Title: Middletown, VA Condos for Rent | 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) ![](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 [Apr 10 - Apr 12](https://www.expedia.com/Hotel-Search?regionId=12013&startDate=2026-04-10&endDate=2026-04-12&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two 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 three 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) In four months [Jul 17 - Jul 19](https://www.expedia.com/Hotel-Search?regionId=12013&startDate=2026-07-17&endDate=2026-07-19&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) No exact matches found, but these alternatives could be just right ## Recommended hotels in Middletown ![Dining](https://images.trvl-media.com/lodging/1000000/40000/34500/34467/a3d72fc4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/1000000/40000/34500/34467/2f175422.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior detail](https://images.trvl-media.com/lodging/1000000/40000/34500/34467/d6942b45.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Point of interest](https://images.trvl-media.com/lodging/1000000/40000/34500/34467/9e80fe83.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Wayside Inn [](https://www.expedia.com/Middletown-Hotels-Wayside-Inn.h34467.Hotel-Information) Middletown 9.2/10 Wonderful (426 reviews) "Old building but clean and very comfortable. Perfect spot and price." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Caroline $89 nightly $98 total Mar 29 - Mar 30 Total with taxes and fees [](https://www.expedia.com/Middletown-Hotels-Wayside-Inn.h34467.Hotel-Information) ![Breakfast area](https://images.trvl-media.com/lodging/1000000/860000/856400/856310/8753a03f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/860000/856400/856310/1c983a28.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Laundry room](https://images.trvl-media.com/lodging/1000000/860000/856400/856310/92453303.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 1 King Bed with Sofa bed, Non Smoking | Iron/ironing board, free cribs/infant beds, rollaway beds, free WiFi](https://images.trvl-media.com/lodging/1000000/860000/856400/856310/92ea6a73.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Econo Lodge Inn & Suites Middletown - Winchester South [](https://www.expedia.com/Middletown-Hotels-Econo-Lodge-Inn-Suites.h856310.Hotel-Information) Middletown 5.8/10 (303 reviews) "A bit pricey for the quality " ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) Louis $62 nightly $68 total Apr 5 - Apr 6 Total with taxes and fees [](https://www.expedia.com/Middletown-Hotels-Econo-Lodge-Inn-Suites.h856310.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/1000000/860000/855600/855557/10b5cc1e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/860000/855600/855557/d565eb6d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/860000/855600/855557/a71565c0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily on-the-go breakfast](https://images.trvl-media.com/lodging/1000000/860000/855600/855557/4749606b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Super 8 by Wyndham Front Royal Near Shenandoah National Park [](https://www.expedia.com/Front-Royal-Hotels-Super-8-By-Wyndham-Front-Royal.h855557.Hotel-Information) Front Royal 7.6/10 Good (1,000 reviews) "The national park was close by. That’s why we chose this location. That’s the only positive thing I can say. The rooms weren’t clean. The bathroom was disgusting. I stay in a lot of places to simply shower and sleep, but I wouldn’t stay here again. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Alayna $61 nightly $68 total Mar 29 - Mar 30 Total with taxes and fees [](https://www.expedia.com/Front-Royal-Hotels-Super-8-By-Wyndham-Front-Royal.h855557.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/58000000/57960000/57958300/57958244/cf4c2663.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily self-serve breakfast](https://images.trvl-media.com/lodging/58000000/57960000/57958300/57958244/c6c8c1e5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 2 Queen Beds, Non Smoking | Desk, blackout drapes, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/58000000/57960000/57958300/57958244/557f4fea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Desk, blackout drapes, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/58000000/57960000/57958300/57958244/8506bf92.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Comfort Inn & Suites Winchester [](https://www.expedia.com/Winchester-Hotels-Comfort-Inn-Suites.h57958244.Hotel-Information) Winchester 9.4/10 Exceptional (1,091 reviews) "Great location; easy access off hwy. Very nice staff; clean room; comfortable beds and nice breakfast!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Theresa $103 nightly $112 total Apr 21 - Apr 22 Total with taxes and fees [](https://www.expedia.com/Winchester-Hotels-Comfort-Inn-Suites.h57958244.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/2000000/1250000/1246400/1246311/220661a2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/2000000/1250000/1246400/1246311/69b7649a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1250000/1246400/1246311/2e837b11.