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)
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

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

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
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

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

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

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

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

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

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

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

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

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
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

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)
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)
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

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

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)
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