Family-friendly holiday rentals in Leavenworth

Luxury Black Forest Cabin near Leavenworth

STR Permit #000582 This luxury Black Forest–style cabin is located just 20 minutes from Leavenworth, near Coles Corner, with easy year-round access. 🛏️ Sleeps 6 - 3 bedrooms (3 king beds, each has a bathroom) 🛁 Private hot tub, forest view deck & firepit 🌲 2.5 wooded acres, peaceful & private 🔥 Fireplace, Smart TV, fast Wi‑Fi 🍳 Fully equipped kitchen + outdoor grill 👤 On-site caretaker in a separate ADU ensures a smooth and enjoyable stay 🔌 Tesla charger Max guests: 6, including children

PNW Hideout Cabin. Modern cabin in the woods!

Tucked away on 2.5 acres of wooded seclusion, the PNW Hideout blends modern amenities with nature. Walk 3 minutes to the beautiful River, drive 15 minutes to Lake Wenatchee, or enjoy all the wonderful activities just minutes away in Plain. High speed fiber internet makes the cabin a work-from-home paradise. Enjoy the spacious yard roasting marshmallows around the fire pit, soaking in the hot tub, or lounging inside with a wood burning fire. Located 20 miles from downtown Leavenworth. STR#000267

Grinning Bear Cabin

Grinning Bear Cabin is nestled in the beautiful Plain Valley 25 min outside of Leavenworth. This 2+bedroom, 2-bath home easily sleeps 4 and is set on 2/3 of acre. It offers a comfortable kitchen, hot tub, AC, heated bathroom floors, and ample space for family gathering and games. Grinning Bear Cabin allows you to escape into Chelan Co located between two ski resorts to enjoy downhill & XC skiing, snowboarding, hiking, mtn & road biking, fishing, and water adventures. Caretaker lives nearby.

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.

The Overlook - Modern Leavenworth Cabin

Ready to make your friends jealous? With a retractable wall for indoor/outdoor living, a real wood burning fireplace, unreal views of the river, this modern cliffhanging home above the Wenatchee river and in the heart of Leavenworth (only a 2min drive to town!) this cabin will help you unwind and relax! The heat lamps on the deck during the winter or the a/c inside during the summer, you are sure to enjoy your stay at The Overlook **SNOW ADVISORY** please make sure your car is AWD or 4WD.

Osprey Acres: Modern Suite, HotTub, Hiking Trails

If you desire a wonderland forest escape, you've come to the right place. Osprey Acres is a dreamy retreat that's perfect for isolation - it's next to the Wenatchee Natl. Forest in the quaint community of Plain, WA. Our property is nestled into nature. Just steps away, you'll discover private hiking and mountain bike trails. And you're within easy reach of Leavenworth, Stevens Pass Ski Resort, Lake Wenatchee and miles of mountain beauty. We open our home to people of all backgrounds.

Camp Howard

Camp Howard, built in 2018, was designed to blend modern luxury into the expansive nature of Nason Ridge. The home sits 2000 feet above sea level, perched on top of 5 acres of ponderosa forest in the foothills of Cashmere mountain. The rarities of the Pacific Northwest are a short drive away: Alpine skiing 25 minutes to the west at Stevens Pass, Bavarian treats 20 minutes south in Leavenworth, and recreation at Lake Wenatchee just moments north. Chelan County STR 000476

Gorgeous 2BR/2BA Condo in downtown Leavenworth

Experience the heart of downtown Leavenworth at Wunderbar Condos, with breathtaking views of the Wenatchee River and Cascade Mountains. These first or second floor two-bedroom condos sleep up to four guests in a Queen bedroom with full ensuite bath, a King bedroom with adjacent full bath, living and dining areas, fully equipped kitchen, and cozy electric fireplace. While specific units aren’t guaranteed, we’ll do our best to meet your requests. Views vary.

Leavenworth Country Stay

STR #000065 Spring is Here! We are all enjoying the warmer weather and the wildflowers are about to burst-they may have by time you read this! This is a great time to get out walking and soon hiking in the higher country. The birds are so busy, singing and settling down to nesting time. Don't forget Bird Fest in May! Town is still quiet now in early Spring, so it's a great time to visit Leavenworth before schools let out and the many visitors arrive.

Ponderoost - Idyllic Rustic Modern Log Cabin

Charming, cozy, warm log cabin meets comfort, luxury, hygge design, and state of the art amenities! Our cabin has 2 master en suites, an additional bedroom + loft, a great room designed for entertaining, a fully equipped chef’s kitchen, a hot tub, fire pit, and partial river views. Located in the Ponderosa - 5 min from the charming town of Plain, 20 min from Leavenworth & 30 min to Stevens Pass Ski Resort - this family friendly cabin has it all!

Hot Tub, Sauna, Cedar Shower, King Bed and EV

Escape to our stylish 2BR/2BA A-Frame cabin in the Cascade Mountains, comfortably fitting up to 8 guests. This unique retreat features a private hot tub, barrel sauna, and cozy fireplace. Perfectly located near historic Roslyn and the shores of Lake Cle Elum, it's an ideal getaway for families or groups seeking adventure and relaxation. Enjoy modern amenities, stunning scenery, and private beach access for an unforgettable mountain vacation.

Cozy 2-bedroom one mile from downtown Leavenworth

Welcome to our eco-friendly hilltop getaway one mile from the heart of downtown Leavenworth. Our guest house is in a prime location to explore our beautiful town, yet tucked away on a forested hill for that mountain cabin feel. Two bedrooms with new queen beds, a full kitchen, and a lovely walk-in shower. Newly remodeled space. Eco-friendly practices. Wifi. Sleeps 4. No pets please.