Open concept for larger groups
Seasonal Fire Pit with Grill in our yard (not open during winter)
Family room with giant 65" Smart VT
Tic Tac Toe anyone?
Seating area for meals

Trailside Chalet

5 bedrooms·2½ baths
Washington County • Vermont
4.93(85 reviews)

1097,47 $ USD total por 3 noches

25–28 oct 2026

Winter Wonderland! Great Okemo rental.
Lazy Afternoon in Paradise
Open Space & Relaxation. The Ultimate Social Distancing Escape!
Fresh Air with Wifi. (If You're into that Sort of Thing....)
Classic Vermont - Historic Renovated Dairy Farm (No Cows Anymore)

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

2 bedrooms·1 bath
Cavendish • Vermont
5(27 reviews)

1374,89 $ USD total por 5 noches

23–28 oct 2026

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)

1374,89 $ USD total por 5 noches

23–28 oct 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

4000,00 $ USD total por 5 noches

23–28 oct 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/ noche(sin comisiones ni impuestos)
NirvanaSanctuary~HotTub~FirePit~Dogs~Okemo + ~2BR
NirvanaSanctuary~HotTub~FirePit~Dogs~Okemo + ~2BR
Hot Tub Area Undercover!
Hot Springs Hot Tub ~ seats 4
King Master Bedroom

NirvanaSanctuary~HotTub~FirePit~Dogs~Okemo + ~2BR

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

1593,00 $ USD total por 3 noches

26–29 oct 2026

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

Vermont Cottage Amherst Lake

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

6582,00 $ USD total por 6 noches

23–29 oct 2026

Twilight ~ CURRENTLY UPDATING PICTURES ~ STAY TUNED!
Vermont Cottage Amherst Lake & Sanctuary
Vermont Cottage Amherst Lake & Sanctuary
Vermont Cottage Amherst Lake & Sanctuary
Vermont Cottage Amherst Lake & Sanctuary

Vermont Cottage Amherst Lake & Sanctuary

4 bedrooms·3 baths
Plymouth • Vermont
5(70 reviews)

2294,20 $ USD total por 3 noches

26–29 oct 2026

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

Cute Vermont Cabin! Plymouth, Vermont.

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

1919,00 $ USD total por 3 noches

26–29 oct 2026

Poppy's Cabin~Dogs~HotTub~FirePlace&Pit~Okemo~1BR
Aerial view of Lake Amherst
Large screened-in porch overlooking the lake.
Poppy's Cabin~Dogs~HotTub~FirePlace&Pit~Okemo~1BR
Hot Tub

Poppy's Cabin~Dogs~HotTub~FirePlace&Pit~Okemo~1BR

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

1107,00 $ USD total por 3 noches

26–29 oct 2026

1930s-era cottage.
Hot tub open to the outside and under cover.
Primary bedroom with king bed. Featuring a Puffy mattress, fine linens, plenty of pillows, and a down comforter.
View of the lake from this bedroom
Large screened-in front porch overlooking the lake. Listen to water fowl and peepers at night.

Amherst Guest Cottage ~ One Bedroom

1 bedroom·2 baths
Plymouth • Vermont

1191,00 $ USD total por 3 noches

1–4 nov 2026

Carriage House
Carriage House
Carriage House
Carriage House
Carriage House

Carriage House

2 bedrooms·2 baths
Mount Holly • Vermont

927,00 $ USD total por 3 noches

23–26 oct 2026

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/ noche(sin comisiones ni impuestos)
Spacious living room
Fully stocked kithcen
Queen bedroom with natural light
Double bedroom
Welcome to our cozy home!

Rural Chester Farmhouse

3 bedrooms·2 baths
Chester • Vermont
Enjoy a movie and some theater style popcorn in our living room and open kitchen
Jacuzzi Hot Tub
The kitchen is stocked with everything you need to wow your family and friends with your culinary abilities, or just keep the drinks cold and go out, all Weston has to offer is mere footsteps
Challenge each other to a game of basketball, arcade classic Mortal Kombat 3 or one of many others - while the rest of the crew catches a flick waiting for their turn to play.
Feel the warmth of 200 year old post and beam construction

The Historic Rideout

6 bedrooms·6 baths
Weston • Vermont
4.92(36 reviews)

1695,78 $ USD 1467,77 $ USD total por 3 noches

23–26 oct 2026

Vermont Mountain Chalet • Hot Tub • Near Skiing
Vermont Mountain Chalet • Hot Tub • Near Skiing
Vermont Mountain Chalet • Hot Tub • Near Skiing
Vermont Mountain Chalet • Hot Tub • Near Skiing
Vermont Mountain Chalet • Hot Tub • Near Skiing

Vermont Mountain Chalet • Hot Tub • Near Skiing

4 bedrooms·3½ baths
Plymouth • Vermont

1497,62 $ USD total por 3 noches

27–30 oct 2026

Property grounds
Exterior
.
Reading Farms Estate Front Lawns
Barn cat walk.

Reading Farms Estate

15 bedrooms·10 baths
Reading • Vermont

12.292,00 $ USD total por 3 noches

23–26 oct 2026

Valley Views with Hot Tub
Valley Views with Hot Tub
Valley Views with Hot Tub
Valley Views with Hot Tub
Valley Views with Hot Tub

Valley Views with Hot Tub

4 bedrooms·3½ baths
Windham • Vermont
Relax by the fire in our 8 leather recliners & 3 bean bag chairs
Eat Breakfast by the Pellet Stove & Feel the vibes of 1830s Post & Beam Construction
Our Expansive Chef's Kitchen
Enjoy our brand new 7 person Jacuzzi hot tub
Have yourself a steam in our Sauna

Red Brick Retreat

8 bedrooms·6 baths
Londonderry • Vermont
5(25 reviews)

5024,44 $ USD 4149,35 $ USD total por 3 noches

23–26 oct 2026

Londonderry Loft with Sauna
Londonderry Loft with Sauna
Londonderry Loft with Sauna
Londonderry Loft with Sauna
Londonderry Loft with Sauna

Londonderry Loft with Sauna

4 bedrooms·2 baths
Londonderry • Vermont
Magic Circle home-Private Hot Tub, Fire pit+ more!
Magic Circle home-Private Hot Tub, Fire pit+ more!
Magic Circle home-Private Hot Tub, Fire pit+ more!
Magic Circle home-Private Hot Tub, Fire pit+ more!
Magic Circle home-Private Hot Tub, Fire pit+ more!

Magic Circle home-Private Hot Tub, Fire pit+ more!

4 bedrooms·2 baths
Londonderry • Vermont
Jacuzzi Tub!
Welcome to our chalet!
We have 2 pellet stoves!
Sunroom
Comfort is our priority!

Hot Tub Chalet on Magic Mountain

5 bedrooms·2½ baths
Londonderry • Vermont
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Glen Rd Mountain Retreat

3 bedrooms·2 baths
Peru • Vermont

1259,66 $ USD total por 3 noches

26–29 oct 2026

The private deck hot tub is included on peak-season weekends from late December to mid-March. Otherwise, optional use requires a $195 setup fee.
Choose a sofa by the windows, with the gas fireplace beside the seating area.
Cook in the full kitchen and bring meals straight to the table beside it.
The king bed sits beneath the single bed in the condo's one bedroom.
The living room opens toward the bedroom, with the gas fireplace beside the television.

Trailside Village 3 in Killington

1 bedroom·1 bath
Killington • Vermont
4.86(35 reviews)

1946,99 $ USD total por 3 noches

30 oct – 2 nov 2026