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Featured Holiday Homes in Weston

Dog-friendly ski-in/ski-out retreat with views, fireplace, & washer/dryer

Dog-friendly ski-in/ski-out retreat with views, fireplace, & washer/dryer

Stratton
When you stay at this vacation home in Stratton, you'll be in the mountains, within a 10-minute walk of Stratton Mountain Resort and Green Mountain National ...
Dog-friendly ski-in/ski-out retreat with views, fireplace, & washer/dryer
Beautiful! 5 Beds-5 baths Home, Spectacular Views of Stratton, On Shuttle

Beautiful! 5 Beds-5 baths Home, Spectacular Views of Stratton, On Shuttle

Stratton
With a stay at this vacation home in Winhall, you'll be in the mountains, within a 10-minute drive of Stratton Mountain Resort and Green Mountain National ...
Beautiful! 5 Beds-5 baths Home, Spectacular Views of Stratton, On Shuttle
Fabulous Luxury Log Home, 6 BR 4BA, Pool Table, Hot Tub, BEST Location

Fabulous Luxury Log Home, 6 BR 4BA, Pool Table, Hot Tub, BEST Location

Ludlow
With a stay at this vacation home in Ludlow, you'll be on a lake, within a 5-minute drive of Okemo Mountain Resort and Sunshine Ski Lift.
Fabulous Luxury Log Home, 6 BR 4BA, Pool Table, Hot Tub, BEST Location
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Secluded home with game room, private hot tub, golf, river & mtn views, firepit

Secluded home with game room, private hot tub, golf, river & mtn views, firepit

Manchester
When you a stay at this vacation home in Manchester Center, you'll be next to a golf course, within a 5-minute walk of Green Mountain National Forest and Battenkill ...
Secluded home with game room, private hot tub, golf, river & mtn views, firepit
Idyllic Lakefront House Suited Two  Families

Idyllic Lakefront House Suited Two Families

Ludlow
With a stay at this vacation home in Ludlow, you'll be on the waterfront, within a 10-minute drive of Okemo Mountain Resort and Green Mountain Sugar House.
Idyllic Lakefront House Suited Two Families
Private, new home near Skyeship gondola with four fireplaces, washer/dryer, WiFi

Private, new home near Skyeship gondola with four fireplaces, washer/dryer, WiFi

Killington
With a stay at this vacation home in Killington, you'll be within a 15-minute drive of Killington Resort and Pico Mountain at Killington Ski Resort.
Private, new home near Skyeship gondola with four fireplaces, washer/dryer, WiFi
Dog-friendly cabin with forest setting, woodstove & deck - near Killington

Dog-friendly cabin with forest setting, woodstove & deck - near Killington

Plymouth
With a stay at this vacation home in Plymouth, you'll be within a 10-minute drive of Skyeship Express Gondola Stage I and Calvin Coolidge Homestead.
Dog-friendly cabin with forest setting, woodstove & deck - near Killington
Ski-On/Off - private sauna - right next to lift - 1GB WiFi - Renovated

Ski-On/Off - private sauna - right next to lift - 1GB WiFi - Renovated

Killington
When you stay at this vacation home in Killington, you'll be in the mountains, just steps from Killington Resort and 15 minutes by foot from Sunrise Village ...
Ski-On/Off - private sauna - right next to lift - 1GB WiFi - Renovated
☆ SKI ON & OFF! ☆ Spruce Glen D on Great Eastern Trail w/AC, Sauna, Fireplace

☆ SKI ON & OFF! ☆ Spruce Glen D on Great Eastern Trail w/AC, Sauna, Fireplace

Killington
When you stay at this vacation home in Killington, you'll be in the mountains, within a 15-minute drive of Killington Resort and Pico Mountain at Killington ...
☆ SKI ON & OFF! ☆ Spruce Glen D on Great Eastern Trail w/AC, Sauna, Fireplace
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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.

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
742 Holiday Homes
Lowest Price
AU$218
Highest Price
AU$778
Popular accommodation
Dog-friendly ski-in/ski-out retreat with views, fireplace, & washer/dryer, Beautiful! 5 Beds-5 baths Home, Spectacular Views of Stratton, On Shuttle, Fabulous Luxury Log Home, 6 BR 4BA, Pool Table, Hot Tub, BEST Location, Secluded home with game room, private hot tub, golf, river & mtn views, firepit, Idyllic Lakefront House Suited Two Families, Private, new home near Skyeship gondola with four fireplaces, washer/dryer, WiFi, Dog-friendly cabin with forest setting, woodstove & deck - near Killington, Ski-On/Off - private sauna - right next to lift - 1GB WiFi - Renovated, ☆ SKI ON & OFF! ☆ Spruce Glen D on Great Eastern Trail w/AC, Sauna, Fireplace

Top trending hotels in Weston

COHO Inn & Motor Lodge

COHO Inn & Motor Lodge

287 Vermont Rte 100, Weston, VT
The price is AU$385 per night from 11 Mar to 12 Mar
AU$385
includes taxes & fees
11 Mar - 12 Mar
When you stay at COHO Inn & Motor Lodge in Weston, you'll be near ski lifts, within a 5-minute drive of Mill Museum and Weston Playhouse.
COHO Inn & Motor Lodge
The Weston

The Weston

5 out of 5
630 Main St, Weston, VT
The price is AU$778 per night from 12 Mar to 13 Mar
AU$778
includes taxes & fees
12 Mar - 13 Mar
With a stay at The Weston in Weston, you'll be a 1-minute walk from West River and 5 minutes by foot from Mill Museum.
The Weston
Comfort Inn Rutland - Killington

Comfort Inn Rutland - Killington

2.5 out of 5
19 Allen St, Rutland, VT
Fully refundableReserve now, pay when you stay
The price is AU$218 per night from 13 Mar to 14 Mar
AU$218
includes taxes & fees
13 Mar - 14 Mar
With a stay at Comfort Inn Rutland - Killington in Rutland, you'll be 0.6 mi (1 km) from Rutland Regional Medical Center and 9.8 mi (15.7 km) from Pico Mountain ...
Comfort Inn Rutland - Killington
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Killington Mountain Lodge, Tapestry Collection by Hilton

Killington Mountain Lodge, Tapestry Collection by Hilton

3.5 out of 5
2617 Killington Rd, Killington, VT
Fully refundableReserve now, pay when you stay
The price is AU$259 per night from 1 Apr to 2 Apr
AU$259
includes taxes & fees
1 Apr - 2 Apr
With a stay at Killington Mountain Lodge, Tapestry Collection by Hilton in Killington, you'll be next to a golf course, just steps from Killington Resort and ...
Killington Mountain Lodge, Tapestry Collection by Hilton
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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.