Title: Middletown Cottages | 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) ![](https://mediaim.expedia.com/destination/2/cc4669911702549b209190768b702758.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Stephanie Sutton # Search Middletown Cottage Rentals - ![](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 [Nov 28 - Nov 30](https://www.expedia.ca/Hotel-Search?regionId=12013&startDate=2025-11-28&endDate=2025-11-30&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Jan 9 - Jan 11](https://www.expedia.ca/Hotel-Search?regionId=12013&startDate=2026-01-09&endDate=2026-01-11&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three 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 four 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) ## Browse Select Middletown Cottages ![Outdoor spa tub](https://images.trvl-media.com/lodging/90000000/89680000/89671500/89671491/215d28e2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/90000000/89680000/89671500/89671491/40e0ea36.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/90000000/89680000/89671500/89671491/d2f7032a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, stereo](https://images.trvl-media.com/lodging/90000000/89680000/89671500/89671491/1920a52c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy Retreat - Hot tub + Mountain Views + Pets Fort Valley 9.8/10 Exceptional (52) "We loved our stay! The house was perfect and my girls just loved all the charm and little touches. The views on the property were gorgeous and it was a perfect location." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Danielle M. CA $91 CA $329 total includes taxes & fees Nov 13 - Nov 14 [](https://www.expedia.ca/Fort-Valley-Hotels-NEW-Mountain-Views-Cottage-Near-Shenandoah.h89671491.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/120000000/119500000/119496400/119496330/9a2bb6ad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace](https://images.trvl-media.com/lodging/120000000/119500000/119496400/119496330/59a5c7fc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/120000000/119500000/119496400/119496330/4c56e3e1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/120000000/119500000/119496400/119496330/b8a5d193.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### "Prima BnB" a Superb 4-bedroom cottage on the mountain near Front Royal Front Royal 10/10 Exceptional (2) "My family and I had a wonderful stay! The property and surrounding views are beautiful. The house was very clean and the host was very responsive when I had a question or two to ask. I highly recommend staying here!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jay L. CA $244 CA $625 total includes taxes & fees Dec 9 - Dec 10 [](https://www.expedia.ca/Front-Royal-Hotels-Prima-A-Superb-4-Bedroom-Cottage-On-The-Mountain-Near-Front-Royal.h119496330.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/108000000/107620000/107613900/107613898/a69388d0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/108000000/107620000/107613900/107613898/c2c2b573.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/108000000/107620000/107613900/107613898/c10ab8bb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![4 bedrooms, desk, iron/ironing board, WiFi](https://images.trvl-media.com/lodging/108000000/107620000/107613900/107613898/1087f0c8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Vue - Mountain top hot tub overlooking the Shenandoah River Front Royal 9.8/10 Exceptional (8) "Love the view and beautiful appointed decor throughout the home…" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lynn M. CA $252 CA $571 total includes taxes & fees Nov 24 - Nov 25 [](https://www.expedia.ca/Front-Royal-Hotels-The-Vue-Mountain-Top-Hot-Tub-Overlooking-The-Shenandoah-River.h107613898.Hotel-Information) ![Outdoor spa tub](https://images.trvl-media.com/lodging/86000000/85480000/85477500/85477424/a06f20db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/86000000/85480000/85477500/85477424/042e58ea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![4 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/86000000/85480000/85477500/85477424/ed64133f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/86000000/85480000/85477500/85477424/47d3b88f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Pets? YES! 