Title: Holiday Rentals Winchester from £95: Find Short-Term Rentals & Holiday Accommodations | Expedia.co.uk [Hotels in Winchester](https://expedia.co.uk/Winchester-Hotels.d6056879.Travel-Guide-Hotels)[Flights to Winchester](https://expedia.co.uk/Cheap-Flights-To-Winchester.d6056879.Travel-Guide-Flights)[Winchester Car Hire](https://expedia.co.uk/Compare-Cheap-Car-Hire-In-Winchester.d6056879.Car-Hire-Guide)[Winchester Holidays](https://expedia.co.uk/Winchester.d6056879.Holidays-City-Breaks) ![](https://mediaim.expedia.com/destination/1/720fb116634761161ecda43d4ca150e7.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Search Holiday Rentals in Winchester ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__price_find.svg) ### Change your mind Book hotels with free cancellation ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Save instantly and earn perks with One Key [Learn about One Key](https://www.expedia.co.uk/welcome-one-key) ![](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 [24 Oct - 26 Oct](https://www.expedia.co.uk/Hotel-Search?regionId=6056879&startDate=2025-10-24&endDate=2025-10-26&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [5 Dec - 7 Dec](https://www.expedia.co.uk/Hotel-Search?regionId=6056879&startDate=2025-12-05&endDate=2025-12-07&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [2 Jan - 4 Jan](https://www.expedia.co.uk/Hotel-Search?regionId=6056879&startDate=2026-01-02&endDate=2026-01-04&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [30 Jan - 1 Feb](https://www.expedia.co.uk/Hotel-Search?regionId=6056879&startDate=2026-01-30&endDate=2026-02-01&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Holiday Rentals in Winchester ![Outdoor dining](https://images.trvl-media.com/lodging/73000000/72940000/72936100/72936072/9fcb6e62.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, books](https://images.trvl-media.com/lodging/73000000/72940000/72936100/72936072/22634c2e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/73000000/72940000/72936100/72936072/921193d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/73000000/72940000/72936100/72936072/cfaa6bcd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Dreamtime - Modern A-frame Cabin w/ Hot tub Berkeley Springs 10/10 Exceptional (47) "Awesome place! Perfect for 4 people. Great long weekend!" [](https://www.expedia.co.uk/Berkeley-Springs-Hotels-Dreamtime-Modern-A-Frame-Cabin-W-Hot-Tub.h72936072.Hotel-Information) ![Garden](https://images.trvl-media.com/lodging/24000000/23010000/23004100/23004100/22255107.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/24000000/23010000/23004100/23004100/5a919945.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Quadruple Room, Ensuite | Interior](https://images.trvl-media.com/lodging/24000000/23010000/23004100/23004100/f229dd73.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/24000000/23010000/23004100/23004100/e82f2a35.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Road Haven 1830 Mount Jackson 9.6/10 Exceptional (36) "Great place to stay! It’s clean cozy and quiet! I would definitely stay again in the future!" £108 includes taxes & fees 13 Oct - 14 Oct [](https://www.expedia.co.uk/Luray-Hotels-Family-Farmhouse-Inn.h23004100.Hotel-Information) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/106000000/105320000/105319100/105319025/f6c9e6df.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/106000000/105320000/105319100/105319025/bb644d7d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/106000000/105320000/105319100/105319025/4867d85d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/106000000/105320000/105319100/105319025/b50d6997.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Private, light filled retreat space... with your own pickleball court! Berkeley Springs 10/10 Exceptional (51) "Couldn't ask for a nicer place to stay peaceful, quiet with a great view. Wildlife is abundant and beautiful everything that you could need or want to relax Bill and Patty were excellent hosts looking forward to visiting again" [](https://www.expedia.co.uk/Berkeley-Springs-Hotels-Private.h105319025.Hotel-Information) ![Cabin, 1 Queen Bed, Mountain View | 1 bedroom, pillow-top beds, free WiFi, bed sheets](https://images.trvl-media.com/lodging/113000000/112100000/112098800/112098770/63dbb872.