10 Vacation Rentals In Bend, Oregon - Updated 2024

vacation rentals in bend oregon
| 6 min read

Being one of the most geographically diverse states in the US, Oregon is visited by many tourists all year round. Oregon’s landscapes and waterways include volcanoes, dense evergreen, mixed forests, deserts, semi-arid shrublands, beaches, and lakes. It also houses the famous Crater Lake National Park, Multnomah Falls, Painted Hills, and Mount Hood flocked by tourists for skiing and snow activities. Indeed, Oregon can offer something new to every traveler’s plate. This diversity extends to the fabulous vacation homes in this place. Go check out the top 10 vacation rentals in Bend, Oregon, USA.

We handpicked these listings carefully, considering (wherever possible) Superhost status, recent guest reviews, location, accommodation type, prices, availability of dates, decor, and amenities. The image galleries get refreshed with the latest updates regularly. They were last updated on May 19, 2024.

1. Family home with treetop views (from USD 120)

Get close to nature and sleep comfortably in a quiet home. You’ll stay on the first floor of this apartment with windows that offer refreshing treetop views. Your spacious bedroom will soothe you after a tiring day with its fresh, fragrance-free and 100% cotton sheets. The whole property is well-kept and clean and is child-friendly. A queen size air mattress can be set up in the living room. Kids would love it! The bathroom has a tub and shower combination with bath essentials provided. Fill our gastronomic cravings by visiting the restaurants within walking distance. The hosts, Mike and Darla, would be happy to give good recommendations for you and your family.

Stayed at this property?
Bend, Oregon, United States
2.37 km (1.5 mi) from Drake Park
1120 reviews   Superhost Wifi Available
ENTIRE RENTAL UNIT 1 Bed 2 Guests 1 Bedroom 1 Bathroom

Accommodates: 2

Top guest reviews
Amenities & Room:
the apartment has a great views of mountain
the bed and sofa were very comfortable as was the temperature
the bed and couch and both very comfortable and everything was sparkling clean
mike and darla’s place was better than expected the space was very cozy with nice touches and amazing amenities
the apartment met all of my needs: warm and plush bed nice fast internet clean and well-lit bathroom
everything was super clean & comfortable
really comfortable clean and lovely stay
very clean comfortable and well-equipped
great place to stay very clean and quiet
the space was very clean and attention to detail was evident
great hosts and accommodations
i appreciate the effort the hosts made to make guests feel as if they were home
very comfortable space and chatted with very nice hosts
they were also very responsive and willing to help beyond being a host to this airbnb
mike and darla are awesome hosts
close to everything fun in bend
close to pretty much everything
great place and location definitely recommend it
great spot and great location
great location and value for west side bend
Read more reviews

2. Quirky house surrounded by a garden (from USD 65)

Book yourself into this whimsical house surrounded by a lovely garden! Everything you need is here, including a private living space with an equipped kitchenette, a loft, a living room, a modern bathroom, a spacious bedroom, and entertainment appliances. The kitchenette is equipped with a toaster, an induction burner, a french press, an oven, utensils, and stocked coffee. You can unwind in the fenced backyard or use the outdoor grill to bond with your loved ones. Guests love soaking in the tub after a long day of hiking. You can easily access downtown from this property. Others also find this place ideal for relaxation and meditation.

Stayed at this property?
Bend, Oregon, United States
869 meters (0.6 ft) from Drake Park
796 reviews   Superhost Wifi Available
ENTIRE RENTAL UNIT 2 Beds 3 Guests 2 Bedrooms 1 Bathroom

Accommodates: 3

Top guest reviews
Amenities & Room:
the claw foot tub is lovely with the skylights lighting up the bathroom
the apartment has so many nice touches and the quirkiness makes it fun and unique
the space was beautifully designed and very comfortable
having access to laundry a grill and hot tub were all added bonuses
this is a very enjoyable apt with a great backyard and sitting area
it was super clean and cozy
everything was clean and well-maintained
the space itself is clean and comfortable
our space was clean and quite
a clean private and modern sweet spot
the hosts were so friendly and quick to reply
alex was super responsive and eager to help
the host was so kind and expectations were very clearly communicated
respectful kind and amazingly helpful host
everyone we met during our stay was welcoming & helpful
great location easy walk to downtown
the location was great and super close to everything
close to downtown- easy walk
it's a super cute and decorative place in walking distance to downtown bend
we loved the ability to walk around downtown
Read more reviews

3. Vibrant and modern home with high ceilings (from USD 249)

You will not only enjoy this home because of its central location but for its elegant architectural design and interiors. Get plenty of sunshine around the house through its large-sized windows. The interiors are a mix of modern and hip, vibrant and subtle designs. There is a fully equipped gourmet kitchen ready to accommodate your cooking sessions and a spacious dining area for the whole family. Location wise, this property won’t disappoint. You can walk a couple of blocks to Chow, a local favorite, or enjoy Japanese cuisine over at Kanpai Sushi. Check out the fun shops, bakeries, coffee shops, pubs, and restaurants at Newport Avenue or stroll through the Westside neighborhood. There are plenty of options for fun whether you’re indoors or outdoors.

