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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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35 results found

1 Colonial

Bend, OR

5
BEDROOMS

14
SLEEPS

$244 - $1,739/night

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11 Tournament

Bend, OR

5
BEDROOMS

14
SLEEPS

$284 - $1,971/night

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11 Vine Maple

Bend, OR

5
BEDROOMS

14
SLEEPS

$296 - $2,412/night

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18 Hickory

Bend, OR

4
BEDROOMS

10
SLEEPS

$149 - $1,035/night

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2 Pioneer

Bend, OR

3
BEDROOMS

6
SLEEPS

$277 - $731/night

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2 Sarazen

Bend, OR

4
BEDROOMS

10
SLEEPS

$136 - $949/night

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22 Rogue

Bend, OR

4
BEDROOMS

10
SLEEPS

$175 - $1,242/night

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23 Quelah

Bend, OR

6
BEDROOMS

16
SLEEPS

$246 - $1,926/night

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3 Mulligan

Bend, OR

4
BEDROOMS

10
SLEEPS

$143 - $991/night

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3 Spyglass

Bend, OR

4
BEDROOMS

10
SLEEPS

$188 - $1,274/night

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3 Tumalo

Bend, OR

3 Tumalo is a beautifully renovated home featuring 4 bedrooms.

4
BEDROOMS

12
SLEEPS

$198 - $1,558/night

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5 Vine Maple

Bend, OR

6
BEDROOMS

16
SLEEPS

$355 - $2,530/night

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8 Mt Baker

Bend, OR

4
BEDROOMS

10
SLEEPS

$160 - $1,071/night

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9 Hoodoo

Bend, OR

5
BEDROOMS

12
SLEEPS

$204 - $1,453/night

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Awbrey

Bend, OR

4
BEDROOMS

8
SLEEPS

$234 - $1,322/night

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Big Canyon

Bend, OR

4
BEDROOMS

10
SLEEPS

$154 - $1,159/night

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Big Pine | Stunning Secluded Oregon Home w/ Hot Tub

Bend, OR

4
BEDROOMS

10
SLEEPS

$326 - $1,510/night

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Big Sky | Beautiful Mountain Home w/ Great Views!

Bend, OR

5
BEDROOMS

12
SLEEPS

$400 - $2,629/night

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Cairn

Bend, OR

5
BEDROOMS

13
SLEEPS

$332 - $1,649/night

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Deschutes | Two Story Modern Cabin Only 10-Minutes From DT Bend

Bend, OR

3
BEDROOMS

8
SLEEPS

$281 - $874/night

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Drake Park Villa

Bend, OR

3
BEDROOMS

6
SLEEPS

$209 - $1,732/night

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Five Peaks

Bend, OR

5
BEDROOMS

12
SLEEPS

$332 - $1,586/night

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Flagline Trail

Bend, OR

5
BEDROOMS

14
SLEEPS

$234 - $1,569/night

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Golden Butte

Bend, OR

4
BEDROOMS

8
SLEEPS

$256 - $845/night

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Hillside Haven

Bend, OR

4
BEDROOMS

10
SLEEPS

$160 - $1,242/night

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Klamath | Gorgeous Mountain Home w/ Fire Pit, Spa & Lake Views

Bend, OR

5
BEDROOMS

10
SLEEPS

$360 - $2,011/night

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Mountain Gem | Charming Sunriver Home on Golf Course w/ Hot Tub

Bend, OR

3
BEDROOMS

8
SLEEPS

$559 - $1,292/night

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Mulligan | Modern Sunriver Home on Woodlands Golf Course w/ Hot Tub

Bend, OR

3
BEDROOMS

8
SLEEPS

$491 - $1,877/night

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Powell | Secluded Home only 10 Mins from DT Bend w/ Hot Tub

Bend, OR

6
BEDROOMS

20
SLEEPS

$495 - $3,515/night

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Quinn Creek

Bend, OR

3
BEDROOMS

8
SLEEPS

$197 - $826/night

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Red Rover | Cute Cottage w/ Hot Tub Surrounded by Deschutes River and Forest

Bend, OR

5
BEDROOMS

8
SLEEPS

$342 - $656/night

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Skylight | Elevated Mountain Home w/ Hot Tub, Billiards, Large Patio

Bend, OR

7
BEDROOMS

16
SLEEPS

$556 - $3,283/night

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Sunriver | Cozy Mountain Home w/ Indoor Pool and Hot Tub

Bend, OR

5
BEDROOMS

12
SLEEPS

$475 - $3,171/night

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Tailwinds Farm, Secluded Estate On The River, Amazing Views