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Cabin, 1 Queen Bed, Non Smoking, Mountain View | 1 bedroom, pillow-top beds, free WiFi, bed sheets](https://images.trvl-media.com/lodging/113000000/112100000/112098800/112098770/08eb3fe6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/113000000/112100000/112098800/112098770/4b8eadd6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Mobile Home, 1 Queen Bed, Non Smoking, Mountain View | 1 bedroom, pillow-top beds, free WiFi, bed sheets](https://images.trvl-media.com/lodging/113000000/112100000/112098800/112098770/64262b4b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Canal Cabins Paw Paw 9.6/10 Exceptional (10) "Very nice " £95 includes taxes & fees 12 Oct - 13 Oct [](https://www.expedia.co.uk/Paw-Paw-Hotels-Canal-Cabins.h112098770.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/28000000/27140000/27132300/27132250/9545f24c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Children’s area](https://images.trvl-media.com/lodging/28000000/27140000/27132300/27132250/c7101f86.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/28000000/27140000/27132300/27132250/41d8d16c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/28000000/27140000/27132300/27132250/2d866371.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Private getaway w/ hot tub, wifi. Secluded amongst trees & near Sleepy Creek. Berkeley Springs 9.8/10 Exceptional (286) "Very nice stay. We used the fire pit and hot tub and enjoyed both. Excellent location close to cacapon, we ended up hiking and doing the clay shooting. The cabin itself was very nice, cozy, and clean. " £278 includes taxes & fees 14 Oct - 15 Oct [](https://www.expedia.co.uk/Berkeley-Springs-Hotels-Private-Getaway-W-Hot-Tub.h27132250.Hotel-Information) ![Outdoor spa tub](https://images.trvl-media.com/lodging/23000000/22250000/22243700/22243657/edab5469.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, stereo](https://images.trvl-media.com/lodging/23000000/22250000/22243700/22243657/f7fc0dd2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, stereo](https://images.trvl-media.com/lodging/23000000/22250000/22243700/22243657/e4de5c70.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/23000000/22250000/22243700/22243657/b116227a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### "Walden" Modern Cabin on 54 Riverfront Acres along Shenandoah River w/Hot Tub Rileyville 10/10 Exceptional (341) "We had a great time and can't wait to return" £243 includes taxes & fees 5 Nov - 6 Nov [](https://www.expedia.co.uk/Rileyville-Hotels-Walden-Spectacular-Riverfront-Cabin-On-54-Acres-Whot-Tub-Near-Luray.h22243657.Hotel-Information) ![Pool](https://images.trvl-media.com/lodging/23000000/22260000/22255700/22255620/f116a78a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/23000000/22260000/22255700/22255620/238eed9f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, stereo](https://images.trvl-media.com/lodging/23000000/22260000/22255700/22255620/2dc032bc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/23000000/22260000/22255700/22255620/08441d4f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### "Solitude" Secluded 1 BR Cabin Nestled in the Woods w/ Hot Tub near Luray, VA. Rileyville 10/10 Exceptional (332) "Place was beautiful and lived up to the name Solitude. Spent our honeymoon in perfect bliss. Great location to get away. " £243 includes taxes & fees 4 Nov - 5 Nov [](https://www.expedia.co.uk/Rileyville-Hotels-Solitude-Spectacular-1-BR-Cabin-W-Hot-Tub-Near-Luray.h22255620.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/31000000/30790000/30788500/30788475/2cb5e40f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, books, stereo](https://images.trvl-media.com/lodging/31000000/30790000/30788500/30788475/b8faf3e2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/31000000/30790000/30788500/30788475/fb065307.