Guesthouse holiday rentals in Clackamas River

Oswego Empty Nest

The Oswego Empty Nest is a newly remodeled, cozy, one bedroom unit located in Lake Oswego with a private entrance and 500 sq ft of living space. Prepare your own meals in the beautiful full kitchen. Relax, work or entertain yourself in the living space with a large TV with Roku or rest in the quiet comfortable bedroom with an en suite bathroom. Easy access to restaurants, New Seasons, Columbia Outlet, and hiking trails all within walking distance. Close to downtown and quick airport access.

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!!

Private urban retreat, new build, 1bedroom, sleep4

Relax in this calm, clean and simple space. Enter in from the sidewalk fence to a little patio great for enjoying your coffee and some fresh air. There is a full kitchen that opens into the living area with a skylight and high windows that offer great natural light. Walk down the hall and enjoy the spacious bathroom with our provided bath tray for real relaxation. Tuck yourself into bed and enjoy the stars or choose to black out windows using our automated shades for uninterrupted sleep.

Secluded Willamette River Apartment in Lake Oswego

Enjoy a private stay full of nature with a river view! Newly remodeled 1 bedroom private apartment secluded and quiet. Apt is completely separate from main house. 10 min wlk to Mary's Woods Ret. Comm, 20 mins to George Rogers Park, 10 more to DT Lake Oswego w/shops, restaurants and theaters. Private, wooded property along the Willamette River. Fully rmld kit. & BR, LR with large 50” Smart TV, fast wifi. Q-bed + twin in sunroom, table/work area + wa/dr below. 8 stair entrance at back.

The River House - Waterfront Retreat w/Fireplace

Experience the serenity of riverside living in our private, enchanting retreat nestled on the tranquil banks of the Clackamas River. This guest suite offers 1500 square feet of living space, boasting a private entrance and a spacious deck that grants breathtaking views of both the serene pond and the majestic river. Step inside to discover a haven of comfort and elegance. The gourmet kitchen features SS appliances, sleek granite countertops, and is fully stocked for your culinary needs.

Oscar's Perch - Fantastic & Private 1-BR

Private one-bedroom in NE Portland with a full kitchen, roomy bath with W&D, wi-fi, & parking. Bedroom has a queen bed; sofa converts to a queen bed. USB ports in kitchen & bedroom. Golf course, park, bike route, public trans., restaurants, wine shop, brewery, & grocery store all within several blocks. Easy access to downtown and PDX. 5% of the nightly rate will be donated to Gales Creek Camp for Kids with Type 1 Diabetes. We welcome and appreciate the diversity of our guests!

Bright, Private & Cozy with Yard

Relax in this private, bright and cozy studio space with fully fenced back yard. Nestle up by the outdoor fire, or enjoy a sunset under the covered patio. Equipped with TV, WiFi, and FireStick so you can connect to your favorite shows easily. Kitchen has microwave, mini-refrigerator, induction stove, dishwasher, and all of the supplies you would expect! Enjoy cozy Brooklinen bedding (it's the best!). Full bathroom with washer/dryer, walk-in shower, and ultra soft bath towels!

Boring Bungalow /1 bedroom guesthouse with kitchen

Private and quaint one bedroom one bathroom guest house in beautiful Boring Oregon. Centrally located between beautiful Mt Hood recreation area, breathtaking Columbia River Gorge and the stunning Oregon Coast. You have a private entrance with keyless entry, a comfortable living area and well appointed kitchen. Free on site parking with room for boat and trailer if needed. All linens are provided, as well as a starter supply of toiletries, coffee and tea. STR784-22

SE Portland Guest Cottage

The guest cottage offers self check-in. It is located in a quiet neighborhood in SE Portland. High ceilings make this studio airy and bright. We think of it as a perfect hotel room without the hotel. The small galley kitchen has everything you need to cook a gourmet meal including filtered water. There is a full bathroom with tub and shower. The cottage stands on its own making it perfect for coming and going as you please. City of Portland Permit #24 013532

Sandy Sanctuary

Ready for a break? Want a cozy getaway, closer to recreation? Sandy Sanctuary is your spot! Surrounded by evergreens on the outside, and filled with delightful offerings on the inside: puzzles, books, a fireplace and premium linens. Whether you're a weekend warrior, or just want a break from the grind, we think you'll find this a blissful place to rest your head. Located on the edge of Sandy, it's walkable to food carts, coffee, and stunning trails!

Garden Home Getaway

Welcome to the Garden Home Getaway, your serene retreat in the heart of Portland's Southwest Hills. Our space is designed for luxurious rest and relaxation, while still providing all of the functional and practical comforts of home. An ideal environment for couples and small families to make memories and have the perfect home base for adventurous excursions. We're here to help you curate your stay and find your own slice of Portland.

River Forest Guest House, River and Dock access

Tasteful and brand new guest house, beautiful neighborhood on the river. Guests have private deck facing yard and separate outdoor sitting area on the Willamette river (behind main house). Watch the birds, boats and riverboat cruise from the patio with fire pit. 2 miles from lightrail station, restaurants and shopping nearby and 15 mins. to downtown Portland. All are welcome! We are on the east side of the river, Milwaukie area.