You might have heard people referring to the Bend as the ‘High Desert Oasis’ because of its high elevation and dry ecosystem. This former logging town is nestled between the Cascade Mountain Range and the Three Sisters mountains, making it the perfect gateway for outdoor adventures, such as mountain biking, camping, rock climbing, skiing, and hiking.

This mountainous region, known to many as the Oregon Badlands Wilderness, also houses the Deschutes River that runs through the middle of Bend. This makes Bend the ideal spot for kayaking, fishing, and white-water rafting.

Bend was originally founded as a mill town but has since merged into a center for craft breweries, making it an attractive location for young holidaymakers. Because of the huge array of things to do here, more and more people are flocking to Bend, and to meet the demands, more vacation rentals are ever springing up on the market.

Log cabins, townhouses, condos mansions, and apartment blocks are dotted all over the city. As well as this, each area offers something very unique and different – from the historic neighborhood to the central shopping district, finding a vacation rental in Bend is no easy task.

That is why we have taken the hard work away from you. In this guide, you will find the top vacation rentals in Bend, so you can be sure to find the perfect place to stay for your vacation.

 

Quick Answer: These are the Top 5 Vacation Rentals in Bend

Overall Best Value Vacation Rentals in Bend
1-Bed Georgia Peach Bend
Overall Best Value Vacation Rentals in Bend

1-Bed Georgia Peach

  • > $$$
  • > 8 Guests
  • > Warm and soft furnishings with tons of natural light
  • > Located in Old Bend, 0.6 mi from Drake Park
Best Budget Vacation Rentals in Bend
Cozy 1 Bed Condo with River Views
Best Budget Vacation Rentals in Bend

1-Bed Condo W/ River Views

  • > $
  • > 5 Guests
  • > Fully equipped kitchen and balcony
  • > Located north of the city center on the river
Best Vacation Rentals for Couples in Bend
Cozy and Spacious 1 Bed Condo
Best Vacation Rentals for Couples in Bend

Cozy 1-Bed Condo

  • > $
  • > 4 Guests
  • > River views and access to heated pools and Jacuzzi
  • > Near to the Widgi Creek Golf Club
Best Vacation Rentals for Families in Bend
Quaint 2 Bed Family Home with Yard
Best Vacation Rentals for Families in Bend

2-Bed Home W/ Yard

  • > $$
  • > 6 Guests
  • > TV room den, private office space, and large yard
  • > Located in the historic district, near Downtown, Old Mill District, and Crux neighborhoods
Over-the-Top Luxury Vacation Rentals in Bend
6-Bed Forest Manor Bend
Over-the-Top Luxury Vacation Rentals in Bend

6-Bed Forest Manor

  • > $$$$
  • > 14 Guests
  • > A large, wooden cabin style home in a forest
  • > Secluded location, South of Bend

Looking for other types of accommodation? Check out our guide to Where to Stay in Bend!

Types of Accommodation in Bend

Bend Oregon cityscape

Riverside Apartments and Condos

The Deschutes River is lined with low-rise apartment buildings. These apartments range from single-room studios to three-bed condos and are usually chosen for their conveniently walkable location and river views. Whether facing the river or the surrounding mountains, the views of Bend are best enjoyed from a few stories up!

With some properties boasting added security and communal amenities, this type of rental is ideal for group visits, small families, and can even be affordable for digital nomads. Shared amenities often include swimming pools and Jacuzzis, which are ideal for both summer and winter months. Some modern apartment blocks also have lifts, making them suitable for wheelchair users and baby strollers.

Mountain Cabins

When it comes to this part of the world, the lines between cabin and mansion get blurred. Technically speaking, a cabin is defined as a relatively small, single-storey, yet cozy home built from timber and logs. However, the broader term (in this context) includes large timber homes, including mansions with multiple stories.

Located high in mountainous regions and surrounded by trees and woodlands, this type of vacation rental is very popular on the outskirts of Bend and is the ideal spot for all outdoor enthusiasts and those looking for total seclusion. Also found around the base of the famous Mount Bachelor ski resort, you’ll find cabins ranging in size from quaint lofts for couples, to massive homes with enough room to fit an extended family.

Farewell Bend Park

Townhouses

While Downtown Bend is pretty small, the surrounding residential neighborhoods make up a great deal of the city. These neighborhoods are lined with townhouses suitable for small families and budget travelers. 

