1930s-era cottage.
Hot tub open to the outside and under cover.
Primary bedroom with king bed. Featuring a Puffy mattress, fine linens, plenty of pillows, and a down comforter.
View of the lake from this bedroom
Large screened-in front porch overlooking the lake. Listen to water fowl and peepers at night.

Amherst Guest Cottage ~ One Bedroom

1 bedroom·2 baths
Plymouth • Vermont

$1,191.00 USD total for 3 nights

Nov 1 – 4, 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)

$836.51 USD total for 3 nights

Nov 2 – 5, 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)

$1,234.50 USD total for 3 nights

Oct 23 – 26, 2026

Table is made from reclaimed barn wood and great for a large dinner.
Steps to Farm Rd Estate | Historic 2BR w/ AC! image 2
Relax with some art or watch a great movie in the Great Room on the comfy sofa.
Reclaimed barnwood table
The large bedroom on the first floor was transformed from the art gallery.

Historic 1827 House | 2BR • Walkable location

2 bedrooms·1 bath
Dover • Vermont
5(61 reviews)

$1,920.18 USD total for 3 nights

Mar 19 – 22, 2027

Open-concept living, dining, and kitchen area — designed for gathering, relaxing, and entertaining larger groups.
Open-Concept Great Room, Dining Room and Kitchen - Plenty of space for everyone to spread out
Cozy Great Room with Propane Fireplace — The perfect place to relax after a full day skiing Jay Peak’s legendary powder.
Cozy Great Room with Propane Fireplace — The perfect place to relax after a full day skiing Jay Peak’s legendary powder.
Unbeatable ski-in/ski-out location right near the Tramside lifts, the Pump House Water Park and the Ice Rink

Jay Peak Luxury Tramside Condo | Ski-In/Out | Walk Everywhere | Steps to Waterpark | Dog Friendly

3 bedrooms·2 baths
Jay • Vermont
5(26 reviews)

$1,525.70 USD total for 3 nights

Oct 26 – 29, 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 23 – 26, 2026

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

Oct 25 – 28, 2026

Rustic, cozy log cabin in Jay, VT ~2 mi Jay Peak image 1
Rustic, cozy log cabin in Jay, VT ~2 mi Jay Peak image 2
Best view of the mountain range and Jay Peak from your sitting spot in the living room. Opens up to the dining. Wood stove is not available for use at this time. Board games and books provided.
Rustic, cozy log cabin in Jay, VT ~2 mi Jay Peak image 4
Rustic, cozy log cabin in Jay, VT ~2 mi Jay Peak image 5

Rustic, cozy log cabin in Jay, VT ~2 mi Jay Peak

3 bedrooms·2 baths
Jay • Vermont
5(23 reviews)

$1,172.60 USD total for 3 nights

Oct 23 – 26, 2026

Open comfy space with wide floor boards and spiral access to the large loft.
Relax by the gas fireplace on second floor
The 1827 House has easy access from RT 100 where you can walk to fine restaurants and venture to close by Wilmington, Manchester and lots of trails!
Comfortable and romantic Queen Victorian room
Loft Queen beds

Historic 1827 House | 3BR • AC • Upstairs

3 bedrooms·2 baths
Dover • Vermont
5(28 reviews)

$969.85 USD total for 3 nights

Oct 26 – 29, 2026

Air Vermont Apartment
Air Vermont Apartment
Air Vermont Apartment
Air Vermont Apartment
Air Vermont Apartment

Air Vermont Apartment

1 bedroom·1 bath
South Burlington • Vermont
4.95(77 reviews)

$759.14 USD total for 3 nights

Oct 27 – 30, 2026

Official Direct Booking Site | Brookside Cabin - Your Peaceful VT Off-Grid Escape
Official Direct Booking Site | Brookside Cabin - Your Peaceful VT Off-Grid Escape
Official Direct Booking Site | Brookside Cabin - Your Peaceful VT Off-Grid Escape
Official Direct Booking Site | Brookside Cabin - Your Peaceful VT Off-Grid Escape
Official Direct Booking Site | Brookside Cabin - Your Peaceful VT Off-Grid Escape

