10 Great Vacation Rentals For Older Travellers In Bend, Oregon - Updated 2023

10 Great Vacation Rentals For Older Travellers In Bend, Oregon - Updated 2023

Bend, Oregon, is a place to relax and enjoy the outdoors. Terrains and sights are plenty and varied so there’s always lots to do. It doesn’t come as a surprise then, that it’s a top choice for retirees, who make a significant chunk of the city’s population. As such, many of the city’s facilities and entertainment options are made by and cater to them, with a lot of outdoor activities, arts and crafts and a lot of peace and quiet. Here, we’ve compiled a list of 10 Airbnb vacation rentals that are great for older occupants - many of which have wheelchair friendly or pet-friendly compounds.

1. A suite in an even sweeter environment

If you need a quiet, functional stay with a little bit of style, here is an Airbnb room that will suit you. Small touches of trendy, chic decor give the place a little charm. Potted plants are scattered through the house to bring a sense of freshness. A spacious area, large windows, a comfortable bed and a private bathroom make your little suite for two. This private, clean environment with understanding hosts is a great place for you to get your thoughts running. Here, you are welcome to use the kitchen, the front porch, the back deck and the running room upstairs.

Kingston Kottage
Bend, Oregon, United States
160 reviews Superhost  Wifi Available
Entire guesthouse 1 Bed 2 Guests 1 Bedroom 1 Bathroom

Accommodates: 2

Top guest reviews
Amenities & Room:
breakfast of fruit cookies and coffee was a perfect start to every day
very nice bed and bath linens
we're so appreciative of all mike and jill did to make the stay comfortable
no question that these guys are superhosts the breakfasts they supplied us with were perfect for our needs
thoughtful and nice touches like these made my stay that much more cozy
clean and very comfortable
very clean and perfect for two people
well stocked and clean
the room was clean and comfortable and the house as a whole is beautiful
this place is cozy clean and just big enough for two people
mike was an excellent host
mike and jill are great hosts
mike and jill are great hosts
mike and jill have been wonderful hosts
mike and jill were awesome hosts
they are located in an ideal location
the location is wonderful and walkable/central
the location was awesome
location is number one and comfort is a close second
the location for exploring town was great
Read more reviews

2. Great location with warm and elegant decor (from 95 USD)

This modern Airbnb home full of natural light and indoor greenery has all the tranquil vibes you need to clear your mind and take a breather. It is located in the historic Little Italy neighbourhood, which is experiencing a revival in the local arts scene so you can visit the open mics, bars and theatres nearby for some fun and inspiration. The vacation rental you will be staying in is clean and minimal with space for two guests. Space for a maximum of two other guests is available on the futon/sofa. It’s on the small side, so the owner encourages guests to hang out in the common areas. You are free to use the clean and green backyard cabana as well.

Contemporary Cottage in the Country

Address: Bend, OR, United States (see map)

Price: from 95 USD

Number of Guests: 4

3. Hearty breakfasts and rich experiences (from 98 USD)

Past guests have described their experience at this cosy bed and breakfast forest suite an ‘adventure through the woods’. Framed by colourful trees and owned by warm and sweet hosts, Melinda and Tom, a stay at this Airbnb vacation rental is more like meeting new friends in an interesting forest setting rather than just being someone’s house guests. One bed sleeps two guests - complete with heated blankets and a bathroom with heated tiles. Fresh, delicious breakfasts are also provided. The Airbnb place is wheelchair accessible and small pets are negotiable.


Address: Sunriver, OR, United States (see map)

Price: from 98 USD

Number of Guests: 2

4. Learning and leisure

The charming, relaxing atmosphere of this Airbnb home is perfect for those who prefer a quiet retreat for the holidays. Lifelong bookworms can fulfill their dreams of living in a library with the house’s extensive collection of reading materials. It’s also centrally located to the mountains, other recreational activities and cuisine. Walk or bike to Bend’s favourite attractions. The vacation rental can sleep four guests with one queen bed in the bedroom and a large futon in the living room. A full kitchen is available for you to prepare your own meals. Need a reading buddy? Bring your pet along to sit on your lap as you pore over the pages.

