Vacation Rentals & House Rentals in Chester

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Beach or lakeside relaxation
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25 Houses

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Hugging Bear Inn RENT ENTIRE INN

Chester b&b

6 bedrooms
7 bathrooms

sleeps 18

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Price per night from

$1,231

Great rentals within 20 miles that match your search

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

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 Country Lake House

Ludlow house

4 bedrooms
3 bathrooms

sleeps 8

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Price per night from

$287

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

South Face Village

Ludlow condo

2 bedrooms
3 bathrooms

sleeps 6

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Price per night from

$630

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

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

Lakefront vacation home - 4 BR - sleeps 10

Ludlow house

4 bedrooms
2 bathrooms

sleeps 10

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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

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

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

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

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

Ludlow apartment

2 bedrooms
1 bathroom

sleeps 6

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Price per night from

$401

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

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

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 Cottage Lake Amherst

Plymouth cottage

5 bedrooms
4 bathrooms

sleeps 10

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Price per night from

$802

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

Treehouse

Ludlow house

6 bedrooms
3 bathrooms

sleeps 16

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Price per night from

$741

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Stowe 165 properties
Killington 64 properties
Ludlow 16 properties
Northeast Kingdom 14 properties
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Chester Rentals

Per night

25 Houses

Hugging Bear Inn RENT ENTIRE INN

2 Bedroom/2 Bath Condo

Whispers of the North

6 BR Ski Chalet with Boats in VT Green Mountains

Vermont Country Lake House

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

South Face Village

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

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

Vermont 1828 Reunion House, sleeps 16 5 miles to Okemo

Lakefront vacation home - 4 BR - sleeps 10

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

Cute VT Bungalow With 180 Degree View of NH

1820 House

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

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

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

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

Walk to ski trials on Okemo! Private Luxury Chalet

Vermont Cottage on Lake Amherst 6 Bedrooms 4 Bathrooms

Vermont Cottage Lake Amherst

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

Treehouse

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rentals in Chester

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Chester Rentals

Per night

25 Houses

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rentals in Chester