1960+ Vacation Rentals Near Oregon Trail of Dreams |
  1. USA
  2. Oregon
  3. Bend
  4. Oregon Trail of Dreams

Luxury Cruises - Vacation Rentals in Oregon Trail of Dreams

The Executive Lodge up in the West Hills and is 2 miles from downtown Bend. From US $1,131
         

10.0 (148 Reviews)
House
The Executive Lodge up in the West Hills and is 2 miles from downtown Bend.
  • Air Conditioner
  • Parking
  • Pet Friendly

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Aaron Way From US $241
         

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New
House
Aaron Way
  • Parking
  • Pet Friendly
  • Breakfast

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Bluebird Day - Ogden Getaway From US $235
         

9.8 (19 Reviews)
House
Bluebird Day - Ogden Getaway
  • Air Conditioner
  • TV
  • Security/Safety

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Five Peaks - Gorgeous! Hot Tub, Mountain Views, Road to Mt Bachelor! From US $664
         

9.8 (92 Reviews)
House
Five Peaks - Gorgeous! Hot Tub, Mountain Views, Road to Mt Bachelor!
  • Air Conditioner
  • Parking
  • TV

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Historic Farmhouse on Bends Westside From US $267
         

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4.0 (2 Reviews)
House
Historic Farmhouse on Bends Westside
  • Parking
  • Balcony/Terrace
  • Child Friendly

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Bluebird Day - River Gem Bungalow From US $189
         

9.6 (94 Reviews)
House
Bluebird Day - River Gem Bungalow
  • Air Conditioner
  • Pet Friendly
  • TV

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Great Reviews │West Side Bungalow │Walk Everywhere │Hot Tub │One Block to River From US $271
         

9.8 (71 Reviews)
House
Great Reviews │West Side Bungalow │Walk Everywhere │Hot Tub │One Block to River
  • Air Conditioner
  • Parking
  • Pet Friendly

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Bluebird Day - Cinder Cone Bungalow From US $440
         

10.0 (3 Reviews)
House
Bluebird Day - Cinder Cone Bungalow
  • Pet Friendly
  • Security/Safety
  • Fireplace/Heating

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The Aerie Suites by AvantStay – Modern Comfort with Mountain Views From US $457
         

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10.0 (3 Reviews)
Apartment
The Aerie Suites by AvantStay – Modern Comfort with Mountain Views
  • Air Conditioner
  • Parking
  • Pet Friendly

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West Side Gem │King Beds │Walk Everywhere │Hot Tub │Large Living Spaces From US $346
         

9.8 (60 Reviews)
House
West Side Gem │King Beds │Walk Everywhere │Hot Tub │Large Living Spaces
  • Air Conditioner
  • Parking
  • Pet Friendly

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Contemporary Chic │West Side │Walk Everywhere │Hot Tub │One Block to River From US $261
         

9.8 (51 Reviews)
Cottage
Contemporary Chic │West Side │Walk Everywhere │Hot Tub │One Block to River
  • Air Conditioner
  • Parking
  • Pet Friendly

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Awbrey - Amazing! Steps to Downtown & River, Gorgeous, Newer, A/C From US $808
         

9.8 (114 Reviews)
House
Awbrey - Amazing! Steps to Downtown & River, Gorgeous, Newer, A/C
  • Air Conditioner
  • Parking
  • TV

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Historic Downtown Bend Cottage - walkable to the best of Bend! From US $222
         

9.8 (90 Reviews)
House
Historic Downtown Bend Cottage - walkable to the best of Bend!
  • Air Conditioner
  • Parking
  • Pet Friendly

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Drake Park Villa - River Front on Mirror Pond & Drake Park, Exquisite, Gourmet Kitchen From US $581
         

9.6 (91 Reviews)
House
Drake Park Villa - River Front on Mirror Pond & Drake Park, Exquisite, Gourmet Kitchen
  • Air Conditioner
  • Parking
  • TV

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Quinn Creek - Gorgeous and Updated! Perfect Location in NW Bend, Pool Table, 20 Min To Bachelor! From US $349
         

