Title: Hillside Vacation Rentals from $165: Search Short-Term Rentals | Expedia.com [Hillside Travel Guide](https://expedia.com/Hillside.dx6348416)[Hotels in Hillside](https://expedia.com/Hillside-Hotels.d6348416.Travel-Guide-Hotels)[Flights to Hillside](https://expedia.com/Cheap-Flights-To-Hillside.d6348416.Travel-Guide-Flights)[Car Rentals in Hillside](https://expedia.com/Car-Rentals-In-Hillside.d6348416.Car-Rental-Guide)[Hillside Vacation Packages](https://expedia.com/Hillside.d6348416.Destination-Travel-Guides) ![Default HTG hotel image](https://a.travel-assets.com/travel-assets-manager/32a5a1b7-682e-4c22-a8ab-4b736795e0ea/expedia_fallback.webp?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://a.travel-assets.com/travel-assets-manager/32a5a1b7-682e-4c22-a8ab-4b736795e0ea/expedia_fallback.webp?impolicy=fcrop&w=1200&h=500&q=medium) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light_bundle_and_save.svg) ### Bundle & Save Get more, spend less whenever you see Bundle & Save deals - ![](https://a.travel-assets.com/travel-assets-manager/pictograms-expedia/light__onekey.svg) ### OneKeyCash Earn OneKeyCash on all your eligible bookings - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light_ftc.svg) ### Upfront pricing We are not like the others - we include taxes and fees ## Check prices for these dates In two weeks [Mar 6 - Mar 8](https://www.expedia.com/Hotel-Search?regionId=6348416&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 two months [Apr 17 - Apr 19](https://www.expedia.com/Hotel-Search?regionId=6348416&startDate=2026-04-17&endDate=2026-04-19&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [May 15 - May 17](https://www.expedia.com/Hotel-Search?regionId=6348416&startDate=2026-05-15&endDate=2026-05-17&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [Jun 12 - Jun 14](https://www.expedia.com/Hotel-Search?regionId=6348416&startDate=2026-06-12&endDate=2026-06-14&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Hillside vacation rentals ![Family Studio Suite, Kitchen, Mountain View (Pet Free) | Mountain view](https://images.trvl-media.com/lodging/13000000/12430000/12425300/12425252/39a40719.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Panoramic House, 4 Bedrooms, Kitchen, Mountain View (Pet Free) | Soundproofing, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/13000000/12430000/12425300/12425252/6727dca1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Family Studio Suite, Kitchen, Mountain View (Pet Free) | Soundproofing, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/13000000/12430000/12425300/12425252/11067608.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/13000000/12430000/12425300/12425252/03538302.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hillside Colorado Cottages near Westcliffe [](https://www.expedia.com/Hillside-Hotels-Hillside-Colorado-Cottages-Near-Westcliffe.h12425252.Hotel-Information) Hillside 9.6/10 Exceptional (89 reviews) "Great property, great location, everything was splendid and well provisioned! Will definitely be on my list of places to re-visit. The Dark Sky was amazing! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Benjamin $154 nightly $165 total Feb 23 - Feb 24 Total with taxes and fees [](https://www.expedia.com/Hillside-Hotels-Hillside-Colorado-Cottages-Near-Westcliffe.h12425252.Hotel-Information) Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply. [View all properties](https://expedia.com/Hotel-Search?startDate=2026-03-08&endDate=2026-03-09®ionId=6348416&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true) ![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-us-ca.