Downtown Bend vacation rentals

We found 319 vacation rentals — enter your dates for availability

Nestled in the heart of Central Oregon, Bend beckons with its breathtaking landscapes, vibrant neighborhoods, and an abundance of outdoor adventures. From kayaking along the picturesque Deschutes River to hiking scenic trails, this destination is perfect for families and groups seeking both excitement and relaxation. Wander the charming streets of Old Bend or savor local brews at the annual Brewfest. With diverse vacation rentals that range from cozy cabins to spacious condos, you can enjoy a home-like experience while immersing yourself in the local culture and natural beauty.

Holiday rentals with weekly discounts - Downtown Bend

Showing deals for:Nov 13 - Nov 20

Breakfast bar and kitchen
Beautifully appointed living spaces
New Chef's kitchen with quartz counters, high-end applicances,
Bedroom four kitchette with Keurig coffee maker, microwave, toaster oven, fridge
Excellent
(8 reviews)

Location! Historical District Downtown - Walk everywhere, new 4 Bedroom, 3 Bath

Bend

8% off
$695
$4,864 for 7 nights
All fees included
Location! Historical District Downtown - Walk everywhere, new 4 Bedroom, 3 Bath
Tranquil setting - hidden gem in the heart of Bend
While relaxing  on the cottage patio, guests are often enticed to see more
Complete kitchen with 4 burner stove, Microwave and Bosh dishwasher
Secluded, quiet, and peaceful luxury in a retreat like setting
Exceptional
(218 reviews)

Immaculate Downtown Cottage Retreat- EV charger. Walk downtown in 4 minutes

Bend

7% off
$268
$1,876 for 7 nights
All fees included
Immaculate Downtown Cottage Retreat- EV charger. Walk downtown in 4 minutes
Exterior
Living area
Interior
Property grounds
Exceptional
(43 reviews)

Cozy Up at a Nature Inspired Boutique Studio in the Trees - River Nearby

Bend

13% off
$147
$1,032 for 7 nights
All fees included
Cozy Up at a Nature Inspired Boutique Studio in the Trees - River Nearby
Terrace/patio
Property grounds
New stainless appliances and fully stocked kitchen.
Morning coffee on the porch of this original 110-year-old Bend classic.
Exceptional
(94 reviews)

Historic 1917 cottage by the river, walkable to all of downtown Bend!

Bend

8% off
$226
$1,585 for 7 nights
All fees included
Historic 1917 cottage by the river, walkable to all of downtown Bend!
Exterior
Summer on the river
View of river from back deck
Living room
Exceptional
(192 reviews)

Riverfront Cottage -Near Drake Park, Walk to Town.

Bend

25% off
$177
$1,238 for 7 nights
All fees included
Riverfront Cottage -Near Drake Park, Walk to Town.
Comfy spacious living room.  Has a sleeper sofa.
Easy access to the river from the back yard. Put in kayaks, SUP's or floats.
Love the granite we choose.
Steps down to the yard and water.
Exceptional
(198 reviews)

RIVERFRONT COTTAGE EPIC WALKABLE LOCATION ON RIVER

Bend

9% off
$843
$5,903 for 7 nights
All fees included
RIVERFRONT COTTAGE EPIC WALKABLE LOCATION ON RIVER
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Exterior
Exceptional
(44 reviews)

Downtown Craftsman with King Bed and Private Yard - Walk Everywhere

Bend

13% off
$198
$1,384 for 7 nights
All fees included
Downtown Craftsman with King Bed and Private Yard - Walk Everywhere
Living room with windows overlooking front yard includes fireplace & cable tv.
The Bend Bungalow awaits! Set up high off street level is your quiet retreat.
The kitchen is fully stocked down to the wine bottle opener.
Dining
Exceptional
(138 reviews)

Bend Bungalow - a Walk in the Park to Downtown and River!

Bend

7% off
$153
$1,070 for 7 nights
All fees included
Bend Bungalow - a Walk in the Park to Downtown and River!
smart TV with cable
Westlake Cottage on a mid-summer day
washer/dryer hides away when not needed
Sunny cozy nook in south bedroom for quiet relaxation
Exceptional
(12 reviews)

Westlake Cottage - Great Weekly & Monthly Rates - walk Downtown

Bend

40% off
$175
$1,227 for 7 nights
All fees included
Westlake Cottage - Great Weekly & Monthly Rates - walk Downtown
Backyard BBQ Spot.
Wrens Nest with front yard.
A complete media center including Netfix and Hulu.
Tiny dining table can still seat four.
Exceptional
(118 reviews)

Wren's Nest Updated Historic Home In The Heart Of Bend.

