Location

Dates

Guests

Vacation rentals in Weston, Vermont, United States

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)

$1,546.34 USD $1,348.23 USD total for 3 nights

Oct 27 – 30, 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

Have yourself a steam in our Sauna

Red Brick Retreat

8 bedrooms·6 baths

Londonderry • Vermont

5(25 reviews)

$4,295.20 USD $3,565.96 USD total for 3 nights

Oct 27 – 30, 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

Glen Rd Mountain Retreat

3 bedrooms·2 baths

Peru • Vermont

$1,259.66 USD total for 3 nights

Oct 27 – 30, 2026

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!

4 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

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 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)

$1,412.84 USD total for 3 nights

Nov 7 – 10, 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(87 reviews)

$1,097.47 USD $934.75 USD total for 3 nights

Oct 27 – 30, 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)

$644.57 USD total for 3 nights

Oct 27 – 30, 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

Oct 27 – 30, 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)

$837.07 USD total for 3 nights

Nov 2 – 5, 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

$2,014.73 USD total for 3 nights

Oct 31 – Nov 3, 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

Oct 27 – 30, 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)

$902.00 USD total for 3 nights

Oct 27 – 30, 2026

Front of the house

Cubbies and boot warmers

Spacious mud room

Space for all your gear

Upstairs living room

Burnt Hill Chalet

3 bedrooms·2 baths

Winhall • Vermont

$3,640.00 USD total for 5 nights

Oct 27 – Nov 1, 2026

Outdoor pool is open now!

Welcome to the loft

Walk out balcony

Enough space fore the whole crew

Stratton Loft with Pool

4 bedrooms·2 baths

Winhall • Vermont

Carriage House

2 bedrooms·2 baths

Mount Holly • Vermont

$927.00 USD total for 3 nights

Oct 27 – 30, 2026

Casita Bacon

4 bedrooms·4 baths

Winhall • Vermont

$992.29 USD total for 3 nights

Oct 27 – 30, 2026

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

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)

$1,150.79 USD total for 3 nights

Oct 27 – 30, 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)

$1,374.89 USD total for 5 nights

Oct 27 – Nov 1, 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)

$1,374.89 USD total for 5 nights

Oct 27 – Nov 1, 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 total for 5 nights

Oct 27 – Nov 1, 2026