Bend Oregon

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Top-rated vacation rentals in Bend

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

Bend Caboose - cozy, private, walk to Crux Brewery
Entire guest suite · 2 guests · 1 bed · 1 bath
Bend Caboose - cozy, private, walk to Crux BreweryEnjoy your next visit to Central Oregon in the Bend Caboose! Our newly renovated space is located in the center of Bend with the convenience to drive, bike, or walk to the Box Factory, downtown, and the Old Mill District. Our space is a 10-minute walk to Crux Brewery and the Box Factory and a 20-minute walk to downtown. By car, our space will get you to Mt. Bachelor and the Cascade Lakes in 25 minutes. You will also have access to get around town with the use of our complimentary cruiser bikes.
Studio with living area & Private entrance-Suite#3
SUPERHOST
Entire guest suite · 3 guests · 1 bed · 1 bath
Studio with living area & Private entrance-Suite#3Newly remodeled unit with 75" Smart Roku TV & 60" Fireplace! We are EARLY risers and work East Coast hours. We have sound proofed well from the feedback we're receiving, but If you have any concerns over potential of noise from a family of 4, please book another place as your comfort is our priority! PLEASE ALSO READ "OTHER THINGS TO NOTE" SECTION RE: PETS & PET FEE!
Little Sister
SUPERHOST
Entire guesthouse · 2 guests · 1 bed · 1 bath
Little SisterGreat Location!!! Sweet, private studio in Shevlin Ridge right nearby Shevlin Park in Bend. Enjoy your own space with all of the amenities!

Vacation rentals for every style

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Popular amenities for Bend vacation rentals

  • Kitchen
  • Wifi
  • Pool
  • Free parking on premises
  • Air conditioning

Other great vacation rentals in Bend

  1. Entire residential home
  2. Bend
Emersen’s Place
$127 per night
  1. Entire condominium (condo)
  2. Bend
Affordable Convenience in Bend
$90 per night
SUPERHOST
  1. Entire rental unit
  2. Bend
Villa77-Perfect Couple's Getaway in Midtown
$155 per night
SUPERHOST
  1. Entire residential home
  2. Bend
Perfect Location For The River & Old Mill District
$139 per night
PLUS
  1. Entire bungalow
  2. Bend
Ski, Bike, and Golf from a Spacious Family Bungalow
$176 per night
SUPERHOST
  1. Entire guest suite
  2. Bend
Private entry to the suite,deep clean,quiet, safe.
$96 per night
  1. Entire condominium (condo)
  2. Bend
Downtown area upscale condo near river trail
$106 per night
SUPERHOST
  1. Entire residential home
  2. Bend
Old Mill Cottage In Deschutes River Woods
$105 per night
SUPERHOST
  1. Entire guesthouse
  2. Bend
Old Mill and River Walk Retreat
$129 per night
SUPERHOST
  1. Private room
  2. Bend
Canal Master w/ Private Entrance & Self Check-in
$59 per night
SUPERHOST
  1. Entire residential home
  2. Bend
New Home in Lodges at Bachelor View - Book Now!
$163 per night
PLUS
  1. Entire residential home
  2. Bend
Modern Mountain Retreat Steps from First Street Rapids Park
$184 per night

Your guide to Bend

All About Bend


How do I get around Bend?

Bend is located 175 miles southeast of Portland, a three-hour drive. If you’re coming from out of state, you can fly into the busy Portland International Airport (PDX), or search out flights to Roberts Field Airport (RDM) in nearby Redmond (17 miles away), which is served by four major airlines. There are plenty of car-rental options at both airports, and taxis, rideshares, and airport shuttles from the Redmond airport can take you to your destination.

If you’re not planning on using a car while you’re in town, several motorcoach companies cross through Central Oregon. North-south Amtrak trains stop at Chemult, and riders can then take an Amtrak bus on to Bend. In town, public bus routes are plentiful, as are bike rentals, and the Mt. Bachelor Shuttle will take you up the mountain in summer and winter.


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.