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## The Annual Vacation Sale Members save up to 40% on hotels and homes. Plan this year’s big trip and save. [Book now](https://expedia.com/deals?rfrr=VR_SPRING_PROMO_6348416) ## Find vacation rentals that suit your style Cabins [](https://www.expedia.com/Hotel-Search?destination=Hillside%2C+Colorado%2C+United+States+of+America®ionId=6348416&latLong=38.265278%2C-105.611671&adults=2&startDate=2026-05-23&d1=2026-05-23&endDate=2026-05-26&d2=2026-05-26&lodging=CABIN) Private vacation homes [](https://www.expedia.com/Hotel-Search?destination=Hillside%2C+Colorado%2C+United+States+of+America®ionId=6348416&latLong=38.265278%2C-105.611671&adults=2&startDate=2026-05-23&d1=2026-05-23&endDate=2026-05-26&d2=2026-05-26&lodging=VACATION_HOME) Cottages [](https://www.expedia.com/Hotel-Search?destination=Hillside%2C+Colorado%2C+United+States+of+America®ionId=6348416&latLong=38.265278%2C-105.611671&adults=2&startDate=2026-05-23&d1=2026-05-23&endDate=2026-05-26&d2=2026-05-26&lodging=COTTAGE) Apartments [](https://www.expedia.com/Hotel-Search?destination=Hillside%2C+Colorado%2C+United+States+of+America®ionId=6348416&latLong=38.265278%2C-105.611671&adults=2&startDate=2026-05-23&d1=2026-05-23&endDate=2026-05-26&d2=2026-05-26&lodging=APARTMENT) ![](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%2FHillside-Vacation-Rentals.d6348416.Travel-Guide-VacationRentals)[ Sign up, it's free ](https://expedia.com/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FHillside-Vacation-Rentals.d6348416.Travel-Guide-VacationRentals) ## Top Hillside Hotel Reviews !['The Hideaway' - Tucked in the Beautiful Wet Mountain Valley.](https://images.trvl-media.com/lodging/34000000/33510000/33500700/33500699/6cbadff5_y.jpg) ### 'The Hideaway' - Tucked in the Beautiful Wet Mountain Valley. 10/10 Excellent "It was a beautiful house and property and it was overall really clean. We even saw some deer on the driveway up. " [](https://expedia.com/Westcliffe-Hotels-The-Hideaway-Tucked-In-The-Beautiful-Wet-Mountain-Valley.h33500699.Hotel-Information) ![Super Cozy A-Frame in Howard, Colorado](https://images.trvl-media.com/lodging/111000000/110800000/110797400/110797373/70a62bd7_y.jpg) ### Super Cozy A-Frame in Howard, Colorado 10/10 Excellent "The kitchen was amazing! Beds were comfy. And it was just the right amount of space. One of our favorite stays weve ever been to." [](https://expedia.com/Howard-Hotels-Super-Cozy-A-Frame-In-Howard.h110797373.Hotel-Information) ![Dog Friendly- Star Mesa!](https://images.trvl-media.com/lodging/22000000/21710000/21705800/21705758/48502904_y.jpg) ### Dog Friendly- Star Mesa! 10/10 Excellent "Very peaceful location, accommodation was clean and had everything we needed for our stay" [](https://expedia.com/Howard-Hotels-Dog-Friendly-Star-Mesa.h21705758.Hotel-Information) ![Hillside Colorado Cottages near Westcliffe](https://images.trvl-media.com/lodging/13000000/12430000/12425300/12425252/39a40719_y.jpg) ### Hillside Colorado Cottages near Westcliffe 10/10 Excellent "Place was very clean, nice area, and felt safe. Our pup enjoyed it very much." [](https://expedia.com/Hillside-Hotels-Hillside-Colorado-Cottages-Near-Westcliffe.h12425252.Hotel-Information) ![Buckskin Joe's Cabin](https://images.trvl-media.com/lodging/106000000/105800000/105791200/105791170/079ef504_y.jpg) ### Buckskin Joe's Cabin 10/10 Excellent "My wife and I had a wonderful stay at the cabin! It was exactly what we needed. Beautiful surroundings and no noise. The cabin had very nice touches and we were very comfortable. We both definitely recommend." [](https://expedia.com/Howard-Hotels-Buckskin-Joes-Cabin.h105791170.Hotel-Information) ![Get Away From it All at Whiskey Rapids! Dog Friendly!](https://images.trvl-media.com/lodging/67000000/66910000/66904200/66904134/2b936cfb_y.jpg) ### Get Away From it All at Whiskey Rapids! Dog Friendly! 