Title: Middlesboro Vacation Home Rentals from CA $557: Search Top Private Vacation Homes for Rent | 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 # Middlesboro Vacation Rentals ### Change your mind Book hotels with free cancellation ### Treat yourself Sign in to save 10% or more on thousands of hotels [Sign in](https://www.expedia.ca/login) ### Be picky Search almost a million properties worldwide ## Check prices for these dates Next weekend [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=8853&startDate=2025-10-17&endDate=2025-10-19&adults=2&lodging=VACATION_HOME&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=8853&startDate=2025-10-24&endDate=2025-10-26&adults=2&lodging=VACATION_HOME&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=8853&startDate=2025-11-07&endDate=2025-11-09&adults=2&lodging=VACATION_HOME&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Dec 5 - Dec 7](https://www.expedia.ca/Hotel-Search?regionId=8853&startDate=2025-12-05&endDate=2025-12-07&adults=2&lodging=VACATION_HOME&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Browse Select Middlesboro Vacation Homes ![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) ![Smart TV](https://images.trvl-media.com/lodging/114000000/113130000/113124900/113124803/3ea56b6c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/114000000/113130000/113124900/113124803/6668ab96.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/114000000/113130000/113124900/113124803/2b33c7e2.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 (16) "Our group had a wonderful time staying at Uncle Ernie's! Everything was neat, tidy, and felt like home. We definitely will be back next time we are in the area!" CA $166 CA $291 total includes taxes & fees Oct 14 - Oct 15 [](https://www.expedia.ca/Middlesboro-Hotels-Cozy-2-Bedroom-Lustron-Home-Located-In-Middlesboro.h113124803.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/120000000/119650000/119642400/119642383/509d4ba3.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 detail](https://images.trvl-media.com/lodging/120000000/119650000/119642400/119642383/2f2cc548.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/120000000/119650000/119642400/119642383/c9fc43d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Welcoming 3-bedroom house with AC in charming Middlesboro Middlesboro CA $139 CA $307 total includes taxes & fees Nov 4 - Nov 5 [](https://www.expedia.ca/Middlesboro-Hotels-Welcoming-3-Bedroom-House-With-AC-In-Charming-Middlesboro.h119642383.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/118000000/117740000/117736400/117736392/4228b014.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 CA $463 CA $758 total includes taxes & fees Oct 8 - Oct 9 [](https://www.expedia.ca/Middlesboro-Hotels-Spacious-Renovated-Ranch-Retreat-Near-Tackett-Creek-Cumberland-Gap-Park.h117736392.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/115000000/114380000/114371600/114371543/b67e5cbd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Game room](https://images.trvl-media.com/lodging/115000000/114380000/114371600/114371543/8ddfb60b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/115000000/114380000/114371600/114371543/w5885h4000x0y0-9ca9cc19.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/115000000/114380000/114371600/114371543/9e906acc_edited_2a47.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Charming 3-bedroom rustic cabin with WiFi in wonderful Williamsburg Williamsburg 10/10 Exceptional (5) "Beautiful home. Very nice location will stay here again " CA $258 CA $460 total includes taxes & fees Oct 9 - Oct 10 [](https://www.expedia.ca/Williamsburg-Hotels-Charming-3-Bedroom-Rustic-Cabin-With-WiFi-In-Wonderful-Williamsburg.h114371543.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) ![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) ![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) ### 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 $144 CA $317 total includes taxes & fees Oct 8 - Oct 9 [](https://www.expedia.ca/Harrogate-Hotels-Harrogate-Home-Mountain-Views-Dog-Friendly.h69638999.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/117000000/116290000/116285600/116285569/3f5b8647.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, DVD player](https://images.trvl-media.com/lodging/117000000/116290000/116285600/116285569/156e6af5.