Location

Dates

Guests

Vacation rentals in Cavendish, Vermont, United States

Renovated 2BR on Bromley | Fall Foliage & Hiking

Renovated 2BR on Bromley | Fall Foliage & Hiking

Renovated 2BR on Bromley | Fall Foliage & Hiking

Renovated 2BR on Bromley | Fall Foliage & Hiking

Renovated 2BR on Bromley | Fall Foliage & Hiking

Renovated 2BR on Bromley | Fall Foliage & Hiking

2 bedrooms·1 bath

Peru • Vermont

4.61(28 reviews)

$ 839,45 USD totaal voor 3 nachten

24–27 okt 2026

Cozy Bromley Retreat

Cozy Bromley Retreat

Cozy Bromley Retreat

Cozy Bromley Retreat

Cozy Bromley Retreat

Cozy Bromley Retreat

1 bedroom·1 bath

Peru • Vermont

5(1 review)

$ 644,57 USD totaal voor 3 nachten

26–29 okt 2026

Wrap Around Deck

Killington Grandview House

7 bedrooms·6½ baths

Mendon • Vermont

4.86(7 reviews)

$ 4.576,50 USD totaal voor 3 nachten

25–28 okt 2026

The Little Matterhorn

The Little Matterhorn

The Little Matterhorn

The Little Matterhorn

The Little Matterhorn

The Little Matterhorn

3 bedrooms·2 baths

Winhall • Vermont

4.87(30 reviews)

$ 820,05 USD totaal voor 3 nachten

24–27 okt 2026

The fireplace anchors a generous seating area for conversation, movies, or a quiet evening at home.

Enjoy the hot tub in a wood-paneled room just steps from the living area and yard.

Pull up an Adirondack chair for an evening around the backyard fire pit.

Wood cabinetry, generous counters, and full-size appliances provide a practical place to cook for the group.

Share meals beside the soaring windows, then move easily into the adjoining living room.

The Maple Leaf | Private Indoor Hot Tub

3 bedrooms·2 baths

Killington • Vermont

4.8(5 reviews)

$ 1.579,72 USD totaal voor 3 nachten

24–27 okt 2026

Front of the house

Cubbies and boot warmers

Spacious mud room

Space for all your gear

Upstairs living room

Burnt Hill Chalet

3 bedrooms·2 baths

Winhall • Vermont

$ 3.640,00 USD totaal voor 5 nachten

24–29 okt 2026

The Ultimate Vermont Getaway

The Ultimate Vermont Getaway

The Ultimate Vermont Getaway

The Ultimate Vermont Getaway

The Ultimate Vermont Getaway

The Ultimate Vermont Getaway

4 bedrooms·3 baths

Rutland • Vermont

5(10 reviews)

$ 1.179,27 USD totaal voor 3 nachten

4–7 nov 2026

Outdoor pool is open now!

Welcome to the loft

Walk out balcony

Enough space fore the whole crew

Stratton Loft with Pool

4 bedrooms·2 baths

Winhall • Vermont

Cozy Chalet 12 Min to Stratton & 7 Min to Bromley

Cozy Chalet 12 Min to Stratton & 7 Min to Bromley

Cozy Chalet 12 Min to Stratton & 7 Min to Bromley

Cozy Chalet 12 Min to Stratton & 7 Min to Bromley

Cozy Chalet 12 Min to Stratton & 7 Min to Bromley

Cozy Chalet 12 Min to Stratton & 7 Min to Bromley

4 bedrooms·2 baths

Winhall • Vermont

5(10 reviews)

$ 906,00 USD totaal voor 3 nachten

24–27 okt 2026

Stratton Chalet 5 minute drive to Bromley 10 to Stratton

Stratton Chalet 5 minute drive to Bromley 10 to Stratton

Stratton Chalet 5 minute drive to Bromley 10 to Stratton

Stratton Chalet 5 minute drive to Bromley 10 to Stratton

Stratton Chalet 5 minute drive to Bromley 10 to Stratton

Stratton Chalet 5 minute drive to Bromley 10 to Stratton

4 bedrooms·5 baths

Winhall • Vermont

5(8 reviews)

$ 1.106,13 USD totaal voor 3 nachten

24–27 okt 2026

Drop Point Cabin

Drop Point Cabin

Drop Point Cabin

Drop Point Cabin

Drop Point Cabin

Drop Point Cabin

4 bedrooms·3 baths

Jamaica • Vermont

4.72(25 reviews)

