10 Best Monthly Rentals In Bend, Oregon - Updated 2024

Aparajita
Aparajita 
Contributing Writer
Updated
| 5 min read

Located near Deschutes River, Bend is a small city in Oregon. Home to beautiful lakes and surrounded by the peaks of Cascade Mountains, Bend is a place where tourists can not only reconnect with nature but also try out activities like hiking and skiing; things that may not have time to engage in during their busy day-to-day lives. Sightseeing is also a good option here as Bend has its own extinct volcano, Pilot Butte and a lava tube called Lava River Cave. If you’re a lover of craft brews, Bend is the best place to visit as it is home to some of the best breweries in the country. So, pack your bags and check out this list of the best monthly rentals in Bend, Oregon.

We handpicked these listings carefully, considering (wherever possible) host status, recent guest reviews, location, accommodation type, prices, decor, availability of dates, and long-term stay rules and regulations. The image galleries get refreshed with the latest updates regularly. They were last updated on May 25, 2024.

1. Sunshine Cottage (from USD 179)

Once a historic home, this property was renovated to not just catch up with modern times but also equip the house with all the amenities required for guests to have a comfortable stay. Surrounded by restaurants, shops, parks and breweries, the house is perfect for those travelling with family. It has two bedrooms, both equipped with a queen-size bed and if needed, a floor mattress can be provided.

There is also a sofa bed in the common area and if you are travelling with a baby, the house has a cot as well. The kitchen is equipped with everything required to make a decent meal, and the hosts have also provided an electric barbecue grill. Whatever you might need to spend your day in comfort, this house has it all.

Stayed at this property?
Bend, Oregon, United States
706 meters (0.5 ft) from Drake Park
214 reviews   Superhost Wifi Available
Entire bungalow 3 Beds 6 Guests 2 Bedrooms 2 Bathrooms

Accommodates: 6

2. Modern apartment with a fireplace (from USD 112)

Situated close to the popular downtown area, this recently constructed apartment is perfect for those who love to be out and about. With various famous spots like Old Mill district and Mt Bachelor nearby, while staying here sightseeing is convenient and easy.

Having an open layout, the apartment has one bedroom along with a sofa bed in the common area, as well as a bunk bed for children to use. It also has a fireplace to keep you warm during the chilly nights. There’s a well-equipped kitchen, should you wish to cook your own meals. With shops and restaurants nearby, this apartment is ready to make your trip to Bend worthwhile.

Stayed at this property?
Bend, Oregon, United States
900 meters (0.6 ft) from Drake Park
269 reviews   Superhost Wifi Available
ENTIRE RENTAL UNIT 2 Beds 4 Guests 1 Bedroom 1 Bathroom

Accommodates: 4

3. Shasta Loft

Located in the historic Old Bend, this loft has one bedroom and one bathroom, perfect for those who love to travel by themselves or couples looking for a romantic getaway. With an open plan, the loft has vaulted ceilings, as well as a skylight to ensure that it always has a flow of natural light.

Apart from the bedroom, an extra bed can be found in the living room, allowing up to four people to stay in the loft. Offering a fully functioning kitchen as well as a sauna, this loft is a deal you don’t want to miss out on.

Stayed at this property?
Bend, Oregon, United States
612 meters (0.4 ft) from Drake Park
188 reviews   Superhost Wifi Available
Entire loft 2 Beds 4 Guests 1 Bedroom 1 Bathroom

Accommodates: 4

4. Cosy apartment in Lower West Hills (from USD 139)

Located in Lower West Hills, this apartment was recently constructed and thus has all the amenities needed to ensure you have a comfortable stay. The apartment has one bedroom, which is furnished with a queen-size bed and a sofa bed in the living room.

There is also a sun deck, which is equipped with a grill and propane fire pit that you can enjoy on cold nights. For those who like to sleep in, the bedroom has blackout curtains, ensuring that the sun can’t get between you and your dreams.

Stayed at this property?
Bend, Oregon, United States
1.09 km (0.7 mi) from Drake Park
187 reviews   Superhost Wifi Available
Entire guesthouse 1 Bed 3 Guests 1 Bedroom 1 Bathroom

Accommodates: 3

5. Guest house located near Deschutes River (from USD 139)

Located near Deschutes River, this small and cosy guest house is perfect for those who are in need of reconnecting with nature. With the hiking trail nearby, you can immerse yourself in natural beauty as you hike up the path.

Since the guest house is close to the Old Mill, several shops and restaurants are just a short walk away. While the guest house only has one bedroom, it is equipped with everything you might need during your stay such as a full kitchen, high ceilings, a fire pit, and a private patio.

