Front View of The Farmhouse - The Second Story is All Yours
Open Space & Relaxation. The Ultimate Social Distancing Escape!
Classic Vermont - Historic Renovated Dairy Farm (No Cows Anymore)
Lazy Afternoon in Paradise
Fresh Air with Wifi. (If You're into that Sort of Thing....)

2 Bdrm, Upper Level, Okemo, 25 Acre Mtn Playground

2 bedrooms·1 bath
Cavendish • Vermont
5(13 reviews)

$1,375.00 USD total for 5 nights

Sep 7 – 12, 2026

Exterior
Property grounds
Aerial view
Living area
Miscellaneous

Summer fun on lake - great for 2 families or 3 couples - newly remodeled

4 bedrooms·2 baths
Windsor County • Vermont

$4,000.00 USD total for 5 nights

Sep 13 – 18, 2026

Lake Rescue Chalet-6-BR Lake & Ski House w/Hot Tub
Lake Rescue Chalet-6-BR Lake & Ski House w/Hot Tub
Lake Rescue Chalet-6-BR Lake & Ski House w/Hot Tub
Lake Rescue Chalet-6-BR Lake & Ski House w/Hot Tub
Lake Rescue Chalet-6-BR Lake & Ski House w/Hot Tub

Lake Rescue Chalet-6-BR Lake & Ski House w/Hot Tub

6 bedrooms·2 baths
Ludlow • Vermont
5(107 reviews)
$550 – $650/ night(excl. fees & taxes)
Mount Holly Lake & Ski Hideaway
Mount Holly Lake & Ski Hideaway
Mount Holly Lake & Ski Hideaway
Fall in Mount Holly
Mount Holly Lake & Ski Hideaway

Mount Holly Lake & Ski Hideaway

4 bedrooms·2 baths
Mount Holly • Vermont
5(37 reviews)
$299/ night(excl. fees & taxes)
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)
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
Snowdrift
Snowdrift
Snowdrift
Snowdrift

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
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

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

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
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

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 view of the front of the home with the wrap around deck!
This is the view of the rear of the home
the access ramp
entry to the home at the rear.
Enter via the mudroom and please remove your shoes!

Manchester Santuary II

4 bedrooms·4½ baths
Manchester • Vermont
5(1 review)

$1,925.50 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

Manchester Sanctuary escape to Vermont!
Manchester Sanctuary escape to Vermont!
Manchester Sanctuary escape to Vermont!
Manchester Sanctuary escape to Vermont!
Manchester Sanctuary escape to Vermont!

Manchester Sanctuary escape to Vermont!

3 bedrooms·3½ baths
Manchester • Vermont
5(2 reviews)

$1,756.00 USD total for 3 nights

Sep 30 – Oct 3, 2026

Free cancellation
NirvanaSanctuaryHouse~Fire Place~Okemo Killington
NirvanaSanctuaryHouse~Fire Place~Okemo Killington
Hot Tub Area Undercover!
Hot Springs Hot Tub ~ seats 4
King Master Bedroom

NirvanaSanctuaryHouse~Fire Place~Okemo Killington

2 bedrooms·3 baths
Plymouth • Vermont
5(31 reviews)

$1,695.00 USD total for 3 nights

Sep 8 – 11, 2026

We are currently updating our photos. Front lawn view
Twilight
Vermont Cottage Amherst Lake & Sanctuary
Vermont Cottage Amherst Lake & Sanctuary
Vermont Cottage Amherst Lake & Sanctuary

Vermont Cottage Amherst Lake & Sanctuary

6 bedrooms·4 baths
Plymouth • Vermont
4.98(90 reviews)

$6,582.00 USD total for 6 nights

Sep 15 – 21, 2026

Twilight ~ CURRENTLY UPDATING PICTURES ~ STAY TUNED!
Historic Vermont Lake Cottage~Hot Tub~Dogs~Okemo
Historic Vermont Lake Cottage~Hot Tub~Dogs~Okemo
Historic Vermont Lake Cottage~Hot Tub~Dogs~Okemo
Historic Vermont Lake Cottage~Hot Tub~Dogs~Okemo

Historic Vermont Lake Cottage~Hot Tub~Dogs~Okemo

4 bedrooms·3 baths
Plymouth • Vermont
5(55 reviews)

$2,294.20 USD total for 3 nights

Sep 7 – 10, 2026

The front porch at dusk
Winter firepit
Cute Cabin! Plymouth, Vermont.
Cute Cabin! Plymouth, Vermont.
Cute Cabin! Plymouth, Vermont.

Cute Cabin! Plymouth, Vermont.

3 bedrooms·3 baths
Plymouth • Vermont
5(52 reviews)

$2,031.00 USD total for 3 nights

Sep 8 – 11, 2026

Get-Away Cabin in Plymouth, Vermont.
Aerial view of Lake Amherst
Large screened-in porch overlooking the lake.
Get-Away Cabin in Plymouth, Vermont.
Hot Tub

Get-Away Cabin in Plymouth, Vermont.

1 bedroom·2 baths
Plymouth • Vermont
5(34 reviews)

$1,107.00 USD total for 3 nights

Sep 7 – 10, 2026

1930s-era cottage.
Private outdoor hot tub under cover.
Outdoor fire pit
Primary bedroom with king bed. Featuring a Puffy mattress, fine linens, plenty of pillows, and a down comforter.
The living room opens up to a larger screened-in porch. Dining also on the porch. It features a wood-burning fireplace for cooler times. It will be all set to light and we provide plenty of wood.

Twinkle Cottage ~HotTub~FirePit~Fireplace~Dogs

1 bedroom·2 baths
Plymouth • Vermont

$1,191.00 USD total for 3 nights

Sep 7 – 10, 2026