Vacation rentals in Weston

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.

The Potter's Retreat Tiny House with 2 Queen Beds

Experience tiny living in this cabin-like cottage (432 sq. feet + loft) nestled in the middle of wine country. It is located in a large private backyard with a private parking area and a sidewalk to the door (a few stairs are required). It is uniquely secluded with country views which can be enjoyed on the porch or at the fire pit. Near College Place and only a 10 minute drive to downtown Walla Walla. Fresh roasted coffee. *Now offering a Level 2–50 AMP EV charging outlet (NEMA 14-50R).

Highland Hideout

Romantic getaway in the heart of wine country! Kick back and relax in this serene, stylish space—a beautifully furnished one-bedroom apartment featuring a queen-size bed and two flat-screen TVs with Roku. In a quiet neighborhood with dedicated parking near entrance. Self-check in with the code sent on the day of arrival. Private patio area with table and chairs. The two-person spa is an ideal spot to unwind and take in the view. EV charger for free use. Small, well-behaved dogs welcome.

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.

Cheerful 2-bedroom cottage w/hot tub

A nicely renovated 2 bed, 2 bath cottage style home in a quiet cul-de-sac, 2.8 miles from downtown Walla Walla. Enjoy an over-sized soaking tub, steam room/shower combo, fully stocked kitchen, gas stove and fire place, Roku TV, outdoor grill and jacuzzi. Explore surrounding areas, including a short walk to a beautiful park w/pond, playground, and rentable space. Enjoy quality restaurants and retail shopping in the beautiful Walla Walla valley.

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.

Vintage Retreat

Escape to a historic 1915 home on 23 acres in Milton-Freewater’s Rocks District. This charming property features 4 bedrooms with 3 Queen beds and 2 Twin beds, 2.5 baths, and 1925 sq ft of living space. Relax by the cozy fireplace, cook in the updated kitchen, or savor the patio with peacful orchard views. Ideally located near Walla Walla’s wineries, dining, golf, boutique shops, art, and museums. Perfect for a serene wine country retreat!