Vacation rentals in Pilot Rock

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Top-rated vacation rentals in Pilot Rock

Guests agree: these stays are highly rated for location, cleanliness, and more.

Guest favorite

Home in Pendleton

4.98 out of 5 average rating, 61 reviews

Elegant Western Home 3BR 2BA

Our easy to find 3br 2ba home located in a safe quiet neighborhood with fenced backyard view of the city is perfect for guests with children or a relaxing stay for adults. Enjoy being within minutes to local downtown shops and businesses. Local Restaurants, Round-Up Grounds/Happy Canyon, Underground Tours, Children's Museum. Also located within 6 miles is Wild Horse Casino & Resort. Golfing, Movie theater, Bowling, Family Fun Plex, restaurants and more. (Garage access not available at this time)

Guest favorite

Cabin in Milton-Freewater

4.98 out of 5 average rating, 52 reviews

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!

Guest favorite

Townhouse in Pendleton

4.97 out of 5 average rating, 333 reviews

★Heart of Pendleton★Downtown LUXURY & LOCATION★

Pendleton's "Heart of Downtown" is central to the action just off Main Street. One-of-a-kind, 1300 sqft living space accessible from street level. The city-like flat is newly remodeled and decorated to emanate the western and Native American culture of this historic town. Steps away are restaurants, coffee shops, museums, shopping, nightlife & parks. You won't find a better location in Pendleton during the small town's busiest (or quietest) weekends! Perfect for those wanting an uptown feel!

Guest favorite

Home in Milton-Freewater

4.98 out of 5 average rating, 42 reviews

Modern on the Rocks - In the Heart of Wine Country

Located in the world-famous Rocks Wine District, our Mid-Century Modern home has been thoughtfully designed to be your ultimate vacation destination! Enjoy the ½ acre country setting with a fully fenced yard and stylish outdoor living spaces. Our 2 bedroom, 1.5 bath home has 2 king-size memory-foam beds, comfortable seating, a dedicated work space and high-speed internet. Close to Walla Walla’s popular South Side wineries and within 1 mile of several fantastic local eateries and shops.

Guest favorite

Farm stay in Milton-Freewater

4.98 out of 5 average rating, 103 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

Home in Pendleton

4.97 out of 5 average rating, 220 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.

Guest favorite

Home in Weston

4.99 out of 5 average rating, 109 reviews

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.

Guest favorite

Cottage in Pendleton

4.95 out of 5 average rating, 120 reviews

Lil' COTTAGE ON NORTH HILL

2 bedroom 1 bath house. New Central air conditioning & forced air heatIng system. This house could sleep 6 adults if they slept 2 to a bed. Nice clean home with covered porch in front. Full kitchen, full laundry provided. High speed Wi-Fi provided, with smart TVs. No PETS or SMOKING please. If you choose to book this listing you are agreeing to abide by the Binding Arbitration Agreement through Airbnb's Insurance for any issues or injuries that occur to guests, etc..

Guest favorite

Guesthouse in Echo

5 out of 5 average rating, 14 reviews

Diamond X Suite

This special place is close to everything, making it easy to plan your visit. Located within walking distance of two local wineries and five minutes from the golf course. This guest suite is a perfect resting place and mini escape. The bed is very comfortable. The amenities are great with a full kitchen and full bath. It has an outdoor patio with a yard and a gas fire pit. Easily relax in this backyard with a glass of wine sitting by the fire pit.

Guest favorite

Cabin in La Grande

5 out of 5 average rating, 74 reviews

Modern Cabin with great views!

Small but well put together cabin with modern amenities. Very private setting near hunting, hiking, and ATV parks. Property is near public lands and parks, which allows for hiking, biking, creek, horseshoe pit, ATV trail, and bike rides. Property has outdoor pavilion, BBQ, a deck, hot tub and great views. 2 RV electric hook ups and is 22 miles from LaGrande. Perfect get away spot to enjoy nature and spend time with family and friends.

Superhost

Bungalow in Pendleton

4.86 out of 5 average rating, 280 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.

Guest favorite

Bungalow in Pendleton

5 out of 5 average rating, 117 reviews

*The Garden House* Adjustable bed•fire pit•Bbq

Welcome to the Garden House Take it easy at this unique and tranquil getaway, this updated two bedroom home with a vintage flair. Gas fireplace, Hi speed internet off street parking with lit entrance. Feel comfortable with Enhanced cleaning and high end bedding. Easy access from Hwy 84 and OR-11. 11 minutes to wildhorse casino and minutes to downtown and Pendleton Round - up Grounds and Happy Cannon.