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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.

Guest suite in Bend
Cozy Up at a Nature Inspired Boutique Studio in the Trees
Wake up to treetop views in a historic neighborhood. Stroll down to the end of the dead-end road and find the Deschutes River Trail, which can take you downtown along a winding paved path, or cross the river and enjoy miles of riverside walking. Perhaps enjoy a picnic at First Street Rapids Park, just steps away, then curl up and restore on the ultra comfy king bed at this spacious bungalow with hanging plants, botanical art, and a stunning cedar ceiling. Wake up refreshed and enjoy your coffee immersed in the vibe of this nature inspired (pet free!) space. This is a special space. A natural cedar plank ceiling accents the surrounding mature trees and landscape. Relaxing is inevitable in this private sanctuary where all your needs are met. The location cannot be beat with both the best of nature and convenience. There is a private stairway entrance from the backyard where you can come and go at any hour. There is a table and chairs to enjoy quiet backyard and nearby empty lot with chickens, trees and open meadow. You'll have access to a kitchenette (with sink, microwave, Keurig machine, ample counter space, picnic supplies, etc.), and a private bathroom. We are generally available to help you out with anything, since we live on the property as well but wish to respect your privacy. This is a historic neighborhood smack dab in the middle of Bend. There are multimillion dollar homes, as well as ones that haven't changed since they were built in the '20s. Nearby First Street Rapids Park has a variety of picnic areas and river access. Bend is certainly not known for it's public transportation, but fortunately there is ample street parking due to a vacant lot next to our home. There is also parking in front of our home. Please note that because the room is attached to our main home separated by a stairway, there are some normal household noises that will come into the room. We aren't a loud family, but if you are expecting total silence, you might want to look for another option. This is a special space. A natural cedar plank ceiling accents the surrounding mature trees and landscape. Relaxing is inevitable in this private sanctuary where all your needs are met. The location cannot be beat with both the best of nature and convenience. There is a private stairway entrance from the backyard where you can come and go at any hour. There is a table and chairs to enjoy quiet backyard and nearby empty lot with chickens, trees and open meadow. You'll have access to a kitchenette (with sink, microwave, Keurig machine, ample counter space, picnic supplies, etc.), and a private bathroom. We are generally available to help you out with anything, since we live on the property as well but wish to respect your privacy. This is a historic neighborhood smack dab in the middle of Bend. There are multimillion dollar homes, as well as ones that haven't changed since they were built in the '20s. Nearby First Street Rapids Park has a variety of picnic areas and river access. Bend is certainly not known for it's public transportation, but fortunately there is ample street parking due to a vacant lot next to our home. There is also parking in front of our home. Please note that because the room is attached to our main home separated by a stairway, there are some normal household noises that will come into the room. We aren't a loud family, but if you are expecting total silence, you might want to look for another option.
$81 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.
$127 per night
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Home in Bend
New Bend home - clean/hot tub/firepit/bikes/floats
Winter is here! The perfect base-camp for all of your Central Oregon adventures! Come settle in for exploration and recreation!! This home is well-located for walking and biking to the Old Mill, Deschutes River, concerts, parks, restaurants, breweries, and grocery stores. Quick access to all of the activities and events that make this area special! You'll love the convenient comfort of this centrally located home for your next Bend adventure!
$189 per night
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Stay near Bend's top sights

Photo of Old Mill District
Old Mill District292 locals recommend
Photo of BLOCKBUSTER
BLOCKBUSTER15 locals recommend
Photo of Cascade Village Shopping Center
Cascade Village Shopping Center18 locals recommend
Photo of Crux Fermentation Project
Crux Fermentation Project246 locals recommend
Photo of 10 Barrel Brewery
10 Barrel Brewery211 locals recommend
Photo of McMenamins
McMenamins158 locals recommend

