Title: Middletown Apartment Rentals from CA $197 | Expedia.ca [Hotels in Middletown](https://expedia.ca/Middletown-Hotels.d12013.Travel-Guide-Hotels)[Vacation Rentals in Middletown](https://expedia.ca/Middletown-Vacation-Rentals.d12013.Travel-Guide-VacationRentals)[Middletown Car Rentals](https://expedia.ca/Car-Rentals-In-Middletown.d12013.Car-Rental-Guide)[Middletown Vacation Packages](https://expedia.ca/Middletown.d12013.Destination-Travel-Guides) ![Nana’s Irish Pub was a great and delicious stop off the main road on the way to Asheville, NC. Super cute redesigned bank. The bank door is still in the corner and is not a closet. Highly suggested for a pit stop!](https://images.trvl-media.com/place/12013/db58f126-7d10-4018-a689-28fc2b700f21.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Samantha Keyes # Search Apartment Rentals in Middletown - ![](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 26 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=12013&startDate=2025-12-26&endDate=2025-12-28&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Feb 6 - Feb 8](https://www.expedia.ca/Hotel-Search?regionId=12013&startDate=2026-02-06&endDate=2026-02-08&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [Mar 6 - Mar 8](https://www.expedia.ca/Hotel-Search?regionId=12013&startDate=2026-03-06&endDate=2026-03-08&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [Apr 3 - Apr 5](https://www.expedia.ca/Hotel-Search?regionId=12013&startDate=2026-04-03&endDate=2026-04-05&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 ![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) ![Interior](https://images.trvl-media.com/lodging/120000000/119540000/119530500/119530464/w507h683x259y0-313a4f70.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Very charming & spacious 2 bedrm [](https://www.expedia.ca/Winchester-Hotels-Very-Charming-Spacious-2-Bedrm.h119530464.Hotel-Information) Winchester CA $84 CA $197 total includes taxes & fees Dec 21 - Dec 22 [](https://www.expedia.ca/Winchester-Hotels-Very-Charming-Spacious-2-Bedrm.h119530464.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/108000000/107220000/107216300/107216300/w1118h1128x0y0-c29ed3e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/108000000/107220000/107216300/107216300/w1133h1513x0y23-fd248447.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/108000000/107220000/107216300/107216300/a601c23d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/108000000/107220000/107216300/107216300/w1136h1516x18y15-0867a003.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Rosamond nice downtown studio apt [](https://www.expedia.ca/Winchester-Hotels-Rosamond-Nice-Downtown-Studio-Apt.h107216300.Hotel-Information) Winchester Historic District 8.0/10 Very good (2) "Small but appropriately priced." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) John M. CA $152 CA $265 total includes taxes & fees Dec 15 - Dec 16 [](https://www.expedia.ca/Winchester-Hotels-Rosamond-Nice-Downtown-Studio-Apt.h107216300.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/96000000/95130000/95120300/95120287/0f1edc47.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/ed85aff9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/96000000/95130000/95120300/95120287/c68904c2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Living area](https://images.trvl-media.com/lodging/96000000/95130000/95120300/95120287/da43d08d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cute Riverside Cabin w Hot Tub, Fire Pit, & Kayaks [](https://www.expedia.ca/Rileyville-Hotels-Cute-Riverside-Cabin-W-Hot-Tub.h95120287.Hotel-Information) Luray 9.8/10 Exceptional (15) "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. CA $203 CA $329 total includes taxes & fees Dec 15 - Dec 16 [](https://www.expedia.ca/Rileyville-Hotels-Cute-Riverside-Cabin-W-Hot-Tub.h95120287.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/105000000/104060000/104052900/104052857/10901b08.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/105000000/104060000/104052900/104052857/4f7ea815.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/105000000/104060000/104052900/104052857/1592611e.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.ca/Linden-Hotels-Apple-Mountain-Retreat.h104052857.Hotel-Information) Linden 10/10 Exceptional (21) "Great place to stayed " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Mike F. CA $186 CA $319 total includes taxes & fees Dec 13 - Dec 14 [](https://www.expedia.ca/Linden-Hotels-Apple-Mountain-Retreat.h104052857.Hotel-Information) ![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) ![Outdoor dining](https://images.trvl-media.com/lodging/110000000/109220000/109212000/109211934/f0c1a8f5.