Title: Best Apartments in Middletown, VA for Your Vacation from $186 | Expedia.com [Middletown Travel Guide](https://expedia.com/Middletown.dx12013)[Hotels in Middletown](https://expedia.com/Middletown-Hotels.d12013.Travel-Guide-Hotels)[Vacation Rentals in Middletown](https://expedia.com/Middletown-Vacation-Rentals.d12013.Travel-Guide-VacationRentals)[Flights to Middletown](https://expedia.com/Cheap-Flights-To-Middletown.d12013.Travel-Guide-Flights)[Car Rentals in Middletown](https://expedia.com/Car-Rentals-In-Middletown.d12013.Car-Rental-Guide)[Middletown Vacation Packages](https://expedia.com/Middletown.d12013.Destination-Travel-Guides) ![Beautiful drive up to this plantation. You can take a tour of it as well. ](https://images.trvl-media.com/place/6164020/0a9ca11f-dcc0-4ca9-affe-11fe2516dc02.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Stephanie Sutton ![](https://images.trvl-media.com/place/6164020/0a9ca11f-dcc0-4ca9-affe-11fe2516dc02.jpg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light_bundle_and_save.svg) ### Bundle & Save Get more, spend less whenever you see Bundle & Save deals - ![](https://a.travel-assets.com/travel-assets-manager/pictograms-expedia/light__onekey.svg) ### OneKeyCash Earn OneKeyCash on all your eligible bookings - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light_ftc.svg) ### Upfront pricing We are not like the others - we include taxes and fees ## Check prices for these dates In two weeks [Mar 13 - Mar 15](https://www.expedia.com/Hotel-Search?regionId=12013&startDate=2026-03-13&endDate=2026-03-15&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Apr 24 - Apr 26](https://www.expedia.com/Hotel-Search?regionId=12013&startDate=2026-04-24&endDate=2026-04-26&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [May 22 - May 24](https://www.expedia.com/Hotel-Search?regionId=12013&startDate=2026-05-22&endDate=2026-05-24&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [Jun 19 - Jun 21](https://www.expedia.com/Hotel-Search?regionId=12013&startDate=2026-06-19&endDate=2026-06-21&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Middletown apartments ![Terrace/patio](https://images.trvl-media.com/lodging/96000000/95130000/95120300/95120287/71b2e002.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Living area](https://images.trvl-media.com/lodging/96000000/95130000/95120300/95120287/e3d0040d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, stovetop, coffee/tea maker](https://images.trvl-media.com/lodging/96000000/95130000/95120300/95120287/ac41dd04.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, stovetop, coffee/tea maker](https://images.trvl-media.com/lodging/96000000/95130000/95120300/95120287/584db150.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cute Riverside Cabin w Hot Tub, Fire Pit, & Kayaks [](https://www.expedia.com/Rileyville-Hotels-Cute-Riverside-Cabin-W-Hot-Tub.h95120287.Hotel-Information) Luray 9.8/10 Exceptional (16 reviews) "It was an amazing place, will recommend to friends and hopefully will be back." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lucerito I. [](https://www.expedia.com/Rileyville-Hotels-Cute-Riverside-Cabin-W-Hot-Tub.h95120287.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/105000000/104060000/104052900/104052857/ba92ae27.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/105000000/104060000/104052900/104052857/9de8a9e6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/105000000/104060000/104052900/104052857/ca492496.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, DVD player, books](https://images.trvl-media.com/lodging/105000000/104060000/104052900/104052857/b7a39e49.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Apple Mountain Retreat [](https://www.expedia.com/Linden-Hotels-Apple-Mountain-Retreat.h104052857.Hotel-Information) Linden 10/10 Exceptional (21 reviews) "Great place to stayed " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Mike F. $206 nightly $227 total Mar 1 - Mar 2 Total with taxes and fees [](https://www.expedia.com/Linden-Hotels-Apple-Mountain-Retreat.h104052857.Hotel-Information) ![Smart TV](https://images.trvl-media.com/lodging/76000000/75860000/75852300/75852258/c7a94a89.