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 2 Queen Beds, Non Smoking | Desk, laptop workspace, blackout drapes, iron/ironing board](https://images.trvl-media.com/lodging/2000000/1250000/1246400/1246311/4bbed885.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Ramada by Wyndham Strasburg/Shenandoah Valley [](https://www.expedia.com/Winchester-Hotels-Ramada-By-Wyndham-Strasburg.h1246311.Hotel-Information) Strasburg 8.4/10 Very Good (1,001 reviews) "Nice room and good location for an overnight stay." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Edward $81 nightly $90 total Apr 12 - Apr 13 Total with taxes and fees [](https://www.expedia.com/Winchester-Hotels-Ramada-By-Wyndham-Strasburg.h1246311.Hotel-Information) ![Restaurant](https://images.trvl-media.com/lodging/1000000/430000/424900/424883/2fa2dbbe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/430000/424900/424883/1d5ecc9d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily buffet breakfast](https://images.trvl-media.com/lodging/1000000/430000/424900/424883/0ec10473.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Studio, 1 King Bed, Non Smoking, Refrigerator & Microwave (Wet bar) | Premium bedding, pillowtop beds, in-room safe, individually furnished](https://images.trvl-media.com/lodging/1000000/430000/424900/424883/5daa33ff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn Winchester N/Conference Center, VA [](https://www.expedia.com/Winchester-Hotels-Hampton-Inn-Winchester-NConference-Center.h424883.Hotel-Information) Winchester 9.2/10 Wonderful (870 reviews) "The staff was wonderful! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jayne $106 nightly $120 total Apr 18 - Apr 19 Total with taxes and fees [](https://www.expedia.com/Winchester-Hotels-Hampton-Inn-Winchester-NConference-Center.h424883.Hotel-Information) ![Standard Double Room, 2 Double Beds, Non Smoking | Blackout drapes, iron/ironing board, free cribs/infant beds](https://images.trvl-media.com/lodging/1000000/180000/172900/172810/cab65b9d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/180000/172900/172810/0fd2f943.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily continental breakfast](https://images.trvl-media.com/lodging/1000000/180000/172900/172810/9e37f17d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/1000000/180000/172900/172810/c5cff2bc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Quality Inn Winchester [](https://www.expedia.com/Winchester-Hotels-Quality-Inn.h172810.Hotel-Information) Winchester 9.2/10 Wonderful (1,000 reviews) "Everything was perfect. Would highly recommend this hotel" ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) Phyllis $88 nightly $96 total Apr 15 - Apr 16 Total with taxes and fees [](https://www.expedia.com/Winchester-Hotels-Quality-Inn.h172810.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/2000000/1070000/1066500/1066410/0de00556.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/2000000/1070000/1066500/1066410/f063e2e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/2000000/1070000/1066500/1066410/b20fa3f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1070000/1066500/1066410/08af73b4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Fairfield Inn & Suites by Marriott Winchester [](https://www.expedia.com/Winchester-Hotels-Fairfield-Inn-Suites-By-Marriott-Winchester.h1066410.Hotel-Information) Winchester 9.0/10 Wonderful (829 reviews) "We stay here a lot and it is always consistently clean and service is great. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kim $93 nightly $101 total Mar 31 - Apr 1 Total with taxes and fees [](https://www.expedia.com/Winchester-Hotels-Fairfield-Inn-Suites-By-Marriott-Winchester.h1066410.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/2000000/1660000/1652900/1652833/a391dd61.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/2000000/1660000/1652900/1652833/b42e7086.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Desk, laptop workspace, blackout drapes, iron/ironing board](https://images.trvl-media.com/lodging/2000000/1660000/1652900/1652833/f49e1754.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1660000/1652900/1652833/39b30783.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Country Inn & Suites by Radisson, Winchester, VA [](https://www.expedia.com/Winchester-Hotels-Country-Inn-Suites-By-Radisson.h1652833.Hotel-Information) Winchester 8.8/10 Excellent (1,000 reviews) "Very clean rooms and friendly staff." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Christine $91 nightly $99 total Apr 19 - Apr 20 Total with taxes and fees [](https://www.expedia.com/Winchester-Hotels-Country-Inn-Suites-By-Radisson.h1652833.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/1000000/330000/327400/327388/495de11d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/330000/327400/327388/f93b311c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/330000/327400/327388/6fc2cc72.