Places to stay in Milton-Freewater

Guesthouse in Summerville

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.

4.92 out of 5 average rating, 37 reviews

Summerville Stables Guesthouse

SaraRating, 5 stars3 weeks ago

Tracy's place was exactly as the pictures showed. It was beautiful and relaxing. The place was spacious, clean, and stocked with any items we needed. We really loved walking around, seeing the animals. The walk through the pasture was like a dream. I feel like the price matched the quality of the place. Tracy responded quickly to any messages sent to her. Her place is one of the best places we have stayed!

4.99 out of 5 average rating, 358 reviews

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

The Loft on Birch, Walla Walla

BryanRating, 5 stars1 week ago

We had a very nice time at the loft - nice layout, nice amenities, very comfortable for our group. Everything we wanted was within walking distance. Day trips, out of town, were all fun. If we make back to Walla Walla, we plan to stay again.

4.96 out of 5 average rating, 114 reviews

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

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

HeidiRating, 5 stars1 week ago

Staying at Jan’s place was just exactly what I needed. I was looking for a quiet, peaceful place to start healing after a personal loss. The location has beautiful country surroundings, but is also only a couple of miles from major shopping opportunities. It was perfect. Jan is incredibly sweet and quick to respond to any questions. I hope to come back!

Guesthouse in Walla Walla

A bright and open studio space features a spacious bed adorned with a decorative pillow. Light wood accents enhance the warm atmosphere, and a compact kitchen area is seen adjacent to the sleeping space. A comfortable seating area is included, with natural light pouring in from nearby windows.

5 out of 5 average rating, 16 reviews

At B + B

RubyRating, 5 stars5 months ago

I loved it here! Will be booking here again if I do another trip here! Very friendly host and very helpful. They provide goodies for guests (which is hardly done to my experience). Host is also very helpful by providing pamphlets of things to do in the area. I would 100% recommend booking them! Felt very comfortable and at home here!

Farm stay in Milton-Freewater

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.

4.98 out of 5 average rating, 109 reviews

Unique Cabin Oasis •Cozy•Gated•King Bed

BlytheRating, 5 stars1 week ago

Alex and Katie were absolutely spectacular hosts!! I can't say enough about the gracious hospitality and Alex went above and beyond to make our stay as memorable and special as possible. We loved the cabin and the beds were incredibly comfortable. Our son loved pretending to drive the old bus and we also enjoyed the beautiful property and evenings by the fire (always ready for us when we came back home!). The property is only about 15 mins outside Walla Walla and we appreciated being out in the peace of the country. We are already planning to visit again someday!!

A covered outdoor seating area features a large arrangement of cushioned sofas with decorative pillows, surrounding a wooden coffee table. Soft lighting is provided by string lights overhead, enhancing the tranquil garden setting.

4.86 out of 5 average rating, 85 reviews

PoplarPlace @ The Wesley WW MicroResort ☀️Downtown

SylviaRating, 5 stars6 months ago

We thoroughly enjoy our stay in Walla Walla at this adorable cottage! We were able to walk into town easily and quickly for dining and shopping. There are so many great restaurants to choose from within walking distance, such a convenient location!

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~

KacieRating, 5 stars1 month ago

This was a beyond perfect place for us to stay during a basketball tournament. Easy walk to convention center, rodeo grounds, downtown, everywhere. The house is super charming, very queen and the beds were extremely comfortable. There are too many nice touches to list, but especially the coffee. I would stay here again in heart beat.

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What guests are saying

Shop suite

4.98 out of 5 average rating, 87 reviews1 week ago

The "shop suite" was private, peaceful and quiet. We needed some down time and that's what we got. We enjoyed watching the irrigation as the sun set, listening to the neighbors turkeys and peacocks and watching the cows graze. Nothing disturbed our sleep. The snacks were great and the bathroom is large. We said we would stay again for a short distance get away!

Barn in Milton-Freewater

What guests are saying

Cottage with views, remote workers, couples, pets

4.98 out of 5 average rating, 89 reviews1 month ago

Second time staying at Jennifer’s place. It the perfect stay for a weekend ski trip, very close to bluewood. The stay is super cost, lots of shows on the tv, the scenery is very nice, lots of rolling hills surrounding the place! Jennifer is very kind, communicative, and empathetic. One of my favorite hosts so far!

Guesthouse in Dayton

What guests are saying

The Mays Place Whole House

4.7 out of 5 average rating, 33 reviews6 months ago

I was in this area for a memorial service and my plans were tentative at best for the entire weekend. Stacy so kindly worked with me as the family’s plans changed, and my plans changed, and it could not have been a better arrangement. The gorgeous historic home felt so cozy as soon as you walked in. I stayed in the king sized bedroom with the in-room bathroom. The bed and pillows were so comfortable and there was plenty of room to unwind and relax. This was a much needed respite in such a stunningly beautiful area!

