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

Excellent
(8 reviews)
Location! Historical District Downtown - Walk everywhere, new 4 Bedroom, 3 Bath
Bend
$695
$4,864 for 7 nights
All fees included

Exceptional
(218 reviews)
Immaculate Downtown Cottage Retreat- EV charger. Walk downtown in 4 minutes
Bend
$268
$1,876 for 7 nights
All fees included

Exceptional
(43 reviews)
Cozy Up at a Nature Inspired Boutique Studio in the Trees - River Nearby
Bend
$147
$1,032 for 7 nights
All fees included

Exceptional
(94 reviews)
Historic 1917 cottage by the river, walkable to all of downtown Bend!
Bend
$226
$1,585 for 7 nights
All fees included

Exceptional
(192 reviews)
Riverfront Cottage -Near Drake Park, Walk to Town.
Bend
$177
$1,238 for 7 nights
All fees included

Exceptional
(198 reviews)
RIVERFRONT COTTAGE EPIC WALKABLE LOCATION ON RIVER
Bend
$843
$5,903 for 7 nights
All fees included

Exceptional
(44 reviews)
Downtown Craftsman with King Bed and Private Yard - Walk Everywhere
Bend
$198
$1,384 for 7 nights
All fees included

Exceptional
(138 reviews)
Bend Bungalow - a Walk in the Park to Downtown and River!
Bend
$153
$1,070 for 7 nights
All fees included

Exceptional
(12 reviews)
Westlake Cottage - Great Weekly & Monthly Rates - walk Downtown
Bend
$175
$1,227 for 7 nights
All fees included

Exceptional
(118 reviews)
Wren's Nest Updated Historic Home In The Heart Of Bend.
Bend
$156
$1,093 for 7 nights
All fees included

Exceptional
(164 reviews)
May special Bends Westside Kaleana's Garden Cottage
Bend
$239
$1,672 for 7 nights
All fees included

Wonderful
(25 reviews)
Heart of Bend-Walkable, Ping Pong, Billards
Bend
$331
$2,315 for 7 nights
All fees included

Exceptional
(27 reviews)
Hillside Haven: Tranquil NW Studio Near the River
Bend
$127
$892 for 7 nights
All fees included
Find spaces that suit your style
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Find the best place to stay - Downtown Bend

***NEW*** Charming home located in Downtown Bend!
Sleeps 6 · 2 bedrooms · 1 bathroom

Luxury Rooftop Condo in the Heart of Downtown Bend, Cascade Mountain views
Sleeps 4 · 2 bedrooms · 2 bathrooms

Mirror Pond - Cozy Cabin Directly on Mirror Pond - Deschutes River!
Sleeps 6 · 2 bedrooms · 2 bathrooms

Modern cottage charm & walk to Downtown Bend
Sleeps 6 · 3 bedrooms · 1 bathroom

3 Bedroom house 2 blocks from down town Bend
Sleeps 6 · 3 bedrooms · 1 bathroom

Bend Waterfront Home: Hot Tub, Walk to Town
Sleeps 8 · 3 bedrooms · 2+ bathrooms
Top rated rentals - Downtown Bend

Peace of Mind and comfort!
We throughly enjoyed our stay in this beautifully decorated, clean, and well stocked property for our 9th anniversary. You can see from the moment you walk through the door it is taken care of with great pride, we were very grateful for all the comforts of home and the beautiful decor and amenities.
The host Emily was very responsive and welcoming, we would definitely make arrangements for a longer stay in the future!
Emily, Thank you Very much for sharing your beautiful property!!!
Rich & Laura
Richard L.
Stayed Jun 2024

Bend biking
Everything was great.
John S.
Stayed Jun 2024

Great family vacation in Bend
The property was perfect for us. The location is key as it is easy walking to downtown and also Drake Park, the Lot, and many breweries. We took day trips to Crater Lake, Smith Rock (hiked the 8 mile loop), kayaked on the river and then floated on the river on a warm and sunny day. Also took a day trip to the McKenzie Falls loop and Clear lake. Mountain biked with Cog Wild. It was nice to come back to the house after a good day and have a beer and then a short walk to dinner and more beer. Also took 26 to the fossil beds museum and Painted Hills. We were busy this week.
The front room was bigger than I expected and comfortable for night time TV watching. Also, worth noting was how incredibly stocked the house was, TP, PT, dish and laundry tabs etc it was there and plentiful.
Check in was simple. Neighborhood was quite. There were Subarus everywhere lol
See ya next time.
Carl C.
Stayed Jun 2023
- Peace of mindOur Book with Confidence guarantee gives you 24/7 support
- All the privacy of homeEnjoy full kitchens, laundry, pools, yards and more
- More for lessMore space, more privacy, more amenities — more value
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.
