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)
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

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 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

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

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

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
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

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

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

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)

$1,375.00 USD total for 5 nights

Sep 7 – 12, 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

$1,666.24 USD total for 3 nights

Nov 24 – 27, 2026

Free cancellation
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

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)
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

Enjoy the expansive views from our cozy living room
Mountain View Manor
King of the Hill views from the firepit
Chef's Kitchen and seating for 12
Read a book while swinging in our hammock chairs

Mountain View Manor

6 bedrooms·5 baths
Windsor County • Vermont

$3,966.87 USD total for 3 nights

Oct 1 – 4, 2026

Free cancellation
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
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)
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 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