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/76000000/75860000/75852300/75852258/902ff11e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/76000000/75860000/75852300/75852258/2359633a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/76000000/75860000/75852300/75852258/b00d8fd7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Nostalgia Lane in the heart of the city [](https://www.expedia.com/Winchester-Hotels-Nostalgia-Lane-In-The-Heart-Of-The-City.h75852258.Hotel-Information) Old Town Winchester 9.0/10 Wonderful (15 reviews) "Adorable place and perfect for Winchester and surrounding parks, wineries, and farms." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Tracy F. $293 nightly $332 total Mar 1 - Mar 2 Total with taxes and fees [](https://www.expedia.com/Winchester-Hotels-Nostalgia-Lane-In-The-Heart-Of-The-City.h75852258.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/110000000/109220000/109212000/109211934/ba7d038f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/110000000/109220000/109212000/109211934/ea8961d2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, stereo](https://images.trvl-media.com/lodging/110000000/109220000/109212000/109211934/05c27676.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, WiFi, bed sheets](https://images.trvl-media.com/lodging/110000000/109220000/109212000/109211934/88deda1a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Luxe 2 Bed Dome w Hot Tub, Deck, Fire Pit & Bath [](https://www.expedia.com/Augusta-Hotels-Luxe-2-Bed-Dome-W-Hot-Tub.h109211934.Hotel-Information) Augusta 7.4/10 Good (3 reviews) "Great Experience!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kimberly B. $246 nightly $263 total Mar 2 - Mar 3 Total with taxes and fees [](https://www.expedia.com/Augusta-Hotels-Luxe-2-Bed-Dome-W-Hot-Tub.h109211934.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/121000000/120420000/120414100/120414068/5c313978.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/121000000/120420000/120414100/120414068/8a7ae46b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/121000000/120420000/120414100/120414068/f803f4c1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/121000000/120420000/120414100/120414068/07dac09c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### NEW! Historic Schoolhouse HotTub+FirePit+Wineries [](https://www.expedia.com/Linden-Hotels-NEW-Historic-Schoolhouse-HotTubFirePitWineries.h120414068.Hotel-Information) Fauquier County 8.0/10 Very Good (1 review) "The listing indicated pets were welcome and we were able to bring our 13 year old dog, who loves traveling with my husband and I. There was some initial confusion after we booked the Schoolhouse, saying pets are prohibited. Through contact with the host, it was cleared up pretty quickly. All in all, the place was comfortable and we had what we needed to cook a couple of meals. I loved the area and enjoyed walking our dog on the state-maintained back roads. We would have liked to take advantage... ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kathy S. $289 nightly $291 total Mar 4 - Mar 5 Total with taxes and fees [](https://www.expedia.com/Linden-Hotels-NEW-Historic-Schoolhouse-HotTubFirePitWineries.h120414068.Hotel-Information) ![Exterior detail](https://images.trvl-media.com/lodging/76000000/75860000/75854400/75854350/w1080h1606x0y6-7da3475e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/76000000/75860000/75854400/75854350/d01496c8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/76000000/75860000/75854400/75854350/58d1022d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/76000000/75860000/75854400/75854350/43e19b3c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Stock Exchange downtown 3rd floor studio apt [](https://www.expedia.com/Winchester-Hotels-The-Stock-Exchange-Downtown-3rd-Floor-Studio-Apt.h75854350.Hotel-Information) Winchester Historic District 6.0/10 (1 review) $175 nightly $198 total Mar 1 - Mar 2 Total with taxes and fees [](https://www.expedia.com/Winchester-Hotels-The-Stock-Exchange-Downtown-3rd-Floor-Studio-Apt.h75854350.