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)

$8,827.87 USD total for 3 nights

Oct 30 – Nov 2, 2026

A cozy cabin-style home with a wooden deck, nestled among lush greenery, featuring Adirondack chairs on a stone-lined lawn.
A cozy living room with a loft, featuring a leather sectional, woven chairs, and a rustic staircase leading to an upper level.
A cozy backyard fire pit area with four wooden Adirondack chairs arranged around a circular stone pit. Surrounded by lush green grass and dense trees, it offers a serene outdoor retreat.
A cozy bedroom featuring a black metal bunk bed with a full-size lower and twin upper. The wooden-paneled walls and carpeted floor add warmth, while a telescope by the window invites stargazing.
A rustic wooden deck extends from the house, surrounded by lush greenery. Three wicker chairs with cushions offer a peaceful spot to relax and enjoy the natural surroundings.

6BD 3BA - Mount Snow VT - Ski-Back Trail - Shuttle

6 bedrooms·3 baths
Dover • Vermont

$2,305.00 USD total for 3 nights

Oct 30 – Nov 2, 2026

2BD 1BA - Mount Snow VT - Ski-Back Trail - Shuttle
2BD 1BA - Mount Snow VT - Ski-Back Trail - Shuttle
2BD 1BA - Mount Snow VT - Ski-Back Trail - Shuttle
As you step inside you'll be assured that you chose the right place!
2BD 1BA - Mount Snow VT - Ski-Back Trail - Shuttle

2BD 1BA - Mount Snow VT - Ski-Back Trail - Shuttle

2 bedrooms·1 bath
Dover • Vermont

$648.80 USD total for 3 nights

Oct 30 – Nov 2, 2026

Main living area with large couch and 4 lounge chairs, fireplace and TV
4BD 2BA - Mount Snow VT - Ski-Back Trail - Shuttle
Chalet style home on private lot, wrap around deck
4BD 2BA - Mount Snow VT - Ski-Back Trail - Shuttle
4BD 2BA - Mount Snow VT - Ski-Back Trail - Shuttle

4BD 2BA - Mount Snow VT - Ski-Back Trail - Shuttle

4 bedrooms·2 baths
Dover • Vermont

$955.80 USD total for 3 nights

Oct 30 – Nov 2, 2026

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
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 total for 5 nights

Oct 30 – Nov 4, 2026

Luxe VT Retreat • Perfect for Remote Summer Stays
Luxe VT Retreat • Perfect for Remote Summer Stays
Luxe VT Retreat • Perfect for Remote Summer Stays
Luxe VT Retreat • Perfect for Remote Summer Stays
Luxe VT Retreat • Perfect for Remote Summer Stays

Luxe VT Retreat • Perfect for Remote Summer Stays

2 bedrooms·2 baths
Newfane • Vermont
4.5(2 reviews)

$996.45 USD total for 3 nights

Nov 8 – 11, 2026

Riverside Getaway + Wood-Fired Sauna
Riverside Getaway + Wood-Fired Sauna
Riverside Getaway + Wood-Fired Sauna
Riverside Getaway + Wood-Fired Sauna
Riverside Getaway + Wood-Fired Sauna

Riverside Getaway + Wood-Fired Sauna

0 bedrooms·1 bath
Newfane • Vermont

$493.50 USD total for 3 nights

Oct 30 – Nov 2, 2026

Casita Bacon
Casita Bacon
Casita Bacon
Casita Bacon
Casita Bacon

Casita Bacon

4 bedrooms·4 baths
Winhall • Vermont

$1,027.53 USD total for 3 nights

Oct 30 – Nov 2, 2026

Cozy Chalet 12 Min to Stratton & 7 Min to Bromley
Cozy Chalet 12 Min to Stratton & 7 Min to Bromley
Cozy Chalet 12 Min to Stratton & 7 Min to Bromley
Cozy Chalet 12 Min to Stratton & 7 Min to Bromley
Cozy Chalet 12 Min to Stratton & 7 Min to Bromley

Cozy Chalet 12 Min to Stratton & 7 Min to Bromley

4 bedrooms·2 baths
Winhall • Vermont
5(10 reviews)