10/10 Excellent "Great host, beautiful location, cozy cute cabin, many extra amenities for guests pleasure and convenience! We would definitely stay here again!" [](https://expedia.com/Howard-Hotels-Get-Away-From-It-All-At-Whiskey-Rapids-Dog-Friendly.h66904134.Hotel-Information) ![Spacious Westcliffe Home: Hot Tub, StarLink, Views!](https://images.trvl-media.com/lodging/28000000/27140000/27130900/27130889/33edaa05_y.jpg) ### Spacious Westcliffe Home: Hot Tub, StarLink, Views! 10/10 Excellent "The host communicated very effectively with us before , during and after the stay. We appreciated his “checking” in. We had not experienced that in other VRBO rentals.The house was a perfect solution for our family- big open living room, dining area and kitchen. Hot tub was a hit as well.And, beautiful views!" [](https://expedia.com/Westcliffe-Hotels-Pet-Friendly-Ranch-W-StarLink-Hot-Tub-Special-Until-April.h27130889.Hotel-Information) ![Quiet, Cozy and Quaint Log Cabin Living!](https://images.trvl-media.com/lodging/46000000/45150000/45145700/45145647/d0454195_y.jpg) ### Quiet, Cozy and Quaint Log Cabin Living! 10/10 Excellent "This was an amazing cabin with outstanding views! It was quiet and so relaxing. Everything was perfect and clean. My husband and I came up for a well needed break and it checked all the boxes. We will definitely be back!" [](https://expedia.com/Cotopaxi-Hotels-Quiet.h45145647.Hotel-Information) ![Spanish Ranch on the Arkansas River- enjoy the rushing river from the Hot tub!](https://images.trvl-media.com/lodging/34000000/33750000/33743900/33743881/w848h565x1y1-14c034c2_y.jpg) ### Spanish Ranch on the Arkansas River- enjoy the rushing river from the Hot tub! 10/10 Excellent "Clean, scenic spot. Lots of amenities including game room, hot tub, outdoor games, private drive loop, well supplied kitchen. Bedrooms with extra blankets, cots, tvs. " [](https://expedia.com/Howard-Hotels-Spanish-Ranch-On-The-Arkansas-River-Enjoy-The-Rushing-River-From-The-Hot-Tub.h33743881.Hotel-Information) ## Find out more about Hillside **Everything you need to know about Hillside vacation rentals** Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Hillside vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 Hillside vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. **Hillside vacation rentals: An excellent choice for every season** Whenever you want to travel, a warm welcome awaits you in Hillside. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Hillside in high season. Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $165 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals! **How to find incredible deals on Hillside rentals** At Expedia, we put the best Hillside vacation 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 Hillside 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 Hillside vacation. If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Hillside. 