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)
The Bears Den
The Bears Den
The Bears Den
The Bears Den
The Bears Den

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

View of the house from the driveway. On over an acre, surrounded by trees.
View of the house as you head up the driveway. House sits on an acre+ lot.
Kitchen with space for two at the counter.
Upgraded kitchen with quartz counters and stainless steel appliances.
Dining room & kitchen combo opens to the living room too for easy conversation.

The Crooked House

3 bedrooms·2½ baths
Stockbridge • Vermont
5(100 reviews)

$971.00 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 Condo*Walk to Ski Lifts*Hot Tub*Pool*Sauna!

2 bedrooms·2 baths
Winhall • Vermont
5(89 reviews)

$2,186.55 USD total for 3 nights

Sep 12 – 15, 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
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

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)
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

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

Tranquil Treetop Retreat
image-4
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

House facade from driveway
Fully equipped kitchen with refrigerator, dishwasher, microwave and gas range
Bathroom with shower and copper sink.
Combo washer/dryer
Breakfast island separates kitchen from living area.

Custom-built Tiny House on forested lot near Quechee

1 bedroom·1 bath
Hartland • Vermont
4.87(71 reviews)
$209 – $309/ night(excl. fees & taxes)
Specials Ski-in Ski-Out Cozy Mountainside Condo
Specials Ski-in Ski-Out Cozy Mountainside Condo
Specials Ski-in Ski-Out Cozy Mountainside Condo
Specials Ski-in Ski-Out Cozy Mountainside Condo
Specials Ski-in Ski-Out Cozy Mountainside Condo

Specials Ski-in Ski-Out Cozy Mountainside Condo

4 bedrooms·2½ baths
Hartford • Vermont

$738.00 USD total for 3 nights

Sep 7 – 10, 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

Sep 7 – 10, 2026

Green River Escape
Green River Escape
Green River Escape
Green River Escape
Green River Escape

Green River Escape

1 bedroom·1 bath
Sandgate • Vermont

$637.28 USD total for 3 nights

Sep 7 – 10, 2026

The Azimuth
The Azimuth
The Azimuth
The Azimuth
The Azimuth

The Azimuth

4 bedrooms·2 baths
Sunderland • Vermont

$1,170.95 USD total for 3 nights

Sep 7 – 10, 2026

Front of the home from the two-car off street parking pad. Walkway lights up at night for later check-ins.
Cute, Renovated Home on River, Walk to Downtown
Cute, Renovated Home on River, Walk to Downtown
Spacious upstairs full bath
Cute, Renovated Home on River, Walk to Downtown

Cute, Renovated Home on River, Walk to Downtown

3 bedrooms·1½ baths
Brandon • Vermont
4.8(51 reviews)

$788.00 USD total for 3 nights

Sep 14 – 17, 2026

Hillside Getaway
Hillside Getaway
Hillside Getaway
Hillside Getaway
Hillside Getaway

Hillside Getaway

3 bedrooms·2 baths
Sandgate • Vermont
5(17 reviews)

$1,412.39 USD total for 3 nights

Sep 7 – 10, 2026