Title: Middlesboro Condo Rentals from CA $110 | 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 # Search Condos Rentals in Middlesboro from CA $110 - ![](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 prices for these dates In two weeks [Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=8853&startDate=2025-12-19&endDate=2025-12-21&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Jan 30 - Feb 1](https://www.expedia.ca/Hotel-Search?regionId=8853&startDate=2026-01-30&endDate=2026-02-01&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [Feb 27 - Mar 1](https://www.expedia.ca/Hotel-Search?regionId=8853&startDate=2026-02-27&endDate=2026-03-01&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [Mar 27 - Mar 29](https://www.expedia.ca/Hotel-Search?regionId=8853&startDate=2026-03-27&endDate=2026-03-29&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Browse Select Middlesboro Condo Rentals No exact matches found, but these alternatives could be just right ## Recommended hotels in Middlesboro ![Standard Room](https://images.trvl-media.com/lodging/1000000/70000/60900/60850/3963de73.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/70000/60900/60850/2eaf3737.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/1000000/70000/60900/60850/27ee2711.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/70000/60900/60850/d8f164b4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Express Middlesboro by IHG Middlesboro 9.6/10 Exceptional (691) "Clean hotel, good breakfast options." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Harold CA $161 CA $178 total includes taxes & fees Dec 21 - Dec 22 [](https://www.expedia.ca/Middlesboro-Hotels-Holiday-Inn-Express-Middlesboro.h60850.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) ![Lobby](https://images.trvl-media.com/lodging/4000000/3930000/3929600/3929546/650307df.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) ![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) ### Sleep Inn & Suites Middlesboro Middlesboro 9.2/10 Wonderful (810) "The breakfast was great and customer service was great! Very clean and beautiful views " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Solange CA $129 CA $143 total includes taxes & fees Dec 23 - Dec 24 [](https://www.expedia.ca/Middlesboro-Hotels-Sleep-Inn-Suites.h3929546.Hotel-Information) ![Standard Room, 1 Queen Bed, Non Smoking](https://images.trvl-media.com/lodging/70000000/69400000/69390100/69390006/1f420a69.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/70000000/69400000/69390100/69390006/a277b250.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/70000000/69400000/69390100/69390006/88c4c8c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave](https://images.trvl-media.com/lodging/70000000/69400000/69390100/69390006/bb8a8e6f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Suburban Studios Middlesboro Middlesboro 8.0/10 Very good (66) "Didn't stay as we found a better location in Cumberland Gap. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Alan CA $108 CA $119 total includes taxes & fees Dec 26 - Dec 27 [](https://www.expedia.ca/Middlesboro-Hotels-Suburban-Extended-Stay-Hotel.h69390006.Hotel-Information) ![Double Room, Smoking](https://images.trvl-media.com/lodging/35000000/34980000/34978900/34978817/347cf131.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Single Room, 1 Queen Bed, Smoking](https://images.trvl-media.com/lodging/35000000/34980000/34978900/34978817/2a62b61c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/35000000/34980000/34978900/34978817/cbceebb5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Single Room, 1 Queen Bed, Smoking](https://images.trvl-media.com/lodging/35000000/34980000/34978900/34978817/df5282ca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Boone Trail Inn Middlesboro 7.2/10 Good (110) "Place was clean. AC worked good. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) David CA $87 CA $120 total includes taxes & fees Dec 29 - Dec 30 [](https://www.expedia.ca/Middlesboro-Hotels-Boone-Trail-Inn.h34978817.Hotel-Information) ![Standard Room, 2 Double Beds, Non Smoking](https://images.trvl-media.com/lodging/1000000/20000/15200/15146/853995b8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Snack bar](https://images.trvl-media.com/lodging/1000000/20000/15200/15146/5b2610cc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/20000/15200/15146/e2e08685.