How to Plan a Holiday Gathering At A Bend Holiday Vacation Rental

How to Plan a Holiday Gathering at a Vacation Home in Central Oregon

🎄 How to Plan a Holiday Gathering at a Bend Holiday Vacation Rental 🎄

The holidays are about spending time with the people who matter most, and what better way to do that than by gathering in a cozy Bend holiday vacation rental? Whether you’re hosting Thanksgiving, Friendsgiving, or a pre-holiday family getaway in December, our homes offer the perfect blend of comfort, space, and seasonal charm. Here’s how to make your holiday gathering stress-free and memorable.

1. Choose the Right Home for Your Group

The first step to planning a great holiday gathering is finding the right home base. Look for a Bend holiday vacation rental with:

• Plenty of seating and dining space for shared meals
• Fully equipped kitchens with double ovens or large prep areas
• Multiple bedrooms or suites so everyone has space to retreat
• Cozy extras like fireplaces and hot tubs for relaxing evenings

Pro Tip: Our larger homes, like  Cooper's Rest Getaway and  Lone Pine Lodge, are designed with groups in mind, offering spacious kitchens and multiple master suites. For more options, see our full list of  vacation rentals for large groups.

2. Plan a Memorable Holiday Meal

Cooking together is part of the fun! Before your trip, plan your menu and divide up responsibilities—have one person bring appetizers, another dessert, and someone else handle the turkey or main dish. Many local markets in Bend and Sunriver also offer pre-made sides and pies, making it easier to focus on the gathering itself.

Pro Tip: Shop early at Newport Avenue Market in Bend or Sunriver Country Store for local ingredients and holiday treats.

3. Add Festive Touches

Make your Bend holiday vacation rental feel extra special with a few holiday details. Bring a box of simple décor—think candles, string lights, or even a tabletop Christmas tree. For Thanksgiving or Friendsgiving, a few pumpkins and seasonal florals make the table feel festive without too much fuss. If your family has traditions like matching pajamas or a favorite holiday playlist, bring them along to make the trip feel personal.

4. Plan Activities Beyond the Meal

A holiday getaway is about more than just the feast. Here are some favorite ways to make memories together:

• Build a snowman or have a lighthearted snowball fight right outside your rental (if the weather cooperates).
• Go ice skating at The Pavilion in Bend or the Village Ice Rink in Sunriver.
• Plan a family game night with classics like charades, Pictionary, or card games.
• Take a group hike at Shevlin Park, along the Deschutes River Trail, or enjoy another of the best winter hikes in Central Oregon for crisp air and winter scenery.
• Start a new family tradition—like baking cookies together, hosting a gingerbread house contest, or swapping handwritten notes of gratitude.
• End the night with a movie marathon, cozy blankets, and hot cocoa or mulled wine.

You don't have to go far to make memories that last. You can enjoy all of these activities at or in close proximity to your Bend holiday vacation rental.

🎁 Enjoy Festive Activities Around Central Oregon

Central Oregon comes alive with holiday cheer in November and December. Add one of these local favorites to your getaway:

• Holiday Lights Paddle Parade (Bend, early December): Watch paddlers float down the Deschutes River in boats decked out with sparkling lights—a true Bend tradition.
• Bend Christmas Parade (early December): Downtown Bend glows with marching bands, floats, and plenty of holiday spirit.
• Ugly Sweater Run (Bend, mid-December): A fun and festive run through downtown—perfect if your group loves quirky traditions.
• Schilling’s Garden Market Holiday Market (Bend, weekends in December): Shop for handmade gifts, local crafts, and holiday treats in a cozy market setting.
• Redmond Starlight Parade & Bend Tree Lighting: Classic small-town events to kick off the season with twinkling lights and carols.

Find more of our favorite holiday activities in Central Oregon in our holiday guide.

5. Don’t Forget Downtime

While it’s tempting to pack the schedule full, leave room for simple moments: coffee and pastries in the morning, curling up with a good book by the fire, or soaking in the hot tub under a sky full of stars. Sometimes the quietest memories end up being the most meaningful.

✨  Make Your Holiday Gathering Easy with Our Lodging Specials

Embrace the season in Central Oregon with savings designed for family and friend getaways:

🦃 Thanksgiving Special
Stay 5 nights or more November 21 – 30 and save 15%

🍂 Fall Special
Stay 4 nights or more from September 1 – November 16 and save 15%

❄️ Winter Special
Stay 4 nights or more from January 20 – March 20 and save 15%

From Thanksgiving feasts to Friendsgiving fun, our Bend holiday vacation rentals provide the space, comfort, and charm to bring everyone together. Start planning your holiday gathering today and make this season one to remember.

👉  Browse Holiday-Ready Vacation Homes In Bend & Book Direct Here