🐕 Hot Tub ★ Fire Pit ★ Fast Wi-Fi Boyce 9.8/10 Exceptional (30) "My husband and I stayed here the week before Christmas. Once we arrived, the first thing I noticed was the Christmas tree in the living room. I was very pleased the house was decorated. We had a wonderful stay and would definitely come back. The train didn’t bother us at all. Very quiet. Thank you for making our stay magical!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Andrea M. CA $318 CA $788 total includes taxes & fees Nov 24 - Nov 25 [](https://www.expedia.ca/Boyce-Hotels-NEW-WINE-COUNTRY-ESCAPE-Hot-Tub-Fire-Pit-Fast-Wi-Fi-Gas-Grill.h85477424.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=2025-11-25&endDate=2025-11-26®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-Cottages.d12013-aaCottages.Travel-Guide-Accommodation)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FMiddletown-Cottages.d12013-aaCottages.Travel-Guide-Accommodation) ## Top Middletown Hotel Reviews ![Holiday Inn Express Woodstock-Shenandoah Valley by IHG](//images.trvl-media.com/lodging/1000000/30000/20600/20598/e45798f9_y.jpg) ### Holiday Inn Express Woodstock-Shenandoah Valley by IHG 10/10 Excellent "I always stop at this hotel on my way down to my son’s home in North Carolina. I feel safe and am very familiar with the places around the area. The rooms are always spotless. It’s convenient as it’s right off the highway. " [](https://expedia.ca/Luray-Hotels-Holiday-Inn-Express-Woodstock-Shenandoah-Valley.h20598.Hotel-Information) ![Ramada by Wyndham Strasburg/Shenandoah Valley](//images.trvl-media.com/lodging/2000000/1250000/1246400/1246311/08da8378_y.jpg) ### Ramada by Wyndham Strasburg/Shenandoah Valley 10/10 Excellent "Wonderful and accommodating as usual" [](https://expedia.ca/Winchester-Hotels-Ramada-By-Wyndham-Strasburg.h1246311.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 "Excellent accommodations" [](https://expedia.ca/Winchester-Hotels-Microtel-Inn-Suites-By-Wyndham-Winchester.h70921061.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 "Good" [](https://expedia.ca/Winchester-Hotels-Country-Inn-Suites-By-Radisson.h1652833.Hotel-Information) ![TRU By Hilton Winchester](//images.trvl-media.com/lodging/40000000/39500000/39493500/39493421/b9c1387b_y.jpg) ### TRU By Hilton Winchester 10/10 Excellent "The hotel was clean and the staff was pleasant." [](https://expedia.ca/Winchester-Hotels-TRU-By-Hilton-Winchester.h39493421.Hotel-Information) ![DoubleTree by Hilton Front Royal Blue Ridge Shadows](//images.trvl-media.com/lodging/2000000/1890000/1889100/1889081/204cbf3a_y.jpg) ### DoubleTree by Hilton Front Royal Blue Ridge Shadows 10/10 Excellent "Friendly staff" [](https://expedia.ca/Front-Royal-Hotels-Holiday-Inn-Suites-Front-Royal-Blue-Ridge-Shadows.h1889081.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 "Such a great find for our overnight Stay and last minute with excellent price. Comfortable bed and fantastic staff. Breakfast lacking but expected. " [](https://expedia.ca/Winchester-Hotels-Travelodge-By-Wyndham-Winchester.h9600.Hotel-Information) ![Comfort Inn & Suites Winchester](//images.trvl-media.com/lodging/58000000/57960000/57958300/57958244/cf4c2663_y.jpg) ### Comfort Inn & Suites Winchester 10/10 Excellent "It was the cleanest and most friendly place I’ve ever stayed at.The breakfast was amazing the beds were very comfortable hardly any noise just a great place to stay." [](https://expedia.ca/Winchester-Hotels-Comfort-Inn-Suites.h57958244.