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Seasonal outdoor pool, open 10:00 AM to 10:00 PM, sun loungers](https://images.trvl-media.com/lodging/1000000/20000/15200/15146/c38450c1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Econo Lodge Middlesboro Middlesboro 7.4/10 Good (445) "Clean place with friendly staff. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) James CA $111 CA $123 total includes taxes & fees Dec 9 - Dec 10 [](https://www.expedia.ca/Middlesboro-Hotels-Econo-Lodge.h15146.Hotel-Information) ![2 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/114000000/113130000/113124900/113124803/a21e0b91.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/114000000/113130000/113124900/113124803/26260269.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/114000000/113130000/113124900/113124803/402a8ad1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/114000000/113130000/113124900/113124803/3ea56b6c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 4.6 miles from LMU. Cozy 2-bedroom Lustron home located in Middlesboro, Ky, Middlesboro 10/10 Exceptional (22) "Great property! Very clean and homey!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lillian I. CA $166 CA $325 total includes taxes & fees Dec 16 - Dec 17 [](https://www.expedia.ca/Middlesboro-Hotels-Cozy-2-Bedroom-Lustron-Home-Located-In-Middlesboro.h113124803.Hotel-Information) ![Microwave, oven, stovetop](https://images.trvl-media.com/lodging/118000000/117740000/117736400/117736392/w2000h2797x0y0-ff41d957.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/118000000/117740000/117736400/117736392/w1997h2800x0y0-b5dc7fe0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/118000000/117740000/117736400/117736392/a482c2a6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/118000000/117740000/117736400/117736392/41b0b274.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Spacious Renovated Ranch Retreat near Tackett Creek & Cumberland Gap Park, & LMU Middlesboro 10/10 Exceptional (1) "Clean" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Phineas S. CA $290 CA $540 total includes taxes & fees Dec 10 - Dec 11 [](https://www.expedia.ca/Middlesboro-Hotels-Spacious-Renovated-Ranch-Retreat-Near-Tackett-Creek-Cumberland-Gap-Park.h117736392.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) ![Interior](https://images.trvl-media.com/lodging/111000000/110870000/110864800/110864705/439f4fac.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/111000000/110870000/110864800/110864705/2a088af8.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 $244 CA $519 total includes taxes & fees Dec 16 - Dec 17 [](https://www.expedia.ca/Middlesboro-Hotels-Charming-3-Bedroom-House-In-The-Crater-City-Near-State-Parks.h110864705.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/120000000/119650000/119642400/119642383/f536237c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/120000000/119650000/119642400/119642383/2f2cc548.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/120000000/119650000/119642400/119642383/bc55821d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/120000000/119650000/119642400/119642383/d9971f16.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Welcoming 3-bedroom house with AC in charming Middlesboro Middlesboro CA $187 CA $368 total includes taxes & fees Dec 16 - Dec 17 [](https://www.expedia.ca/Middlesboro-Hotels-Welcoming-3-Bedroom-House-With-AC-In-Charming-Middlesboro.h119642383.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) ![Lobby](https://images.trvl-media.com/lodging/24000000/23250000/23240900/23240809/4cc09473.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) ![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) ### Holiday Inn Express Williamsburg by IHG Williamsburg 9.0/10 Wonderful (1004) "We really enjoyed our stay! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Andrea Strode CA $139 CA $157 total includes taxes & fees Dec 10 - Dec 11 [](https://www.expedia.ca/Corbin-Hotels-Holiday-Inn-Express-Williamsburg.h23240809.Hotel-Information) ![Room, 1 King Bed, Non Smoking](https://images.trvl-media.com/lodging/114000000/113970000/113960300/113960224/85457286.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/114000000/113970000/113960300/113960224/68e298aa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/114000000/113970000/113960300/113960224/11021c25.