Bend vacation rentals

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Top-rated vacation rentals in Bend

Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.

Home in Bend
New Home in Lodges at Bachelor View - Book Now!
Enjoy Bend’s newest west-side neighborhood nestled beside Century Drive, the gateway to Mt. Bachelor and the Cascade Lakes. Our unique location puts you right on the connector trails to the popular Phil's Trail System for mountain biking or casually strolling along the Deschutes river trail. With access to the National Forest in just steps and breweries mere minutes down the road, Pinehaven is as 'Bend' as it gets. Thank you for considering Pinehaven for your stay. We think you’ll love it here!
$114 per night
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Guest suite in Bend
Bend, Oregon Private Suite; Perfect for 1 or 2
Hey there! Welcome to our place in beautiful Bend, OR! We absolutely love, love, love that we can offer a soft place to land after a day of adventuring in and around our awesome town! This is your spot if you are the order-in and snuggle-up kind; the get up, caffeine-up, and go kind; &/or the mid-day siesta kind. We have had tons of fun focusing on the details that will make your stay blissful and relaxing. From coffee options to Netflix, we've got your basics dialed so you can do you!
$60 per night
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Bungalow in Bend
Downtown Craftsman with King Bed and Private Yard
Stay at one few of the remaining homes in the core of downtown Bend. Enjoy the natural light from vaulted ceilings, charming architectural details, original hardwood floors and paintings by local artist Sheila Dunn. Choose from dozens of restaurants, breweries, coffee and shops within blocks. Cross the alley to food trucks and frequent live music at the historic Lucas House or relax in your private walled courtyard. A beautifully restored 1922 home with plants and warm wood throughout.
$93 per night
SUPERHOST

Vacation rentals for every style

Get the amount of space that is right for you

  • Cabins
  • Houses
  • Unique stays

Stay near Bend's top sights

Photo of Pilot Butte State Scenic Viewpoint
Pilot Butte State Scenic Viewpoint24 locals recommend
Photo of Mt. Bachelor Ski Resort
Mt. Bachelor Ski Resort28 locals recommend
Photo of BLOCKBUSTER
BLOCKBUSTER15 locals recommend
Photo of 10 Barrel Brewery
10 Barrel Brewery211 locals recommend
Photo of Monkless Belgian Ales
Monkless Belgian Ales35 locals recommend
Photo of Deschutes River Trail
Deschutes River Trail64 locals recommend

Bend cabin rentals

Cabin in Bend
Skyliners Getaway
$85 per night
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Cabin in Bend
Cabin in the Woods
$89 per night
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Cabin in Bend
Amazing, unobstructed River View Downtown Bend
$127 per night
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Cabin in Bend
The Drake Club, Walk to Downtown
$68 per night
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Cabin in Bend
Stunning Luxury Cabin on Tumalo Lake near town
$303 per night
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Cabin in Bend
Cozy Cabin For 6, Hot Tub, Fireplace, SHARC, WiFi
$114 per night
Cabin in Bend
Log Cabin on Tumalo Creek
$175 per night
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Cabin in La Pine
Little Deschutes Cabin - Clean & Quiet Get-Away
$147 per night
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Cabin in Bend
Tumalo Falls Modern Cabin Boulder House Bend
$206 per night
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Cabin in Bend
Quaint A-Frame Cabin close to Mt Bachelor
$90 per night
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Cabin in Sunriver
Ski Cabin 3min to Sunriver! Riverfront w/ Hot Tub!
$195 per night
Cabin in Bend
Spectacular Lodge on private lake near town
$671 per night
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Bend home rentals

