Oregon is filled with numerous attractions that can be enjoyed by people of all ages. If you are an avid skier, the state is known for its top-notch ski resorts such as Mount Hood Meadows and Timberline Lodge Ski Area. If you are fond of nature, admire the beauty of Multnomah Falls and explore the stunning crater lake surrounded by majestic pines and mountains at Crater Lake National Park. Be sure to enjoy diverse wildlife without having to leave your car when you come to Wildlife Safari. For your stay, read on to learn about the nine best ski-in ski-out accommodations in Oregon, USA.
We handpicked these listings carefully, considering (wherever possible) recent guest reviews, location, accommodation type, prices, availability of dates, decor, and access to ski slopes and equipment. The image galleries get refreshed with the latest updates regularly. They were last updated on October 24, 2025.
1. Bright house with a private hot tub (from USD 886)
A pleasant stay with your loved ones is guaranteed when you choose this bright house that is large enough to accommodate 15 people. The house features six bedrooms and three bathrooms along with other amenities such as a fully equipped kitchen, secure parking for five vehicles, and free WiFi. You are allowed to soak in the hot tub whenever you feel like relaxing. Enjoy a day of skiing at Skibowl that is right around the corner, or hop on the shuttle that can bring you to Mount Hood Meadows.
Government Camp, Oregon, United States
142.4 km (88.5 mi) from Drake Park
Top guest reviews
Location:
location was amazingnice location and spacious home great for a large groupnice place will definitely come backnice home tons of room great locationCleanliness:
clean spacious and great locationperfect location clean house lots of room hot tube for aching muscles after a day on the mountainRead more reviewsAmenities & Room:
loved the hot tub and japanese toilet seatsexcellent home for large family lots of beds and rooms
2. Lovely cabin with a spacious yard
Unwind and recharge at this log cabin that offers you an opportunity to observe wildlife in their natural habitat. Equipped with three bedrooms and one bathroom, the cabin is perfect for eight travelers. There is a spacious yard that makes an excellent spot for relaxation and breathing in the fresh air. For a memorable evening, fire up the gas grill and indulge in a barbecue. Willamette Pass Ski Resort is located just minutes away from the cabin. If you’re not an avid skier, you can also check out other attractions such as High Desert Museum and Sun Mountain Fun Center.
Crescent Lake, Oregon, United States
78.67 km (48.9 mi) from Drake Park
Top guest reviews
Host:
owners were super helpful and responsivegreat hosts well communicated and helpfulso overall its kind of a mix here great location helpful owners but the house needs workLocation:
it was perfect for our family ski trip and a beautiful locationthis place is a great place to stay for high mountain adventureRead more reviewsCleanliness:
pros: beds were comfortable clean linens very cozy log homethe hot tub was perfect and very clean
3. Elegant country house at the base of Elkhorn Mountains (from USD 514)
Welcome to this elegant country house that promises a tranquil stay for a large group of up to 20 people. Tucked into the base of the majestic Elkhorn Mountains, the house offers eight bedrooms and three bathrooms. Stay in touch with everyone back home by connecting to the free WiFi. Admire the hardwood floors, oriental carpets, antique furniture, and crystal chandeliers that adorn the house. Staying here, you are within minutes of getting to Elkhorn Trail for skiing.
Baker City, Oregon, United States
276.32 km (171.7 mi) from Drake Park
Top guest reviews
Host:
robin is a great hostbeautiful home surroundings easy owner to work withalthough we had a few hiccups with our stay robin coen was very helpful to everythingLocation:
a great property and locationthe property was the perfect location for a baker city area adventurethe house ended up being a perfect location to explore the areait's only ~15 minutes to the baker city downtown with it's adorable shops bakery etcbut when we arrived the pictures weren't even close to how beautiful this place wasRead more reviewsAmenities & Room:
we had access to sleds (it snowed ) and extra sleeping bags bedding interesting books games and dvd'swe especially enjoyed the cheese fairy & copper belt winery tasting room across from the historic hotelgood bear was perfect with its large kitchen many bedrooms & beautiful forest setting overlooking baker valley
4. Modest cottage with a gas fireplace (from USD 199)
Have a delightful stay at this modest cottage that was built in 1925. Situated in the historic Old Town of Bend, the cottage welcomes four people who can comfortably sleep in the two bedrooms available. Engage in Nordic skiing and attend Mount Bachelor winter events that are just minutes away from the cottage. Cable television is provided to keep you entertained during your stay. To ensure a warm ambiance during colder months, a gas fireplace is at your disposal.
