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

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
5(83 reviews)

$2,838.56 USD $2,611.21 USD total for 3 nights

Sep 7 – 10, 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)

$1,248.80 USD total for 3 nights

Sep 7 – 10, 2026

Epic Farm, House, Barn image 1
Epic Farm, House, Barn image 2
Dog not included
Epic Farm, House, Barn image 4
Epic Farm, House, Barn image 5

Epic House, Barn, Farm

11 bedrooms·3½ baths
Rochester • Vermont
4.9(29 reviews)
$791/ night(excl. fees & taxes)
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

$1,666.24 USD total for 3 nights

Nov 24 – 27, 2026

Free cancellation
Autumn Views
Summer Views
Winter Views
Winter Views
Wrap Around Deck

Killington Grandview House

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

$4,027.55 USD total for 3 nights

Sep 7 – 10, 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 total for 4 nights

Sep 7 – 11, 2026

Official Direct Booking Site | Brookside Cabin - Your Peaceful VT Off-Grid Escape
Official Direct Booking Site | Brookside Cabin - Your Peaceful VT Off-Grid Escape
Official Direct Booking Site | Brookside Cabin - Your Peaceful VT Off-Grid Escape
Official Direct Booking Site | Brookside Cabin - Your Peaceful VT Off-Grid Escape
Official Direct Booking Site | Brookside Cabin - Your Peaceful VT Off-Grid Escape

Official Direct Booking Site | Brookside Cabin - Your Peaceful VT Off-Grid Escape

3 bedrooms·1 bath
Brookfield • Vermont
4.88(16 reviews)

$685.00 USD total for 3 nights

Sep 7 – 10, 2026

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)
$406 – $2,670/ night(excl. fees & taxes)
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

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

Unwind in comfort! Settle into the cozy couch and enjoy your favorite shows on the Smart TV after a day of adventure.
Cozy up by the wood-burning stove or gaze at the stars with the telescope—relaxation and adventure all in one space!
Gather around for home-cooked meals in this inviting dining space.
The perfect spot for game night or a laid-back evening with friends.
Welcome to Vermont Retreat! A cozy 3BR home surrounded by stunning mountain views and nature’s beauty—your perfect escape awaits!

Vermont Retreat: 3BR with Mountain Views & Trails

3 bedrooms·2 baths
Brookfield • Vermont

$1,218.56 USD total for 3 nights

Sep 7 – 10, 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

$1,497.62 USD total for 3 nights

Oct 27 – 30, 2026

Free cancellation
Living room 2 - this space can be bright and open, or close the shades on the skylights and have a cozy, warm nook.
Cabin at dusk.
Bedroom 3 - the sunroom. Surrounded by windows with a door leading to the covered porch w/ swing and a bistro table. Perfect for catching sunrise! A second door leads to a private woodland garden.
Sitting window found in Bedroom 1 (Large Loft). Views of backyard, fire pit, and perennial gardens.
Living room 1

Kismet Cabin: Ski Sugarbush & Summer Lake Days

3 bedrooms·2 baths
Warren • Vermont
5(32 reviews)

$2,308.31 USD total for 3 nights

Oct 10 – 13, 2026

Free cancellation
Handcrafted VT Chalet • Walk to Lake • Fire Pit image 1
Spacious open floor plan with fireplace, vaulted ceilings and natural light.
Handcrafted VT Chalet • Walk to Lake • Fire Pit image 3
Handcrafted VT Chalet • Walk to Lake • Fire Pit image 4
Full bathroom with all the amenities.

Handcrafted Log Chalet (sleeps 2-4)

1 bedroom·1 bath
Warren • Vermont

$1,160.71 USD total for 3 nights

Oct 10 – 13, 2026

Free cancellation
Private entrance with a spacious deck nestled high among the trees—perfect for savoring your morning coffee, soaking in the fresh Vermont air, or enjoying the peaceful silence.
Open living room and kitchen area. 40' smart TV, full size pull out sofa bed, 2 bar stools at kitchen counter for dining. Door leads to 2nd story deck & stairs (summer entrance). Interior stairs are the winter entrance through garage.
Queen bedroom with a plush new mattress topper and soft, cozy bedding.
Bright, clean bathroom stocked with all the essentials—plus a little extra to make your stay more comfortable!
Whether you're playing lawn games, reading beneath the trees, or simply stretching out in an Adirondack chair, there's room to enjoy Vermont at your own pace.

Alpine Apartment Suite

1 bedroom·1 bath
Warren • Vermont
5(51 reviews)

$729.35 USD total for 3 nights

Sep 11 – 14, 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

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

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

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

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)
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)