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) ![Microwave, stovetop, coffee/tea maker, toaster](https://images.trvl-media.com/lodging/110000000/109220000/109212000/109211934/62b27a0b.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.ca/Augusta-Hotels-Luxe-2-Bed-Dome-W-Hot-Tub.h109211934.Hotel-Information) Augusta 7.4/10 Good (3) "Great Experience!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kimberly B. CA $224 CA $388 total includes taxes & fees Dec 14 - Dec 15 [](https://www.expedia.ca/Augusta-Hotels-Luxe-2-Bed-Dome-W-Hot-Tub.h109211934.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/122000000/121940000/121935800/121935788/0f5f7b29.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/122000000/121940000/121935800/121935788/642d5e7f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/122000000/121940000/121935800/121935788/36f6e97c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/122000000/121940000/121935800/121935788/02c6ece4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Farm Suite at Valley View Farm [](https://www.expedia.ca/Farm-Suite-At-Valley-View-Farm.h121935788.Hotel-Information) Delaplane CA $241 CA $462 total includes taxes & fees Dec 15 - Dec 16 [](https://www.expedia.ca/Farm-Suite-At-Valley-View-Farm.h121935788.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/90000000/89720000/89710300/89710219/29cb87aa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/90000000/89720000/89710300/89710219/d6a5e58a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![WiFi, bed sheets](https://images.trvl-media.com/lodging/90000000/89720000/89710300/89710219/f2908503.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/90000000/89720000/89710300/89710219/791d3a32.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Riverside Tiny Cabin w Hot Tub, Fire Pit, & Kayaks [](https://www.expedia.ca/Rileyville-Hotels-Riverside-Tiny-Cabin-W-Hot-Tub.h89710219.Hotel-Information) Luray 10/10 Exceptional (8) "We had a wonderful time, loved the location and space! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jennifer C. CA $233 CA $376 total includes taxes & fees Jan 12 - Jan 13, 2026 [](https://www.expedia.ca/Rileyville-Hotels-Riverside-Tiny-Cabin-W-Hot-Tub.h89710219.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/106000000/105770000/105765500/105765423/01fca712.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/106000000/105770000/105765500/105765423/854ec4d2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![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) ![Smart TV, books](https://images.trvl-media.com/lodging/106000000/105770000/105765500/105765423/2ce760e6.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.ca/Winchester-Hotels-Dreamweaver-1BR-1BA-Just-Two-Blocks-From-The-Downtown-Walking-Mall.h105765423.Hotel-Information) Winchester Historic District 8.6/10 Excellent (4) "Clean property. Convenient to Old Town Winchester. All and all good property. Needs new bedroom pillows. Best." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) matthew r. CA $190 CA $325 total includes taxes & fees Dec 29 - Dec 30 [](https://www.expedia.ca/Winchester-Hotels-Dreamweaver-1BR-1BA-Just-Two-Blocks-From-The-Downtown-Walking-Mall.h105765423.Hotel-Information) ![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) ![Smart TV](https://images.trvl-media.com/lodging/76000000/75860000/75856800/75856721/85465173.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/76000000/75860000/75856800/75856721/fe22c400.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/76000000/75860000/75856800/75856721/547de25c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Yellow Submarine trendy basement apt and courtyard [](https://www.expedia.ca/Winchester-Hotels-Yellow-Submarine-Trendy-Basement-Apt-And-Courtyard.h75856721.Hotel-Information) Old Town Winchester 7.6/10 Good (4) "We loved the character and personality kf both Winchester and" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jenna N. CA $201 CA $354 total includes taxes & fees Dec 15 - Dec 16 [](https://www.expedia.ca/Winchester-Hotels-Yellow-Submarine-Trendy-Basement-Apt-And-Courtyard.h75856721.Hotel-Information) ![1 bedroom, WiFi, bed sheets](https://images.trvl-media.com/lodging/97000000/96990000/96989300/96989203/5741b6bb.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/97000000/96990000/96989300/96989203/05b3e175.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/97000000/96990000/96989300/96989203/98dc2745.