Bend

6% off
$156
$1,093 for 7 nights
All fees included
Wren's Nest Updated Historic Home In The Heart Of Bend.
Front of House
Exterior detail
Interior
Dining
Exceptional
(164 reviews)

May special Bends Westside Kaleana's Garden Cottage

Bend

8% off
$239
$1,672 for 7 nights
All fees included
May special Bends Westside Kaleana's Garden Cottage
Exterior
Living area
Private kitchen
Dining
Wonderful
(25 reviews)

Heart of Bend-Walkable, Ping Pong, Billards

Bend

8% off
$331
$2,315 for 7 nights
All fees included
Heart of Bend-Walkable, Ping Pong, Billards
Interior
Living area
Living area
Room
Exceptional
(27 reviews)

Hillside Haven: Tranquil NW Studio Near the River

Bend

13% off
$127
$892 for 7 nights
All fees included
Hillside Haven: Tranquil NW Studio Near the River
  • Peace of mind

    Our Book with Confidence guarantee gives you 24/7 support
  • All the privacy of home

    Enjoy full kitchens, laundry, pools, yards and more
  • More for less

    More space, more privacy, more amenities — more value
  • A place for everyone

    We stand for diversity, inclusion and families everywhere.
    Learn more

Frequently asked questions

How much does it cost to rent a vacation home in Downtown Bend?
Prices for vacation rentals in Downtown Bend vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Downtown Bend to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Downtown Bend vacation house rentals?
You can find great discounts on house rentals in Downtown Bend on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Are there any Downtown Bend vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Downtown Bend with parking available—perfect for families or travelers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Can I find long-stay vacation rentals in Downtown Bend?
A long-stay vacation rental in Downtown Bend is the best way to experience local living. Plus, you can make the most of long-stay discounts. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search. *Based on analysis of Vrbo booking and occupancy data for 2024 stays.
When is the best time to visit Downtown Bend for a vacation rental?
The most popular time to visit Downtown Bend is during the peak season from May to July, when the vibrant energy of summer transforms the area into a hub of outdoor activities and local events. This period attracts travelers eager to experience the stunning landscapes, craft breweries, and vibrant dining scene that Bend is known for. With average temperatures ranging from the mid-60s to low 80s Fahrenheit, it's a superb time for outdoor adventures like hiking, paddleboarding, and exploring the nearby Deschutes River.July, in particular, stands out as the busiest month, with visitors flocking to enjoy the warm weather and participate in various festivals and activities. The bustling atmosphere makes it an exciting time to experience Bend's lively culture, but be prepared for larger crowds and higher rental prices.For those seeking a more budget-friendly option, consider visiting in October. This month offers a quieter experience with beautiful fall colors painting the landscape, making it an ideal time for scenic drives and leisurely strolls. With fewer tourists, you can enjoy more intimate visits to local shops and eateries while still soaking in the charm of the town.Ultimately, the best time to visit Downtown Bend for a vacation rental depends on your preferences for activity levels and ambiance.
How early should I book a Downtown Bend vacation rental?
Book your Downtown Bend vacation rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Downtown Bend, Oregon, United States of America?
In Downtown Bend, visitors can enjoy a variety of attractions that highlight the area's natural beauty and vibrant culture. The Deschutes River runs through the heart of the downtown area, providing opportunities for kayaking, paddle boarding, and scenic riverside walks. The popular Drake Park offers lush green spaces and picnic areas, great for relaxation and enjoying the views of the river and surrounding mountains.The downtown area is also home to a thriving arts scene, with numerous galleries and art installations, particularly along Wall Street and Oregon Avenue. The High Desert Museum, located just a short drive from downtown, showcases the region's natural history and cultural heritage, making it a must-visit for those interested in local wildlife and Native American history.Foodies will find a number of dining options, including local breweries and farm-to-table restaurants, particularly concentrated around Minnesota Avenue. The Bend Ale Trail is a popular attraction for beer lovers, featuring a number of craft breweries within walking distance of downtown.
Can I change or cancel my Downtown Bend home rental booking on Vrbo?
To find Downtown Bend vacation rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travelers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cozy cabin or a beach condo, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Downtown Bend vacation rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively. Vrbo also offers support via live chat through our Help Center, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organizing group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.