Vacation Rentals in Oregon Trail of Dreams, OR: Compare 10+ Sites & Save

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  3.  USA

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  6.  Oregon Trail of Dreams

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1143 Best Vacation Rentals in Oregon Trail of Dreams (Starting from $109)

River Ridge 322A - Meredith Lodging
River Ridge 322A - Meredith Lodging
House
Bend, OR, USA
0.0k from Oregon Trail of Dreams center

Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Jacuzzis

1 Bedroom4 Guests
New to Booking
$330
Average price / night
Check Availability
Studio condo with shared pool & hot tub, WiFi, close to outdoor recreation
Studio condo with shared pool & hot tub, WiFi, close to outdoor recreation
Apartment
Bend, OR, 97702, United States
0.1k from Oregon Trail of Dreams center

AC, Heater, Hot Tub, Internet, Kitchen, Living Area, Microwave, No Smoking, Pool

New to Booking
$109
Average price / night
Check Availability
River Ridge 322AB - Meredith Lodging
River Ridge 322AB - Meredith Lodging
House
Bend, OR, USA
0.0k from Oregon Trail of Dreams center

Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Jacuzzis

2 Bedrooms6 Guests
New to Booking
$444
Average price / night
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Frosty Summit Condo at Mount Bachelor Village
Frosty Summit Condo at Mount Bachelor Village
Apartment
Bend, OR, 97702, United States
0.2k from Oregon Trail of Dreams center

Balcony, Dryer, Fireplace, Free Parking, Heater, Hot Tub, Internet, Kitchen, Laundry

1 Bedroom2 Guests
8.0

Good

1 reviews

$280
Average price / night
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Ski Condo 110 condo
Ski Condo 110 condo
Apartment
Bend, OR, USA
0.1k from Oregon Trail of Dreams center

Apartments, Accommodations, Pools, Parking, Lodgings, Hot tubs, Places to stay, Condos

1 Bedroom4 Guests
New to Booking
$432
Average price / night
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Alpine Studio at Mount Bachelor w/ Pool & Hot Tub
Alpine Studio at Mount Bachelor w/ Pool & Hot Tub
Apartment
Bend, OR, 97702, United States
0.2k from Oregon Trail of Dreams center

Heater, Hot Tub, Internet, Microwave, No Smoking, Pool, TV

1 Bedroom2 Guests
6.0

Review score

6 reviews

$155
Average price / night
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River Ridge 416B
River Ridge 416B
House
Bend, OR, USA
0.1k from Oregon Trail of Dreams center

Accommodations, Villas, Vacation homes, Cottages, Lodgings, Places to stay

1 Bedroom2 Guests
New to Booking
$344
Average price / night
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Snowcap Escape at Mount Bachelor w/ Pool & Hot Tub
Snowcap Escape at Mount Bachelor w/ Pool & Hot Tub
Apartment
Bend, OR, 97702, United States
0.3k from Oregon Trail of Dreams center

AC, Balcony, Barbecue, Dryer, Fireplace, Free Parking, Heater, Hot Tub, Internet

2 Bedrooms4 Guests
New to Booking
$357
Average price / night
Check Availability
River Ridge 416AB
River Ridge 416AB
House
Bend, OR, USA
0.1k from Oregon Trail of Dreams center

Accommodations, Villas, Vacation homes, Cottages, Lodgings, Places to stay

1 Bedroom6 Guests
New to Booking
$1010
Average price / night
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Cozy studio condo with free WiFi, shared pool & tennis, near river
Cozy studio condo with free WiFi, shared pool & tennis, near river
Apartment
Bend, OR, 97702, United States
0.3k from Oregon Trail of Dreams center

New to Booking
$196
Average price / night
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River Ridge 416A
River Ridge 416A
House
Bend, OR, USA
0.1k from Oregon Trail of Dreams center

Accommodations, Villas, Vacation homes, Cottages, Lodgings, Places to stay

1 Bedroom4 Guests
New to Booking
$472
Average price / night
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MBV 511 | Mt Bachelor Village Resort, river views new deck and hot tub
MBV 511 | Mt Bachelor Village Resort, river views new deck and hot tub
House
Bend, OR, 97702, United States
0.3k from Oregon Trail of Dreams center