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/97000000/96990000/96989300/96989203/726e96cb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Luxe Dome w/ Hot Tub, Full Bath & Mountain View! [](https://www.expedia.ca/Augusta-Hotels-Elegant-Rustic-Glamping-Dome-With-Mountain-View.h96989203.Hotel-Information) Augusta 10/10 Exceptional (6) "Fabulous, will visit again" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) H D S. CA $244 CA $398 total includes taxes & fees Dec 18 - Dec 19 [](https://www.expedia.ca/Augusta-Hotels-Elegant-Rustic-Glamping-Dome-With-Mountain-View.h96989203.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/123000000/122200000/122198800/122198726/2ac6665f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/123000000/122200000/122198800/122198726/4002ed32.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, WiFi, bed sheets](https://images.trvl-media.com/lodging/123000000/122200000/122198800/122198726/737919cb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, stereo](https://images.trvl-media.com/lodging/123000000/122200000/122198800/122198726/394b5537.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Glamping Dome w/Fire Pit, WiFi, King Bed & Bath [](https://www.expedia.ca/Wardensville-Hotels-Glamping-Dome-WFire-Pit.h122198726.Hotel-Information) Wardensville CA $235 CA $423 total includes taxes & fees Dec 15 - Dec 16 [](https://www.expedia.ca/Wardensville-Hotels-Glamping-Dome-WFire-Pit.h122198726.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) ![Property grounds](https://images.trvl-media.com/lodging/76000000/75860000/75856500/75856493/cf8e60e5.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) ![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.ca/Winchester-Hotels-WonderClock-House-Downtown-Vintage-Duplex-W-Porches.h75856493.Hotel-Information) Old Town Winchester 9.0/10 Wonderful (6) "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. CA $282 CA $510 total includes taxes & fees Dec 15 - Dec 16 [](https://www.expedia.ca/Winchester-Hotels-WonderClock-House-Downtown-Vintage-Duplex-W-Porches.h75856493.Hotel-Information) ![3 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/76000000/75860000/75852300/75852258/434367ca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/76000000/75860000/75852300/75852258/ace40b05.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) ![Dining](https://images.trvl-media.com/lodging/76000000/75860000/75852300/75852258/4cf065b7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Nostalgia Lane in the heart of the city [](https://www.expedia.ca/Winchester-Hotels-Nostalgia-Lane-In-The-Heart-Of-The-City.h75852258.Hotel-Information) Old Town Winchester 9.0/10 Wonderful (14) "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. CA $255 CA $457 total includes taxes & fees Dec 15 - Dec 16 [](https://www.expedia.ca/Winchester-Hotels-Nostalgia-Lane-In-The-Heart-Of-The-City.h75852258.Hotel-Information) ![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) ![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) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/76000000/75860000/75854400/75854350/5e1231b8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/76000000/75860000/75854400/75854350/9ba529c6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Stock Exchange downtown 3rd floor studio apt [](https://www.expedia.ca/Winchester-Hotels-The-Stock-Exchange-Downtown-3rd-Floor-Studio-Apt.h75854350.Hotel-Information) Winchester Historic District 6.0/10 (1) CA $152 CA $273 total includes taxes & fees Dec 18 - Dec 19 [](https://www.expedia.ca/Winchester-Hotels-The-Stock-Exchange-Downtown-3rd-Floor-Studio-Apt.h75854350.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/108000000/107500000/107496600/107496576/25437ca7.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/bd1f4538.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/108000000/107500000/107496600/107496576/70ef8503.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/108000000/107500000/107496600/107496576/593eb66c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Luxe Dome w Hot Tub, King Bed, Full Bath & FirePit [](https://www.expedia.ca/Augusta-Hotels-Luxe-Dome-W-Hot-Tub.h107496576.Hotel-Information) Augusta 9.2/10 Wonderful (5) "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. CA $245 CA $447 total includes taxes & fees Dec 16 - Dec 17 [](https://www.expedia.ca/Augusta-Hotels-Luxe-Dome-W-Hot-Tub.h107496576.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/76000000/75860000/75853600/75853509/49b61b8d.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/76000000/75860000/75853600/75853509/b3502d94.