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/120000000/119540000/119530500/119530464/w506h683x260y0-1afec896.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/120000000/119540000/119530500/119530464/3aaa43b1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, iron/ironing board, internet, bed sheets](https://images.trvl-media.com/lodging/120000000/119540000/119530500/119530464/ff2d50c8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/120000000/119540000/119530500/119530464/w506h683x259y0-d4dd74ae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Very charming & spacious 2 bedrm [](https://www.expedia.com/Winchester-Hotels-Very-Charming-Spacious-2-Bedrm.h119530464.Hotel-Information) Winchester $171 nightly $186 total Mar 1 - Mar 2 Total with taxes and fees [](https://www.expedia.com/Winchester-Hotels-Very-Charming-Spacious-2-Bedrm.h119530464.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/90000000/89720000/89710300/89710219/238a8931.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/90000000/89720000/89710300/89710219/4e22f1f8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/90000000/89720000/89710300/89710219/afd55d63.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![WiFi, bed sheets](https://images.trvl-media.com/lodging/90000000/89720000/89710300/89710219/9390f2d3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Riverside Tiny Cabin w Hot Tub, Fire Pit, & Kayaks [](https://www.expedia.com/Rileyville-Hotels-Riverside-Tiny-Cabin-W-Hot-Tub.h89710219.Hotel-Information) Luray 10/10 Exceptional (8 reviews) "We had a wonderful time, loved the location and space! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jennifer C. $246 nightly $271 total Mar 3 - Mar 4 Total with taxes and fees [](https://www.expedia.com/Rileyville-Hotels-Riverside-Tiny-Cabin-W-Hot-Tub.h89710219.Hotel-Information) ![Smart TV, books](https://images.trvl-media.com/lodging/106000000/105770000/105765500/105765423/6b26f42f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/106000000/105770000/105765500/105765423/6b64b57e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/106000000/105770000/105765500/105765423/2f99002c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books](https://images.trvl-media.com/lodging/106000000/105770000/105765500/105765423/dce8d0ff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Dreamweaver — 1BR 1BA just two blocks from the downtown walking mall [](https://www.expedia.com/Winchester-Hotels-Dreamweaver-1BR-1BA-Just-Two-Blocks-From-The-Downtown-Walking-Mall.h105765423.Hotel-Information) Winchester Historic District 8.6/10 Excellent (4 reviews) "Large historic house at a great location " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Bryan T. $203 nightly $230 total Mar 1 - Mar 2 Total with taxes and fees [](https://www.expedia.com/Winchester-Hotels-Dreamweaver-1BR-1BA-Just-Two-Blocks-From-The-Downtown-Walking-Mall.h105765423.Hotel-Information) ![Outdoor spa tub](https://images.trvl-media.com/lodging/97000000/96990000/96989300/96989203/612baaa7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, coffee/tea maker, cookware/dishes/utensils](https://images.trvl-media.com/lodging/97000000/96990000/96989300/96989203/99c2fb1f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/97000000/96990000/96989300/96989203/7d203bc0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/97000000/96990000/96989300/96989203/52dfe9bd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Glamping dome w/hot tub & mountain views [](https://www.expedia.com/Augusta-Hotels-Elegant-Rustic-Glamping-Dome-With-Mountain-View.h96989203.Hotel-Information) Augusta 10/10 Exceptional (8 reviews) "Wonderful stay!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Eli W. $237 nightly $253 total Mar 3 - Mar 4 Total with taxes and fees [](https://www.expedia.com/Augusta-Hotels-Elegant-Rustic-Glamping-Dome-With-Mountain-View.h96989203.