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 King Bed, Accessible, Non Smoking | Desk, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/1000000/330000/327400/327388/be978095.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Comfort Inn Woodstock Shenandoah [](https://www.expedia.com/Luray-Hotels-Comfort-Inn-Woodstock-Shenandoah.h327388.Hotel-Information) Woodstock 8.8/10 Excellent (1,000 reviews) "Hotel is very convenient and comfortable." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Dianna $95 nightly $106 total Apr 5 - Apr 6 Total with taxes and fees [](https://www.expedia.com/Luray-Hotels-Comfort-Inn-Woodstock-Shenandoah.h327388.Hotel-Information) ![Reception](https://images.trvl-media.com/lodging/125000000/124030000/124020600/124020522/985bcde3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/125000000/124030000/124020600/124020522/fbba5f70.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Home2 Suites By Hilton Winchester [](https://www.expedia.com/Winchester-Hotels-Home2-Suites-By-Hilton-Winchester.h124020522.Hotel-Information) Winchester $98 nightly $111 total Apr 5 - Apr 6 Total with taxes and fees [](https://www.expedia.com/Winchester-Hotels-Home2-Suites-By-Hilton-Winchester.h124020522.Hotel-Information) ![Porch](https://images.trvl-media.com/lodging/12000000/11860000/11854200/11854156/a99c9843.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property - evening/night](https://images.trvl-media.com/lodging/12000000/11860000/11854200/11854156/bdaadecc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Garden](https://images.trvl-media.com/lodging/12000000/11860000/11854200/11854156/24e47a16.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Combined shower/tub, hair dryer, towels](https://images.trvl-media.com/lodging/12000000/11860000/11854200/11854156/4c832c6a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Relax Inn Motel [](https://www.expedia.com/Winchester-Hotels-Relax-Inn-Motel.h11854156.Hotel-Information) Front Royal 8.2/10 Very Good (261 reviews) "Nice place for the price, in this town it's pretty much the best place to stay if you don't want to pay 150+ " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) James $67 nightly $75 total Apr 1 - Apr 2 Total with taxes and fees [](https://www.expedia.com/Winchester-Hotels-Relax-Inn-Motel.h11854156.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/1000000/10000/9600/9600/19e0634f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 King Bed, Smoking | Living area | LED TV](https://images.trvl-media.com/lodging/1000000/10000/9600/9600/38eadba9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/10000/9600/9600/9d44a9b1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 King Bed, Smoking | Living area | LED TV](https://images.trvl-media.com/lodging/1000000/10000/9600/9600/bf0bfb1b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Travelodge by Wyndham Winchester [](https://www.expedia.com/Winchester-Hotels-Travelodge-By-Wyndham-Winchester.h9600.Hotel-Information) Winchester 8.6/10 Excellent (1,073 reviews) "Very clean and great rates will stay again if in the area " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Cindi $71 nightly $77 total Mar 29 - Mar 30 Total with taxes and fees [](https://www.expedia.com/Winchester-Hotels-Travelodge-By-Wyndham-Winchester.h9600.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/2000000/1890000/1889100/1889084/c68804b2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/2000000/1890000/1889100/1889084/d236d605.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/2000000/1890000/1889100/1889084/ee4df7fa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/2000000/1890000/1889100/1889084/7ff8d7be.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Winchester Se-Historic Gateway by IHG [](https://www.expedia.com/Winchester-Hotels-Holiday-Inn-Winchester-Se-Historic-Gateway.h1889084.Hotel-Information) Winchester 9.0/10 Wonderful (1,001 reviews) "very nice hotel,very clean" ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) Maria $91 nightly $99 total Apr 5 - Apr 6 Total with taxes and fees [](https://www.expedia.com/Winchester-Hotels-Holiday-Inn-Winchester-Se-Historic-Gateway.h1889084.Hotel-Information) ![Premium bedding, desk, soundproofing, iron/ironing board](https://images.trvl-media.com/lodging/2000000/1500000/1495000/1494994/4a9e2869.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/2000000/1500000/1495000/1494994/855c5fac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/2000000/1500000/1495000/1494994/cbf75a17.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 1 King Bed, Non Smoking | Premium bedding, desk, soundproofing, iron/ironing board](https://images.trvl-media.com/lodging/2000000/1500000/1495000/1494994/08e61bc5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Econo Lodge Woodstock - Shenandoah Valley I-81 [](https://www.expedia.com/Luray-Hotels-Econo-Lodge-Woodstock-Shenandoah-Valley-I-81.h1494994.Hotel-Information) Woodstock 7.2/10 Good (644 reviews) "Very nice clean room for the age of the property. Found it quiet and comfortable. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Michael $51 nightly $57 total Apr 12 - Apr 13 Total with taxes and fees [](https://www.expedia.com/Luray-Hotels-Econo-Lodge-Woodstock-Shenandoah-Valley-I-81.h1494994.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/1000000/120000/117800/117743/ac575b89.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/120000/117800/117743/4baca37a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/1000000/120000/117800/117743/cd7ad69b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 Bedroom | Living area | 48-inch flat-screen TV with cable channels, TV](https://images.trvl-media.com/lodging/1000000/120000/117800/117743/5df91a0d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Spark by Hilton Winchester [](https://www.expedia.com/Winchester-Hotels-Spark-By-Hilton-Winchester.h117743.Hotel-Information) Winchester 9.0/10 Wonderful (1,001 reviews) "Nice staff, clean with a convenient location make it a good choice for a stay in Winchester. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Mira $89 nightly $100 total Apr 5 - Apr 6 Total with taxes and fees [](https://www.expedia.com/Winchester-Hotels-Spark-By-Hilton-Winchester.h117743.Hotel-Information) ![Winery](https://images.trvl-media.com/lodging/1000000/20000/10600/10535/79eb6aef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Winery](https://images.trvl-media.com/lodging/1000000/20000/10600/10535/03d5d9db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/1000000/20000/10600/10535/25f6542c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Room, 1 King Bed, Non Smoking, Hot Tub | In-room safe, desk, laptop workspace, blackout drapes](https://images.trvl-media.com/lodging/1000000/20000/10600/10535/48177602.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Baymont by Wyndham Front Royal Near Shenandoah National Park [](https://www.expedia.com/Winchester-Hotels-Baymont-By-Wyndham-Front-Royal-Near-Shenandoah-National-Park.h10535.Hotel-Information) Front Royal 6.4/10 (934 reviews) "Great location, price, and people! Would definitely stay here again." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Amelia $58 nightly $64 total Mar 30 - Mar 31 Total with taxes and fees [](https://www.expedia.com/Winchester-Hotels-Baymont-By-Wyndham-Front-Royal-Near-Shenandoah-National-Park.h10535.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/40000/34400/34394/83ee60b6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Individually furnished, desk, laptop workspace, blackout drapes](https://images.trvl-media.com/lodging/1000000/40000/34400/34394/fde0973a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/40000/34400/34394/ab6f1ae4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free buffet breakfast](https://images.trvl-media.com/lodging/1000000/40000/34400/34394/ef7d5b18.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Express Winchester South-Stephens City by IHG [](https://www.expedia.com/Winchester-Hotels-Holiday-Inn-Express-Winchester-South-Stephens-City.h34394.Hotel-Information) Stephens City 8.2/10 Very Good (841 reviews) "Yes. Parking was great" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) John $91 nightly $99 total Apr 4 - Apr 5 Total with taxes and fees [](https://www.expedia.com/Winchester-Hotels-Holiday-Inn-Express-Winchester-South-Stephens-City.h34394.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/2000000/1500000/1497900/1497898/1b2ad59b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/2000000/1500000/1497900/1497898/5ea79918.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1500000/1497900/1497898/723a3b2f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/2000000/1500000/1497900/1497898/8f242b36.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Courtyard by Marriott Winchester [](https://www.expedia.com/Winchester-Hotels-Courtyard-By-Marriott-Winchester.h1497898.Hotel-Information) Winchester 9.0/10 Wonderful (948 reviews) "Great location" ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) jim $107 nightly $116 total Apr 3 - Apr 4 Total with taxes and fees [](https://www.expedia.com/Winchester-Hotels-Courtyard-By-Marriott-Winchester.h1497898.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/900000/892600/892585/w3840h2556x0y4-810f7f7f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![50-inch LCD TV with cable channels, TV](https://images.trvl-media.com/lodging/1000000/900000/892600/892585/6c4fd659.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/900000/892600/892585/w3840h2556x0y4-a519cf5a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/900000/892600/892585/40efde4b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn Front Royal [](https://www.expedia.com/Winchester-Hotels-Hampton-Inn-Front-Royal.h892585.Hotel-Information) Front Royal 9.0/10 Wonderful (1,000 reviews) "All the staff members were so nice and kind!! The hotel room I booked were very clean and spotless, and the breakfast was even fresh too!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kenny $102 nightly $113 total Apr 12 - Apr 13 Total with taxes and fees [](https://www.expedia.com/Winchester-Hotels-Hampton-Inn-Front-Royal.h892585.