Home in Bend
Bend Adventure Base - hot tub/firepit/bikes/floats
$169 per night
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Private room in Bend
Bend Ski Loft Retreat - no cleaning fee!
$44 per night
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Private room in Bend
Canal Master w/ Private Entrance & Self Check-in
$58 per night
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Private room in Bend
Second floor king bed, N.E. Bend
$51 per night
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Home in Bend
Private Luxury Cabin on Tumalo Lake near town
$289 per night
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Home in Bend
One Bedroom/Bathroom w/ TV Studio & Outdoor Patio!
$85 per night
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Home in Bend
RiverBend Bungalow- RIVERFRONT with Hot Tub, AC, 100+mbps Wifi, So Walkable
$180 per night
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Home in Bend
Bluebird Day - River Otter - 30 Day Minimum - WALK EVERYWHERE!
$95 per night
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Home in Bend
Little Lava, IN Downtown Bend, AC, 100+mbps Wifi, Bikes, Walk Everywhere
$89 per night
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Home in Bend
The Mallard House Walk to downtown Bend in 5 mins
$66 per night
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Home in Bend
No Cleaning Fees! Mckay Getaway walk to Drake Park and Millers Landing, Bikes and Paddle Boards!
$170 per night
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Home in Bend
Heart of Bend-Walkable, Ping Pong, Billards
$87 per night

Bend tiny home rentals

Tiny home in Bend
Forested Artistic Cozy Tiny House w/ Wildlife
$63 per night
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Tiny home in Bend
Contemporary Nordic tiny house in Three Rivers
$145 per night
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Tiny home in Bend
IT'S A WEE HOUSE
$68 per night
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Tiny home in Bend
The Bungalito - Westside Loft/Private/30+Days
$56 per night
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Tiny home in Bend
The Big Tiny
$118 per night
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Tiny home in Bend
The Sunset Bungalow, cozy, private and sweet.
$76 per night
Tiny home in Bend
Charming Tiny House Located on Bend Acreage
$75 per night
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Tiny home in Redmond
Relax with Mountain Views - 15min to Smith Rock!
$106 per night
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Private room in Bend
Rajneesh Aframe/Hot Tub, 10 min from downtown Bend
$76 per night
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Tiny home in Redmond
Tim's Tiny House # 1
$75 per night
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Tiny home in Sisters
Cozy Spot in the Woods - Dog Friendly
$95 per night
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Tiny home in Bend
The Zen Den
$185 per night
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Your guide to Bend

Introduction

Bend is arguably Oregon’s capital of outdoor sports, a four-season base for a host of activities. Hundreds of miles of hiking and single-track mountain bike trails weave around Central Oregon, and the Deschutes River flowing through Bend is filled with paddleboards and kayaks. When the snows arrive, the snowboards and snowshoes emerge, many of them headed up Mt. Bachelor. Increasingly, this fast-growing city offers more urbane pleasures as well. The Old Mill District, a former sawmill, has been turned into a complex of shops and cafes. And Bend is home to more than two dozen, from tiny brewpubs to major brands, attracting beer lovers who have no intention of hitting the trail.


When is the best time to stay in a vacation rental in Bend?

Every story you’ve heard about rainy Oregon? They don’t apply to Bend, located in the state’s high desert. This part of Central Oregon receives fewer than 12 inches of rain a year, plus another two feet of snow in wintertime, and sunny days outnumber cloudy ones.

Bend has four distinct seasons. From June through September, temperatures in the 70s and 80s Fahrenheit are common, while the shoulder seasons of spring and autumn are more likely to be cool, with days in the 40s and nights dropping down to the 20s. Temperatures frequently drop below freezing between November and March, and the slopes are covered in dry powder. Oregon may be the most casual state in the nation, so pack seasonally appropriate activewear and don’t worry about dressing up.


What are the top things to do in Bend?

Tumalo Falls

Viewing this spectacular 97-foot cascade, located 14 miles outside Bend, is only one reason to hike along Tumalo Creek. Many hikers use the falls as a starting point for four-to-eight-mile loops that wend past smaller but equally scenic waterfalls.

Mount Bachelor

Snowboarders and skiers from all over the West make pilgrimages to Bend for Mt. Bachelor’s 101 runs, which range in skill level from novice to expert. In the summer, mountain bikers take the same lifts up to fly along trails that descend through the trees.

Whitewater Park

Surfing in the middle of Bend? When the city parks department created a whitewater play area on the Deschutes River in 2015, short-board surfers flocked to its Green Wave feature. You can also rent an inner tube or a raft (plus lifejackets) for a leisurely two-mile float through the center of town. The bravest rafters can steer through the rocky, fast-flowing whitewater channel — dodging surfboards, of course.

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