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 2 Double Beds, Non Smoking | Bathroom](https://images.trvl-media.com/lodging/114000000/113970000/113960300/113960224/176ec9e3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Imperial Inn by OYO Tazewell Tazewell 9.0/10 Wonderful (45) "Great hotel" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Tahir [](https://www.expedia.ca/Tazewell-Hotels-Imperial-Inn.h113960224.Hotel-Information) ![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) ![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) ![Flat-screen TV](https://images.trvl-media.com/lodging/2000000/1110000/1109500/1109434/a5889142.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Pine Mountain State Resort Park Pineville 9.0/10 Wonderful (667) "Staff were amazing! Very unique experience in the cottage and the fireplace was really special highly recommended!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Andrew CA $153 CA $168 total includes taxes & fees Dec 9 - Dec 10 [](https://www.expedia.ca/Corbin-Hotels-Pine-Mountain-State-Resort-Park.h1109434.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) ![Reception](https://images.trvl-media.com/lodging/1000000/20000/17000/16941/e1327cb3.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) ### Quality Inn Harlan 8.6/10 Excellent (335) "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 $129 CA $146 total includes taxes & fees Dec 14 - Dec 15 [](https://www.expedia.ca/Harlan-Hotels-Quality-Inn.h16941.Hotel-Information) ![Suite, Accessible, Ensuite (Thomas Walker Annex)](https://images.trvl-media.com/lodging/10000000/9090000/9083300/9083253/d129b690.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Superior Suite, Ensuite (a The Suite)](https://images.trvl-media.com/lodging/10000000/9090000/9083300/9083253/ff3382f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Miscellaneous](https://images.trvl-media.com/lodging/10000000/9090000/9083300/9083253/b8a5ded6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Miscellaneous](https://images.trvl-media.com/lodging/10000000/9090000/9083300/9083253/78c6bb28.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Olde Mill Inn Bed & Breakfast Cumberland Gap 9.0/10 Wonderful (425) "Nice place in historic Cumberland Gap, walkable to hiking trail and pave local trail. The room is spacious, very clean, and comfortable bed. Homemade breakfast was delicious." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ry CA $187 CA $212 total includes taxes & fees Dec 14 - Dec 15 [](https://www.expedia.ca/Cumberland-Gap-Hotels-The-Olde-Mill-Inn-Bed-Breakfast.h9083253.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/1000000/10000/300/279/b362fe26.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/10000/300/279/c209de71.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Laundry room](https://images.trvl-media.com/lodging/1000000/10000/300/279/08173c4a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Combined shower/tub, deep soaking tub, hydromassage showerhead](https://images.trvl-media.com/lodging/1000000/10000/300/279/cfa269f3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Days Inn by Wyndham Jellico - Tennessee State Line Jellico 7.2/10 Good (1007) "Very clean and quiet I loved and enjoyed my 3 nights and 4 day stay!!! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Antoninette CA $96 CA $110 total includes taxes & fees Dec 16 - Dec 17 [](https://www.expedia.ca/Caryville-Hotels-Days-Inn-By-Wyndham-Jellico-Tennessee-State-Line.h279.Hotel-Information) ![Business centre](https://images.trvl-media.com/lodging/1000000/20000/17100/17023/150349c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/20000/17100/17023/93f0a861.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Quality Inn Barbourville 8.2/10 Very good (266) "Room was clean and clerk was nice especially since it was early morning " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Billy CA $144 CA $163 total includes taxes & fees Jan 1 - Jan 2, 2026 [](https://www.expedia.ca/Corbin-Hotels-Best-Western-Wilderness-Trail-Inn.h17023.Hotel-Information) ![House (2 Bedrooms) | Interior](https://images.trvl-media.com/lodging/122000000/121200000/121199100/121199061/5f60b3d0.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/ebf9cd54.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/cbbad019.