If you don’t have a car, we recommend picking a well-located townhouse in Downtown or River West, where it is within walking distance to some of Bend’s top eateries, bars, and grocery shops. These quaint homes offer more indoor space (and often a garden useful during summer) when compared with apartments and condos. They are a great choice for longer visits where you can really settle in.

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Top 20 Vacation Rentals in Bend

From mountain cabins with bubbling Jacuzzis to quaint townhouses surrounded by trees, finding the best vacation rental in Bend shouldn’t be too difficult – especially as we have found all of the best ones for you.

And here they are:

Best Overall Vacation Rental in Bend | 1-Bed Georgia Peach

1-Bed Georgia Peach Bend
  • $$$
  • Warm and soft furnishings with tons of natural light
  • 8 Guests
  • Located in Old Bend, 0.6 mi from Drake Park

Ever walked into a house and felt like you were right at home? This luxurious home away from home has that effect. The pastel-colored rooms have a spacious open-plan layout that connects to one another, making this one-bedroom home feel like it has tons of space.

In fact, though there is one bedroom, this stunning vacation rental in Bend can host up to eight guests, and has all the amenities you would need for a self-catering group vacation.

Located in Old Town Bend, this gorgeous cabin-style house is close to all the main attractions and is just two miles from Hollinshead Park and Ponderosa Park, making this the ideal spot to base yourself if you’re up for some winter skiing.

Best Budget Vacation Rental in Bend | 1-Bed Condo W/ River Views

Cozy 1 Bed Condo with River Views
  • $
  • Fully equipped kitchen and balcony
  • 5 Guests
  • Located north of the city center on the river

A central location, beautiful river views, and a fully-equipped kitchen. What more could you ask for from a budget holiday home in Bend? This spot has everything you need and more for a quick weekend away or to settle in for a while. 

With a private bedroom (with office space) as well as a full-sized, queen pull-out bed and a sleeper couch in the lounge, the space can easily fit five guests even though it is advertised as a one-bedroom condo.

Best of all, this clean and bright space has a balcony overlooking the wild Deschutes River.

Budget Tip: Dorms in Bend start from $10USD per bed. They’re the cheapest accommodation in the city. Search for hostels in the area!

Most Beautiful Vacation Rental in Bend | 2-Bed Old Mill House

Beautiful 2 Bed Old Downtown Mill House
  • $$$
  • Large industrial windows and natural light
  • 6 Guests
  • Located in Central Bend, between Downtown and Southern Crossing

Located in a historic old mill in Downtown Bend, this luxurious home has many stories to tell. While the outside still boasts its original red-brick walls and industrial finishes, the interior has been remodeled with clean white walls, warm wooden furniture, and funky modern art.

The high ceilings and large balcony make it easy to recognize the duplex as an old building filled with history. With massive industrial windows spanning both floors of the shared living area, this self-catering vacation rental in Bend is overflowing with natural light.

Comprised of two good-sized bedrooms and two bathrooms, up to four guests can comfortably sprawl out in this unique place to stay.

Most Luxurious Vacation Rental in Bend | 6-Bed Forest Manor

6-Bed Forest Manor Bend
  • $$$$
  • A large, wooden cabin style home in a forest
  • 14 Guests
  • Secluded location, South of Bend

Experience total luxury in this huge cabin-style retreat in the outskirts of Bend. The central living space is filled with natural light and warm furnishings, exposed wooden beams, and an open fireplace, making it the coziest spot to spend some time with your family. 

Other than the huge outdoor patio with a Jacuzzi, BBQ, and cosy seating overlooking the secluded forest outside, this house also includes six bedrooms, five bathrooms and a games room. While you’ll likely be spending most of your time adventuring outdoors, you’ll be glad to return home to this spot after a day in the mountains.

Because this vacation rental is 16 miles out of Drakes Park, bicycle rentals are available at the property.

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Best Vacation Rental in Bend for Families | 2-Bed Home W/ Yard

Quaint 2 Bed Family Home with Yard
  • $$
  • TV room den, private office space, and large yard
  • 6 Guests
  • Located in the historic district, near Downtown, Old Mill District, and Crux neighborhoods

This quaint townhouse is a great budget option for small families traveling to Bend. Located right in the heart of the historic district, you’ll easily be able to walk to major attractions as well as top restaurants and bars from the house. 

