Book Holiday Homes in Sisters

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Featured Holiday Homes in Sisters

Historic Belle Millhouse in Bend, OR.  Walk to Downtown.vrbo

Historic Belle Millhouse in Bend, OR. Walk to Downtown.vrbo

Bend
With a stay at this vacation home, you'll be centrally located in Bend, within a 5-minute drive of Old Mill District and Hayden Homes Amphitheater.
Historic Belle Millhouse in Bend, OR. Walk to Downtown.vrbo
Adorable Bend townhome with ideal location, kitchenette & central AC

Adorable Bend townhome with ideal location, kitchenette & central AC

Bend
With a stay at this vacation home in Bend (Century West), you'll be a 5-minute drive from Hayden Homes Amphitheater and 6 minutes from Old Mill District.
Adorable Bend townhome with ideal location, kitchenette & central AC
Sensational Designer's Townhouse in the heart of Eagle Crest.

Sensational Designer's Townhouse in the heart of Eagle Crest.

Redmond
Located in Redmond, this vacation home is within a 10-minute drive of Deschutes River and Eagle Ridge Sports Center and Spa.
Sensational Designer's Townhouse in the heart of Eagle Crest.
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Close to Downtown, Newly Renovated, Walk to Shopping, Dining, Drinks

Close to Downtown, Newly Renovated, Walk to Shopping, Dining, Drinks

Bend
With a stay at this vacation home in Bend (Larkspur), you'll be within a 5-minute drive of Old Mill District and Hayden Homes Amphitheater.
Close to Downtown, Newly Renovated, Walk to Shopping, Dining, Drinks
Amazing West Side * 2 King Suites * Walk Everywhere  * 8 Person Hot Tub

Amazing West Side * 2 King Suites * Walk Everywhere * 8 Person Hot Tub

Bend
With a stay at this vacation home, you'll be centrally located in Bend, within a 5-minute drive of Hayden Homes Amphitheater and Old Mill District.
Amazing West Side * 2 King Suites * Walk Everywhere * 8 Person Hot Tub
Deck + HotTub | Community Golf Course, 2 Pools, Sport Courts | Forest Ridge Loop

Deck + HotTub | Community Golf Course, 2 Pools, Sport Courts | Forest Ridge Loop

2.5 out of 5
Redmond
When you stay at this vacation home in Redmond, you'll be on a river, within a 5-minute drive of Eagle Ridge Sports Center and Spa and Eagle Crest Golf ...
Deck + HotTub | Community Golf Course, 2 Pools, Sport Courts | Forest Ridge Loop
Central Oregon Escape - Mountain Views - Hot Tub - AC and Fireplace

Central Oregon Escape - Mountain Views - Hot Tub - AC and Fireplace

Terrebonne
Located in Terrebonne, this vacation home is in a rural location, within a 15-minute drive of Deschutes River and Crooked River Ranch Golf Course.
Central Oregon Escape - Mountain Views - Hot Tub - AC and Fireplace
McKenzie Bridge River's Edge Retreat, a cozy cabin on over two acres

McKenzie Bridge River's Edge Retreat, a cozy cabin on over two acres

McKenzie Bridge
With a stay at this vacation home in Blue River, you'll be just steps from Willamette National Forest and McKenzie River.
McKenzie Bridge River's Edge Retreat, a cozy cabin on over two acres
Heart of Bend-Walkable, Ping Pong, Billards

Heart of Bend-Walkable, Ping Pong, Billards

Bend
With a stay at this vacation home, you'll be centrally located in Bend, a 5-minute drive from Old Mill District and 6 minutes from Hayden Homes ...
Heart of Bend-Walkable, Ping Pong, Billards
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Sisters Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Sisters vacation homes are the perfect way for you to wing it.

Holiday houses in Sisters let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Sisters in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Sisters adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Sisters with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Sisters vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Sisters Holiday Homes essential information

Accommodation
1332 Holiday Homes
Lowest Price
Highest Price
Popular accommodation
Historic Belle Millhouse in Bend, OR. Walk to Downtown.vrbo, Adorable Bend townhome with ideal location, kitchenette & central AC, Sensational Designer's Townhouse in the heart of Eagle Crest. , Close to Downtown, Newly Renovated, Walk to Shopping, Dining, Drinks, Amazing West Side * 2 King Suites * Walk Everywhere * 8 Person Hot Tub, Deck + HotTub | Community Golf Course, 2 Pools, Sport Courts | Forest Ridge Loop, Central Oregon Escape - Mountain Views - Hot Tub - AC and Fireplace, McKenzie Bridge River's Edge Retreat, a cozy cabin on over two acres, Heart of Bend-Walkable, Ping Pong, Billards

Top trending hotels in Sisters

GrandStay Hotel & Suites

GrandStay Hotel & Suites

3 out of 5
1026 W Rail Way, Sisters, OR
Fully refundableReserve now, pay when you stay
With a stay at GrandStay Hotel & Suites in Sisters, you'll be 24.1 mi (38.8 km) from Old Mill District and 24.4 mi (39.3 km) from Deschutes Brewery.
GrandStay Hotel & Suites
Sisters Inn And Suites

Sisters Inn And Suites

2.5 out of 5
605 North Arrowleaf Trail, P.O. Box 938, Sisters, OR
With a stay at Sisters Inn And Suites in Sisters, you'll be 21.3 mi (34.2 km) from Hoodoo Ski Area and 21.4 mi (34.4 km) from Deschutes County Fairgrounds Expo ...
Sisters Inn And Suites
FivePine Lodge & Spa

FivePine Lodge & Spa

4 out of 5
1021 Desperado Trail, Sisters, OR
With a stay at FivePine Lodge & Spa in Sisters, you'll be a 2-minute walk from Shibui Spa and 11 minutes by foot from Peterson Ridge Trail.
FivePine Lodge & Spa
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Best Western Ponderosa Lodge

Best Western Ponderosa Lodge

2.5 out of 5
790 W Barclay Drive, Sisters, OR
Fully refundableReserve now, pay when you stay
When you stay at Best Western Ponderosa Lodge in Sisters, you'll be next to a golf course, within a 5-minute drive of Cork Cellars and Makin' It Local.
Best Western Ponderosa Lodge
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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^Subject to availability and chosen travel dates.