Vacation Rentals & House Rentals in Chester

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Wireless Internet
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Parking
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32 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

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

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

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

Beautiful Country Luxury Waterfront Lake Home

Unity cottage

3 bedrooms
2 bathrooms

sleeps 13

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Price per night from

$981

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 Country Lake House

Ludlow house

4 bedrooms
3 bathrooms

sleeps 8

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Price per night from

$287

3 Season Cabin - sleeping porch lake trails

Mount Holly log cabin

3 bedrooms
1 bathroom

sleeps 8

Responds fast! avg. 1 hour 58 minutes

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Price per night from

$103

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

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

Cozy Historic Hilltop Cottage

Brownsville house

2 bedrooms
1 bathroom

sleeps 4

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Price per night from

$212

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

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

Perfect Hideaway Cabin - lake, trails, forest, meadows

Mount Holly log cabin

1 bedroom
1 bathroom

sleeps 4

Responds fast! avg. 1 hour 58 minutes

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Price per night from

$103

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

Vermont Cottage Lake Amherst

Plymouth cottage

5 bedrooms
4 bathrooms

sleeps 10

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Price per night from

$802

1820 House

Perkinsville house

4 bedrooms
2 bathrooms

sleeps 10

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Price per night from

$344

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

Multi Level Stratton Mountain Retreat

Bondville house

6 bedrooms
5 bathrooms

sleeps 16

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Price per night from

$1,145

The Grafton Lodge

Grafton lodge

7 bedrooms
4 bathrooms

sleeps 20

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Price per night from

$2,176

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

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Chester Rentals

Per night

32 Houses

Hugging Bear Inn RENT ENTIRE INN

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

2 Bedroom/2 Bath Condo

Whispers of the North

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

Beautiful Country Luxury Waterfront Lake Home

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 Country Lake House

3 Season Cabin - sleeping porch lake trails

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

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

Cozy Historic Hilltop Cottage

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

Vermont 1828 Reunion House, sleeps 16 5 miles to Okemo

Lakefront vacation home - 4 BR - sleeps 10

Perfect Hideaway Cabin - lake, trails, forest, meadows

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

Cute VT Bungalow With 180 Degree View of NH

Vermont Cottage Lake Amherst

1820 House

Vermont Cottage on Lake Amherst 6 Bedrooms 4 Bathrooms

Multi Level Stratton Mountain Retreat

The Grafton Lodge

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

Viewing 32 of 32
rentals in Chester

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Chester Rentals

Per night

32 Houses

Viewing 32 of 32rentals in Chester

Also consider

Viewing 32 of 32
rentals in Chester