Photo by Hannah Martini

Old Bend holiday rentals

We found 349 holiday rentals — enter your dates for availability
Discover a selection of 65 homes, 10 apartments 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:13 Nov - 20 Nov

Home viewed from backyard with fire pit. Hot tub is not shown, on left
Beautifully appointed living spaces
Breakfast bar and kitchen
New Chef's kitchen with quartz counters, high-end applicances,
Excellent
(8 reviews)

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

Bend

7% off
S$6,947
for 7 nights, 1 home
S$992 per night
includes taxes & fees
Location! Historical District Downtown - Walk everywhere, new 4 Bedroom, 3 Bath
Living area
Just outside these windows is a wrap around deck to play on.
Living area
Private kitchen
Exceptional
(104 reviews)

Fantastic view of Bend with pickleball and basketball court

Bend

7% off
S$3,883
for 7 nights, 1 home
S$555 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
Secluded, quiet, and peaceful luxury in a retreat like setting
Exceptional
(219 reviews)

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

Bend

6% off
S$2,687
for 7 nights, 1 cottage
S$384 per night
includes taxes & fees
Immaculate Downtown Cottage Retreat- EV charger. Walk downtown in 4 minutes
Laundry Room: Full in-unit laundry facilities to handle all your outdoor gear.
Property grounds
New stainless appliances and fully stocked kitchen.
Terrace/patio
Exceptional
(94 reviews)

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

Bend

7% off
S$2,237
for 7 nights, 1 home
S$320 per night
includes taxes & fees
Historic 1917 cottage by the river, walkable to all of downtown Bend!
Living area
Interior
Property grounds
Private kitchen
Exceptional
(5 reviews)

Modern Nordic Nest: Sauna & Stroll to Galveston Ave

Bend

8% off
S$2,786
for 7 nights, 1 home
S$398 per night
includes taxes & fees
Modern Nordic Nest: Sauna & Stroll to Galveston Ave
View of river from back deck
Summer on the river
Exterior
Living room
Exceptional
(192 reviews)

Riverfront Cottage -Near Drake Park, Walk to Town.

Bend

23% off
S$1,753
for 7 nights, 1 home
S$250 per night
includes taxes & fees
Riverfront Cottage -Near Drake Park, Walk to Town.
471F239B-3233-4EFC-9C1F-EC0AC5853E2A.jpeg
475278F8-70B1-4570-9F9F-26ECCC39D838.jpeg
Exterior
95A36747-1443-4A2F-91A2-1421C79A0E72.jpeg
Exceptional
(44 reviews)

Downtown Craftsman with King Bed and Private Yard - Walk Everywhere

Bend

12% off
S$1,948
for 7 nights, 1 home
S$278 per night
includes taxes & fees
Downtown Craftsman with King Bed and Private Yard - Walk Everywhere
Steps down to the yard and water.
Easy access to the river from the back yard. Put in kayaks, SUP's or floats.
Desk for you to connect for laptop to our WiFi, if you have to work on vacation.
Love the granite we choose.
Exceptional
(198 reviews)

RIVERFRONT COTTAGE EPIC WALKABLE LOCATION ON RIVER

Bend

8% off
S$8,394
for 7 nights, 1 home
S$1,199 per night
includes taxes & fees
RIVERFRONT COTTAGE EPIC WALKABLE LOCATION ON RIVER
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.
Dining
Kitchen includes all you need to make a meal at home. Bon Apetite!
Exceptional
(138 reviews)

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

Bend

6% off
S$1,523
for 7 nights, 1 home
S$218 per night
includes taxes & fees
Bend Bungalow - a Walk in the Park to Downtown and River!
Interior
Exterior detail
Dining
Front of House
Exceptional
(164 reviews)

May special Bends Westside Kaleana's Garden Cottage

Bend

7% off
S$2,395
for 7 nights, 1 home
S$342 per night
includes taxes & fees
May special Bends Westside Kaleana's Garden Cottage
smart TV with cable
Westlake Cottage on a mid-summer day
Sunny cozy nook in south bedroom for quiet relaxation
Fully remodeled kitchen with new cabinets, appliances and cork flooring
Exceptional
(12 reviews)

Westlake Cottage - Great Weekly & Monthly Rates - walk Downtown

Bend

37% off
S$1,748
for 7 nights, 1 home
S$250 per night
includes taxes & fees
Westlake Cottage - Great Weekly & Monthly Rates - walk Downtown
Large kitchen with ample counter space allows group feasts.
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

5% off
S$1,556
for 7 nights, 1 home
S$222 per night
includes taxes & fees
Wren's Nest Updated Historic Home In The Heart Of Bend.
Room
Outdoor dining
Exterior
Living area
Exceptional
(6 reviews)

Westside Bend: Walk to Eateries & Downtown!

