Cottage holiday rentals in Eastern Oregon

The Red Door Cottage. 10% off for volunteer FD

Enjoy the quintessential Eastern Oregon experience in this beautifully restored 1909 cottage. Private, elegant and super cozy in the heart of historic Sumpter Oregon. Hiking, biking, fishing, quad riding and exceptional mushroom and huckleberry picking basically any outdoor activity you can think of! Our house features two bedrooms with queen beds, full bathroom a Hideaway sofa bed, full kitchen, TV with DVDs & more. Amazing outdoor area where you can grill some delicious food, relax and enjoy!

Modern Cottage 'D'

Enjoy a stylish experience at this centrally-located cottage home. Modern style, Cottage 'D' is a 480 sq ft home that sits right in the heart of La Grande. New construction with full kitchen, stainless appliances, microwave, Keurig coffee maker, iron, and washer & dryer. Located on a beautiful property with mountain views located steps from Grande Ronde Hospital , Eastern Oregon University and blocks from Downtown La Grande. Cottage 'D' is one of three Cottages available at this location.

The Blackberry Cottage

This adorable 1950's cottage is located in the heart of Midtown Bend, within walking distance to local coffee shops, restaurants, parks and Pilot Butte State Park, and less than a mile away from downtown Bend. Two light-filled bedrooms both have double French doors leading out to a large back deck and a fenced, private backyard. A cozy living room, and eat in kitchen make this home the perfect place for a small family or a few friends to share. Serene fenced back yard space with hot tub.

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!

Classic Cottage in the Heart of Baker City

Just a short walk from all of the happenings downtown, this comfortable three-bedroom cottage is the ideal home base while visiting Baker! The third bedroom is in the finished basement. And, as a bonus, there are two twin beds in the Airstream available, in case you decide to be adventurous while enjoying this unique amenity! When back at the house you will want to use the hot tub, just off the large deck, where the evening can be spent relaxing in a back yard designed for entertainment!

The Baker City Jewel Box- A Dog Friendly Art House

South Baker 1910 super cozy cottage, perfect for two. Original art & color abound, many guests just want to move in & stay long term. Info on local sights, restaurants & things to do are on site so it's perfect for Basecamp Baker adventures or enjoying the secure pup friendly yard. Gated parking for 1-2 cars & plenty more off street out front. Queen bed, comfy living room, kitchen, bath & laundry, streaming wi-fi & Netflix-it's a gem! If booked see Old Mill House- same but different.

Blossom Cottage Studio

Keep it simple and take it easy at this peaceful and centrally-located, unique, cozy getaway. The Blossom Cottage Studio is located in a beautiful garden setting. ~The space~ • One Room Studio • 1 Bathroom • Full sized bed (additional cot if needed) •Kitchenette (Refrigerator w/small Freezer, Toaster Oven, Microwave, Blender, Kuerig, etc) •Short walk to the heart of downtown Redmond. The cottage is private and located on the back property of a Gift Boutique Shop and Bakery/Cafe.

The Cottage - Your Adventure Headquarters!

Whether you are looking for a backcountry experience or the slow pace of a small town, you’ll come home to a hot shower and fresh linens, a fully-equipped kitchen and 815 sq ft. of cozy charm. Our goal is to make your stay easy and care-free so you can get out and enjoy your adventures! Wifi, ceiling fans, on-demand water heating and A/C will add comfort and convenience to your stay, along with a heated mudroom for outdoor gear that is equipped with a full-size washer and dryer.

Blue Spruce Cottage, 2/1, Modern, & Clean.

This cottage is located in the heart of Midtown - 20 mIn walk downtown & walking minutes from great food/beer/coffee. You will enjoy a very quiet, newer home, with air conditioning & 2 KING tempurpedic beds, tucked under mature Spruce trees. For active guests a hose is available to wash bikes, washer/drier and indoor racks to dry your clothing. A full kitchen and BBQ for meal prep. Garage is secure and available UPON REQUEST. Lastly, wireless internet is super fast, 300mbs.

Little House on High Prairie

Escape to the quiet beauty of High Prairie on this 40-acre farm with wide-open skies and stunning mountain views. Cozy and private, this guest space is ideal for anyone looking to relax, unplug, and enjoy a slower pace of life. Surrounded by horses, sheep, chickens, goats, barn cats and more, you'll experience authentic farm charm while still being a short drive to the Columbia River Gorge’s hikes and attractions. Please note: no pets allowed to ensure a peaceful stay for all.

Century Farm Charm at the Century Pine Cottage

Century Pine Cottage is located on the historic McKenzie Century Farm providing modern lodging comfort in a peaceful and scenic rural setting close to all northeast Oregon has to offer. Twelve miles from La Grande and within an hour of Eagle Cap Wilderness, historic Pendleton and Baker City, Walla Walla wine country and so much more. Use as a base or sit and enjoy bird and wildlife viewing, or a good book and the scenic backdrop of the northern Grande Ronde Valley.

Cheerful Cottage Pet Friendly Close to Downtown

You (and your furry friend) will be close to everything when you stay at this centrally-located house in historic 'Depot Bench'. The cottage is only minutes from Boise State University and Downtown and features super Fast Wifi, a cozy bed, a relaxing living room, and a kitchen with everything you need to cook at home. Includes smart T.V., keyless entry, washer/dryer. Pet friendly with pet fee of $25/night. Please contact me for longer stay pricing.