Holiday rentals with a fireplace near Old Mill District

Historic Downtown, Private Hot Tub, High Demand

NOTE: Intermittent area construction August 4-8 with discounted rates! 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.

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.

Salmon Lodge Luxury 3BR Bend OR Old Mill District

The Salmon Lodge is a West Bend luxury 3 BR 3 Bath townhome in the Old Mill District. It has served as a premier vacation rental for the last decade. Under new ownership since 2022, we are excited to honor the legacy of the thoughtfully built Salmon Lodge. We will continue to offer the quintessential Bend experience. Walk or bike everywhere! Close to Old Mill shopping, downtown, Mt Bachelor, Deschutes & concert venue. Mountain view from upstairs deck with attached bar. Sleeps 8 to 9

Modern high-end home, walk downtown

This fantastic modern home is in the sweet spot of Bend...just next door to the Deschutes River, Downtown Bend, parks, restaurants and dining, nightlife, and family-friendly activities. You'll love our home because of the amazing location, the mid-century inspired ambiance, the high ceilings, the people, and the local views. We are the perfect centrally located home for any Bend adventure. Our place is great for couples and solo adventurers. This is not a party house. Sorry no pets.

Sunny Getaway: fenced | Near trails, dining, music

This inviting, relaxing, cottage is just minutes from great dining, shopping & trails in SE Bend’s Larkspur neighborhood. Enjoy the deck, fire pit, BBQ, fenced yard, fast WiFi and washer/dryer. Stroll the Deschutes River, explore bike trails, and enjoy quick access to downtown and shops at the Old Mill District! Visit Bend’s brunch scene or stay in and cook up waffles in the stocked kitchen. Book the Stadium Bungalow as your perfect basecamp for exploring Bend year-round!

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.

Westside "Bud-And- Breakfast"

The first and only "Bud-And-Breakfast" in Bend, Or, located in the heart of Bend's Westside. Situated above Tokyo Starfish, the unparalleled cannabis dispensary in Central Oregon, this fantastic 2-bedroom apartment isn't just in a great location, but is also cannabis friendly. Just head downstairs to Tokyo Starfish with your complimentary gift card and experience the freshest selection of flower, edibles, drinks and other top cannabis products the dispensary has on hand.

Bend 3BR Home Near River Trail | Dog-Friendly

Welcome to your peaceful Bend getaway—a spacious 3-bedroom, 2-bath home near the Deschutes River Trail. Perfect for families and couples, this comfortable retreat features high-speed WiFi, a fully equipped kitchen, washer and dryer, and a bright, open living space designed for relaxation. Located minutes from downtown Bend and the Old Mill District, you’ll have easy access to shopping, dining, breweries, and outdoor adventures like hiking, biking, and paddle boarding.

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.

Aspen @ The DUPE - blocks from Old Mill District -

This beautiful and updated townhouse is located just blocks away from the Old Mill District. You can walk or ride down to the Hayden Homes Amphitheater, shopping, dining and of course the Deschutes River. The 2 bedroom 2 bath house itself is surrounded by trees and is very private. You will love the full tile shower in the master bathroom and the light and bright kitchen with updated appliances. This place is a perfect mix of comfort and location.

Modern Condo~Fireplace~Walk to Old Mill & River

✦ Deschutes Nest ✦ 🚶 Walk to Mt. Bachelor Shuttle & Hayden Homes Amphitheater 🌊 2 Blocks from the Deschutes River 🍻 Near Deschutes Brewery & Old Mill District 🏠 Modern Craftsman with Thoughtful Updates 🔥 Cozy Fireplace for Relaxing Evenings 🍳 Fully Equipped Kitchen 🌐 High-Speed Wi-Fi 🐾 Dog Friendly (w/fee) The home is dog friendly (1 small dog max) and the pet fee is $40/day (Max $250). Dogs only please. Pet fee requested after booking.