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.com - All accommodation types in Hillside ### Trending destinations on Expedia.com - [Destin Vacation Rentals ](https://www.expedia.com/Destin-Vacation-Rentals.d6906.Travel-Guide-VacationRentals) - [Panama City Vacation Rentals ](https://www.expedia.com/Panama-City-Beach-Vacation-Rentals.d8021.Travel-Guide-VacationRentals) - [Hilton Head Vacation Rentals ](https://www.expedia.com/Hilton-Head-Island-Vacation-Rentals.d601684.Travel-Guide-VacationRentals) - [Gulf Shores Vacation Rentals ](https://www.expedia.com/Gulf-Shores-Vacation-Rentals.d603078.Travel-Guide-VacationRentals) - [Key West Vacation Rentals ](https://www.expedia.com/Key-West-Vacation-Rentals.d1187.Travel-Guide-VacationRentals) - [Gatlinburg Vacation Rentals ](https://www.expedia.com/Gatlinburg-Vacation-Rentals.d7474.Travel-Guide-VacationRentals) - [Maui Vacation Rentals ](https://www.expedia.com/Maui-Vacation-Rentals.d180073.Travel-Guide-VacationRentals) - [Orlando Vacation Rentals ](https://www.expedia.com/Orlando-Vacation-Rentals.d178294.Travel-Guide-VacationRentals) - [Myrtle Beach Vacation Rentals ](https://www.expedia.com/Myrtle-Beach-Vacation-Rentals.d601685.Travel-Guide-VacationRentals) - [Orange Beach Vacation Rentals ](https://www.expedia.com/Orange-Beach-Vacation-Rentals.d9136.Travel-Guide-VacationRentals) - [Pigeon Forge Vacation Rentals ](https://www.expedia.com/Pigeon-Forge-Vacation-Rentals.d8264.Travel-Guide-VacationRentals) - [Ocean City Vacation Rentals ](https://www.expedia.com/Ocean-City-Vacation-Rentals.d9151.Travel-Guide-VacationRentals) - [Outer Banks Vacation Rentals ](https://www.expedia.com/Outer-Banks-Vacation-Rentals.d602135.Travel-Guide-VacationRentals) - [San Diego Vacation Rentals ](https://www.expedia.com/San-Diego-Vacation-Rentals.d3073.Travel-Guide-VacationRentals) - [Siesta Key Vacation Rentals ](https://www.expedia.com/Siesta-Key-Vacation-Rentals.d6881.Travel-Guide-VacationRentals) - [Galveston Vacation Rentals ](https://www.expedia.com/Galveston-Vacation-Rentals.d1341.Travel-Guide-VacationRentals) - [Clearwater Beach Vacation Rentals ](https://www.expedia.com/Clearwater-Beach-Vacation-Rentals.d10759.Travel-Guide-VacationRentals) - [Palm Springs Vacation Rentals ](https://www.expedia.com/Palm-Springs-Vacation-Rentals.d180676.Travel-Guide-VacationRentals) - [Florida Keys Vacation Rentals ](https://www.expedia.com/Florida-Keys-Vacation-Rentals.d6023765.Travel-Guide-VacationRentals) - [Lake Tahoe Vacation Rentals ](https://www.expedia.com/South-Lake-Tahoe-Vacation-Rentals.d10150.Travel-Guide-VacationRentals) - [Lake of the Ozarks Vacation Rentals ](https://www.expedia.com/Lake-Ozark-Vacation-Rentals.d177772.Travel-Guide-VacationRentals) - [Florida Vacation Rentals ](https://www.expedia.com/Destinations-In-Florida.d211.Vacation-Rental-Destinations) - [Hawaii Vacation Rentals ](https://www.expedia.com/Destinations-In-Hawaii.d213.Vacation-Rental-Destinations) - [Michigan Vacation Rentals ](https://www.expedia.com/Destinations-In-Michigan.d224.Vacation-Rental-Destinations) - [Vacation Homes in Hillside ](https://expedia.com/Hillside-Private-Vacation-Homes.d6348416-aaPrivateVacationHomes.Travel-Guide-Accommodation) - [Cabin Rentals in Hillside ](https://expedia.com/Hillside-Cabins.d6348416-aaCabins.Travel-Guide-Accommodation) - [Cottages in Hillside ](https://expedia.com/Hillside-Cottages.d6348416-aaCottages.Travel-Guide-Accommodation) - [Apartments in Hillside ](https://expedia.com/Hillside-Apartments.d6348416-aaApartments.Travel-Guide-Accommodation) - [Lodges in Hillside ](https://expedia.com/Hillside-Lodges.d6348416-aaLodges.Travel-Guide-Accommodation) - [Motels in Hillside ](https://expedia.com/Hillside-Motels.d6348416-aaMotels.Travel-Guide-Accommodation) ## Frequently asked questions ### Are there vacation rentals in Hillside? 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