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(24 reviews)

$3,565.96 USD $3,274.27 USD total for 3 nights

Sep 11 – 14, 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
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 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)
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
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
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)

$1,745.18 USD $1,507.29 USD total for 3 nights

Sep 7 – 10, 2026

Enjoy a crackling fire in our living room and open kitchen
Jacuzzi Tub Added July '23
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 2 (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

$2,572.72 USD total for 3 nights

Sep 7 – 10, 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)

$1,137.44 USD total for 3 nights

Sep 7 – 10, 2026

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

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
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

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 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

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

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

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

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)
Stratton Hollow House
Stratton Hollow House
Stratton Hollow House
Stratton Hollow House
Stratton Hollow House

Stratton Hollow House

4 bedrooms·2 baths
Jamaica • Vermont
5(1 review)
Snowdrift
Snowdrift
Snowdrift
Snowdrift
Snowdrift

Snowdrift

4 bedrooms·3 baths
Winhall • Vermont
4.71(7 reviews)

$1,600.29 USD total for 3 nights

Sep 7 – 10, 2026

The Bears Den
The Bears Den
The Bears Den
The Bears Den
The Bears Den

The Bears Den

4 bedrooms·3 baths
Winhall • Vermont
4.5(2 reviews)

$1,400.66 USD total for 3 nights

Sep 7 – 10, 2026

The warm and inviting living room has direct access to the patio with a view of the pond and fountain. The gas fireplace operates with the simple turn of a timer switch.
Heated year-round, the beautiful pool, hot tubs and sauna are just steps from Rising Bear Lodge.
Beautiful architecture and design inside and out.
Luxury Condo*Walk to Ski Lifts*Hot Tub*Pool*Sauna!
Luxury Condo*Walk to Ski Lifts*Hot Tub*Pool*Sauna!

Luxury Condo*Walk to Ski Lifts*Hot Tub*Pool*Sauna!

2 bedrooms·2 baths
Winhall • Vermont
5(89 reviews)

$2,186.55 USD total for 3 nights

Sep 12 – 15, 2026