Bend

7% off
S$2,083
for 7 nights, 1 home
S$298 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, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Frequently asked questions

What is the most popular type of holiday rental accommodation in Old Bend?
Houses are the most popular type of holiday rental in Old Bend, according to our data. Even if you have something else in mind, Vrbo has properties in loads of sizes and shapes. Explore our options to find your perfect fit.
How much does it cost to rent a holiday rental in Old Bend?
Property type, length of stay and time of year are some of the things that can determine the price of a holiday home. Simply add your dates of travel to find your perfect escape. From quaint country cottages to plush villas, all Vrbo holiday rentals provide unbeatable value.
How much does it cost to rent a beach house in Old Bend?
Prices for beach houses in Old Bend may vary depending on the size and type of the property and when you plan to travel. Simply enter your travel dates into Vrbo and how many guests to view available options and prices. From there you can use the filters to refine your search results by ratings, amenities and more.
Are there pet-friendly holiday rentals in Old Bend?
You're in luck! There are. You can choose from 73 holiday rentals that cater to pets in Old Bend. Several of our pet-friendly holiday rentals even have a garden for your four-legged pal to run around in, complimentary treats, special dog beds and proximity to parks or green space. Apply the "Pets allowed" filter to find a pad that'll set tails wagging on Vrbo.
What are popular rental amenities in Old Bend?
A lake view, a beach view and nearby museums rank as the most popular rental amenities in Old Bend. Whether you're planning to travel solo, with a partner or a group of friends, Vrbo can help you find a holiday rental that matches your tastes with all the conveniences you're looking for.
Are there large group holiday rentals in Old Bend?
Yes, you can choose one of 29 holiday properties in Old Bend that can host five or more people. From family reunions to special occasions like birthday parties, these stays have ample space to gather with your favourite people.
Are there holiday rentals in Old Bend that welcome kids?
With 73 family-friendly holiday properties available in Old Bend, now is a fantastic time to introduce your kids to the pleasures of travel. Simply click on our "Properties good for families" filter to view stays that feature conveniences ideal for families on the move, like kitchens, yards, hot tubs and bunk beds.
What are the top attractions for families in Old Bend?
There are plenty of fun things to see and do with the family in Old Bend, such as:
  • High Desert Museum
  • Sun Mountain Fun Centre
  • Des Chutes Historical Museum
Are there one-bedroom holiday rentals in Old Bend?
Yes, you can choose from 19 one-bedroom rentals in Old Bend. Whether you're looking for a cosy cottage or a cabin, Vrbo's one-bedroom rentals are great if you don't require lots of room. One of the best parts about having your own place? You won't ever have to share your adventure with strangers.
Can I find two-bedroom holiday rentals in Old Bend?
You can pick from 33 two-bedroom holiday properties in Old Bend. Settle the kids into the second room or maybe fill it with a couple of your besties. There's space for whoever's fortunate enough to come along for the ride.
Are there holiday rentals with WiFi in Old Bend?
Take your pick of 28 holiday rentals with WiFi in Old Bend. If you'd like to disconnect from daily life on your holiday, but still want to be connected to the internet, these getaways are just what you need. Narrow your search by applying the WiFi filter on Vrbo.
How can I find holiday rentals with air conditioning in Old Bend?
You'll find 71 holiday rentals with air conditioning in Old Bend offering that cool, cool breeze and extra touch of comfort. Enter your travel dates and then make use of our filters to find properties with air conditioning.
How old do you have to be to rent a holiday rental in Old Bend?
The minimum age is usually 16, 18 or 21. It can change between properties on Vrbo, so look at the rules of your chosen Old Bend stay before booking.
How long can I rent a holiday rental in Old Bend for?
The amount of time you can book an Old Bend holiday home for is down to each property. Just put in your dates of travel to find options offering longer term stays. They feature all you require to make your extended break more comfortable like kitchens and air conditioning. Some Vrbo holiday rentals may also offer weekly or monthly discounts, so you can hang around longer for less.

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