Southern Crossing holiday lettings
We found 506 holiday rentals — enter your dates for availability
Discover a selection of 72 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:27 Nov - 4 Dec

Exceptional
(221 reviews)
Immaculate Downtown Cottage Retreat- EV charger. Walk downtown in 4 minutes
Bend
£1,438
for 7 nights, 1 cottage
£205 per night
includes taxes & fees

Exceptional
(198 reviews)
RIVERFRONT COTTAGE EPIC WALKABLE LOCATION ON RIVER
Bend
£4,963
for 7 nights, 1 home
£709 per night
includes taxes & fees

Exceptional
(94 reviews)
Historic 1917 cottage by the river, walkable to all of downtown Bend!
Bend
£1,389
for 7 nights, 1 home
£198 per night
includes taxes & fees

Exceptional
(138 reviews)
Bend Bungalow - a Walk in the Park to Downtown and River!
Bend
£907
for 7 nights, 1 home
£130 per night
includes taxes & fees

Exceptional
(14 reviews)
Home Centrally Located Near Old Mill Downtown
Bend
£1,298
for 7 nights, 1 home
£185 per night
includes taxes & fees

Exceptional
(5 reviews)
Modern Nordic Nest: Sauna & Stroll to Galveston Ave
Bend
£2,585
for 7 nights, 1 home
£369 per night
includes taxes & fees

Exceptional
(195 reviews)
Riverfront Cottage -Near Drake Park, Walk to Town.
Bend
£1,107
for 7 nights, 1 home
£158 per night
includes taxes & fees

Exceptional
(44 reviews)
Downtown Craftsman with King Bed and Private Yard - Walk Everywhere
Bend
£1,523
for 7 nights, 1 home
£218 per night
includes taxes & fees

Exceptional
(7 reviews)
Dog friendly~Hot Tub~King Bed~Modern Construction
Bend
£1,719
for 7 nights, 1 home
£246 per night
includes taxes & fees

Exceptional
(11 reviews)
2 Bedrooms Home Retreat Old Mill Bend Near Downtown
Bend
£1,177
for 7 nights, 1 home
£168 per night
includes taxes & fees

Exceptional
(157 reviews)
Spectacular Luxury Old Mill District Townhouse Walking Distance To River Walk
Bend
£1,338
for 7 nights, 1 home
£191 per night
includes taxes & fees

Exceptional
(163 reviews)
Upgraded Mt.Bachelor Village Loft Condo + includes IKON pass holder offer
Bend
£1,119
for 7 nights, 1 apartment
£160 per night
includes taxes & fees

Exceptional
(166 reviews)
Bends Westside Kaleana's Garden Cottage
Bend
£1,377
for 7 nights, 1 home
£197 per night
includes taxes & fees

Exceptional
(38 reviews)
Top 5% - Finnish Sauna - Near Old Mill - No Pets - Fully Remodeled - Quiet
Bend
£1,143
for 7 nights, 1 home
£163 per night
includes taxes & fees

Exceptional
(63 reviews)
Executive suite in Mount Bachelor Village - great for a couple
Bend
£739
for 7 nights, 1 apartment
£106 per night
includes taxes & fees
Find spaces that suit your style
House
Condo/Apartment
Cabin
Cottage
Villa
Chalet
Find properties near top attractions in Southern Crossing
Find the best place to stay - Southern Crossing

Home Centrally Located Near Old Mill Downtown
Sleeps 4 · 2 bedrooms · 2+ bathrooms

Luxurious Townhome Steps from the Deschutes River with Riverviews, Deck & BBQ
Sleeps 6 · 3 bedrooms · 3 bathrooms

Vantage Point - Hot Tub, Updated, Outdoor Spaces, Steps to Old Mill and River
Sleeps 8 · 3 bedrooms · 3 bathrooms

New! Old Mill Lookout–Mountain Views, Fireplace, Dog Friendly
Sleeps 8 · 3 bedrooms · 2+ bathrooms

Beautiful end unit home with big horizon views!
Sleeps 6 · 3 bedrooms · 4 bathrooms