AC, Barbecue, Dryer, Fireplace, Free Parking, Heater, Hot Tub, Internet, Kitchen

2 Bedrooms6 Guests
9.8

Exceptional

63 reviews

$302
Average price / night
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19 Mi to Mt Bachelor Ski Resort Condo with Grill
19 Mi to Mt Bachelor Ski Resort Condo with Grill
Apartment
Bend, OR, USA
0.1k from Oregon Trail of Dreams center

Apartments, Accommodations, Pools, Parking, Lodgings, Hot tubs, Places to stay, Condos

1 Bedroom4 Guests
New to Booking
$220
Average price / night
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SolAbode: A Luxury Retreat for All Seasons!
SolAbode: A Luxury Retreat for All Seasons!
House
Bend, OR, 97702, United States
0.4k from Oregon Trail of Dreams center

AC, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry

2 Bedrooms6 Guests
10.0

Exceptional

3 reviews

$320
Average price / night
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Ponderosa Vista - Resort Condo
Ponderosa Vista - Resort Condo
House
Bend, OR, USA
0.1k from Oregon Trail of Dreams center

Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Lodgings, Places to stay, Condos

1 Bedroom4 Guests
New to Booking
$204
Average price / night
Check Availability
Built 4 Fun - Hot Tub, Wifi, Westside on the way to Mt Bachelor
Built 4 Fun - Hot Tub, Wifi, Westside on the way to Mt Bachelor
House
Bend, OR, 97701, United States
0.4k from Oregon Trail of Dreams center

AC, Barbecue, Dryer, Fireplace, Heater, Hot Tub, Internet, Kitchen, Laundry

4 Bedrooms12 Guests
9.8

Exceptional

114 reviews

$533
Average price / night
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RiverView Hideaway - Trip for 2
RiverView Hideaway - Trip for 2
House
Bend, OR, USA
0.1k from Oregon Trail of Dreams center

Accommodations, Villas, Vacation homes, Cottages, Lodgings, Places to stay

1 Bedroom2 Guests
New to Booking
$206
Average price / night
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Bluebird Day - Wild River Getaway
Bluebird Day - Wild River Getaway
House
Bend, OR, 97702, United States
0.4k from Oregon Trail of Dreams center

AC, Dryer, Extra Bed, Fireplace, Heater, Internet, Kitchen, Laundry, Microwave

2 Bedrooms6 Guests
10.0

Exceptional

51 reviews

$463
Average price / night
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Hot-Tub - Picturesque 2 BDR in Resort
Hot-Tub - Picturesque 2 BDR in Resort
House
Bend, OR, USA
0.1k from Oregon Trail of Dreams center

Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Lodgings, Places to stay

2 Bedrooms4 Guests
New to Booking
$241
Average price / night
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Bluebird Day - River Trail House
Bluebird Day - River Trail House
House
Bend, OR, 97702, United States
0.4k from Oregon Trail of Dreams center

AC, Dryer, Extra Bed, Fireplace, Heater, Internet, Kitchen, Laundry, Microwave

2 Bedrooms6 Guests
10.0

Exceptional

39 reviews

$244
Average price / night
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Bluebird Day - Big River
Bluebird Day - Big River
House
Bend, OR, 97702, United States
0.5k from Oregon Trail of Dreams center

AC, Dryer, Fireplace, Heater, Hot Tub, Internet, Kitchen, Microwave, No Smoking

4 Bedrooms8 Guests
10.0

Exceptional

7 reviews

$812
Average price / night
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Big Pine - Community Hot Tub, Launch for Adventure, On River Trail, Ski/Drying Rack
Big Pine - Community Hot Tub, Launch for Adventure, On River Trail, Ski/Drying Rack
House
Bend, OR, 97702, United States
0.5k from Oregon Trail of Dreams center

