Welcome to Oregon! Whether you're heading for the scenic hamlets of the Oregon coast or the hip, happening, city of Portland, RedAwning has the cottage, cabin, home or apartment to make your trip comfortable. Use the blue location links below to browse and explore Oregon's most popular regions, or filter your vacation home preferences using the panel to the side. RedAwning offers instant, hotel-style reservations and a simplified booking process so you can have your travel plans zipped up in no time.

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  1. HOUSE
    Family Fun at Black Butte Ranch 3BR

    Family Fun at Black Butte Ranch 3BR

    Black Butte Ranch, OR

    Nestled in the pines of Black Butte Ranch, this winning 3BR/2BA home accommodates eight guests. Comfy furniture, warm wood details, and a cozy wood stove await your arrival. Enjoy entertainment amenities such as ping-pong, darts, and a canoe. The...

    Pool Hot Tub
    FREE CANCELLATION

    $156 to $428/night

  2. CONDOMINIUM
    Rooftop Deck, Golf Course View & 6 SHARC Passes

    Rooftop Deck, Golf Course View & 6 SHARC Passes

    Bend, OR

    This 1,368 square foot 2BR/2BA townhome offers one of the best locations in Sunriver, quietly tucked away on a peaceful wooded lot. Soak up the sun on the rooftop deck, and dine alfresco on the covered balcony with golf course views. When you want...

    FREE CANCELLATION

    $282 to $440/night

  3. HOUSE
    3BR w/ Hot Tub & Rec Passes

    3BR w/ Hot Tub & Rec Passes

    Bend, OR

    Just minutes from the Oregon Observatory and Sunriver Nature Center, this remodeled 3BR/2BA home offers the ultimate nature retreat. Boasting one of the best locations in Sunriver, you’ll love being within walking distance of 33 beautiful paved...

    Hot Tub
    FREE CANCELLATION

    $145 to $471/night

  4. CONDOMINIUM
    Golf Course 3BR w/ Private Hot Tub

    Golf Course 3BR w/ Private Hot Tub

    Redmond, OR

    A sophisticated golf vacation for six awaits at this 3BR/2BA condo at Eagle Crest Resort. Take in sweeping views of the fairway from the living room, second-floor master suite, or from the private open-air hot tub on the deck. Find high-end...

    Pool Hot Tub Pets OK
    FREE CANCELLATION

    $137 to $317/night

  5. HOUSE
    5BR w/ Hot Tub on 5-Acre Lot

    5BR w/ Hot Tub on 5-Acre Lot

    Sisters, OR

    Plan a delightful multi-family getaway to this 5BR/3.5BA rental for 13 guests. With a spacious kitchen and dining area and two living rooms, there’s plenty of room to spread out. Situated just 3 miles from the heart of Sisters on a five-acre...

    Hot Tub
    FREE CANCELLATION

    $202 to $485/night

  6. CONDOMINIUM
    Serene 2BR w/ Pool & Hot Tub

    Serene 2BR w/ Pool & Hot Tub

    Bend, OR

    This 2BR condo offers a peaceful getaway with easy access to year-round activities. The welcoming first-floor unit features hardwood floors, new furnishings, and a private patio. On-site amenities include a seasonal heated pool and hot tub....

    Pool Hot Tub
    FREE CANCELLATION

    $111 to $369/night

  7. HOUSE
    3BR w/ Large Fenced Yard & Deck

    3BR w/ Large Fenced Yard & Deck

    Bend, OR

    PROPERTY OVERVIEW Beautifully updated and comfortably furnished, this single-story 3BR/2BA getaway allows you to make the most of your time in Bend. Prepare tasty home-cooked meals in a gourmet kitchen, and relax in the spacious fenced yard or on...

    FREE CANCELLATION

    $139 to $469/night

  8. HOUSE
    3BR w/ Sauna, Hot Tub & Home Theater

    3BR w/ Sauna, Hot Tub & Home Theater

    Bend, OR

    PROPERTY OVERVIEW Situated on a tranquil half-acre of land, this 3BR/3BA Westside Bend home boasts quick and convenient access to breathtaking natural beauty. Hop on the provided bicycles and explore the nearby hiking/biking trails and the river --...

    Hot Tub Pets OK
    FREE CANCELLATION

    $134 to $571/night

  9. HOUSE
    Massive 5BR on Golf Course w/ Hot Tub

    Massive 5BR on Golf Course w/ Hot Tub

    Bend, OR

    With an ultra-spacious floor plan and crowd-pleasing perks, this 5BR/5.5BA Sunriver home is perfect for a big group getaway! The house overlooks the second fairway at Woodlands Golf Course, and boasts an array of amenities, including a pool table,...

