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Vacation rentals in Milton-Freewater

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Top-rated vacation rentals in Milton-Freewater

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A stunning sunset casts a warm glow over a vineyard landscape. The view features a yellow building surrounded by lush greenery, framed by a white fence. Soft orange and pink hues fill the sky, creating a serene backdrop for the tranquil environment.

Guesthouse in Walla Walla

4.9 out of 5 average rating, 163 reviews

Chateau Adonai

Need to getaway? Want to relieve the stress of the big city, or spend some time in a small peaceful town in your own private residence? We have the small cottage that is right for you. Located on the south side of Walla Walla, a small working farm, surrounded by the Blue Ridge Mountains and nestled in the middle of the South-side wineries, where scenic beauty awaits. Incredible wineries within walking distance and close to enticing restaurants and cultural inspiration, outdoor adventures await.

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

4.92 out of 5 average rating, 155 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, 329 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, 277 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.

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, 177 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

Vibrant purple flowers are featured prominently in the foreground, contrasting with lush greenery in the background. A birdbath is visible among the garden elements, with a decorative pot containing vibrant blooms adding charm to the serene outdoor space.

Guest suite in College Place

4.97 out of 5 average rating, 183 reviews

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.

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, 105 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 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

4.98 out of 5 average rating, 127 reviews

Unique Cabin Oasis •Cozy•Gated•King Bed

Welcome to a bountiful farmstead in the Rocks District- minutes away from wineries in Milton and Walla Walla. You'll enjoy a newly remodeled cabin with a kitchen, bath, dining, and living room. A fully connected vintage family bus is the main sleeping quarters with a king bed and four twin beds. This local-legend property is unique and private - perfect for families, romantic getaways, stay-cations, and time with cherished friends! Begin planning for your marvelous, memorable stay!

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, 307 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 bright sleeping area is highlighted by a floral-patterned quilt draped over a spacious bed, adorned with decorative pillows. Sunflower-patterned blankets rest at the foot of the bed, while soft natural light filters through a window, complemented by pastel curtains.

Tiny home in Milton-Freewater

4.98 out of 5 average rating, 143 reviews

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.

A yellow bench with colorful cushions is positioned under the covered porch of the cottage, offering a welcoming spot. The entrance features a door beside a large window, allowing natural light to illuminate the space. Lush green lawn surrounds the area, enhancing the tranquil setting.

Guesthouse in Walla Walla

4.9 out of 5 average rating, 288 reviews

Woodlawn Garden Cottage

This lovely studio cottage is perfect for one person and “cozy” for two. It overlooks a vegetable garden behind the main house on the two acre property, and is located just 1.5 miles from downtown Walla Walla. We sincerely hope you enjoy your stay with us! Please read all descriptions carefully to ensure our cottage offers what you are looking for and meets your needs for a comfortable and relaxing stay.

Top guest favorite

A spacious living area features a comfortable gray sectional sofa and a cozy red accent chair. A small wooden table is placed beside the chair, accompanied by a lamp. A large television displays a vibrant underwater scene, and natural light filters through a window with a view of greenery.

Guesthouse in College Place

4.9 out of 5 average rating, 775 reviews

Private Guesthouse with indoor pool and hot tub

Come stay in our private Guesthouse located on 2-acres with ample off-street parking and big shade trees. This Guesthouse has a nice landscaped private yard. Relax on the patio with views of the Blue Mountains. Enjoy the indoor pool and brand-new hot tub year-round. Enjoy a pick-up game of basketball on our regulation half-court. Lighted for night play.

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Popular amenities for Milton-Freewater vacation rentals

Free parking on premises

Air conditioning

Other great vacation rentals in Milton-Freewater

Top guest favorite

An inviting living area features a comfortable couch facing a wooden coffee table, which holds a tray of snacks. A large flat-screen television is mounted on the wall, with a cozy electric fireplace visible below. Light floods in through the sheer curtains covering the sliding glass door.

Farm stay in Walla Walla

4.97 out of 5 average rating, 29 reviews

The Bunkhouse

Top guest favorite

The Airstream is showcased under a wooden pergola on a deck, surrounded by a fenced area. A table and chairs are positioned for outdoor dining, with wind chimes hanging nearby. The sky is filled with textured clouds, complementing the serene rural setting.

Farm stay in Walla Walla

4.98 out of 5 average rating, 56 reviews

Airstream Retreat on a Farm Oasis

Top guest favorite

A charming cabin is situated amidst tall trees, featuring a wooden exterior with a sloped roof. A gravel path leads to the entrance, framed by decorative elements, and small plants are positioned at the base. Natural light illuminates the space under a clear blue sky.

Cabin in Waitsburg

5 out of 5 average rating, 24 reviews

Peaceful little Cabin in the woods

Top guest favorite

A charming cabin is set among lush greenery, surrounded by trees and a well-maintained lawn. A gravel driveway leads to the property, while a wooden fence delineates the yard. Sunlight filters through the trees, highlighting the rustic exterior and natural surroundings.

Cabin in Milton-Freewater

4.98 out of 5 average rating, 98 reviews

Beautiful Cabin on a river, close to wine country

Top guest favorite

The exterior of the cottage is set against a clear sky, featuring a well-maintained lawn and pathways lined with stones. A large tree provides shade alongside the patio area, while bird feeders can be spotted nearby, contributing to the natural charm of the setting.

Cottage in Waitsburg

4.98 out of 5 average rating, 45 reviews

Cozy Cottage on Evergreen Lane

Top guest favorite

A bright living area features a large window allowing natural light to illuminate a beige tufted sofa and a cozy armchair. A textured area rug covers the floor, and greenery is provided by a nearby indoor plant. Double doors lead to an outdoor view.

Cabin in Milton-Freewater

4.99 out of 5 average rating, 68 reviews

Cozy & Private Cabin Escape w/ Mtn Views

A cozy living area features a dark upholstered couch positioned near a wooden coffee table. A television is mounted on the wall, opposite a light window partially covered by sheer curtains. A doorway in the background leads to a well-lit bedroom area.

Home in Milton-Freewater

5 out of 5 average rating, 45 reviews

Blue Mt view in wine country

Top guest favorite

The cabin is perched on a hillside, surrounded by tall trees. A welcoming porch extends across the front, and two dormer windows accentuate the peak of the roof. Natural greenery frames the view, enhancing the connection to the surrounding landscape.

5 out of 5 average rating, 11 reviews

The Cabin at Bobsled