Location

Dates

Guests

Vacation rentals in Stratton, Vermont, United States

Perfect Mountain Getaway

Perfect Mountain Getaway

Perfect Mountain Getaway

Perfect Mountain Getaway

Perfect Mountain Getaway

Perfect Mountain Getaway

3 bedrooms·2 baths

Winhall • Vermont

5(14 reviews)

$826.64 USD total for 3 nights

Oct 17 – 20, 2026

HYGGE HOUSE Green Mountain Villa - Sauna Hot Tub

HYGGE HOUSE Green Mountain Villa - Sauna Hot Tub

HYGGE HOUSE Green Mountain Villa - Sauna Hot Tub

HYGGE HOUSE Green Mountain Villa - Sauna Hot Tub

HYGGE HOUSE Green Mountain Villa - Sauna Hot Tub

HYGGE HOUSE Green Mountain Villa - Sauna Hot Tub

4 bedrooms·2 baths

Stratton • Vermont

5(171 reviews)

$1,280.29 USD total for 3 nights

Oct 19 – 22, 2026

The Lodge at Snow Mountain Farms | 5 BDR | 3 BA | 3,500 sqft

Lower level | Open concept game room, reading nook, bar, and living area

6-person hot tub - available all year

Living room with wood burning fireplace

Mt Snow/Stratton VT Getaway! w/Hot Tub + Game Room

5 bedrooms·3 baths

Wardsboro • Vermont

5(25 reviews)

$325 – $2,100/ night(excl. fees & taxes)

View of living room and dining room from kitchen.

Mount Snow Vista Cabin • Hot Tub & Sauna

Mount Snow Vista Cabin • Hot Tub & Sauna

Mount Snow Vista Cabin • Hot Tub & Sauna

Mount Snow Vista Cabin • Hot Tub & Sauna

Mount Snow Vista Cabin • Hot Tub & Sauna

5 bedrooms·3 baths

Dover • Vermont

$1,929.00 USD total for 3 nights

Oct 17 – 20, 2026

Mount Snow Vista Cabin • Hot Tub & Sauna

Mount Snow Vista Cabin • Hot Tub & Sauna

Mount Snow Vista Cabin • Hot Tub & Sauna

Mount Snow Vista Cabin • Hot Tub & Sauna

Mount Snow Vista Cabin • Hot Tub & Sauna

Mount Snow Vista Cabin • Hot Tub & Sauna

5 bedrooms·3 baths

Dover • Vermont

$1,233.75 USD total for 3 nights

Oct 17 – 20, 2026

Tranquil Treetop Retreat

Tranquil Treetop Retreat

Tranquil Treetop Retreat

Tranquil Treetop Retreat

Tranquil Treetop Retreat

4 bedrooms·4 baths

Winhall • Vermont

4.75(16 reviews)

$1,970.02 USD total for 3 nights

Oct 17 – 20, 2026

Stratton Slopeside Haven

Stratton Slopeside Haven

Stratton Slopeside Haven

Stratton Slopeside Haven

Stratton Slopeside Haven

Stratton Slopeside Haven

2 bedrooms·3 baths

Winhall • Vermont

4.86(7 reviews)

$1,005.65 USD total for 3 nights

Oct 17 – 20, 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)

$1,192.32 USD total for 3 nights

Oct 17 – 20, 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)

$1,383.65 USD total for 3 nights

Oct 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

$1,883.68 USD total for 3 nights

Oct 17 – 20, 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)

$1,536.31 USD total for 3 nights

Oct 25 – 28, 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)

$1,847.55 USD total for 3 nights

Oct 18 – 21, 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 17 – 20, 2026

The Bears Den

4 bedrooms·3 baths

Winhall • Vermont

4.5(2 reviews)

$1,400.66 USD total for 3 nights

Oct 17 – 20, 2026

Snowdrift

4 bedrooms·3 baths

Winhall • Vermont

4.71(7 reviews)

$1,539.52 USD total for 3 nights

Oct 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)

Snowfall Retreat

Snowfall Retreat

Snowfall Retreat

Snowfall Retreat

Snowfall Retreat

Snowfall Retreat

3 bedrooms·3 baths

Winhall • Vermont

$1,180.44 USD total for 3 nights

Oct 18 – 21, 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)

$1,357.42 USD total for 3 nights

Oct 17 – 20, 2026

New stainless steel appliances

Sauna with Green Mountain View’s

3 bedrooms·3 baths

Jamaica • Vermont

A cozy cabin-style home with a wooden deck, nestled among lush greenery, featuring Adirondack chairs on a stone-lined lawn.

A cozy living room with a loft, featuring a leather sectional, woven chairs, and a rustic staircase leading to an upper level.

A cozy backyard fire pit area with four wooden Adirondack chairs arranged around a circular stone pit. Surrounded by lush green grass and dense trees, it offers a serene outdoor retreat.

A cozy bedroom featuring a black metal bunk bed with a full-size lower and twin upper. The wooden-paneled walls and carpeted floor add warmth, while a telescope by the window invites stargazing.

A rustic wooden deck extends from the house, surrounded by lush greenery. Three wicker chairs with cushions offer a peaceful spot to relax and enjoy the natural surroundings.

6BD 3BA - Mount Snow VT - Ski-Back Trail - Shuttle

6 bedrooms·3 baths

Dover • Vermont

$2,297.00 USD total for 3 nights

Oct 17 – 20, 2026

2BD 1BA - Mount Snow VT - Ski-Back Trail - Shuttle

2BD 1BA - Mount Snow VT - Ski-Back Trail - Shuttle

2BD 1BA - Mount Snow VT - Ski-Back Trail - Shuttle

As you step inside you'll be assured that you chose the right place!

2BD 1BA - Mount Snow VT - Ski-Back Trail - Shuttle

2BD 1BA - Mount Snow VT - Ski-Back Trail - Shuttle

2 bedrooms·1 bath

Dover • Vermont

$738.80 USD total for 3 nights

Oct 17 – 20, 2026

Main living area with large couch and 4 lounge chairs, fireplace and TV

4BD 2BA - Mount Snow VT - Ski-Back Trail - Shuttle

Chalet style home on private lot, wrap around deck

4BD 2BA - Mount Snow VT - Ski-Back Trail - Shuttle

4BD 2BA - Mount Snow VT - Ski-Back Trail - Shuttle

4BD 2BA - Mount Snow VT - Ski-Back Trail - Shuttle

4 bedrooms·2 baths

Dover • Vermont

$1,032.60 USD total for 3 nights

Oct 17 – 20, 2026

Drop Point Cabin 15minutes to Stratton

Drop Point Cabin 15minutes to Stratton

4 bedrooms·3 baths

Jamaica • Vermont

$1,049.02 USD total for 3 nights

Oct 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)