Pet-friendly holiday rentals in Wallowa County

Joseph Cottage: Mountain Views, Fireplace, Firepit

Wake up to sweeping Wallowa Mountain views, sip coffee on the sunny deck, and unwind by the fire under star-filled skies. Just 3 blocks from downtown and minutes to Wallowa Lake, this charming cottage is the perfect home base for your Joseph getaway. Designed for comfort and connection, Serendipity Cottage offers a cozy fireplace, a fully equipped kitchen, and a spacious fenced yard—perfect for relaxing after a day of hiking, exploring, or lake adventures. You and your pup will love it here!

Almosta Farm Bungalow near La Grande, Sleeps 4

Enjoy stunning sunsets from your private studio bungalow nestled at the base of Mount Fanny in historic Cove, Oregon. Located 10 miles from Union, Oregon and 15 miles from La Grande, Oregon on the Cove-Union Farm Route. We are near mountain biking and hiking & 30 minutes from Moss Spring Trail head (Minam Lodge). We are an hour away from Anthony Lakes and 90 minutes from Jospeh. The studio will sleep up to 4 people if a second bed is requested. Ask about teacher discount. Gay friendly

The Aspen

A unique stay in the heart of Downtown Joseph, conveniently located behind Arrowhead Chocolates, Coffee & Tea cafe. Walking distance to all the local shops and restaurants, and only 2 miles to beautiful Wallowa Lake. Our cozy space is pet friendly, equipped with high-speed WiFi, A spacious lounge area, kitchenette, propane fireplace, and air-conditioning. Let this cozy location be your home base for adventuring in the Eagle Caps, fishing, hiking, and exploring the stunning town of Joseph.

Creekside, Great Views, In Heart of Downtown

The Red Horse Retreat in downtown Joseph was once a a local's favorite cafe and coffee shop that has since been transformed into a bright and charming vacation home in the heart of downtown Joseph. The Red Horse now features two large living areas, expansive decks next to the creek with great views of the Wallowa Mountains , an "almost full" kitchen, and sleeping for six guests with a king, queen and double bed. You'll love the bright spaces, the charming touches, and the awesome location.

The Country House

Glorious inside & rugged outside - 3500 sq. ft of living space on 45 wild acres. This pet friendly house offers wonderful views of the Elkhorns & time away from the busyness of life. 5 miles to Thief Valley Reservoir and 23miles to Anthony Lakes Ski Resort. This house is located between North Powder and Union. When we say Country, we mean it -new and old farm equipment, woodshed, wild plants & animals, bugs, dirt with mud & dust. *No WiFi *Train can block road to house whenever it wants

Cherry Orchard Cottage

Relax at this brand-new cottage nestled among cherry trees against the Wallowa Mountain range. Enjoy the views of the beautiful Grande Ronde valley as you unwind on the deck watching the sun set. The cottage is located outside the city limits in the cute little town of Cove. Gateway to many outdoor activities, hiking, biking, and skiing. Eastern Oregon University (La Grande) 17 miles, Anthony Lake 47 miles, Wallowa Lake 84 miles, Moss Springs trail head 11 miles (Minam Lodge).

Unique log cabin in DT Joseph OR

This memorable place is anything but ordinary. Once an art gallery, it was empty for years until a unique organization took over the space. Cross the Divide serves our nation’s veterans by providing adventures in our beautiful county. This home is now ready to give YOU that same experience! Set in town, the home boasts living and dining areas as well as a common area including 4 beds (one queen and 3 singles), TV, couch and a chair. Joseph is just steps outside the door!

Cheerful 4 bedroom farmhouse with fire pit

Jones Farmhouse is located on a working farm that has been in our family for 40 years. Comfy and spacious this unique listing will give you great family trip memories. The front deck mountain views are hard to beat, and will create cozy and fun times. Jones Farmhouse is located 3 miles from Enterprise and 3 miles from Joseph on a quiet country road. Backyard venue available for up to 100 people for additional cost. {Weddings possible) Please private message for details.

Golden Saddle lakefront log home-Wallowa Lake

The Golden Saddle is a stunning custom log home on Wallowa Lake’s west side—perfect for families or couples. Sleeps 10 with 4BR/3BA, a main-level king suite (jacuzzi tub), coffee bar and lake-view deck with private dock (seasonal). Enjoy the stone fireplace, pool table, and flatscreen TVs. Features Wi-Fi, washer/dryer, and parking for 3m Pet friendly—your ideal lakeside retreat! ( 4WD/chains/traction tires **STRONGLY** recommended in winter-we'd require them if we could!)

#50-A frame cabin with private hot tub/sauna/lake

Our cozy a frame cabin has loads of appeal with large windows facing Wallowa Lake! Enjoy the views from inside or from the deck/sauna/hot tub that all overlook Wallowa Lake! Comfortable, charming, vintage cabin that has been updated and remodeled to have modern conveniences while maintaining the cozy feel of an a frame. A very popular vacation destination at Wallowa Lake! Perfect cabin for a family, friends or for a romantic weekend with your sweetie!

Troy, Oregon log cabin - not in Enterprise

My Troy, Oregon log cabin (not in Enterprise), has two bedrooms (one in the loft), a kitchen, laundry, porch, and outdoor space for tents, games, kids and dogs. Private access to the Wenaha River around behind the cabin. The Grande Ronde river is a short walk away. Morels and wildflowers in May. Floating in June & July. Huckleberries in July/Aug. Fishing year-round, Steelhead season begins Sept 1. Stay 3+ nights, rate changes to $150/night. Just ask.

#26-Cozy home in the pines @ resortside Wallowa Lk

Tucked off the road the driveway is easy to miss which is our favorite part of the home! Situated among the trees, on a little stream, private and relaxing are two words often used to describe our cabin! This home is perfect for the adventurers, the small families, the reconnecting couples! Close enough to walk to the resort side activities at Wallowa Lake but tucked back for privacy, relaxation and enjoyment of being in the woods!