Title: The Best Middlebrook Hotels with Pools from $69 - Hotels with indoor pools in Middlebrook, VA | Expedia.com [Middlebrook Travel Guide](https://expedia.com/Middlebrook.dx3000460143)[Hotels in Middlebrook](https://expedia.com/Middlebrook-Hotels.d3000460143.Travel-Guide-Hotels)[Vacation Rentals in Middlebrook](https://expedia.com/Middlebrook-Vacation-Rentals.d3000460143.Travel-Guide-VacationRentals)[Flights to Middlebrook](https://expedia.com/Cheap-Flights-To-Middlebrook.d3000460143.Travel-Guide-Flights)[Car Rentals in Middlebrook](https://expedia.com/Car-Rentals-In-Middlebrook.d3000460143.Car-Rental-Guide)[Middlebrook Vacation Packages](https://expedia.com/Middlebrook.d3000460143.Destination-Travel-Guides) ![You don't always have to go far from home to find something beautiful…Love living in the Shenandoah Valley! #goldenhour](https://images.trvl-media.com/place/3000460143/b257e6c0-3730-483d-907f-cb4685eeec25.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Brittany Davidson ![](https://images.trvl-media.com/place/3000460143/b257e6c0-3730-483d-907f-cb4685eeec25.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ## Check availability on Middlebrook Hotels with a Pool Tonight [Mar 14 - Mar 15](https://www.expedia.com/Hotel-Search?regionId=3000460143&startDate=2026-03-14&endDate=2026-03-15&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Mar 15 - Mar 16](https://www.expedia.com/Hotel-Search?regionId=3000460143&startDate=2026-03-15&endDate=2026-03-16&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Mar 20 - Mar 22](https://www.expedia.com/Hotel-Search?regionId=3000460143&startDate=2026-03-20&endDate=2026-03-22&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Mar 27 - Mar 29](https://www.expedia.com/Hotel-Search?regionId=3000460143&startDate=2026-03-27&endDate=2026-03-29&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Middlebrook hotels with a pool ![Indoor pool](https://images.trvl-media.com/lodging/47000000/46550000/46550000/46549911/d94dad80.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/47000000/46550000/46550000/46549911/48cbd6cd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/47000000/46550000/46550000/46549911/8e95e8a0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Individually decorated, individually furnished, desk, laptop workspace](https://images.trvl-media.com/lodging/47000000/46550000/46550000/46549911/28c552f8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Express & Suites Staunton by IHG [](https://www.expedia.com/Staunton-Hotels-Holiday-Inn-Express-And-Suites-Staunton.h46549911.Hotel-Information) Staunton 9.6/10 Exceptional (953 reviews) - A splash of refreshment awaits with this stylish indoor pool for year-round swimming and hydromassage showers after a workout. $100 nightly $111 total Mar 19 - Mar 20 Total with taxes and fees [](https://www.expedia.com/Staunton-Hotels-Holiday-Inn-Express-And-Suites-Staunton.h46549911.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/69000000/68080000/68076800/68076715/25cf6aa0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/69000000/68080000/68076800/68076715/48c0e694.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/69000000/68080000/68076800/68076715/319b2ae2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/69000000/68080000/68076800/68076715/778c5b19.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Wintergreen. Sunset Vista Villa - Close to the ski slopes [](https://www.expedia.com/Charlottesville-Hotels-Stunning-Condo-Sunset-Vista-Villa.h68076715.Hotel-Information) Wintergreen Resort 10/10 Exceptional (104 reviews) $218 nightly $245 total Mar 15 - Mar 16 Total with taxes and fees [](https://www.expedia.com/Charlottesville-Hotels-Stunning-Condo-Sunset-Vista-Villa.h68076715.Hotel-Information) ![Pool](https://images.trvl-media.com/lodging/57000000/56550000/56543700/56543658/a870a931.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/57000000/56550000/56543700/56543658/dda1ec86.