Holiday rentals in Milton-Freewater

Lux Boho Bungalow in Walla Walla

CASA LUNA ~ Welcome to our luxury bungalow with bamboo flooring, modern amenities, and a Hot Springs 52-jet Hot Tub. Indulge in a spa-like rain shower with Italian rain-textured wall tile. Two queen beds in lockable rooms with windows and greenery. Kitchen, bar, & open dining room with high end appliances & entertainment on a 65” 4K TV. Spacious rear porch for outdoor living & private hot tub. Experience ultimate relaxation just walking distance from WWU & 5 minute drive to downtown Walla Walla!

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.

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.

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.

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.

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.

Parkview Loft 0.8 miles from WW University

Bright and spacious Loft with open Living/Dining and Kitchen area. Large, comfy couches positioned in front of a warm and cozy gas fireplace and Smart TV. Prep a meal in the spacious kitchen with all new appliances and cabinets. All new dishes, cookware and utensils. Enjoy coffee on the patio from a Keurig. There are 2 Bedrooms with Queen size beds and an open Loft area at the top of the spiral staircase with a Queen bed as well. Great place to enjoy family and friends.

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.

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.

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.