Ideal for families, this spot has a huge yard with an outdoor living area and BBQ, as well as a basement den with a TV – the perfect spot to occupy the kids.

There is even a pair of bicycles that you can use to cycle around the city!

Best Vacation Rental in Bend for a Weekend | 1-Bed Townhouse

Charming 1 Bed Townhouse with Patio
  • $
  • Homey interiors, a fireplace, and a small yard
  • 2 Guests
  • Across the river from Old Mill District and Downtown Bend

If you’re popping past Bend for a quick weekend visit, you’re best off choosing a property that is in the center of town so you can easily check out the main attractions.

This quaint townhouse is just around the corner from some of Bend’s top restaurants, boutique shops, and mountain biking and hiking trails. From the doorstep of your rental, you’ll be able to walk to just about anywhere you’ll need to during a weekend visit such as the Deschutes History Museum.

The home itself is spacious and bright and simply decorated with homey furniture. It comes with a free parking spot for those on an Oregon road trip, a fully-equipped kitchen, and a warm fireplace, making it one of the best vacation rentals in Bend for quick visits.

Best Vacation Rental in Bend with a Jacuzzi | 4-Bed Home W/ Golf

4-Bed Home W Golf Bend
  • $$$
  • Located on Bend Country Club Golf Course
  • 12 Guests
  • Located 3.1 miles from Ponderosa Park

This unique and luxuriously styled vacation rental in Bend is the perfect spot to settle into and enjoy a relaxing game of golf. It’s equipped with everything you might need while on vacation such as a fully-equipped kitchen, four homely bedrooms, and a huge outdoor area.

Located just three miles out of Ponderosa Park, perfect for those wishing to experience some fantastic skiing and cycling nearby.

Choose to sit by the garden fire pit, or take a dip in the raised Jacuzzi which overlooks the sprawling green pastures. Or better yet, challenge your 11 other guests at a game of table tennis or pool. You sure won’t be bored staying at this home!

Accessible Vacation Rental in Bend | Studio W/ River Views

Trendy Studio with River Views
  • $
  • Large windows and a balcony with river views
  • 2 Guests
  • Just north of the city center, close to parks and restaurants

This charming modern condo has been kitted out with trendy furniture imported from Norway. Ideal for guests with accessibility limitations, the apartment block has lift access and wide, open spaces.

Enjoy the river views from your private balcony, or venture outside and take a stroll upriver on one of the many paved footpaths – perfect for wheelchair users and strollers.

The studio home has a state-of-the-art gourmet standard kitchen and a cozy fireplace. Warm grey walls, white wooden cabinetry, and glass and wooden furniture give the apartment a modern feel.

Most Central Vacation Rental in Bend | 1-Bed Modern Condo

Brand New 1 Bed Modern Condo
  • $$
  • Open-plan condo with private entrance and a balcony
  • 2 Guests
  • In central Bend, near Newport Avenue shops and restaurants

This spot couldn’t be better located. You can stroll down the street to the major shopping district, well-known restaurants, such as the highly rated Spork.

While it’s part of a private residence, the one-bedroom luxury vacation rental in Bend is completely private from the main house, sharing no walls.

The interior has been renovated with warm wooden floors and marble countertops. The stunning kitchen is a crowd favorite. It is fitted with top-of-the-range appliances, including a gas-hob center island.

Best Vacation Rental for a Large Family in Bend | 5-Bed Mansion

Luxurious 5 Bed Mountain Mansion
  • $$$$
  • Five king bedrooms. Includes a patio with Jacuzzi and fire pit
  • 12 Guests
  • Located in a prestigious neighborhood in the mountains surrounding Bend

If you’re searching for opulence in the mountains, this huge home will provide you with the goods. Located high in the hills in a private gated resort, this contemporary modern building has five king-sized bedrooms, each with its own ensuite bathroom.

There is also a huge kitchen stocked with everything you might need and an open-plan living space where up to 12 guests can gather and enjoy good quality time together.

A few steps from the house you’ll be able to enjoy a range of some of the best hiking trails in Oregon, all from your doorstep. Best of all, returning home is a pleasure, and you’ll be able to unwind in the warm Jacuzzi.

