Photo by Hannah Martini

Old Bend holiday rentals

We found 348 holiday rentals — enter your dates for availability
Discover a selection of 62 homes and other holiday rentals in Old Bend that are perfect for your trip. Holiday rentals offer the best amenities for your family, friends or furry companion, such as air conditioning and a pool. You'll be sure to find a property to rent that has what everyone needs, including places that are non-smoking or accessible.

Holiday rentals with weekly discounts – Old Bend

Showing deals for:25 Dec - 1 Jan

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
Mini Split heats and cools the Great Room and bedroom. French Doors to patio
Exceptional
(222 reviews)

Immaculate Cottage-EV charger-4 mins walk downtown-extended stays welcome

Bend

6% off
AU$2,796
for 7 nights, 1 cottage
AU$399 per night
includes taxes & fees
Immaculate Cottage-EV charger-4 mins walk downtown-extended stays welcome
Private kitchen
Interior
Living area
Exterior
Exceptional
(6 reviews)

Modern Nordic Nest: Sauna & Stroll to Galveston Ave

Bend

8% off
AU$9,961
for 7 nights, 1 home
AU$1,423 per night
includes taxes & fees
Modern Nordic Nest: Sauna & Stroll to Galveston Ave
782E5D86-B7D6-4BE7-B9FE-B6A6A96EF4E2.jpeg
475278F8-70B1-4570-9F9F-26ECCC39D838.jpeg
Exterior
471F239B-3233-4EFC-9C1F-EC0AC5853E2A.jpeg
Exceptional
(44 reviews)

Downtown Craftsman with King Bed and Private Yard - Walk Everywhere

Bend

12% off
AU$5,865
for 7 nights, 1 home
AU$838 per night
includes taxes & fees
Downtown Craftsman with King Bed and Private Yard - Walk Everywhere
New stainless appliances and fully stocked kitchen.
Property grounds
Laundry Room: Full in-unit laundry facilities to handle all your outdoor gear.
Morning coffee on the porch of this original 110-year-old Bend classic.
Exceptional
(95 reviews)

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

Bend

8% off
AU$2,687
for 7 nights, 1 home
AU$384 per night
includes taxes & fees
Historic 1917 cottage by the river, walkable to all of downtown Bend!
Exterior
Summer on the river
Living area
View of river from back deck
Exceptional
(201 reviews)

Riverfront Cottage -Near Drake Park, Walk to Town.

Bend

23% off
AU$2,087
for 7 nights, 1 home
AU$298 per night
includes taxes & fees
Riverfront Cottage -Near Drake Park, Walk to Town.
Take the Cruiser bikes for a spin around town
Evening relaxation on the private back patio
Dining
Interior
Exceptional
(17 reviews)

Mckay Getaway, between Drake Park/Miller's Landing

Bend

8% off
AU$4,028
for 7 nights, 1 home
AU$575 per night
includes taxes & fees
Mckay Getaway, between Drake Park/Miller's Landing
Outdoor dining
Exterior detail
Front of House
Interior
Exceptional
(170 reviews)

Bends Westside Kaleana's Garden Cottage

Bend

8% off
AU$2,554
for 7 nights, 1 home
AU$365 per night
includes taxes & fees
Bends Westside Kaleana's Garden Cottage

  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Frequently asked questions

When is the best time to visit Old Bend for a holiday rental?
The most popular time to visit Old Bend is during the peak season from May to July, when the region comes alive with outdoor enthusiasts eager to experience its stunning natural beauty. With average temperatures ranging from 10 to 30 degrees Celsius, this period is superb for enjoying a variety of activities such as hiking, river rafting, and exploring the local craft beer scene.July, in particular, is the highlight of the summer, attracting both adventure seekers and families looking to make the most of the warm weather. Visitors can participate in numerous outdoor festivals and events that showcase the vibrant community spirit of Old Bend, all while soaking in the gorgeous landscapes of the Deschutes River and the surrounding mountains.For those seeking a more budget-friendly option, October offers an excellent chance to enjoy the peaceful beauty of Old Bend. During this month, you can witness the stunning autumn colours as the leaves change, creating a picturesque backdrop for leisurely walks and scenic drives. Additionally, the tourist crowds have thinned, providing a more relaxed atmosphere to explore local shops and enjoy the culinary delights without the hustle and bustle.Ultimately, the best time for your holiday rental in Old Bend will depend on whether you prefer the lively summer buzz filled with activities or the tranquil charm of autumn's embrace.
What are the top attractions in Old Bend, Oregon, United States of America?
In Old Bend, Oregon, visitors can experience firsthand a variety of attractions that showcase the area's natural beauty and local culture. The Deschutes River runs through the heart of the town, offering picturesque views and opportunities for activities such as kayaking and fishing. The riverfront area is great for leisurely strolls and enjoying the scenic surroundings.The Old Mill District is another highlight, featuring charming shops, restaurants, and art galleries set against a stunning backdrop of the Cascade Mountains. This area hosts various events and festivals throughout the year, making it a lively spot for both locals and visitors.For those interested in outdoor adventures, the nearby Pilot Butte State Scenic Viewpoint provides a fantastic vantage point for panoramic views of the surrounding landscape and is a popular hiking destination.
Are all fees included in the Old Bend holiday homes prices shown on Stayz?
Stayz 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.
Are there any Old Bend holiday homes with parking?
Stayz offers a wide selection of holiday homes in Old Bend with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details 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.
Are there any discounts for Old Bend holiday homes?
You can find great discounts on holiday homes in Old Bend on Stayz, 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.
Can I change or cancel my Old Bend holiday home booking on Stayz?
To find Old Bend holiday rentals with free cancellation, just use Stayz'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". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Old Bend?
A long-stay holiday home in Old Bend is the best way to experience local living. Plus, you can make the most of long-stay discounts. 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.
Can I plan a group trip on Stayz?
Stayz's Trip Planner makes organising 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 favourites, and build the perfect itinerary together.
How early should I book a Old Bend holiday home?
Book your Old Bend holiday home 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 Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Old Bend?
Prices for holiday homes in Old 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 travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in Old Bend to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, 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.
Why should I join Stayz as a host?
Joining Stayz as a host opens the door to a global community of travellers 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, Stayz makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

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