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/31000000/30790000/30788500/30788475/7a01ed03.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Star view cabin-Riverfront Rileyville 9.8/10 Exceptional (331) "We had a wonderful time! The property has a great view and the host was very friendly and accommodating. " [](https://www.expedia.co.uk/Rileyville-Hotels-Star-View-Cabin-Riverfront.h30788475.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) ![Interior](https://images.trvl-media.com/lodging/96000000/95130000/95120300/95120287/cf55968e.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) ### Cute Riverside Cabin w Hot Tub, Fire Pit, & Kayaks Luray 10/10 Exceptional (13) "It was an amazing place, will recommend to friends and hopefully will be back." £210 includes taxes & fees 4 Nov - 5 Nov [](https://www.expedia.co.uk/Rileyville-Hotels-Cute-Riverside-Cabin-W-Hot-Tub.h95120287.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/31000000/30750000/30748600/30748551/9d5bcd01.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor spa tub](https://images.trvl-media.com/lodging/31000000/30750000/30748600/30748551/7ed98fea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/31000000/30750000/30748600/30748551/cf2e8ea1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/31000000/30750000/30748600/30748551/w800h599x0y1-bc122210.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Charming 1800s Farmhouse on 47 Acres — Riverfront w/Views, Hot Tub, Pet-Friendly Rileyville 9.6/10 Exceptional (200) "Amazing as always. Love this area. " [](https://www.expedia.co.uk/Rileyville-Hotels-Riverfront-Farmhouse-With-Mountain-Views.h30748551.Hotel-Information) ![Smart TV, fireplace, DVD player, video library](https://images.trvl-media.com/lodging/74000000/73280000/73278500/73278478/16bb3523.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/74000000/73280000/73278500/73278478/24fb52ad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/74000000/73280000/73278500/73278478/w1692h1125x372y0-9436cdc5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/74000000/73280000/73278500/73278478/b52ed37f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Bear Timbers log cabin on the Shenandoah River Rileyville 9.8/10 Exceptional (67) "We had a fantastic time! All messages were promptly answered and the property was clean and as advertised!" [](https://www.expedia.co.uk/Rileyville-Hotels-Bear-Timbers-Log-Cabin-On-The-Shenandoah-River.h73278478.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/94000000/93520000/93510500/93510450/e5d7776a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/94000000/93520000/93510500/93510450/5ce5fa13.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, offices](https://images.trvl-media.com/lodging/94000000/93520000/93510500/93510450/2b9acd11.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, desk, free WiFi, bed sheets](https://images.trvl-media.com/lodging/94000000/93520000/93510500/93510450/bc6898f5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 18th Century Stone Cottage minutes from historic Middleburg Middleburg 10/10 Exceptional (47) "What a peaceful place and wonderful views." £304 includes taxes & fees 26 Oct - 27 Oct [](https://www.expedia.co.uk/Middleburg-Hotels-18th-Century-Stone-Cottage-Minutes-From-Historic-Middleburg.h93510450.Hotel-Information) ![Dining](https://images.trvl-media.com/lodging/88000000/87810000/87800600/87800580/w1120h749x6y3-7738ec31.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/88000000/87810000/87800600/87800580/ae64454b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/88000000/87810000/87800600/87800580/70f73403.