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Holiday Rentals in Montgomery

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Bedrooms

Bathrooms

Amenities

Suitability

Property type

Distinctive Features

Distance from

5 km
50 rentals in Montgomery.
Log Cabin Chalet on 15 Private Acres, holiday rental in Montgomery
Log Cabin Chalet on 15 Private Acres, holiday rental in Montgomery
Log Cabin Chalet on 15 Private Acres, holiday rental in Montgomery

Log Cabin Chalet on 15 Private Acres

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Second floor, dog-friendly condo with modern decor and lovely views, holiday rental in Montgomery
Second floor, dog-friendly condo with modern decor and lovely views, holiday rental in Montgomery
Second floor, dog-friendly condo with modern decor and lovely views, holiday rental in Montgomery

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

Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Beautiful Mountain Cabin, holiday rental in Montgomery
Beautiful Mountain Cabin, holiday rental in Montgomery
Beautiful Mountain Cabin, holiday rental in Montgomery

Beautiful Mountain Cabin

Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Basil Brook: Colonial-Chic House - Mins to Jay Peak!, holiday rental in Montgomery
Basil Brook: Colonial-Chic House - Mins to Jay Peak!, holiday rental in Montgomery
Basil Brook: Colonial-Chic House - Mins to Jay Peak!, holiday rental in Montgomery

Basil Brook: Colonial-Chic House - Mins to Jay Peak!

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Log cabin condo with mountain views and full kitchen - close to Jay Peak Resort, holiday rental in Montgomery
Log cabin condo with mountain views and full kitchen - close to Jay Peak Resort, holiday rental in Montgomery
Log cabin condo with mountain views and full kitchen - close to Jay Peak Resort, holiday rental in Montgomery

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

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Cozy apartment with fantastic views 5 miles from Jay Peak, holiday rental in Montgomery
Cozy apartment with fantastic views 5 miles from Jay Peak, holiday rental in Montgomery
Cozy apartment with fantastic views 5 miles from Jay Peak, holiday rental in Montgomery

Cozy apartment with fantastic views 5 miles from Jay Peak

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Riverfront house walking distance to town with fireplace and w/d - dogs welcome, holiday rental in Montgomery
Riverfront house walking distance to town with fireplace and w/d - dogs welcome, holiday rental in Montgomery
Riverfront house walking distance to town with fireplace and w/d - dogs welcome, holiday rental in Montgomery

Riverfront house walking distance to town with fireplace and w/d - dogs welcome

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 10
Match: Sleeps
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Upscale Montgomery Cabin, Near Jay Peak Resort!, holiday rental in Montgomery
Upscale Montgomery Cabin, Near Jay Peak Resort!, holiday rental in Montgomery
Upscale Montgomery Cabin, Near Jay Peak Resort!, holiday rental in Montgomery

Upscale Montgomery Cabin, Near Jay Peak Resort!

Holiday Rental House
4 bedrooms
1 bathroom
Sleeps 7
Match: Sleeps
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Dog-friendly, riverfront home w/ full kitchen, patio, fireplace, & firepit, holiday rental in Montgomery
Dog-friendly, riverfront home w/ full kitchen, patio, fireplace, & firepit, holiday rental in Montgomery
Dog-friendly, riverfront home w/ full kitchen, patio, fireplace, & firepit, holiday rental in Montgomery

Dog-friendly, riverfront home w/ full kitchen, patio, fireplace, & firepit

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Stay near Jay Peak at your own private cabin with 18 brookside acres!, holiday rental in Montgomery
Stay near Jay Peak at your own private cabin with 18 brookside acres!, holiday rental in Montgomery
Stay near Jay Peak at your own private cabin with 18 brookside acres!, holiday rental in Montgomery

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

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Rustic Vermont Farm Home Near Jay Peak, holiday rental in Montgomery
Rustic Vermont Farm Home Near Jay Peak, holiday rental in Montgomery
Rustic Vermont Farm Home Near Jay Peak, holiday rental in Montgomery

