Vacation rentals in Milton-Freewater

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Top-rated vacation rentals in Milton-Freewater

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Guest favorite

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, 164 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, 156 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.

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

4.97 out of 5 average rating, 332 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, 278 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, 178 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, 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, 131 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 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, 291 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 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, 146 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.

Guest favorite

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, 290 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.

Guest favorite

A cozy sleeping area features a black metal bed adorned with a white quilt and decorative pillows. A red lamp casts warm light next to a small green bedside table. A vintage-style armchair adds an inviting touch, enhancing the room's comfortable ambiance.

Apartment in Walla Walla

4.83 out of 5 average rating, 344 reviews

Garden Studio/Free Standing/private drive

Cozy studio apartment situated in a park like setting at the back of our 1 1/2 acre property centrally located a mile and a half from downtown Walla Walla. Pristine landscaping. Very quiet and private location. A year round creek runs through our backyard. During the summer months guests have access to our bountiful vegetable garden. If you are looking for relaxation in a beautiful setting…this is it!

Top guest favorite

A rustic barn structure features a two-story design with a wooden exterior. Windows on the upper level provide natural light, while horse stalls are visible on the lower level. The open area is enclosed by a fence, creating a farm-like atmosphere.

Apartment in Pendleton

4.98 out of 5 average rating, 563 reviews

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.