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/88000000/87810000/87800600/87800580/e896adbe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy Mountain Cabin w/ Steam Shower! Family Friendly. Harpers Ferry 10/10 Exceptional (75) "Wonderful view from the sunroom. Peaceful and rejuvenating stay in this welcoming home. " £214 includes taxes & fees 14 Oct - 15 Oct [](https://www.expedia.co.uk/Harpers-Ferry-Hotels-Cozy-Getaway-With-Steam-Shower-Perfect-For-Couples-And-Families.h87800580.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/34000000/33750000/33748300/33748224/e001c092.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/34000000/33750000/33748300/33748224/1bc4382f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor spa tub](https://images.trvl-media.com/lodging/34000000/33750000/33748300/33748224/ef37595a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/34000000/33750000/33748300/33748224/ee30ee65.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Falling Leaf Cabin - Rustic Charm With Modern Decor! Rileyville 9.8/10 Exceptional (300) "Cute cozy cabin in a great location. Was perfect for stopping in Luray, taking hiking trips to Shenandoah National Park, or just staying in. Had a wonderful time! Would definitely recommend to anyone looking for a cabin in the area." [](https://www.expedia.co.uk/Rileyville-Hotels-Falling-Leaf-Cabin-Secluded-With-Mountain-View.h33748224.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/38000000/37270000/37267100/37267085/7b4d8e16.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, ping pong, stereo](https://images.trvl-media.com/lodging/38000000/37270000/37267100/37267085/a2e5a0c4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/38000000/37270000/37267100/37267085/bef3749f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, free WiFi, bed sheets](https://images.trvl-media.com/lodging/38000000/37270000/37267100/37267085/32925bf2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hidden Gem in the woods with hot tub Berkeley Springs 9.6/10 Exceptional (82) "Outstanding property was just what the doctor ordered for a rejuvenating time of R&R. Clean and comfortable, all of the amenities—including the hot tub— made for a lovely stay. " [](https://www.expedia.co.uk/Berkeley-Springs-Hotels-Hidden-Gem-In-The-Woods-With-Hot-Tub.h37267085.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/101000000/100820000/100818300/100818202/3d2436ee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/101000000/100820000/100818300/100818202/dea97a57.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/101000000/100820000/100818300/100818202/4e07b9b2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/101000000/100820000/100818300/100818202/eb4d742e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Rustic Tabor Woods Cabin near Cacapon State Park w/Patio, Grill Berkeley Springs 9.0/10 Wonderful (12) "Hot tub was nice relaxing cozy cabin" £161 includes taxes & fees 13 Oct - 14 Oct [](https://www.expedia.co.uk/Berkeley-Springs-Hotels-Rustic-Tabor-Woods-Cabin-Near-Cacapon-State-Park-WPatio.h100818202.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/84000000/83550000/83542600/83542571/48307a2c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/84000000/83550000/83542600/83542571/7ed36a8e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/84000000/83550000/83542600/83542571/159749b9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/84000000/83550000/83542600/83542571/fb69b272.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Dog Friendly Cabin near River on Nearly 5 acres w/Strong WiFi + Robust Amenities Luray 9.6/10 Exceptional (63) "We had a great stay! The place was very clean, the back deck was such a great added bonus.. had a good selection of movies and games. 4 wheel drive is advisable. Very comfy!!" £249 includes taxes & fees 15 Oct - 16 Oct [](https://www.expedia.co.uk/Luray-Hotels-Dog-Friendly-Shenandoah-Views-WiFi.h83542571.Hotel-Information) ![Dining](https://images.trvl-media.com/lodging/23000000/22780000/22775200/22775112/034f0b68.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/23000000/22780000/22775200/22775112/9a350c2b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/23000000/22780000/22775200/22775112/a44c1480.