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/108000000/107500000/107496600/107496576/bf31b57d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, stovetop, coffee/tea maker](https://images.trvl-media.com/lodging/108000000/107500000/107496600/107496576/91c69128.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/108000000/107500000/107496600/107496576/a6829ebe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/108000000/107500000/107496600/107496576/e0ef6707.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Glamping dome w/hot tub & fire pit [](https://www.expedia.com/Augusta-Hotels-Luxe-Dome-W-Hot-Tub.h107496576.Hotel-Information) Augusta 9.2/10 Wonderful (5 reviews) "This property was really cool to stay at. Nice and cozy with everything needed for a comfortable stay. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Brandy B. $246 nightly $263 total Mar 3 - Mar 4 Total with taxes and fees [](https://www.expedia.com/Augusta-Hotels-Luxe-Dome-W-Hot-Tub.h107496576.Hotel-Information) ![Smart TV](https://images.trvl-media.com/lodging/76000000/75860000/75856800/75856721/547de25c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/76000000/75860000/75856800/75856721/765a953b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/76000000/75860000/75856800/75856721/38fc952e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/76000000/75860000/75856800/75856721/6e61e0ea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Yellow Submarine trendy basement apt and courtyard [](https://www.expedia.com/Winchester-Hotels-Yellow-Submarine-Trendy-Basement-Apt-And-Courtyard.h75856721.Hotel-Information) Old Town Winchester 7.6/10 Good (4 reviews) "We loved the character and personality kf both Winchester and" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jenna N. $223 nightly $253 total Mar 17 - Mar 18 Total with taxes and fees [](https://www.expedia.com/Winchester-Hotels-Yellow-Submarine-Trendy-Basement-Apt-And-Courtyard.h75856721.Hotel-Information) ![Dining](https://images.trvl-media.com/lodging/76000000/75860000/75856500/75856493/80b59f6e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/76000000/75860000/75856500/75856493/2c3dcc54.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/76000000/75860000/75856500/75856493/31a46244.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/76000000/75860000/75856500/75856493/w1413h1055x0y0-6561893b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### WonderClock House downtown vintage duplex w/ porches, steps to Handley Library [](https://www.expedia.com/Winchester-Hotels-WonderClock-House-Downtown-Vintage-Duplex-W-Porches.h75856493.Hotel-Information) Old Town Winchester 9.0/10 Wonderful (6 reviews) "Indigo Blue is in a beautiful neighborhood and we loved the house and location!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Tricia M. $317 nightly $359 total Mar 1 - Mar 2 Total with taxes and fees [](https://www.expedia.com/Winchester-Hotels-WonderClock-House-Downtown-Vintage-Duplex-W-Porches.h75856493.Hotel-Information) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/76000000/75860000/75853600/75853509/e0ae9bc5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/76000000/75860000/75853600/75853509/49b61b8d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/76000000/75860000/75853600/75853509/aac25142.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/76000000/75860000/75853600/75853509/e55c3864.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Scarborough Fair walk to downtown two story apt [](https://www.expedia.com/Winchester-Hotels-Scarborough-Fair-Walk-To-Downtown-Two-Story-Apt.h75853509.Hotel-Information) Old Town Winchester 9.8/10 Exceptional (6 reviews) "Excellent location, easy walk to most of the Old Town area. Michele is a great host, will definitely stay here again if in the area. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Larry E. $346 nightly $392 total Mar 2 - Mar 3 Total with taxes and fees [](https://www.expedia.com/Winchester-Hotels-Scarborough-Fair-Walk-To-Downtown-Two-Story-Apt.h75853509.