Southern Crossing holiday lettings

We found 500 holiday rentals — enter your dates for availability
Discover a selection of 65 homes and other holiday rentals in Southern Crossing that are perfect for your trip. Holiday homes offer the best amenities for you and your friends, family or even pets, such as a hot tub and a washer and dryer. No matter what you're looking for, you'll be sure to find a property to rent for everyone's needs, including accessible or non-smoking choices.

Holiday rentals with weekly discounts – Southern Crossing

Showing deals for:18 Dec - 25 Dec

Secluded, quiet, and peaceful luxury in a retreat like setting
While relaxing  on the cottage patio, guests are often enticed to see more
Tranquil setting - hidden gem in the heart of Bend
Complete kitchen with 4 burner stove, Microwave and Bosh dishwasher
Exceptional
(222 reviews)

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

Bend

6% off
£1,521
for 7 nights, 1 cottage
£217 per night
includes taxes & fees
Immaculate Downtown Cottage Retreat- EV charger. Walk downtown in 4 minutes
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
(95 reviews)

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

Bend

7% off
£1,401
for 7 nights, 1 home
£200 per night
includes taxes & fees
Historic 1917 cottage by the river, walkable to all of downtown Bend!
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

8% off
£4,968
for 7 nights, 1 home
£710 per night
includes taxes & fees
RIVERFRONT COTTAGE EPIC WALKABLE LOCATION ON RIVER
Master Bedroom with connecting master bathroom
Front
Entry View!
Living area
Exceptional
(159 reviews)

Spectacular Luxury Old Mill District Townhouse Walking Distance To River Walk

Bend

6% off
£1,325
for 7 nights, 1 home
£189 per night
includes taxes & fees
Spectacular Luxury Old Mill District Townhouse Walking Distance To River Walk
Private kitchen
Interior
Property grounds
Living area
Exceptional
(6 reviews)

Modern Nordic Nest: Sauna & Stroll to Galveston Ave

Bend

8% off
£4,931
for 7 nights, 1 home
£704 per night
includes taxes & fees
Modern Nordic Nest: Sauna & Stroll to Galveston Ave
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Exterior
Exceptional
(44 reviews)

Downtown Craftsman with King Bed and Private Yard - Walk Everywhere

Bend

12% off
£2,382
for 7 nights, 1 home
£340 per night
includes taxes & fees
Downtown Craftsman with King Bed and Private Yard - Walk Everywhere
Living room
Summer on the river
View of river from back deck
Exterior
Exceptional
(200 reviews)

Riverfront Cottage -Near Drake Park, Walk to Town.

Bend

23% off
£1,057
for 7 nights, 1 home
£151 per night
includes taxes & fees
Riverfront Cottage -Near Drake Park, Walk to Town.
Exterior detail
Living area
Terrace/patio
Interior
Exceptional
(7 reviews)

Dog friendly~Hot Tub~King Bed~Modern Construction

Bend

7% off
£2,516
for 7 nights, 1 home
£359 per night
includes taxes & fees
Dog friendly~Hot Tub~King Bed~Modern Construction
Front of House
Exterior detail
Interior
Outdoor dining
Exceptional
(170 reviews)

Bends Westside Kaleana's Garden Cottage

Bend

7% off
£1,385
for 7 nights, 1 home
£198 per night
includes taxes & fees
Bends Westside Kaleana's Garden Cottage
Living area
Private kitchen
Room
Dining
Exceptional
(11 reviews)

2 Bedrooms Home Retreat Old Mill Bend Near Downtown

Bend

8% off
£1,951
for 7 nights, 1 home
£279 per night
includes taxes & fees
2 Bedrooms Home Retreat Old Mill Bend Near Downtown
Living space
Gourmet Kitchen
Fuller Cottage
Welcome to Fuller Cottage
Exceptional
(51 reviews)

Bluebird Day - Fuller Cottage in Bend, OR: Charming 3-bedroom getaway with hot tub.

Bend

7% off
£2,248
for 7 nights, 1 home
£321 per night
includes taxes & fees
Bluebird Day - Fuller Cottage in Bend, OR: Charming 3-bedroom getaway with hot tub.
Cozy living room with door to patio/balcony
Dining
View downstairs from loft bedroom
View of living room from stairs to loft
Exceptional
(164 reviews)

Upgraded Mt.Bachelor Village Loft Condo + includes IKON pass holder offer

Bend

11% off
£1,329
for 7 nights, 1 apartment
£190 per night
includes taxes & fees
Upgraded Mt.Bachelor Village Loft Condo + includes IKON pass holder offer
  • 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 Southern Crossing?
Prices for holiday rentals in Southern Crossing 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 Southern Crossing 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 Southern Crossing holiday house rentals?
You can find great discounts on house rentals in Southern Crossing 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 Southern Crossing holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in Southern Crossing 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 Southern Crossing?
A long-stay holiday rental in Southern Crossing 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 Southern Crossing for a holiday rental?
The best time to visit Southern Crossing for a holiday rental is during the peak season from May to July, particularly in June. This vibrant month offers a delightful mix of warm weather and an array of outdoor activities for those seeking adventure. With temperatures typically ranging from the low teens to mid-twenties Celsius, June is superb for exploring the stunning landscapes, hiking trails, and recreational opportunities that Southern Crossing has to offer.As the region awakens with summer energy, visitors can enjoy activities like kayaking on the pristine waters or embarking on scenic hikes, all while soaking in the breathtaking natural beauty. The longer daylight hours mean more time to experience everything this picturesque area provides, whether it's a leisurely stroll or an exhilarating outdoor adventure.If you're looking for a more budget-friendly option, November can be a great time to visit. While it sees fewer tourists, the charm of the area remains intact, and you can enjoy a peaceful getaway amidst the stunning fall scenery. The crisp air and colourful foliage create a picturesque backdrop for serene walks and quiet reflection.Ultimately, your choice depends on whether you're drawn to the lively option of summer or the tranquillity of autumn.
How early should I book a Southern Crossing holiday rental?
Book your Southern Crossing 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 Southern Crossing, Oregon, United States of America?
Southern Crossing, Oregon, is a charming area with several attractions that highlight the region's natural beauty and outdoor activities. One of the main draws is the nearby Deschutes National Forest, where visitors can enjoy hiking, biking, and stunning views of the Cascade Mountains. The forest offers numerous trails suitable for various skill levels, making it a great spot for both casual walkers and avid hikers.Another popular attraction is the scenic Deschutes River, which is superb for fishing, rafting, and kayaking. The river's banks are lined with picturesque spots ideal for picnicking or simply enjoying the serene surroundings.For those interested in local culture, the town of Sisters is not far from Southern Crossing and features quaint shops, art galleries, and delightful cafes. The Sisters Outdoor Quilt Show, held annually, attracts visitors from all over and showcases the community's artistic spirit.
Can I change or cancel my Southern Crossing home rental booking on Vrbo?
To find Southern Crossing 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 Southern Crossing 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.

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