Guesthouse holiday rentals in Cascade Range

The Greenwood Villa w/wood fire hot tub

The guest house, we affectionately call the Villa, is situated near great views, restaurants, wineries, and nature trails available in Jacksonville, Ashland and Medford. Located in the country with views of the famous pear orchards. We have designed the Villa to be a quiet retreat that offers some unique features, so please familiarize yourself with our Property and House Rules. Every detail invites you to slow down and enjoy the beauty of Southern Oregon. Find us on socials: @thegreenwoodvilla

The Trail House (Private Sauna & Rain Shower)

The Trail House is the perfect escape — a modern cabin set on the edge of a private forest, overlooking the ocean. The Trail House is more than just your home base to explore, it's an invitation to create space from your everyday life & reconnect with nature. Relax in your own private sauna, unwind by the propane fire pit & soak in the views. Just minutes from Bowen Island’s best beaches & hiking trails, this newly finished suite offers a calming retreat with a thoughtfully curated interior.

Columbia River Eagle’s Nest Guest House

Sitting at 1500 feet above the valley is perched a quiet, and peaceful sanctuary. Epic view of the Columbia River Valley with Mount Hood and the City of Portland in the background. Venture to visit downtown Kalama, the river beach, shopping, food. Near by Mount St Helens area is right behind you. 45 minutes from Vancouver and Portland areas. This private apartment is completely separated from the owners house. Enjoy mountain living with still being close to I-5 corridor for recreation.

Moore's Camano Cottage, Home with a View & beach

Set between Whidbey Island and Washington's mainland, beautiful Camano Island can be reached by car. With over 56 miles of beaches, boating, salmon fishing, clamming and crabbing are bountiful. The unique appeal of Camano Island is that it offers visitors a real-life island experience, including a strong arts scene. Recreational activities such as biking are popular here. The island is also home to Camano Island State Park, which boasts 173 acres prime for camping, hiking and bird watching.

Whidbey Island Modern Cottage

Recently constructed modern cottage nestled in the stunning beauty of Greenbank on Whidbey Island. Come enjoy a slice of sanctuary and get away from the hustle and bustle of the daily grind. Centrally located between charming beach towns, breathtaking hikes, and delicious dining. Cottage offers a 3/4 bath, a kitchenette, and an open space with a king size bed. Equipped tastefully and thoughtfully with custom built features. Come enjoy the spirit and vibes quaint island living has to offer.

The Haseman House

Come stay in our Architectural micro home in NE Portland. Close to Mississippi and everything that NE Williams has to offer. Thoughtfully deigned with many amenities. A great WFH vacation retreat. This little house is located in the back of a main house. The backyard is shared with the main front house. There is only street parking but it is free and typically available. We are close to public transportation and rental bikes as well as an organic grocery store... very walkable.

Willamette Valley Luxury Chateau

Escape! Voted as one of the Salem’s luxurious places to stay. Treat yourself to “Ritz Salem” This will likely be one of the best Airbnb experience. This place is quiet and relaxing, as you enjoy the views, nature, and time alone. Great place to celebrate your birthday or anniversary with a quiet retreat, wine tasting, or visit nearby restaurants or nature. It offers king size bed, gas fireplace, large space, full couch, high ceilings, and fast internet. No contact self-check in.

The Overlook House with amazing view!

We chose to share our guesthouse primarily because the idea of sharing our stunning view appeals to us very much. We are so fortunate to have a view so special that we wanted to build a guesthouse for our friends and you! We designed our 600 square foot modern guesthouse with the intent of creating a very private honeymoon suite. It has expansive views of Hood River, Mt Hood, and our favorite view, looking directly down the gorge.

Romantic Getaway, Hot Tub, Ski-in/out

Exceptionally decorated and furnished log home in a ski-in-ski-out location. Home is a duplex with your own private entrance. Hot tub is exclusive to you, our AirBnb Guest and not shared. Garage equipped for guests to securely store bikes and skis. Private covered walkway that puts you right on the Summit West slopes. Connected to Summit Central and East. Walkable neighborhood with restaurants. Dog friendly. 500Mbs Up/Down WiFi.

Charming 1 bedroom loft/barn apt with hot tub

Take it easy at this unique and tranquil getaway! Nestled in the heart of the Willamette Valley, this peaceful loft is perfect for the couple looking to relax and recharge. Enjoy our local farmers markets, or a baseball game at Volcanoes Stadium. Tour our local restaurants and wineries or see what’s happening this summer with our local music scene. Visit our many hikes and trails or float our rivers and lakes - and on and on!

Indoor Swimming Pool-Heated & Private

Includes the whole bottom half of this home with it's own private entrance, indoor heated pool, home theatre, full bathroom plus half bathroom, laundry room, master bedroom with queen bed, and three fold our twin beds. When you will pull up to this property, you will be surrounded by a vineyard and completely immersed with beautiful mature landscaping with thousands of flowers.

Muse Cabin in old growth forest w/cedar hot tub

Enjoy our beautiful cozy cabin that is heated exclusively by a wood stove, on the edge of a magical old growth cedar forest on our 11 acre farm and vineyard. Relax on the deck built into the trees, and sleep peacefully in the loft bed, as you soak in the nature around you. The cute out house is just down the path and the cedar hot tub/ outdoor shower is next to the garden.