Home away from Home (aka Book House)
Bend, Oregon, United States
600 reviews Superhost  Wifi Available
Entire guesthouse 1 Bed 4 Guests 1 Bedroom 1 Bathroom

Accommodates: 4

Top guest reviews
Amenities & Room:
bed was comfortable and enjoyed the small kitchen amenities available for our stay
it has a well-equipped kitchen and the books are amazingly diverse and fun to look through
very clean and comfortable space
cleanliness comfort and cool decor
everything was clean and we didn't want for anything
the place was cozy clean and comfortable
comfortable bed quiet neighborhood great kitchen space clean and cozy
mark and stephanie were excellent hosts
mark and stephanie were great hosts
hosts were very helpful and responsive
hosts were very responsive and helpful
the hosts are wonderful and very quick to respond
easy walking distance to restaurants
great location & great space
very cute and in a super convenient walkable location
the location was great- tucked away in a beautiful neighborhood but about a 15 minute walk to town
great location with a nice place to park
Read more reviews

5. Cottage in the heart of Bend

This Airbnb cottage in an incredibly convenient location is for those looking to get in touch with their free-spirited selves. Colourful, bohemian and bright, this vacation rental is close to Bend’s favourite breweries and restaurants. A sociable host who knows Bend’s best kept secrets plus two very cute labradoodles make for a fun-filled stay that you won’t want to leave. The room you’ll stay in is comfy, spacious and bright with a real bed, which sleeps 2. The rest of the house is shared, with a kitchen ready for you to cook in and a barbeque that’s all fired up to grill some marshmallows!

Charming Cottage in Heart of Bend
Bend, Oregon, United States
185 reviews Superhost  Wifi Available
Private room in home 1 Bed 2 Guests 1 Bedroom 1 Bathroom

Accommodates: 2

Top guest reviews
Amenities & Room:
the living room is also super comfy and decorated nicely with a lovely deck and outdoor seating area
very warm cozy home with a wonderful deck
even though this is a “private room” it feels more like an entire home
the house is colorful and cozy with many areas to relax
very comfortable with her beautiful art giving it a fun colorful touch
the room was especially clean and cozy
it is very clean spacious and has a lot of charm
the room was clean and the outdoor space is amazing
the house and our room and bathroom were all really clean and cozy and we had everything we needed
the house is clean and quiet and filled with her creative touches
she was a great host
she was friendly and a great host
the labradoodles were friendly and adorable
marci is a great host
marci was a great host
nice location easy walking around bend
wonderful location: within walking or biking distance to the the heart of bend
centrally located and easy to walk many places
outstanding location within walking distance of all bend has to offer
great location in bend - walkable to downtown old mill district close proximity to deschutes river trail
Read more reviews

6. Little house by the river

This compact Airbnb vacation rental, aptly named the trout house, has direct river access. Enjoy peaceful views of calm waters from your bedroom window, and step outside to watch beautiful sunrises. From here, you get direct access to this river which is great for kayaking and floating. In this peaceful, riverside setting, time slows down and things feel a world away from the city, but it’s really only a short walk away from downtown. It’s located near many Westside Bend shops and eateries. With one bed, it is ideal for two guests. It also comes with a kitchenette and a laptop friendly workspace.

Trout House, Best Location in Bend
Bend, Oregon, United States
217 reviews  Wifi Available
ENTIRE HOME 1 Bed 2 Guests 0 Bedrooms 1 Bathroom

Accommodates: 2

Top guest reviews
Amenities & Room:
we walked everywhere the room was perfect and her amenities were above expectations
amazing amenities the host thought of everything - breakfast snacks coffee even a growler we could use
cozy spot with a gorgeous view you step outside your room and you’re at the deschutes river
sit next to the river or enjoy it from the comforts of the viewing area in the apartment
it's a cute cozy natural light filled spot perfect for 2 that any river lover would enjoy
place was very clean
clean cozy place next to the river
the trout house itself is clean quiet and comfy
super clean and nice welcoming amenities
the cottage is clean very nicely provisioned and the bed is really comfortable
hosts were so helpful
the hosts were helpful and attentive
the host was friendly and walked us through check in
deanna is a great host very friendly and helpful
deanna was extremely friendly and helpful excellent host
the location is amazing
great location close to fantastic restaurants and shopping
wonderful location right on the river
great location easy walking distance to downtown and nearby restaurants
great location right on the river
Read more reviews

7. Surrounded by graceful willow trees (from 195 USD)

This elegant little Airbnb cottage is just 12 feet from the Deschutes River. Days spent watching fellow kayakers framed by swaying willow trees is surely a soothing sight. It has a large walk in shower, a microwave, a refrigerator, an outdoor grill and many other kitchen appliances. A queen bed and a sofa bed provide sleeping arrangements for three guests. This listing is also wheelchair friendly and pet-friendly - it is located in a friendly, dog-owning neighbourhood.