10.0 (95 Reviews)
House
Quinn Creek - Gorgeous and Updated! Perfect Location in NW Bend, Pool Table, 20 Min To Bachelor!
  • Air Conditioner
  • TV
  • Balcony/Terrace

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Prime Location Near River, Downtown, Old Mill And All Your Favorite Breweries From US $220
         

9.6 (173 Reviews)
Cottage
Prime Location Near River, Downtown, Old Mill And All Your Favorite Breweries
  • Air Conditioner
  • Parking
  • Pet Friendly

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NW Lexington | River West | pet (dog) friendly hot tub From US $394
         

9.6 (56 Reviews)
House
NW Lexington | River West | pet (dog) friendly hot tub
  • Air Conditioner
  • Parking
  • Pet Friendly

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Villa 5 - Hot Tub, Golf Course Views, Large Deck, Quiet and Peaceful in Broken Top From US $306
         

9.4 (126 Reviews)
House
Villa 5 - Hot Tub, Golf Course Views, Large Deck, Quiet and Peaceful in Broken Top
  • Air Conditioner
  • Pet Friendly
  • TV

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Spacious and charming Craftsman retreat, six bedrooms, sleeps 18. From US $957
         

10.0 (244 Reviews)
Cabin
Spacious and charming Craftsman retreat, six bedrooms, sleeps 18.
  • Air Conditioner
  • Parking
  • Pet Friendly

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Skyline Lodge, Gorgeous Setting, Walk to Downtown! From US $793
         

10.0 (199 Reviews)
Cabin
Skyline Lodge, Gorgeous Setting, Walk to Downtown!
  • Air Conditioner
  • Parking
  • Pool

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LOCATION! WALK TO DOWNTOWN AND OLD MILL - ONE BEDROOM ONE BLOCK FROM THE RIVER From US $137
         

10.0 (86 Reviews)
Apartment
LOCATION! WALK TO DOWNTOWN AND OLD MILL - ONE BEDROOM ONE BLOCK FROM THE RIVER
  • Air Conditioner
  • Parking
  • TV

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Luxury living and scenic views of Tetherow, just off the 18th green. 5Bed, 4Bath From US $1,829
         

10.0 (24 Reviews)
House
Luxury living and scenic views of Tetherow, just off the 18th green. 5Bed, 4Bath
  • Air Conditioner
  • Parking
  • Pool

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Cairn - Tetherow Executive Retreat, Private Hot Tub, Modern From US $612
         

9.4 (72 Reviews)
House
Cairn - Tetherow Executive Retreat, Private Hot Tub, Modern
  • Air Conditioner
  • Parking
  • Pet Friendly

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Bernhard Justice- Salt Hot Tub, 100+ Wifi, Gas Firepl, EV plug, Walkable! From US $346
         

10.0 (120 Reviews)
House
Bernhard Justice- Salt Hot Tub, 100+ Wifi, Gas Firepl, EV plug, Walkable!
  • Air Conditioner
  • Parking
  • TV

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★ Pro Tip: Luxurycruises makes it easy to compare the best listings on Luxurycruises homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Luxurycruises homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Oregon Trail of Dreams.

Weather in Oregon Trail of Dreams

View the weather forecast for Oregon Trail of Dreams before booking your Oregon Trail of Dreams Vacation Rentals to confirm your best time to go.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F

Top Attractions Around Oregon Trail of Dreams, OR

Luxurycruises offers a large selection of top attractions around Oregon Trail of Dreams. Research things to do on your vacation before you visit Oregon Trail of Dreams.


Old Mill District Les Schwab Amphitheater Deschutes Brewery Downtown Bend Business Association Drake Park Tower Theater Bend Rock Gym Deschutes National Forest Widgi Creek Golf Club Bend River Promenade Tetherow Golf Club Central Bend Sunriver Resort Golf Course Central Oregon Community College The Village High Desert Museum Cascade Range Sunriver Homeowners Aquatic & Recreation Center Bend Factory Stores Westside Church

Oregon Trail of Dreams Vacation Rental Frequently Asked Questions

How many vacation rentals are available in Oregon Trail of Dreams?

Currently, the total number of properties listed in 2026 is over 1960 in the Oregon Trail of Dreams area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Oregon Trail of Dreams.