Exclusive Oregon Trail of Dreams Vacation Deals

Oregon Trail of Dreams vacation package deals

Price found within the past 48 hours. Click for updated prices.
Sugarloaf Mt Motel

Sugarloaf Mt Motel

2 out of 5
Boyd Acres
Price was $879, price is now $645 per person
$645
per person
Jul 26 - Jul 31
found 1 day ago
Roundtrip flight included
Portland (PDX) to Redmond (RDM)
This motel doesn't skimp on freebies - guests receive free on-the-go breakfast, free WiFi, and free self parking. If you want to take your pet along, this pet-friendly property offers everything you'll need for your pet including an off-leash area. There's a seasonal outdoor pool on site, and a 24-hour front desk and a convenience store are also provided.
Canyon Rim at Eagle Crest

Canyon Rim at Eagle Crest

4.5 out of 5
Save 100% on your flight
Price was $1,268, price is now $843 per person
$843
per person
Jul 26 - Jul 31
found 1 day ago
Roundtrip flight included
Portland (PDX) to Redmond (RDM)
A golf course, a full-service spa, and 2 hot tubs are all featured at this luxury condo. Enjoy the outdoor pool and perks like free WiFi. Enjoy the indoor pool and conveniences like a fireplace in the lobby and laundry facilities.
Ski Inn Taphouse Hotel

Ski Inn Taphouse Hotel

2.5 out of 5
Save 100% on your flight
Price was $1,411, price is now $1,000 per person
$1,000
per person
Jul 26 - Jul 31
found 1 day ago
Roundtrip flight included
Portland (PDX) to Redmond (RDM)
A restaurant and a bar/lounge are featured at this hotel. Guests will appreciate free perks like free self parking and WiFi in public areas. Luggage storage is also provided.
Big Sky by Avantstay Mountain Home w/ Great Views, Hot Tub, Al Fresco Dining

Big Sky by Avantstay Mountain Home w/ Great Views, Hot Tub, Al Fresco Dining

3.5 out of 5
River West
Save 100% on your flight
Price was $5,749, price is now $4,135 per person
$4,135
per person
Jul 26 - Jul 31
found 1 day ago
Roundtrip flight included
Portland (PDX) to Redmond (RDM)
A hot tub, free self parking, and concierge services are featured at this vacation home. WiFi in public areas is free. Barbecue grills are provided for your convenience.
Riverhouse Lodge

Riverhouse Lodge

3.5 out of 5
Boyd Acres
Save 100% on your flight
Price was $1,348, price is now $975 per person
$975
per person
Jul 26 - Jul 31
found 1 day ago
Roundtrip flight included
Portland (PDX) to Redmond (RDM)
This resort features a restaurant, an indoor pool, and a bar/lounge. If you want to take your pet along, this pet-friendly property offers everything you'll need for your pet including food and water bowls. There's a gym on site, and a 24-hour front desk and a coffee shop are also provided.
The Gem Estate by Avantstay Modern Farmhouse w/ Lavender Fields + Hot Tub

The Gem Estate by Avantstay Modern Farmhouse w/ Lavender Fields + Hot Tub

3.5 out of 5
Plainview
Save 100% on your flight
Price was $4,484, price is now $3,282 per person
$3,282
per person
Jul 26 - Jul 31
found 1 day ago
Roundtrip flight included
Portland (PDX) to Redmond (RDM)
This villa doesn't skimp on freebies - guests receive free WiFi and free self parking. A sauna and barbecue grills are also provided.

Frequently asked questions

How much are vacation packages to Oregon Trail of Dreams?
Save big on your visit to Oregon Trail of Dreams by combining your flights and hotel stay into a $645 package. With all that extra money in your pocket, why not stay longer and discover even more?
Where can I get the best vacation package deals for Oregon Trail of Dreams?
There's no need to look any further than Travelocity. With 400 partner airlines and 1,000,000 properties worldwide, it's a piece of cake to craft an Oregon Trail of Dreams package deal that suits your travel style.
Why should I book my Oregon Trail of Dreams vacation bundle with Travelocity?
From amazing destinations to fun experiences, we have everything you need to satisfy your travel desires. Our 24/7 support will also ensure you're being well taken care of while you're on your vacation. And don't fret if you notice a cheaper price on your booking, we'll match it. That's our Price Match Guarantee.

Top Oregon Trail of Dreams hotel deals

Hotel Peppertree Bend, BW Premier Collection

Hotel Peppertree Bend, BW Premier Collection

3.5 out of 5
1082 SW Yates Dr Bend OR
Free Cancellation
Reserve now, pay when you stay
$127 nightly
The price is $142 total per night
$142 total
May 10 - May 11
Total with taxes and fees
The hotel's indoor pool, 24-hour gym, and 2 bars/lounges are among the featured amenities. Enjoy a meal from the restaurant and perks like free full breakfast and free self parking. Enjoy the hot tub and conveniences like a 24-hour front desk and laundry facilities.
Pool
Hot Tub
Mt Bachelor Village Resort w pool and hot tub, remodeled

Mt Bachelor Village Resort w pool and hot tub, remodeled

Bend OR
A hot tub is featured at this condo, along with barbecue grills.
Pool
Hot Tub
Perfect Mt Bachelor Village Condo-Full Kitchen, Pool, Hot Tub & River Access!

Perfect Mt Bachelor Village Condo-Full Kitchen, Pool, Hot Tub & River Access!

Bend OR
$317 nightly
The price is $355 total per night
$355 total
May 6 - May 7
Total with taxes and fees
This condo features an outdoor pool and a gym. There's a hot tub on site, and laundry facilities and barbecue grills are also offered.
Pool
Hot Tub
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.