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Vacation rentals in Chester, Vermont, United States

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Front lawn view

Vermont Cottage Amherst Lake & Sanctuary

Vermont Cottage Amherst Lake & Sanctuary

Vermont Cottage Amherst Lake & Sanctuary

Vermont Cottage Amherst Lake & Sanctuary

6 bedrooms·4 baths

Plymouth • Vermont

4.98(90 reviews)

$6,582.00 USD total for 6 nights

Sep 15 – 21, 2026

Twilight ~ CURRENTLY UPDATING PICTURES ~ STAY TUNED!

Historic Vermont Lake Cottage~Hot Tub~Dogs~Okemo

Historic Vermont Lake Cottage~Hot Tub~Dogs~Okemo

Historic Vermont Lake Cottage~Hot Tub~Dogs~Okemo

Historic Vermont Lake Cottage~Hot Tub~Dogs~Okemo

Historic Vermont Lake Cottage~Hot Tub~Dogs~Okemo

4 bedrooms·3 baths

Plymouth • Vermont

5(55 reviews)

$2,294.20 USD total for 3 nights

Sep 7 – 10, 2026

The front porch at dusk

Cute Cabin! Plymouth, Vermont.

Cute Cabin! Plymouth, Vermont.

Cute Cabin! Plymouth, Vermont.

Cute Cabin! Plymouth, Vermont.

3 bedrooms·3 baths

Plymouth • Vermont

5(52 reviews)

$2,031.00 USD total for 3 nights

Sep 8 – 11, 2026

Get-Away Cabin in Plymouth, Vermont.

Aerial view of Lake Amherst

Large screened-in porch overlooking the lake.

Get-Away Cabin in Plymouth, Vermont.

Get-Away Cabin in Plymouth, Vermont.

1 bedroom·2 baths

Plymouth • Vermont

5(34 reviews)

$1,107.00 USD total for 3 nights

Sep 7 – 10, 2026

1930s-era cottage.

Private outdoor hot tub under cover.

Outdoor fire pit

Primary bedroom with king bed. Featuring a Puffy mattress, fine linens, plenty of pillows, and a down comforter.

The living room opens up to a larger screened-in porch. Dining also on the porch. It features a wood-burning fireplace for cooler times. It will be all set to light and we provide plenty of wood.

Twinkle Cottage ~HotTub~FirePit~Fireplace~Dogs

1 bedroom·2 baths

Plymouth • Vermont

$1,191.00 USD total for 3 nights

Sep 7 – 10, 2026

Carriage House

2 bedrooms·2 baths

Mount Holly • Vermont

$927.00 USD total for 3 nights

Sep 7 – 10, 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)

$1,600.29 USD total for 3 nights

Sep 7 – 10, 2026

The Bears Den

4 bedrooms·3 baths

Winhall • Vermont

4.5(2 reviews)

$1,400.66 USD total for 3 nights

Sep 7 – 10, 2026

Casita Bacon

4 bedrooms·4 baths

Winhall • Vermont

$1,132.06 USD total for 3 nights

Sep 7 – 10, 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)

$912.00 USD total for 3 nights

Sep 7 – 10, 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)

$546.13 USD total for 3 nights

Sep 7 – 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)

$839.45 USD total for 3 nights

Sep 7 – 10, 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)

$934.30 USD total for 3 nights

Sep 8 – 11, 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/ night(excl. fees & taxes)

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

Sep 7 – 10, 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)

$2,186.55 USD total for 3 nights

Sep 12 – 15, 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)

$1,576.01 USD total for 3 nights

Sep 7 – 10, 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)

$934.65 USD total for 3 nights

Sep 7 – 10, 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)

$1,785.05 USD total for 3 nights

Sep 7 – 10, 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)

$1,197.69 USD total for 3 nights

Sep 7 – 10, 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

$1,596.84 USD total for 3 nights

Sep 7 – 10, 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)

$871.96 USD total for 3 nights

Sep 7 – 10, 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)

$8,825.61 USD total for 3 nights

Sep 7 – 10, 2026

Free cancellation