Plan a Cozy Winter Couples Trip to Sisters, Oregon Destination

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cozy couple by fireplace

 

Where to cozy up in Sisters



For the quintessential romantic retreat, book your stay at the highly recommended FivePine Lodge & Cabins. With over 1,000 reviews on TripAdvisor, the establishment holds a five-star average rating. The various cabins — nestled in a gorgeous pine forest — have a rustic atmosphere and cozy feel. An ideal pick for couples, the romance cabin features a sunken tile soaking tub planted right next to a stone gas fireplace. Head to FivePine’s Shibui Spa for extra relaxation with your significant other. Nothing says romance like a luxurious massage and a glass of champagne.

Alternatively, stay at The Cottage Inn at Sisters, a charming boutique hotel with six farmhouse-style cottages. In addition to the gas fireplaces inside the rooms, an outdoor area has a fire pit. One reviewer on TripAdvisor gushed, “Our stay at the Cottage Inn was phenomenal! We just returned from three days of being pampered in this delightful bed and breakfast.” They added, “They have taken care of every detail, from the luxurious bed linens to the fresh morning breakfast delivered in a cute little picnic basket.” This hidden gem has also been lauded for its walkability to local restaurants and shops.

Enjoy these wintry activities

snow in Sisters Oregon

Explore Sisters’ magnificent wintry scenery by heading out to the slopes. With over 800 acres of terrain and an average snowfall of 450 inches per year, Hoodoo Ski Area is a prime recreation destination that provides incredible chills and thrills. At this renowned ski resort, you can partake in Nordic skiing and tubing. As the only ski spot in Central Oregon to offer night skiing, Hoodoo is a unique destination for couples seeking an intimate adventure at twilight.



Grab a cup of hot cocoa and spend the afternoon wandering around downtown Sisters, a delightful area that exudes old-timey Western charm. Inspired by the 1880s, this quaint district includes several shops that sell clothing, home décor, and various vintage items. In addition, local galleries and public art installations will give you and your love some insight into the town’s rich cultural scene.

Later, take a break from all the physical activity and enjoy a film screening at the Sisters Movie House. With its rustic barn-esque exterior, this indie playhouse isn’t your typical movie theater chain. Once you step in, you can order from the theater’s café and enjoy a full meal at your seat. This will make for a classic and cozy date night!

Dave Pennells

By Dave Pennells

Dave Pennells, MS, has contributed his expertise as a career consultant and training specialist across various fields for over 15 years. At City University of Seattle, he offers personal career counseling and conducts workshops focused on practical job search techniques, resume creation, and interview skills. With a Master of Science in Counseling, Pennells specializes in career consulting, conducting career assessments, guiding career transitions, and providing outplacement services. Her professional experience spans multiple sectors, including banking, retail, airlines, non-profit organizations, and the aerospace industry. Additionally, since 2001, he has been actively involved with the Career Development Association of Australia.