Windham Vacation Rentals

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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
3 Guides
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89 reviews
$500 - $800 / night (excl. fees & taxes)
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Hearthstone Retreat - Luxurious 3BR/3BA Condo in Stratton, VT
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3 Bedrooms
3 Bathrooms
3 Guides
4.8IconIconIconIconIcon
5 reviews
$300 - $1770 / night (excl. fees & taxes)
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Village Watch Lux Loft
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Steps away from lifts and the village

4 Bedrooms
3 Bathrooms
3 Guides
$500 - $2666 / night (excl. fees & taxes)
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Village Watch Wonderland
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3 Bedrooms
2 Bathrooms
3 Guides
4.75IconIconIconIconIcon
8 reviews
$400 - $2292 / night (excl. fees & taxes)
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Stratton Slopeside Haven
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2 Bedrooms
3 Bathrooms
3 Guides
4.86IconIconIconIconIcon
7 reviews
$199 - $895 / night (excl. fees & taxes)
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Mt Snow/Stratton VT Getaway! w/Hot Tub + Game Room
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Mt Snow/Stratton VT Getaway! w/Hot Tub + Game Room

5 Bedrooms
3 Bathrooms
3 Guides
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24 reviews
$288 - $1014 / 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
3 Guides
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8 reviews
$262 - $1182 / night (excl. fees & taxes)
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The Little Matterhorn
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3 Bedrooms
2 Bathrooms
3 Guides
4.87IconIconIconIconIcon
30 reviews
$174 - $763 / night (excl. fees & taxes)
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Cozy Bromley Retreat
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1 Bedroom
1 Bathroom
3 Guides
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1 review
$93 - $448 / 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
3 Guides
4.61IconIconIconIconIcon
28 reviews
$205 / night (excl. fees & taxes)
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Perfect Mountain escape: your Stratton Family Cabin
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3 Bedrooms
4 Bathrooms
3 Guides
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8 reviews
$315 - $1278 / night (excl. fees & taxes)
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Perfect Mountain Getaway
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3 Bedrooms
2 Bathrooms
3 Guides
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14 reviews
$148 - $682 / night (excl. fees & taxes)
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Rural Chester Farmhouse
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3 Bedroom Farmhouse in Chester

3 Bedrooms
2 Bathrooms
3 Guides
$128 - $479 / night (excl. fees & taxes)
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HYGGE HOUSE Green Mountain Villa - Sauna Treehouse
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Located 8-12 minutes from MT SNOW and STRATTON MOUNTAIN and 1 mi from Green Mountain National Forest. Ski, Hike, Paddle, Snowshoe, Cycle

4 Bedrooms
2 Bathrooms
3 Guides
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84 reviews
$250 - $1418 / night (excl. fees & taxes)
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River Views with pool table and more!
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Luxurious Home w/ View of the CT River

5 Bedrooms
3 Bathrooms
3 Guides
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Trailside Chalet
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Walk to Okemo Ski Lift - Private Classic VT Ski Chalet w/ Fire Pit & Pool Table

5 Bedrooms
2 Bathrooms
3 Guides
4.9IconIconIconIconIcon
59 reviews
$250 - $2000 / night (excl. fees & taxes)
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Hillside Haven
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Hillside Haven Victorian! Hot Tub Firepit 5m-Okemo

5 Bedrooms
3 Bathrooms
3 Guides
$298 - $1545 / night (excl. fees & taxes)
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Clocktower Chalet
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*January 50% Discount* Walk to Okemo Lodge & Lifts. Private Home with Hot Tub

4 Bedrooms
2 Bathrooms
3 Guides
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31 reviews
$275 - $2000 / night (excl. fees & taxes)
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Manchester Santuary II
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Why stay in a room, when you can rent an entire home!

4 Bedrooms
4½ Bathrooms
3 Guides
$650 / night (excl. fees & taxes)
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Manchester Sanctuary
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Why stay in a room, when you can rent an entire home!

3 Bedrooms
3½ Bathrooms
3 Guides
$450 / night (excl. fees & taxes)
    21 – 40 Rentals