Book Holiday Homes in Weston
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Featured Holiday Homes in Weston

Private, Dog-Friendly Estate with Free WiFi, Fireplaces, Washer/Dryer, & Pond

8 min to Stratton, 6 min to golf, 15 min to Manchester. Pet friendly!

By Manchester, VT-Circa 1840 Hand Hewn Barn on private pond close to skiing.

Okemo Mountain Lodging

Lake front house about 1 mile from Okemo's Jackson Gore Base Lodge

Creekside Camp. NO CLEANING FEE. Relax in the Hot Tub Creekside - Vermont Style

Manchester, Mt Equinox Views, Hot Tub, Horse-show,golf,skiing,hiking,fishing

Heated Saltwater Pool: Riverfront Home in Ludlow

5 BR Duplex with Hot Tub & Firepit 1 minute from Killington Resort!
Weston 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 Weston vacation homes are the perfect way for you to wing it.
Holiday houses in Weston 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 Weston 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 Weston adventures, obvs.
If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Weston 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 Weston 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.
Weston Holiday Homes essential information
Accommodation | 926 Holiday Homes |
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Popular accommodation | Private, Dog-Friendly Estate with Free WiFi, Fireplaces, Washer/Dryer, & Pond, 8 min to Stratton, 6 min to golf, 15 min to Manchester. Pet friendly!, By Manchester, VT-Circa 1840 Hand Hewn Barn on private pond close to skiing., Okemo Mountain Lodging, Lake front house about 1 mile from Okemo's Jackson Gore Base Lodge, Creekside Camp. NO CLEANING FEE. Relax in the Hot Tub Creekside - Vermont Style, Manchester, Mt Equinox Views, Hot Tub, Horse-show,golf,skiing,hiking,fishing, Heated Saltwater Pool: Riverfront Home in Ludlow, 5 BR Duplex with Hot Tub & Firepit 1 minute from Killington Resort! |
More accommodations in Weston
Top trending hotels in Weston

NEW Charming ski retreat w/heated plunge pool & endless views in peaceful Weston

The Weston

Cozy Creekside Chalet centrally located near 4 ski resorts

Comfort Inn Rutland - Killington
More ways to explore Weston
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^Subject to availability and chosen travel dates.