AC, Barbecue, Dryer, Fireplace, Free Parking, Heater, Hot Tub, Internet, Kitchen

3 Bedrooms8 Guests
9.8

Exceptional

108 reviews

$412
Average price / night
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Winter Wren 2 | River Wild Mt Bachelor Village Resort
Winter Wren 2 | River Wild Mt Bachelor Village Resort
House
Bend, OR, 97702, United States
0.5k from Oregon Trail of Dreams center

AC, Barbecue, Crib, Dryer, Fireplace, Free Parking, Heater, Hot Tub, Internet

4 Bedrooms10 Guests
10.0

Exceptional

75 reviews

$457
Average price / night
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Minutes to Deschutes River Trail with Hot Tub & Fire Pit!
Minutes to Deschutes River Trail with Hot Tub & Fire Pit!
House
Bend, OR, 97702, United States
0.5k from Oregon Trail of Dreams center

AC, Balcony, Barbecue, Crib, Dryer, Fireplace, Free Parking, Heater, Hot Tub

2 Bedrooms6 Guests
10.0

Exceptional

107 reviews

$491
Average price / night
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Big Canyon - Elegant & Spacious, 3 Master King Suites! Community Hot Tub (and Seasonal Pool)
Big Canyon - Elegant & Spacious, 3 Master King Suites! Community Hot Tub (and Seasonal Pool)
House
Bend, OR, 97702, United States
0.5k from Oregon Trail of Dreams center

AC, Barbecue, Dryer, Fireplace, Free Parking, Heater, Hot Tub, Internet, Kitchen

4 Bedrooms10 Guests
9.8

Exceptional

81 reviews

$554
Average price / night
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2BR/2BA Cottage - Home Base for Outdoor Adventures
2BR/2BA Cottage - Home Base for Outdoor Adventures
House
Bend, OR, 97702, United States
0.5k from Oregon Trail of Dreams center

AC, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry

2 Bedrooms4 Guests
10.0

Exceptional

74 reviews

$223
Average price / night
Check Availability
Beautiful Home with Deck, Shared Pool and Hot Tub - Near the Slopes
Beautiful Home with Deck, Shared Pool and Hot Tub - Near the Slopes
House
Bend, OR, 97701, United States
0.6k from Oregon Trail of Dreams center

3 Bedrooms8 Guests
9.4

Superb

91 reviews

$319
Average price / night
Check Availability

Pro Tip:
VacationByOwnerRentals aggregates the best inventory from leading travel sites, including Booking.com, Agoda.com, Expedia.com, Vrbo.com, and Airbnb.com. Use our Advanced Filters to compare verified homes, villas, cabins, condos, cottages, vacation rentals, hotels, and eco-friendly stays. Our goal is to help you find the absolute best Vacation Rentals in Oregon Trail of Dreams.

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Frequently Asked Questions

You can explore 1143 verified vacation rentals in Oregon Trail of Dreams. Our listings are sourced from a range of trusted providers, giving you access to a wide selection of private homes, apartments, and unique stays—all in one place.

Vacation rental prices in Oregon Trail of Dreams vary depending on the season, property size, and location. Rates typically start from around $109 per night, with higher prices for larger homes or peak travel periods. Comparing available options can help you find a stay that matches both your budget and travel plans.

Most vacation rentals in Oregon Trail of Dreams include fully equipped kitchens, making it easy to prepare meals and enjoy a more flexible stay. This is especially useful for families, longer stays, or travelers who prefer a home-like experience.

Yes, many vacation rentals in Oregon Trail of Dreams welcome pets. Currently, 23 listings allow pets, although specific policies may vary by property. You can filter for pet-friendly options to quickly find suitable accommodations.

For popular travel periods such as holidays or peak seasons, it’s recommended to book your vacation rental 60 to 90 days in advance to secure the best options. During quieter times, you may still find good availability closer to your travel dates.

Vacation rentals in Oregon Trail of Dreams often include amenities such as Fireplace/Heating, Wellness Facilities, and Hot Tub. These features provide added comfort and convenience, making them a popular choice for travelers seeking more space and privacy.

You can use filters to narrow down your search by criteria such as number of bedrooms, guest ratings, or specific amenities like private pools or beachfront access. This makes it easier to find a property that fits your exact needs and preferences.