Vacation rentals in Weston

Cozy & Private Cabin Escape w/ Mtn Views

Come relax in this peaceful setting, only 10 min from dwntn Walla. Bask in the beautiful Mtn views & breathtaking sunsets while relaxing in the hot tub or patio area. No TV here, so it’s the perfect chance to sit back, enjoy nature & connect with your loved ones. Watch the wildlife that the pond attracts in the winter and delight in the beauty of flowering trees/bushes during spring & summer months. Autumn gives way to brilliant hues of red & orange on our lovely trees. A delight in all seasons!

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.

Private Apartment at the Q Corral

Welcome to the Q-Corral, located in the heart of wine country! We are located within a short drive of 5 wineries and can arrange tours to any others you wish to visit. Our apartment is a 1BD 1BA with a full kitchen, spacious deck, and private entrance. There is also an 220W EV charger upon request. During your stay, we welcome you to experience the "farm life" and interact with the many animals we have on the property. This can include collecting your own eggs for breakfast from our chickens!

"Calico's Chicken House" on Historic Farm

Welcome to "Calico's Chicken House!" We are so happy you found our historic farm which my parents purchased in 1947. Located just down the road from where my great grandparents purchased the original farm which is still in the family today. We named the former chicken house after our favorite farm cat, Calico. She resided there for 17 years and found great comfort. We know you will too. Recently remodeled to accommodate your every creature comfort need. Our house is family and pet friendly.

Mill Creek Ranch, Family/Couples Retreat-3 bd,

Welcome to The Lane Ranch, your home away from home. Perfect for your family vacation, girls' or guys' getaways, and informal gatherings. Secluded and quiet, this 1-story home is only 1 mile from the airport and wineries and ~4 miles from downtown. Enjoy the picturesque beauty of the 13.5-acre ranch, situated right by a little creek. Walking trails and Rooks Park are close by! Up the road is Klickers, local produce, and an antique store, where you can buy fruits, vegetables, and souvenirs!

Luxurious farm retreat: private guesthouse

Located in the heart of farmland & orchards, this 2nd story retreat overlooks a creek & park like grounds. The stand-alone building with private entrance boasts 800 sq ft of living space with bedroom views of the Blue Mountains. A tiled bathroom with over-sized shower is sure to soothe your spirits. Relax in the quiet country setting & experience the privacy of this picturesque place. Farm life outside, luxury inside. Spa inspired linens, imported towels, plush robes & cozy slippers await.

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!

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.

Peach Island Farms - Annie's Place

Located in the Walla Walla Wine Region and Rocks AVA of Milton-Freewater, Annie's Place is nestled between the Walla Walla and Little Walla Walla Rivers. The property encompasses 5 acres of pasture offering a peaceful stay in a small farm setting. At various times, the farm is home to Cotton the Great Pyrenees, lambs, bees, and multiple unnamed chickens, turkeys & roosters ... the menagerie of animals changes all the time. We would love to have you visit.

Private Creekside Farm Stay near Walla Walla

Welcome to your quiet farm escape in Oregon 🌾 Enjoy a peaceful stay on a working farm with wheat fields, cattle, vineyard, and the calming sounds of Couse Creek nearby. Surrounded by open land, wildlife, and mountain view, this is a true escape with total privacy—no neighbors. Located just 3 miles from Milton-Freewater and 10 miles from Walla Walla wine country. Perfect for a quiet getaway, wine tasting trip, or a relaxing break in nature.

Beautiful Cabin on a river, close to wine country

Beautiful Cabin property in the Blue mountains on the South Fork of the Walla Walla River. Close to wine country and perfect destination for a weekend retreat during any time of the year. Can host family reunions or just a couple wanting to get away for the weekend. There are three seperate cabins on the property that guests can enjoy. Equipped with full kitchen, three living rooms, two full baths, laundry room and a total of five bedrooms.

Sage Cottage

Come visit the Sage Cottage for a great unique getaway (with some light holiday decor!), close access to downtown Milton Freewater, and 15 minutes to beautiful Walla Walla. 30 minute drive to Pendleton and premium shopping centers. Fully fenced backyard is perfect for family events. While not perfect, this home is close to our hearts and we hope you will enjoy it as much as we do!