Vacation rentals with a hot tub in Umatilla County

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!

Romantic Moonrise Suite

The romantic Moonrise Suite is a special Wine Country experience. This unforgettable Suite places you right in the middle of a Vineyard with Mongata Winery on site. Breathtaking views, walks to the Walla Walla River or relax and take it all in. Back at the suite, melt into a California King poster bed, stuffed chairs, swim size Hot-tub, private patio+ fire pit + stargazing/seating area. Enjoy a Nespresso Euro coffee + AM basket of local light bites (provided by owner/staff) to start your day.

Bear Den: Hot tub, horse shoes, buck hunter!

Welcome to the "Bear Den," a newly updated retreat in the heart of Pendleton, Oregon. Enjoy the fresh modern-rustic design of this perfect home base for your exploration of the town and its many events. This rare find a short walk to the Pendleton Roundup and downtown attractions. It's also the perfect retreat to stay in and relax. Enjoy the large backyard, play horseshoes, hot tub, or fire pit. Inside, play air-hockey, full size big buck hunter, games or oversized couch and big screen tv!

~Pearl Cottage~

1930’s French cottage for an ADULT ONLY, NO WORK CREWS get away. The coffee-breakfast size kitchen is tiny. features vintage dishes, 30’s silverware and crystal bar service. NOTE: dinning room and kitchen are tiny. The down sofa and working fireplace make the living room a relaxing place to unwind. Bedrooms furnished with velvet headboards from Anthropology, down bedding for a luxurious nights sleep. 4 blocks from the Round Up grounds, parking included. NO children under 13. No pets.

NEW! 2 Kings/Hot Tub/Access to Full Gym/Espresso!

Sage Haven: a modern, newly remodeled home designed to provide you with a peaceful and relaxing get-away. Whether you’re here for the world famous Round-up, Whiskey Fest, a restful retreat with friends or family, work travel, or a family vacation, you will find that this home will serve all your needs. Located at the base of the Blues, you are just minutes from tranquil nature or exciting downtown activities. Message me to learn about short/long-term discounts for you and pets!

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.

Deal Canyon Ranch House

This quaint cabin feels like you are a million miles from civilization, situated just 3 minutes from town. The cabin sits on 22 acres, and butts up to a large cattle ranch. The view of La Grande is breathtaking. Sit on the deck in the morning & sip your coffee while listening to the sounds of the creek. A hiking trail is right outside the front door., or stay in & enjoy the hot tub! Your stay can be packed with outdoor adventures or be as relaxing as you wish.

Private Creekside Farm Stay near Walla Walla

Welcome to your quiet farm escape in Oregon 🌾 Enjoy a peaceful stay on a working farm with wheat fields, cattle, vineyard, and the calming sounds of Couse Creek nearby. Surrounded by open land, wildlife, and mountain view, this is a true escape with total privacy—no neighbors. Located just 3 miles from Milton-Freewater and 10 miles from Walla Walla wine country. Perfect for a quiet getaway, wine tasting trip, or a relaxing break in nature.

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.

La Casita at Castillo de Feliciana-Winery on site

If privacy is what you're looking for, this cute little casita is tucked away in the vineyards of Castillo de Feliciana! Enjoy the peace and quiet of the Walla Walla countryside inside this large 1 bed, 2 bath oasis! Features include a full kitchen, with a gas stove and dining area, large Smart TV, a gas fireplace, a large step-in shower, a beautiful soaking tub, and a gorgeous patio/outdoor eating area, to name a few.

A Mile From Historic Downtown + Free Breakfast

Hampton Inn Pendleton offers a convenient stay just off I‑84 and one mile from historic downtown. Explore the famous Pendleton Underground Tour, visit the Pendleton Round‑Up grounds, or enjoy golf, entertainment, and gaming at Wildhorse Resort & Casino just minutes away. Relax with free hot breakfast, complimentary WiFi, and comfortable amenities for an easy, welcoming stay in Pendleton.

3-bedroom home in quiet Milton with Hot tub!

Forget your worries in this spacious and serene space. Nestled in the charming town of Milton Freewater, this bright and comfortable house offers everything you need for a memorable stay. With 3 bedrooms, 3 bathrooms, and around 1,600 square feet of living space, it's ideal for families, friends, or anyone looking for a peaceful retreat.