Holiday rentals in Winthrop

4.96 out of 5 average rating, 263 reviews

Romantic Boutique Getaway with cozy fireplace.

Top floor unit, no one above you! This newly remodeled private boutique-style condo with central AC is the perfect getaway for 1-4 guests. Located next to Lakeside Park, near the heart of Chelan. Includes free parking, fast WiFi, a community pool and sauna, and thoughtfully stocked kitchen and bathroom. Centrally located, just seconds from the lake, with quick access to vineyards, golf, fishing, water sports, hiking, shopping, and more! Need only 1 night? Send me a message for availability.

4.8 out of 5 average rating, 30 reviews

Home in Manson

Kid Friendly Lake House with Incredible Views!

This property sits atop the quiet Summerset at North Shore Neighborhood with almost 360 degree views. Every bedroom has views! Enjoy coffee or cocktails on the large 350+sqft deck and soak in the views with outdoor speakers. Or soak in your own private hot tub that's basically a small pool. Send the kids downstairs to their own oasis - 2 sets of bunk beds and cabinets filled with toys, games, and movies. Booster seats, high chair, a crib, and pack n play are there, so pack light! STR 000741

4.83 out of 5 average rating, 12 reviews

Home in Chelan

Sunny Retreat-Lake views/HotTub/BBQ/firepit

Welcome to Sunny Retreat recently renovated downtown cozy retreat nestled in the heart of Lake Chelan, just 3 minutes from downtown and lake access! This charming cabin-style home offers a perfect getaway for families and friends, stunning lake views and a range of amenities designed to make your stay comfortable, relaxing, and fun. As you step inside, you’ll be greeted by the unique cabin-style living room, cozy furnishings, and large windows that frame the breathtaking views of Lake Chelan.

5 out of 5 average rating, 4 reviews

Home in Chelan

The Boho Beachhouse Lake Chelan

Experience the picturesque ambiance of Chelan, WA, by staying in this Lakefront 3BR 3.5 Bath getaway offering a perfect escape from the everyday hustle and bustle. It promises a relaxing retreat with breathtaking views, close to the town's attractions, wineries, and natural landmarks. ✔ 3 Comfortable Bedrooms with Attached Bathrooms ✔ Open Design Living ✔ Fully Equipped Kitchen ✔Spacious Deck (Dining, Fire Pit, BBQ) & Fully Fenced ✔ Smart TVs ✔ Game Room ✔ High-Speed Wi-Fi ✔ Dock & Boat Lift

Top guest favourite

Cabin in Winthrop

4.99 out of 5 average rating, 263 reviews

Skytop: Breathtaking views and easy walk into town

Whatever the season, Skytop is the ideal base for your Methow Valley adventures. This rustically modern, wheelchair-friendly cottage feels remote, yet downtown Winthrop is a mere quarter-mile away. The new second-story Treehouse Suite (which rents for an additional $100 a night paid directly to the owner) features a gas fireplace and freestanding tub, allowing a second couple or generation to enjoy their privacy while sharing Skytop's kitchen, dining and entertainment space. (Sorry, no pets.)

4.91 out of 5 average rating, 124 reviews

Waterfront Studio Condo on Lake Chelan

You can't beat this WATERFRONT location with great amenities, and private condo-living a short walk to downtown Chelan! Features include: - Large sandy beach, grassy areas, beautiful landscaping, picnic areas - Year-round heated adult hot tub. - Seasonal: heated pool, charcoal BBQ's, picnic tables, lawn furniture, cabana - Onsite coin-operated laundry, children's playground, large dock, pickle ball court, and free parking City of Chelan Short Term Rental License: #STR-0004

Top guest favourite

Cabin in Leavenworth

4.99 out of 5 average rating, 101 reviews

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!

4.77 out of 5 average rating, 141 reviews

Top floor 2BR condo w pool & hot tub open all year

Most desirable top floor, lakefront condo at Chelan Resort Suites. Conveniently located next to Lakeside Park & Beach where you can enjoy water activities and sunbathing by day or take a walk or short drive to various local wineries, golf courses, restaurants, shops, Slide Waters and more! At night, soak up the beautiful sunset & gorgeous views of Lake Chelan from your private patio.

4.95 out of 5 average rating, 63 reviews

Cabin in Leavenworth

Rustic Neighborhood Lodge #1596

The lodge is situated on 3 wooded acres in a quaint forested neighborhood with over 5,000 square feet and 10 well-appointed bedrooms that can easily accommodate 12 of you and your family and friends. Due to Chelan County regulations, please note that we will not allow more than 12 guests, including infants. Thank you for respecting our neighborhood!

4.87 out of 5 average rating, 104 reviews

Apartment in Manson

Luxury Condo / Incredible Views Pool / Spas

Pristine views of Lake Chelan, walking distance to downtown Manson which offers the local brewery, an array of wineries and restaurants. Across the street from the public swimming area Manson Bay Marina with boat docks and boat rentals. Luxury all the way! This unit is on the second floor.

4.72 out of 5 average rating, 162 reviews

Fully Remodeled, Pool, Park, Lakefront Fun

"Lakeside Paradise: Fully Stocked Condo, Heated Pool, and Endless Family Fun! Experience the Best of Chelan, Just Steps Away from Lakefront Park. Close to Town, Waterslides, Wineries, and Golf Courses. Perfect for Couples or Families of 4-6. Book Now for a Relaxing Getaway!" Chelan STR-0355