Published October 6, 2020 10/6/2020

Top 12 Vacation Rentals in Bend, Oregon for the Holidays

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Bend, Oregon is a charming town full of historic homes and structures, offering a long list of things to do. During the holidays, you can do some shopping at The Bend Soap Company (because they have the best goat milk lotion), or sip a warm beverage from the Looney Bean. Those visiting will also be treated to views of the Deshutes River and an abundance of outdoor recreation. So if you are coming to the area for the holidays, these rentals will make your spirits bright.

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Dome Sweet Dome Dome Sweet Dome
Credit: Airbnb.com
Dome Sweet Dome

Dome Sweet Dome

An out-of-the-box holiday awaits at this obscurely shaped yet super cozy structure near the Deschutes River. One of the best dome Airbnbs in the United States, its geodesic design has an otherworldly appeal, and charming interiors. So much of what Bend has to offer is either a walk or a bike ride from this location. The hosts do note that there could be some safety concerns for super little children. So maybe this is a yuletide getaway for older kiddos and grown-ups.

Skyliners Getaway Skyliners Getaway
Credit: Airbnb.com
Skyliners Getaway

Skyliners Getaway

Are you dreaming of a traditionally rustic Christmas? That’s exactly what this wooden, simplistic cabin offers. Guests will find all the essentials but keep in mind that the bathroom is detached, but fully equipped. Situated amongst trees, all of the area’s outdoor excitement is right there.

Modern, River, Old Mill near Downtown Modern, River, Old Mill near Downtown
Credit: airbnb.com
Modern, River, Old Mill near Downtown

Modern, River, Old Mill near Downtown

Being brand new, a different type of endearing appeal is found at this cabin, rather than those older more aged aesthetics. However, local craftsmen helped build the house with reclaimed materials which gives the space an enriching look that rivals the most historic structures. The Old Mill District, where you will find part of Bend’s brewery and wine scene is literally right outside.

Little Red Little Red
Credit: Airbnb.com
Little Red

Little Red

Will this holiday getaway be just you and your sweetheart? Then this tiny house is perfection. Built by the hosts themselves, plenty of Bend’s famous sunshine comes through the abundance of windows. A local beer awaits in the fridge as a welcoming treat, and there is a boot and gloves dryer for your use after a day on the slopes.

Broadway Rustic Cottage Retreat Broadway Rustic Cottage Retreat
Credit: Airbnb.com
Broadway Rustic Cottage Retreat

Broadway Rustic Cottage Retreat

Warm up by the gas fireplace of this Airbnb plus after a day snowshoeing, skiing or building Frosty the Snowman. Enjoy a meal cooked with ingredients from the nearby Trader Joe’s in the bright kitchen. Or maybe even make some cookies and grab some local brews! The exterior of this bungalow is particularly adorable when dusted with powdery snow.

Bluebird Day, Deschutes Bungalow Bluebird Day - Deschutes Bungalow - Walk Everywhere - Westside - Bikes
Credit: Airbnb.com
Bluebird Day - Deschutes Bungalow - Walk Everywhere - Westside - Bikes

Bluebird Day, Deschutes Bungalow

Built years ago when Bend was thriving as a mill town, this home exudes that classic craftsman detail. Today it has been upgraded and renovated to be luxurious and modern but still quite homey. Families can enjoy a traditional Christmas while having the option of exploring a number of adorable local restaurants and coffee shops. A hot tub is included on the deck!

Romantic Guest House with Hot Tub, Pool & Tennis Romantic Guest House with Hot Tub, Pool & Tennis
Credit: Airbnb.com
Romantic Guest House with Hot Tub, Pool & Tennis

Romantic Guest House with Hot Tub, Pool & Tennis

Wooden ceilings, cabinets, and floors add that woodsy Christmas magic. And a wood-burning stove is the most adorable addition, that’s also practical, to the living space. Outback is a beautiful hot tub and deck space. From the home, Bend’s famous volcanic mountains can be seen.

Mountain Modern Quiet Getaway for Families Mountain Modern Quiet Getaway for Families
Credit: airbnb.com
Mountain Modern Quiet Getaway for Families

Mountain Modern Quiet Getaway for Families

You might just decide to buy a home in Bend after staying in this traditional family dwelling. The open concept is met with amenities such as a lovely fireplace and washer and dryer. Guests will be situated amongst local bakeries and shops while being a short drive from the ski resort at Mount Bachelor.

Adorable West Side Cottage Adorable West Side Cottage, Great Location
Credit: Airbnb.com
Adorable West Side Cottage, Great Location

Adorable West Side Cottage

A sense of chic flows through this restored home. However, much of the cottage’s history has been preserved through aesthetics such as exposed brick. Enjoy a clawfoot tub, plush bedding, and absolutely glistening wooden floors. Walk to nearby coffee shops in the morning for a taste of the city’s mouthwatering cafe culture.

Romantic Luxury Cabin, Private Hot Tub on Tumalo Lake Romantic Luxury Cabin/Home, private hot tub on Tumalo Lake in Bend Oregon
Credit: VRBO.com
Romantic Luxury Cabin/Home, private hot tub on Tumalo Lake in Bend Oregon

Romantic Luxury Cabin, Private Hot Tub on Tumalo Lake

Imagine waking up to a snow-dusted Tumalo lake, viewable from your luxurious cabin rental. How cozy does it sound to sit around the wood-burning stove with your morning cup of coffee or hot chocolate accented with a candy cane? While presenting extravagantly, this is just another snug abode to enjoy the holidays within.

Rustic Ranch Cottage with Trails Near Bend Rustic Ranch Cottage w/ Trails - 13 Mi to Bend
Credit: VRBO.com
Rustic Ranch Cottage w/ Trails - 13 Mi to Bend

Rustic Ranch Cottage with Trails Near Bend

Being about 13 miles from the center of Bend, this bunkhouse offers a bit more seclusion. And the kids would likely love the saloon themed exterior. However, this continues more subtly inside. Staying here adds a twist of fun to any holiday getaway, and outdoors you will find scenic trails and acres to explore.

Inn Wildness - A Cozy 1924 Cottage on Bend's Westside Inn Wildness - A Cozy 1924 Cottage on Bend's Westside
Credit: VRBO.com
Inn Wildness - A Cozy 1924 Cottage on Bend's Westside

Inn Wildness - A Cozy 1924 Cottage on Bend's Westside

Bend has loads of adorable renovated homes, just like this one. We love that the original rustic-ness has been left intact. From the wood-burning stove to the eclectic kitchen, guests will have the perfect old fashioned Christmas in Bend, Oregon.

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