Holiday rentals with a fireplace near Old Mill District

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.

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.

Location! 4-Bedroom, 3-bath Downtown w/Hottub

Lovely updated 4 bedroom, 3 full-bath home located in historical district 3 1/2 blocks to both downtown Bend, Riverfront and the Old Mill District. Located right across the street from a Brewery, Starbucks and the best store in Bend, Market of Choice. Pet Friendly - with additional fees. Mt. Bachelor view from large hot-tub in backyard. Main bedroom has private entrance, kitchenette, luxury bathroom and and spacious private back deck . 20-minute drive to Mt. Bachelor.

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!

Dog Ok | 8 min to Old Mill | EV Charger| Near Park

Beautiful 3 Bedroom plus Kids Room/Den Home! Located in SE Bend, just minutes to Downtown. Brand New listing with designer furnishing. Backs up onto a large open space with some of the best hiking and biking trails in Bend out the back and close by! EV Charger in the garage free for your use! Peloton in the Laundry Room to keep up your fitness! Bring your bikes and ski gear and enjoy the best of Bend!

Haven’s Nest | Walk to Old Mill / Deschutes River

Welcome to Haven’s Nest, a peaceful Bend getaway perfectly located near the Deschutes River trails and an easy walk to the Old Mill District. Start your mornings with coffee and fresh mountain air, then stroll to the river, bike scenic trails, or enjoy local shops and dining just minutes away. Thoughtfully designed for comfort, privacy, and relaxation—this is your ideal home base for exploring Bend.

River Camp House

The perfect getaway for the outdoor enthusiast and for local entertainment in this ultra clean Bend home. Hop on the trails from the doorstep of this riverside home. Rustic tables, wooden floors, and a central fire place lend to the warm, cabin ambiance. Relax on the patio by the fire pit perfect for roasting marshmallows after a full day on the slopes.