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

$1,348.78 USD total for 3 nights

Nov 24 – 27, 2026

Living room is equipped with large handmade Chesterfield leather sofa, two vintage leather club chairs and vintage leather recliner. An exceptionally large wood-burning fireplace flanked by antique ski equipment adds warmth for cold Vermont nights.
Living room with large handmade Chesterfield leather sofa, two vintage leather club chairs and vintage leather recliner chair is perfect for snuggling up in front of fire with a good book, or binging on a new Netflix series.
The open plan living and dining room with 8 seat table and antique handmade ski light fixture make Kilbourne Lodge a perfect place to both entertain and relax.
Present day Kilbourne Lodge. A mid-century angled roof ski chalet with large accent stone wall. Front deck features a vintage 2-seater ski lift chair painted in bright red. 100% Instagram worthy!
King bed with memory foam mattress, individual reading lights and ski-shoe side-tables.

Kilbourne Lodge︙3BR/2BA＋Pets＋Fireplace＋Boot Dryer

3 bedrooms·2 baths
Killington • Vermont
4.91(33 reviews)

$1,092.60 USD total for 3 nights

Oct 30 – Nov 2, 2026

Heavenly Killington 16 ppl, 7 bedrooms, 4 bathrooms, 11 beds. Free parking for 10+ cars. Tesla charger.
Heavenly Killington 16 ppl, 7 bedrooms, 4 bathrooms, 11 beds. Free parking for 10+ cars. Tesla charger.
House front view
Unit 1 Great room
Unit 1 Great room

Heavenly Killington

7 bedrooms·4 baths
Killington • Vermont
4.99(85 reviews)

$2,847.60 USD $2,619.34 USD total for 3 nights

Oct 30 – Nov 2, 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)

$1,374.89 USD total for 5 nights

Oct 30 – Nov 4, 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)

$1,374.89 USD total for 5 nights

Oct 30 – Nov 4, 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)

$2,296.00 USD total for 3 nights

Oct 30 – Nov 2, 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

Oct 30 – Nov 4, 2026

The fireplace anchors a generous seating area for conversation, movies, or a quiet evening at home.
Enjoy the hot tub in a wood-paneled room just steps from the living area and yard.
Pull up an Adirondack chair for an evening around the backyard fire pit.
Wood cabinetry, generous counters, and full-size appliances provide a practical place to cook for the group.
Share meals beside the soaring windows, then move easily into the adjoining living room.

The Maple Leaf | Private Indoor Hot Tub

3 bedrooms·2 baths
Killington • Vermont
4.8(5 reviews)

$1,579.72 USD total for 3 nights

Oct 30 – Nov 2, 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)

$1,195.00 USD total for 3 nights

Oct 30 – Nov 2, 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
$190/ 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)
Autumn Views
Summer Views
Winter Views
Winter Views
Wrap Around Deck

Killington Grandview House

7 bedrooms·6½ baths
Mendon • Vermont
4.86(7 reviews)

$4,576.50 USD total for 3 nights

Oct 30 – Nov 2, 2026

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(87 reviews)

$1,097.47 USD $934.75 USD total for 3 nights

Oct 30 – Nov 2, 2026

Carriage House
Carriage House
Carriage House
Carriage House
Carriage House

Carriage House

2 bedrooms·2 baths
Mount Holly • Vermont

$927.00 USD total for 3 nights

Oct 30 – Nov 2, 2026

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
The Ultimate Vermont Getaway
The Ultimate Vermont Getaway
The Ultimate Vermont Getaway
The Ultimate Vermont Getaway
The Ultimate Vermont Getaway

The Ultimate Vermont Getaway

4 bedrooms·3 baths
Rutland • Vermont
5(10 reviews)

$1,205.03 USD total for 3 nights

Nov 4 – 7, 2026

Our farm, wedding ski rental mountain setting
Epic Farm, House, Barn image 16
Barn wedding - farm wedding booked custom Satoyama Mountain Farm
Ski house, great room with dining rooms in back
Epic Farm, House, Barn image 4

Epic Mountain Views, House, Farm Stay, Barn

7 bedrooms·3½ baths
Rochester • Vermont
4.9(29 reviews)

$3,418.00 USD $2,538.70 USD total for 3 nights

Oct 30 – Nov 2, 2026

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)

$1,494.52 USD $1,306.77 USD total for 3 nights

Oct 30 – Nov 2, 2026