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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.

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.

~Pearl Cottage~

1930’s French cottage for an ADULT ONLY get away NO WORK CREWS/TEAMS. The coffee-breakfast size kitchen is tiny. Features vintage dishes, 30’s silverware and crystal bar service. NOTE: dinning room and kitchen are tiny. The down sofa and working fireplace make the living room a relaxing place to unwind. Bedrooms furnished with velvet headboards from Anthropology, down bedding for a luxurious nights sleep. 4 blocks from the Round Up grounds, parking included. NO children under 13. No pets.

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.

Columbia River Retreat

Escape to this stunning 4BR, 3BA riverfront retreat near Hat Rock in Hermiston, OR! With a spacious backyard leading directly to the Columbia River, enjoy swimming, paddle boarding, or simply soaking in the views. This two-level home features a full kitchen, expansive windows showcasing the water, and a peaceful setting just 50 minutes from Walla Walla and Tri-Cities wine country. A short 15 minute drive from downtown Hermiston. Perfect for a relaxing getaway or an adventure-filled stay!

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.

Cozy Pendleton Studio Hideaway

Welcome to your cozy Pendleton retreat! Perfect for two, this spacious studio offers all the comforts of home, complete with your own private driveway and entrance. Relax with a movie on the TV or stay connected with high-speed WiFi. The kitchenette is equipped with a microwave, hot plate, toaster oven, and all the essential cooking tools, making it easy to whip up a meal. Whether you're here to explore or unwind, this studio provides a comfortable and convenient base for your stay.

NEW! 2 Kings/Hot Tub/Access to Full Gym/Espresso!

Sage Haven: a modern, newly remodeled home designed to provide you with a peaceful and relaxing get-away. Whether you’re here for the world famous Round-up, Whiskey Fest, a restful retreat with friends or family, work travel, or a family vacation, you will find that this home will serve all your needs. Located at the base of the Blues, you are just minutes from tranquil nature or exciting downtown activities. Message me to learn about short/long-term discounts for you and pets!

4 Bedroom Pendleton Craftsman

Welcome to our vintage Pendleton Craftsman, a newly renovated and inviting 4-bedroom 1-bath home located on the north hill steps away from the Round Up grandstands. Explore charming local shops, savor delicious meals at nearby restaurants, and immerse yourself in the town's rich heritage. For outdoor enthusiasts, hiking trails and scenic parks are just a short drive away. Embrace the charm of this picturesque town while enjoying the comforts of this beautifully appointed home.

Stay Awhile - Pet Friendly, Fenced Yard

Welcome to Pendleton! We are excited to have you stay and hope you enjoy this home away from home. Our shabby-chic abode is family and pet friendly, and the perfect space to relax while you stay in our Northeastern Oregon town. Our location places you within minutes of anything you may want to do here or anywhere you may want to be. This 3-bedroom, 1-bath comfortably houses 6 people; Making it perfect for your family or a small group.

🤍Cassa on Main 2bdrm 2bath self~check~in

This stylish place is close to must-see destinations, located in the heart of downtown Pendleton. This unique apartment is within walking distance from bars, restaurants, river walk and coffee shops. This apartment is a very large apartment with updated touches and a very cozy look. It is great for a short term stay, and equipped well for a longer term stay.

NEIGH-bors Barndominium

NEIGH-bors is on the top floor of a barn just within the city limits of Pendleton, Oregon. It's 600+ square feet, and includes a nicely stocked kitchen and full bathroom, a queen bed in the bedroom and an air mattress and/or floor mattress in the living room. This "barndo" is an attractive option for those who desire convenience and rustic charm.