Location

Dates

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Vacation rentals in Brattleboro, Vermont, United States

The Bears Den

4 bedrooms·3 baths

Winhall • Vermont

4.5(2 reviews)

$ 1.529,49 USD totaal voor 3 nachten

1–4 okt 2026

Tranquil Treetop Retreat

Tranquil Treetop Retreat

Tranquil Treetop Retreat

Tranquil Treetop Retreat

Tranquil Treetop Retreat

4 bedrooms·4 baths

Winhall • Vermont

4.75(16 reviews)

$ 1.838,68 USD totaal voor 3 nachten

1–4 okt 2026

Stratton Slopeside Retreat

Stratton Slopeside Retreat

Stratton Slopeside Retreat

Stratton Slopeside Retreat

Stratton Slopeside Retreat

Stratton Slopeside Retreat

2 bedrooms·2 baths

Winhall • Vermont

5(3 reviews)

$ 1.195,97 USD totaal voor 3 nachten

1–4 okt 2026

Stratton Slopeside Haven

Stratton Slopeside Haven

Stratton Slopeside Haven

Stratton Slopeside Haven

Stratton Slopeside Haven

Stratton Slopeside Haven

2 bedrooms·3 baths

Winhall • Vermont

4.86(7 reviews)

$ 1.078,58 USD totaal voor 3 nachten

1–4 okt 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)

$ 1.505,69 USD totaal voor 3 nachten

1–4 okt 2026

Village Watch Wonderland Ski on Ski off + Steps to Stratton Village

Village Watch Wonderland Ski on Ski off + Steps to Stratton Village

Village Watch Wonderland Ski on Ski off + Steps to Stratton Village

Village Watch Wonderland Ski on Ski off + Steps to Stratton Village

Village Watch Wonderland Ski on Ski off + Steps to Stratton Village

Village Watch Wonderland Ski on Ski off + Steps to Stratton Village

3 bedrooms·2 baths

Winhall • Vermont

4.75(8 reviews)

$ 1.749,48 USD totaal voor 3 nachten

1–4 okt 2026

Village Watch Lux Loft

Village Watch Lux Loft

Village Watch Lux Loft

Village Watch Lux Loft

Village Watch Lux Loft

Village Watch Lux Loft

4 bedrooms·3 baths

Winhall • Vermont

$ 2.095,16 USD totaal voor 3 nachten

1–4 okt 2026

The warm and inviting living room has direct access to the patio with a view of the pond and fountain.
The gas fireplace operates with the simple turn of a timer switch.

Heated year-round, the beautiful pool, hot tubs and sauna are just steps from Rising Bear Lodge.

Beautiful architecture and design inside and out.

Luxury Condo*Walk to Ski Lifts*Hot Tub*Pool*Sauna!

Luxury Condo*Walk to Ski Lifts*Hot Tub*Pool*Sauna!

Luxury CondoWalk to Ski LiftsHot TubPoolSauna!

2 bedrooms·2 baths

Winhall • Vermont

5(89 reviews)

$ 2.525,55 USD totaal voor 3 nachten

1–4 okt 2026

Hearthstone Retreat - Luxurious 3BR/3BA Condo in Stratton, VT

Hearthstone Retreat - Luxurious 3BR/3BA Condo in Stratton, VT

Hearthstone Retreat - Luxurious 3BR/3BA Condo in Stratton, VT

Hearthstone Retreat - Luxurious 3BR/3BA Condo in Stratton, VT

Hearthstone Retreat - Luxurious 3BR/3BA Condo in Stratton, VT

Hearthstone Retreat - Luxurious 3BR/3BA Condo in Stratton, VT

3 bedrooms·3 baths

Winhall • Vermont

4.8(5 reviews)

$ 3.086,82 USD totaal voor 3 nachten

1–4 okt 2026

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 totaal voor 3 nachten

1–4 okt 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

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 totaal voor 5 nachten

1–6 okt 2026

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

Londonderry Links

Londonderry Links

Londonderry Links

Londonderry Links

Londonderry Links

Londonderry Links

3 bedrooms·2 baths

Londonderry • Vermont

4.88(25 reviews)

$ 980,84 USD totaal voor 3 nachten

1–4 aug 2027

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)

Casita Bacon

4 bedrooms·4 baths

Winhall • Vermont

$ 1.379,99 USD totaal voor 3 nachten

1–4 okt 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)

$ 993,00 USD totaal voor 3 nachten

1–4 okt 2026