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!

Laverne - Historic Home in Downtown (new hot tub!)

Laverne is a one bedroom historic cottage tucked in between two larger houses, with access from both Georgia Ave and Lava Road. Unique for it's proximity to downtown AND the peaceful residential feel. Mature landscaping with heritage cherry tree, private and sheltered bungalow. Outdoor space includes private deck and hot tub with views; small enclosed front yard. Full kitchen, washer/dryer. Queen Casper in the tiny bedroom. Sleeper sofa in living room. Great natural light. Off street parking.

Elegant Second-Floor Condo Near Downtown Bend

This newly remodeled one-bedroom unit at Pioneer Park Condos offers an unparalleled locale next to the Deschutes River Spillway and Pioneer Park. Downtown is within walking distance and offers a plethora of restaurants and local boutiques to shop! This condo sleeps up to 4 vacationers comfortably. This owner has also left his gym membership to Juniper Fitness here for his guest to use! You will have access to the gym equipment, the sauna areas, the pool they have there, plus much much more!

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.

Craftsman Style Retreat in Bend River West

Located in one of Bend’s most walkable neighborhoods, this studio is a couple blocks away from Columbia Park with easy walking access to Drake Park, Harmon Park, McKay Park and the Old Mill District (and amphitheater). After (or before) you’ve explored nearby shopping and food, head out and explore the endless outdoor activities such as skiing, Mt. Biking, rafting, fishing, and much more! You are short pedal to Phils Trails, a 5 min walk to Mt. Bachelor’s Park n Ride (or 25 min. drive).

Mountain Bliss: Gateway to Mt. Bachelor and More

When the mountains are calling, Bend is like nothing on earth. Savor the charms of Base Camp throughout the year in this luxurious and spacious cabin (1200 square feet). Celebrate the great outdoors – best experienced through unparalleled adventures at Mt. Bachelor (18 miles), Phil’s trailhead (15 minutes), the Deschutes River (5 minutes) as well as the endless access to hiking, biking, running trails, skiing, golf, breweries, restaurants, coffee shops, and the Hayden Homes Amphitheater.

Black Duck Cabin

Cozy A frame cabin set in a quiet neighborhood among the pine trees just a short walk from the Deschutes River. The Black Duck Cabin is a perfect destination for all of Central Oregon's amazing activities. 10 minute drive to Sunriver Village, 30 minute drive to Mt. Bachelor, 30 minutes to Downtown Bend, 10 minute walk to the Deschutes River, golfing, fishing, hiking, shopping, mountain biking, all a short drive. If you're looking for a rustic, cabin experience this is the place for you!

Have a Patio Barbecue at a Pet-Friendly House in Midtown

Stoke the wood stove with another log and stay warm and cozy in a colorful plant-filled living room with stylish mid-century modern furniture. When the weather's nice, go outside to play croquet or corn toss and roast mores around the fire pit under the stars. Each bedroom has cable TV....large fully fenced in yard . Dogs are welcome. Limit of 3 with a $35.00 Pet fee. No cats allowed. Wood provided. There is a smart lock on the front door, you will be given the code before arrival.

The Nook Near the Old Mill - Sauna

Relax in a beautifully remodeled 1930s mill house featuring a full kitchen, fireplace, landscaped yard, and a genuine Finnish-style sauna. Located just 3 minutes from the Old Mill District with easy Hwy 97 access, yet tucked into a quiet neighborhood. Enjoy a peaceful yard with native plants and a fire table for Central Oregon evenings. A small private backyard is perfect for cooling off after the sauna. Pet-free and cleaned with unscented products for a fresh, allergen-free stay.

Bend Mid-Century Getaway• Near Old Mill & Downtown

Nestled in a quiet, friendly neighborhood on a private street, this cherished 4BR retreat has been carefully curated, with each item lovingly woven into the gorgeously designed interior. Sun-filled spaces feature a cozy fireplace, gourmet kitchen, and fun extras like shuffleboard and a foosball table. Evenings invite you to gather on the patio with BBQ and fire pit. Minutes from Bend’s Old Mill, river, trails, and Mt. Bachelor, it’s peaceful yet perfectly connected.

"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!

Vintage Pink Hot Tub✓ Walkable✓

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 with shower and bathtub (which requires adequate mobility) and wood floors. Comforts include: Hot Tub, Gas fireplace, Dishwasher, W/D.