Places to stay in Milton-Freewater

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Top-rated places to stay in Milton-Freewater

Guests agree: these places to stay are highly rated for location, cleanliness, and more.

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Guest favorite

A wooden dock extends into a calm pond, surrounded by greenery. Two individuals stand on the dock, while another is positioned near the water's edge. Lush trees frame the scene, and a distant view of rolling hills is visible in the background.

Guesthouse in Summerville

4.92 out of 5 average rating, 37 reviews

Summerville Stables Guesthouse

Make some memories at this unique and family-friendly horseback riding stables! Stay in our farm’s 3 bedroom guesthouse with private entrance and panoramic views of horse pastures out every window! Relax on the back porch, enjoy the hot tub, fire pit & BBQ or sign up for a riding lesson, trail ride, or cattle sorting! Horses galore and many other friendly farm animals to see and pet. Horse boarding available too! Can be rented with our Summerville Stables Farmhouse to accommodate larger groups!

Top guest favorite

A hot tub is situated in a private outdoor space, accompanied by sturdy steps for easy access. The tub is filled with clear water, reflecting sunlight under a bright blue sky. Surrounding gravel landscaping complements the modern exterior of the building.

Loft in Walla Walla

4.99 out of 5 average rating, 358 reviews

The Loft on Birch, Walla Walla

High-End luxury apartment located in the heart of downtown Walla Walla This modern-industrial Condo sits in downtown Walla Walla, walking distance to all historic main street has to offer: restaurants, tasting rooms, boutique shopping & entertainment. Relax on the large balcony overlooking town or for more privacy enjoy the 2nd enclosed, covered patio. This spacious, open concept apartment offers almost 1800 sq ft of living space, complete with all the amenities necessary for a wonderful stay.

Guest favorite

A spacious outdoor area features a fire pit surrounded by stone seating, with wooden adirondack chairs arranged nearby. Various landscaping elements create distinct zones, including a shed and pergola. Lush greenery and trees provide privacy, contributing to a tranquil atmosphere.

Tiny home in Walla Walla

4.96 out of 5 average rating, 114 reviews

Tiny House, Hot tub, spacious yard, close to town

Escape for a private, relaxing stay at this unique tiny home in Walla Walla. Close to town, excellent restaurants, and beautiful estate wineries nearby. We are in the county on acreage, in an upscale neighborhood, with mountain views. Large yard, outdoor kitchen, fire pit, sit in the hot tub and watch the stars. Activities: biking, hiking, skiing, art walks, and as always, live activities in town. A master suite is also available to rent, next to the tiny home, if you have friends to join you.

Guest favorite

A charming guesthouse exterior is framed by lush greenery and flowering shrubs. A stone path leads to a pair of black French doors, complemented by a small outdoor seating area featuring white chairs and pink cushions. A unique hanging chair is visible in the background.

Guesthouse in Walla Walla

4.92 out of 5 average rating, 224 reviews

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.

Top guest favorite

A spacious outdoor area is surrounded by lush green grass and tall trees. The wooden structure of the cabin is visible, complemented by a small patio area with seating. In the background, rows of plants indicate the presence of gardens or vineyards, under a clear blue sky.

Farm stay in Milton-Freewater

4.98 out of 5 average rating, 109 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!

Guest favorite

A well-appointed kitchen features white shiplap walls and a decorative pendant light. A modern stainless steel refrigerator is positioned next to a spacious countertop adorned with a subtle backsplash. Natural light filters through a window, illuminating the patterned flooring.

Home in Pendleton

4.97 out of 5 average rating, 227 reviews

Pendleton River Parkway House

When you stay here, you truly feel at home while surrounded by modern farm style furnishings. We are conveniently located along the Umatilla River and less than a five minute walk from the Pendleton Round Up grounds and historical Main Street. This is especially convenient during Round Up or one of the many concerts Pendleton hosts. The property has recently been refurbished including an updated kitchen and bathroom. The backyard is a nice place to sit and enjoy your coffee.

Top guest favorite

Home in College Place

5 out of 5 average rating, 16 reviews

Large Home-Hot Tub-4 King Beds-Walla Walla 8 min

Lilac-Rosebud is a spacious 4-bedroom, 3-bathroom retreat just 8 minutes from downtown Walla Walla. Designed for families, wine lovers, couple groups, corporate retreats, and friends’ getaways, this home comfortably accommodates up to 9 guests. It has two separate living rooms and two fully equipped kitchens. It is perfect for groups seeking both privacy and shared experiences. Step outside to enjoy the expansive outdoor area and unwind in the private hot tub.

Guest favorite

An inviting exterior view of the guest house showcases a well-maintained lawn bordered by trees and shrubs. White shutters and a picket fence create a charming ambiance. A neighboring structure is visible in the background, offering additional outdoor space.

Guesthouse in Kennewick

4.94 out of 5 average rating, 170 reviews

Guesthouse privacy near Clover Island

Get a great night's rest in our quaint national-park-themed guest house. Private Entrance. Wake up refreshed and ready for a day of visiting wineries, events on the Columbia river, Golf, sporting events, or just visiting family. Our guest house is walking distance to the River, Clover Island, and several wineries. Easy access to all areas in the Tri-Cities. Five minutes from airport. Free Parking for one car in shared driveway. One Queen Bed for sleeping.

Guest favorite

A modern multi-story building is framed by neatly trimmed shrubs and trees along the sidewalk. Large windows enhance the façade, allowing natural light to illuminate the interior spaces. The brick exterior contrasts with the greenery, presenting a stylish and contemporary ambiance.

Townhouse in Walla Walla

4.96 out of 5 average rating, 271 reviews

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.

Superhost

A light-filled dining area is accessed through double glass doors, featuring a vintage table surrounded by four blue dining chairs. Natural light filters through the windows, enhancing the bright and airy feel of the space. A decorative light fixture hangs overhead.

Bungalow in Pendleton

4.87 out of 5 average rating, 282 reviews

~Promenade Cottage~

The little 1939 house is only 2 blocks from the busy Round Up grounds, so no need to worry about parking. The cozy ambiance of the house is wonderful and the outdoor garden is a relaxing place for a cup of coffee. Great for bridal parties, business travel and families. On a busy street, but she’s away from the road. I accommodate guests with allergy disabilities. NO pets. Basement is NOT occupied! NO extra guests.

Top guest favorite

The kitchen features modern cabinetry in muted tones, along with stainless steel appliances. A dining area is visible with a light-colored table and four chairs. Natural light enters through a window dressed with sheer curtains, illuminating the warm wooden flooring.

Home in Pendleton

5 out of 5 average rating, 14 reviews

Family cottage

Comfortable family cottage that your entire family will enjoy. Located on a quiet street on the North Hill close to downtown, and walking distance of the Pendleton Roundup Grounds. There is a driveway along the north side of house for off street parking. The home is in a quiet neighborhood. It is an easy walk to the Umatilla Riverwalk, Roundup Grounds and downtown.

Guest favorite

The exterior of the guesthouse is illuminated by string lights, highlighting the covered patio area with a dining table and several chairs. A well-maintained lawn is visible, bordered by stone pathways and illuminated by soft outdoor lighting.

Guesthouse in College Place

4.89 out of 5 average rating, 742 reviews

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.