Jamaica, Vermont

Vacation Rentals in Jamaica, Vermont

Discover 13 vacation rental properties in Jamaica. From 1 to 5 bedrooms. Average $321/night. 100% have pools.

13 verified listings Book securely on VRBO Prices updated March 2026

13 properties available

Beautiful Lakefront Home is located in Woods on Cole Pond. Near Stratton

Beautiful Lakefront Home is located in Woods on Cole Pond. Near Stratton

4 beds 2 baths
PoolA/CWiFiBalcony
$502/night
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Scandinavian Sauna near hiking and views

Scandinavian Sauna near hiking and views

3 beds 3 baths
PoolA/CWiFiBalcony
$183/night
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Cozy, inviting condo close to skiing, hiking, golf & charming villages

Cozy, inviting condo close to skiing, hiking, golf & charming villages

2 beds 1 bath
PoolA/CWiFiBalcony
$297/night
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Authentic and comfortable Vermont log cabin - secluded yet near attractions

Authentic and comfortable Vermont log cabin - secluded yet near attractions

4 beds 2 baths
PoolA/CWiFiBalcony
$227/night
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Cozy Country Chalet . Family friendly. Close to skiing, hiking, kayaking, golf

Cozy Country Chalet . Family friendly. Close to skiing, hiking, kayaking, golf

3 beds 2 baths
PoolA/CWiFiBalcony
$399/night
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Privacy in the Green Mountains! Hike, bike, swim and enjoy VT all summer.

Privacy in the Green Mountains! Hike, bike, swim and enjoy VT all summer.

4 beds 3 baths
PoolA/CWiFiBalcony
$213/night
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Plenty of Room For Everyone! - 5 Minutes to Stratton

Plenty of Room For Everyone! - 5 Minutes to Stratton

4 beds 4 baths
PoolA/CWiFiBalcony
$541/night
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Modern 5BR VT home minutes to Stratton w/ Sauna

Modern 5BR VT home minutes to Stratton w/ Sauna

5 beds 3 baths
PoolA/CWiFiBalcony
$704/night
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5 min drive to Stratton, 1 min to Pikes Falls, fire pit, electric fireplace!

5 min drive to Stratton, 1 min to Pikes Falls, fire pit, electric fireplace!

1 bed 1 bath
PoolA/CWiFiBalcony
$109/night
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Wishing Well Cabin

Wishing Well Cabin

3 beds 2 baths
PoolA/CWiFiBalcony
$284/night
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Jamaica Escape ~ 2 Mi to Stratton Mountain!

Jamaica Escape ~ 2 Mi to Stratton Mountain!

4 beds 3 baths
PoolA/CWiFiBalcony
$352/night
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Two Bedroom Chalet, Charming, Quiet, River Front

Two Bedroom Chalet, Charming, Quiet, River Front

2 beds 1 bath
PoolA/CWiFiBalcony
$203/night
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Starry Skies: 7min to SkiStratton+PikesFalls+DogOK

Starry Skies: 7min to SkiStratton+PikesFalls+DogOK

2 beds 2 baths
PoolA/CWiFiBalcony
$156/night
View Details → Book on VRBO

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