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor spa tub](https://images.trvl-media.com/lodging/23000000/22780000/22775200/22775112/014b8e74.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Spectacular Views, Swimming Pool, Hot Tub, Real Log Fires, Mountain Getaway Rileyville 9.4/10 Exceptional (145) "We had a wonderful and relaxing time at Mountain Moonshine Retreat. The house was clean, the view was spectacular, and the pool was a bonus. We hope to stay there again in the future." [](https://www.expedia.co.uk/Rileyville-Hotels-Spectacular-Views.h22775112.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/31000000/30100000/30098000/30097949/3c8ac31f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms](https://images.trvl-media.com/lodging/31000000/30100000/30098000/30097949/05ab1142.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/31000000/30100000/30098000/30097949/82267afb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/31000000/30100000/30098000/30097949/d177b5cc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Bear Valley- Riverfront with hot tub - Starlink Satellite Wi-Fi Luray 9.4/10 Exceptional (128) "We enjoyed our quick little getaway." [](https://www.expedia.co.uk/Luray-Hotels-Bear-Valley-Riverfront-With-Hot-Tub.h30097949.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/61000000/60280000/60275500/60275436/28843540.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/61000000/60280000/60275500/60275436/60677176.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace, offices](https://images.trvl-media.com/lodging/61000000/60280000/60275500/60275436/2467c911.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/61000000/60280000/60275500/60275436/2ffeed83.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hot Tub, Large Deck, WiFi, Fire Pit at Chalet Cabin Berkeley Springs 9.2/10 Wonderful (33) "Excellent property for a quiet and relaxing long weekend. The wood stove and hot tub made the chilly evenings warm and romantic! Highly recommend this property!" £262 includes taxes & fees 5 Nov - 6 Nov [](https://www.expedia.co.uk/Berkeley-Springs-Hotels-Hot-Tub.h60275436.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.co.uk/Hotel-Search?startDate=2025-10-25&endDate=2025-10-26®ionId=6056879&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.co.uk/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FWinchester-Holiday-Rentals.d6056879.Travel-Guide-HolidayRentals)[Sign up, it's free](https://expedia.co.uk/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FWinchester-Holiday-Rentals.d6056879.Travel-Guide-HolidayRentals) ## Top Winchester Hotel Reviews ![Days Inn by Wyndham Winchester](//images.trvl-media.com/lodging/1000000/20000/19700/19613/dabc5e45_y.jpg) ### Days Inn by Wyndham Winchester 10/10 Excellent "The comfort of the bed was exceptional. The only thing that was difficult was the shower had no seat and I am unable to stand and very low toilet. " [](https://expedia.co.uk/Winchester-Hotels-Days-Inn-By-Wyndham-Winchester.h19613.Hotel-Information) ![Country Inn & Suites by Radisson, Winchester, VA](//images.trvl-media.com/lodging/2000000/1660000/1652900/1652833/d0690cde_y.jpg) ### Country Inn & Suites by Radisson, Winchester, VA 10/10 Excellent "Great stay. Pleasant staff. Price was good. Quick, easy check in. Room clean and pet free (as requested). Breakfast was biscuits and gravy, waffles, danishes but no eggs. Would stay again if in area. " [](https://expedia.co.uk/Winchester-Hotels-Country-Inn-Suites-By-Radisson.h1652833.Hotel-Information) ![The George Washington Hotel, A Wyndham Grand Hotel](//images.trvl-media.com/lodging/2000000/1370000/1364100/1364026/5a07226c_y.jpg) ### The George Washington Hotel, A Wyndham Grand Hotel 10/10 Excellent "2 blocks from city hall/old town. Got married at city hall. Very easy and accessible and the hotel was beautiful. " [](https://expedia.co.uk/Winchester-Hotels-The-George-Washington-Hotel.h1364026.Hotel-Information) ![SpringHill Suites by