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (2 Bedrooms) | Interior](https://images.trvl-media.com/lodging/122000000/121200000/121199100/121199061/7175025c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Peaceful & Private! Pet-friendly Williamsburg Home Williamsburg CA $137 CA $429 total includes taxes & fees Dec 16 - Dec 17 [](https://www.expedia.ca/Williamsburg-Hotels-Peaceful-Private-Pet-Friendly-Williamsburg-Home.h121199061.Hotel-Information) ![Aerial view](https://images.trvl-media.com/lodging/17000000/16540000/16536400/16536329/544d1b99.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lounge](https://images.trvl-media.com/lodging/17000000/16540000/16536400/16536329/fed88dd6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/17000000/16540000/16536400/16536329/32a090b3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/17000000/16540000/16536400/16536329/55fb9b6c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Woodlake Lodge Golf and Country Club Tazewell 9.4/10 Exceptional (142) "Gym was closed, restaurant was closed... pool was nice. Course is beautiful." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Daniel CA $182 CA $204 total includes taxes & fees Jan 1 - Jan 2, 2026 [](https://www.expedia.ca/Morristown-Hotels-Woodlake-Lodge-Golf-And-Country-Club.h16536329.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 | Living area](https://images.trvl-media.com/lodging/15000000/14800000/14794500/14794465/e0dcd922.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) ### 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 Dec 9 - Dec 10 [](https://www.expedia.ca/Cumberland-Gap-Hotels-Cumberland-Gap-Inn.h14794465.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/13000000/12230000/12227200/12227125/54803958.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/13000000/12230000/12227200/12227125/0348c6db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Combined shower/tub, free toiletries, hair dryer, towels](https://images.trvl-media.com/lodging/13000000/12230000/12227200/12227125/cf3b5701.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/13000000/12230000/12227200/12227125/6b948c2b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Tazewell Motor Lodge Tazewell 9.0/10 Wonderful (86) "The room was dated but clean and had every convenience. The bed was comfortable, there were several TV channels to choose from, a nice refrigerator and microwave and even an ironing board and iron. Patrick was very friendly and accommodating and I’ll stay there again next trip. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Betty [](https://www.expedia.ca/Morristown-Hotels-Tazewell-Motor-Lodge.h12227125.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=2025-12-17&endDate=2025-12-18®ionId=8853&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true) ![](https://forever.travel-assets.com/flex/flexmanager/images/2025/11/05/BEX-BF-25_CA_1_Desktop.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## Black Friday Sale Limited-time deals: save up to 50% on select hotels [Book now](https://expedia.ca/deals?rfrr=AA_BF_PROMO_8853) ![](https://a.travel-assets.com/pricing-claim/sparkle_dark.svg) Save an average of 15% on thousands of hotels when you're signed in [Sign in](https://expedia.ca/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FMiddlesboro-Condos.d8853-aaCondos.Travel-Guide-Accommodation)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FMiddlesboro-Condos.d8853-aaCondos.Travel-Guide-Accommodation) ## Top Middlesboro Hotel Reviews ![Pine Mountain State Resort Park](https://images.trvl-media.com/lodging/2000000/1110000/1109500/1109434/75b8d155_y.jpg) ### Pine Mountain State Resort Park 10/10 Excellent "The staff here is amazing. Everyone was really nice and helpful:)" [](https://expedia.ca/Corbin-Hotels-Pine-Mountain-State-Resort-Park.h1109434.Hotel-Information) ![Sleep Inn & Suites Middlesboro](https://images.trvl-media.com/lodging/4000000/3930000/3929600/3929546/1cf62fd0_y.jpg) ### Sleep Inn & Suites Middlesboro 10/10 Excellent "Entire facility was spotless. Great staff. Breakfast was a normal hotel breakfast but was well organized and stocked. Didn’t feel like a gross buffet as it does at some hotels. " [](https://expedia.ca/Middlesboro-Hotels-Sleep-Inn-Suites.h3929546.Hotel-Information) ![Quality Inn](https://images.trvl-media.com/lodging/1000000/20000/17000/16941/b003bff0_y.jpg) ### Quality Inn 10/10 