Downtown Bend Vacation Rentals

Compare 27 vacation rentals. Enter your trip dates to get started.
USA > Oregon > Downtown Bend

Make Downtown Bend your next getaway—choose from 27 great vacation rentals

Explore our Downtown Bend vacation rentals & condos

Explore Downtown Bend house rentals, condo rentals, duplexes, and more


House rentals

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Condo rentals

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View 3 Duplexes

Downtown Bend vacation rentals for every getaway

Dog-friendly Hot tub Internet
Deschutes Riverside Escape 3D Tour
0 Bedroom | 1 Bath | Sleeps 2

Deschutes Riverside Escape - Bend, OR

From $49
Mt Bachelor Village - Seclusion in Century West 3D Tour
0 Bedroom | 1 Bath | Sleeps 2

Mt Bachelor Village - Seclusion in Century West - Bend, OR

From $49
The Heyburn Cottage (Upstairs & Downstairs) 3D Tour
6 Bedroom | 4 Bath | Sleeps 13

The Heyburn Cottage (Upstairs & Downstairs) - Bend, OR

From $164
Mt Bachelor Village Ski House # 262 3D Tour
1 Bedroom | 1.5 Bath | Sleeps 6

Mt Bachelor Village Ski House # 262 - Bend, OR

From $95
Bend Golf & Country Club Home 3D Tour
4 Bedroom | 2.5 Bath | Sleeps 12

Bend Golf & Country Club Home - Bend, OR

From $158

View 22 more homes

Recent Downtown Bend vacation rental reviews

This cozy bungalow offered the perfect retreat for our weekend ladies getaway (4 ladies + 2 dogs)! Walking distance to the Les Schwab Amphitheater and Deschutes River Trail (.6 miles). We encountered a deer in the driveway during our stay and enjoyed the blue jays while drinking Sisters Coffee on the front porch. Highlights of our stay included the High Desert Museum and Northwest Crossing Saturday Market! Will definitely be back, already planning our winter retreat!
Nathaniel W. | Sep 2021
This home was perfect for our trip to Bend Oregon. Everyone slept very comfortably and plenty of places to sit and hangout or read! It's at the top of the hill so the views are amazing, but would definitely want to wear workout clothes/shoes if you were to go on a walk, as the walk back is fairly steep. Not pictured is an awesome grass area in the backyard! Would definitely stay here again!
Kiah H. | Sep 2021
Easily accessible to where you want to go.
Joseph C. | Sep 2021

Book confidently. Stay comfortably.

Book confidently. Stay comfortably.
24/7 support
Easy check-in
Easy check-in
Professional cleaning
Professional cleaning

While a rustic countryside cabin has its perks, it’s not surprising that many Deschutes County visitors opt for a chic retreat in Downtown Bend. With outdoor adventure all around (like Mount Bachelor, just 22 miles away), it’s easy to explore the great outdoors from the comfort of a Downtown Bend vacation rental while also enjoying the benefits of staying in town.

If you’re visiting Bend during the summer, don’t miss the chance to float the Deschutes River—which happens to run right through the middle of town, so your rental won’t be far. Hiking, paddle boarding, mountain biking, and rock climbing are all fair game, too. In the evenings, clean up and hit the sidewalks: Downtown Bend is delightfully walkable. Dine out at Bos Taurus or another one of the neighborhood’s upscale establishments, or enjoy a casual dinner on the Crux Brewing patio. You won’t regret choosing a vacation rental in Downtown Bend!