Bend cabin rentals

Cabin in Bend
Amazing, unobstructed River View Downtown Bend
$145 per night
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Cabin in Bend
The Drake Club, Walk to Downtown
$70 per night
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Cabin in Bend
Cabin in the Woods
$101 per night
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Cabin in Bend
Cozy Cabin For 6, Hot Tub, Fireplace, SHARC, WiFi
$156 per night
Cabin in Bend
Skyliners Getaway
$86 per night
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Cabin in Bend
Quaint A-Frame Cabin close to Mt Bachelor
$91 per night
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Cabin in Bend
Mill Cabin at Deschutes Dunes River/ beach access
$130 per night
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Cabin in Bend
Romantic Luxury Cabin on Private Lake near Town
$257 per night
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Cabin in Bend
Log Cabin on Tumalo Creek
$170 per night
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Cabin in Bend
Private Luxury Cabin on Tumalo Lake near town
$323 per night
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Cabin in Bend
Tumalo Falls Modern Cabin Boulder House Bend
$199 per night
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Cabin in Bend
Family/Pets/A-C/Fireplace/Hot tub/SHARC/Village
$172 per night
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Bend house rentals

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
Bluebird Day - Ogden Studio - Walk Everywhere - Modern - Westside Location
$86 per night
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Home in Bend
Aspen House- Sweet, Modern Downtown Cottage, 100+mbps Wifi, A/C, Walk Everywhere
$99 per night
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Home in Bend
New Home in Lodges at Bachelor View - Book Now!
$116 per night
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Home in Bend
Bluebird Day - Hummingbird Cottage - Westside
$102 per night
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Home in Bend
30 minutes to Mt Bachelor! Beautiful, clean home.
$104 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
The Ebony House
$101 per night
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Home in Bend
Lodge Vibes in the City
$135 per night
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Home in Bend
"Urban Spruce" - Great peaceful location!!
$133 per night
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Home in Bend
The Birdseye House
$110 per night
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Private room in Bend
Edgecliff Manor - Room 3. Modern w/Queen bed
$45 per night
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Bend cottage rentals

Cottage in Bend
The Autumn Cottage: Historic Downtown Bend
$165 per night
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Cottage in Bend
The Modern Mill Cottage: Heart of Downtown Bend
$185 per night
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Cottage in Bend
Adorable West Side Cottage, Great Location!
$130 per night
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Cottage in Bend
Blue Spruce Cottage, 2/1, Modern, & Clean.
$131 per night
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Cottage in Bend
Winter Retreat in the Old Mill
$250 per night
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Cottage in Bend
Vintage Pink Hot Tub✓ Walkable✓
$100 per night
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Cottage in Bend
In the Heart of Tumalo Two
$82 per night
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Cottage in Bend
River Camp House
$150 per night
Cottage in Bend
Amazing Location! | Charming, Cozy Cottage
$225 per night
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Cottage in Bend
MCM remodeled cottage w/ hot tub & view
$159 per night
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Cottage in Bend
Cozy Sparrow Cottage in the Old Mill
$150 per night
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Cottage in Bend
The Westside Cottage: Galveston Ave. District
$153 per night
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Stays in Old Bend

Rental unit in Bend
Downtown Bend Hideaway. Long term welcome!
$151 per night
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Rental unit in Bend
Historic Drake Park Neighborhood .
$110 per night
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Rental unit in Bend
WALK DOWNTOWN AND OLD MILL- ONE BLOCK TO RIVER-#3
$105 per night
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Bungalow in Bend
Hygge & Harmony on Hip Galveston - Luxe with Charm, Hot Tub
$120 per night
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Stays in River West

Condo in Bend
Riverfront Condo 2 Blocks to Downtown Bend
$135 per night
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Condo in Bend
Riverfront Condo or Downtown Bend? How about both!
$92 per night
Condo in Bend
River View Condo- Edge of Downtown
$95 per night
Home in Bend
Renovated Riverfront condo w/balcony downtown Bend
$99 per night

Stays in Orchard District

Guesthouse in Bend
Midtown Gem! Park view-full kitchen-pet friendly!
$115 per night
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Townhouse in Bend
Mt Bachelor Retreat | Renovated Townhome in Bend
$103 per night
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Private room in Bend
Queen Bed - Hot tub!
$67 per night
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Rental unit in Bend
Villa77-Cozy Bend Ski-Season Getaway
$115 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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