Rustic Vermont Farm Home Near Jay Peak

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Contemporary cabin retreat minutes from Jay Peak Resort, holiday rental in Montgomery
Contemporary cabin retreat minutes from Jay Peak Resort, holiday rental in Montgomery
Contemporary cabin retreat minutes from Jay Peak Resort, holiday rental in Montgomery

Contemporary cabin retreat minutes from Jay Peak Resort

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 3
Match: Sleeps
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Rustic Swiss Chalet - Minutes from Jay PEAK, holiday rental in Montgomery
Rustic Swiss Chalet - Minutes from Jay PEAK, holiday rental in Montgomery
Rustic Swiss Chalet - Minutes from Jay PEAK, holiday rental in Montgomery

Rustic Swiss Chalet - Minutes from Jay PEAK

Holiday Rental House
6 bedrooms
3 bathrooms
Sleeps 14
Match: Sleeps
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The following properties within 32 kms of Montgomery match all your filters:
Beautiful 2-BR Ski-in, Ski-out Village Condo at Jay Peak, right on the slopes!, holiday rental in Montgomery
Beautiful 2-BR Ski-in, Ski-out Village Condo at Jay Peak, right on the slopes!, holiday rental in Montgomery
Beautiful 2-BR Ski-in, Ski-out Village Condo at Jay Peak, right on the slopes!, holiday rental in Montgomery

Beautiful 2-BR Ski-in, Ski-out Village Condo at Jay Peak, right on the slopes!

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Beautiful ski-in, ski-out 2-BR Village Condo at Jay Peak, right on the trail!, holiday rental in Montgomery
Beautiful ski-in, ski-out 2-BR Village Condo at Jay Peak, right on the trail!, holiday rental in Montgomery
Beautiful ski-in, ski-out 2-BR Village Condo at Jay Peak, right on the trail!, holiday rental in Montgomery

Beautiful ski-in, ski-out 2-BR Village Condo at Jay Peak, right on the trail!

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Edelweiss Alpine Retreat: A Luxurious 5 Bed Ski Chalet near Jay Peak, Vermont, holiday rental in Montgomery
Edelweiss Alpine Retreat: A Luxurious 5 Bed Ski Chalet near Jay Peak, Vermont, holiday rental in Montgomery
Edelweiss Alpine Retreat: A Luxurious 5 Bed Ski Chalet near Jay Peak, Vermont, holiday rental in Montgomery

Edelweiss Alpine Retreat: A Luxurious 5 Bed Ski Chalet near Jay Peak, Vermont

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 11
Match: Sleeps
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Ski-in/ski-out townhome with great views & deluxe resort amenities, holiday rental in Montgomery
Ski-in/ski-out townhome with great views & deluxe resort amenities, holiday rental in Montgomery
Ski-in/ski-out townhome with great views & deluxe resort amenities, holiday rental in Montgomery

Ski-in/ski-out townhome with great views & deluxe resort amenities

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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2 Bedroom Suite, holiday rental in Montgomery
2 Bedroom Suite, holiday rental in Montgomery
2 Bedroom Suite, holiday rental in Montgomery

2 Bedroom Suite

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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4 Bedroom Slopeside Townhouse -  6 Ski passes included each day!!, holiday rental in Montgomery
4 Bedroom Slopeside Townhouse -  6 Ski passes included each day!!, holiday rental in Montgomery
4 Bedroom Slopeside Townhouse -  6 Ski passes included each day!!, holiday rental in Montgomery

4 Bedroom Slopeside Townhouse - 6 Ski passes included each day!!

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Vrbo Property, holiday rental in Montgomery
Vrbo Property, holiday rental in Montgomery
Vrbo Property, holiday rental in Montgomery

Vrbo Property

Condo/Apartment
3 bedrooms
3 bathrooms
Sleeps 14
Match: Sleeps
More info
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Private Home w/ Hot Tub Near Jay Peak Slopes, holiday rental in Montgomery
Private Home w/ Hot Tub Near Jay Peak Slopes, holiday rental in Montgomery
Private Home w/ Hot Tub Near Jay Peak Slopes, holiday rental in Montgomery