Home in Elgin

What guests are saying

Countryside setting with vineyard & mountain views

4.95 out of 5 average rating, 107 reviews5 months ago

This was our second time staying at Lori’s place. Lori is an excellent host. Responds quickly to messages. I would highly recommend her place. It is well located, very clean and stocked well for breakfast and also snacks. A nice place to relax and the beds are very comfortable.

Guest suite in Walla Walla

What guests are saying

"Pendleton" Quiet & Cozy 1-Bedroom Loft

4.94 out of 5 average rating, 89 reviews1 month ago

My husband and I enjoyed our stay, even though it was one night it was very comfortable, clean, huge TV, extra bathroom supplies should you forget something, and even popcorn for movie night. Nice quiet neighborhood. We went for an evening walk, very peaceful. Watched the sunset and drove into town. Main street is only 6 min away. Lots of great places to eat. We would definitely stay here again.

Guest suite in Pendleton

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Popular amenities for Milton-Freewater places to stay

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BBQ grill

Laptop-friendly workspace

Wifi

Other great vacation rentals in Milton-Freewater

4.99 out of 5 average rating, 90 reviews

A single-story home is presented with a light grey exterior, a welcoming front porch, and a neatly landscaped yard featuring green grass and potted plants. A driveway provides access to a garage, while a fenced area is visible to the side.

Home in Pendleton

Elegant Western Home 3BR 2BA

BeckyRating, 5 stars1 day ago

Enjoyed our stay here. Nice touches like games, DVDs, snacks. There were baby items that would be very useful for young families. Nice decor, comfortable, and good layout of the home. Highly recommend!

A welcoming front porch features a pastel pink door and two white folding chairs with patterned cushions. A small round table is set between the chairs. A door mat with the word 'Hello' is placed at the entrance, with ample natural light illuminating the area.

5 out of 5 average rating, 101 reviews

Blissful Acres

ChristineRating, 5 stars2 weeks ago

We had such a wonderful stay at Alison’s cottage! The space was perfect and was so nicely decorated with many adorable and thoughtful touches. Not to mention snacks and a welcome gift! The backyard was lovely and the location was so picturesque. We loved being so close to so many wineries! And town was a very quick drive as well. Thank you for such a sweet and comfortable stay!

4.91 out of 5 average rating, 175 reviews

Farm stay in Walla Walla

Peaceful Family Farm in the heart of wine country

StephanieRating, 5 stars1 week ago

My girlfriends and I loved Mike’s Airbnb! It was perfect for our girls trip— bedrooms and bathrooms were very clean and proximity to downtown Walla Walla is perfect. Highly recommend!

An inviting living area features two leather reclining couches arranged for comfort, with neutral throw pillows. Natural wood accents frame an open staircase leading to the upper level. Light floods through large windows, enhancing the spaciousness of the connected kitchen area in the background.

4.97 out of 5 average rating, 99 reviews

Rustic Wine Country Farmhouse

TimRating, 5 stars1 week ago

Great place to stay! You are close to hourses and farm type animals. Has a small farm type feel. Not supper close to any restaurant's or stores...but not to far to drive. I meet Jared and he was extremely appreciative of your stay. Very nice to talk to and interested in our trip there for a golf tournament. They greeted us with farm fresh eggs from there chickens. Very thoughtful of them. We will be back next year for another golf tournament and will definitely try to stay again!!!

4.98 out of 5 average rating, 46 reviews

Estate on Wine Route w/Pool on 5 acres

RachelRating, 5 stars6 months ago

Jill’s home was perfect for a family Walla Walla long weekend! The house has four very spacious bedrooms and each bathroom is very nice and clean. The home is so large with large expansive outdoor spaces that are so beautiful. We had a lovely stay here. Jill was very responsive, very kind. We would definitely stay here again and next time come with warmer weather to enjoy the beautiful pool. Thank you for an awesome stay!!

Superhost

A charcoal grill is positioned on a wooden deck, surrounded by a grassy area and bare trees. The landscape includes rolling hills in the distance, and a clear blue sky with scattered clouds enhances the outdoor setting.

Farm stay in Elgin

4.89 out of 5 average rating, 45 reviews

The Country Getaway

BrandieRating, 5 stars2 months ago

If you love the peace and quiet of the country, this place is perfect! We loved it! Beautiful setting and still close to lots of things to do! We will be back

4.94 out of 5 average rating, 268 reviews

A wooden deck features two Adirondack chairs, positioned to overlook a vast expanse of rolling hills and dense pine forest. The setting sun casts a warm glow over the landscape, highlighting the natural beauty of the surrounding area.

Cabin in Walla Walla

Wine Country Mountain Cabin Retreat up Mill Creek

WyattRating, 5 stars1 week ago

Phil’s place was incredibly comfortable and peaceful. We had an amazing stay and won’t forget the amazing views of the mountains anytime soon!