Marriott Winchester](//images.trvl-media.com/lodging/43000000/42550000/42543800/42543772/193cda05_y.jpg) ### SpringHill Suites by Marriott Winchester 10/10 Excellent "Convenient " [](https://expedia.co.uk/Winchester-Hotels-SpringHill-Suites-By-Marriott-Winchester.h42543772.Hotel-Information) ![La Quinta Inn & Suites by Wyndham Winchester](//images.trvl-media.com/lodging/3000000/2680000/2678600/2678524/3336c7bb_y.jpg) ### La Quinta Inn & Suites by Wyndham Winchester 10/10 Excellent "Great location." [](https://expedia.co.uk/Winchester-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Winchester.h2678524.Hotel-Information) ![Microtel Inn & Suites by Wyndham Winchester](//images.trvl-media.com/lodging/71000000/70930000/70921100/70921061/fab1f657_y.jpg) ### Microtel Inn & Suites by Wyndham Winchester 10/10 Excellent "Clean place good price" [](https://expedia.co.uk/Winchester-Hotels-Microtel-Inn-Suites-By-Wyndham-Winchester.h70921061.Hotel-Information) ![Motel 6 Winchester, VA](//images.trvl-media.com/lodging/1000000/50000/43100/43087/f87cf676_y.jpg) ### Motel 6 Winchester, VA 10/10 Excellent "Always da best motel an experience " [](https://expedia.co.uk/Winchester-Hotels-Motel-6-Winchester.h43087.Hotel-Information) ![Travelodge by Wyndham Winchester](//images.trvl-media.com/lodging/1000000/10000/9600/9600/28616e5b_y.jpg) ### Travelodge by Wyndham Winchester 10/10 Excellent "Air conditioner works fine comfy bed! I have stayed here several times. Breakfast is not awesome but decent!! Coffee is awesome! :) I will stay here again" [](https://expedia.co.uk/Winchester-Hotels-Travelodge-By-Wyndham-Winchester.h9600.Hotel-Information) ![Sleep Inn & Suites Winchester near University](//images.trvl-media.com/lodging/1000000/900000/892900/892882/53b7b275_y.jpg) ### Sleep Inn & Suites Winchester near University 10/10 Excellent "Good" [](https://expedia.co.uk/Winchester-Hotels-Sleep-Inn-Suites.h892882.Hotel-Information) ## Find out more about Winchester **Everything you need to know about** **Winchester** **holiday rentals** Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Winchester holiday rental for you. At Expedia, you can take your pick from private holiday homes, [apartments](https://www.expedia.co.uk/aa/Apartments), cottages, [apart-hotels](https://www.expedia.co.uk/aa/ApartHotels), cabins, [villas](https://www.expedia.co.uk/aa/Villas)... The list goes on, and on… and on! There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Winchester holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.  **Winchester holiday rentals: An excellent choice for every season** Whenever you want to travel, a warm welcome awaits you in Winchester. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in .  Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Winchester holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Winchester holiday rentals we have selected for you start as low as £95 per night. Entering your travel dates in the search wizard you might find even better deals! **How to find incredible deals on Winchester rentals** At Expedia, we put the best Winchester holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.  To find some top Winchester rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Winchester holiday. If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Winchester. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.  ## Explore a world of travel with Expedia - Trending destinations on Expedia.co.uk - All accommodation types in Winchester ### Trending destinations on Expedia.co.uk - [Holiday Rentals in the Cotswold](https://www.expedia.co.uk/lp/b/vr/cotswold) - [Holiday Rentals in Lake District](https://www.expedia.co.uk/lp/b/vr/lake-district) - [Devon Holiday Rentals](https://www.expedia.co.uk/Destinations-In-Devon.d6046196.Holiday-Rental-Destinations) - [Norfolk Holiday Rentals](https://www.expedia.co.uk/Destinations-In-Norfolk.d6046223.Holiday-Rental-Destinations) - [Bedfordshire Holiday