Excellent "Nice." [](https://expedia.ca/Harlan-Hotels-Quality-Inn.h16941.Hotel-Information) ![Family Affair, room 4 30, 15 Beds, 2 FULL Kitchens!!! Huge dock w 2 boat slips](https://images.trvl-media.com/lodging/34000000/33080000/33075400/33075394/87720b5d_y.jpg) ### Family Affair, room 4 30, 15 Beds, 2 FULL Kitchens!!! Huge dock w 2 boat slips 10/10 Excellent "Our family had the most amazing vacation at Family Affair home!! There is so much space. We had more than enough space for our family. The bedrooms are all spacious. There is so much to do that we hardly ever left the house. With 2 kitchens and dining areas we had everything we needed for our family chef to do his thing. The kids had a blast playing and running around the area hiking and exploring.We will be back in the summer time and take a trip to the jumping bridge!!The double decks on the boat dock was awesome for sitting and enjoying the beautiful views!" [](https://expedia.ca/La-Follette-Hotels-Family-Affair.h33075394.Hotel-Information) ![Holiday Inn Express Williamsburg by IHG](https://images.trvl-media.com/lodging/24000000/23250000/23240900/23240809/7b78ad82_y.jpg) ### Holiday Inn Express Williamsburg by IHG 10/10 Excellent "Every part of this hotel was outstanding for travelers such as us" [](https://expedia.ca/Corbin-Hotels-Holiday-Inn-Express-Williamsburg.h23240809.Hotel-Information) ![The Olde Mill Inn Bed & Breakfast](https://images.trvl-media.com/lodging/10000000/9090000/9083300/9083253/d129b690_y.jpg) ### The Olde Mill Inn Bed & Breakfast 10/10 Excellent "Very clean room, fantastic pieces inside with lots of history and a magnificent breakfast!!" [](https://expedia.ca/Cumberland-Gap-Hotels-The-Olde-Mill-Inn-Bed-Breakfast.h9083253.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 "We did not visit the pool,but it looked nice. Staff was very friendly and helpful. Especially the front desk people. Our housekeeper was very helpful. Also,very convenient to the highway." [](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 "Very comfortable and clean." [](https://expedia.ca/Middlesboro-Hotels-Holiday-Inn-Express-Middlesboro.h60850.Hotel-Information) ![Rodeway Inn](https://images.trvl-media.com/lodging/9000000/8450000/8445600/8445506/b7b25f30_y.jpg) ### Rodeway Inn 10/10 Excellent "Clean and staff was good The bathroom is putting out a bad smell like it was from the septic and we tried three different microwaves that did not work that was my only complaint" [](https://expedia.ca/Harlan-Hotels-Mount-Aire-Motel.h8445506.Hotel-Information) ## Find out more about Middlesboro ## Middlesboro Condo Rentals information | Number of reviews | 6,447 | | --- | --- | | Accommodation | 1 Condo Rentals | | Lowest Price | CA $110 | | Highest Price | CA $540 | ## Frequently asked questions ### Why book your condo in Middlesboro with Expedia? > Expedia will help you find your ideal condo in Middlesboro. After a luxury escape? Make use of our filters to search for properties that have a 5-star rating. If you're on a budget, choose how much you want to spend and then check out our amazing deals. We'll help you find the right place whatever your trip looks like. ### How can I find cheap condos in Middlesboro? > With Expedia's handy filter tool, scoring cheap condos in Middlesboro is a piece of cake. To discover accommodations that are easy on your bank balance, narrow your search results by star rating, budget and amenities. ### What is there to do in Middlesboro near my condo? > The most practical travel accessory is a well-planned schedule. 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[Rapid River Lodge & Water Park](https://www.expedia.ca/Rapid-River-Lodge-Water-Park-Kentucky.d553248621532651998.Vacation-Attraction) - [Car rental Corbin](https://www.expedia.ca/Car-Rentals-In-Corbin.d6059437.Car-Rental-Guide) - [Car rental Harlan](https://www.expedia.ca/Car-Rentals-In-Harlan.d8279.Car-Rental-Guide) - [Car rental Williamsburg](https://www.expedia.ca/Car-Rentals-In-Williamsburg.d7856.Car-Rental-Guide) - [Corbin Vacation Rentals](https://www.expedia.ca/Corbin-Vacation-Rentals.d6059437.Travel-Guide-VacationRentals) - [Gray Vacation Rentals](https://www.expedia.ca/Gray-Vacation-Rentals.d889086718113042432.Travel-Guide-VacationRentals) - [Book Condo Rentals in Middlesboro on Expedia.com](https://www.expedia.com/Middlesboro-Condos.d8853-aaCondos.Travel-Guide-Accommodation)