Holiday rentals with outdoor seating in Deschutes River Woods

Quail View-Pets Welcome, Great Outdoor Space

Quiet tree lined cul-de-sac location this executive master suite has all the comforts of home. Kitchen has dishwasher, gas range & large refrigerator. Private patio surrounded by gardens & paver walkways, access to shared deck with gas grill. Big screen TV for relaxing & desk for working. Expansive bathroom with dual sinks, walkin shower, heated towel rack & heated tile floor. Extra Large Closet includes washer/dryer & also has heated tile floors. Private entrance & separate off street parking.

Private Apartment, Separate Entrance, Spacious

DCCA License #001537 Welcome to the Garden Sweet, a private apartment adjacent to a residential home. Tuscan style living nestled on a beautiful acre. Private and peaceful, yet just minutes to great local dining, shopping and outdoor recreation. The historic downtown and river are an easy 6 minute drive into the heart of old Bend. Spacious 3 room suite-living makes longer stays comfy! No shared interior spaces. Our extensive gardens, gazebos, grills, firepits are shared and open for guest use!

Home in Lodges at Bachelor View - Book Now!

Enjoy Bend’s newest west-side neighborhood nestled beside Century Drive, the gateway to Mt. Bachelor and the Cascade Lakes. Our unique location puts you right on the connector trails to the popular Phil's Trail System for mountain biking or casually strolling along the Deschutes river trail. With access to the National Forest in just steps and breweries mere minutes down the road, Pinehaven is as 'Bend' as it gets. Thank you for considering Pinehaven for your stay. We think you’ll love it here!

Forested Artistic Cozy Tiny House w/ Wildlife

This tiny house is quaint and cozy but has all the trappings of a modern home. It has a full size kitchen, bath, dining area, work station, TV loft, and bedroom. We built the house and the surrounding area with the sole purpose in mind to create a perfect, comfortable, memorable getaway in nature. What makes our rental truly unique is the wildlife that roams our property. In the yard you can expect to see deer, birds, squirrels, rabbits, and chipmunks. We are close to town yet away from it all.

Chalet del Sol - Hot Tub - Ping Pong - Fire pit

Welcome to the cozy Chalet del Sol just South of Old Mill District and close to the hiking trails. What this home offers: ☞ Entire property to yourself ☞ Hot tub ☞ BBQ & Blackstone ☞ Ping Pong Table ☞ Master w/king bed upstairs ☞2nd bedroom downstairs queen bed ☞3rd bedroom is a loft w/queen & 2 twins ☞Two full bathrooms ☞ Fast WIFI ☞ Garage ☞ Fully equipped chef’s kitchen ☞ 65” Smart TV w/ Netflix ☞ Lots of Parking → 4 plus cars ☞ Private yard ☞ Washer + dryer ☞ Ductless heating and cooling

Cozy Studio! Walk to NW Crossing and Shevlin Park

Cozy, soft decor fill this light, bright studio with a private entrance. Shevlin Park and Phil's Trail are minutes away for hiking, running, and mountain biking. Mt. Bachelor is a short 30 minute drive for skiing in the winter and downhill biking in the summer. Smith Rock is a 45 minute drive for hiking and climbing enthusiasts. Shopping and dining are within walking distance at NW Crossing or a a short drive to the Old Mill or Downtown Bend. Mesh Network Wifi, coffee, tea and snacks provided.

Midtown Getaway- Private entrance and bathroom!

Just over 2 miles from downtown. This is a private room attached to our house with a separate entrance. The room has a double bed, full private bathroom, closet space, a kitchenette, and seasonal access to the outside deck and hammock. Includes heating and cooling controls, a mini-fridge/freezer, microwave, coffee maker, cups, plates, and utensils. Coffee, tea, snacks, ice provided. Great for late night arrivals or early departures! The space is quaint- room & bathroom- 185 sq. ft. total

Welcome to Dome Sweet Dome

Your chance to stay in a true-to-name Geodesic Dome! This one-of-a-kind retreat blends comfort with architectural charm. Guests call it cozy, inspiring, and unforgettable — a stay that feels like an experience, not just a place to sleep. Nestled in the First-on-the-Hill neighborhood off Century Drive, the Dome is perfectly positioned for everything Bend has to offer. Whether you’re here for skiing, biking, hiking, or just relaxing, you’ll love how close you are to Bend’s best adventures.

Mountain Bliss: Gateway to Mt. Bachelor and More

When the mountains are calling, Bend is like nothing on earth. Savor the charms of Base Camp throughout the year in this luxurious and spacious cabin (1200 square feet). Celebrate the great outdoors – best experienced through unparalleled adventures at Mt. Bachelor (18 miles), Phil’s trailhead (15 minutes), the Deschutes River (5 minutes) as well as the endless access to hiking, biking, running trails, skiing, golf, breweries, restaurants, coffee shops, and the Hayden Homes Amphitheater.

Peaceful Ponderosas | Only 10min from the Old Mill

This Bend, Oregon home is the perfect getaway. It sleeps six and spoils you with king beds, high end appliances, spa-like amenities, a hot tub and other outdoor spaces you can retreat to. The modern environment is stocked with all the comforts you'd find at home such as a fully stocked kitchen, books, games, WiFi, desk-space and a 65 inch streaming TV. The open floor plan with two couches is perfect for lounging around on a lazy day or gathering together for some time by the fire.

Airy Bend Oasis - Two Ensuites

Cheers to your stay at Bent Pine Oasis, located in the picturesque west side of Bend! This home provides the ideal location for any outdoor enthusiast: Mt Bachelor's slopes are just a 20 minute drive & the Deschutes River Trail is mere steps from the front door- your avenue to biking, running and exploring Bend. Looking for a more relaxing day? You can make the 5 minute drive into the Old Mill District to enjoy food trucks, a river float, or fresh hops at a local brewery.

Sunriver Studio with Pool and Hot Tub

This stylish studio in the heart of Sunriver is newly remodeled with a King bed. Seasonal pool and year round Hot Tub! Just a short walk to a brand new food truck lot with 7 trucks, indoor and outdoor seating and a bar. Fast WiFi, a new Samsung 50” tv signed into Netflix, Hulu, HBO Max and more. 25 minutes to Mt. Bachelor. 25 minutes to downtown Bend. Parking is just a few feet from your door. This super clean condo is perfect for all of your central Oregon adventures.