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LUXURY VACATION RENTALS IN Bend, OR

Bend, Oregon is the perfect place to unleash your inner passion for outdoor recreation. The largest city east of the Cascade Mountains, Bend offers kayaking and rafting on the triple waterfalls of the Deschutes river, fly fishing for trout and steelhead, world-class rock climbing, hiking, camping, skiing and riding on Mt. Bachelor, and even cave spelunking. Myriad galleries, restaurants, boutiques, specialty shops and an outdoor amphitheater only enhance your visit. With everything Bend has to offer, you’ll probably have to take multiple trips to experience it all.

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38 results found

1 Cherrywood

Bend, OR

5
BEDROOMS

10
SLEEPS

$191 - $1,521/night

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1 Colonial

Bend, OR

5
BEDROOMS

14
SLEEPS

$235 - $1,919/night

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11 Tournament

Bend, OR

5
BEDROOMS

14
SLEEPS

$346 - $2,756/night

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11 Vine Maple

Bend, OR

5
BEDROOMS

14
SLEEPS

$352 - $2,801/night

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18 Hickory

Bend, OR

4
BEDROOMS

10
SLEEPS

$186 - $1,483/night

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2 Dixie Mt

Bend, OR

4
BEDROOMS

10
SLEEPS

$200 - $1,593/night

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2 Pioneer

Bend, OR

3
BEDROOMS

6
SLEEPS

$281 - $977/night

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2 Sarazen

Bend, OR

4
BEDROOMS

10
SLEEPS

$172 - $1,372/night

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22 Rogue

Bend, OR

4
BEDROOMS

10
SLEEPS

$185 - $1,480/night

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23 Quelah

Bend, OR

6
BEDROOMS

16
SLEEPS

$256 - $2,268/night

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3 Mulligan

Bend, OR

4
BEDROOMS

10
SLEEPS

$152 - $1,329/night

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3 Spyglass

Bend, OR

4
BEDROOMS

10
SLEEPS

$200 - $1,589/night

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3 Tumalo

Bend, OR

4
BEDROOMS

12
SLEEPS

$175 - $1,387/night

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3BR w/ Fireplace & Deck, Near Golf

Bend, OR

3
BEDROOMS

7
SLEEPS

$267 - $746/night

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5 Vine Maple

Bend, OR

6
BEDROOMS

16
SLEEPS

$317 - $2,999/night

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8 Mt Baker

Bend, OR

4
BEDROOMS

10
SLEEPS

$171 - $1,367/night

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9 Hoodoo

Bend, OR

5
BEDROOMS

12
SLEEPS

$207 - $1,648/night

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Awbrey

Bend, OR

4
BEDROOMS

8
SLEEPS

$227 - $1,476/night

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Big Canyon

Bend, OR

4
BEDROOMS

10
SLEEPS

$191 - $1,248/night

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Cairn

Bend, OR

5
BEDROOMS

13
SLEEPS

$312 - $1,954/night

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Deschutes Landing at the Old Mill Riverfront

Bend, OR

3
BEDROOMS

6
SLEEPS

$326 - $811/night

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Drake Park Villa

Bend, OR

3
BEDROOMS

6
SLEEPS

$243 - $1,582/night

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Exceptional Vacation Home in Sunriver

Bend, OR

5
BEDROOMS

12
SLEEPS

$1,155 - $1,171/night

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Extraordinary Riverfront Home Next to Biking, Hiking & Fishing

Bend, OR

5
BEDROOMS

12
SLEEPS

$609 - $1,379/night

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Five Peaks

Bend, OR

5
BEDROOMS

12
SLEEPS

$250 - $1,879/night

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Flagline Trail

Bend, OR

5
BEDROOMS

14
SLEEPS

$307 - $1,811/night

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Golden Butte

Bend, OR

4
BEDROOMS

8
SLEEPS

$259 - $1,175/night

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Hillside Haven

Bend, OR

4
BEDROOMS

10
SLEEPS

$176 - $1,149/night

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Lovely Bend Retreat w/ Private Patio & Firepit

Bend, OR

3
BEDROOMS

6
SLEEPS

$286 - $701/night

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Luxe Retreat w/ Game room, Library, Fitness Room

Bend, OR

5
BEDROOMS

10
SLEEPS

$685 - $1,117/night

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New Listing! Quiet Home w/ Hot Tub

Bend, OR

3
BEDROOMS

6
SLEEPS

$376 - $627/night

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Quiet Sunriver Home with Private Hot Tub & Deck

Bend, OR

4
BEDROOMS

10
SLEEPS

$264 - $1,113/night

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Quinn Creek

Bend, OR

3
BEDROOMS

8
SLEEPS

$200 - $1,025/night

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Rimrock

Bend, OR

4
BEDROOMS

8
SLEEPS

$218 - $1,267/night

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Streamline Moderne Estate with Private Hot Tub

Bend, OR

3
BEDROOMS

12
SLEEPS

$532 - $982/night

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Tailwinds Farm, Secluded Estate On The River, Amazing Views

