Exceptional (19 reviews) "Cute and cozy! Perfect place for us to use as a home base while in town visiting family. Lots of attention to the details, kitchen facilities are up to date and super clean. Already looking forward to booking again!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lynette M. CA $97 CA $215 total includes taxes & fees Feb 9 - Feb 10 [](https://www.expedia.ca/Speedwell-Hotels-Home-In-Powell-Valley-Shores-Close-To-Flat-Hollow-Marina-Powell-Valley-Marina.h96170662.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=2026-02-14&endDate=2026-02-15®ionId=8853&adults=2&travelerType=family_friendly&sort=RECOMMENDED&openPlayBack=true) ## Top Middlesboro Hotel Reviews ![Sleep Inn & Suites Middlesboro](https://images.trvl-media.com/lodging/4000000/3930000/3929600/3929546/1cf62fd0_y.jpg) ### Sleep Inn & Suites Middlesboro 10/10 Excellent "Belinda at the desk is amazing She made our stay excellent , she made us feel like we were old friends . We will be staying here on each visit . " [](https://expedia.ca/Middlesboro-Hotels-Sleep-Inn-Suites.h3929546.Hotel-Information) ![Days Inn by Wyndham Jellico - Tennessee State Line](https://images.trvl-media.com/lodging/1000000/10000/300/279/b362fe26_y.jpg) ### Days Inn by Wyndham Jellico - Tennessee State Line 10/10 Excellent "It was clean" [](https://expedia.ca/Caryville-Hotels-Days-Inn-By-Wyndham-Jellico-Tennessee-State-Line.h279.Hotel-Information) ![Holiday Inn Express Middlesboro by IHG](https://images.trvl-media.com/lodging/1000000/70000/60900/60850/3963de73_y.jpg) ### Holiday Inn Express Middlesboro by IHG 10/10 Excellent "Clean room" [](https://expedia.ca/Middlesboro-Hotels-Holiday-Inn-Express-Middlesboro.h60850.Hotel-Information) ![Super 8 by Wyndham Williamsburg](https://images.trvl-media.com/lodging/1000000/10000/7000/6940/fe1198d1_y.jpg) ### Super 8 by Wyndham Williamsburg 10/10 Excellent "Clean room, friendly- helpful staff " [](https://expedia.ca/Corbin-Hotels-Super-8-By-Wyndham-Williamsburg.h6940.Hotel-Information) ## Frequently asked questions ### Which area of Middlesboro is best to stay in for families? > Staying in the town centre means you're just a short stroll from Albert Park, a wonderful green space with a fantastic adventure playground, great for children to burn off some energy. There are also wide, paved paths suitable for prams and scooters, and plenty of open lawns for a family picnic or a game of frisbee. > > > The town centre is highly walkable, making it easy to get around with little ones without relying on a car. You'll find a good selection of casual eateries offering kid-friendly menus, as well as ice cream parlours for a sweet treat. There are also several grocery stores nearby, which are handy for stocking up on snacks and essentials for your accommodation. ### How much does a family hotel in Middlesboro cost? ### What are the best Middlesboro family-friendly hotels with a pool? > For those looking for a more budget-friendly option, the [Econo Lodge Middlesboro](https://www.expedia.ca/Middlesboro-Hotels-Econo-Lodge.h15146.Hotel-Information) is another family-friendly hotel that provides an outdoor seasonal pool. Rated at 7.2, travellers have highlighted the clean and comfortable rooms, along with the kindness of the front desk staff. Its great price point makes it an attractive option for families who want to enjoy a poolside retreat without breaking the bank. > > > Both hotels offer connecting rooms, ensuring that families can stay close together, while the convenient amenities like free WiFi and complimentary breakfasts cater to the needs of busy parents and children alike. ### Which Middlesboro family-friendly hotels welcome pets? > Another great choice is the [Econo Lodge Middlesboro](https://www.expedia.ca/Middlesboro-Hotels-Econo-Lodge.h15146.Hotel-Information), which has a review score of 7.2\. This hotel also permits pets and features connecting rooms, free Wi-Fi, and a complimentary continental breakfast. Travellers appreciate the fantastic cleanliness of the rooms and the comfy beds, making it a suitable retreat for families looking for good value. The kind front desk staff further enhances the experience, ensuring a pleasant stay for those travelling with furry companions. ### Which family-friendly hotels are in central Middlesboro? > Another excellent choice is the [Sleep Inn & Suites](https://www.expedia.ca/Middlesboro-Hotels-Sleep-Inn-Suites.h3929546.Hotel-Information), with a review score of 9.2\. This hotel is particularly well-suited for families, offering free cribs for younger guests and comfortable sofa beds. Guests often praise the friendly and attentive staff, as well as the inviting patio area, ideal for relaxing after a day of exploration. The complimentary breakfast here is also a hit, ensuring that everyone starts their day on the right foot. > > > If you're seeking a more budget-friendly option, the [Econo Lodge Middlesboro](https://www.expedia.ca/Middlesboro-Hotels-Econo-Lodge.h15146.Hotel-Information) might be a good fit, with a traveller rating of 7.2\. This hotel offers connecting rooms and free Wi-Fi, which is great for families needing to stay connected. Guests have noted the fantastic cleanliness of the rooms and the comfortable beds, making it a great value for those looking to keep costs down while enjoying their stay in central Middlesboro. ### What family-friendly activities should we do in Middlesboro? > One fantastic option is to explore the Cumberland Gap National Historical Park, which offers a variety of trails suitable for families. You can take a gentle stroll along trails that lead to scenic overlooks, providing breathtaking views of the natural landscape and explaining the historical importance of the pass. It's a wonderful way to connect with nature and learn about the pioneers. > > > Another engaging activity is a visit to the Bell County Historical Society Museum. This museum offers a fascinating glimpse into the local history of Middlesboro and the surrounding area, with exhibits that can spark curiosity in children about what life was like in times gone by. It's a great indoor option for a rainy day. > > > For some outdoor fun, Middlesboro City Park provides ample space for children to play, with playgrounds and open areas superb for a family picnic or throwing a frisbee. ### Are there any great family hotels in Middlesboro with a gym? > Another excellent option is the [Sleep Inn & Suites](https://www.expedia.ca/Middlesboro-Hotels-Sleep-Inn-Suites.h3929546.Hotel-Information), which also features fitness facilities for those who want to stay active during their stay. Families appreciate the comfortable and clean rooms, along with the friendly service from the staff, making it a popular choice. With complimentary breakfast and a lovely patio area, it's superb for families looking to relax after a day of adventures. ### How can I save on a family-friendly hotel in Middlesboro with Expedia? ### Can I cancel my family hotel reservation on Expedia? ## 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) - 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