Stayed at this property?

849 meters (0.6 ft) from Drake Park
47 reviews   Wifi Available
House 6 Guests 3 Bedrooms 3 Bathrooms

Accommodates: 6
Minimum Nights: 2
Refund Policy : 100% refund if you cancel at least 60 days before check-in.

Top guest reviews
Amenities & Room:
Last I personally like a TV in each bedroom
It had everything we needed to be comfortable
Kitchen was well equipped to cook a meal
others breweries not in town We really enjoyed having the fire pit living room area was comfortable for watching tv together
The kitchen had everything we needed and
clean beautifully furnished and very comfortable
Beds were comfortable and linens and towels were of good quality
The house is new modern and nicely decorated with clean lines
new clean and comfortable--living area and fireplace are great--
were nicely thought out Garage was supplied with bikes and some helmets
We hope to return to this beautiful home
The location is great and the unit is new
I am often disappointed with the cleanliness of rentals but this house was super clean and well stocked
Amenities shampoo and soaps books
comfortable and in a great location Walking distance to amazing restaurants and breweries close to epic mountain biking
coffee shops and restaurants Easy bike ride to downtown and Old Mill
It is a cute little school and better than looking at someone's house
It's a quiet neighborhood
The place is also perfectly located Easy walking distance to a bunch of great spots
Read more reviews
Earn OneKeyCash for every dollar spent on eligible hotels, vacation rentals, flights, car rentals, and more when you book across our family of brands.

4. Two-bedroom bungalow (from USD 338)

Create memories with your loved ones in this family-friendly bungalow located at one of Bend’s prime Westside neighborhoods. It sits just two blocks away from the first Rapids Park on Deschutes River and is at a walking distance to the downtown area. The full home sleeps four and has a separate studio apartment with a living area and a king master suite. All in all, the property sleeps a total of six. To ensure privacy, both living areas - bungalow and studio apartment, cannot be rented out separately. A beautiful flagstone garden courtyard creates just the right amount of privacy and gathering space between the two. A gourmet kitchen is provided, as well as Weber gas grill and outdoor dining for six on a charming garden deck.

Stayed at this property?

749 meters (0.5 ft) from Drake Park
48 reviews   Wifi Available
bungalow 8 Guests 3 Bedrooms 3 Bathrooms

Accommodates: 8
Minimum Nights: 2
Refund Policy : 100% refund if you cancel at least 60 days before check-in.

Top guest reviews
Amenities & Room:
kitchen well stocked with essential cooking items
They use artificial air fresheners which some people have allergies to
The home was cozy yet bright with just the right amount of space Great attention to detail: nice linens comfy bed
The twin beds in the second bedroom are on casters and rolled around the room quite a bit which is fine for kids but might be difficult or dangerous for older adults
We loved the big beds and en suite bathrooms in each the cozy living room (card games late into the night) the hot tub
Rebecca and her staff were easy and pleasant to work with
the outdoor patio and the awesome central location
Hot tub was great in the evenings
hot tub and bikes were awesome
We loved the location- close to the river and town
We enjoyed our stay here Great location and the bikes make it easy to get around
We really liked being in a neighborhood as opposed to the condo complex
Hot tub was great at the end of a day of skiing
Beautiful home in a fantastic location Short walk to downtown and the river Beautiful city FYI
We had a great time after work went for walks and mostly enjoyed the wonderful location We are looking forward to stay here again
Read more reviews
Earn OneKeyCash for every dollar spent on eligible hotels, vacation rentals, flights, car rentals, and more when you book across our family of brands.

5. Westside craftsman bungalow (from USD 249)

Built in 1919, this bungalow is listed in the National Historical Register. You will find most of its historical elements preserved with the addition of modern conveniences such as central air conditioning and heating, dishwasher, and more! Stay and relax in the large private backyard. It is fully enclosed with a fence, covered with grass, has a barbeque, comfortable seating, and a patio umbrella. Explore further and take a walk in the quiet and vibrant neighborhood that will truly make you feel the Bend atmosphere. There are two bedrooms to comfort you after a tiring day. Every room has a queen-sized bed with soft sheets and a comforter.

Stayed at this property?

898 meters (0.6 ft) from Drake Park
158 reviews   Wifi Available
House 6 Guests 2 Bedrooms 1 Bathroom

Accommodates: 6
Minimum Nights: 2
Refund Policy : 100% refund if you cancel at least 60 days before check-in.