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![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) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/76000000/75860000/75853600/75853509/facc3b4a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Scarborough Fair walk to downtown two story apt [](https://www.expedia.ca/Winchester-Hotels-Scarborough-Fair-Walk-To-Downtown-Two-Story-Apt.h75853509.Hotel-Information) Old Town Winchester 9.6/10 Exceptional (5) "Charming home! Lovely decor. Was perfect for our stay. Great location, walkable to the historical district. Host was very friendly and communicative. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Stephanie L. CA $306 CA $545 total includes taxes & fees Dec 29 - Dec 30 [](https://www.expedia.ca/Winchester-Hotels-Scarborough-Fair-Walk-To-Downtown-Two-Story-Apt.h75853509.Hotel-Information) ![Microwave, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/120000000/119110000/119109900/119109888/bb213bf2.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/b8efa464.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/120000000/119110000/119109900/119109888/23f512b0.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.ca/Winchester-Hotels-Magnolia-Wind-Elegant-3-BR-1BA-Loft-Apartment-Park-For-Free-And-Walk-Downtown.h119109888.Hotel-Information) Old Town Winchester CA $303 CA $529 total includes taxes & fees Dec 15 - Dec 16 [](https://www.expedia.ca/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.ca/Hotel-Search?startDate=2025-12-26&endDate=2025-12-27®ionId=12013&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&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%2FMiddletown-Apartments.d12013-aaApartments.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FMiddletown-Apartments.d12013-aaApartments.Travel-Guide-Accommodation) ## Top Middletown Hotel Reviews ![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 "The room was clean and the bed was comfortable. My only desire is for firmer, foam pillows and brighter lights at the vanity. The staff is always efficient and friendly. It’s a beautiful hotel and we always have a good time at the bar!" [](https://expedia.ca/Winchester-Hotels-The-George-Washington-Hotel.h1364026.Hotel-Information) ![Hampton Inn Front Royal](https://images.trvl-media.com/lodging/1000000/900000/892600/892585/737257e0_y.jpg) ### Hampton Inn Front Royal 10/10 Excellent "All great " [](https://expedia.ca/Winchester-Hotels-Hampton-Inn-Front-Royal.h892585.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 "Clean room , wonderful front staff. Gave concise advice about directions and what to do" [](https://expedia.ca/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 "Clean room, quiet area, good breakfast" [](https://expedia.ca/Winchester-Hotels-Holiday-Inn-Winchester-Se-Historic-Gateway.h1889084.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 "Comfortable and clean room." [](https://expedia.ca/Winchester-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Winchester.h2678524.Hotel-Information) ![Comfort Inn Woodstock Shenandoah](https://images.trvl-media.com/lodging/1000000/330000/327400/327388/495de11d_y.jpg) ### Comfort Inn Woodstock Shenandoah 10/10 Excellent "Clean room great staff " [](https://expedia.ca/Luray-Hotels-Comfort-Inn-Woodstock-Shenandoah.h327388.Hotel-Information) ![Ramada by Wyndham Strasburg/Shenandoah Valley](https://images.trvl-media.com/lodging/2000000/1250000/1246400/1246311/08da8378_y.jpg) ### Ramada by Wyndham Strasburg/Shenandoah Valley 10/10 Excellent "All was well very, nice hotel! Breakfast was great. King size bed was nice, but the mattress was terrible, to soft and lympy, sheets and top cover seemed very worn. The bed wasn't too comfortable. We were in Room 201." [](https://expedia.ca/Winchester-Hotels-Ramada-By-Wyndham-Strasburg.h1246311.Hotel-Information) ![Country Inn & Suites by Radisson, Winchester, VA](https://images.trvl-media.com/lodging/2000000/1660000/1652900/1652833/d0690cde_y.jpg) ### Country Inn & Suites by Radisson, Winchester, VA 10/10 Excellent "Room was large, very clean and very comfortable." [](https://expedia.ca/Winchester-Hotels-Country-Inn-Suites-By-Radisson.h1652833.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 clean, heater works great parking " [](https://expedia.ca/Winchester-Hotels-Travelodge-By-Wyndham-Winchester.h9600.Hotel-Information) ## Find out more about Middletown ## Middletown Apartments information | Number of reviews | 86 | | ----------------- | ------------- | | Accommodation | 58 Apartments | | Lowest Price | CA $197 | | Highest Price | CA $545 | ## 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 - 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