Cottage holiday rentals in Eastern Oregon

NW Bend Hot Tub+Big Porch w/ Enclosed Yard+Pets OK

Located in the heart of NW Bend in the middle of it all! A short walk to great restaurants + pubs, the river, Amphitheater, Downtown, 3 Parks, The Old Mill -but on a nice quiet street. Well worth the price, it sleeps a comfortable 4 and a cozy 6 with a comfty Queen bed in one room, and pine bunk bed in other room (full bed on bottom and top with cozy mattresses). Large enclosed yard for the pets and patio with Hot tub! The home is well stocked, tastefully furnished with high quality bedding.

Travelers Studio Cottage, Dog Friendly

This special place is close to everything, making it easy to plan your visit. Originally built in 1900, this newly updated studio cottage is comfortably furnished and stocked with all the essentials. With a king size DreamCloud bed and a full size sofa sleeper it can accommodate up to 4 people. Conveniently located within blocks of downtown, Leo Adler Pathway, city park, and shopping. The dog bed and toys, along with the large fenced back yard are sure to make your pooch feel right at home too!

Vintage Pink Hot Tub✓ Walkable✓

NOTE: Thru June ongoing road construction is scheduled on Portland Ave. Please read Other Things to Note below before booking :-) Our 105 year-old lovingly restored 1920 cottage is 3 blocks from First Street River Rapids, 25 minutes to Bachelor & 10 minute walk to Town. Centrally located urban setting on a main street. Step back in time, the original charm was painstakingly preserved, with original claw foot bathtub, wood floors. Comforts include: Hot Tub, Gas fireplace, Dishwasher, W/D.

River Haven Cottage

This is a cute little cottage built in the 1930's on the Williamson River. Down river, there are trout in it for fishing, catch and release only, anyone over 12 must have a license to fish. The deck at the back of the house is partially covered. The river is also great for playing, swimming (a little cold in spring) and for kayaking. There is a kayak rental store in town. The air is usually warm, 70's & 80's, on summer afternoons. There are stairs to enter the cottage. Great place to relax.

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!

“Peaceful Pines Cottage” 2+ acres near Mt. Bach

Peaceful Pines Cottage is a newly renovated PET FRIENDLY remote cottage located in Central Oregon. Perfect for ski trips at Mt. Bachelor & Willamette Ski Resort! This 3 bedroom / 2 full bathroom home is on 2.25 acres of fully fenced-in land that backs up to public BLM land for you to explore.. Driving distance to downtown La Pine, Bend, PCT trails, Crater Lake National Park, lakes + much more! This is the perfect home for a gathering with loved ones or a relaxing weekend for yourself.

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.

Depot Bench Cottage

Newly renovated, private cottage with sunny patio in the charming Depot Bench neighborhood. Easy access to downtown, BSU & the Greenbelt. Boise's historic train depot is just a short walk away where you can lounge in the gardens and enjoy sunsets overlooking the city. Additionally the ever popular James Beard Nominated chefs at "White Rabbit" are in the neighborhood! Perfect getaway for a weekend away and convenient for a longer stay!

Historic Downtown, Private Hot Tub, High Demand

This amazing little downtown cottage provides all the comforts of home with the freedoms of vacationing. You cannot find a better location than The Autumn Cottage! It is located on a quiet little street, yet it is just one block from the historic downtown area. It has been lovingly designed to offer guests the full flavor of Bend, with many modern amenities paired with classic charm to make your Bend visit exceptional.