    Pool Hot Tub
    FREE CANCELLATION

    $632 to $1,783/night

  10. HOUSE
    New Listing! Bend Basecamp w/ Hot Tub, Fenced Yard

    New Listing! Bend Basecamp w/ Hot Tub, Fenced Yard

    Bend, OR

    ** This brand-new listing may not have an abundance of guest reviews yet, but you can be assured of an exceptional stay. Thoroughly vetted, this home is professionally managed by TurnKey Vacation Rentals, two-time winner of the Travel Weekly...

    Hot Tub Pets OK
    FREE CANCELLATION

    $177 to $350/night

  11. HOUSE
    2BR w/ Riverfront Spa & Fire Pit

    2BR w/ Riverfront Spa & Fire Pit

    Bend, OR

    Experience the beauty of Bend in this recently remodeled riverfront 2BR/2BA home. Enjoy idyllic views of the Deschutes River from the comfort of your outdoor hot tub and patio. Hold a movie night in the charming living room, with plush seating, a...

    Hot Tub
    FREE CANCELLATION

    $166 to $611/night

  12. HOUSE
    Quiet 4BR w/ Private Hot Tub & Deck

    Quiet 4BR w/ Private Hot Tub & Deck

    Bend, OR

    This appealing 4BR/2BA home sits in a quiet Sunriver neighborhood minutes from Fort Rock Park. Enjoy complimentary passes to the Sunriver Aquatic & Recreation Center, an all-season center that offers indoor and outdoor aquatics, a disc golf course,...

    Pool Hot Tub Pets OK
    FREE CANCELLATION

    $203 to $485/night

  13. HOUSE
    "Otterhouse"- Big 2BR Riverfront w/ Kayaks

    "Otterhouse"- Big 2BR Riverfront w/ Kayaks

    Bend, OR

    Affectionately known as the Otterhouse, this 2BR/2BA getaway brings you close to nature, while being within easy driving distance of Sunriver Village, Bend, and Mt. Bachelor. This two-story chalet features three inviting living areas. Outside,...

    Pets OK
    FREE CANCELLATION

    $203 to $402/night

  14. HOUSE
    4BR w/ Hot Tub & Foosball, 200’ to Deschutes River

    4BR w/ Hot Tub & Foosball, 200’ to Deschutes River...

    Bend, OR

    Steps from the Deschutes River and Cardinal Landing Bridge, this exceptional 4BR/3.5BA home boasts a private hot tub, two decks, an inviting Great Room. Enjoy access to Sunriver's Aquatics Center, complete with multiple pools and a lazy river....

    Pool Hot Tub Pets OK
    FREE CANCELLATION

    $446 to $767/night

  15. CONDOMINIUM
    3BR w/ Hot Tub & Aquatic Park Passes-- Near River

    3BR w/ Hot Tub & Aquatic Park Passes-- Near River

    Bend, OR

    Split across two levels, this inviting 3BR/2.5BA condo in Sunriver is located on Sunriver’s north end, putting you within close proximity to a host of local attractions. Meadows Golf Course, Sunriver Tennis, and the Deschutes River are all...

    Pool Hot Tub
    FREE CANCELLATION

    $169 to $373/night

  16. HOUSE
    3BR w/ Hot Tub & Multi-level Deck

    3BR w/ Hot Tub & Multi-level Deck

    Bend, OR

    Nestled in picturesque Sunriver, this pet-friendly 3BR/2BA is a nature lover’s dream. Highlights of this updated cabin-style home include rustic-chic decor, wood paneling, and cathedral ceilings offering loads of natural light. Take in gorgeous...

    Pool Hot Tub Pets OK
    FREE CANCELLATION

    $151 to $358/night

  17. TOWNHOUSE
    All-Suite 3BR w/ Private Hot Tub

    All-Suite 3BR w/ Private Hot Tub

    Bend, OR

    Experience the laid-back mountain lifestyle at this private all-suite 3BR/3.5BA townhome. Create vacation memories in the grand living space that features vaulted ceilings, a gas fireplace, ski artwork, and tasteful décor. Tall windows provide...

    Hot Tub
    FREE CANCELLATION

    $254 to $495/night

  18. CONDOMINIUM
    3BR w/ Private Hot Tub & Gorgeous Creek Views

    3BR w/ Private Hot Tub & Gorgeous Creek Views

    Redmond, OR

    You’ll love the tranquility of this 3BR/2.5BA home in Redmond, offering a secluded setting overlooking the creek in Eagle Crest Resort. Enjoy the views from your expansive deck, featuring a private hot tub and stairs that lead to a walking path...

    Pool Hot Tub
    FREE CANCELLATION

    $169 to $358/night