Private Home w/ Hot Tub Near Jay Peak Slopes

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
More info
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Jay Peak Ski-in Ski-out Condo at Slopeside, holiday rental in Montgomery
Jay Peak Ski-in Ski-out Condo at Slopeside, holiday rental in Montgomery
Jay Peak Ski-in Ski-out Condo at Slopeside, holiday rental in Montgomery

Jay Peak Ski-in Ski-out Condo at Slopeside

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
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Jay Peak Ski-In/Ski-Out 2BR Upgraded Condo - Great Family Getaway, holiday rental in Montgomery
Jay Peak Ski-In/Ski-Out 2BR Upgraded Condo - Great Family Getaway, holiday rental in Montgomery
Jay Peak Ski-In/Ski-Out 2BR Upgraded Condo - Great Family Getaway, holiday rental in Montgomery

Jay Peak Ski-In/Ski-Out 2BR Upgraded Condo - Great Family Getaway

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Inviting Ski-in/Ski-out Condo at Jay Peak Resort!, holiday rental in Montgomery
Inviting Ski-in/Ski-out Condo at Jay Peak Resort!, holiday rental in Montgomery
Inviting Ski-in/Ski-out Condo at Jay Peak Resort!, holiday rental in Montgomery

Inviting Ski-in/Ski-out Condo at Jay Peak Resort!

Condo/Apartment
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
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Jay Peak, Luxury 5 BR Ski-in Ski-Out with Hot tub, holiday rental in Montgomery
Jay Peak, Luxury 5 BR Ski-in Ski-Out with Hot tub, holiday rental in Montgomery
Jay Peak, Luxury 5 BR Ski-in Ski-Out with Hot tub, holiday rental in Montgomery

Jay Peak, Luxury 5 BR Ski-in Ski-Out with Hot tub

Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
More info
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Charming cottage by Jay Peak, holiday rental in Montgomery
Charming cottage by Jay Peak, holiday rental in Montgomery
Charming cottage by Jay Peak, holiday rental in Montgomery

Charming cottage by Jay Peak

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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True Ski-in Ski-out! Walk to hotel-waterpark-golf, holiday rental in Montgomery
True Ski-in Ski-out! Walk to hotel-waterpark-golf, holiday rental in Montgomery
True Ski-in Ski-out! Walk to hotel-waterpark-golf, holiday rental in Montgomery

True Ski-in Ski-out! Walk to hotel-waterpark-golf

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
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Private Log Cabin Chalet in the Mountains, holiday rental in Montgomery
Private Log Cabin Chalet in the Mountains, holiday rental in Montgomery
Private Log Cabin Chalet in the Mountains, holiday rental in Montgomery

Private Log Cabin Chalet in the Mountains

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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Payment Protection
Absolute Slopeside Condo  Private Entrance, holiday rental in Montgomery
Absolute Slopeside Condo  Private Entrance, holiday rental in Montgomery
Absolute Slopeside Condo  Private Entrance, holiday rental in Montgomery

Absolute Slopeside Condo Private Entrance

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
More info
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Jay Peak's Premier Ski-In / Ski-Out Location-just steps from the trail, holiday rental in Montgomery
Jay Peak's Premier Ski-In / Ski-Out Location-just steps from the trail, holiday rental in Montgomery
Jay Peak's Premier Ski-In / Ski-Out Location-just steps from the trail, holiday rental in Montgomery

Jay Peak's Premier Ski-In / Ski-Out Location-just steps from the trail

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 7
Match: Sleeps
More info
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Ski in//Ski out 2 Bedroom Directly on Grammy Jay Run, holiday rental in Montgomery
Ski in//Ski out 2 Bedroom Directly on Grammy Jay Run, holiday rental in Montgomery
Ski in//Ski out 2 Bedroom Directly on Grammy Jay Run, holiday rental in Montgomery

Ski in//Ski out 2 Bedroom Directly on Grammy Jay Run

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Jay Peak 3 miles - ski here via Big Jay!, holiday rental in Montgomery
Jay Peak 3 miles - ski here via Big Jay!, holiday rental in Montgomery
Jay Peak 3 miles - ski here via Big Jay!, holiday rental in Montgomery

Jay Peak 3 miles - ski here via Big Jay!

