Holiday rentals with outdoor seating in Damascus

Charming one bedroom apartment in the forest.

This unique apartment above a garage/shop , detached from the main house. Tucked away into a urban forest. I call it Our Robin's Nest because you look out on to branches of large fir trees. It is very private , yet Starbucks is right next door. Private entry and off street parking. This space has everything you need full kitchen, washer&dryer, queen size bed and fold out couch , plus a Play and Pack for the Littles. Walkable neighborhood , parks market and restaurants within walking distance.

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!!

Peaceful Spacious Single Level Home

Look no further if you are looking for a clean & spacious home with all the amenities for a comfortable stay. Single level with a walk in ADA shower in the primary bathroom. Dedicated office/den with excellent wifi. Remote work & family friendly. 5 minutes away from the Clackamas mall, Costco warehouse/gas, Target, REI, restaurants, Kaiser hospital. Clackamas is a suburb of Portland, only 25 min. drive of downtown and airport. *Co-hosts conveniently live nearby to assist whenever needed

Sweet Private Suite in Historic Home

Mary and I love hosting people who appreciate a comfortable experience and beautiful space. Our Private Suite is located in an idyllic setting central to all the activities, great food and nature that the greater Portland area is known for, but without the "junk" that comes with being in the city. Short drives to Portland, Mt Hood hiking and skiing, the Columbia River, Multnomah Falls and great entertainment at McMenamin's "Edgefield (15 Min)" and "Grand Lodge" (35 min.). Infants 0-2 welcome.

Mid Century Villa w/Mountain View & Movie Theater

Just relisted as we had long-term renters due to total fire loss. 3400 sq ft hillside retreat decked out with rare furnishings. Take in the Cascade Mountains from the wraparound deck and lounge under giant maple trees. You'll love the 125” Hi-Def movie theater (w/ 200+ movies)! Two large primary suites with king bed and large showers. One additional queen bedroom and one large office. Close to urban and nature, 20min to the airport, with daytrip opportunities to all the PNW must-see spots.

Idyllic Countryside Getaway at Wilson Farm Cottage

Nestled in a rural valley a short commute to mountain skiing, fishing or downtown nightlife, Wilson Farm is 8 acres of paradise. Be transported to a simpler time and enjoy our beautiful guesthouse with old world charm. Relax in the stone cabin or the viking house or explore trails in our woods. An abundance of nature awaits! Farm fresh breakfast fixings are included. Intimate weddings/events are also welcome and we have some prime weekends blocked for this. Please inquire if interested.

Tiny Private Studio near Sandy, Oregon

Located between Mt. Hood and the Columbia Gorge! Cozy private studio, with a separate entrance on 2 quiet acres. This small studio has a comfortable queen bed with luxury linens throughout. A tiny kitchenette supplied with coffee, organic half and half, an assortment of tea, bottled water, and a few snacks. Wifi and YouTubeTV provided. Grocery stores, restaurants, movie theater, gym, and hiking trails just to name a few amenities all within 1 to 3 miles of our home.

Romantic ‘Glamping’ Farm Tiny Cottage

Glamping at its finest! This adorable, warm and cozy, artistic, and truly unique storybook cabin is nestled in a quiet, close-in farm setting (but only 30 min to DT PDX). You’ll love the magical vibe, artwork, decor, lighting, coffee bar, comfy bed, cute outhouse w/cold water sink, and a private outdoor heated shower! We welcome ALL colors, LGBTQ, and outdoor tobacco friendly. Cannabis flower allowed indoors in separate, fun and funky TV/game shed. You'll LOVE it here!

Light Filled Garden Studio

Our wonderfully bright garden studio is perfect for a short stay or for visitors looking to explore Portland for an extended visit. It has a full, well-stocked kitchen, ideal for those looking to stay in and cook, but it’s also just a 20 minute drive from downtown, for those looking to explore the wonderful restaurant scene Portland offers. Keyless entry and private entrance through the side yard gate provide renters with complete autonomy during their visit.

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!

Foxglove Farm Private Guest Suite

Enjoy a stay in a ground level suite in our two acre country home. Experience the privacy and quiet of the countryside, yet shopping and restaurants are just moments away. We are 30 minutes from PDX and downtown Portland, less than an hour from Mt. Hood and the beautiful Columbia River Gorge, and 90 minutes from the Oregon Coast. You will have your own private entrance, and have access to a porch and deck with scenic views.

Quaint Tiny House In The Trees. Damascus, Oregon.

150 ft. walk down a steep driveway takes you to a unique private little studio with everything an adventurous spirit needs. You must be in physically good shape to handle this location. We have friendly dogs you may see outside. 30 min. to SE Portland, 45 to PDX, One hour to Mt. Hood, 40 min to waterfalls in the Columbia Gorge. Pool open June 15 through September 5th. Can accommodate a 3pm check-in all days except Tuesdays.