Family-friendly holiday rentals in Winthrop

Contemporary Guesthouse in Town

"The Shedd" used to be a shed before our architect got a hold of it and turned it into a retreat for writing, reading, and napping. The 800 sq. ft. guesthouse has a bedroom, bathroom w/ walk-in shower, small kitchen, dining nook, sitting area, desk, wifi, and A/C. Even though it's just a 7-minute walk to the village, our place backs up to the wilderness, with great views of Tumwater Mountain and Icicle Ridge. Best of all, The Shedd has many windows and lots of fresh air and natural light.

Alpine Woods cabin close to trails, ski in/out

Walk to the Methow Valley Community Trail along the river and suspension bridge or choose the best trails for you within a short drive. The property features a long driveway set back in the woods for a private feel. 2 bedroom, 2 full bath cabin features an open floor plan with high ceilings and home entertainment system. Plowed flat roads make for easy access in winter. Close to the Methow Valley and North Cascade Trails - 3.5 miles from the Mazama store and 11 miles to downtown Winthrop.

Riverside Avenue Retreat in Downtown Winthrop

Riverside Avenue Retreat(a legal, licensed nightly rental with a current Okanogan County health permit as required by law) is located right in the heart of downtown Winthrop, and is close to the old western boardwalk, shops and eateries. It is a complete apartment suite where you can stay for awhile. There is a King bed, a gorgeous fireplace setting, Smart TV and a comfortable Queen size sofa sleeper, and so much more. Shared parking is available behind building.

All Seasons Mountain Retreat-Ski in/out- WiFi 150

Ski in/ ski out, bike and hike to famous Methow cross-country trails and town! Fastest WiFi in Methow 148+Mbps 220 volt Tesla EV charger access May 1, 2025 Close to everything you need, including trails, dining, cinema, and shopping. Modern conveniences in the pristine beauty of the Methow Valley - air conditioners, smart TVs, new appliances, new carpet, King size sleep number bed, a lovely patio, and a propane fireplace. Excellent place for families

Mazama Unplugged

This cozy modern cabin is in the heart of Mazama just 6 miles from the Mazama store and minutes from hiking and ski trails. The cabin is NOT a secluded cabin in the woods as you can see other houses around you and it is close to Lost River Road. But the road ends just north of the cabin and it is the "end of line" for Mazama and the Methow Valley, so the area remains fairly quiet. **PLEASE SEE NOTE BELOW regarding Smoke & Fire Season during the Summer.

Underground Hygge 🍄

This inspired dwelling nestled right into the breathtaking Columbia River Gorge mountainside. Reverently framed by the iconic round doorway, the wondrous views will entrance your imagination and inspire an unforgettable journey. Every nook of this little habitation will warm your sole, every cranny will charm your expedition of repose. Up the pathway, tucked into the earth, an unbelievable adventure awaits!

Sunny Pines cabin on Fawn Creek

Relaxing and cozy cabin in the middle of the woods has all the comforts of home. Sit by the fire and watch the snow fall after a day skiing or plan your next day's hike while you sit out on the deck listening to the rushing creek. This 3-bedroom cabin has two bathrooms, upstairs and downstairs decks and a river-rock gas fireplace.

Cozy cabin in ideal spot, perfect for all seasons!

Our Mazama cabin in an approved legal nightly rental community! Great location only 5 mins. to the Mazama store, Mazama Pub and a short 10 mins. from Winthrop, hundreds of miles of ski, snowshoe and bike trails (fat bikes available for rental in Winthrop!), the Methow River & amazing hikes.

Lovely Log Cabin on the River and MVSTA Trail

Our delightful log cabin is perfect for a Methow Valley get-away. We are tucked in a lovely grove of aspens, one minute walk to the Methow River, private sauna, shared hot tub & pool and MVSTA trail (1-2 minute walk/ski). The cabin has two bedrooms + a sleeping loft and a full kitchen.