Best Vacation Rental in Bend for Friends | 4-Bed Oasis W/ Jacuzzi

4 Bed Contemporary Oasis with Jacuzzi
  • $$$
  • Classy furniture with top-quality amenities
  • 10 Guests
  • Near all the best biking and hiking mountain trails

Gathering for a vacation with your best friends has never been such a breeze. This spacious home has four private bedrooms, all very separate from one another. Perfect for those who love to socialize, but also enjoy their own space.

The central living area is the ideal spot to spend an evening with friends. I can imagine cooking a family-style meal together in the gourmet kitchen (which is fitted with every appliance you might need) and enjoying the meal around the outdoor fire pit.

It is also ideally located near to some of the areas best hiking trails, so if you’re outdoor lovers, you’ll love this cozy retreat.

Most Unique Vacation Rental in Bend | 2-Bed Dome Home

Cozy and Secluded 2 Bed Dome Home
  • $$
  • Open plan concept studio living and mountain views
  • 4 Guests
  • Located on private property near the ski-slopes

Hidden away in the mountains, you’ll find a spherical-shaped dome house on the rental market. This unique geometric dome home has been decorated with inviting interiors.

The double-story loft space includes an upstairs lounge with a smart TV and a gas fireplace – the perfect spot to unwind and warm up after a day out in nature.

A personal favorite, the main bedroom has rooftop windows, which make this the best vacation rental in Bend to do some bedtime stargazing.

Best Vacation Rental in Bend for Honeymooners | Cozy 1-Bed Condo

Cozy and Spacious 1 Bed Condo
  • $
  • River views and access to heated pools and Jacuzzi
  • 4 Guests
  • Near to the Widgi Creek Golf Club

This one-bedroom condo exceeds all expectations when it comes to interior design. It has been impeccably thought out, with a blend between modern and traditional fittings, comfortable furniture, and top-quality appliances.

Although not useful for honeymooners, the living room does have a fully hidden fold-out bed that can be used for larger parties.

Gusts can relax on the private balcony or make use of the shared pools, Jacuzzi, and lush communal gardens. Bend is your oyster from this well-located gem.

Best Vacation Rental in Bend for Nightlife | 4-Bed Cabin W/ Games

Spacious 4 Bed Cabin with Games
  • $$$
  • Cozy modern cabin interiors
  • 8 Guests
  • In a residential neighborhood in River West

This stunning cabin offers the best of both worlds for those who enjoy spending the day out in nature and evenings socializing at a bar. The home is just down the street from some of Bend’s best bars and breweries, of which the city is so well known.

The home itself is beautifully decorated and filled with both traditional and contemporary interiors. Picture wooden floors and exposed ceilings combined with modern couches and lighting fixtures. Somehow, it all works, and this spot makes for a great home away from home in Bend.

Best Vacation Rental in Bend with a View | 1 Bed Riverfront Condo

New 1 Bed Riverfront Condo with Balcony
  • $
  • Comes with fireplace and access to a shared pool and Jacuzzi
  • 2 Guests
  • In a residential area in River West, right on the river’s edge

This basic condo boasts some of the most beautiful river and mountain views in Bend, for a fraction of the price you might expect to pay for a mountain cabin.

Skip the cost and settle into this basic, yet fully-equipped one-bedroom home with a balcony overlooking the Deschutes River. There is also a large kitchen that sprawls out into the living area, making this small home feel like it has more spacious.

You’ll also have full access to shared amenities including an indoor Jacuzzi and swimming pool and free private parking.

Pet-Friendly Vacation Rental in Bend | Studio with Yard

Beautiful Studio with Enclosed Yard
  • $
  • A full kitchen and comfortable open plan living space
  • 3 Guests
  • Located in River West, a mile from the Old Mill District

This gorgeous small loft space is the perfect self-catering vacation rental in Bend for couples. Even better, the space is pet-friendly and so your furry friends can join you. You’ll find dog beds, food bowls, and treats in this home – it’s a dog’s heaven!

Located above the garage of a private residential home, this single room studio has a comfortable lounge area, a fully-equipped kitchen with high-quality appliances and tons of preparation space, and even a small private office nook.

There is also an enclosed yard so your animals can enjoy some outside space safely.

