Spend Thanksgiving weekend appreciating family, food, and the beautiful landscape of the West Coast at a cozy vacation rental in Oregon. For activities and dining galore, book a stay in Portland and enjoy spectacular festivities. If you’re looking to get away from the hustle and bustle of the city, the Oregon Coast is home to small towns that boast big hearts and delicious local food. Mount Hood is ideal for those seeking an outdoorsy way to spend the long weekend. Take a look at the top places to stay at in Oregon this Thanksgiving.

1. Enjoy Family Fun in Portland

Stay at a Portland vacation rental over the Thanksgiving weekend, and take advantage of kid-friendly shows at the Clinton Street Theater. If you plan to do some Black Friday shopping, make it fun for the whole family by visiting Bridgeport Village, where Black Friday activities include prize giveaways, holiday-themed music, and fun themed mascots to greet the kids. While in town, gear up for Christmas at the Macy’s Holiday Parade, which usually takes place at the end of the Thanksgiving weekend.

Find vacation rentals near Portland

2. Get Outdoors at Mount Hood

If you’re looking to squeeze in some last outdoor activities before winter takes hold, book a stay at Mount Hood. Take advantage of resort-town amenities and dining, then bundle up and take a hike to enjoy stunning views of autumnal trees and mountainous vistas. Book a table at Cooper Spur Mountain Resort to enjoy a hot, multi-course Thanksgiving meal after your outdoor excursion. If you’re lucky and snow has already begun to fall on the slopes, book a weekend ski camp or a lesson to get a jump start on the winter sports season.

Find vacation rentals near Mount Hood

3. Gear Up for the Holidays in Jacksonville

The historic town of Jacksonville is a perfect spot to experience the best of the holiday season. Kick off your Thanksgiving with a delicious dinner in town at a restaurant like the Schoolhaus Brewhaus, an authentic Bavarian-style eatery within the town. The historic architecture of downtown Jacksonville will put you in a Holiday mood as you browse local shops and boutiques to get a jump on your gift-buying. If you book a stay for the whole weekend, experience the beginning of Victorian Christmas with a tree-lighting ceremony that takes place on the Saturday following Thanksgiving.

Find vacation rentals near Jacksonville

Find the perfect Oregon vacation rental on Tripping.com. Tripping.com is the world's #1 vacation rental search engine with over 10 million properties!

4. Explore the Wonders of Eugene

Thanksgiving is the perfect time to check out Oregon’s picturesque city of Eugene. Book a vacation rental in this nature-loving city to enjoy views and water activities on the Willamette River. Afterward, take a stroll through the historic Fifth Street Public Market to shop at small local businesses, and grab a bite to eat at a quaint diner or eatery. Take a hike at Alton Baker Park, which is home to plenty of trails.

Find vacation rentals near Eugene

5. Get a Jump on Holiday Shopping at Bend

The town of Bend offers plenty in the way of Thanksgiving celebration. Head to the Old Mill District to browse shops and boutiques selling everything from handmade foods, spices, and soaps, to clothing and kitchenware. If your vacation rental offers cooking amenities, pick up all the ingredients you need to make a wonderfully memorable Thanksgiving feast. Or, have an expert chef do the cooking for you at one of the Sunriver Resort Thanksgiving buffet options.

Find vacation rentals near Bend

6. Stay Active at Coos Bay

Just because it’s Thanksgiving doesn’t mean you can’t fit in a little workout for a good cause. Stay in Coos Bay and participate in the annual Thanksgiving Turkey Trot Fun Run around the Empire Lakes. Bring a couple of canned food items to pay for your entry and help those less fortunate during the holidays. The event is friendly to runners and walkers of all ages, and participants can choose their own goal distance.

Find vacation rentals near Coos Bay

7. Experience Bright Lights at Shore Acres

Just west of Coos Bay, Shore Acres State Park is home to picturesque views of the Oregon Coast, not to mention well-maintained botanical gardens, a Japanese lily pond, and more communal green space. Visit during the Thanksgiving long weekend to experience the Holiday Lights, an annual celebration beginning during the long weekend, in which hundreds of thousands of LED lights are strung up in the trees and plants, creating a sparkling, family-friendly wonderland. Stop at the Open Garden House for fresh apple cider, hot cocoa, and baked treats.

Find vacation rentals near Shore Acres

8. Relax at Cannon Beach

Take a few days to get away from all your stresses this Thanksgiving holiday, by booking a vacation rental in Cannon Beach. With plenty of hotels and amenities situated right along the beach, this quaint town is a renowned as a summer getaway, but still offers great walking, shopping, and views in the cooler months. Walk out onto the sand to see Haystack Rock, a large natural attraction in the area. Boutique shopping, art galleries, and home-style dining in town offer plenty of ways to pass the time.

Find vacation rentals near Cannon Beach

9. Spot Whales at Depoe Bay

Located along the central coast, Depoe Bay offers supreme whale watching opportunities. Autumn is one of the best times for spotting these majestic creatures just off the coast. Dine at Surfrider Restaurant or Samphire Restaurant to fuel up before your excursion, then take a drive out to Devil’s Punchbowl State Natural Arena to spot whales cresting off the coast. Be sure to stop by the Whale Watching Center in downtown Depoe Bay for more information about local whales.

Find vacation rentals near Depoe Bay

Ready to go? Check out these amazing Oregon vacation rentals on Tripping.com.