Book Holiday Homes in Orleans
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Featured Holiday Homes in Orleans

Colorful Farmhouse just minutes from East Burke, Kingdom Trails and Burke Mtn

Lux 5BR/4BA V125 Ski I/O, 18-hole Championship Golf, Water Park, pet friendly

Cozy house 30 min to Stowe, 30 min to Smugglers Notch, 30 min to Jay Peak

Fish, Hike & Ski: Spacious Family Escape in Eden

Lakehouse, waterfront, dock, kayaks, wifi, grill, outdoor dining, ping-pong, w/d

Wonderful VT Get Away, Great Family Fun, with WiFi.

Dog-friendly, lakeside home w/wood-burning fireplace/private dock/deck/free WiFi

Brand New, Private Home with Nordic Hot Tub- Just .5mi to Jay Peak Ski Resort

Perfect Location. Ski in Ski out on Village Chair
Orleans 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 Orleans vacation homes are the perfect way for you to wing it.
Holiday houses in Orleans 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 Orleans 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 Orleans adventures, obvs.
If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Orleans 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 Orleans 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.
Orleans Holiday Homes essential information
Accommodation | 153 Holiday Homes |
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Highest Price | |
Popular accommodation | Colorful Farmhouse just minutes from East Burke, Kingdom Trails and Burke Mtn, Lux 5BR/4BA V125 Ski I/O, 18-hole Championship Golf, Water Park, pet friendly , Cozy house 30 min to Stowe, 30 min to Smugglers Notch, 30 min to Jay Peak, Fish, Hike & Ski: Spacious Family Escape in Eden, Lakehouse, waterfront, dock, kayaks, wifi, grill, outdoor dining, ping-pong, w/d, Wonderful VT Get Away, Great Family Fun, with WiFi., Dog-friendly, lakeside home w/wood-burning fireplace/private dock/deck/free WiFi, Brand New, Private Home with Nordic Hot Tub- Just .5mi to Jay Peak Ski Resort, Perfect Location. Ski in Ski out on Village Chair |
Top Locations for Holiday Homes in Orleans
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Lake Willoughby Views and access. Boat Dock and Beach Wood fired hot tub

Beautifully Renovated Classic Vermont Lake View Cottage

Lakeside Isbell Cottage and Isbellita Guest Cottage

Lake Willoughby Direct Waterfront
More ways to explore Orleans
Top picks
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^Subject to availability and chosen travel dates.