Holiday rentals with outdoor seating in Gladstone

My Cozy Place- For the Budget Traveler-29 day max!

This cozy unit is a converted rec room located on the bottom floor of a two story house that includes a living room, a separate bedroom, a bathroom with shower, and a small kitchenette /laundry room (cold water). The kitchenette includes a microwave, toaster oven, hot plate, coffee pot, utensils, and refrigerator. The unit can be locked with key. STEPS are required for entry. Not recommended for guests with mobility issues. Extra guests are each charged $5 per day. NO smoking/vape inside.

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.

Forested Hygge House Getaway

Relax in a Gladstone oasis overlooking an untouched trail and forested area. A cozy, bright, and private spot. I hope you connect with my affinity for vintage art and clean lines! You’ll have the entire house and 1/3 acre to yourself. Less than 30 mins from most anywhere in Portland Metro, 10 mins to Oregon City, and 1 hr to Mt. Hood. This is a dog friendly (no cats), non-smoking house. The large yard is on a dead-end street, though not fenced. *Not ideal for those with mobility issues*

River Garden Cottage.

Charming cottage apartment on a garden and forest hill. Next to the Willamette River, 30 mins from downtown Portland. Relax, and enjoy the quiet and peaceful surroundings. Fully stocked kitchen. Fast wifi at 50 Mbps. Cozy inside in the wintertime, also with a park-like setting with walking access down the lush backyard to the river where you can enjoy swimming, fishing, kayaking, and bird watching. You can use the shared recreation room with ping pong, pool table, shuffleboard, and weights.

Gladstone Garden Retreat

Lovely updated bungalow, private & quiet garden retreat in old Gladstone home, walking distance to Clackamas River. Gated yard with garden, grill, outdoor dining, east facing windows, private keyless entrance, off street parking. Tons of natural light; beautifully decorated; AC, HDTV, Wi-Fi, Cable TV with movie channels; Queen beds; designer appliances for gourmet meals; rock fireplace w/ gas, soaking tub upstairs, updated shower downstairs; washer & dryer. Pet friendly patio w/ doggie door.

Crossroads Country Cottage

Conveniently located at the crossroads of HWY 224 and SE Lake Road, our home, cottage and garden are the last remnants of a time gone by and what was once a large family farm. When you walk through the private gate leading to the cottage, you might feel you have stepped through a portal into another time. Everything about the cottage is secluded, peaceful and private. We are pleased to have many return visitors. The garden features a waterfall, chairs and table, BBQ and fresh herbs.

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.

The Wee Humble Cottage

Cozy 1 bed, 1 bath, 100 yr old smoke/vape free cottage is conveniently located in Gladstone, OR; walking distance to local shops & antique mercantile. Within blocks of the confluence the Clackamas & Willamette Rivers. Just 1.5 mi from historic downtown Oregon City Main Street, Willamette Falls, Abernethy Center & End of the Oregon Trail Museum. Also conveniently located near the Trolley Trail Loop, a 19 mile long meandering walking/cycling trail through a series of quiet communities.

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.

Rustic Creekside Cabin

This tranquil hideaway feels like you're in the middle of the forest, but is just minutes from Portland. Relax next to the burbling creek surrounded by towering cedar trees. The MAX Orange line and downtown Milwaukie are only five minutes away. Built in 1928, the cabin has one bedroom and bathroom, living room, full kitchen and central heat. The bedroom has one queen bed and an en suite bathroom. There is a pull-out queen futon in the living room.

Sunlit Oasis

This private, renovated art studio has skylights and quiet views of nature. As an interior designer, I loved creating a space that is as much an experience as a night away from home...and only 10 miles from downtown Portland! Please be advised that beginning Dec19, 2025, construction has begun on three homes behind our cottage. Work can begin at 7:00AM-7:00PM Mon-Fri. There could be noise during those hours, it's out of our control.

Tiny Sequoia House

Feel refreshed when you stay in this rustic gem. With a full heated outdoor yet private shower, lofted queen bed and fold-out couch, walking distance to tons of restaurants and shops, 15 - 25 minutes into Portland proper depending on where you're going and very close to the wilderness and hiking.