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Vacation rentals in Weston

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Top-rated vacation rentals in Weston

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Top guest favorite
A scenic view from a balcony captures rows of lush vineyards stretching across a gentle landscape. The distant Blue Mountains create a serene backdrop under a clear blue sky, enhancing the tranquil atmosphere of the property.
Farm stay in Milton-Freewater
4.91 out of 5 average rating, 164 reviews

Tum A Lum Ridge Guesthouse in Walla Walla Valley

Welcome to Tum A Lum Ridge Guest House, your private retreat just minutes from downtown Walla Walla. Hidden along a private drive, our 10-acre property boasts breathtaking views of the Blue Mountains, a serene pond, and the tranquil Walla Walla River. Experience a seamless blend of luxury and nature, with outdoor spaces perfect for relaxation. Less than 1.5 miles from world-class vineyards and tasting rooms on Pepper Bridge Road, you’re ideally located for exploring the best of the wine country.

Top guest favorite
A friendly mini-donkey is seen peering through a metal gate at the entrance to Q Corral. A stone sign displaying the name 'Q Corral' is prominently featured in front of the donkey, with grassy fields and structures visible in the background.
Guest suite in Walla Walla
4.98 out of 5 average rating, 361 reviews

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!

Top guest favorite
A wooden deck features two Adirondack chairs, positioned to overlook a vast expanse of rolling hills and dense pine forest. The setting sun casts a warm glow over the landscape, highlighting the natural beauty of the surrounding area.
Cabin in Walla Walla
4.95 out of 5 average rating, 282 reviews

Wine Country Mountain Cabin Retreat up Mill Creek

If you are looking for a unique and quintessential Airbnb experience, you have found it! This cabin is a very private retreat for a romantic get-away, a gathering with friends, or for a special occasion. You will enjoy views of the surrounding pine forest in a tasteful, modern, and updated cabin with every amenity. Drive just minutes to the restaurants and wine tasting attractions in Walla Walla, or stay home and cook, barbecue, enjoy one of three outside decks, or take a walk in the woods.

Guest favorite
Tiny home in Walla Walla
4.96 out of 5 average rating, 137 reviews

Tiny House, Hot tub, spacious yard, close to town

Escape for a private, relaxing stay at this unique tiny home in Walla Walla. Close to town, excellent restaurants, and beautiful estate wineries nearby. We are in the county on acreage, in an upscale neighborhood, with mountain views. Large yard, outdoor kitchen, fire pit, sit in the hot tub and watch the stars. Activities: biking, hiking, skiing, art walks, and as always, live activities in town. A master suite is also available to rent, next to the tiny home, if you have friends to join you.

Top guest favorite
A rustic bedroom features wooden walls and beams, creating a warm ambiance. A black metal bed frame holds a quilted bedspread, while decorative pillows enhance the look. Natural light enters through two small windows adorned with curtains, and wooden furniture complements the charming decor.
Farm stay in Waitsburg
4.97 out of 5 average rating, 185 reviews

"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.

Top guest favorite
A bright living area features a cozy sofa adorned with decorative pillows. A wooden cabinet displays various items, while a small table provides additional space. Light streams in through the window, highlighting the rich textures of the flooring and the simple decor.
Guesthouse in Milton-Freewater
5 out of 5 average rating, 110 reviews

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.

Top guest favorite
A welcoming bunkhouse is set amidst lush green grass, with two pink chairs positioned on the front porch. Surrounding trees provide shade, while the structure features a wooden deck and a traditional roof. A sense of tranquility is enhanced by the open outdoor space.
Tiny home in Pilot Rock
4.96 out of 5 average rating, 326 reviews

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.

Top guest favorite
A rustic cabin is illuminated at night, surrounded by tall trees. Outdoor seating is arranged in front, and a light fixture casts a warm glow over the porch. The serene setting creates a peaceful ambiance, inviting relaxation beneath the stars.
Farm stay in Milton-Freewater
4.99 out of 5 average rating, 138 reviews

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!

Top guest favorite
Snow-covered trees frame a cozy mountain lodge, which is partially obscured by frost-laden branches. The clear blue sky contrasts with the white landscape, creating a serene winter scene. The surrounding nature suggests a tranquil and inviting outdoor environment.
Home in Weston
4.99 out of 5 average rating, 125 reviews

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.

Top guest favorite
A spacious bed with a wooden frame is centered in the room, adorned with decorative pillows featuring animal motifs. A small dog relaxes on the bedspread, while warm light fills the space, highlighting the inviting atmosphere.
Barn in Walla Walla
4.99 out of 5 average rating, 308 reviews

Horsing Around in the Quiet Barn.

Come visit our barn! One apartment all to yourself with walk out to a grassy area. Living area separate from bathroom and shower. Enjoy the country but still only 3 miles from downtown Walla Walla. Southside wineries close by. Feed the horses, chickens, and goats if you'd like. Views of the Blue Mountains can't be beat from your king size bed. We have 240 volt charging outlet for your Tesla (or electric car). We would love to welcome you or let you relax in private.

Top guest favorite
A charming cottage is set in a green landscape, surrounded by lush trees and shrubs. Two red chairs are placed on the front porch, inviting relaxation. A small patch of gravel leads to the entrance, and the sunny sky adds to the serene environment.
Cottage in Summerville
5 out of 5 average rating, 187 reviews

Century Farm Charm at the Century Pine Cottage

Century Pine Cottage is located on the historic McKenzie Century Farm providing modern lodging comfort in a peaceful and scenic rural setting close to all northeast Oregon has to offer. Twelve miles from La Grande and within an hour of Eagle Cap Wilderness, historic Pendleton and Baker City, Walla Walla wine country and so much more. Use as a base or sit and enjoy bird and wildlife viewing, or a good book and the scenic backdrop of the northern Grande Ronde Valley.

Top guest favorite
A modern barn-style structure is set against a colorful sky at sunset. The building features large windows and a distinctive cupola. A windmill stands nearby, and a grassy lawn extends in the foreground, bordered by wooden fencing.
Farm stay in Walla Walla
4.97 out of 5 average rating, 148 reviews

SpringBranch Bunkhouse. Country living w/ hot tub.

Spring Branch Bunkhouse is nestled in the Walla Walla Valley in the heart of wine country and the base of Blue Mountains. Enjoy an evening sunset on your private deck, watching the pheasants and quail meander through the 10 acre property. Take a walk along our namesake, Spring Branch stream or sit beside our spring-fed pond. The Bunkhouse is a relaxing country setting, surrounded by wineries and within 3 miles of Downtown Walla Walla.

Popular amenities for Weston vacation rentals

  1. Airbnb
  2. United States
  3. Oregon
  4. Umatilla County
  5. Weston