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/57000000/56550000/56543700/56543658/d5c938fc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/57000000/56550000/56543700/56543658/132f64a4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### New construction! 1 BD/2 BA Top of Wintergreen mountain. Sleeps 4, pet-friendly [](https://www.expedia.com/Charlottesville-Hotels-Pet-Friendly-Wintergreen-Piso-1BD-2BA-Reserva-Ahora-Para-La-Temporada-De-Esqui.h56543658.Hotel-Information) Roseland 9.6/10 Exceptional (148 reviews) - Mountain hideaway offers relaxation with sparkling pool and nearby hiking trails to explore. $215 nightly $241 total Mar 16 - Mar 17 Total with taxes and fees [](https://www.expedia.com/Charlottesville-Hotels-Pet-Friendly-Wintergreen-Piso-1BD-2BA-Reserva-Ahora-Para-La-Temporada-De-Esqui.h56543658.Hotel-Information) ![Smart TV, fireplace, books](https://images.trvl-media.com/lodging/89000000/88080000/88074700/88074679/c12a7e3c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/89000000/88080000/88074700/88074679/a15eafd3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/89000000/88080000/88074700/88074679/b6178f6d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/89000000/88080000/88074700/88074679/9b156d70.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Spacious + Serene Mtn Top Escape, 4 En Suites [](https://www.expedia.com/Nellysford-Hotels-Spacious-Serene-Mtn-Top-Escape.h88074679.Hotel-Information) Wintergreen Resort 10/10 Exceptional (50 reviews) $302 nightly $339 total Mar 15 - Mar 16 Total with taxes and fees [](https://www.expedia.com/Nellysford-Hotels-Spacious-Serene-Mtn-Top-Escape.h88074679.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/1000000/330000/328900/328834/4a6eb345.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fitness facility](https://images.trvl-media.com/lodging/1000000/330000/328900/328834/0f9cf6e8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 2 Queen Beds, Mountain View (Non Smoking) | In-room safe, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/1000000/330000/328900/328834/46be1d3a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Business center](https://images.trvl-media.com/lodging/1000000/330000/328900/328834/13def7d5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Clarion Pointe Staunton East [](https://www.expedia.com/Staunton-Hotels-Quality-Inn-Suites.h328834.Hotel-Information) Staunton 8.6/10 Excellent (1,000 reviews) - Soak in mountain views from the seasonal outdoor pool at this Staunton hotel where every splash becomes a scenic retreat. $74 nightly $83 total Mar 29 - Mar 30 Total with taxes and fees [](https://www.expedia.com/Staunton-Hotels-Quality-Inn-Suites.h328834.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/91000000/90090000/90087300/90087205/b0ffcdf7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, iron/ironing board, travel crib, WiFi](https://images.trvl-media.com/lodging/91000000/90090000/90087300/90087205/07c4a1b1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, books](https://images.trvl-media.com/lodging/91000000/90090000/90087300/90087205/02bbf7d3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/91000000/90090000/90087300/90087205/89b7b76d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Endless Mountain Top Views from All The Way Up! [](https://www.expedia.com/Nellysford-Hotels-Endless-Mountain-Top-Views-From-All-The-Way-Up.h90087205.Hotel-Information) Wintergreen Resort 10/10 Exceptional (98 reviews) $233 nightly $262 total Mar 15 - Mar 16 Total with taxes and fees [](https://www.expedia.com/Nellysford-Hotels-Endless-Mountain-Top-Views-From-All-The-Way-Up.h90087205.Hotel-Information) ![Fireplace](https://images.trvl-media.com/lodging/78000000/77100000/77096800/77096798/w1273h849x4y3-b64d948a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, iron/ironing board, travel crib, free