Family-friendly vacation rentals in Damascus

Unique Underground Speakeasy with hot tub

Escape the city in this unique underground stay. Located just outside the city and a quick drive to Mt. Hood. You are sure to leave relaxed and recharged after being surrounded by nature. Soak in your own private hot tub overlooking a forested ravine. The underground space is climate controlled equipped with AC/heat. Connect with nature while you enjoy the massive covered patio with a bbq and games. Ask the owners to hangout with the friendliest Pygmy goats and take photos to cherish the memory.

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!!

Artistic Boho Romantic Woodshed

This warm and cozy close-in country sanctuary is like nothing you've EVER seen! If you like affordable ultimate glamping, then look no further! The fire pit, creative décor, heat pump, table/chairs, weekly serviced private portapotty (equals most of cleaning fee), sink, HD TV, WiFi, Alexa, outdoor covered heated shower w/view, AND 2 friendly Scottish Highland cows you can feed and interact with! We welcome ALL colors, religions, LGBTQ , Cannabis friendly! Cigs OK by fire pit only.

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. We have friendly dogs you may see outside, and we do not allow pets. No smoking in the unit. There is a smoking hut on the property you are free to use should you choose to (bring a container with you to dispose the remnants). SE Portland is a 30 min drive and downtown Portland a 45 min drive. One hour to Mt. Hood, & falls in the Gorge. Pool open 6/15 through 9/5.

Cheerful 2 bedroom cabin on the Clackamas River

Take it easy at this unique and tranquil getaway. Nested on a bluff with sweeping territorial views bordered by the Clackamas River, this 2 bedroom home sits on an acre of property just outside of Portland. It has been completely updated with a new gourmet kitchen, spa-like bathroom, master with a private balcony, dedicated work space, and a huge deck to enjoy all that nature has to offer. The upper yard is fully fenced for your pup and there is private walking path to the river.

Arched Cabin with sauna on the Sandy River

Welcome to our stunning two-bedroom, two-bath arched cabin nestled along the Sandy River. Enjoy direct access to the river, where you can bask in the natural beauty of the surroundings and a view of Mt. Hood. The open concept living area boasts large windows that frame the breathtaking river views, creating an inviting ambiance that's perfect for relaxing. Indulge in a the barrel sauna with panoramic river vista. The cabin is close to endless activities up and around Mt. Hood.

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

Oasis Between City, River & Mountain. Damascus OR

A large & private guest house on lower level of home only 30 min. to Portland. Mt. Hood, Gorge Waterfalls & Scenic hikes within 60 min drive. Super comfortable bed, quiet nights, recliner sofa & relaxing atmosphere make this an ideal place to hang out and rest. We welcome ALL colors, LGBTQ. Must Read all info, house rules & details prior to booking please. Informed guests are happy guests. Can accommodate 3pm check in every day of the week except Tuesdays.

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!

Breathtaking views, Fish, Ski, Mt. Bike, or Hike

Experience a charming two-bedroom suite in the daylight basement of a two-story home, complete with a private entrance and covered patio. Enjoy breathtaking views of Mt. Hood and the Sandy River from your beautiful backyard. Nestled near Oxbow Park, you're just minutes from shops, restaurants, and outdoor adventures in the Columbia River Gorge and beyond. With the Portland airport only 25 minutes away, this cozy retreat is the perfect getaway!

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.

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.