Rentals](https://www.expedia.co.uk/Destinations-In-Bedfordshire.d6046189.Holiday-Rental-Destinations) - [Dorset Holiday Rentals](https://www.expedia.co.uk/Destinations-In-Dorset.d6046198.Holiday-Rental-Destinations) - [Northumberland Holiday Rentals](https://www.expedia.com/Destinations-In-Northumberland.d6046225.Vacation-Rental-Destinations) - [Herefordshire Holiday Rentals](https://www.expedia.co.uk/Destinations-In-Herefordshire.d6046203.Holiday-Rental-Destinations) - [Essex Holiday Rentals](https://www.expedia.co.uk/Destinations-In-Essex.d6046201.Holiday-Rental-Destinations) - [Cumbria Holiday Rentals](https://www.expedia.co.uk/Destinations-In-Cumbria.d6046194.Holiday-Rental-Destinations) - [Yorkshire Holiday Rentals](https://www.expedia.co.uk/Yorkshire-Holiday-Rentals.d6342462.Travel-Guide-HolidayRentals) - [South Wales Holiday Rentals](https://www.expedia.co.uk/South-Wales-Holiday-Rentals.d6054274.Travel-Guide-HolidayRentals) - [North Wales Holiday Rentals](https://www.expedia.co.uk/North-Wales-Holiday-Rentals.d6054276.Travel-Guide-HolidayRentals) - [London Holiday Rentals](https://www.expedia.co.uk/London-Holiday-Rentals.d178279.Travel-Guide-HolidayRentals) - [York Holiday Rentals](https://www.expedia.co.uk/York-Holiday-Rentals.d5489.Travel-Guide-HolidayRentals) - [Blackpool Holiday Rentals](https://www.expedia.co.uk/Blackpool-Holiday-Rentals.d619.Travel-Guide-HolidayRentals) - [Isle of Wight Holiday Rentals](https://www.expedia.com/Destinations-In-Isle-Of-Wight.d6046218.Vacation-Rental-Destinations) - [Scarborough Holiday Rentals](https://www.expedia.co.uk/Scarborough-Holiday-Rentals.d5680.Travel-Guide-HolidayRentals) - [Edinburgh Holiday Rentals](https://www.expedia.co.uk/Edinburgh-Holiday-Rentals.d6069845.Travel-Guide-HolidayRentals) - [Bath Holiday Rentals](https://www.expedia.co.uk/Bath-Holiday-Rentals.d6084496.Travel-Guide-HolidayRentals) - [Bournemouth Holiday Rentals](https://www.expedia.co.uk/Bournemouth-Holiday-Rentals.d654.Travel-Guide-HolidayRentals) - [England Holiday Rentals](https://www.expedia.co.uk/Destinations-In-England.d11218.Holiday-Rental-Destinations) - [Scotland Holiday Rentals](https://www.expedia.co.uk/Destinations-In-Scotland.d11219.Holiday-Rental-Destinations) - [Cornwall Holiday Rentals](https://www.expedia.co.uk/Destinations-In-Cornwall.d6046193.Holiday-Rental-Destinations) - [Wales Holiday Rentals](https://www.expedia.co.uk/Destinations-In-Wales.d11220.Holiday-Rental-Destinations) - [Northern Ireland Holiday Rentals](https://www.expedia.co.uk/Destinations-In-Northern-Ireland.d11221.Holiday-Rental-Destinations) - [Cabin Rentals in Winchester](https://expedia.co.uk/Winchester-Cabins.d6056879-aaCabins.Travel-Guide-Accommodation) - [B&B in Winchester](https://expedia.co.uk/Winchester-Bed-And-Breakfasts.d6056879-aaBedAndBreakfasts.Travel-Guide-Accommodation) - [Villas in Winchester](https://expedia.co.uk/Winchester-Villas.d6056879-aaVillas.Travel-Guide-Accommodation) ## Frequently asked questions ### Can I find holiday rentals in Winchester? > Yes, there are holiday rentals in Winchester close to Shenandoah Valley Discovery Museum, or you can select a more secluded option if you're looking for a relaxing stay. Tourists like the array of shops and top-notch restaurants in Winchester. You can also check out the theatre scene while you're visiting. ### What are some of the best holiday rentals that Winchester has to offer? > [Lone Bear Cabin: Lv2 EV, WiFi, River Access, Mountain Views, fireplace, hot tub](https://www.expedia.co.uk/Rileyville-Hotels-Lone-Bear-Cabin-Lv2-EV.h37274339.Hotel-Information): This holiday home rental outside of Winchester is located on a river, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday. ### How many holiday rentals will I find in Winchester? > Choose from 17 Expedia holiday rentals in Winchester for a memorable holiday. ### What’s there to see and do in Winchester? > Shenandoah Valley Discovery Museum and Nalls Farm Market are a couple of the family-friendly sights, whereas cultural attractions include Bright Box Theater and Winchester Little Theater. Other