A Bend vacation gives visitors the chance to experience four seasons of adventure! iTrip Vacations Bend manages rentals near snow-capped mountains, rivers, hiking and biking trails, golf courses, and more.

Named among Outside Magazine's 50 Trips of a Lifetime, Bend offers a mountain retreat complete with a vibrant downtown and friendly locals. No matter what time of year, the area's landscape welcomes guests to enjoy the great outdoors and small-town culture.

Winter brings an average of 30 feet of snow to the mountains surrounding Bend. Ski and snowboard at Mt. Bachelor Ski Resort, go dog-sledding, rent snowmobiles and fatbikes, and take guided snowshoe tours. Snow bunnies can also sled and tube, ice skate, and plan carriage and sleigh rides. As an added perk, kids under 12 ski free in Bend, making this a must for family ski vacations.

In the summer, mild temperatures and cool mountain breezes provide the perfect weather for playing outside. See the area while biking, fishing, golfing, hiking, paddleboarding and rock climbing. Deschutes National Forest and Deschutes River offer plenty of places to roam on and off the water. The Cascade Lake Highway weaves 80 miles past 14 alpine lakes, serving as paradise for anglers and water lovers. Central Oregon also features some of the finest fly fishing venues in the world and several of the best golf courses in the Pacific Northwest. Other recreational sites include Newberry National Volcanic Monument, Tumalo Falls and Lava River Cave.

Downtown Bend and the Old Mill District - both situated on the Deschutes River - have boutiques, local dining, trails and art shows. Browse over 50 independently owned retailers selling everything from antiques and clothing to gear and jewelry. Sample favorite dishes at area restaurants, or take a Bend food tour to experience popular hot spots. Besides renowned Deschutes Brewery, the city is home to dozens of craft brewers, distilleries and wine tasting options. The Bend Ale Trail is one of the largest beer trails in the West. To see big names in music and entertainment, check out the lineup at Les Schwab Amphitheater, which hosts outdoor concerts in summer and fall.

Families find several activities tailored to their interests. Spend time at High Desert Museum to learn about art, history and wildlife. Visitors can swim, float the Deschutes River, wakeboard at Bend Whitewater Park, and splash at SHARC Aquatic and Recreation Center in nearby Sunriver.

Sunriver Resort, located only 12 miles south of Bend, features world-class golf, 30-plus miles of paved trails, water recreation activities, horseback riding, spas, restaurants and vacation rentals situated near all the fun. Additionally, Bend has roller skating and ice skating rinks, escape room games, a trampoline park, and fun center with arcade, bumper cars, go karts, and mini golf.

Those who book a Bend vacation rental also have access to many year-round festivals celebrating art, beer, food, local crafts, music and seasonal events. Visitors can participate in marathons, cycling races, sports tournaments, pet parades, holiday festivities and other events that unite the community.

Gear up for endless excitement! Browse Bend vacation rentals and start planning.

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A Mt. Hood vacation places you in the middle of an outdoor oasis full of mountain views, flowing water and natural beauty. Our Mt. Hood vacation rentals give guests the chance to experience Oregon's wilderness and nearby Portland.

Located 90 minutes southeast of Portland, Mt. Hood offers a retreat from busy life. Although much of the area serves as an outdoor escape, visitors also find small villages with rural and modern charm.

Two main attractions draw nature lovers: Mt. Hood and the Columbia River Gorge. Mt. Hood National Forest measures 60 miles of forested mountains, lakes, and streams perfect for summer biking and hiking. Other outdoor activities include canoeing and kayaking on Trillium Lake, hot-air balloon rides, fishing, exploring Willamette Falls and water tubing.

In winter, experience cold-weather fun at Timberline Lodge, Mt. Hood Skibowl and Mt. Hood Meadows. Ski and snowboard miles of slopes, rent snowmobiles, tube down hill, ride sleighs and snowshoe through the mountains. Visitors can even ski at night, as Mt. Hood Skibowl has one of the largest night skiing terrains in the U.S.

In addition to recreation, Mt. Hood Township houses 14 villages separated into urban, valley and mountain locations. This ensures vacationers can plan a trip that best suits their interests. In urban areas, find a lively arts and culture scene with museums and historic streets lined with boutiques. Head to Willamette Valley farms that open up for tours and celebrate backcountry living. In mountain towns, expect to see everyone playing in the fresh air.

Love food and wine? Take a food tour or visit over a dozen vineyards. A few musts are Oswego Hills, Twill Cellars, St. Josef's and AlexEli. To sample a large area, drive to Portland where companies offer tours. Backcountry Wine Tours and A Great Oregon Wine Tour have day-trip options where guests tastes flavors from different stops.

Other top attractions include Swan Island Dahlias, the historic Oregon City Municipal Elevator, World of Speed museum and End of the Oregon Trail Interpretive Center. Wherever your Mt. Hood vacation rental is located, you have easy access to all towns and sites.

