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Maupin Flight + Hotel Packages

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

Sugarloaf Mt Motel

2 out of 5
per person
Jul 13 - Jul 17
found 8 hours ago
Roundtrip flight included
Chicago (ORD) to Redmond (RDM)
Stay at this motel in Bend. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Hayden Homes Amphitheater and Old Mill District are located nearby.
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
Save 100% on your flight
per person
Jul 22 - Jul 24
found 22 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to Redmond (RDM)
Stay at this 3.5-star business-friendly villa in Bend. Enjoy free parking, a sauna, and patios. Popular attraction Aspen Lakes Golf Course is located nearby.
Riverhouse Lodge

Riverhouse Lodge

3.5 out of 5
per person
Jul 22 - Jul 24
found 22 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to Redmond (RDM)
Stay at this 3.5-star business-friendly resort in Bend. Enjoy an outdoor pool, breakfast (surcharge), and room service. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Hayden Homes Amphitheater and Old Mill District are located nearby.
Ski Inn Taphouse Hotel

Ski Inn Taphouse Hotel

2.5 out of 5
per person
Jul 22 - Jul 24
found 22 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to Redmond (RDM)
Stay at this hotel in Sisters. Enjoy free WiFi, free parking, and satellite TV channels. Popular attractions Village Green Park and Cliff Clemens Park are located nearby.
The Lodge at Eagle Crest Resort

The Lodge at Eagle Crest Resort

3.5 out of 5
per person
Jul 22 - Jul 24
found 21 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to Redmond (RDM)
Stay at this 3.5-star spa resort in Redmond. Enjoy free WiFi, free parking, and 3 outdoor pools. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Eagle Crest Golf Courses and Eagle Ridge Sports Center and Spa are located nearby.
Heritage by Avantstay Luxe Oregon Retreat + Deck

Heritage by Avantstay Luxe Oregon Retreat + Deck

3 out of 5
per person
Jul 22 - Jul 24
found 22 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to Redmond (RDM)
Stay at this 3-star cottage in Powell Butte. Enjoy free parking, patios, and in-room washers/dryers.
The Aerie Suites by AvantStay – Modern Comfort with Mountain Views

The Aerie Suites by AvantStay – Modern Comfort with Mountain Views

3 out of 5
per person
Jul 22 - Jul 24
found 22 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to Redmond (RDM)
Stay at this 3-star apartment in Bend. Enjoy free WiFi, free parking, and in-room washers/dryers. Popular attractions Hayden Homes Amphitheater and Old Mill District are located nearby.
SCP Hotel Redmond

SCP Hotel Redmond

3.5 out of 5
per person
Jul 22 - Jul 24
found 21 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to Redmond (RDM)
Stay at this 3.5-star eco-certified hotel in Redmond. Enjoy free WiFi, free parking, and a rooftop terrace. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Redmond Lockers and Custom Meats and Redmond Caves Recreation Area are located nearby.

Maupin Vacation Packages 3-4 Night Stays

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

Sugarloaf Mt Motel

2 out of 5
Boyd Acres
per person
Jul 13 - Jul 17
found 8 hours ago
Roundtrip flight included
Chicago (ORD) to Redmond (RDM)
The Lodge at Eagle Crest Resort

The Lodge at Eagle Crest Resort

3.5 out of 5
per person
Jul 13 - Jul 17
found 8 hours ago
Roundtrip flight included
Chicago (ORD) to Redmond (RDM)
Red Lion Inn & Suites Deschutes River Bend

Red Lion Inn & Suites Deschutes River Bend

2.5 out of 5
Boyd Acres
per person
Jul 13 - Jul 17
found 8 hours ago
Roundtrip flight included
Chicago (ORD) to Redmond (RDM)
LOGE Bend

LOGE Bend

3 out of 5
Century West
per person
Jul 13 - Jul 17
found 8 hours ago
Roundtrip flight included
Chicago (ORD) to Redmond (RDM)

Top Flight Deals

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Frontier Airlines
Tue, Aug 12 - Sat, Aug 16
ONT
Los Angeles - Ontario Intl.
PDX
Portland Intl.
$109 Roundtrip, found 18 hours ago
$109
Roundtrip
found 18 hours ago
Select Frontier Airlines flight, departing Tue, Aug 12 from Los Angeles - Ontario Intl. to Portland Intl., returning Sat, Aug 16, priced at $109 found 18 hours ago
Spirit Airlines
Tue, Jul 8 - Tue, Jul 8
LAX
Los Angeles Intl.
PDX
Portland Intl.
$114 Roundtrip, found 1 day ago
$114
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Tue, Jul 8 from Los Angeles Intl. to Portland Intl., returning Tue, Jul 8, priced at $114 found 1 day ago
Frontier Airlines
Mon, Jul 28 - Fri, Aug 1
SFO
San Francisco Intl.
PDX
Portland Intl.
$119 Roundtrip, found 21 hours ago
$119
Roundtrip
found 21 hours ago
Select Frontier Airlines flight, departing Mon, Jul 28 from San Francisco Intl. to Portland Intl., returning Fri, Aug 1, priced at $119 found 21 hours ago
Spirit Airlines
Tue, Jul 29 - Thu, Aug 7
SAN
San Diego Intl.
PDX
Portland Intl.
$132 Roundtrip, found 19 hours ago
$132
Roundtrip
found 19 hours ago
Select Spirit Airlines flight, departing Tue, Jul 29 from San Diego Intl. to Portland Intl., returning Thu, Aug 7, priced at $132 found 19 hours ago