places in town to visit include Patsy Cline Historic House and Museum of the Shenandoah Valley. ### What’s a holiday rental in Winchester like? > Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Winchester. Holiday rentals offer extras like kitchens and laundry facilities so you'll feel just like you're at home. If you're concerned about cleanliness, a holiday rental can offer a sense of safety away from public hotel lifts and busy front desks while still allowing you the excitement and enjoyment of travel. You'll also get more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a great choice for a family getaway. ### Expedia's Latest Trends Hotels - [Hotels in Alexandria](https://expedia.co.uk/Alexandria-Hotels.d5980.Travel-Guide-Hotels) - [Hotels in Norfolk](https://expedia.co.uk/Norfolk-Hotels.d2689.Travel-Guide-Hotels) - [Hotels in Charlottesville](https://expedia.co.uk/Charlottesville-Hotels.d6057012.Travel-Guide-Hotels) - [Hotels in Virginia Beach](https://expedia.co.uk/Virginia-Beach-Hotels.d10271.Travel-Guide-Hotels) - [5 Star Syria Accommodation](https://expedia.co.uk/5Star-Syria-Hotels.s50-0-d184113.Travel-Guide-Filter-Hotels) - [Hotels in Roanoke](https://expedia.co.uk/Roanoke-Hotels.d3020.Travel-Guide-Hotels) Flights - [Cheap Flights to Williamsburg](https://expedia.co.uk/Cheap-Flights-To-Williamsburg.d6296.Travel-Guide-Flights) - [Flights from Sterling](https://expedia.co.uk/lp/flights/9843/flights-from-sterling) - [Cheap Flights to Palestine](https://expedia.co.uk/Cheap-Flights-To-Palestine.d9482.Travel-Guide-Flights) - [Cheap Flights to Virginia Beach](https://expedia.co.uk/Cheap-Flights-To-Virginia-Beach.d10271.Travel-Guide-Flights) - [Cheap Flights to Syria](https://expedia.co.uk/Cheap-Flights-To-Syria.d184113.Travel-Guide-Flights) - [Cheap Flights to Newport News](https://expedia.co.uk/Cheap-Flights-To-Newport-News.d6056964.Travel-Guide-Flights) - [Cheap Flights to Quantico](https://expedia.co.uk/Cheap-Flights-To-Quantico.d6204547.Travel-Guide-Flights) - [Flights from Syria](https://expedia.co.uk/lp/flights/184113/flights-from-syria) - [Cheap Flights to Damascus](https://expedia.co.uk/Cheap-Flights-To-Damascus.d6242026.Travel-Guide-Flights) - [Cheap Flights to North Pole](https://expedia.co.uk/Cheap-Flights-To-North-Pole.d182915.Travel-Guide-Flights) - [Cheap Flights to Charlottesville](https://expedia.co.uk/Cheap-Flights-To-Charlottesville.d6057012.Travel-Guide-Flights) - [Cheap Flights to Triangle](https://expedia.co.uk/Cheap-Flights-To-Triangle.d7335.Travel-Guide-Flights) - [Cheap Flights to San Diego](https://expedia.co.uk/Cheap-Flights-To-San-Diego.d3073.Travel-Guide-Flights) - [Cheap Flights to Roanoke](https://expedia.co.uk/Cheap-Flights-To-Roanoke.d3020.Travel-Guide-Flights) Activities - [Things to do in Norfolk](https://expedia.co.uk/Things-To-Do-In-Norfolk.d2689.Travel-Guide-Activities) - [Things to do in Suffolk](https://expedia.co.uk/Things-To-Do-In-Suffolk.d6981.Travel-Guide-Activities) Packages - [Damascus Holidays](https://expedia.co.uk/Damascus.d6242026.Holidays-City-Breaks) - [Virginia Beach Holidays](https://expedia.co.uk/Virginia-Beach.d10271.Holidays-City-Breaks) - [Charlottesville Holidays](https://expedia.co.uk/Charlottesville.d6057012.Holidays-City-Breaks) - [Syria Holidays](https://expedia.co.uk/Syria.d184113.Holidays-City-Breaks) - [Arvonia Holidays](https://expedia.co.uk/Arvonia.d3000355001.Holidays-City-Breaks) General - [Visit Surry](https://expedia.co.uk/Surry.dx3000460686) - [Visit Ashburn](https://expedia.co.uk/Ashburn.dx6035055) - [Visit Arvonia](https://expedia.co.uk/Arvonia.dx3000355001) ![](https://a.travel-assets.com/mad-service/footer/bnaBanners/BEX_Footer.jpg) ## Go further with the Expedia app Save on select hotels when you book in the app. Our app deals help you to save on trips so you can travel more and manage it all on the go. Scan the QR code with your device camera and download our app ![QR code to download the app](data:image/png;base64,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)