While out and about, don't miss shopping local boutiques and farmers markets. Lake Oswego Farmers Market – one of the largest in Mt. Hood – hosts over 80 vendors each week. The Millennium Plaza Park market opens May through October, and features fresh goodies, nursery items, hot foods, live music and kids' activities.

For a diverse shopping experience, browse Clackamas Town Center and Lake View Village in Lake Oswego. Both districts have dozens of stores selling everything from designer fashion and jewelry to outdoor gear and home décor. Even better, there's no sales tax in Oregon.

While vacationing in Mt. Hood, check out events and festivals. The area hosts celebrations year-round that showcase outdoor adventure, nature, music, art and local communities. Popular events such as Wooden Shoe Tulip Festival, lavender festivals, Oregon Cider Week, Oregon Renaissance Faire, Music Fair and Feast, Pickathon Independent Music Festival and dahlia festivals draw thousands every year.

Plan your mountain retreat in Oregon! Search our Mt. Hood vacation rentals.

Our Oregon Coast vacation rentals give visitors access to miles of beaches and exciting things to do. The Oregon Coast provides a scenic playground to enjoy outdoor recreation, lighthouses, museums and thriving beachside communities.

Forming Oregon's western border along the Pacific Ocean – with the Oregon Coast Range to the east – the area consists of over 30 cities, 235 miles of coastline and 50-plus beaches. Each beach features its own characteristics, such as geological formations, hiking trails, lighthouses, sea lion caves and views for miles. Popular spots include Cannon Beach, home to Haystack Rock; Nye Beach in Newport; Rockaway Beach Wayside; and Manzanita Beach, to name a few.

Many beaches are also found within 60 natural areas. Explore Cape Perpetua, Shore Acres and Ecola State Park. Book fishing charters and tours, hike hundreds of trails, canoe and kayak, surf, and look for whales and dolphins. While reconnecting with nature, see bridges, historical sites and 11 lighthouses on the Oregon Coast. Many are open for tours and accessible via trails where visitors take pictures and learn about regional history.

Want to spend a day on the greens? Our Oregon Coast vacation rentals are located near 30-plus golf courses surrounded by ocean and mountain views. One of the top cities for golf is Bandon, which has four courses including Bandon Dunes Golf Resort. Other notable courses are Ocean Dunes Golf Links and Sandpines Golf Course in Florence and Salmon Run in Brookings.

Experience the Oregon Coast's culture at dozens of art galleries and museums. The area was first discovered in the early 1800s, and has since grown into an attractive destination while preserving its heritage. Visit the Columbia River Maritime Museum and Hatfield Marine Science Center. Then tour the historic Flavel House, Camp 18, Tillamook Air Museum, and Whale, Sea Life and Shark Museum.

Your Oregon Coast vacation rental provides easy access to bustling shopping districts. Find boutiques, outlets, neighborhood markets and antique malls. Additionally, see iconic businesses specializing in local food, handmade items, fashion and gifts. The area also houses nearly 100 galleries and shops where guests browse local art, meet artists and purchase original pieces.

With a location less than two hours from Willamette Valley – Oregon's wine country – cities along the Oregon Coast also offer breweries, distilleries and hang outs that bring everyone together. Highlights include Arch Rock Brewing Company in Gold Beach, Pelican Pub and Brewery in Pacific City, and Fort George Brewery in Astoria. After the sun sets, bars and clubs open for live music, laughs and time with loved ones. Those who want to test their luck can play at Chinook Winds and Spirit Mountain casinos.

Want to enhance the local experience? Sample fresh foods and international cuisine while dining. From cozy cafes and food trucks to European-infused and waterfront gems, the coast's restaurants can't be missed. Most are locally owned, meaning visitors get a true taste of fresh ingredients. Don't leave without trying the seafood.

Discover natural beauty and book your Oregon Coast vacation rental.

Our Portland vacation rentals give you the chance to visit one of the best cities in the U.S., according to Travel + Leisure! iTrip Vacations manages vacation rentals in Portland, including the suburbs of Beaverton, Dundee, Lake Oswego, Newberg, Tigard and Tualatin.

As Oregon's largest city, Portland welcomes visitors to experience exciting attractions and off-the-beaten-path escapes. Portland sits on the Columbia and Willamette rivers with Mount Hood serving as a scenic backdrop, and the Pacific Ocean is less than two hours away. Its location provides opportunities for outdoor recreation, which vacationers can try on their own or with a group.

Start with a trip to the area's natural attractions. The city houses dozens of parks where visitors bike, hike, walk, play disc golf and relax. In addition, expansive gardens beckon nature lovers, with top sites such as International Rose Test Garden, Portland Japanese Garden, Lan Su Garden and Washington Park.

