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)

$ 1.097,47 USD $ 934,75 USD totaal voor 3 nachten

25–28 okt 2026

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)

$ 3.930,58 USD $ 3.602,43 USD totaal voor 3 nachten

26–29 okt 2026

Front of the house
Cubbies and boot warmers
Spacious mud room
Space for all your gear
Upstairs living room

Burnt Hill Chalet

3 bedrooms·2 baths
Winhall • Vermont

$ 3.640,00 USD totaal voor 5 nachten

24–29 okt 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
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

$ 1.497,62 USD totaal voor 3 nachten

27–30 okt 2026

Settle into the sectional beside the fireplace, with the television above and mountain views through the windows.
Step onto the private balcony for a look across the rooftops toward Pico's trails.
The kitchen has a refrigerator, range and microwave for preparing meals back at the condo.
The queen bed sits beside sliding doors to your private balcony.
The full bathroom has a tub and shower combination with a vanity for getting ready.

Summit View at Pico | Condo with Private Balcony

1 bedroom·1 bath
Killington • Vermont
$408/ nacht(excl. kosten & belastingen)
Outdoor pool is open now!
Welcome to the loft
Premium linens
Walk out balcony
Enough space fore the whole crew

Stratton Loft with Pool

4 bedrooms·2 baths
Winhall • Vermont
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)

$ 2.184,00 USD totaal voor 3 nachten

24–27 okt 2026

Cozy, clean, and bright open-concept living room & kitchen
Mountain view on the deck off the living room
Desk converts to dining table for 4
Unwind with a quiet & serene view of the slopes
Remote work-friendly desk, workspace, high-speed internet

Killington VT Condo - Mountain Green

1 bedroom·1 bath
Killington • Vermont

$ 1.435,53 USD totaal voor 3 nachten

24–27 nov 2026

Coffee and conversation come easily with comfortable seating beside the balcony doors.
The resort's shared seasonal outdoor pool has a surrounding deck with loungers and umbrellas.
Make coffee and breakfast before heading out, or settle in for dinner at the condo.
Separate beds suit travel companions who prefer their own sleeping space.
The shared indoor pool in Building 3 includes marked lap lanes and a tiled deck.

The Slopeside Solace | Mountain Green 1B3

2 bedrooms·1½ baths
Killington • Vermont
4.33(3 reviews)

$ 1.028,92 USD totaal voor 3 nachten

31 okt – 3 nov 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)

$ 1.946,99 USD totaal voor 3 nachten

30 okt – 2 nov 2026

The private hot tub is included on peak-season weekends from late December to mid-March. Otherwise, arrange optional $195 setup with management.
The wood stove and two sofas share the main living space; firewood is supplied.
Use the private cedar sauna without leaving the condo.
Prepare meals in the kitchen, with a gas stove and dishwasher for cleanup.
The bedroom has a king bed, separate from the living room's sofa beds.

Trailside Village 1 in Killington

1 bedroom·1 bath
Killington • Vermont
5(25 reviews)

$ 2.001,37 USD totaal voor 3 nachten

24–27 okt 2026

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)

$ 1.593,00 USD totaal voor 3 nachten

26–29 okt 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

$ 1.191,00 USD totaal voor 3 nachten

1–4 nov 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)

$ 1.107,00 USD totaal voor 3 nachten

26–29 okt 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)

$ 6.582,00 USD totaal voor 6 nachten

24–30 okt 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)

$ 2.294,20 USD totaal voor 3 nachten

26–29 okt 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)

$ 1.919,00 USD totaal voor 3 nachten

26–29 okt 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)

$ 8.826,74 USD totaal voor 3 nachten

24–27 okt 2026

Exterior view of House. Stairs from Driveway and Deck.
Dining Room with chairs for 8
Dining Room. Sliding door with access to east deck & gas Grill
Fully equipped kitchen. New stainless steel look appliances
Leather sofa and love seat

Private House with Fantastic Views off Home Stretch Trail

4 bedrooms·2 baths
Killington • Vermont
5(48 reviews)

$ 2.750,00 USD totaal voor 4 nachten

24–28 okt 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)

$ 1.847,55 USD totaal voor 3 nachten

26–29 okt 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)

$ 1.704,51 USD totaal voor 3 nachten

25–28 okt 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)

$ 1.196,98 USD totaal voor 3 nachten

24–27 okt 2026

Snowfall Retreat
Snowfall Retreat
Snowfall Retreat
Snowfall Retreat
Snowfall Retreat

Snowfall Retreat

3 bedrooms·3 baths
Winhall • Vermont

$ 1.280,60 USD totaal voor 3 nachten

24–27 okt 2026