Holiday rentals with outdoor seating in The Dalles

Super cozy apartment walking distance to downtown

This apartment is located on the second floor and is one of three Airbnbs offered. The main room is spacious with a luxurious queen bed, dining table/chairs and a 55” smart tv. The kitchen is nicely equipped for meal prep or a cup of coffee, tea or cocoa. The pantry is nicely furnished. Our garden is open for enjoyment with lodge pole rocking chairs, fire pit and table for outdoor dining. Our apartments at Https://www.airbnb.com/h/wellesmanorgarden and Https://www.airbnb.com/h/wellesmanorfamily.

Creek-side Retreat - Glamping

Experience year-round glamping at our Oregon retreat! Nestled on a serene creek, our cozy (and very private) tent area harmonizes comfort with nature. Explore forest trails and a creek, relax by the fire-pit, and wake up to alpacas, goats, ducks, and chickens amid scenic views. With a rustic barn, outdoor kitchen retreat, private bathroom (real flushing toilet), tub and invigorating outdoor shower, it's the ultimate escape, just 90 minutes from Portland. Book now for an unforgettable experience!

Twin Oaks House, Scenic Hwy, Mosier

Twin Oaks is an updated doublewide home perched on a basalt knoll with 11 beautiful acres overlooking vineyards and the Columbia River. Views include river and gorge to the west and north. In springtime see waterfalls on the Washington cliffs. Located 8 miles east of Hood River, Twin Oaks is near Mosier on scenic Hwy 30. This is in the heart of the Columbia River Gorge, with nearby hiking, biking, watersports, boat ramp, & ski areas. Enjoy the numerous wineries and local microbrews in the area.

High Prairie Tiny

This rustic tiny house has french doors on both sides that open up to the woods, and to the pasture. Enjoy the fresh air and get cozy. Nearby to COR Cellars and Syncline, the Klickitat Trail along the Klickitat River is great for hiking and gravel biking, and of course - the Columbia for wind surfing and kite boarding. Wifi can be spotty. An additional tiny house is on the property. Approx. 100 ft away. Host lives on site. Caution: house has many levels. Be mindful when you enter!

Stairway to heaven. Private 2nd floor with view.

Enjoy beautiful views of the Columbia River Gorge from this private second floor space. Easy access to hiking trails, biking, windsurfing, golfing, snow skiing and more! Only 5 miles from Hood River, with a variety of restaurants and unique shops. Visit a number of fruit orchards on the “Fruit Loop”. Wine tasting and breweries are also available. Stay put, relax and enjoy the view, or be as active as you want to be. Come enjoy the endless opportunities in the Columbia River Gorge!

Treehouse in Stevenson, WA Columbia River Gorge

Aptly named the Osprey Treehouse because of the multiple Osprey that spent the summer hovering and watching us build this 20-foot octagon building around a single grand 42-inch old Douglas Fir. Oversized windows and a sliding door give you the feeling of being high up in the trees. Sleeps 2 adults. For safety reasons, we do not allow pets or children younger than 12. The entrance is level and parking close. The cleaning fee is $50 and applicable taxes are already added to your bill.

Debbie Does The Dalles

We welcome you to enjoy our newly built peaceful home overlooking the Columbia Gorge. The patio provides a beautiful daytime view of the Columbia Gorge and mountains as well as a twinkling nighttime view of the city. This slice of heaven is located in The Gorge near restaurants, breweries, hiking, fishing, rafting, and kiteboarding. 5 minutes to everything in town. All one level with easy access to showers. Please note that there is a steep driveway to get to our street.

Now Sleeps 12! Escape to the Pines!

NEWLY remodeled! Now room for 12! Our towering A-frame with floor to ceiling windows invites you into the tranquility of slow, country living. Perched peacefully over a grove of Ponderosas with breathtaking views of the Columbia hills and a majestic Mount Hood, this retreat offers an escape from the bustle of urban life and will lull you into a much needed quietude. Enjoy the starry sky on our spacious deck, or a slow savoring of Pinot from a nearby vineyard.

Fort Dalles Farmhouse Inn

***Update alert*** Hot tub added. Relax at this quiet completely remodeled farmhouse. Built in 1900 this house has old world charm with modern amenities. The house is complete with everything you need for a comfortable stay, including a fully stocked kitchen, washer/dryer, wifi, TV, and hot tub. Enjoy everything the gorge has to offer, then unwind in the hot tub. Pets allowed :)

The Pines Guest House

Ditch the hustle and bustle of the daily grind and escape to the tranquility of The Pines Guest House. Our comfortable, two-story farmhouse has everything you need to feel right at home. It boasts 3 bedrooms (all upstairs), 1 bathroom (downstairs), a dining room, kitchen, living room, seating area with desk (and free wifi), reading nook, and lots of outdoor space to explore.

Romantic upscale cabin in the woods

Our cozy 1 bedroom (queen bed) cabin is the perfect place for a romantic getaway or a relaxing escape. Located on 26 acres where deer and turkey roam. Just a few minutes away from I-84 and Hood River. Wildflower season is upon us! Our place is a great base to spend your nights after a day of hiking in the area to view the wildflowers.

Epic game room, Hot tub, Outdoor movie, Fire pit

📅 2026 dates are filling quickly - reserve while you can! Welcome to River Club The Gorge - a perfect blend of relaxation, and entertainment. HIGHLIGHTS: ✨ Game Room (Pac-Man arcade, new pool table, foosball table, darts, chess) ✨ Hot tub ✨ Gas fire pit ✨ Outdoor movie theater ✨ Deck with valley and river views