Location

Dates

Guests

Vacation rentals in Wilmington, Vermont, United States

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)

8827,87 $ USD total por 3 noites

24/09/2026 – 27/09/2026

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)

Snowdrift

4 bedrooms·3 baths

Winhall • Vermont

4.71(7 reviews)

1369,36 $ USD total por 3 noites

24/09/2026 – 27/09/2026

The Bears Den

4 bedrooms·3 baths

Winhall • Vermont

4.5(2 reviews)

1423,75 $ USD total por 3 noites

24/09/2026 – 27/09/2026

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)

1350,12 $ USD total por 3 noites

24/09/2026 – 27/09/2026

Front yard and house

Guard rails have been added both sides of stairs since this picture was taken.

Looking up toward loft area with partial view of kitchen lower right. Note the spiral staircase.

Cozy converted barn on secluded 6.5 acres

3 bedrooms·1 bath

Shaftsbury • Vermont

5(390 reviews)

899,80 $ USD 809,08 $ USD total por 3 noites

26/10/2026 – 29/10/2026

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

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

1505,44 $ USD total por 3 noites

28/09/2026 – 01/10/2026

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

$650/ noite(excl. taxas & impostos)

Casita Bacon

4 bedrooms·4 baths

Winhall • Vermont

1145,43 $ USD total por 3 noites

28/09/2026 – 01/10/2026

The Deming House

The Deming House

The Deming House

The Deming House

The Deming House

The Deming House

3 bedrooms·4 baths

Arlington • Vermont

4(1 review)

The Azimuth

5 bedrooms·2 baths

Sunderland • Vermont

1170,95 $ USD total por 3 noites

27/09/2026 – 30/09/2026

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)

941,00 $ USD total por 3 noites

24/09/2026 – 27/09/2026

HUGE private Mansion! 15 bedroom, 12 bath sleep 34

HUGE private Mansion! 15 bedroom, 12 bath sleep 34

HUGE private Mansion! 15 bedroom, 12 bath sleep 34

HUGE private Mansion! 15 bedroom, 12 bath sleep 34

HUGE private Mansion! 15 bedroom, 12 bath sleep 34

HUGE private Mansion! 15 bedroom, 12 bath sleep 34

15 bedrooms·1 bath

Manchester • Vermont

5(17 reviews)

$3240/ noite(excl. taxas & impostos)

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)

1042,94 $ USD total por 3 noites

27/09/2026 – 30/09/2026

Shadow Peak Chalet

Shadow Peak Chalet

Shadow Peak Chalet

Shadow Peak Chalet

Shadow Peak Chalet

Shadow Peak Chalet

4 bedrooms·2 baths

Manchester • Vermont

1161,22 $ USD total por 3 noites

24/09/2026 – 27/09/2026

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)

Londonderry Links

Londonderry Links

Londonderry Links

Londonderry Links

Londonderry Links

Londonderry Links

3 bedrooms·2 baths

Londonderry • Vermont

4.88(25 reviews)

$200/ noite(excl. taxas & impostos)

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)

954,96 $ USD total por 3 noites

24/09/2026 – 27/09/2026

The Riverside Treehouse

The Riverside Treehouse

The Riverside Treehouse

The Riverside Treehouse

The Riverside Treehouse

The Riverside Treehouse

3 bedrooms·2 baths

Arlington • Vermont

5(4 reviews)

904,27 $ USD total por 3 noites

28/09/2026 – 01/10/2026

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

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)

711,43 $ USD total por 3 noites

30/09/2026 – 03/10/2026

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)

$205/ noite(excl. taxas & impostos)

the view of the front of the home with the wrap around deck!

This is the view of the rear of the home

the access ramp

entry to the home at the rear.

Enter via the mudroom and please remove your shoes!

Manchester Santuary II

4 bedrooms·4½ baths

Manchester • Vermont

5(1 review)

2264,50 $ USD total por 3 noites

24/09/2026 – 27/09/2026