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Vacation rentals in Londonderry, Vermont, United States

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 3 274,27 $ USD total pour 3 nuits

26–29 oct. 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!

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

Glen Rd Mountain Retreat

3 bedrooms·2 baths

Peru • Vermont

1 259,66 $ USD total pour 3 nuits

26–29 oct. 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

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)

1 555,99 $ USD 1 355,94 $ USD total pour 3 nuits

26–29 oct. 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)

1 412,84 $ USD total pour 3 nuits

7–10 nov. 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

2 013,20 $ USD total pour 3 nuits

31 oct. – 3 nov. 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 pour 5 nuits

26–31 oct. 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

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 pour 3 nuits

26–29 oct. 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 pour 3 nuits

26–29 oct. 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 pour 3 nuits

26–29 oct. 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)

824,91 $ USD total pour 3 nuits

2–5 nov. 2026

Casita Bacon

4 bedrooms·4 baths

Winhall • Vermont

1 006,87 $ USD total pour 3 nuits

26–29 oct. 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 pour 3 nuits

26–29 oct. 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)

1 150,79 $ USD total pour 3 nuits

26–29 oct. 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)

Drop Point Cabin 15minutes to Stratton

Drop Point Cabin 15minutes to Stratton

4 bedrooms·3 baths

Jamaica • Vermont

988,84 $ USD total pour 3 nuits

26–29 oct. 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)

Snowfall Retreat

Snowfall Retreat

Snowfall Retreat

Snowfall Retreat

Snowfall Retreat

Snowfall Retreat

3 bedrooms·3 baths

Winhall • Vermont

1 055,54 $ USD total pour 3 nuits

26–29 oct. 2026

Snowdrift

4 bedrooms·3 baths

Winhall • Vermont

4.71(7 reviews)

1 064,30 $ USD total pour 3 nuits

26–29 oct. 2026

The Bears Den

4 bedrooms·3 baths

Winhall • Vermont

4.5(2 reviews)

1 400,66 $ USD total pour 3 nuits

26–29 oct. 2026