Bend, Oregon, United States
652 meters (0.5 ft) from Drake Park
Top guest reviews
Host:
the owner/property manager colleen was very kind and responsive to any needs we hadthe owner was very responsive and quick to help with the one small hiccup we hadLocation:
a super cute house in a great locationthe location of this house is amazing quick walking distance to downtown and to old millgreat location close to walking to restaurants on the main street of bendjust a short walk to downtown or to the mill - it was perfect for our staywe enjoyed staying somewhere that we could walk out our door to access groceries restaurants shopping and exerciseCleanliness:
everything was clean and looked fantasticthe house was very clean and had everything we needed for our stayeverything was perfect -- clean comfortable well designed with a small secure fenced backyard area for our dogthe place is very clean comfortable and in a great locationRead more reviewsAmenities & Room:
there are even funny old cook books that made for hilarious reading at the breakfast table
5. Spectacular cabin with huge windows (from USD 561)
Come to relax at this cabin with the best people in your life. Offering three bedrooms and three bathrooms, the cabin is ideal for not more than eight people. In each bedroom, you can enjoy huge windows that bring in not only natural light but also amazing views of nature. The living room boasts heated floors and decorative rugs for indoor relaxation. If you prefer to unwind outdoors, the wrap-around deck that comes with Adirondack chairs awaits your presence. Cross-country skiing along with mountain biking and snowshoeing are some outdoor activities you can enjoy right out your door.
Bend, Oregon, United States
18.35 km (11.4 mi) from Drake Park
Top guest reviews
Host:
owners very friendly and helpfulthe owners were very helpful before during and after our stayLocation:
we enjoyed the quiet privacy of the locationthis is the perfect place to get away from everything disconnect and relaxperfect place to unplug and spend time with loved onesCleanliness:
place was very clean and cozyRead more reviewsAmenities & Room:
super comfortable well designed and equipped with three master suites and two separate living areaswell-equipped and very comfortable
6. Cute cottage with a private parking (from USD 132)
Nestled within walking distance to all the offerings of Jacksonville, the cute cottage can be occupied by three people. If you drive your own car, you can enjoy private parking for up to two vehicles. The kitchen is equipped with all the necessary appliances for your cooking and baking needs. For indoor entertainment, you can connect to the free WiFi or turn on the cable TV. Ski-in ski-out amenities are available within easy reach.
Jacksonville, Oregon, United States
235.04 km (146.1 mi) from Drake Park
Top guest reviews
Host:
the owners were friendly and welcominghost very gracious friendlyour hosts were wonderful and were always available if neededour hosts were not intrusive but were available for us super friendly and concerned with our well beingwalkable to anywhere in town and the owners are a lovely coupleLocation:
great location easy walk to all jacksonville has to offerwhat a perfect cozy place to stay in jville walking distance to everythinghighly recommend staying here if you need someplace close to the airport with a sweet hostessvery close to the road traffic noise was not an issue very restful comfortable and cleanRead more reviewsCleanliness:
excellent little cottage clean friendly hoststhe cottage was clean and the bed was very comfortablelovely clean and homey cottage perfect for two
7. Pet-friendly cabin with a wrap-around deck (from USD 240)
Experience an incredible stay when you choose this heavenly cabin located in a secluded area. Located just minutes away from Village Mall and Fort Rock Park, the cabin is excellent for eight people as it features three bedrooms and two bathrooms. Prepare a delicious dinner in the kitchen and relish it in the dining area with the romantic view of the wood-burning fireplace. The wrap-around deck comes with a barbecue grill for your indulgence. A large hot tub invites you to relax all the muscles after a long day. Cross-country skis or snowshoes are yours to enjoy in an instant.
Sunriver, Oregon, United States
21.31 km (13.3 mi) from Drake Park
Top guest reviews
Location:
the location is idealgreat location to mt bachelorit was walkable or close to many main attractions the river the playground & the villagenice area easy to walk aroundRead more reviewsCleanliness:
complex has a shared pool which is currently being monitored for occupancy and cleaned often due to covidthis adorable spot had everything we needed and we felt taken care of clean cute and fully appointedclean well appointed and close to everything in sunriver
8. Best Western Sandy Inn (from USD 143)
Ideally situated within a quick drive from Skibowl and Timberline Lodge, this hotel promises a scenic environment at all times. Guests are welcome to take a refreshing dip in the indoor swimming pool or work out to stay fit in the equipped exercise center. As for your room, it comes with a television, a private bathroom, and large windows among other amenities. Besides world-class skiing, guests can also engage in horseback riding, fishing, and golfing.
Best Western Sandy Inn
Address: 37465 Highway 26
167.39 km (104.1 mi) from Drake Park
9. Timberline Lodge (from USD 255)
Every day spent at this hotel is guaranteed to be filled with joy. Hidden deep within Mount Hood National Forest, the hotel features ski-to-door access for your convenience. You can relax in a rustically elegant room that boasts original handcrafted furnishings. When you are too lazy to go outside, stream your favorite movies on cable television. When you go to the bathroom, you can enjoy complimentary toiletries. Guests are invited to unwind in the hot tub at night. Drop by the on-site bar to sip your favorite drink before going to sleep. What is more, the hotel offers a ski school for first-time skiers.
Timberline Lodge
Address: 27500 East Timberline Road
144.82 km (90.0 mi) from Drake Park
Have a memorable winter experience in Oregon
There are plenty of activities that you can enjoy once you set foot in Oregon. Skiing, snowshoeing, horseback riding, and hiking are just some of them. For your next vacation in Beaver State, consider booking one of the accommodations listed above.
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