Holiday rentals in Milton-Freewater

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!

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.

"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.

Rustic Wine Country Farmhouse

Peaceful, private home in the countryside of Walla Walla, near wineries, colleges, walking trails, and just a few minutes from the City Center and downtown. With a beautiful view of the Blue Mountains, small aircraft landing at nearby Martin Airfield, horses and chickens next door (we provide fresh eggs for your stay!), and a spacious private fenced backyard, you have all the luxuries of a quiet country retreat, and the convenience of being only minutes from charming and historic Walla Walla.

Retreat on Bellevue for a Wine Tasting Getaway!

Peaceful and quiet space with everything you need for a weekend getaway! This is a fully private guest suite with private entrance on the lower level of my home (split level entry) Close to downtown Close to Whitman College, grocery stores, restaurants, and wine tasting venues. One queen bed and full size futon. TV ( YouTube TV, Amazon Prime and Netflix) Kitchenette (NO stove/oven) and full private bath. Also available for guest use: laundry and outdoor covered patio with table and chairs

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.

The Sunny House

This home has a vintage appeal. It was built in the mid 1900’s and is located on the north hill within walking distance of downtown Pendleton and the Pendleton Roundup Grounds. A detached garage sits next to the home and is also available for storage. The home is in a quiet neighborhood. It is an easy walk to the Umatilla Riverwalk, Roundup Grounds and downtown. We have two neighborhood parks. One is adjacent to a small neighborhood coffee shop and and cafe, 8 blocks from the house.

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!

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.

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.

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!

This is a Spacious Private Suite/ Private Entrance

This is a spacious suite with a private entrance and porch-front parking. There is a security door with black out curtains that provides fresh air and privacy. Use the kitchenette table and chairs or enjoy your morning coffee on the covered porch, rain or shine. The apartment is kept spotless and sanitized for your complete comfort. The hosts are on site and available for all of your needs.