Chester Vacation Rentals

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Sauna with Green Mountain View’s
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Scandinavian Sauna near hiking and views

3 Bedrooms
3 Bathrooms
$194 - $672 / night (excl. fees & taxes)
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Mountain Oasis - Hot Tub, Sauna, Fire Pit, & MORE!
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5 Bedrooms
3 Bathrooms
$410 - $1831 / night (excl. fees & taxes)
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Ski Lodge Hideaway: 5 minutes to Stratton mountain
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4 Bedrooms
4 Bathrooms
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6 reviews
$225 - $901 / night (excl. fees & taxes)
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NirvanaSanctuaryHouse~Fire Place~Okemo Killington
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Nirvana Sanctuary House~Fire Place~Okemo Killington 2 BR 3BA

2 Bedrooms
3 Bathrooms
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31 reviews
$425 / night (excl. fees & taxes)
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Vermont Cottage~Lake & Sanctuary~Lake Amherst
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Vermont Cottage On Lake Amherst & Sanctuary ~ Pet Friendly ~ Fire Pit ~ Fire place ~ Between Okemo & Killington Areas ~ Route 100

6 Bedrooms
4 Bathrooms
4.98IconIconIconIconIcon
90 reviews
$800 - $900 / night (excl. fees & taxes)
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Forty Winks Cottage In Vermont
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3 BR~3BA~DogFriendly~FirePlace~HotTub~FirePit~Charming~Cozy~Unique~Vintage~Okemo~Killington

3 Bedrooms
3 Bathrooms
4.98IconIconIconIconIcon
52 reviews
$600 / night (excl. fees & taxes)
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Vermont Cottage Amherst Lake & Sanctuary
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LakeAmherstRentals~Good Woods Cottage~Okemo Killington~Dog Friendly~Hot Tub~Fire Pit~

4 Bedrooms
3 Bathrooms
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55 reviews
$650 / night (excl. fees & taxes)
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Cool Haven~Cute Cottage in Plymouth, Vermont.
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1 BR Cottage Fireplace~Lake Views~Hot Tub~Dog Freindly~Private

1 Bedroom
2 Bathrooms
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34 reviews
$350 / night (excl. fees & taxes)
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Twinkle Cottage ~HotTub~FirePit~Fireplace~Dogs
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Twinkle Cottage~HotTub~FirePit~Dogs~Volley Ball~Croquet~

1 Bedroom
2 Bathrooms
$350 / night (excl. fees & taxes)
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Stratton Hollow House
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4 Bedrooms
2 Bathrooms
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1 review
$300 - $1448 / night (excl. fees & taxes)
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Snowdrift
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Spacious getaway featuring a Barrel Sauna!

4 Bedrooms
3 Bathrooms
4.71IconIconIconIconIcon
7 reviews
$324 - $1413 / night (excl. fees & taxes)
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The Bears Den
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4 Bedrooms
3 Bathrooms
4.5IconIconIconIconIcon
2 reviews
$290 - $1264 / night (excl. fees & taxes)
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Stratton 4 BR condo*Hot Tub* Game Room* on Shuttle
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4 Bedroom, 3 bath* Direct Stratton Mountain Views* Private Hot Tub* Game Room* Sleeps 10! On shuttle route to Stratton, only 5 minutes away

4 Bedrooms
3 Bathrooms
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5 reviews
$375 / night (excl. fees & taxes)
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Cozy Bromley Retreat
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1 Bedroom
1 Bathroom
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1 review
$93 - $449 / night (excl. fees & taxes)
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Renovated 2BR on Bromley | Fall Foliage & Hiking
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Renovated 2BR on Bromley | Fall Foliage & Hiking

2 Bedrooms
1 Bathroom
4.61IconIconIconIconIcon
28 reviews
$205 / night (excl. fees & taxes)
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The Little Matterhorn
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3 Bedrooms
2 Bathrooms
4.87IconIconIconIconIcon
30 reviews
$170 - $752 / night (excl. fees & taxes)
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Mount Holly Lake & Ski Hideaway
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Mount Holly Lake & Ski Hideaway

4 Bedrooms
2 Bathrooms
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37 reviews
$299 / night (excl. fees & taxes)
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Stratton Chalet
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13 minutes to Stratton mountain, 6 minutes to bromley mountain. Featuring a hot tub

4 Bedrooms
5 Bathrooms
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8 reviews
$261 - $1169 / night (excl. fees & taxes)
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Luxury Condo*Walk to Ski Lifts*Hot Tub*Pool*Sauna!
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Luxury Condo*Walk to Ski Lifts*Hot Tub*Pool*Sauna!

2 Bedrooms
2 Bathrooms
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89 reviews
$500 - $800 / night (excl. fees & taxes)
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Tranquil Treetop Retreat
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4 Bedrooms
4 Bathrooms
4.75IconIconIconIconIcon
16 reviews
$250 - $1335 / night (excl. fees & taxes)
    21 – 40 Rentals