Location

Dates

Guests

Vacation rentals in Wilmington, Vermont, United States

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

$1,376.86 USD total for 3 nights

Oct 31 – Nov 3, 2026

Private Cabin Retreat | near Stratton & Mt. Snow

Private Cabin Retreat | near Stratton & Mt. Snow

4 bedrooms·3 baths

Jamaica • Vermont

$1,054.92 USD total for 3 nights

Oct 31 – Nov 3, 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)

$1,162.00 USD total for 3 nights

Oct 31 – Nov 3, 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)

$2,186.55 USD total for 3 nights

Oct 31 – Nov 3, 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)

$8,826.74 USD total for 3 nights

Oct 31 – Nov 3, 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)

$984.09 USD total for 3 nights

Oct 31 – Nov 3, 2026

The Bears Den

4 bedrooms·3 baths

Winhall • Vermont

4.5(2 reviews)

$1,400.66 USD total for 3 nights

Oct 31 – Nov 3, 2026

Snowfall Retreat

Snowfall Retreat

Snowfall Retreat

Snowfall Retreat

Snowfall Retreat

Snowfall Retreat

3 bedrooms·3 baths

Winhall • Vermont

$1,017.19 USD total for 3 nights

Oct 31 – Nov 3, 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)

$1,150.79 USD total for 3 nights

Oct 31 – Nov 3, 2026

Front yard and house

Guard rails have been added both sides of stairs since this picture was taken.

Looking up toward loft area with partial view of kitchen lower right. Note the spiral staircase.

Cozy converted barn on secluded 6.5 acres

3 bedrooms·1 bath

Shaftsbury • Vermont

5(390 reviews)

$927.80 USD $833.72 USD total for 3 nights

Oct 31 – Nov 3, 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

$2,017.80 USD $1,571.41 USD total for 3 nights

Oct 31 – Nov 3, 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 total for 5 nights

Oct 31 – Nov 5, 2026

Casita Bacon

4 bedrooms·4 baths

Winhall • Vermont

$1,006.87 USD total for 3 nights

Oct 31 – Nov 3, 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)

$1,155.35 USD total for 3 nights

Nov 13 – 16, 2026

The Azimuth

5 bedrooms·2 baths

Sunderland • Vermont

$1,170.95 USD total for 3 nights

Nov 1 – 4, 2026

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)

$902.00 USD total for 3 nights

Oct 31 – Nov 3, 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

Oct 31 – Nov 3, 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 total for 3 nights

Oct 31 – Nov 3, 2026

Shadow Peak Chalet

Shadow Peak Chalet

Shadow Peak Chalet

Shadow Peak Chalet

Shadow Peak Chalet

Shadow Peak Chalet

4 bedrooms·2 baths

Manchester • Vermont

$959.47 USD total for 3 nights

Nov 1 – 4, 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)

$845.58 USD total for 3 nights

Nov 2 – 5, 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)

$898.19 USD total for 3 nights

Nov 2 – 5, 2026