Top guest reviews
Amenities & Room:
The living room setup with comfy couch and chairs next to the gas fireplace offered a cozy place to relax after skiing
The kitchen is stocked with all the supplies needed
The updated and modern jack and jill bathroom was a nice touch
It is comfortable and cozy and also has all the things you need
The home has the old craftsman look and feel with comfortable furnishings and tasteful modern updates (lovely gas fireplace terrific updated kitchen and bathroom)
Everything is clean and neat
The house was so inviting
We absolutely loved the home
This beautiful property put us into vacation mode immediately and the owners were responsive and friendly with minor issues that required communications such as city utility upgrades
We appreciated the amenities and the welcome card Thanks for letting us live in your cute rental home during our spring vacation
The owners are very easy to communicate with Five stars for sure
The decor is welcoming and our family made lots of memories during our holiday stay
Beautiful renovated bungalow in a perfect location The best grocery store Market of Choice is right around the corner
It has the best location to all the fun activities in Bend
The market nearby was amazing Perfect set up for a great time in Bend
Brewery very close to house
Firstly this property is in a perfect location to explore downtown and the old mill district
Read more reviews
Earn OneKeyCash for every dollar spent on eligible hotels, vacation rentals, flights, car rentals, and more when you book across our family of brands.

6. Serene and private cottage near downtown Bend

This place is called “The Little House,” but it’s not that little as you will find when you book it. Some of the words used by guests to describe it are “magical,” “romantic,” “serene hideaway,” and “private paradise.” This is a self-catering cottage located in midtown Bend with a spacious floor plan ideal for up to three guests. It has a private entrance and private parking for two cars, a full kitchen, a library, and a private master bedroom. It’s tucked in a diverse neighborhood with convenience stores, restaurants, and shops in nearby locations. Make sure to take advantage of downtown Bend, where you can spend the night with good friends, good food, and good drinks.

Stayed at this property?
Bend, Oregon, United States
1.81 km (1.2 mi) from Drake Park
434 reviews   Wifi Available
Entire guesthouse 2 Beds 3 Guests 1 Bedroom 1 Bathroom

Accommodates: 3

Top guest reviews
Amenities & Room:
it has a full kitchen loads of little amenities and fit our needs perfectly
the bed was comfortable the kitchen was great and we had all the amenities we needed
there's no tv but i honestly loved that forced us to disconnect for the weekend we were there
we had a wonderful stay at the little house plenty of space nice kitchen great hot tub
the space is cozy and relaxing
it was very clean and had everything we could possibly need
the bathroom is efficient and super clean again well stocked
super clean deb was so friendly and responsive
the place was very clean the hot tub was relaxing
clean well-organized space
debby and kevin are excellent hosts
debby and kevin are excellent hosts
deb & kev are fantastic hosts
debby and kevin make completely great hosts
hosts were very helpful:
great location highly recommend
loved staying here great location
an easy walk to many shops and restaurants
we enjoyed the hot tub and the location was ideal for our concert
duck hollow was an ideal place for the two of us
Read more reviews

7. Elegant loft at Westside Bend

This rental is a modern space with a contemporary design. It is tucked amongst the juniper trees, making it a perfect spot for those who like it quiet and peaceful. The High Desert Loft features a gorgeous, fully-equipped gourmet kitchen with brand new appliances, concrete and black walnut countertops, glass subway tiles, and beautiful modern finishings throughout. The master bedroom offers restful evenings whatever the season is. The bed is covered with soft, quality sheets, with cosy down duvet and a custom barn wood headboard. From here, you can access the bathroom with a rustic barn finish. It also has a bathtub and a shower to cool you down or warm you up. Are you booking with kids? There is a fold-out couch in the living room that transforms into a double bed. Extra bedding is also provided in the master closet.

Stayed at this property?
Bend, Oregon, United States
1.05 km (0.7 mi) from Drake Park
351 reviews   Superhost Wifi Available
Entire guesthouse 2 Beds 4 Guests 1 Bedroom 1 Bathroom

Accommodates: 4

Top guest reviews
Amenities & Room:
tasteful decor great kitchen comfortable furniture & bed
kitchen layout and amenities are thoughtful and efficient
the king bed is super comfortable
the location of this home is perfect we walked to grab coffee and breakfast
nice quiet space very clean and modern
the apartment is clean and spacious
everything was super clean modern and well laid out
such an awesome place clean stylish and spacious
the guest house was sparkling clean and extremely comfortable
jenna is an amazing host
jenna is a great host
jenna & shawn we’re awesome hosts with a wonderful space
jenna was a great host
and a fantastic host
the location is fantastic
great location and very comfortable
beautiful loft and perfect location
this place is settled in a great location not far from downtown
darling apartment in a fantastic location
Read more reviews

Visit bold and beautiful Bend

Bend is all about character, boldness, and style. It speaks right in front of you the moment you step into its shops or take a walk in its neighborhoods. This unique feature is also seen and felt in the homes featured in this list. Whatever you choose, you’re sure to enjoy lots of private space, a dash of nature (and sunshine), and a welcoming vibe that is uniquely Bend. Book your vacation home now before somebody else does!

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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Carmela Ann Santos is a freelance writer and a licensed teacher from the Philippines. Her top destinations would include any place with a clear view of cloud formations and peaceful waters. She...Read more

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