Location

Dates

Guests

Vacation rentals in Ludlow, Vermont, United States

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(87 reviews)

$ 1.097,47 USD $ 934,75 USD totaal voor 3 nachten

8–11 nov 2026

Winter Wonderland! Great Okemo rental.

Lazy Afternoon in Paradise

Open Space & Relaxation. The Ultimate Social Distancing Escape!

Fresh Air with Wifi. (If You're into that Sort of Thing....)

Classic Vermont - Historic Renovated Dairy Farm (No Cows Anymore)

2 Bdrm, Lower Level, Okemo, 25 Acre Mtn Playground

2 bedrooms·1 bath

Cavendish • Vermont

5(27 reviews)

$ 1.104,88 USD totaal voor 5 nachten

8–13 nov 2026

Front View of The Farmhouse - The Second Story is All Yours

Open Space & Relaxation. The Ultimate Social Distancing Escape!

Classic Vermont - Historic Renovated Dairy Farm (No Cows Anymore)

Lazy Afternoon in Paradise

Fresh Air with Wifi. (If You're into that Sort of Thing....)

2 Bdrm, Upper Level, Okemo, 25 Acre Mtn Playground

2 bedrooms·1 bath

Cavendish • Vermont

5(13 reviews)

$ 1.104,88 USD totaal voor 5 nachten

8–13 nov 2026

Property grounds

Summer fun on lake - great for 2 families or 3 couples - newly remodeled

4 bedrooms·2 baths

Windsor County • Vermont

$ 4.000,00 USD totaal voor 5 nachten

8–13 nov 2026

Lake Rescue Chalet-6-BR Lake & Ski House w/Hot Tub

Lake Rescue Chalet-6-BR Lake & Ski House w/Hot Tub

Lake Rescue Chalet-6-BR Lake & Ski House w/Hot Tub

Lake Rescue Chalet-6-BR Lake & Ski House w/Hot Tub

Lake Rescue Chalet-6-BR Lake & Ski House w/Hot Tub

Lake Rescue Chalet-6-BR Lake & Ski House w/Hot Tub

6 bedrooms·2 baths

Ludlow • Vermont

5(107 reviews)

$ 2.072,00 USD totaal voor 3 nachten

8–11 nov 2026

Carriage House

2 bedrooms·2 baths

Mount Holly • Vermont

$ 927,00 USD totaal voor 3 nachten

8–11 nov 2026

Mount Holly Lake & Ski Hideaway

Mount Holly Lake & Ski Hideaway

Mount Holly Lake & Ski Hideaway

Fall in Mount Holly

Mount Holly Lake & Ski Hideaway

Mount Holly Lake & Ski Hideaway

4 bedrooms·2 baths

Mount Holly • Vermont

5(37 reviews)

$299/ nacht(excl. kosten & belastingen)

Spacious living room

Fully stocked kithcen

Queen bedroom with natural light

Welcome to our cozy home!

Rural Chester Farmhouse

3 bedrooms·2 baths

Chester • 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)

$ 1.640,34 USD $ 1.531,89 USD totaal voor 3 nachten

9–12 nov 2026

Vermont Mountain Chalet • Hot Tub • Near Skiing

Vermont Mountain Chalet • Hot Tub • Near Skiing

Vermont Mountain Chalet • Hot Tub • Near Skiing

Vermont Mountain Chalet • Hot Tub • Near Skiing

Vermont Mountain Chalet • Hot Tub • Near Skiing

Vermont Mountain Chalet • Hot Tub • Near Skiing

4 bedrooms·3½ baths

Plymouth • Vermont

$ 1.498,65 USD totaal voor 3 nachten

8–11 nov 2026

Property grounds

Reading Farms Estate Front Lawns

Reading Farms Estate

15 bedrooms·10 baths

Reading • Vermont

$ 12.292,00 USD totaal voor 3 nachten

8–11 nov 2026

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

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

Have yourself a steam in our Sauna

Red Brick Retreat

8 bedrooms·6 baths

Londonderry • Vermont

5(25 reviews)

$ 3.930,58 USD $ 3.602,43 USD totaal voor 3 nachten

9–12 nov 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

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!

3 bedrooms·2 baths

Londonderry • Vermont

Welcome to our chalet!

We have 2 pellet stoves!

Comfort is our priority!

Hot Tub Chalet on Magic Mountain

5 bedrooms·2½ baths

Londonderry • Vermont

Glen Rd Mountain Retreat

3 bedrooms·2 baths

Peru • Vermont

$ 1.342,26 USD totaal voor 3 nachten

8–11 nov 2026

The private deck hot tub is included on peak-season weekends from late December to mid-March. Otherwise, optional use requires a $195 setup fee.

Choose a sofa by the windows, with the gas fireplace beside the seating area.

Cook in the full kitchen and bring meals straight to the table beside it.

The king bed sits beneath the single bed in the condo's one bedroom.

The living room opens toward the bedroom, with the gas fireplace beside the television.

Trailside Village 3 in Killington

1 bedroom·1 bath

Killington • Vermont

4.86(35 reviews)

$ 1.946,99 USD totaal voor 3 nachten

13–16 nov 2026

The private hot tub is included on peak-season weekends from late December to mid-March. Otherwise, arrange optional $195 setup with management.

The wood stove and two sofas share the main living space; firewood is supplied.

Use the private cedar sauna without leaving the condo.

Prepare meals in the kitchen, with a gas stove and dishwasher for cleanup.

The bedroom has a king bed, separate from the living room's sofa beds.

Trailside Village 1 in Killington

1 bedroom·1 bath

Killington • Vermont

5(25 reviews)

$ 2.001,37 USD totaal voor 3 nachten

8–11 nov 2026

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 totaal voor 4 nachten

8–12 nov 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)

$ 1.396,52 USD totaal voor 3 nachten

8–11 nov 2026

Coffee and conversation come easily with comfortable seating beside the balcony doors.

The resort's shared seasonal outdoor pool has a surrounding deck with loungers and umbrellas.

Make coffee and breakfast before heading out, or settle in for dinner at the condo.

Separate beds suit travel companions who prefer their own sleeping space.

The shared indoor pool in Building 3 includes marked lap lanes and a tiled deck.

The Slopeside Solace | Mountain Green 1B3

2 bedrooms·1½ baths

Killington • Vermont

4.33(3 reviews)

$ 1.008,04 USD totaal voor 3 nachten

8–11 nov 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 totaal voor 3 nachten

8–11 nov 2026

Cozy Bromley Retreat — Ski-In, Ski-Out

Cozy Bromley Retreat — Ski-In, Ski-Out

Cozy Bromley Retreat — Ski-In, Ski-Out

Cozy Bromley Retreat — Ski-In, Ski-Out

Cozy Bromley Retreat — Ski-In, Ski-Out

Cozy Bromley Retreat — Ski-In, Ski-Out

1 bedroom·1 bath

Peru • Vermont

5(1 review)

$ 706,53 USD totaal voor 3 nachten

8–11 nov 2026