Vacation rentals in Milton-Freewater

Cozy & Private Cabin Escape w/ Mtn Views

Come RELAX in this peaceful setting, only 10 min from dwntn Walla. Bask in the beautiful Mtn views & breathtaking sunsets while relaxing in the hot tub or patio area. No TV here, so it’s the perfect chance to sit back, enjoy nature & connect with your loved ones. Watch the wildlife that the pond attracts in the winter and delight in the beauty of flowering trees/bushes during spring & summer months. Autumn gives way to brilliant hues of red & orange on our lovely trees. A delight in all seasons!

Cottage with views, remote workers, couples, pets

COTTAGE SPACIOUS VIEWS 1BD/1BA 660 sqft, full kitchen, surrounded by rolling hills. Perfect for remote workers or couples getaway. Bluewood Ski Resort 20 mi. Walla Walla 35 min. In town, but feeling is Zen and rural due to being secluded, off-street. Large, fenced back yard is especially pretty in spring--you and dogs will love, (shared with sun rm). The local beauty is stunning in all seasons. Originally an artist's studio--Meredith's good energy left for you! Stand-up desk for remote workers.

Alder House Has It All

Visit Walla Walla in the comfort of a home-away-from-home when you stay at this 3-bedroom, 1.5-bathroom remodeled vacation rental house that sleeps up to 8. This beautifully updated home features modern touches throughout and a prime location, just a short walk from downtown Walla Walla and Whitman College. Whether you’re wine tasting in one of the 30+ downtown tasting rooms or adventuring in the Blue Mountain Country, you’re sure to have a memorable stay at this picturesque neighborhood home.

Walla Walla Guest House- Relax, rewind, rejuvenate

Newly updated, exquisite retreat in Walla Walla’s finest historic neighborhood! Luxurious linens, small kitchen & upscale bathroom with heated floors, provide thoughtful details throughout! Tranquil garden views frame the backdrop for this charming guesthouse. Stroll tree lined streets through Whitman campus to downtown shops, restaurants, wineries and parks! You’ll love the location, ambiance, outdoors space, & neighborhood. It's great for couples, solo adventurers or business travelers.

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!

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.

Vue 360 - Loft Style Townhouse right downtown

Panoramic views of the Walla Walla Valley from the rooftop deck set the backdrop for an outstanding stay. Walk to city center w/ tasting rooms, restaurants and shopping. Browse the farmers market for fresh fixings for a fabulous dinner prepared in the gourmet kitchen and served al fresco on the rooftop deck. 3 bedrooms each with their own ensuite bath provide comfort and relaxation for all. Great for couples, business travelers, and groups of friends.

Modern on the Rocks - In the Heart of Wine Country

Nestled in the renowned Rocks Wine District, our Mid-Century Modern home offers a perfect getaway on a ½-acre country setting. Fully fenced with a secure gate, it’s pet-friendly! Enjoy 2 bedrooms, 1.5 baths, king memory-foam beds, a workspace, and high-speed internet. Stylish outdoor spaces and a new private outdoor shower (2025) add luxury. Minutes from Walla Walla’s wineries, eateries, and shops. Your ultimate retreat!

The Modern NEW Condo in Downtown Walla Walla

High-End luxury condominium located in the heart of downtown Walla Walla. This modern unit sits 2 blocks off the infamous Historic Main Street, walking distance to all that Downtown has to offer. Restaurants, tasting rooms, boutique shopping & entertainment. This freshly renovated Condo is complete with all the amenities necessary for a wonderful stay. Forgot to pack an essential? We likely have you covered!