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2018 Winter Getaway to Ashland
Discover a year-round paradise, as you like it. Enter to win your paradise vacation in Ashland, Oregon.

Relax and indulge here this winter. Nestled between coastal and volcanic mountain ranges in Southern Oregon lies the vibrant town of Ashland. In this amazingly beautiful setting, you will taste award-winning wines, experience Mt. Ashland at 7600’, enjoy delicious meals created by talented chefs, be pampered at the spa and rest up for more fun at one of Ashland’s fine lodging spots.



Enter online HERE and begin by typing in your age. 

2018 Getaway Prizes:



Two Night Stay at the beautiful,
Country Willows Bed & Breakfast


Country Willows Inn is proud to offer the most exceptional boutique country inn experience in Southern Oregon. Country Willows Inn offers both suites and rooms, all beautifully appointed in a country elegant decor. The 5-acre historic property is nestled on a secluded hillside just 2 miles from downtown, with stunning mountain views, a heated pool, and walking paths meandering past the gazebo, trickle stream, and koi ponds, duck pond, and waterfalls. Guests also enjoy the miles of hiking trails accessible right from the grounds. In the summertime, Country Willows Inn offers live music concerts in the gardens with complimentary hors d'oeuvres and refreshing drinks. Visit Country Willows Inn, Ashland's most exceptional boutique inn!

Country Willows Bed & Breakfast 
1313 Clay Street
Ashland, OR 97520
Follow Country WillowsFacebook  


Two Mt. Ashland Lift Tickets


The Mt. Ashland Ski Area is located in beautiful Southern Oregon at the highest point in the Siskiyou Mountain Range. They offer skiing and snowboarding on 220 acres, with 4 chair lifts and 23 runs. They have a full rental shop (which offers ski and snowboard rentals and tuning), retail shop, and ski school. Their historic Lodge also features a full-service Café and Bar. With average snowfall over 265″, it’s been the place for Local Mountain Fun since 1964.  In Spring and Summer months, the Mountain is the perfect oasis for hikers, bikers, outdoor and birding enthusiasts.

Mt. Ashland
11 Mt. Ashland Ski Rd.
Ashland, OR 97520
541-482-2897 or call the Snow Phone: 541-482-2754
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A 60 minute Side by Side Massage (for two)
at the Blue Giraffe Day Spa Salon


The Blue Giraffe is a beautiful boutique spa and salon located just a few blocks from downtown Ashland. The Blue Giraffe offers both classic and contemporary spa therapies including massage, chiropractic, facials, hair styling, nail care, body treatments, waxing and more. The Blue Giraffe has been voted Ashland’s Best Spa in the The Sneak Preview’s reader’s choice awards since 2005.

Blue Giraffe Day Spa Salon 
51 Water Street
Ashland, OR 97520
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$50 Gift Certificate for Alchemy Restaurant & Bar

Serving dinner, bistro fare and brunch, Alchemy Restaurant and Bar offers cuisine transformed. We specialize in fresh local ingredients, craft cocktails and boutique wines all lovingly selected and prepared by our executive chef, Chaz McKenna, and Certified Sommelier, Drew Gibbs.
Alchemy Restaurant & Bar  
35 S. Second Street
Ashland, OR 97520
Follow Alchemy
- Twitter / Facebook / Instagram


Two 'Perfect Pairings' (a Food & Wine Tasting) and Private Tour for two at Irvine & Roberts Vineyards

The Irvine & Roberts families bring a unique collection of skills and passions to create their ultra-premium, artistically crafted wines produced in a style that evokes elegance, balance, and richness in their flavors and texture. The estate vineyard is an exceptional example of geology and climate that provides the perfect growing conditions for some of the world’s most complex grapes: Pinot noir and Chardonnay. Nestled between the Southern Cascade and Siskiyou Mountain Ranges, our ancient soils are some of the oldest in North America and are located on steep, high-elevation hillsides with glowing morning sun and shady, breezy afternoons. Located just 5 miles from the heart of downtown Ashland and the Oregon Shakespeare Festival, our Tasting Room offers stunning views of our estate vineyards and the surrounding Southern Cascade and Siskiyou Mountain Ranges. The team at Irvine & Roberts Vineyards looks forward to sharing the story of the vineyard and wines with you. Tasting Room Hours are Wednesday – Sunday from 12pm-6pm.

