Family-friendly holiday rentals in Winthrop

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Top-rated family-friendly rentals in Winthrop

Guests agree: these family-friendly homes are highly rated for location, cleanliness and more.

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Guest favourite

Cabin in Skykomish

4.91 out of 5 average rating, 428 reviews

On The River

A River Runs Through It is your mountain retreat on the Skykomish/Tye river in the quiet neighborhood of Timberlane Village. Close to hiking trails, river rafting, Stevens Pass ski area (15 mins) and from Leavenworth (45 mins) you’ll love this cabin for its river views/sound, wooded property, secluded location, and cozy features like the wood stove, king size beds, cedar paneling throughout the home. A couples getaway, a solo adventure, or a family vacation, this cabin never ceases to impress.

8–15 Nov

$273 SGD per night

Guest favourite

Guest house in Leavenworth

4.99 out of 5 average rating, 475 reviews

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, much fresh air, and lots of natural light.

16–23 Jul

$456 SGD per night

Guest favourite

Home in Mazama

4.94 out of 5 average rating, 130 reviews

★ Cozy Cabin in the Woods ★ near Mazama/Winthrop

Blue Pine Guest House is in a quiet forested neighborhood just 3 miles from Mazama and 10 miles west of the 'Old West' town of Winthrop, WA. 2-bedroom, 2-bathroom home perfect base camp for your outdoor adventures. Summer activities: biking, hiking, climbing, fishing & river rafting. Winter: 200 km of groomed cross-country ski trails, fat biking, snow shoeing, and heli-skiing. Fall/Spring are our favorite seasons in the valley because it is less crowded and there's plenty to do.

26 Feb – 5 Mar

$422 SGD per night

Guest favourite

Townhouse in Winthrop

4.92 out of 5 average rating, 112 reviews

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 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, propane BBQ, and a propane fireplace. Excellent place for families with lots of toys, games, and child-friendly stuff.

17–24 Nov

$492 SGD per night

Guest favourite

Home in Winthrop, Washington, US

4.96 out of 5 average rating, 236 reviews

Artemisia: New Zero-Energy View Home—Walk to Town

This brand-new light-filled home is the perfect escape. Artemisia is within walking distance of the cafes, restaurants, and shopping of Winthrop but feels miles away. After an active day of skiing, hiking, fly fishing, or just relaxing, you can kick back and take in the expansive views of Mount Gardner. Have dinner at one of the many nearby restaurants or stay in and take advantage of the well-stocked kitchen with induction range. It's a peaceful, laid-back gathering place.

17–24 Nov

$316 SGD per night

Guest favourite

Flat in Winthrop

4.9 out of 5 average rating, 148 reviews

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.

16–23 Sep

$212 SGD per night

Guest favourite

Loft in Leavenworth, Washington, US

4.94 out of 5 average rating, 946 reviews

Bright, clean downtown Leavenworth loft

Our loft is the perfect place to stay while visiting Leavenworth. Our quiet neighborhood is just 1 block from Leavenworth's restaurants and shops. Local walking trails and river beaches are accessed right across the street. You'll enjoy having your own private entrance and parking spot. We offer self check-in and are low key hosts! We love our community and are here to answer any questions you may have and can recommend places to eat and trails to enjoy!

10–17 Oct

$205 SGD per night

Guest favourite

Chalet in Leavenworth

4.9 out of 5 average rating, 364 reviews

Cozy Fish Lake Chalet

Cute, Cozy & Quiet - Perfect place to get away and enjoy a relaxing vacation! Three-level mountain chalet, 6 beds, peek-a-boo view of beautiful Fish Lake with access to a private community fishing dock and boat launch. Enjoy a peaceful, relaxing vacation with your friends and family. Leavenworth and Stevens Pass are just a short drive away! (20-25 miles) Chelan County STR Permit #000492

9–16 May

$210 SGD per night

Guest favourite

Cabin in Okanogan County

4.91 out of 5 average rating, 249 reviews

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.

8–15 Oct

$204 SGD per night

Guest favourite

Flat in Leavenworth

4.94 out of 5 average rating, 566 reviews

The Chalet

This is our little chalet apartment located only two blocks from the center of town in a three unit building. It's super close to town but in a nice quiet area. The Chalet is entered from the right side and occupies the back half of the building. The patio area for the Chalet is in the back so you get a little more privacy.

26 Mar – 2 Apr

$159 SGD per night

Guest favourite

Cabin in Winthrop, Washington, US

4.94 out of 5 average rating, 174 reviews

May special! Cozy Mazama cabin.

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.

27 Sep – 4 Oct

$361 SGD per night

Guest favourite

Cabin in Winthrop

4.94 out of 5 average rating, 315 reviews

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.

18–25 Nov

$326 SGD per night