WiFi](https://images.trvl-media.com/lodging/78000000/77100000/77096800/77096798/w1277h854x0y0-93eb93d7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fireplace](https://images.trvl-media.com/lodging/78000000/77100000/77096800/77096798/29fa29ea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/78000000/77100000/77096800/77096798/0d2cf0fc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Modern Mountain Condo [](https://www.expedia.com/Nellysford-Hotels-NEW-Modern-Mountain-Condo-WPool.h77096798.Hotel-Information) Wintergreen Resort 10/10 Exceptional (45 reviews) - Secluded swimming in private fenced pool at modern mountain condo, steps from Wintergreen Resort slopes. $204 nightly $229 total Mar 15 - Mar 16 Total with taxes and fees [](https://www.expedia.com/Nellysford-Hotels-NEW-Modern-Mountain-Condo-WPool.h77096798.Hotel-Information) ![Seasonal outdoor pool, open 9:00 AM to 10:00 PM, pool umbrellas](https://images.trvl-media.com/lodging/1000000/70000/64100/64084/60e202a8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/70000/64100/64084/83a5172c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 1 King Bed, Non Smoking | Desk, iron/ironing board, free cribs/infant beds, free WiFi](https://images.trvl-media.com/lodging/1000000/70000/64100/64084/249b11fa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/70000/64100/64084/9c6504ca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Comfort Inn Waynesboro [](https://www.expedia.com/Staunton-Hotels-Comfort-Inn.h64084.Hotel-Information) Waynesboro 8.4/10 Very Good (1,001 reviews) - Seasonal outdoor pool near Shenandoah National Park creates the perfect summer splash zone for adventurous travelers. $80 nightly $89 total Mar 22 - Mar 23 Total with taxes and fees [](https://www.expedia.com/Staunton-Hotels-Comfort-Inn.h64084.Hotel-Information) ![Pool](https://images.trvl-media.com/lodging/120000000/119310000/119304300/119304212/78b8767e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/120000000/119310000/119304300/119304212/w1003h683x0y0-5eec0b74.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/120000000/119310000/119304300/119304212/3f379aa5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/120000000/119310000/119304300/119304212/4ae5f81b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Laurelwood Hollow: Walk to Ski & Swim [](https://www.expedia.com/Nellysford-Hotels-Laurelwood-Hollow-Walk-To-Ski-Swim.h119304212.Hotel-Information) Wintergreen Resort 10/10 Exceptional (8 reviews) $265 nightly $279 total Mar 15 - Mar 16 Total with taxes and fees [](https://www.expedia.com/Nellysford-Hotels-Laurelwood-Hollow-Walk-To-Ski-Swim.h119304212.Hotel-Information) ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/1000000/30000/22300/22261/7a30cf5b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily full breakfast](https://images.trvl-media.com/lodging/1000000/30000/22300/22261/21ceb0a2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 1 King Bed, Non Smoking | Desk, laptop workspace, blackout drapes, iron/ironing board](https://images.trvl-media.com/lodging/1000000/30000/22300/22261/ad75a440.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/30000/22300/22261/ace96e1e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Quality Inn Waynesboro - Skyline Drive [](https://www.expedia.com/Staunton-Hotels-Quality-Inn-Waynesboro.h22261.Hotel-Information) Waynesboro 7.0/10 Good (838 reviews) - Seasonal outdoor pool offers refreshing summer swims near Shenandoah National Park, with mountain adventures awaiting nearby. $66 nightly $73 total Mar 22 - Mar 23 Total with taxes and fees [](https://www.expedia.com/Staunton-Hotels-Quality-Inn-Waynesboro.h22261.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.com/Hotel-Search?startDate=2026-03-28&endDate=2026-03-29®ionId=3000460143&adults=2&amenities=POOL&sort=RECOMMENDED&openPlayBack=true) ## Choose what matters most at hotels with a pool in Middlebrook Breakfast included 4 stars 5 stars Hot tub Spa ![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-us-ca.