Holiday rentals with a fireplace in Bend

Cozy Three Story Lookout Tower

Thank you for your interest in The Cozy Lookout Tower! Our unique vacation home is really a destination location rather than just a place to stay while you explore the area. Many of our guests are repeat guests that use our home as a place to recharge, relax, cook, read, talk, play games and connect with that special someone. There are some lovely hikes in the area, we encourage you to bring your dog and enjoy the beautiful surroundings by taking some hikes then returning for a soak in the tub!

| The Chalet | 1+ acre| Remodeled | Quiet |

Discover tranquility in our A-frame cabin nestled among the pines. A rustic haven where the scent of pine fills the air, inviting you to unwind on the porch. Inside, a cozy living space & quaint kitchen offer comfort. Retreat to the loft bedroom, where the soft glow of morning light through pine branches awaits. Whether a romantic escape or family adventure, this cabin is a sanctuary, a respite from the daily rush. Embrace simplicity, enjoy the peace & quiet, and enjoy all the nearby beauty.

Welcome to Dome Sweet Dome

Your chance to stay in a true-to-name Geodesic Dome! This one-of-a-kind retreat blends comfort with architectural charm. Guests call it cozy, inspiring, and unforgettable — a stay that feels like an experience, not just a place to sleep. Nestled in the First-on-the-Hill neighborhood off Century Drive, the Dome is perfectly positioned for everything Bend has to offer. Whether you’re here for skiing, biking, hiking, or just relaxing, you’ll love how close you are to Bend’s best adventures.

Rooftop Deck! Walk to Town+Fun Trails & Fire Pit

Enjoy the private rooftop deck with gas fire pit and wet bar. After a day of activities relax in the custom soaking tub. Relax in this multi-level luxurious townhouse. 2 minute walk to the Deschutes River Trail and 10 minute walk to downtown Bend. Walkable to local breweries, shops , and restaurants. Enjoy a meal with your friends or family cooking in our gourmet Chef's Kitchen. Safely store your bikes and ski gear in the 2 car garage. FAST Wi-fi - Perfect for remote working.

Sixties Suite Spot

Escape to our cozy, retro suite, a serene haven centrally located near Pine Nursery Park. Enjoy a tranquil retreat with high-quality amenities, dog-friendly comforts, and snowboard/ski storage. With a semi-private yard featuring Adirondack chairs, easy parking, and a vibrant, photo-ready design, it's perfect for relaxation and adventure. We proudly welcome 2SLGBTQIA+ guests, offering a warm, inclusive environment. Discover a blend of charm and convenience at our unique getaway!

Airy Bend Oasis - Two Ensuites

Cheers to your stay at Bent Pine Oasis, located in the picturesque west side of Bend! This home provides the ideal location for any outdoor enthusiast: Mt Bachelor's slopes are just a 20 minute drive & the Deschutes River Trail is mere steps from the front door- your avenue to biking, running and exploring Bend. Looking for a more relaxing day? You can make the 5 minute drive into the Old Mill District to enjoy food trucks, a river float, or fresh hops at a local brewery.

Drake Park Walk Everywhere Ski Wk Nt Special 250!

Twin Elms is a newer, 3-level home nestled between two great elms. Located in a quiet historic neighborhood,..,a short walk to Drake Park, Deschutes River, Old Mill, breweries, restaurants & fabulous downtown Bend! There's 3 bedrooms, 3 full baths & a sleeping nook (2 twin XL beds) in the den. The Master Suite has a jetted spa tub. You'll love the big 2 car garage for safely keeping your gear! We are here & happy to help with all your needs! twinelmsbend dot com

Old Mill Charm

Great Location in Old Mill District – Walk to Summer Concerts! ♥ Fenced Backyard ♥ Pet Friendly Nestled in the heart of Bend, Old Mill Charm offers the perfect blend of comfort and convenience. Thoughtfully designed with many amenities to ensure a seamless stay, this charming rental is ideal for relaxing or exploring all that Bend has to offer. There is a tenant in the apartment above the detached garage who does not use the driveway ensuring your privacy.

"Urban Spruce" - Great peaceful location!!

Newly renovated 1940 Classic! Located just steps away from the center of town and all the shops and restaurants that Bend has to offer. Our home consists of the 2 bedroom "Urban Spruce" and a separate one bedroom lower unit "The Downtowner". Located under a magnificent Blue Spruce tree on a surprisingly quiet street, this combination of location, serenity, and quality of craftsmanship make for an exceptional destination option!

Adorable West Side Cottage, Pet Friendly!

Enjoy a cozy and comfortable stay in my 1-bedroom, 2-bathroom home, complete with a bonus room that offers plenty of privacy when needed and a plush futon that allows for two additional guests (best for up to 3 adults or 2 adults and 2 kids, or two couples would work as a well ) Conveniently located within walking distance of Newport Market, Backporch Coffee, Chow, and Spork, it's just five blocks from downtown

Cozy Home w/River Access, Hot Tub, 7min to Village

Welcome to our Backcountry Basecamp Cottage! Nestled in the heart of the Deschutes National Forest. Our home is a short walk from the crystal-clear waters of the Deschutes River, which you can access through a private neighborhood marina. You can enjoy hiking, floating, kayaking, or skiing and snowshoeing nearby. It is the perfect base camp for exploring all that the area has to offer.

Guest suite | Hot tub & sauna Cabin in the Woods

Private guest suite in our newly built home, just steps from a cabin-style spa with a hot tub and infrared sauna. Relax in the peaceful forested backyard, enjoy high-speed 300 Mbps Wi-Fi, and watch starry skies. A campfire to unwind, a sunset to inspire, and the Milky Way framed by towering Ponderosa pines — this place is the perfect blend of modern comfort and nature’s beauty.