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/117000000/116290000/116285600/116285569/85a2072b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/117000000/116290000/116285600/116285569/51c80a93.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Charming 3-bedroom house with WiFi, AC in Pineville Kentucky Pineville 10/10 Exceptional (1) CA $176 CA $354 total includes taxes & fees Oct 14 - Oct 15 [](https://www.expedia.ca/Pineville-Hotels-Charming-3-Bedroom-House-With-WiFi.h116285569.Hotel-Information) ![Outdoor spa tub](https://images.trvl-media.com/lodging/116000000/115560000/115552800/115552722/fbb05550.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/116000000/115560000/115552800/115552722/w2999h1999x1y1-ba7966e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/116000000/115560000/115552800/115552722/w2954h1287x0y1-ff2e43a9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/116000000/115560000/115552800/115552722/05f72cb2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Serenity Villa: Luxurious Retreat with Hot Tub, Rooftop Deck & Mountain View's Sharps Chapel 10/10 Exceptional (3) "This was definitely the most romantic VRBO we’ve stayed at!!! Very clean, and the view from all of the balconies was incredible!!! " CA $196 CA $425 total includes taxes & fees Oct 16 - Oct 17 [](https://www.expedia.ca/Sharps-Chapel-Hotels-SERENITY-LUXE-1-Bedroom-Villa-In-Sharps-Chapel-With-Hot-Tub.h115552722.Hotel-Information) ![Comfort House | Private kitchen](https://images.trvl-media.com/lodging/105000000/104290000/104287200/104287199/fb66dac6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Comfort House | Bathroom](https://images.trvl-media.com/lodging/105000000/104290000/104287200/104287199/43f54380.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Comfort House | Living area](https://images.trvl-media.com/lodging/105000000/104290000/104287200/104287199/ceaca54c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Comfort House](https://images.trvl-media.com/lodging/105000000/104290000/104287200/104287199/edafc421.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The House on Park Avenue Pineville CA $405 CA $557 total includes taxes & fees Oct 8 - Oct 9 [](https://www.expedia.ca/Pineville-Hotels-The-House-On-Park-Avenue.h104287199.Hotel-Information) ![Living area](https://images.trvl-media.com/lodging/117000000/116170000/116163800/116163780/1485e752.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/117000000/116170000/116163800/116163780/602a2564.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, WiFi, bed sheets](https://images.trvl-media.com/lodging/117000000/116170000/116163800/116163780/d8442080.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Private kitchen](https://images.trvl-media.com/lodging/117000000/116170000/116163800/116163780/bc420e1b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Charming 2-bedroom bungalow with AC, WiFi in pleasant Pineville Pineville 10/10 Exceptional (1) "Well cared for property with nice upgrades! Perfect for our stay, everything we needed, and accommodating. " CA $257 CA $367 total includes taxes & fees Oct 9 - Oct 10 [](https://www.expedia.ca/Pineville-Hotels-Charming-2-Bedroom-Bungalow-With-AC.h116163780.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/34000000/33940000/33938700/33938643/d79c9131.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/34000000/33940000/33938700/33938643/59a30a63.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/34000000/33940000/33938700/33938643/47ae19bd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/34000000/33940000/33938700/33938643/2a23e329.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 1928 Home in the heart of Cumberland Gap Cumberland Gap 9.8/10 Exceptional (91) "Prominent house in historic Cumberland Gap.Family friendly and comfortable accommodations. Lots of different seating options inside and out. We would stay here again." CA $279 CA $356 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Cumberland-Gap-Hotels-1928-Home-In-The-Heart-Of-Cumberland-Gap.h33938643.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/106000000/105220000/105218200/105218118/d6836369.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books](https://images.trvl-media.com/lodging/106000000/105220000/105218200/105218118/252efc50.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/106000000/105220000/105218200/105218118/d098b403.