Photo by Hannah Martini

Old Bend holiday lettings

We found 347 holiday rentals — enter your dates for availability
Discover a selection of 63 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:20 Nov - 27 Nov

Living area
Just outside these windows is a wrap around deck to play on.
Private kitchen
Dining
Exceptional
(104 reviews)

Fantastic view of Bend with pickleball and basketball court

Bend

7% off
£2,246
for 7 nights, 1 home
£321 per night
includes taxes & fees
Fantastic view of Bend with pickleball and basketball court
Tranquil setting - hidden gem in the heart of Bend
While relaxing  on the cottage patio, guests are often enticed to see more
Mini Split heats and cools the Great Room and bedroom. French Doors to patio
Complete kitchen with 4 burner stove, Microwave and Bosh dishwasher
Exceptional
(220 reviews)

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

Bend

6% off
£1,470
for 7 nights, 1 cottage
£210 per night
includes taxes & fees
Immaculate Downtown Cottage Retreat- EV charger. Walk downtown in 4 minutes
Property grounds
Interior
Private kitchen
Exterior
Exceptional
(5 reviews)

Modern Nordic Nest: Sauna & Stroll to Galveston Ave

Bend

8% off
£3,558
for 7 nights, 1 home
£508 per night
includes taxes & fees
Modern Nordic Nest: Sauna & Stroll to Galveston Ave
New stainless appliances and fully stocked kitchen.
Property grounds
Morning coffee on the porch of this original 110-year-old Bend classic.
Terrace/patio
Exceptional
(94 reviews)

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

Bend

7% off
£1,376
for 7 nights, 1 home
£197 per night
includes taxes & fees
Historic 1917 cottage by the river, walkable to all of downtown Bend!
Living area
Summer on the river
View of river from back deck
Exterior
Exceptional
(193 reviews)

Riverfront Cottage -Near Drake Park, Walk to Town.

Bend

23% off
£1,054
for 7 nights, 1 home
£151 per night
includes taxes & fees
Riverfront Cottage -Near Drake Park, Walk to Town.
782E5D86-B7D6-4BE7-B9FE-B6A6A96EF4E2.jpeg
475278F8-70B1-4570-9F9F-26ECCC39D838.jpeg
471F239B-3233-4EFC-9C1F-EC0AC5853E2A.jpeg
Exterior
Exceptional
(44 reviews)

Downtown Craftsman with King Bed and Private Yard - Walk Everywhere

Bend

12% off
£1,698
for 7 nights, 1 home
£243 per night
includes taxes & fees
Downtown Craftsman with King Bed and Private Yard - Walk Everywhere
The kitchen is fully stocked down to the wine bottle opener.
The Bend Bungalow awaits! Set up high off street level is your quiet retreat.
Kitchen includes all you need to make a meal at home. Bon Apetite!
Dining
Exceptional
(138 reviews)

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

Bend

6% off
£956
for 7 nights, 1 home
£137 per night
includes taxes & fees
Bend Bungalow - a Walk in the Park to Downtown and River!
Interior
Exterior detail
Front of House
Dining
Exceptional
(165 reviews)

Bends Westside Kaleana's Garden Cottage

Bend

7% off
£1,393
for 7 nights, 1 home
£199 per night
includes taxes & fees
Bends Westside Kaleana's Garden Cottage
Fully remodeled kitchen with new cabinets, appliances and cork flooring
Westlake Cottage on a mid-summer day
washer/dryer hides away when not needed
smart TV with cable
Exceptional
(12 reviews)

Westlake Cottage - Great Weekly & Monthly Rates - walk Downtown

Bend

37% off
£1,023
for 7 nights, 1 home
£146 per night
includes taxes & fees
Westlake Cottage - Great Weekly & Monthly Rates - walk Downtown
Living area
Outdoor dining
Living area
Dining
Exceptional
(6 reviews)

Westside Bend: Walk to Eateries & Downtown!

Bend

7% off
£1,984
for 7 nights, 1 home
£283 per night
includes taxes & fees
Westside Bend: Walk to Eateries & Downtown!
  • 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, pools, gardens and more
  • More for less

    More space, more privacy, more amenities — more value

Frequently asked questions

How much does it cost to rent a holiday home in Old Bend?
Prices for holiday rentals 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 traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Old 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 Old Bend holiday house rentals?
You can find great discounts on house rentals in Old 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 Old Bend holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals 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 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 holiday rentals in Old Bend?
A long-stay holiday rental 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 travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
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.
How early should I book a Old Bend holiday rental?
Book your Old Bend holiday 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 holiday rental, the better the price. *Based on analysis of Vrbo booking and occupancy data for 2024 stays.
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.
Can I change or cancel my Old Bend home rental booking on Vrbo?
To find Old Bend holiday 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 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 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, Vrbo 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 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 Old Bend holiday 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, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way. Vrbo 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.
Can I plan a group trip on Vrbo?
Vrbo'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 favorites, and build the perfect itinerary together.

More holiday ideas