Family-friendly vacation 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 favorite

Cabin in Skykomish

4.91 out of 5 average rating, 427 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.

Nov 14 – 21

R3,735 ZAR per night

Guest favorite

Guesthouse 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.

Dec 27 – Jan 3

R6,054 ZAR per night

Guest favorite

Guest suite in Cashmere

4.91 out of 5 average rating, 560 reviews

Cozy Cabin Hideaway with great views

We do have dogs on the premise. If you're looking for the great outdoors with a view, this is it. All or 4 wheel drive necessary in winter. Country living with deer, goats, rabbits and more. The guest suite is the basement, and is all yours to enjoy. Creaky floors in Rustic bedroom (new ceiling, but still hear some creaky and dogs). Sulphur smell occasionally in water. RO drinking faucet installed in kitchen. Bring directions provided by me. Stairs to the basement apartment.

Sep 21 – 28

R2,719 ZAR per night

Guest favorite

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.

Apr 13 – 20

R5,544 ZAR per night

Guest favorite

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.

Apr 4 – 11

R6,739 ZAR per night

Guest favorite

Home in Winthrop

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.

Nov 17 – 24

R4,327 ZAR per night

Guest favorite

Apartment 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.

Sep 16 – 23

R2,899 ZAR per night

Guest favorite

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!

Oct 22 – 29

R2,689 ZAR per night

Guest favorite

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

May 8 – 15

R2,878 ZAR per night

Guest favorite

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.

Sep 13 – 20

R2,793 ZAR per night

Guest favorite

Apartment 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.

Mar 27 – Apr 3

R2,180 ZAR per night

Guest favorite

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.

Sep 27 – Oct 4

R4,941 ZAR per night