$902.00 USD total for 3 nights

Oct 30 – Nov 2, 2026

Open concept living and dining room; plenty of seating at the dinner table
Top of the Rock
View of the house from the backyard
A winter snowfall
Our driveway can easily fit 2-3 cars

Top of the Rock

4 bedrooms·2 baths
Wilmington • Vermont
4.77(13 reviews)

$1,375.00 USD total for 3 nights

Oct 30 – Nov 2, 2026

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
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
Stratton Chalet 5 minute drive to Bromley 10 to Stratton
Stratton Chalet 5 minute drive to Bromley 10 to Stratton
Stratton Chalet 5 minute drive to Bromley 10 to Stratton
Stratton Chalet 5 minute drive to Bromley 10 to Stratton
Stratton Chalet 5 minute drive to Bromley 10 to Stratton

Stratton Chalet 5 minute drive to Bromley 10 to Stratton

4 bedrooms·5 baths
Winhall • Vermont
5(8 reviews)

$1,169.32 USD total for 3 nights

Oct 30 – Nov 2, 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
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)
$618 – $2,060/ night(excl. fees & taxes)
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
The Little Matterhorn
The Little Matterhorn
The Little Matterhorn
The Little Matterhorn
The Little Matterhorn

The Little Matterhorn

3 bedrooms·2 baths
Winhall • Vermont
4.87(30 reviews)

$845.58 USD total for 3 nights

Nov 2 – 5, 2026

Cozy Bromley Retreat
Cozy Bromley Retreat
Cozy Bromley Retreat
Cozy Bromley Retreat
Cozy Bromley Retreat

Cozy Bromley Retreat

1 bedroom·1 bath
Peru • Vermont
5(1 review)

$644.57 USD total for 3 nights

Oct 30 – Nov 2, 2026

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Glen Rd Mountain Retreat

3 bedrooms·2 baths
Peru • Vermont

$1,259.66 USD total for 3 nights

Oct 30 – Nov 2, 2026

Renovated 2BR on Bromley | Fall Foliage & Hiking
Renovated 2BR on Bromley | Fall Foliage & Hiking
Renovated 2BR on Bromley | Fall Foliage & Hiking
Renovated 2BR on Bromley | Fall Foliage & Hiking
Renovated 2BR on Bromley | Fall Foliage & Hiking

Renovated 2BR on Bromley | Fall Foliage & Hiking

2 bedrooms·1 bath
Peru • Vermont
4.61(28 reviews)

$839.45 USD total for 3 nights

Oct 30 – Nov 2, 2026

Enjoy casual conversations in this cozy living room that is flooded with natural light during the day.
High speed internet available for quick connections and streaming video.
The house is a custom timber frame with distinct and timeless styling that blends into the surrounding area.
Newly added washer and dryer for quick cleanups or drying skiing gear.
Star gazing at night is a perfect way to unwind and enjoy the seclusion.

Tranquil Brookside Retreat with Hot Tub & Firepit

4 bedrooms·2½ baths
Peru • Vermont
5(1 review)

$1,412.84 USD total for 3 nights

Nov 7 – 10, 2026

Shadow Peak Chalet
Shadow Peak Chalet
Shadow Peak Chalet
Shadow Peak Chalet
Shadow Peak Chalet

Shadow Peak Chalet

4 bedrooms·2 baths
Manchester • Vermont

$981.34 USD total for 3 nights

Nov 1 – 4, 2026

HUGE private Mansion! 15 bedroom, 12 bath sleep 34
HUGE private Mansion! 15 bedroom, 12 bath sleep 34
HUGE private Mansion! 15 bedroom, 12 bath sleep 34
HUGE private Mansion! 15 bedroom, 12 bath sleep 34
HUGE private Mansion! 15 bedroom, 12 bath sleep 34

HUGE private Mansion! 15 bedroom, 12 bath sleep 34

15 bedrooms·1 bath
Manchester • Vermont
5(17 reviews)

$10,983.60 USD total for 3 nights

Oct 30 – Nov 2, 2026