Holiday rentals in Milton-Freewater

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.

Downtown Getaway for Wine Lovers

This stylish space is the perfect getaway for groups or families to enjoy Walla Walla. Nestled in a quiet community a few blocks away from the heart of downtown, this house boasts all of the amenities to make you feel right at home. There's ample space including a chef inspired kitchen & outside seating with fire pit. Easily walk to incredible restaurants & amazing wine tasting rooms that have contributed to the Walla Walla Valley earning the Best Wine Region award for 3 consecutive years.

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!

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.

Northside Getaway ~ Modern ~ Spacious

Relax with the whole family at this stylish North side Getaway! It has plenty of parking and self check in with the keypad. The fully stocked kitchen has all the amenities for cooking, including a coffee bar with complimentary coffees, teas, and hot chocolate. The three bedrooms all have luxury bedding, USB ports, and Roku TVs with streaming options. Enjoy all beautiful Eastern Oregon has to offer and then relax in this cheerful getaway !

La Casita Bonita

Your family will be close to everything when you stay at this centrally-located area in the most quiet neighborhood with a nice size fully fenced back yard. Minutes away from everything including restaurants, parks, and entertainment. And have no worries, when staying in for the night, the wifi is the best the area has to offer. The garage includes a Nema 14-50 plug-in the garage to support EV charging (bring your charging cable).

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!