Drop Point Cabin
Drop Point Cabin
Drop Point Cabin
Drop Point Cabin
Drop Point Cabin

Drop Point Cabin

4 bedrooms·3 baths
Jamaica • Vermont
4.72(25 reviews)
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)

$1,156.87 USD total for 3 nights

Sep 7 – 10, 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

$639.45 USD total for 3 nights

Oct 1 – 4, 2026

Free cancellation
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

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

$9,369.15 USD total for 30 nights

Oct 1 – 31, 2026

Free cancellation
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
Winter Wonderland
Hot tub and Sauna.. and silence
Try 30 minutes in the sauna...after full day of skiing
Living Room Retreat: Sunlit space with vaulted ceilings and stylish decor for perfect relaxation!
Delight in the hottub when its cool outside

Stratton Ski Haus

4 bedrooms·2½ baths
Jamaica • Vermont

$2,053.91 USD $1,737.29 USD total for 3 nights

Sep 7 – 10, 2026

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

Stratton Vacay Chalet

3 bedrooms·2 baths
Winhall • Vermont

$3,892.00 USD total for 5 nights

Sep 7 – 12, 2026

Casita Bacon
Casita Bacon
Casita Bacon
Casita Bacon
Casita Bacon

Casita Bacon

4 bedrooms·4 baths
Winhall • Vermont

$1,132.06 USD total for 3 nights

Sep 7 – 10, 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)

$912.00 USD total for 3 nights

Sep 7 – 10, 2026

The Azimuth
The Azimuth
The Azimuth
The Azimuth
The Azimuth

The Azimuth

4 bedrooms·2 baths
Sunderland • Vermont

$1,170.95 USD total for 3 nights

Sep 7 – 10, 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

Sep 7 – 10, 2026

The Deming House
The Deming House
The Deming House
The Deming House
The Deming House

The Deming House

3 bedrooms·4 baths
Arlington • Vermont
4(1 review)
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)

$1,042.94 USD total for 3 nights

Sep 7 – 10, 2026

Front of house
Living room
Front yard and house
Guard rails have been added both sides of stairs since this picture was taken.
Looking up toward loft area with partial view of kitchen lower right. Note the spiral staircase.

Cozy converted barn on secluded 6.5 acres

3 bedrooms·1 bath
Shaftsbury • Vermont
5(390 reviews)

$916.60 USD total for 3 nights

Sep 22 – 25, 2026

Gorgeous, modern, new 3-bedroom home on pond.
Gorgeous, modern, new 3-bedroom home on pond.
Gorgeous, modern, new 3-bedroom home on pond.
Gorgeous, modern, new 3-bedroom home on pond.
The cottage is in the building on the right. Behind the unit is the animal yard.

Gorgeous, modern, new 3-bedroom home on pond.

3 bedrooms·2 baths
Guilford • Vermont
5(25 reviews)

$1,040.00 USD total for 3 nights

Sep 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

$1,076.15 USD total for 3 nights

Sep 13 – 16, 2026

The Tower House
The Tower House
The Tower House
The Tower House
The Tower House

The Tower House

4 bedrooms·2 baths
Londonderry • Vermont
4.89(9 reviews)
Londonderry Links
Londonderry Links
Londonderry Links
Londonderry Links
Londonderry Links

Londonderry Links

3 bedrooms·2 baths
Londonderry • Vermont
4.88(25 reviews)
$200/ night(excl. fees & taxes)
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)

$934.30 USD total for 3 nights

Sep 8 – 11, 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)

$546.13 USD total for 3 nights

Sep 7 – 10, 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

Sep 7 – 10, 2026

the view of the front of the home with the wrap around deck!
This is the view of the rear of the home
the access ramp
entry to the home at the rear.
Enter via the mudroom and please remove your shoes!

Manchester Santuary II

4 bedrooms·4½ baths
Manchester • Vermont
5(1 review)

$1,925.50 USD total for 3 nights

Sep 7 – 10, 2026

Manchester Sanctuary escape to Vermont!
Manchester Sanctuary escape to Vermont!
Manchester Sanctuary escape to Vermont!
Manchester Sanctuary escape to Vermont!
Manchester Sanctuary escape to Vermont!

Manchester Sanctuary escape to Vermont!

3 bedrooms·3½ baths
Manchester • Vermont
5(2 reviews)

$1,756.00 USD total for 3 nights

Sep 30 – Oct 3, 2026

Free cancellation
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