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 in all ways. Fresh, modern hotel. Big rooms." [](https://expedia.ca/Winchester-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Winchester.h2678524.Hotel-Information) ## Find out more about Middletown ## Middletown Cottages information | Number of reviews | | | --- | --- | | Accommodation | Cottages | | Lowest Price | | | Highest Price | | ## Frequently asked questions ### Why book your cottage in Middletown with Expedia? > Expedia has some wonderful cottages in Middletown, so start packing your bags for an unforgettable vacay on nature's doorstep. If you have a budget, choose how much you want to spend and the preferred star rating of your property. Or, use our handy filters to search for cottages with free WiFi or a pool. We'll help you find the perfect pad whatever your style of travel or plans. ### How can I find cheap cottages in Middletown? > With Expedia's handy filter tool, comparing cheap cottages in Middletown is easy. To view properties that are friendly on the wallet, refine your search by star rating, budget and amenities. ### What is there to do in Middletown near my cottage? > After you've unpacked your bags and settled in, get out and discover the incredible things Middletown has for you to experience. [Belle Grove Plantation](https://www.expedia.ca/Belle-Grove-Plantation-Middletown.d6164020.Vacation-Attraction) is a great attraction to add to your must-do list. ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - More ways to book - [4 Star Hotels in Stephens City](https://www.expedia.ca/4Star-Stephens-City-Hotels.s40-0-d12076.Travel-Guide-Filter-Hotels) - [Hotels near Apple Blossom Mall](https://www.expedia.ca/Apple-Blossom-Mall-Hotels.0-l6164018-0.Travel-Guide-Filter-Hotels) - [Hotels near Blue Ridge Shadows Golf Club](https://www.expedia.ca/Blue-Ridge-Shadows-Golf-Club-Hotels.0-l553248621532661832-0.Travel-Guide-Filter-Hotels) - [Apartments in Boyce](https://www.expedia.ca/Boyce-Apartments.d184084-aaApartments.Travel-Guide-Accommodation) - [B&B in Boyce](https://www.expedia.ca/Boyce-Bed-And-Breakfast.d184084-aaBedAndBreakfast.Travel-Guide-Accommodation) - [B&B in College Park](https://www.expedia.ca/College-Park-Bed-And-Breakfast.d553248635975870482-aaBedAndBreakfast.Travel-Guide-Accommodation) - 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[Flights from Winchester Regional](https://www.expedia.ca/lp/airports/wgo/flights-from-winchester-regional-airport) - [Flights from Star Tannery](https://www.expedia.ca/lp/flights/3000460674/flights-from-star-tannery) - [Flights from Blacksburg (BCB) to Winchester (WGO)](https://www.expedia.ca/lp/flights/bcb/wgo/blacksburg-to-winchester) - [Flights from Hartford (BDL) to Winchester (WGO)](https://www.expedia.ca/lp/flights/bdl/wgo/hartford-to-winchester) - [Flights from Baltimore (BWI) to Front Royal (FRR)](https://www.expedia.ca/lp/flights/bwi/frr/baltimore-to-front-royal) - [Flights from Baltimore (BWI) to Winchester (WGO)](https://www.expedia.ca/lp/flights/bwi/wgo/baltimore-to-winchester) - [Flights from Denver (DEN) to Winchester (WGO)](https://www.expedia.ca/lp/flights/den/wgo/denver-to-winchester) - [Flights from Dallas (DFW) to Winchester (WGO)](https://www.expedia.ca/lp/flights/dfw/wgo/dallas-to-winchester) - [Flights from El Paso (ELP) to Winchester (WGO)](https://www.expedia.ca/lp/flights/elp/wgo/el-paso-to-winchester) - 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[Front Royal Entrance Shenandoah National Park](https://www.expedia.ca/Front-Royal-Entrance-Shenandoah-National-Park-Front-Royal.d6129961.Vacation-Attraction) - [Skyline Caverns](https://www.expedia.ca/Skyline-Caverns-Front-Royal.d6093201.Vacation-Attraction) - [Budget Rental Cars in Front Royal](https://www.expedia.ca/Budget-Car-Rentals-In-Front-Royal.d7312-c39.Car-Rental-Guide-Suppliers) - [Car rental Front Royal](https://www.expedia.ca/Car-Rentals-In-Front-Royal.d7312.Car-Rental-Guide) - [Book Cottages in Middletown on Expedia.com](https://www.expedia.com/Middletown-Cottages.d12013-aaCottages.Travel-Guide-Accommodation)