Best Cabin Vacation Rental in Bend | 3-Bed Mountain Cabin

Traditional Alpine 3 Bed Mountain Cabin
  • $$
  • Traditional log cabin with wood burning fireplace, fishing dock, and gas BBQ
  • 8 Guests
  • Located on the river in Three Rivers

When you think of a traditional cabin, this home comes to mind. High-vaulted ceilings, tons of huge glass windows, and low-hanging lighting, all surrounded by wooden walls, ceilings, floors, and furniture.

The staircases and beams are even made using rough cuts of timber logs making this home even more authentic!

A cozy fireplace and lounge, a well-stocked kitchen, and a laundry room with washer/dryer facilities are all you need for a simple Oregon vacation. Even better, this cabin is located on the river and has a stunning outdoor deck with a grill, and even a fishing dock jutting out into the river.

Best Ski/Snowboard Friendly Vacation Rental in Bend | 2-Bed Condo

Contemporary 2 Bed Ski Condo
  • $
  • Access to a pool and Jacuzzi
  • 6 Guests
  • Located at the base of Mount Bachelor, 10 minutes from Downtown Bend

Located just at the base of one of Oregon’s most revered ski mountains, this homey cabin is without a doubt one of the best vacation rentals in Bend for skiers and snowboarders. Cook up a storm in the beautifully equipped kitchen and relax on the comfortable sofas by the fireplace. 

With so many windows, this home is flooded with natural light and warmth. From the private balcony, you’ll see forest trees as far as the eye can see.

During the summer months, take a dip in the shared swimming pool and Jacuzzi, a few steps from your front entrance. 

Best Vacation Rental in Bend for Stargazing | 2-Bed Log Cabin

Remote 2 Bed Log Cabin with Jacuzzi
  • $$
  • Traditional log cabin interiors and a Jacuzzi
  • 6 Guests
  • In a remote mountain setting in Three Rivers.

Out in Bend, you’ll be able to see some of the most beautiful starry nights you’ve ever laid eyes on. This remote cabin lies in a secluded forest setting with few lights around it offering incredible stargazing views, which in our opinion makes it one of the best cabins in Oregon.

The traditional log cabin is one of the top luxury vacation rentals in Bend for a few reasons. It blends rustic mountain life with luxury, by including soft robes, top-quality towels and linens, memory foam mattresses, and even an Amazon Alexa to sort you out with music or travel advice.

The hosts also welcome dogs and even include dog bowls and beds for your stay. It is recommended that those visiting this property rent a car as its location is remote and secluded.

Best Historic Vacation Rental in Bend | Basic Old Mill Studio

Basic Self Catering Old Mill Studio
  • $$$
  • Modern interiors contrasted with an old urban red-brick exterior
  • 3 Guests
  • Between Downtown Bend and the Old Mill District

This authentic red-brick condo used to be an old mill building. Today, it has been repurposed as residential accommodation and is separated into condos.

This small and simple studio space has a shared living and dining room, kitchen, and bedroom, all under the same industrial-style corrugated ceiling. Expect quirky furniture, interesting modern art, and leafy houseplants to brighten up your stay.

While this spot has a kitchenette, it doesn’t have a full kitchen. However, being so close to central Bend, you won’t have to worry about finding a great spot to eat!

Final Thoughts

Whether you’re paddling down the crystal clear Deschutes River in Summer or dicing between trees on the Mount Bachelor Ski Resort during Winter, Bend truly is small in size but big on adventure!

Surrounded by nature, this beautiful small city receives more sunshine than Oregon’s other main cities and it is no surprising why it’s becoming such a hugely popular destination for vacations.

As long as you’re a fan of the outdoors, you’re sure to find some of the best vacation rentals in Bend. Do you have a favourite from this list? Let us know in the comments.

And don’t forget to take out Travel Insurance for your trip! I have been using World Nomads for some time now and made a few claims over the years. They’re easy to use, professional and relatively affordable. They may also let you buy or extend a policy once you’ve started your trip and are already abroad which is super handy.

If there’s one insurance company I trust, it’s World Nomads. To find out why I use World Nomads, check out my World Nomads Insurance review.

Getting an estimate from World Nomads is simple—just click the button or image below, fill out the necessary info, and you’re on your way!

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