Location

Dates

Guests

Vacation rentals in Whitingham, Vermont, United States

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)

$1,095.64 USD total for 3 nights

Nov 17 – 20, 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

$2,453.64 USD total for 3 nights

Nov 22 – 25, 2026

Private Cabin Retreat | near Stratton & Mt. Snow

Private Cabin Retreat | near Stratton & Mt. Snow

4 bedrooms·3 baths

Jamaica • Vermont

$1,036.04 USD total for 3 nights

Nov 17 – 20, 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)

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)

$1,307.44 USD total for 3 nights

Nov 17 – 20, 2026

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)

$1,327.75 USD total for 3 nights

Nov 24 – 27, 2026

Stunning 4,000 sq. ft. Stratton Chalet

Stunning 4,000 sq. ft. Stratton Chalet

Stunning 4,000 sq. ft. Stratton Chalet

Stunning 4,000 sq. ft. Stratton Chalet

Stunning 4,000 sq. ft. Stratton Chalet

Stunning 4,000 sq. ft. Stratton Chalet

5 bedrooms·1 bath

Winhall • Vermont

3.33(3 reviews)

$8,825.61 USD total for 3 nights

Nov 17 – 20, 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

3 bedrooms·3 baths

Winhall • Vermont

4.71(7 reviews)

$1,216.00 USD total for 3 nights

Nov 17 – 20, 2026

The Bears Den

4 bedrooms·3 baths

Winhall • Vermont

4.5(2 reviews)

$1,504.50 USD total for 3 nights

Nov 17 – 20, 2026

Snowfall Retreat

Snowfall Retreat

Snowfall Retreat

Snowfall Retreat

Snowfall Retreat

Snowfall Retreat

3 bedrooms·3 baths

Winhall • Vermont

$1,054.10 USD total for 3 nights

Nov 17 – 20, 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)

$1,249.33 USD total for 3 nights

Nov 17 – 20, 2026

The Deming House

The Deming House

The Deming House

The Deming House

The Deming House

The Deming House

3 bedrooms·4 baths

Arlington • Vermont

4(1 review)

$1,671.64 USD total for 3 nights

Nov 17 – 20, 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

Winter Wonderland

Hot tub and Sauna.. and silence

Try 30 minutes in the sauna...after full day of skiing

Living Room Retreat: Sunlit space with vaulted ceilings and stylish decor for perfect relaxation!

Delight in the hottub when its cool outside

Stratton Ski Haus

4 bedrooms·2½ baths

Jamaica • Vermont

$1,842.45 USD $1,715.44 USD total for 3 nights

Nov 17 – 20, 2026

The Azimuth

5 bedrooms·2 baths

Sunderland • Vermont

$1,480.96 USD total for 3 nights

Nov 20 – 23, 2026

HUGE private Mansion! 15 bedroom, 12 bath sleep 34

HUGE private Mansion! 15 bedroom, 12 bath sleep 34

HUGE private Mansion! 15 bedroom, 12 bath sleep 34

HUGE private Mansion! 15 bedroom, 12 bath sleep 34

HUGE private Mansion! 15 bedroom, 12 bath sleep 34

HUGE private Mansion! 15 bedroom, 12 bath sleep 34

15 bedrooms·1 bath

Manchester • Vermont

5(17 reviews)

$10,983.60 USD total for 3 nights

Nov 17 – 20, 2026

The Riverside Treehouse

The Riverside Treehouse

The Riverside Treehouse

The Riverside Treehouse

The Riverside Treehouse

The Riverside Treehouse

3 bedrooms·2 baths

Arlington • Vermont

5(4 reviews)

$944.42 USD total for 3 nights

Nov 18 – 21, 2026

Hillside Getaway

Hillside Getaway

Hillside Getaway

Hillside Getaway

Hillside Getaway

Hillside Getaway

3 bedrooms·2 baths

Sandgate • Vermont

5(17 reviews)

$1,480.90 USD total for 3 nights

Nov 17 – 20, 2026