Drop Point Cabin 15minutes to Stratton

Drop Point Cabin 15minutes to Stratton

4 bedrooms·3 baths

Jamaica • Vermont

$ 1.021,88 USD totaal voor 3 nachten

26–29 okt 2026

Casita Bacon

4 bedrooms·4 baths

Winhall • Vermont

$ 1.045,76 USD totaal voor 3 nachten

25–28 okt 2026

Ski Lodge Hideaway: 5 minutes to Stratton mountain

Ski Lodge Hideaway: 5 minutes to Stratton mountain

Ski Lodge Hideaway: 5 minutes to Stratton mountain

Ski Lodge Hideaway: 5 minutes to Stratton mountain

Ski Lodge Hideaway: 5 minutes to Stratton mountain

Ski Lodge Hideaway: 5 minutes to Stratton mountain

4 bedrooms·4 baths

Winhall • Vermont

5(6 reviews)

$ 1.196,98 USD totaal voor 3 nachten

24–27 okt 2026

Stratton Hollow House

Stratton Hollow House

Stratton Hollow House

Stratton Hollow House

Stratton Hollow House

Stratton Hollow House

4 bedrooms·2 baths

Jamaica • Vermont

5(1 review)

Snowdrift

4 bedrooms·3 baths

Winhall • Vermont

4.71(7 reviews)

$ 1.281,86 USD totaal voor 3 nachten

24–27 okt 2026

The Bears Den

4 bedrooms·3 baths

Winhall • Vermont

4.5(2 reviews)

$ 1.400,66 USD totaal voor 3 nachten

24–27 okt 2026

Snowfall Retreat

Snowfall Retreat

Snowfall Retreat

Snowfall Retreat

Snowfall Retreat

Snowfall Retreat

3 bedrooms·3 baths

Winhall • Vermont

$ 1.280,60 USD totaal voor 3 nachten

24–27 okt 2026

New stainless steel appliances

Sauna with Green Mountain View’s

3 bedrooms·3 baths

Jamaica • Vermont

The warm and inviting living room has direct access to the patio with a view of the pond and fountain.
The gas fireplace operates with the simple turn of a timer switch.

Heated year-round, the beautiful pool, hot tubs and sauna are just steps from Rising Bear Lodge.

Beautiful architecture and design inside and out.

Luxury Condo*Walk to Ski Lifts*Hot Tub*Pool*Sauna!

Luxury Condo*Walk to Ski Lifts*Hot Tub*Pool*Sauna!

Luxury CondoWalk to Ski LiftsHot TubPoolSauna!

2 bedrooms·2 baths

Winhall • Vermont

5(89 reviews)

$ 1.847,55 USD totaal voor 3 nachten

26–29 okt 2026

Hearthstone Retreat - Luxurious 3BR/3BA Condo in Stratton, VT

Hearthstone Retreat - Luxurious 3BR/3BA Condo in Stratton, VT

Hearthstone Retreat - Luxurious 3BR/3BA Condo in Stratton, VT

Hearthstone Retreat - Luxurious 3BR/3BA Condo in Stratton, VT

Hearthstone Retreat - Luxurious 3BR/3BA Condo in Stratton, VT

Hearthstone Retreat - Luxurious 3BR/3BA Condo in Stratton, VT

3 bedrooms·3 baths

Winhall • Vermont

4.8(5 reviews)

$ 1.704,51 USD totaal voor 3 nachten

25–28 okt 2026

Stratton Slopeside Retreat

Stratton Slopeside Retreat

Stratton Slopeside Retreat

Stratton Slopeside Retreat

Stratton Slopeside Retreat

Stratton Slopeside Retreat

2 bedrooms·2 baths

Winhall • Vermont

5(3 reviews)

$ 1.104,81 USD totaal voor 3 nachten

24–27 okt 2026

Village Watch Wonderland Ski on Ski off + Steps to Stratton Village

Village Watch Wonderland Ski on Ski off + Steps to Stratton Village

Village Watch Wonderland Ski on Ski off + Steps to Stratton Village

Village Watch Wonderland Ski on Ski off + Steps to Stratton Village

Village Watch Wonderland Ski on Ski off + Steps to Stratton Village

Village Watch Wonderland Ski on Ski off + Steps to Stratton Village

3 bedrooms·2 baths

Winhall • Vermont

4.75(8 reviews)

$ 1.191,61 USD totaal voor 3 nachten

24–27 okt 2026

Village Watch Lux Loft

Village Watch Lux Loft

Village Watch Lux Loft

Village Watch Lux Loft

Village Watch Lux Loft

Village Watch Lux Loft

4 bedrooms·3 baths

Winhall • Vermont

$ 1.630,88 USD totaal voor 3 nachten

24–27 okt 2026