Location

Dates

Guests

Vacation rentals in Jamaica, Vermont, United States

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)

New stainless steel appliances

Sauna with Green Mountain View’s

3 bedrooms·3 baths

Jamaica • 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

$2,053.91 USD $1,737.29 USD total for 3 nights

Sep 7 – 10, 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)

$299 – $1,981/ night(excl. fees & taxes)

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)

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)

$1,156.87 USD total for 3 nights

Sep 7 – 10, 2026

Snowdrift

4 bedrooms·3 baths

Winhall • Vermont

4.71(7 reviews)

$1,600.29 USD total for 3 nights

Sep 7 – 10, 2026

The Bears Den

4 bedrooms·3 baths

Winhall • Vermont

4.5(2 reviews)

$1,400.66 USD total for 3 nights

Sep 7 – 10, 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

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)

$1,576.01 USD total for 3 nights

Sep 7 – 10, 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)

$934.65 USD total for 3 nights

Sep 7 – 10, 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)

$871.96 USD total for 3 nights

Sep 7 – 10, 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)

$1,197.69 USD total for 3 nights

Sep 7 – 10, 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

$1,596.84 USD total for 3 nights

Sep 7 – 10, 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

Sep 12 – 15, 2026

Front of the house

Cubbies and boot warmers

Spacious mud room

Space for all your gear

Upstairs living room

Stratton Vacay Chalet

3 bedrooms·2 baths

Winhall • Vermont

$3,892.00 USD total for 5 nights

Sep 7 – 12, 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)

$1,785.05 USD total for 3 nights

Sep 7 – 10, 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

Sep 7 – 10, 2026

Free cancellation

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)

$679.77 USD total for 3 nights

Sep 7 – 10, 2026

The Tower House

The Tower House

The Tower House

The Tower House

The Tower House

The Tower House

4 bedrooms·2 baths

Londonderry • Vermont

4.89(9 reviews)

Londonderry Links

Londonderry Links

Londonderry Links

Londonderry Links

Londonderry Links

Londonderry Links

3 bedrooms·2 baths

Londonderry • Vermont

4.88(25 reviews)

$200/ night(excl. fees & taxes)

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)

$1,309.67 USD total for 3 nights

Sep 8 – 11, 2026

Welcome to our chalet!

We have 2 pellet stoves!

Comfort is our priority!

Hot Tub Chalet on Magic Mountain

5 bedrooms·2½ baths

Londonderry • Vermont

Casita Bacon

4 bedrooms·4 baths

Winhall • Vermont

$1,132.06 USD total for 3 nights

Sep 7 – 10, 2026