Ski-in/Ski-out holiday rentals in Bend

Rustic Cottage with views of the Deschutes River!

Your private riverside cottage awaits! This condo can sleep up to two people in a full size bed, includes a kitchenette and a large bathroom. With the Deschutes directly out the window, you can't get any closer without getting wet! This condo is owned and designed by Bendistillery and Crater Lake Spirits founder, showcasing that local juniper does not only make great gin, it also makes great furniture! Maximum of 2 pets allowed for an additional pet fee of $55.95/pet, requested after booking.

Black Butte Ranch Aspen House

Relax at this peaceful house in Black Butte Ranch Resort. Full kitchen, TV, washer/dryer. Centralized heat and A/C. Wood burning fireplace. Private back deck in the woods. Access to all Ranch resort amenities: golf courses, indoor & outdoor swimming pools, Spa, hot tubs, saunas, gyms, restaurants, bistro, lounge, General Store, horse stables, miles of paved biking & walking paths. Minutes to Hoodoo, Suttle Lake, the Metolius River & the quaint town of Sisters, OR. No pets allowed. No smoking.

Thanksgiving King Deluxe | 15m to Ski

❄️ Winter Wonderland Awaits at 7th Mountain Resort! ❄️ ⛷️ Hit the slopes at Mount Bachelor—only 30 minutes away! 🏔️ Cozy up in luxurious condos with stunning mountain views 💦 Warm up in our saltwater pools & hot tubs after a day of adventure 🍽️ Savor delicious on-site dining & endless fun, year-round 🐾 Service animals welcome—your whole family’s invited! ✨ Need a 1-night stay? Let’s find the perfect deal for both of us! 💰 Mention “Berry Family” for $15 off as a thank-you for reading! 🌟

Ranch Cabin-2pm Check-In & no resort fees-Sleeps 4

Located in Black Butte Ranch, this recently updated 1970s vintage cabin has all the modern comforts of home. Smart TV, WiFi, BBQ Grill and cozy fireplace. This 975sq.ft cabin boasts an efficient and comfortable floor plan. Two bedrooms and one bathroom on the main with 3rd bedroom in semi-private loft upstairs. New appliances and necessary cooking staples in the kitchen. We do our best to keep it stocked with common spices, oils and condiments. 2pm Check-In!! Resort fees Included in my rate!!

Cinder Butte House

This beautiful house is 5 to 7 minutes to the Old Mill District, the city centre, parks, art, cultural attractions, and dining; 20 to 25 minutes to Mt. Bachelor and Cascade Lakes. Guests love the comfortable beds, well-equipped kitchen, the set up, spacious rooms, and the huge back patio with a fire pit, hot tub, numerous tables and chairs, and more. Ideal for families with kids and large groups, the house offers all necessary amenities and plenty of games and toys for both kids and adults.

Chic Sunriver Getaway: Ski, Sauna, Spa, & SHARC

New to AirBnB! Stylish yet private Sunriver home, perfect for outdoor enthusiasts and relaxation seekers! Access nearby river and mountain bike trails, unwind in the private sauna or hot tub, & relax in front of the fireplace. With an open-concept living area, vaulted wood ceilings, and large windows w/ scenic views, this cozy retreat is a perfect blend of comfort and nature. Enjoy all that Sunriver offers, from hiking and biking in summer to skiing in winter. SHARC passes incl.

4-Season RV Camping Trailer

For reservations, please book at slopesidervrentals,com *Trailer NOT at a ready to rent site!* This 4 season camping trailer is set to hit the outdoors 365/24/7 Our cozy retreat takes your camping experience to another level. Take it to the mountains, snow, to a lake or even to the coast. Spend all day outside and find a warm place to stay, right there wherever your journey takes you. Our setup sleeps 8 people but check out our configuration options! Family friendly

7th Mountain 1BR Condo Sleeps 4

This is Central Oregon's premier location for recreation activities. Always wanted to go whitewater rafting? Choose your adventure at WorldMark Bend - Seventh Mountain Resort and mark off some items from your bucket list. Your stay at this Deschutes National Forest resort will have you encircled by peaks, lakes, meadows, culture, adventure, breweries, festivals, family fun and more. With 300 days of annual sunshine and breathtaking mountain landscapes.

Cozy Place: 8 SHARC Pas, Hot Tub, AC, EVL2 Charge

The cozy family vacation home is close to Mt Bachelor, Sno-Parks, Cascades Lakes, High Desert Museum, Lava Butte and Lava River Cave, Newberry National Volcanic Monument, Smith Rock State Park, downtown Bend, Sisters, Redmond and MANY other outdoorsy adventures, this home is close to all of the best Central Oregon spots and has 8 Sharc passes. It has everything you need. Book and Stay as long as you want to!

Lava Bear Lodge--S. of Sunriver

A cozy two bedrooom, one bath home on a fenced acre. The home is a short walk to the Deschutes National Forest and La Pine Sate Park. Cleaning fee and taxes additional.

Rare find cozy clean home

Make some memories at this unique and family-friendly place.

Gorgeous 1BR Condo 7th Mountain Resort!

Reconnect with loved ones in this family-friendly place.