Vacation Rentals & House Rentals in Chester

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Pets
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Skiing – property near ski resort
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30 Houses

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Work, Hike, Ski, Relax - Big Restored 1860s Farmhouse

Chester house

5 bedrooms
4 bathrooms

sleeps 12

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Price per night from

$1,031

Great rentals within 20 miles that match your search

Modern Ski In / Ski Out 4BR / 3BA Smart Home w/ shared pool and hot tub

Bondville condo

4 bedrooms
3 bathrooms

sleeps 15

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Price per night from

$171

The Grafton Lodge

Grafton lodge

7 bedrooms
4 bathrooms

sleeps 20

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Price per night from

$2,176

Multi Level Stratton Mountain Retreat

Bondville house

6 bedrooms
5 bathrooms

sleeps 16

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Price per night from

$1,145

2 Bedroom/2 Bath Condo

Stratton Mountain apartment

2 bedrooms
2 bathrooms

sleeps 5

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Price per night from

$343

Whispers of the North

West Wardsboro house

6 bedrooms
3 bathrooms

sleeps 14

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Price per night from

$252

The "Okemo House" at Clocktower - WALK TO SKI TRAIL! Private Home w/ Hot Tub

Ludlow house

4 bedrooms
2 bathrooms

sleeps 12

“The Perfect Vermont Getaway” When I visit Vermont in winter, I tend to go with a mixed crowd. Part of our group are avid skiers/snowboarders, the other part (well, me) are not. This house allows you to experience the best of both worlds, with something for everyone. Situated on top of the mountain (within walking distance to the lodge and with a shuttle that can pick you up right outside the front door), it's in the absolute perfect location for those who like to lace up their boots and hit the slopes. For anyone not playing snow bunny for the day, you are smack dab in the middle of Okemo with plenty of cafes, shopping, and scenic walks just down the hillside (or a very short drive away if you wish to explore). The house itself is also a fantastic, light, open space that is comfortable no matter which straw you draw for beds (we got the twins in the upstairs loft and had one of the soundest sleeps I'd had all winter). Plus, who doesn't love a hot tub. You never feel cramped even with a full house. The living room is an amazing space to just sip coffee and read your book in the morning sunshine or in front of the fire. The owners are extremely knowledgeable, responsive, and helpful, and made sure our stay was top-notch. They have everything outlined for you in a book when you arrive and are there for you should you have any questions. I can't wait to go back next winter!

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Price per night from

$1,832

6 BR Ski Chalet with Boats in VT Green Mountains

Ludlow chalet

6 bedrooms
2 bathrooms

sleeps 12

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Price per night from

$373

Vermont Cottage on Lake Amherst 6 Bedrooms 4 Bathrooms

Plymouth cottage

5 bedrooms
4 bathrooms

sleeps 10

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Price per night from

$802

Vermont Country Lake House

Ludlow house

4 bedrooms
3 bathrooms

sleeps 8

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Price per night from

$287

Walk to ski trials on Okemo! Private Luxury Chalet

Ludlow chalet

5 bedrooms
3 bathrooms

sleeps 14

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Price per night from

$1,369

The "Okemo House" at Trailside - Walk to Okemo Ski Lifts! Private 5 bedroom home

Ludlow house

5 bedrooms
2 bathrooms

sleeps 13

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Price per night from

$1,374

Beautiful Okemo chalet with Hot Tub

Ludlow chalet

4 bedrooms
3 bathrooms

sleeps 16

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Price per night from

$373

Trail Side at Bromley Resort Minutes from Manchester VT, Stratton & Magic

Peru house

4 bedrooms
2 bathrooms

sleeps 12

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Price per night from

$401

Vermont Log Home On 21 Acres Btwn Okemo/killington

Mount Holly house

4 bedrooms
3 bathrooms

sleeps 14

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Price per night from

$430

Vermont Cottage Lake Amherst

Plymouth cottage

5 bedrooms
4 bathrooms

sleeps 10

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Price per night from

$802

Vermont 1828 Reunion House, sleeps 16 5 miles to Okemo

Proctorsville house

8 bedrooms
4 bathrooms

sleeps 16

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Price per night from

$458

South Face Village

Ludlow condo

2 bedrooms
3 bathrooms

sleeps 6

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Price per night from

$630

Oma"s Kottage

Ludlow house

6 bedrooms
2 bathrooms

sleeps 11

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Price per night from

$344

Village Farmhouse - mins to GMHA, Okemo, Killington. Pet-friendly.

