Guesthouse vacation 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

Waterfront Cottage with Eagles & Highland Cows

Escape to our WATERFRONT farm just outside of Langley on beautiful Whidbey Island with Eagles & Highland Cows. Our family has lived here since 1890, and we have a wonderful guest cottage sitting on the high bank with 180-degree views of Saratoga Passage, Mount Baker, and the North Cascades. With 900 square feet of open living area, a fireplace, full kitchen, washer/dryer, king size bed, high speed internet, 2 TV's, beautiful furnishings and easy access to the beach it's the perfect get-away!

Luxurious Riverfront GuestHouse, Sauna & HotTub.

Welcome to our Clackamas Riverfront Guest House—a peaceful riverside retreat blending rustic charm and modern comfort. Relax in your private hot tub and sauna, unwind by the fireplace, and enjoy stunning river views. Fish, kayak, or raft right from the backyard. Bedrooms include white noise machines and earplugs to help with normal traffic during commute hours on our scenic road. The guesthouse is attached but its own private unit with its own separate entrance and parking. Enjoy your stay!!

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.

Accessible, AIA-Award Winning, Urban Garden Oasis

A nurturing place with abundant light, garden views, & access to the best Portland food. “The best Airbnb I’ve ever stayed in!” - frequent guest comment. - American Institute of Architects Award to designer Webster Wilson - Upscale amenities & European fixtures - Quiet NoPo neighborhood tree-lined street, minutes from downtown - Fully equipped kitchen w/ fresh local coffee - Indoor & outdoor dining - See photo captions for more details - Trained Service Animals welcome; no pets nor ESAs

Luxury Guesthouse Retreat w/ Hot tub, Sauna, Views

Private luxury guesthouse retreat at 1,800' elevation. Enjoy the healing benefits of a hot tub with amazing views of Mt Hood, Mt Jefferson, and the Columbia River. Relax in an infrared sauna or a hammock on a covered porch while nature surrounds you. Thoughtful interior spaces and amenities to make your stay as comfortable as possible. 100MB Fiber WiFi, EV Charger. A great base camp for easy day trips to Mt St. Helens, Mt Rainer, Mt Hood, Astoria, ocean beaches and the Columbia River Gorge.

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.

Spoil yourself! Luxury Cabin on the Santiam River

Escape to our Luxury Cabin Suite, designed just for two adults, located right on the beautiful Santiam River—only 20 minutes from Salem! Whether you’re looking for a peaceful place to relax, a romantic getaway, or simply a spot to unwind, you’ll find it here… and best of all, no dishes to wash! Love the outdoors? Bring your hiking boots, fishing gear, kayak, or raft and make the most of the surroundings. Please note: Our cabin features one bed and is not suitable or equipped for children.

Spectacular Beach & View: The Loft

Wake up to spectacular views of Puget Sound and Mt. Rainier from this 700 sf, 2-story, chic and comfortable cottage on a 40 acre waterfront estate property. The southern exposure beach ( 1000ft of private beach) is the ideal for strolling, beach combing, and relaxing. A fire pit, propane bbq, hammocks, and lounge chairs awaits for outdoor r & r. Trails through the forest for hiking. Mountain bike trails at Dockton Pk..Your pet is welcome, leashed, with an additional pet fee.

The Bear's Den, studio with kitchen and pond/creek

Our wonderful guest house is a cozy studio with a queen bed, kitchen, sofa, and dining table in one large room. There is a bathroom with shower. This is a second floor apartment over the detached garage, we live in the main house next door. The property is very secluded well off the road with no other houses nearby and borders the National Forest. Enjoy the spring fed pond in the front yard, a hike along the Sandy river, or a 15 min drive to ski resorts.

Orcas Island Sunset Retreat

Relax on Orcas Island in this quiet and peaceful guesthouse high up on Buck Mountain. Enjoy gorgeous views and spectacular sunsets, south to Olympic Mtns and west to Vancouver Is. This 900 sq ft guesthouse has a rustic elegance and is comfortably furnished. Ten foot high ceilings add to the grand and spacious feeling of the guesthouse. Hand waxed pine plank floors and dark woodwork give a lustrous sense and air of old and timeless beauty.

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.