Bend, OR

4
BEDROOMS

8
SLEEPS

$403 - $1,418/night

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The Golden Zone

Bend, OR

4
BEDROOMS

8
SLEEPS

$267 - $1,737/night

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Trails End Retreat

Bend, OR

5
BEDROOMS

12
SLEEPS

$228 - $1,486/night

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Home	Bedrooms	Sleeps	SqFt	Starting Nightly Rate
1 Cherrywood	5	10	2,800	$191	VIEW HOME
1 Colonial	5	14	3,000	$235	VIEW HOME
11 Tournament	5	14	3,500	$346	VIEW HOME
11 Vine Maple	5	14	3,500	$352	VIEW HOME
18 Hickory	4	10	2,437	$186	VIEW HOME
2 Dixie Mt	4	10	2,400	$200	VIEW HOME
2 Pioneer	3	6	1,600	$281	VIEW HOME
2 Sarazen	4	10	2,150	$172	VIEW HOME
22 Rogue	4	10	2,500	$185	VIEW HOME
23 Quelah	6	16	3,381	$256	VIEW HOME
3 Mulligan	4	10	2,300	$152	VIEW HOME
3 Spyglass	4	10	2,300	$200	VIEW HOME
3 Tumalo	4	12	2,165	$175	VIEW HOME
3BR w/ Fireplace & Deck, Near Golf	3	7	0	$267	VIEW HOME
5 Vine Maple	6	16	3,900	$317	VIEW HOME
8 Mt Baker	4	10	2,400	$171	VIEW HOME
9 Hoodoo	5	12	2,793	$207	VIEW HOME
Awbrey	4	8	3,000	$227	VIEW HOME
Big Canyon	4	10	2,540	$191	VIEW HOME
Cairn	5	13	2,851	$312	VIEW HOME
Deschutes Landing at the Old Mill Riverfront	3	6	2,311	$326	VIEW HOME
Drake Park Villa	3	6	3,292	$243	VIEW HOME
Exceptional Vacation Home in Sunriver	5	12	4,939	$1,155	VIEW HOME
Extraordinary Riverfront Home Next to Biking, Hiking & Fishing	5	12	0	$609	VIEW HOME
Five Peaks	5	12	3,000	$250	VIEW HOME
Flagline Trail	5	14	3,500	$307	VIEW HOME
Golden Butte	4	8	2,608	$259	VIEW HOME
Hillside Haven	4	10	1,763	$176	VIEW HOME
Lovely Bend Retreat w/ Private Patio & Firepit	3	6	1,377	$286	VIEW HOME
Luxe Retreat w/ Game room, Library, Fitness Room	5	10	0	$685	VIEW HOME
New Listing! Quiet Home w/ Hot Tub	3	6	0	$376	VIEW HOME
Quiet Sunriver Home with Private Hot Tub & Deck	4	10	0	$264	VIEW HOME
Quinn Creek	3	8	3,245	$200	VIEW HOME
Rimrock	4	8	2,861	$218	VIEW HOME
Streamline Moderne Estate with Private Hot Tub	3	12	2,485	$532	VIEW HOME
Tailwinds Farm, Secluded Estate On The River, Amazing Views	4	8	0	$403	VIEW HOME
The Golden Zone	4	8	2,243	$267	VIEW HOME
Trails End Retreat	5	12	3,500	$228	VIEW HOME

Luxury Vacations in Bend, OR: Attractions, Activities, and Food

Before You Go: Bend, Oregon Vacation Tips

Nothing should get in the way of your perfect experience. Check these helpful tips for ensuring a smooth journey.

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Passports, Visas and Consideration for Minors

Passports, Visas and Consideration for Minors You are required to have a passport or other accepted document that establishes your identity and nationality to enter or re-enter the United States. In the case of minors, when traveling with your children, but without your spouse or partner, please have a notarized letter from the non-present parent authorizing the child’s travel. If not, the child may be held at security and unable to travel. This letter is highly recommended for any international destination (airlines include Hawaii in this case), and suggested for travel within the continental United States.

Traveling with Prescription Medicine

If you are traveling with prescription medicines, carry them in their original containers and bring a copy of your prescription. If you buy medications abroad, be aware that they may not be FDA-approved or allowed into the United States. For more information on customs rules and regulations, please contact 202.354.1000 or visit www.cbp.gov.

LUXURY VACATION RENTALS IN Bend, OR

Filter By Amenities

38 results found

1 Cherrywood

1 Colonial

11 Tournament

11 Vine Maple

18 Hickory

2 Dixie Mt

2 Pioneer

2 Sarazen

22 Rogue

23 Quelah

3 Mulligan

3 Spyglass

3 Tumalo

3BR w/ Fireplace & Deck, Near Golf

5 Vine Maple

8 Mt Baker

9 Hoodoo

Awbrey

Big Canyon

Cairn

Deschutes Landing at the Old Mill Riverfront

Drake Park Villa

Exceptional Vacation Home in Sunriver

Extraordinary Riverfront Home Next to Biking, Hiking & Fishing

Five Peaks

Flagline Trail

Golden Butte

Hillside Haven

Lovely Bend Retreat w/ Private Patio & Firepit

Luxe Retreat w/ Game room, Library, Fitness Room

New Listing! Quiet Home w/ Hot Tub

Quiet Sunriver Home with Private Hot Tub & Deck

Quinn Creek

Rimrock

Streamline Moderne Estate with Private Hot Tub

Tailwinds Farm, Secluded Estate On The River, Amazing Views

The Golden Zone

Trails End Retreat

Before You Go: Bend, Oregon Vacation Tips

Passports, Visas and Consideration for Minors

Traveling with Prescription Medicine

New Travel Benefits with Time & Place!