Location

Dates

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Vacation rentals in Wardsboro, Vermont, United States

New stainless steel appliances

Sauna with Green Mountain View’s

3 bedrooms·3 baths

Jamaica • Vermont

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)

$1,417.02 USD total for 3 nights

Oct 30 – Nov 2, 2026

Private Cabin Retreat | near Stratton & Mt. Snow

Private Cabin Retreat | near Stratton & Mt. Snow

4 bedrooms·3 baths

Jamaica • Vermont

$1,005.36 USD total for 3 nights

Oct 30 – Nov 2, 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)

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)

$1,191.02 USD total for 3 nights

Oct 30 – Nov 2, 2026

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)

$660.81 USD total for 3 nights

Oct 30 – Nov 2, 2026

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

$1,980.50 USD total for 3 nights

Oct 30 – Nov 2, 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

$1,285.25 USD total for 3 nights

Oct 30 – Nov 2, 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)

$1,037.56 USD total for 3 nights

Oct 30 – Nov 2, 2026

The Bears Den

4 bedrooms·3 baths

Winhall • Vermont

4.5(2 reviews)

$1,400.66 USD total for 3 nights

Oct 30 – Nov 2, 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)

$1,593.36 USD total for 3 nights

Oct 30 – Nov 2, 2026

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

$2,088.36 USD $1,620.81 USD total for 3 nights

Oct 31 – Nov 3, 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)

$1,163.15 USD total for 3 nights

Oct 30 – Nov 2, 2026

Snowfall Retreat

Snowfall Retreat

Snowfall Retreat

Snowfall Retreat

Snowfall Retreat

Snowfall Retreat

3 bedrooms·3 baths

Winhall • Vermont

$1,079.03 USD total for 3 nights

Oct 30 – Nov 2, 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)

$859.80 USD total for 3 nights

Oct 30 – Nov 2, 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 30 – Nov 2, 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)

$1,068.86 USD total for 3 nights

Oct 30 – Nov 2, 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

$1,440.06 USD total for 3 nights

Oct 30 – Nov 2, 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)

$2,525.55 USD total for 3 nights

Oct 30 – Nov 2, 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)

$1,265.06 USD total for 3 nights

Oct 30 – Nov 2, 2026

Table is made from reclaimed barn wood and great for a large dinner.

Steps to Farm Rd Estate | Historic 2BR w/ AC! image 2

Relax with some art or watch a great movie in the Great Room on the comfy sofa.

Reclaimed barnwood table

The large bedroom on the first floor was transformed from the art gallery.

Historic 1827 House | 2BR • Walkable location

2 bedrooms·1 bath

Dover • Vermont

5(61 reviews)

$1,920.18 USD total for 3 nights

Mar 19 – 22, 2027

Open comfy space with wide floor boards and spiral access to the large loft.

Relax by the gas fireplace on second floor

The 1827 House has easy access from RT 100 where you can walk to fine restaurants and venture to close by Wilmington, Manchester and lots of trails!

Comfortable and romantic Queen Victorian room

Loft Queen beds

Historic 1827 House | 3BR • AC • Upstairs

3 bedrooms·2 baths

Dover • Vermont

5(28 reviews)

$969.85 USD total for 3 nights

Oct 30 – Nov 2, 2026

The Great Room was once the village general store and Post Office. Imagine the conversations over the years in this room.

Easy access on RT100.

Upstairs living area. Views of mount snow ski area from north side windows.

Futon in Loft sleeps two. Great for overflow skiers.

Relax by the gas fireplace on second floor after a day of skiing. Mini Split for quiet & comfortable AC in the summer and heat in the winter.

Historic 1827 House | 5BR • AC • Walkable

5 bedrooms·3 baths

Dover • Vermont

5(20 reviews)

$500 – $750/ night(excl. fees & taxes)