River Willow Cottage

Address: Bend, OR, United States (see map)

Price: from 195 USD

Number of Guests: 3

8. A retreat in Old Mill

This cosy Airbnb vacation rental, named The Fox Lodge, is a 10-minute walk to the Old Mill District, which is brimming with activities; shopping, movies, concerts, ice skating rinks and even a whitewater park. The house itself is a charmer, with a cosy fireplace and natural wood to create a Northwestern feel. It’s also incredibly spacious and has a roll-in shower, making it wheelchair accessible. Three bedrooms with five beds, consisting of two queen beds, two single beds and a sofa bed make sufficient sleeping corners for six.

“This Mountain Town Has It All” Furnished Upscale
Bend, Oregon, United States
15 reviews  Wifi Available
Entire townhouse 4 Beds 5 Guests 3 Bedrooms 3 Bathrooms

Accommodates: 5

Top guest reviews
Amenities & Room:
the beds are extremely comfortable and the decor in each room is top notch
we did find the kitchen well equipped and prepared some of our meals in
the neighborhood was quiet and very clean as well
the home was beautiful very clean and well kept
terri is a great host
terri is a great host who responds quickly
terri is a fabulous host with a beautiful home
terri was friendly and helpful
we highly recommend the fox lodge to other visitors an d found terri helpful and considerate
the location was perfect for skiing shopping and restaurants
she had everything we needed and the location is ideal
the location was within an easy walk to the old mill district and the home itself was beautiful
Read more reviews

9. Bright and spacious luxury home

This luxury Airbnb vacation rental is surrounded by hip and delicious cuisine options, from high-end restaurants to beer gardens. It is clean, new and spacious - recently custom built to fit a family of six. Everything from a flat screen TV for movie night to exercise rooms to keep active are available here. A private side patio with fresh herbs and berries allows you to add fresh produce to your cooking. The master bedroom has a king sized bed, while bedrooms 2 and 3 both have a queen sized bed. With so much to do in this home and all these amenities by your side, you can just focus on relaxing and taking life one day at a time.

Walk to Everything! Clean & Modern
Bend, Oregon, United States
2 reviews  Wifi Available
ENTIRE HOME 3 Beds 6 Guests 3 Bedrooms 2 Bathrooms

Accommodates: 6

Top guest reviews
john was an absolute wonderful host
Read more reviews

10. Sunny days in Sunriver

This executive Airbnb home with excellent amenities is a great option for a large group of travellers. Some of the entertainment options this place provides are a hot tub, flat screen television, pool passes for unlimited use, books and games. Dirt trails for hiking are quite close by as well. It’s family friendly, pet-friendly and wheelchair accessible, so you can bring everyone along to this custom home, summertime getaway.

Executive Home in Sunriver, Oregon
Sunriver, Oregon, United States
94 reviews  Wifi Available
ENTIRE HOME 5 Beds 10 Guests 3 Bedrooms 2 Bathrooms

Accommodates: 10

Top guest reviews
Amenities & Room:
the beds were unbelievable comfortable
only other wish was for air conditioning
sleeping arrangements are good but beds are just ok
we loved the back tv-couch/dining area we'll be back next year for sure
we had plenty of room for our family and the beds are very large as well as comfortable
space was clean and well organized
the house was very clean and nice
the interior is clean and new
lots of clean towels to use lots of extra toilet paper/paper towels stocked
it was clean nice comfortable and well stocked
david was an excellent and attentive host
david was available and helpful
david was also super responsive to our questions
dave was a great host
dave is a great host to work with
great location especially in the winter
very nice house in good location
great house location and quiet neighborhood
the house and location was perfect for our family vacation
the kids loved going and also close to the village center for restaurants
Read more reviews

Slow down and enjoy simple pleasures in Bend, Oregon

Hiking, walking the dog, sitting by the river - these are things that sound simple but these days, as more and more of us live life in the bustling, busy cities, become luxuries. However, a laidback and friendly location like Bend allows you to take the time off to allow yourself the rest, relaxation and exploration you crave. With these 10 relaxing and convenient Airbnb vacation rentals, we hope we’ve given older travellers excellent options to look at when travelling to Bend.

Disclosure: Trip101 selects the listings in our articles independently. Some of the listings in this article contain affiliate links.

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My name is Kimberlyn, I'm a huge fan of interesting stories and places. I love memorizing wicked facts and quirky histories. I also draw a lot on the side.

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