Families and animal lovers can't miss the Oregon Zoo, which cares for over 1,800 animals and offers special exhibits. Kids also enjoy hands-on exhibits at the Oregon Museum of Science and Industry and The Children's Museum. Other sites of interest include: Portland Art Museum, Pittock Mansion, St. Johns Bridge, The Grotto and Pinoeer Courthouse Square.

Additionally, sports fans find action-packed events as the city hosts the NBA Portland Trailblazers, soccer's Portland Timbers and Thorns, as well as a roller derby, summer college baseball, WHL hockey, and racing at the Portland International Speedway.

The great outdoors aren't the only reason to vacation in Portland. The city also has a thriving arts culture that ranks among the best in the U.S. Its vibrant music scene showcases a diverse collection of bluegrass, classic, indie rock, jazz, punk and more. Catch a show at a local venue, or attend the area's festivals that celebrate good tunes and vibes. Don't miss the Portland Jazz Festival, Soul'd Out Music Fest and Waterfront Blues Festival, to name a few.

Foodies also can't help but flock to Portland, which features award-winning dining and quirky dives. From local restaurants and coffee shops to a raved-about wine industry, Portland offers rich flavors. Sample handmade favorites at 600-plus food trucks, enjoy freshness at farm-to-table restaurants or dine at one of the city's hot spots. With over 4,000 restaurants, vacationers never go hungry in Portland.

Drive south to Willamette Valley for wine tours and locally made selections from area growers. Visitors enjoy quick proximity to four wineries in nearby Washington County, all offering different varieties, tours and tastings. Most wineries are located less than 45 minutes from the city and provide a scenic retreat.

Want to take a piece of Portland home? Browse shopping districts full of boutiques, international retailers, art galleries and outlet stores. Downtown Portland - the city's retail core - offers both big-box and small shops selling everything from the latest fashions to souvenirs. One top spot in downtown Portland is Pearl District, home to shops, galleries, restaurants and services, all situated among family-friendly parks. As an added bonus, there's no sales tax in Portland.

We look forward to seeing you! Book your Portland vacation rental.

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Plan an Oregon wine country vacation to experience backcountry beauty paired with modern amenities! iTrip Vacations Portland manages rentals in Willamette Valley, home to two-thirds of the state's wineries and vineyards.

Located south of Portland, Willamette Valley welcomes wine lovers and foodies. Although it's a top place for pinot noir, the region's 300-plus wineries and vineyards offer different tours, tastings, and varieties. Explore via car, bike, horse, hot-air balloon and group excursions.

Many tours are separated into regions, as the area measures 150 miles. Those in Portland can book wine tours that stop at a few places, or plan to spend time at a few while on vacation in Willamette Valley. Top options include Wildwood Adventures, A Great Oregon Wine Tour and Backcountry Wine Tours. To explore on your own, stop by Willamette Valley Vineyards, Eyrie Vineyards and Domaine Serene Winery. Many of these attractions are located only a 45-minute drive to Portland, so guests have easy access.

Don't forget to pair a glass of wine with the perfect cuisine. The region has thousands of restaurants, and many use locally sourced ingredients. Chefs work to create jaw-dropping menus that feature both American and international flavors made with fresh fruits, meats, and veggies. From fun-loving cafes to fine dining, the valley is sure to please the whole group. In addition, find places for steak, pizza, French, Italian, Hawaiian and seafood.

Our guests can also plan outdoor adventures. Silver Falls State Park – the largest state park in Oregon – features over 9,000 acres suited for hiking, mountain biking and horseback riding. While visiting, don't miss the 177-foot South Falls, a must for outdoor enthusiasts. Other popular places for adventure include Champoeg State Heritage Park and Roger's Landing in Newburg; Washington Park in Portland; and Wings and Waves Waterpark in McMinnville.

Willamette Valley offers a rich arts and culture scene packed full of galleries, museums, theaters nightlife hot spots. Browse over 50 art galleries to see pieces made by local artists. Take the family to the Historical Carousel and Museum in Albany and Evergreen Aviation and Space Museum in McMinnville.

Oregon wine country also welcomes visitors to celebrate the region at events and festivals. May is Oregon Wine Month when guests find local events featuring food, wine, music and family-friendly events. Other musts showcase hot-air balloons, gardens, art, culture and dance. Attend the International Pinot Festival, Willamette Valley Music Festival, Wooden Show Tulip Festival, Oregon State Fair, fall festivals and Wine Country Thanksgiving.

Those who vacation in Willamette Valley also have easy proximity to Portland, one of Oregon's most thriving urban destinations. The city offers its own outdoor activities, food scene, world-renown music and entertainment, and historical sites. Plan a day trip and see flourishing gardens, professional sports, concerts and family-friendly attractions.

Search and book one of our Willamette Valley vacation rentals today!

Looking for new management? Read about our full-service Willamette Valley vacation rental management program.