Reading house

4 bedrooms
1 bathroom

sleeps 8

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Price per night from

$287

Spectacular 50 miles Year Round Mountain View - 3+ BR Townhouse

Peru townhouse

4 bedrooms
3 bathrooms

sleeps 8

Responds fast! avg. 2 hours 2 minutes

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Price per night from

$338

Lakefront vacation home - 4 BR - sleeps 10

Ludlow house

4 bedrooms
2 bathrooms

sleeps 10

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Price per night from

$401

Close to Okemo, 25 Acre Mtn Playground, 2 Bd, Great Ski Access, VAST trails

Ludlow condo

2 bedrooms
1 bathroom

sleeps 6

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Price per night from

$401

Stunning Designers VT Home Luxurious, 5600 SF, 3D Home Theater, Gourmet kitchen

Bondville villa

4 bedrooms
5 bathrooms

sleeps 10

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Price per night from

$1,123

Contemporary Ski Chalet Minutes to Hiking Dining Parks

South Londonderry house

3 bedrooms
2 bathrooms

sleeps 10

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Price per night from

$1,444

Cute VT Bungalow With 180 Degree View of NH

Springfield apartment

1 bedroom
1 bathroom

sleeps 2

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Price per night from

$229

1820 House

Perkinsville house

4 bedrooms
2 bathrooms

sleeps 10

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Price per night from

$344

The Whimsical Chalet

Mount Holly villa

3 bedrooms
2 bathrooms

sleeps 10

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Price per night from

$291

PennRock Lakeside

Ludlow house

4 bedrooms
2 bathrooms

sleeps 10

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Price per night from

$369

Treehouse

Ludlow house

6 bedrooms
3 bathrooms

sleeps 16

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Price per night from

$747

Also consider

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Chester Rentals

Per night

30 Houses

Work, Hike, Ski, Relax - Big Restored 1860s Farmhouse

Modern Ski In / Ski Out 4BR / 3BA Smart Home w/ shared pool and hot tub

The Grafton Lodge

Multi Level Stratton Mountain Retreat

2 Bedroom/2 Bath Condo

Whispers of the North

The "Okemo House" at Clocktower - WALK TO SKI TRAIL! Private Home w/ Hot Tub

6 BR Ski Chalet with Boats in VT Green Mountains

Vermont Cottage on Lake Amherst 6 Bedrooms 4 Bathrooms

Vermont Country Lake House

Walk to ski trials on Okemo! Private Luxury Chalet

The "Okemo House" at Trailside - Walk to Okemo Ski Lifts! Private 5 bedroom home

Beautiful Okemo chalet with Hot Tub

Trail Side at Bromley Resort Minutes from Manchester VT, Stratton & Magic

Vermont Log Home On 21 Acres Btwn Okemo/killington

Vermont Cottage Lake Amherst

Vermont 1828 Reunion House, sleeps 16 5 miles to Okemo

South Face Village

Oma"s Kottage

Village Farmhouse - mins to GMHA, Okemo, Killington. Pet-friendly.

Spectacular 50 miles Year Round Mountain View - 3+ BR Townhouse

Lakefront vacation home - 4 BR - sleeps 10

Close to Okemo, 25 Acre Mtn Playground, 2 Bd, Great Ski Access, VAST trails

Stunning Designers VT Home Luxurious, 5600 SF, 3D Home Theater, Gourmet kitchen

Contemporary Ski Chalet Minutes to Hiking Dining Parks

Cute VT Bungalow With 180 Degree View of NH

1820 House

The Whimsical Chalet

PennRock Lakeside

Treehouse

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rentals in Chester

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Chester Rentals

Per night

30 Houses

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rentals in Chester