Stayed at this property?
Bend, Oregon, United States
2.49 km (1.6 mi) from Drake Park
321 reviews   Superhost Wifi Available
Entire guesthouse 2 Beds 4 Guests 1 Bedroom 1 Bathroom

Accommodates: 4

6. Fall Creek Suite (from USD 121)

With a central location, this comfortable house is just a short walk away from some of the best restaurants in Bend, as well as a variety of shops and tourist spots like Mt Bachelor, Cascade Lakes, and others.

The house itself has two bedrooms with a king-size bed each, and a functioning kitchen, a private patio on the outside along with barbecue tools, and a hammock. Whether you’re in Bend for sightseeing or to just relax while taking in the surrounding view, this house is perfect for you.

Stayed at this property?
Bend, Oregon, United States
903 meters (0.6 ft) from Drake Park
351 reviews   Superhost Wifi Available
ENTIRE HOME 2 Beds 4 Guests 2 Bedrooms 1 Bathroom

Accommodates: 4

7. Comfy house for adventurers (from USD 148)

Located near Mt. Bachelor, this house is perfect for those who love adventure as various hiking trails, cycling lanes, and places for other activities like kayaking, paddle boarding, and more can be found near this house.

It has one bedroom furnished with a queen-size bed, a sofa bed in the common area, and a kitchen equipped with everything needed to cook. There is also a laundry room, as well as a porch outside and a picnic table. A double swing can be found, along with barbecue tools.

Stayed at this property?
Bend, Oregon, United States
2.13 km (1.4 mi) from Drake Park
124 reviews   Superhost Wifi Available
ENTIRE HOME 2 Beds 4 Guests 1 Bedroom 1 Bathroom

Accommodates: 4

8. The Dylan House (from USD 104)

Nestled in a recently built townhome, this guest suite was furnished to have a rustic feel to it while providing guests with all the amenities they need for a comfortable stay. Apart from the spacious bedroom with a queen-size bed, the suite has a full kitchen and a comfortable sofa bed in the common area, big enough to accommodate children. There is also a fireplace to keep you warm during the cold nights. Laundry facilities are also on offer.

Stayed at this property?
Bend, Oregon, United States
3.81 km (2.4 mi) from Drake Park
250 reviews   Superhost Wifi Available
Entire guest suite 2 Beds 2 Guests 1 Bedroom 1 Bathroom

Accommodates: 2

9. Comfortable bungalow with a unique look

Located near downtown Bend, this modern bungalow was designed with a unique view in mind, giving it an urban-chic look. However, that is no reason to worry as it is equipped with not just a fully functioning kitchen but has laundry facilities, a private garden, a barbecue grill, and a hot tub as well.

The bungalow has three bedrooms, one with a king-size bed, one with a queen-size bed, and one with two single beds. Restaurants, pubs, and other places of interest are just a short walk away.

Stayed at this property?

1.15 km (0.8 mi) from Drake Park
62 reviews   Wifi Available
Entire bungalow 3 Beds 5 Guests 3 Bedrooms 1 Bathroom

Accommodates: 5

10. Modern bungalow with an old-world charm

Remodelled in 1942, this beautiful bungalow once used to be a mill house. Now, it has two spacious rooms, both are equipped with a queen-size bed. Due to its convenient location, almost all the places worth seeing in Bend are at a close distance, making sightseeing easy for tourists. The functioning kitchen is equipped with everything, from cooking utensils to a Jenn-Air refrigerator, to make your stay comfortable.

Nearby, you can find an indoor farmer’s market, as well as a grocery store. Most of all, if you like to travel with your pets, this bungalow is pet-friendly and even have a large front yard to accommodate their walks and exercises. While a deposit is required when bringing your pets, it’s worth it when you can spend a wonderful vacation with them by your side.

Stayed at this property?
Bend, Oregon, United States
1.82 km (1.2 mi) from Drake Park
65 reviews   Wifi Available
Entire bungalow 2 Beds 5 Guests 2 Bedrooms 1 Bathroom

Accommodates: 5

Hike up the natural trails of Bend

While Bend may be a small city in Oregon, that doesn’t mean it doesn’t have its own beauty and charm. Surrounded by mountain peaks and with a river running through, this city holds many beautiful sights. Not to mention its own volcano as well as a lava tube, it has things that not every place can brag about having.

Any must-sees we missed? Tell us about them in the comments section or write a post here to help out fellow travelers!
Disclosure: Trip101 selects the listings in our articles independently. Some of the listings in this article contain affiliate links.

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Aparajita, an aspiring writer, began her writing journey at a young age. She completed her BA in Psychology, English, and Journalism and is currently pursuing her Masters in Creative Writing at...Read more

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