Montgomery, Vermont

Vacation Rentals in Montgomery, Vermont

Discover 12 vacation rental properties in Montgomery. From 2 to 6 bedrooms. Average $277/night. 100% have pools.

12 verified listings Book securely on VRBO Prices updated March 2026

12 properties available

Experience the rustic charm of a log cabin chalet nestled on 14 private acres.

Experience the rustic charm of a log cabin chalet nestled on 14 private acres.

3 beds 2 baths
PoolA/CWiFiBalcony
$254/night
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Beautiful Mountain Cabin near Jay Peak Resort!

Beautiful Mountain Cabin near Jay Peak Resort!

2 beds 2 baths
PoolA/CWiFiBalcony
$271/night
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Cozy apartment that’s conveniently located just on the edge of town.

Cozy apartment that’s conveniently located just on the edge of town.

2 beds 1 bath
PoolA/CWiFiBalcony
$151/night
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Inviting riverfront home with patio & fireplace, near skiing & golf

Inviting riverfront home with patio & fireplace, near skiing & golf

3 beds 1 bath
PoolA/CWiFiBalcony
$179/night
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Second floor, dog-friendly condo with modern decor and lovely views

Second floor, dog-friendly condo with modern decor and lovely views

3 beds 2 baths
PoolA/CWiFiBalcony
$179/night
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Basil Brook: Colonial-Chic House - near Jay Peak!

Basil Brook: Colonial-Chic House - near Jay Peak!

3 beds 2 baths
PoolA/CWiFiBalcony
$456/night
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Log cabin condo with mountain views and full kitchen - close to Jay Peak Resort

Log cabin condo with mountain views and full kitchen - close to Jay Peak Resort

2 beds 1 bath
PoolA/CWiFiBalcony
$171/night
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15 min to Jay Peak

15 min to Jay Peak

3 beds 1 bath
PoolA/CWiFiBalcony
$245/night
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Rustic Vermont Barn Home Near Jay Peak w/Pizza Oven

Rustic Vermont Barn Home Near Jay Peak w/Pizza Oven

3 beds 2 baths
PoolA/CWiFiBalcony
$255/night
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Upscale Montgomery Cabin, Near Jay Peak Resort!

Upscale Montgomery Cabin, Near Jay Peak Resort!

4 beds 1 bath
PoolA/CWiFiBalcony
$381/night
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Stay near Jay Peak at your own private cabin with 18 brookside acres!

Stay near Jay Peak at your own private cabin with 18 brookside acres!

3 beds 2 baths
PoolA/CWiFiBalcony
$339/night
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Rustic Swiss Chalet - Minutes from Jay PEAK

Rustic Swiss Chalet - Minutes from Jay PEAK

6 beds 3 baths
PoolA/CWiFiBalcony
$441/night
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