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/120000000/119110000/119109900/119109888/9e880709.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Microwave, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/120000000/119110000/119109900/119109888/2888dcd1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/120000000/119110000/119109900/119109888/e0865dce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/120000000/119110000/119109900/119109888/bd1270e6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Magnolia Wind elegant 3 BR 1BA loft apartment park for free and walk downtown [](https://www.expedia.com/Winchester-Hotels-Magnolia-Wind-Elegant-3-BR-1BA-Loft-Apartment-Park-For-Free-And-Walk-Downtown.h119109888.Hotel-Information) Old Town Winchester 10/10 Exceptional (2 reviews) "Beautiful space; helpful host." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Sally C. $344 nightly $390 total Mar 15 - Mar 16 Total with taxes and fees [](https://www.expedia.com/Winchester-Hotels-Magnolia-Wind-Elegant-3-BR-1BA-Loft-Apartment-Park-For-Free-And-Walk-Downtown.h119109888.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=2026-03-14&endDate=2026-03-15®ionId=12013&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true) ![](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=AA_SPRING_PROMO_12013) ## Find vacation rentals that suit your style Cabins [](https://www.expedia.com/Hotel-Search?destination=Middletown%2C+Virginia%2C+United+States+of+America®ionId=12013&latLong=39.027608%2C-78.280558&adults=2&startDate=2026-05-28&d1=2026-05-28&endDate=2026-05-31&d2=2026-05-31&lodging=CABIN) Cottages [](https://www.expedia.com/Hotel-Search?destination=Middletown%2C+Virginia%2C+United+States+of+America®ionId=12013&latLong=39.027608%2C-78.280558&adults=2&startDate=2026-05-28&d1=2026-05-28&endDate=2026-05-31&d2=2026-05-31&lodging=COTTAGE) Private vacation homes [](https://www.expedia.com/Hotel-Search?destination=Middletown%2C+Virginia%2C+United+States+of+America®ionId=12013&latLong=39.027608%2C-78.280558&adults=2&startDate=2026-05-28&d1=2026-05-28&endDate=2026-05-31&d2=2026-05-31&lodging=VACATION_HOME) Apartments [](https://www.expedia.com/Hotel-Search?destination=Middletown%2C+Virginia%2C+United+States+of+America®ionId=12013&latLong=39.027608%2C-78.280558&adults=2&startDate=2026-05-28&d1=2026-05-28&endDate=2026-05-31&d2=2026-05-31&lodging=APARTMENT) Chalets [](https://www.expedia.com/Hotel-Search?destination=Middletown%2C+Virginia%2C+United+States+of+America®ionId=12013&latLong=39.027608%2C-78.280558&adults=2&startDate=2026-05-28&d1=2026-05-28&endDate=2026-05-31&d2=2026-05-31&lodging=CHALET) Villas [](https://www.expedia.com/Hotel-Search?destination=Middletown%2C+Virginia%2C+United+States+of+America®ionId=12013&latLong=39.027608%2C-78.280558&adults=2&startDate=2026-05-28&d1=2026-05-28&endDate=2026-05-31&d2=2026-05-31&lodging=VILLA) ![](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.com/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FMiddletown-Apartments.d12013-aaApartments.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.com/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FMiddletown-Apartments.d12013-aaApartments.Travel-Guide-Accommodation) ## Top Middletown Hotel Reviews ![Comfort Inn & Suites Winchester](https://images.trvl-media.com/lodging/58000000/57960000/57958300/57958244/cf4c2663_y.jpg) ### Comfort Inn & Suites Winchester 10/10 Excellent "The room was clean and the staff was very accommodating" [](https://expedia.com/Winchester-Hotels-Comfort-Inn-Suites.h57958244.Hotel-Information) ![La Quinta Inn & Suites by Wyndham Winchester](https://images.trvl-media.com/lodging/3000000/2680000/2678600/2678524/3336c7bb_y.jpg) ### La Quinta Inn & Suites by Wyndham Winchester 10/10 Excellent "Nice facility, nice staff, and comfortable clean room. Superior exercise room. Suggest removing broken/non-functioning bottle fed water cooler in exercise room and having signage direct guests to water fountain “just around the corner by the elevator.