Official Direct Booking Site | Brookside Cabin - Your Peaceful VT Off-Grid Escape

3 bedrooms·1 bath
Brookfield • Vermont
4.88(16 reviews)

$700.00 USD total for 3 nights

Oct 25 – 28, 2026

Handcrafted VT Chalet • Walk to Lake • Fire Pit image 1
Spacious open floor plan with fireplace, vaulted ceilings and natural light.
Handcrafted VT Chalet • Walk to Lake • Fire Pit image 3
Handcrafted VT Chalet • Walk to Lake • Fire Pit image 4
Full bathroom with all the amenities.

Handcrafted Log Chalet (sleeps 2-4)

1 bedroom·1 bath
Warren • Vermont

$710.64 USD total for 3 nights

Oct 25 – 28, 2026

14 Acre Waterfront estate on Lake Champlain
14 Acre Waterfront estate on Lake Champlain
14 Acre Waterfront estate on Lake Champlain
14 Acre Waterfront estate on Lake Champlain
The front yard down to the water, so much space for so many possibilities

14 Acre Waterfront estate on Lake Champlain

3 bedrooms·3 baths
Grand Isle • Vermont
4.8(5 reviews)

$2,514.00 USD $2,282.60 USD total for 5 nights

Oct 23 – 28, 2026

The Great Room was once the village general store and Post Office. Imagine the conversations over the years in this room.
Easy access on RT100.
Upstairs living area. Views of mount snow ski area from north side windows.
Futon in Loft sleeps two. Great for overflow skiers.
Relax by the gas fireplace on second floor after a day of skiing. Mini Split for quiet & comfortable AC in the summer and heat in the winter.

Historic 1827 House | 5BR • AC • Walkable

5 bedrooms·3 baths
Dover • Vermont
5(20 reviews)
$500 – $750/ night(excl. fees & taxes)
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 23 – 26, 2026

Room
Property grounds
Private kitchen
Living area
Room

Mad River Valley furnished 1BR apartment,full kitchen/bath 20 minutes to skiing

1 bedroom·1 bath
Moretown • Vermont

$450.00 USD total for 3 nights

Nov 1 – 4, 2026

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)

$5,024.44 USD $4,149.35 USD total for 3 nights

Oct 23 – 26, 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

$1,455.18 USD total for 3 nights

Nov 24 – 27, 2026

Our farm, wedding ski rental mountain setting
Epic Farm, House, Barn image 16
Barn wedding - farm wedding booked custom Satoyama Mountain Farm
Ski house, great room with dining rooms in back
Epic Farm, House, Barn image 4

Epic Mountain Views, House, Farm Stay, Barn

7 bedrooms·3½ baths
Rochester • Vermont
4.9(29 reviews)

$3,418.00 USD $2,538.70 USD total for 3 nights

Oct 23 – 26, 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)

$866.24 USD total for 3 nights

Oct 23 – 26, 2026

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)

$1,695.78 USD $1,467.77 USD total for 3 nights

Oct 23 – 26, 2026

Tranquil Treetop Retreat
image-4
Tranquil Treetop Retreat
Tranquil Treetop Retreat
Tranquil Treetop Retreat

Tranquil Treetop Retreat

4 bedrooms·4 baths
Winhall • Vermont
4.75(16 reviews)

$1,718.50 USD total for 3 nights

Oct 24 – 27, 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)

$1,271.12 USD total for 3 nights

Oct 23 – 26, 2026

Hillside Getaway
Hillside Getaway
Hillside Getaway
Hillside Getaway
Hillside Getaway

Hillside Getaway

3 bedrooms·2 baths
Sandgate • Vermont
5(17 reviews)

$1,370.21 USD total for 3 nights

Oct 25 – 28, 2026