Book Holiday Homes in Weston

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Featured Holiday Homes in Weston

Classic ski home with hot tub, washer/dryer, mountain views, & cable

Classic ski home with hot tub, washer/dryer, mountain views, & cable

Ludlow VT
With a stay at this vacation home, you'll be centrally located in Ludlow, within a 5-minute drive of Okemo Mountain Resort and Red Lot.
Opens in a new windowClassic ski home with hot tub, washer/dryer, mountain views, & cable
The Dorothy-10 minutes from Okemo- freshly renovated

The Dorothy-10 minutes from Okemo- freshly renovated

Cavendish VT
With a stay at this vacation home in Cavendish, you'll be within a 15-minute drive of Okemo Mountain Resort and Phineas Gage Memorial.
Opens in a new windowThe Dorothy-10 minutes from Okemo- freshly renovated
Idyllic Lakefront House Suited Two  Families

Idyllic Lakefront House Suited Two Families

Ludlow VT
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.
Opens in a new windowIdyllic Lakefront House Suited Two Families
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Cool Barn renovation with views. 5 mins to hikes, restaurants, fishing and more!

Cool Barn renovation with views. 5 mins to hikes, restaurants, fishing and more!

Manchester VT
When you stay at this vacation home in Manchester, you'll be in the mountains, within a 15-minute walk of Museum of Creative Process and Golf Club at ...
Opens in a new windowCool Barn renovation with views. 5 mins to hikes, restaurants, fishing and more!
3 Levels w/ Magnificent Mountain Views, 5 Mins to Stratton Base, Sauna, Firepit

3 Levels w/ Magnificent Mountain Views, 5 Mins to Stratton Base, Sauna, Firepit

Winhall VT
With a stay at this vacation home in Bondville, you'll be in the mountains, within a 10-minute drive of Stratton Mountain Resort and Winhall River.
Opens in a new window3 Levels w/ Magnificent Mountain Views, 5 Mins to Stratton Base, Sauna, Firepit
Historic Renovated Barn at Boorn Brook Farm - Manchester Vermont

Historic Renovated Barn at Boorn Brook Farm - Manchester Vermont

Manchester Center VT
With a stay at this vacation home in Manchester Center, you'll be on a river, just steps from Green Mountain National Forest and a 3-minute drive from Lye Brook ...
Opens in a new windowHistoric Renovated Barn at Boorn Brook Farm - Manchester Vermont
Starry Skies: 7min to SkiStratton+PikesFalls+DogOK

Starry Skies: 7min to SkiStratton+PikesFalls+DogOK

Jamaica VT
With a stay at this vacation home in Jamaica (Pikes Falls), you'll be within a 15-minute drive of Stratton Mountain Resort and Solstice Ski Lift.
Opens in a new windowStarry Skies: 7min to SkiStratton+PikesFalls+DogOK
Fantastic 6-bedroom house in Mendon Vermont - Killington / Pico

Fantastic 6-bedroom house in Mendon Vermont - Killington / Pico

Rutland VT
With a stay at this vacation home in Rutland, you'll be within a 5-minute drive of Green Mountain National Forest and Green Mountain Rock Climbing Center.
Opens in a new windowFantastic 6-bedroom house in Mendon Vermont - Killington / Pico
Sleeps 30!! 2 Cabins, 10 Bedrooms, 3 Kitchens, Hot Tub, Fireplaces, Game Rooms

Sleeps 30!! 2 Cabins, 10 Bedrooms, 3 Kitchens, Hot Tub, Fireplaces, Game Rooms

Wardsboro VT
With a stay at this vacation home in Wardsboro, you'll be next to a golf course, within a 15-minute drive of Mount Snow and Wardsboro Public Library.
Opens in a new windowSleeps 30!! 2 Cabins, 10 Bedrooms, 3 Kitchens, Hot Tub, Fireplaces, Game Rooms
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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
793 Holiday Homes
Lowest Price
AU$207
Highest Price
AU$278
Popular accommodation
Classic ski home with hot tub, washer/dryer, mountain views, & cable, The Dorothy-10 minutes from Okemo- freshly renovated, Idyllic Lakefront House Suited Two Families, Cool Barn renovation with views. 5 mins to hikes, restaurants, fishing and more!, 3 Levels w/ Magnificent Mountain Views, 5 Mins to Stratton Base, Sauna, Firepit, Historic Renovated Barn at Boorn Brook Farm - Manchester Vermont, Starry Skies: 7min to SkiStratton+PikesFalls+DogOK, Fantastic 6-bedroom house in Mendon Vermont - Killington / Pico, Sleeps 30!! 2 Cabins, 10 Bedrooms, 3 Kitchens, Hot Tub, Fireplaces, Game Rooms

Top trending hotels in Weston

COHO Inn & Motor Lodge

COHO Inn & Motor Lodge

2 out of 5
287 Vermont Rte 100 Weston VT
The price is AU$269 per night from 5 Apr to 6 Apr
AU$269
5 Apr - 6 Apr
includes taxes & fees
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.
Opens in a new windowCOHO Inn & Motor Lodge
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$207 per night from 22 Apr to 23 Apr
AU$207
22 Apr - 23 Apr
includes taxes & fees
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 ...
Opens in a new windowKillington Mountain Lodge, Tapestry Collection by Hilton
Pointe at Castle Hill Resort

Pointe at Castle Hill Resort

3.5 out of 5
2940 State Route 103 Cavendish VT
The price is AU$278 per night from 5 Apr to 6 Apr
AU$278
5 Apr - 6 Apr
includes taxes & fees
With a stay at Pointe at Castle Hill Resort in Cavendish, you'll be near ski lifts, within a 10-minute drive of Okemo Mountain Resort and Fletcher Farm School ...
Opens in a new windowPointe at Castle Hill Resort
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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$215 per night from 23 Apr to 24 Apr
AU$215
23 Apr - 24 Apr
includes taxes & fees
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 ...
Opens in a new windowComfort Inn Rutland - Killington
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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.