Old Mill Townhome Steps from River and Trails, Shops, Restaurants, Fireplace, A/C, Dog Friendly.
Sleeps 8 · 3 bedrooms · 3 bathrooms
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.
More holiday ideas
- Century West Holiday Rentals
- West Hills Holiday Rentals
- Mountain View Holiday Rentals
- Bend River Promenade Holiday Rentals
- Awbrey Butte Holiday Rentals
- Deschutes River Woods Holiday Rentals
- Widgi Creek Golf Club Holiday Rentals
- Deschutes County Holiday Rentals
- Tetherow Holiday Rentals
- Broken Top Holiday Rentals
- Orchard District Holiday Rentals
- Bend Factory Stores Holiday Rentals
- Old Bend Holiday Rentals
- Southeast Bend Holiday Rentals
- Old Farm District Holiday Rentals
- Pilot Butte State Park Holiday Rentals
- Tetherow Golf Club Holiday Rentals
- Mt. Bachelor Village Holiday Rentals
- Deschutes River Holiday Rentals
- Deschutes Landing Holiday Rentals
- Bend Holiday Rentals
- Old Mill District Holiday Rentals
- River West Holiday Rentals
- Blockbuster Holiday Rentals
- Sagewood Holiday Rentals
- Southwest Bend Holiday Rentals
- Larkspur Holiday Rentals
- Boyd Acres Holiday Rentals
- Central Oregon Community College Holiday Rentals
- Hayden Homes Amphitheater Holiday Rentals
- Longstay Hotels in Black Butte Ranch
- Rentals with pool near Todd Lake
- Apartments in Hood River
- Houses in Hood River
- Cabins in Hood River
- Longstay Hotels in Hood River
- Oceanfront rentals near Cove Palisades State Park
- Castles in Ankeny National Wildlife Refuge
- Ski-In/Ski-Out rentals near Ankeny National Wildlife Refuge
- Longstay Hotels in Waldport
- Apartments in Deschutes County
- Longstay Hotels in Salem
- Rv and caravan rentals in Fernhill Wetlands Park
- Ski-In/Ski-Out rentals near Fernhill Wetlands Park
- Pet-Friendly rentals in Sunriver
- Houses in Sunriver
- Lake rentals in Sunriver
- Lodges in Sunriver
- Rentals with pool in Sunriver
- Resorts in Sunriver
- Rentals with pool near Larch Mountain
- Rentals with pool near Collier Memorial State Park
- Family rentals near Oaks Bottom Wildlife Refuge
- Apartments in Mount Hood National Forest
- Bed and breakfasts in Mount Hood National Forest
- Resorts in Crescent Lake
- Bed and breakfasts in Steel Visitor Center
- Family rentals near Steel Visitor Center
- Pet-Friendly rentals in Eugene
- Cabins in Eugene
- Rv and caravan rentals in Ochoco Wayside State Park
- Bed and breakfasts in White River Falls State Park
- Guest houses in White River Falls State Park
- Ski-In/Ski-Out rentals near Tom McCall Preserve
- Resorts in Central Oregon Coast
- Family rentals near Willamette National Forest
- Cabins in Oregon
- Longstay Hotels in Oregon
- Cabins in Joseph H Stewart County Park
- Cabins in Yachats
- Apartments in Terrebonne
- Longstay Hotels in Portland (and vicinity)
- Rv and caravan rentals in La Pine State Park
- Resorts in Bend
- Longstay Hotels in Bend
- Villas in Starvation Creek State Park
- Rv and caravan rentals in Willamette Shore Trolley
- Apartments in Beaverton
- Cottages in Beaverton
- Pet-Friendly rentals in Beaverton
- Houses in Beaverton
- Longstay Hotels in Camp Sherman
- Rv and caravan rentals in Shepperd's Dell State Natural Area
- Bed and breakfasts in Jackson Bottom Wetlands Preserve
- Castles in Jackson Bottom Wetlands Preserve
- Longstay Hotels in Oregon City
- Pet-Friendly rentals near Mt Bachelor
- Cabins in Multnomah Falls
- Hotels in Lake Billy Chinook
- Resorts in Klamath Falls
- Rv and caravan rentals in Mount Hood Railroad
- Ski-In/Ski-Out rentals near Mount Hood Railroad
- Rv and caravan rentals in Detroit Lake
- Pet-Friendly rentals near Silver Falls State Park
- Resorts in Crater Lake National Park
- Longstay Hotels in Newberg
- Cabins in Terwilliger Hot Springs
- Oceanfront rentals near Town and Country Bowling Lanes
- Guest houses in Lava River Cave
- Pet-Friendly rentals near Lava River Cave