“ Warm breakfast adequate and served in very comfortable, bright area. The only bill downside was fellow guests who were traveling with dogs. Despite the hotel, providing waste bags, prominently and posting signs asking guests to “pick up after your dog, please,” there was a grotesque amount of dog droppings all around the hotel exterior." [](https://expedia.com/Winchester-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Winchester.h2678524.Hotel-Information) ![Microtel Inn & Suites by Wyndham Winchester](https://images.trvl-media.com/lodging/71000000/70930000/70921100/70921061/fab1f657_y.jpg) ### Microtel Inn & Suites by Wyndham Winchester 10/10 Excellent "Room was clean and it was easy to check in. Breakfast in the morning was good and easy to check out also." [](https://expedia.com/Winchester-Hotels-Microtel-Inn-Suites-By-Wyndham-Winchester.h70921061.Hotel-Information) ![Travelodge by Wyndham Winchester](https://images.trvl-media.com/lodging/1000000/10000/9600/9600/9d44a9b1_y.jpg) ### Travelodge by Wyndham Winchester 10/10 Excellent "Room was spacious, bed was comfortable and lots of TV channels. Gentleman that checked us in and out was very courteous." [](https://expedia.com/Winchester-Hotels-Travelodge-By-Wyndham-Winchester.h9600.Hotel-Information) ![SpringHill Suites by Marriott Winchester](https://images.trvl-media.com/lodging/43000000/42550000/42543800/42543772/193cda05_y.jpg) ### SpringHill Suites by Marriott Winchester 10/10 Excellent "The pool was warm, and everything was very clean. The staff were also great! " [](https://expedia.com/Winchester-Hotels-SpringHill-Suites-By-Marriott-Winchester.h42543772.Hotel-Information) ![Holiday Inn Winchester Se-Historic Gateway by IHG](https://images.trvl-media.com/lodging/2000000/1890000/1889100/1889084/c68804b2_y.jpg) ### Holiday Inn Winchester Se-Historic Gateway by IHG 10/10 Excellent "201 " [](https://expedia.com/Winchester-Hotels-Holiday-Inn-Winchester-Se-Historic-Gateway.h1889084.Hotel-Information) ![Sleep Inn & Suites Winchester near University](https://images.trvl-media.com/lodging/1000000/900000/892900/892882/53b7b275_y.jpg) ### Sleep Inn & Suites Winchester near University 10/10 Excellent "Room was clean " [](https://expedia.com/Winchester-Hotels-Sleep-Inn-Suites.h892882.Hotel-Information) ![The George Washington Hotel, A Wyndham Grand Hotel](https://images.trvl-media.com/lodging/2000000/1370000/1364100/1364026/5a07226c_y.jpg) ### The George Washington Hotel, A Wyndham Grand Hotel 10/10 Excellent "Fantastic " [](https://expedia.com/Winchester-Hotels-The-George-Washington-Hotel.h1364026.Hotel-Information) ![Falling Leaf Cabin - Rustic Charm With Modern Decor!](https://images.trvl-media.com/lodging/34000000/33750000/33748300/33748224/e001c092_y.jpg) ### Falling Leaf Cabin - Rustic Charm With Modern Decor! 10/10 Excellent "The cabin was cozy and warm in this wintry weather. The host was easy to communicate with and everything went smoothly." [](https://expedia.com/Rileyville-Hotels-Falling-Leaf-Cabin-Secluded-With-Mountain-View.h33748224.Hotel-Information) ## Find out more about Middletown ## Middletown Apartments information | Number of reviews | 78 | | ----------------- | ------------- | | Accommodation | 58 Apartments | | Lowest Price | $186 | | Highest Price | $392 | ## Frequently asked questions ### What's it like to stay at an apartment in Middletown? ### Are you thinking about apartments over traditional hotel rooms? ### What's a favorite apartment I should consider for a stay in Middletown? ### What can I expect from the weather when I travel to Middletown? ### What are the must-see places to visit in Middletown? ### What's the best way to get to and around Middletown? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rentals - [Hotels near Wayside Theater ](https://www.expedia.com/Wayside-Theater-Hotels.0-l6164044-0.Travel-Guide-Filter-Hotels) - [Hotels near Cedar Creek and Belle Grove National Historical Park ](https://www.expedia.com/Cedar-Creek-And-Belle-Grove-National-Historical-Park-Hotels.0-l6093271-0.Travel-Guide-Filter-Hotels) - 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