The Bears Den

4 bedrooms·3 baths
Winhall • Vermont
4.5(2 reviews)

$1,504.50 USD total for 3 nights

Nov 18 – 21, 2026

Tranquil Treetop Retreat

4 bedrooms·4 baths
Winhall • Vermont
4.75(16 reviews)

$1,688.34 USD total for 3 nights

Nov 18 – 21, 2026

Stratton Slopeside Retreat

2 bedrooms·2 baths
Winhall • Vermont
5(3 reviews)

$1,321.15 USD total for 3 nights

Nov 18 – 21, 2026

Stratton Slopeside Haven

2 bedrooms·3 baths
Winhall • Vermont
4.86(7 reviews)

$976.93 USD total for 3 nights

Nov 18 – 21, 2026

Ski Lodge Hideaway: 5 minutes to Stratton mountain

4 bedrooms·4 baths
Winhall • Vermont
5(6 reviews)

$1,249.33 USD total for 3 nights

Nov 18 – 21, 2026

Snowfall Retreat

3 bedrooms·3 baths
Winhall • Vermont

$1,168.09 USD total for 3 nights

Nov 18 – 21, 2026

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

3 bedrooms·2 baths
Winhall • Vermont
4.75(8 reviews)

$1,155.11 USD total for 3 nights

Nov 18 – 21, 2026

Village Watch Lux Loft

4 bedrooms·3 baths
Winhall • Vermont

$2,435.05 USD total for 3 nights

Nov 22 – 25, 2026

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

2 bedrooms·2 baths
Winhall • Vermont
5(89 reviews)

$1,327.75 USD total for 3 nights

Nov 24 – 27, 2026

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

3 bedrooms·3 baths
Winhall • Vermont
4.8(5 reviews)

$1,418.96 USD total for 3 nights

Nov 18 – 21, 2026

Stunning 4,000 sq. ft. Stratton Chalet

5 bedrooms·1 bath
Winhall • Vermont
3.33(3 reviews)

$8,826.74 USD total for 3 nights

Nov 18 – 21, 2026

Stratton Loft with Pool

4 bedrooms·2 baths
Winhall • Vermont

Burnt Hill Chalet

3 bedrooms·2 baths
Winhall • Vermont

$3,640.00 USD total for 5 nights

Nov 18 – 23, 2026

Hot Tub Chalet on Magic Mountain

5 bedrooms·2½ baths
Londonderry • Vermont

Magic Circle home-Private Hot Tub, Fire pit+ more!

3 bedrooms·2 baths
Londonderry • Vermont

Casita Bacon

4 bedrooms·4 baths
Winhall • Vermont

$1,280.24 USD total for 3 nights

Nov 18 – 21, 2026

Cozy Chalet 12 Min to Stratton & 7 Min to Bromley

4 bedrooms·2 baths
Winhall • Vermont
5(10 reviews)

$902.00 USD total for 3 nights

Nov 18 – 21, 2026