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=2026-04-11&endDate=2026-04-12®ionId=12013&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true) ## 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=2026-06-26&d1=2026-06-26&endDate=2026-06-29&d2=2026-06-29&lodging=CABIN) 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=2026-06-26&d1=2026-06-26&endDate=2026-06-29&d2=2026-06-29&lodging=VACATION_HOME) 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=2026-06-26&d1=2026-06-26&endDate=2026-06-29&d2=2026-06-29&lodging=COTTAGE) 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=2026-06-26&d1=2026-06-26&endDate=2026-06-29&d2=2026-06-29&lodging=CHALET) 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=2026-06-26&d1=2026-06-26&endDate=2026-06-29&d2=2026-06-29&lodging=APARTMENT) 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=2026-06-26&d1=2026-06-26&endDate=2026-06-29&d2=2026-06-29&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-Condos.d12013-aaCondos.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.com/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FMiddletown-Condos.d12013-aaCondos.Travel-Guide-Accommodation) ## Top Middletown Hotel Reviews ![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, friendly staff, good location. Only cons were hallway carpet is rippled and no free breakfast" [](https://expedia.com/Winchester-Hotels-Holiday-Inn-Winchester-Se-Historic-Gateway.h1889084.Hotel-Information) ![Comfort Inn & Suites Winchester](https://images.trvl-media.com/lodging/58000000/57960000/57958300/57958244/cf4c2663_y.jpg) ### Comfort Inn & Suites Winchester 10/10 Excellent "Overall a pleasant stay!" [](https://expedia.com/Winchester-Hotels-Comfort-Inn-Suites.h57958244.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 6/10 Okay "Room was clean. Very basic room. Breakfast was adequate." [](https://expedia.com/Winchester-Hotels-Microtel-Inn-Suites-By-Wyndham-Winchester.h70921061.Hotel-Information) ![Sleep Inn & Suites Winchester near University](https://images.trvl-media.com/lodging/1000000/900000/892900/892882/554af346_y.jpg) ### Sleep Inn & Suites Winchester near University 6/10 Okay "I only stayed for about an hour. The room was freezing cold as it was dead of winter and freezing out. There was no heat turned on in the room when I got there so it was quite a while before the room actually reached a tolerable temperature" [](https://expedia.com/Winchester-Hotels-Sleep-Inn-Suites.h892882.Hotel-Information) ![La Quinta Inn & Suites by Wyndham Winchester](https://images.trvl-media.com/lodging/3000000/2680000/2678600/2678524/9e66afda_y.jpg) ### La Quinta Inn & Suites by Wyndham Winchester 10/10 Excellent "Very nice would stay there again" [](https://expedia.com/Winchester-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Winchester.h2678524.Hotel-Information) ![Travelodge by Wyndham Winchester](https://images.trvl-media.com/lodging/1000000/10000/9600/9600/19e0634f_y.jpg) ### Travelodge by Wyndham Winchester 10/10 Excellent "Clean and comfortable and safe!" [](https://expedia.com/Winchester-Hotels-Travelodge-By-Wyndham-Winchester.h9600.Hotel-Information) ![Hampton Inn Front Royal](https://images.trvl-media.com/lodging/1000000/900000/892600/892585/810f7f7f_y.jpg) ### Hampton Inn Front Royal 10/10 Excellent "Everything was amazing! We actually left another hotel because it was dirty and didn’t feel safe. We found this place randomly during our drive and couldn’t have been happier. The room was spotless, the staff was friendly, and we had a great night’s sleep." [](https://expedia.com/Winchester-Hotels-Hampton-Inn-Front-Royal.h892585.Hotel-Information) ![Fairfield Inn & Suites by Marriott Winchester](https://images.trvl-media.com/lodging/2000000/1070000/1066500/1066410/0de00556_y.jpg) ### Fairfield Inn & Suites by Marriott Winchester 10/10 Excellent "Right off 81 with several restaurants nearby. Spacious rooms" [](https://expedia.com/Winchester-Hotels-Fairfield-Inn-Suites-By-Marriott-Winchester.h1066410.Hotel-Information) ![DoubleTree by Hilton Front Royal Blue Ridge Shadows](https://images.trvl-media.com/lodging/2000000/1890000/1889100/1889081/204cbf3a_y.jpg) ### DoubleTree by Hilton Front Royal Blue Ridge Shadows 10/10 Excellent "Business friendly. Computers in lobby, conference rooms and golf ⛳️ within driving distance of oldtown winchester and senandoah national park including skyline drive." [](https://expedia.com/Front-Royal-Hotels-Holiday-Inn-Suites-Front-Royal-Blue-Ridge-Shadows.h1889081.Hotel-Information) ## Find out more about Middletown ## Middletown Condo Rentals information | Number of reviews | 15,318 | | ----------------- | --------------- | | Accommodation | 2 Condo Rentals | | Lowest Price | $64 | | Highest Price | $120 | ## 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) - [Hotels near Cedar Creek Battlefield Foundation ](https://www.expedia.com/Cedar-Creek-Battlefield-Foundation-Hotels.0-l553248621532661823-0.Travel-Guide-Filter-Hotels) - [Hotels near Belle Grove Plantation ](https://www.expedia.com/Belle-Grove-Plantation-Hotels.0-l6164020-0.Travel-Guide-Filter-Hotels) - 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