Family-friendly holiday rentals in Gresham

Cozy Private Suite by the Rivers

Hi! We're Robyn and Chen, a young, newly-wed couple full of life and energy. This listing with a private entrance helps us pay for our first home! Just four quiet blocks to the Washougal River and over 16 miles of gorgeous PNW trails. We both work from home so we have the best fiber internet available. We're pretty quiet except when we are in the attached stained glass studio or laughing together. We welcome everyone, LGBTQ, traveling nurses, or anyone who wants to explore the Portland area.

Flying Frog Yurt w/Mountain View (Easy Checkout!)

(EASY CHECK-IN. EASY CHECK-OUT) Stunning 2,100 sq. ft all-season (heat and A/C) yurt house with million-dollar panoramic views of Mt. Hood, Mt. St. Helens, and the Cascade Range. Decked with bespoke furnishings and one-of-a-kind decor, the space delivers an immersive experience in a premier neighborhood, combined with the best views in Portland. The home is fully-stocked and is 14 miles from the airport, minutes from urban amenities, with beaches, gorge, and Mt. Hood accessible for day outings.

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.

Horse Barn Apartment on a Beautiful Farm

The Apartment is spacious, beautiful and sleeps 2 in a queen bed. Up to 2 more people can stay but bring pads and bedding for them. Enjoy the private balcony overlooking the woods & creek. The Bath House is for you only but is a separate building & located only 20 feet away. It has a claw foot tub, shower, sink, etc. It is worth the walk. Enjoy a farm get-a-way. Our place is amazing but rural so dogs bark, geese honk, donkeys bray, horses neigh, etc. Join us to slow down.

Fresh + Clean, Walk to Edgefield and Town

Small and cozy studio in new house, family-neighborhood, walking distance to town, Edgefield, coffee, food, art, parks. Cute small-town vibes, proximity to nature and city. Pet friendly, with fenced yard 10 min walk to the McMenamins Edgefield 7 min walk to food carts pod 20 min drive to PDX airport 1 hour drive to Mt. Hood Near Outlet Mall Near parks and art galleries, museums Gateway of The Columbia River Gorge with dozens of hikes, rivers, waterfalls Easy freeway access

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!

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.

Tiny Cabin Guesthouse

Take the flagstone path to this cozy, modern cabin (tiny home) with knotty pine walls, warm light, and a bedroom/loft that overlooks a wildly landscaped yard and garden. This 300 sq ft guest house features everything you need for a comfortable stay in the great PNW. Please note: Before booking, be aware the toilet in this home is a composting toilet, not flushing. It will be clean and ready to use with instructions available in the home.

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.

Upscale Troutdale Apartment Near The Edge!

Fantastic Troutdale location across from Edgefield & close to downtown historic Troutdale. Features queen bed, full kitchen and modern finishes. This apartment has privacy and a modern feel. This is a 1 BD, 1BA ADU with it's own assigned parking. Community playground & firepit. Kick back and relax in this calm, stylish space after enjoying a concert at The Edgefield or a day exploring the Gorge!

Heated Glamping tent, Action sports- Site 3

Stay in a cozy canvas tent tucked in the woods on the grounds of a legendary action sports destination at the base of Mt. Hood. With year-round lift-accessed snow and epic bike trails just minutes away, plus limited access to private skate parks and a full fitness center on site, this is the ultimate basecamp for riders, skaters, adventurers, or anyone craving fresh mountain air.

Cozy Home w/ Ping Pong Table, Fire Pit & BBQ

Welcome to our contemporary 2-bedroom residence, meticulously designed to enhance your Portland visit. Conveniently located just 15 minutes from PDX airport, a scenic 20-minute drive from the breathtaking Multnomah Falls, and a mere 50 minutes from the renowned Mt. Hood's Ski Bowl & Timberline, catering to skiing and snowboarding enthusiasts.