Bend, OR

4
BEDROOMS

8
SLEEPS

$170 - $1,165/night

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Trails End Retreat

Bend, OR

5
BEDROOMS

12
SLEEPS

$215 - $1,319/night

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Home	Bedrooms	Sleeps	SqFt	Starting Nightly Rate
1 Colonial	5	14	3,000	$244	VIEW HOME
11 Tournament	5	14	3,500	$284	VIEW HOME
11 Vine Maple	5	14	3,500	$296	VIEW HOME
18 Hickory	4	10	2,437	$149	VIEW HOME
2 Pioneer	3	6	1,600	$277	VIEW HOME
2 Sarazen	4	10	2,150	$136	VIEW HOME
22 Rogue	4	10	2,500	$175	VIEW HOME
23 Quelah	6	16	3,381	$246	VIEW HOME
3 Mulligan	4	10	2,300	$143	VIEW HOME
3 Spyglass	4	10	2,300	$188	VIEW HOME
3 Tumalo	4	12	2,165	$198	VIEW HOME
5 Vine Maple	6	16	3,900	$355	VIEW HOME
8 Mt Baker	4	10	2,400	$160	VIEW HOME
9 Hoodoo	5	12	2,793	$204	VIEW HOME
Awbrey	4	8	3,000	$234	VIEW HOME
Big Canyon	4	10	2,540	$154	VIEW HOME
Big Pine \| Stunning Secluded Oregon Home w/ Hot Tub	4	10	0	$326	VIEW HOME
Big Sky \| Beautiful Mountain Home w/ Great Views!	5	12	3,778	$400	VIEW HOME
Cairn	5	13	2,851	$332	VIEW HOME
Deschutes \| Two Story Modern Cabin Only 10-Minutes From DT Bend	3	8	1,894	$281	VIEW HOME
Drake Park Villa	3	6	3,292	$209	VIEW HOME
Five Peaks	5	12	3,000	$332	VIEW HOME
Flagline Trail	5	14	3,500	$234	VIEW HOME
Golden Butte	4	8	2,608	$256	VIEW HOME
Hillside Haven	4	10	1,763	$160	VIEW HOME
Klamath \| Gorgeous Mountain Home w/ Fire Pit, Spa & Lake Views	5	10	2,841	$360	VIEW HOME
Mountain Gem \| Charming Sunriver Home on Golf Course w/ Hot Tub	3	8	0	$559	VIEW HOME
Mulligan \| Modern Sunriver Home on Woodlands Golf Course w/ Hot Tub	3	8	0	$491	VIEW HOME
Powell \| Secluded Home only 10 Mins from DT Bend w/ Hot Tub	6	20	6,167	$495	VIEW HOME
Quinn Creek	3	8	3,245	$197	VIEW HOME
Red Rover \| Cute Cottage w/ Hot Tub Surrounded by Deschutes River and Forest	5	8	0	$342	VIEW HOME
Skylight \| Elevated Mountain Home w/ Hot Tub, Billiards, Large Patio	7	16	4,800	$556	VIEW HOME
Sunriver \| Cozy Mountain Home w/ Indoor Pool and Hot Tub	5	12	3,530	$475	VIEW HOME
Tailwinds Farm, Secluded Estate On The River, Amazing Views	4	8	0	$170	VIEW HOME
Trails End Retreat	5	12	3,500	$215	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

35 results found

1 Colonial

11 Tournament

11 Vine Maple

18 Hickory

2 Pioneer

2 Sarazen

22 Rogue

23 Quelah

3 Mulligan

3 Spyglass

3 Tumalo

5 Vine Maple

8 Mt Baker

9 Hoodoo

Awbrey

Big Canyon

Big Pine | Stunning Secluded Oregon Home w/ Hot Tub

Big Sky | Beautiful Mountain Home w/ Great Views!

Cairn

Deschutes | Two Story Modern Cabin Only 10-Minutes From DT Bend

Drake Park Villa

Five Peaks

Flagline Trail

Golden Butte

Hillside Haven

Klamath | Gorgeous Mountain Home w/ Fire Pit, Spa & Lake Views

Mountain Gem | Charming Sunriver Home on Golf Course w/ Hot Tub

Mulligan | Modern Sunriver Home on Woodlands Golf Course w/ Hot Tub

Powell | Secluded Home only 10 Mins from DT Bend w/ Hot Tub

Quinn Creek

Red Rover | Cute Cottage w/ Hot Tub Surrounded by Deschutes River and Forest

Skylight | Elevated Mountain Home w/ Hot Tub, Billiards, Large Patio

Sunriver | Cozy Mountain Home w/ Indoor Pool and Hot Tub

Tailwinds Farm, Secluded Estate On The River, Amazing Views

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!