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## The Annual Vacation Sale Members save up to 40% on hotels and homes. Plan this year’s big trip and save. [Book now](https://expedia.com/deals?rfrr=AFFINITY_SPRING_PROMO_3000460143) ## Top Middlebrook Hotel Reviews ![Best Western Plus Waynesboro Inn & Suites Conference Center](https://images.trvl-media.com/lodging/2000000/1680000/1677400/1677369/b25accc7_y.jpg) ### Best Western Plus Waynesboro Inn & Suites Conference Center 8/10 Good "A friendly, comfortable, convenient, clean place to spend time on your journey. The provided breakfast was not stellar, but everything else was very very nice." [](https://expedia.com/Staunton-Hotels-Best-Western-Plus-Waynesboro-Inn-Suites-Conference-Center.h1677369.Hotel-Information) ![avid hotel Staunton by IHG](https://images.trvl-media.com/lodging/1000000/20000/17600/17558/5811eb8d_y.jpg) ### avid hotel Staunton by IHG 4/10 Poor "No hot water only warm water and water flow in shower very low. Wash Basin clogged one elevator out of order long wait time for moving up and down. We booked two rooms and paid $250 altogether its not worth it " [](https://expedia.com/Staunton-Hotels-Avid-Hotels-Staunton.h17558.Hotel-Information) ![Hampton Inn Lexington-Historic District](https://images.trvl-media.com/lodging/1000000/200000/199800/199780/092f8f99_y.jpg) ### Hampton Inn Lexington-Historic District 6/10 Okay "Coffee was really bad" [](https://expedia.com/Lexington-Hotels-Hampton-Inn-Lexington-Historic-District.h199780.Hotel-Information) ![Hotel 24 South](https://images.trvl-media.com/lodging/2000000/1320000/1311400/1311324/76d25ca1_y.jpg) ### Hotel 24 South 10/10 Excellent "The hotel was great " [](https://expedia.com/Staunton-Hotels-Hotel-24-South.h1311324.Hotel-Information) ![Holiday Inn Staunton Conference Center by IHG](https://images.trvl-media.com/lodging/1000000/20000/19200/19125/ca172168_y.jpg) ### Holiday Inn Staunton Conference Center by IHG 6/10 Okay "The pool area and pool were extremely cold " [](https://expedia.com/Staunton-Hotels-Holiday-Inn-Staunton-Conference-Center.h19125.Hotel-Information) ![Clarion Pointe Staunton East](https://images.trvl-media.com/lodging/1000000/330000/328900/328834/4a6eb345_y.jpg) ### Clarion Pointe Staunton East 6/10 Okay "Property was just ok. Good location, safe, and comfortable bed. Worst breakfast if you could call it breakfast. No cable tv on property. " [](https://expedia.com/Staunton-Hotels-Quality-Inn-Suites.h328834.Hotel-Information) ![Howard Johnson by Wyndham Lexington](https://images.trvl-media.com/lodging/1000000/20000/11000/10961/9f4afb55_y.jpg) ### Howard Johnson by Wyndham Lexington 8/10 Good "Room comfortable, sheer curtains are shredded, toilet is very short" [](https://expedia.com/Lexington-Hotels-Howard-Johnson-By-Wyndham-Lexington.h10961.Hotel-Information) ![Days Inn by Wyndham Staunton](https://images.trvl-media.com/lodging/1000000/30000/20600/20577/f55abd3f_y.jpg) ### Days Inn by Wyndham Staunton 8/10 Good "Very close in proximity to future travel plans. Breakfast had limited options." [](https://expedia.com/Staunton-Hotels-Days-Inn-By-Wyndham-Staunton.h20577.Hotel-Information) ## Frequently asked questions ### What are some accommodations with pools in Middlebrook? ### What is there to see and do in Middlebrook? ### When is the best time to book a hotel with a pool in Middlebrook? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rentals - [Greenville Hotels ](https://www.expedia.com/Greenville-Hotels.d3000460022.Travel-Guide-Hotels) - [Cabin Rentals in Greenville ](https://www.expedia.com/Greenville-Cabins.d3000460022-aaCabins.Travel-Guide-Accommodation) - [Motels in Greenville ](https://www.expedia.com/Greenville-Motels.d3000460022-aaMotels.Travel-Guide-Accommodation) - [Pet-Friendly Hotels in Mint Spring ](https://www.expedia.com/Mint-Spring-Hotels-Pet-Friendly-Hotel.0-0-d6348383-tPetfriendlyHotel.Travel-Guide-Filter-Hotels) - [Cheap Hotels in Mint Spring ](https://www.expedia.com/Mint-Spring-Hotels-Cheap-Hotels.0-0-d6348383-tCheapHotels.Travel-Guide-Filter-Hotels) - 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