Family-friendly holiday rentals in Umatilla County

Trailside! The Owl’s Nest at Mt Emily Rec Area

3 bedroom (6 beds) cabin tucked in the woods next to Mount Emily Recreation Area (3,700 acres of recreation and miles of free trails) - just minutes from town. Enjoy hiking, biking, and skiing right out the front door. Host a dinner party in the large kitchen, or cook on the BBQ under the covered deck while your dogs play in the fenced yard. Finish your day cozied up next to the wood stove while the kids enjoy a movie in the bunk room. Dedicated workspace, and very fast Starlink internet onsite.

Kitchen · Family · Heating

Peanut Butter Cup on the Hill, 1.2 mi to Round Up

Enjoy some quiet time in this private townhome playing ping-pong, Wii, board games, or ring darts. Better yet, send the kids to play while you relax on the deck by the fire pit under the lights. Or cozy up by one of the two indoor electric fireplaces. Bedroom 1- Queen bed, walk in closet, dresser, sink and mirror with door to the shared bathroom. Bedroom 2- Queen bed, closet, dresser Basement (bedroom 3)- Queen bed, futon, small closet, bathroom with shower, laundry room, access to game room.

Family · Indoor spaces · Bathroom

Elegant Western Home 3BR 2BA

Easy to find 3 bedroom 2bath home just a short distance from freeway exit, located in a safe neighborhood with fenced backyard and view of the city. Perfect for guests with children or a relaxing stay for adults. Enjoy being within minutes to local downtown shops, businesses and restaurants, Underground Tours, Children's Museum Round-Up grounds and Happy Canyon. Also located within 6 miles is Wild Horse Casino & Resort. Golfing, Movie theater, Bowling, Family Fun Plex, restaurants and more.

Kitchen · Family · Bathroom

McKay Creek Bunkhouse

Welcome to McKay Creek Bunkhouse. We are located on McKay Creek 11 miles from the heart of Pendleton, Oregon. This 1900 bunkhouse is situated near the blue mountains and is recognized by the state of Oregon as part of our century farm which is still a working farm. The bunkhouse is surrounded by a couple of acres of grass and wheat fields. Locate just down from the mouth of McKay Reservoir you may see geese, turkeys and deer to name a few wildlife that visit the area. Come and relax.

Family · Kitchen · Location

Mimi’s Hive - Spacious 6 bedroom 5 bath

Welcome to Mimi's Hive!! This large one level, 6 bedroom 5 bathroom home is a great gathering spot for your friends and family. traveling together or meeting up you will have plenty of space to relax in the living area while watching the large screen Roku TV and warming by the gas fireplace. The fully stocked kitchen should have all you need to make a great meal and gather to eat. This home has 3 full bathrooms with 2 additional 1/2 baths. Round up week we have a 4 day minimum stay

Kitchen · Indoor spaces · Decor

Unique Cabin•Very Comfortable•King Bed•Gated

Welcome to a bountiful farmstead in the Rocks District, just minutes from wineries in Milton and Walla Walla. Enjoy a newly remodeled cabin with a full kitchen, bath, dining, and living space, plus a fully connected vintage family bus serving as the main sleeping quarters with a king bed and four twin beds. This unique, private local-legend property is perfect for families, romantic getaways, staycations, and time with cherished friends—start planning your memorable stay today!

Family · Kitchen · Layout

Garden Get Away

Escape to your own private paradise. This one bedroom cottage is surrounded by lush gardens with numerous outdoor seating areas. Its located under one mile from downtown, two parks, and the Grande Ronde River. This private home was lovingly created over a lifetime with many creative decorative touches. Your cooking needs are amply met with conveniences such as a food processor, blender, microwave, drip coffee maker and french press, and outdoor BBQ. Book now for a restful stay.

Family · Kitchen · Decor

*Cozy Downtown Stay* (Private apt. Self check-in)

Beautiful, large apartment located in the heart of Pendleton. This beautiful apartment is stylishly decorated with a relaxing feel. It is fully equipped for a long term stay or a short term comfortable stay. Centrally located to multiple bars, restaurants; walking distance from Pendleton underground tours, Umatilla River levy, Pendleton Center for the Arts, children’s museum & a 15 min walk to Pendleton Round-up. Perfect location for people who want explore or simply relax.

Family · Indoor spaces · Checkout

Weston Mountain Lodge in the Blue Mountains

Weston Mountain Lodge is a grand, open space full of natural light that feels intimate and cozy too. A group of friends or families as well as a couple or an individual would all feel at home here. The house and land inspire reflection and serenity. Weston Mountain Lodge feels magical and “other worldly” - a quiet oasis tucked off life’s busy path. The Lodge is a perfect place to disconnect so you can reconnect, where you can build traditions and create lasting memories.

Family · Indoor spaces · Amenities

Elk Song Inn @ Foothill Retreat-Cozy and spacious

Escape.. Breathe.. Relax.. 1800 sq ft. very cozy retreat on 45 private acres, easy access less than 1 mile from I84, 7 minutes to La Grande, animal friendly, barn and corrals, beautiful views in every direction. Huge fully equipped kitchen. Borders Ladd Marsh Recreation area. A very popular biking and bird watching destination. Only a couple miles to Rocky Mountain Elk Federation land. Near Hot Lake Springs. Feel free to roam around the property.

Indoor spaces · Family · EV charging

Modern Cabin with great views!

Small but well put together cabin with modern amenities. Very private setting near hunting, hiking, and ATV parks. Property is near public lands and parks, which allows for hiking, biking, creek, horseshoe pit, ATV trail, and bike rides. Property has outdoor pavilion, BBQ, a deck, hot tub and great views. 2 RV electric hook ups and is 22 miles from LaGrande. Perfect get away spot to enjoy nature and spend time with family and friends.

Indoor spaces · Family · Sleep quality

The Nature Trails at Burnt Acres

Place yourself in the country on 60 Acres with 4 miles of trail amongst the trees and a creek. You'll have access to this preserved natural area that is great for birding, biking, hiking, and more. The living quarters are a 2 bedroom house that is on the 2nd floor with deck overlooking the creek and wooded area. Bedrooms have 1 queen, 1 full, and a futon mattress.

Indoor spaces · Family · Decor