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, free WiFi, bed sheets](https://images.trvl-media.com/lodging/106000000/105220000/105218200/105218118/88ac5e8c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Lake Escape at Powell Valley Marina LaFollette 9.8/10 Exceptional (7) "We were looking for easy access to Powell Valley Marina for our family. Very clean, really decorated nicely, just a little smaller than we expected but it worked for our 4 family members. I would definitely stay there again! We took our golf cart and could access the marina quickly!! " CA $339 CA $750 total includes taxes & fees Oct 8 - Oct 9 [](https://www.expedia.ca/La-Follette-Hotels-Escape-To-Serenity-At-Our-Charming-Lake-House-Retreat.h105218118.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/39000000/38440000/38431000/38430925/7748d7ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/39000000/38440000/38431000/38430925/48fe9af8.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) ![Game room](https://images.trvl-media.com/lodging/39000000/38440000/38431000/38430925/47d50a8f.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 $334 CA $1,012 total includes taxes & fees Oct 20 - Oct 21 [](https://www.expedia.ca/Caryville-Hotels-Brand-New-Norris-Lakefront-Custom-Home.h38430925.Hotel-Information) ![Private kitchen](https://images.trvl-media.com/lodging/114000000/113580000/113577000/113576917/fdd9fe83.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/114000000/113580000/113577000/113576917/61345510.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hair dryer, towels, soap, toilet paper](https://images.trvl-media.com/lodging/114000000/113580000/113577000/113576917/c25d045b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Private kitchen](https://images.trvl-media.com/lodging/114000000/113580000/113577000/113576917/5fc91e51.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 3-Bedroom Cottage, Peaceful setting, Close to Parks, 2 min. from Bell Theatre Pineville 4.8/10 (3) "I did not stay at this property due to a double booking. I stayed at a nearby house that needs to be cleaned better, specially the floors, a shower curtain needs to be added to the beautiful update in bathroom, some plates woukd be nice. House rules and check in, check out procedures, places to visit and eat nearby would have been helpful to have posted at the house. Overall was a decent place to stay, quiet neighborhood. I would at least consider staying again." CA $96 CA $289 total includes taxes & fees Oct 12 - Oct 13 [](https://www.expedia.ca/Pineville-Hotels-3-Bedroom-Cottage.h113576917.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=2025-10-21&endDate=2025-10-22®ionId=8853&adults=2&lodging=VACATION_HOME&sort=RECOMMENDED&openPlayBack=true) ![](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-Private-Vacation-Homes.d8853-aaPrivateVacationHomes.Travel-Guide-Accommodation)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FMiddlesboro-Private-Vacation-Homes.d8853-aaPrivateVacationHomes.Travel-Guide-Accommodation) ## Top Middlesboro Hotel Reviews ![Boone Trail Inn](//images.trvl-media.com/lodging/35000000/34980000/34978900/34978817/347cf131_y.jpg) ### Boone Trail Inn 10/10 Excellent "Fine." [](https://expedia.ca/Middlesboro-Hotels-Boone-Trail-Inn.h34978817.Hotel-Information) ![Rodeway Inn](//images.trvl-media.com/lodging/9000000/8450000/8445600/8445506/b7b25f30_y.jpg) ### Rodeway Inn 8/10 Good "It is a simple but decent room. " [](https://expedia.ca/Harlan-Hotels-Mount-Aire-Motel.h8445506.Hotel-Information) ![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) ![Pine Mountain State Resort Park](//images.trvl-media.com/lodging/2000000/1110000/1109500/1109434/75b8d155_y.jpg) ### Pine Mountain State Resort Park 10/10 Excellent "Room was nice, clean, and comfortable " [](https://expedia.ca/Corbin-Hotels-Pine-Mountain-State-Resort-Park.h1109434.Hotel-Information) ![Holiday Inn Express Williamsburg by IHG](//images.trvl-media.com/lodging/24000000/23250000/23240900/23240809/7b78ad82_y.jpg) ### Holiday Inn Express Williamsburg by IHG 10/10 Excellent "Nice room and location " [](https://expedia.ca/Corbin-Hotels-Holiday-Inn-Express-Williamsburg.h23240809.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) ## Find out more about Middlesboro ## Middlesboro Vacation Homes information | Number of reviews | | | --- | --- | | Accommodation | 181 Vacation Homes | | Lowest Price | CA $557 | | Highest Price | CA $557 | ## 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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