Holiday rentals in Bend

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Top-rated holiday rentals in Bend

Guests agree: these stays are highly rated for location, cleanliness and more.

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Guest favourite

Home in Bend

4.97 out of 5 average rating, 362 reviews

Walk to On Tap, Minutes to Downtown Bend, & Garage

Welcome to your home away from home in Bend. This modern home with private entrance and attached garage is located minutes by car from downtown Bend & Old Mill and a short drive to Mt. Bachelor with premium, luxury amenities offered throughout. The most comfortable memory foam mattresses + cozy lodging await! Six food trucks and ~35 rotating draft beers at a very walk-able 0.6 miles away! Pilot Butte 2 miles Bend City Center 3 miles RDM Airport 16 miles Mt Bachelor 25 miles Smith Rock 25 miles

Guest favourite

Rental unit in Redmond

4.97 out of 5 average rating, 461 reviews

Smith Rock Contemporary

Epic views await at this new contemporary Airbnb suite. Situated atop Cinder Butte, with stunning views of Smith Rock, Mt. Hood, Mt. Jefferson and the Terrebonne valley. Enjoy this 800 sf apartment with dedicated entrance and parking, open concept living, laundry, bedroom and custom bath. Luxe accommodation just minutes from Smith Rock State Park. A huge covered deck with magnificent views will make you feel right at home. Get your trip started off right with a gorgeous sunrise over Smith Rock.

Guest favourite

Home in Bend

4.99 out of 5 average rating, 145 reviews

Westside Sweet Suite - modern 1 bedroom studio...

Enjoy Bend at it's best. Our house is perfectly located on the westside of town, giving you easy access to all of the things that make Bend unique. This suite is within walking distance to the best beer, restaurants and market in town. Enjoy the mountains, rivers, parks and every activity available to you to get the most out of these natural gems. Bend is an outdoor paradise all year round, so get out and play. Come home and relax in this great space, with everything that you could need.

Guest favourite

Guest suite in Bend

4.89 out of 5 average rating, 151 reviews

New Modern and Cozy Private Studio In The Woods

New, clean, modern Additional Dwelling Unit on an 5 acre wooded lot on Bend's North West side. The neighborhood is quiet with 10 acre lots and farms. Close to Trader Joes, Natural Grocer and Cascades Shopping Mall. Only 4 miles to downtown. Full kitchen. The unit is at ground level attached to the back of the main house. Forget your worries in this serene and peaceful place. 1 Mile from Tumalo State Park and Riley Ranch Nature Preserve. Easy access to all the beauty Bend has to offer.

Guest favourite

Tiny home in Bend

4.9 out of 5 average rating, 263 reviews

The Oasis Airstream no pet fee

Reconnect with nature at this unforgettable escape, surrounded by gorgeous desert views. Beautifully designed and fully equipped for your comfort. Pet friendly and located just 15 min from downtown Bend. The Oasis Airstream is on a quiet 10 acres. I live here with my family and have a small farming business. There is an ample yard with outdoor table and chairs, outdoor couch, and fire place. There's also a hammock for swinging in the shade on those long summer evenings.

Guest favourite

Cabin in Bend

4.99 out of 5 average rating, 440 reviews

Skyliners Getaway

Our tiny log cabin is a cozy getaway, close to hiking, mountain biking, and cross country skiing but only 10 miles from the amenities of Bend Oregon. It is a rustic place, with modern touches, like a gas range, refrigerator, and a gas fireplace. The bathroom is detached from the cabin - steps from the door. It is fully equipped. Our place is perfect for people who love the outdoors with the comforts of home. No children under the age of 12 -- And alas, No Pets .

Guest favourite

Rental unit in Old Bend

4.99 out of 5 average rating, 101 reviews

WALK DOWNTOWN & OLD MILL-1 BLOCK TO THE RIVER-#4

Location allows an easy walk to Downtown and Old Mill District. One block to the Deschutes River. Modern one-bedroom fully furnished rental. Fully equipped kitchen, washer/dryer in unit. Ductless heat/air conditioner for your comfort. Smart TV provides streaming and top tier HD cable TV. A private 5' x 9' locked storage area for your kayaks, bikes, clubs, skis, boards. . ... NO smoking and sorry, no pets. City of Bend Short Term Operating License No. STR-15-0016 .

Guest favourite

Guest suite in Bend

4.98 out of 5 average rating, 428 reviews

Kathy's Westside Apartment near Mt. Bachelor

Easy access to Mt. Bachelor, Phils Trails and hiking in the Deschutes National Forest. Downtown Bend and the Old Mill District are both less than 2 miles away. 1.5 miles to the Hayden Home Amphitheater. Discover restaurants, breweries, shopping, art galleries, theaters, and more! With Mt. Bachelor resort, hiking and fishing just minutes up the road, you will relish your stay in the heart of Central Oregon! No room tax for stays of 30 days or more

Guest favourite

Guest suite in Bend

4.92 out of 5 average rating, 112 reviews

Private 1 bed/1 bath with kitchen

Just steps or a quick bike ride to eateries and brews right here in Midtown, and less than a mile from downtown! This attached private apartment with bedroom, living room, bathroom, kitchen, balcony, and beautiful view of my bachelor will be your home away from home where you can relax in peace after a day on the slopes, mtn biking, or a day on the river. Apartment has heater and AC for those hot days and washer and dryer are available.

Guest favourite

Guest house in Bend

4.99 out of 5 average rating, 544 reviews

Cozy Up! Botanical Studio in the Trees

Wake up to treetop views at this spacious bungalow peppered with live plants, unique art, and a stunning cedar ceiling. Stroll down to the Deschutes River Trail, which can take you downtown. Enjoy the locals-favorite First Street Rapids Park, then curl up and restore on the ultra comfy king bed. Creature comforts abound! No pets please. Trip insurance recommended if illness, weather or smoke may be an issue.

Guest favourite

Guest suite in Bend

4.96 out of 5 average rating, 373 reviews

Cozy Apt Near Trails, Mt. Bachelor, Old Mill

Above-garage apartment with private entrance, full kitchen, full bathroom, and loft sleeping quarters with a queen bed. Our space is conveniently located on Century Drive (Cascade Lakes Highway) on the way to Mt. Bachelor, the Cascade Lakes, and 1.5 miles from Phil's Trail system. Our location is just out of town, but provides easy access to the Old Mill, West Side, and downtown.

Guest favourite

Home in Bend

4.99 out of 5 average rating, 134 reviews

Butler Corner - New, Clean & Minutes From Downtown

Relax and enjoy all that Central Oregon has to offer in this nice, clean and newer 2019 built home. Butler Corner is located in Midtown and sits on a corner lot in a nice quiet and charming neighborhood just minutes from Downtown. We invite you to stay a while in this comfortable space and think of it as your home away from home.