Prize Description
: Before taking a seat at their open intimate kitchen, you'll enjoy a private guided tour of our winery facility with a splash of our Award Winning 2016 Rose of Pinot Noir and then enjoy a curated tasting of three of our very limited Reserve and Single Block Pinot Noir wines alongside our chef’s small plate pairings. Please allow 90-120 minutes.

Irvine & Roberts Vineyards
1614 Emigrant Creek Road
Ashland, OR 97520
Follow Irvine
- Twitter / Facebook / Instagram


Two Tickets to see a performance at the Oregon Shakespeare Festival & a Backstage Tour for Two


Founded in 1935, the Tony Award-winning Oregon Shakespeare Festival (OSF) is among the oldest and largest professional non-profit theatres in the nation. Each year OSF presents an eight-and-a-half-month season of eleven plays in three theatres plus numerous ancillary activities, and undertakes an extensive theatre education program.

OSF welcomes you to their 2018 season of eleven plays and musicals!
You may view their 2018 Schedule

Depending on ticket availability and trip dates, the winner may enjoy a performance of Othello, Sense and Sensibility, Destiny of Desire, Henry V, Manahatta and 'Rodgers and Hammerstein's Oklahoma!'.

Oregon Shakespeare Festival
15 S. Pioneer Street
Ashland, OR 97520 
Follow OSF
- Twitter / Facebook / Instagram 



$50 Destination Ashland Gift Certificate



Enjoy a $50 Destination Ashland Gift Certificate which can be used at over 40 locations throughout Southern Oregon, including 24 local restaurants.  

Participating restaurants where they can be redeemed: Alchemy Restaurant & Bar, Ashland Food Co-op, Black Sheep, Brickroom, Brothers', Greenleaf, Hearsay, Jacksonville Inn, Larks Restaurant (Ashland), Liquid Assets, Luna Cafe, Mihama Teriyaki Grill, NW Raw, Oberson's, Omar's, Ostras! Tapas & Bottleshop, Peerless Restaurant, Pie + Vine, Plancha, Porters, Sesame, Smithfields, Smithfields Pub & Pies and Standing Stone.

These Gift Certificates help support our local businesses and provide you with another wonderful reason to shop-local and explore our beautiful town while visiting. They make great gifts for the holidays, for those traveling to Ashland and for any special occasions throughout the year.

Ashland Chamber of Commerce & Travel Ashland
110 East Main Street (PO Box 1360)
Ashland, OR 97520

Follow Travel Ashland - Twitter / Facebook / Instagram  

Details to Enter:

  • One entry per person. Entry deadline is Sunday, February 4th, 2018 at 11:59pm (Pacific time).

  • Drawing to be held that following week and winner to be contacted by February 9th, 2018.

  • The contest is open to all persons who are 21 years of age or older.

  • All items of this package are based on availability. 

  • The Winner is solely responsible and required to make their own reservations.

  • The Winner is responsible for calling to schedule tours and booking services. 

  • All vouchers must be redeemed PRIOR to May 1st, 2018.

  • Some items are weather dependent and subject to change.

  • Vouchers for the package will be provided to winners.

  • Winners are required to follow directions and understand restrictions on each voucher provided.

  • All entries are considered “opt in” for email communication.  Entrants agree to have their email addresses added to the Ashland Visitor and Convention (Travel Ashland) Bureau newsletter email list and those newsletters of participating entities.

Photos provided by each participant unless otherwise noted.

Produced by Travel Ashland

For questions, email Kelsey Frantz -

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