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
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Jay Peak 3 mi - secluded with spectacular view!, holiday rental in Montgomery
Jay Peak 3 mi - secluded with spectacular view!, holiday rental in Montgomery
Jay Peak 3 mi - secluded with spectacular view!, holiday rental in Montgomery

Jay Peak 3 mi - secluded with spectacular view!

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
More info
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Beautiful, Sunny Jay Peak Ski-in/Ski-out Condo, holiday rental in Montgomery
Beautiful, Sunny Jay Peak Ski-in/Ski-out Condo, holiday rental in Montgomery
Beautiful, Sunny Jay Peak Ski-in/Ski-out Condo, holiday rental in Montgomery

Beautiful, Sunny Jay Peak Ski-in/Ski-out Condo

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Raspberry Cottage Retreat , mountain views and 15 minutes from Jay Peak Resort, holiday rental in Montgomery
Raspberry Cottage Retreat , mountain views and 15 minutes from Jay Peak Resort, holiday rental in Montgomery
Raspberry Cottage Retreat , mountain views and 15 minutes from Jay Peak Resort, holiday rental in Montgomery

Raspberry Cottage Retreat , mountain views and 15 minutes from Jay Peak Resort

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Jay Peak ski house mins to the mountain in quaint Vermont village, holiday rental in Montgomery
Jay Peak ski house mins to the mountain in quaint Vermont village, holiday rental in Montgomery
Jay Peak ski house mins to the mountain in quaint Vermont village, holiday rental in Montgomery

Jay Peak ski house mins to the mountain in quaint Vermont village

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 10
Match: Sleeps
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Beautiful Jay Peak Ski-in/Ski-out with hot tub!, holiday rental in Montgomery
Beautiful Jay Peak Ski-in/Ski-out with hot tub!, holiday rental in Montgomery
Beautiful Jay Peak Ski-in/Ski-out with hot tub!, holiday rental in Montgomery

Beautiful Jay Peak Ski-in/Ski-out with hot tub!

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Beautiful Chalet at Jay Peak for Aug/Sept/Oct/Nov, holiday rental in Montgomery
Beautiful Chalet at Jay Peak for Aug/Sept/Oct/Nov, holiday rental in Montgomery
Beautiful Chalet at Jay Peak for Aug/Sept/Oct/Nov, holiday rental in Montgomery

Beautiful Chalet at Jay Peak for Aug/Sept/Oct/Nov

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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3 bedroom townhouse at Jay Peak, Vermont (prime ski-on / ski-off location), holiday rental in Montgomery
3 bedroom townhouse at Jay Peak, Vermont (prime ski-on / ski-off location), holiday rental in Montgomery
3 bedroom townhouse at Jay Peak, Vermont (prime ski-on / ski-off location), holiday rental in Montgomery

3 bedroom townhouse at Jay Peak, Vermont (prime ski-on / ski-off location)

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Jay Peak - Ski-in / Ski-Out at the Best in the East, holiday rental in Montgomery
Jay Peak - Ski-in / Ski-Out at the Best in the East, holiday rental in Montgomery
Jay Peak - Ski-in / Ski-Out at the Best in the East, holiday rental in Montgomery

Jay Peak - Ski-in / Ski-Out at the Best in the East

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Fabulous ski in/ski out 2 bedroom condo, steps away from Grammy Jay trail!, holiday rental in Montgomery
Fabulous ski in/ski out 2 bedroom condo, steps away from Grammy Jay trail!, holiday rental in Montgomery
Fabulous ski in/ski out 2 bedroom condo, steps away from Grammy Jay trail!, holiday rental in Montgomery

Fabulous ski in/ski out 2 bedroom condo, steps away from Grammy Jay trail!

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Beautiful, Large 3 bdrm Jay Peak Ski-in/Ski-out Condo, holiday rental in Montgomery
Beautiful, Large 3 bdrm Jay Peak Ski-in/Ski-out Condo, holiday rental in Montgomery
Beautiful, Large 3 bdrm Jay Peak Ski-in/Ski-out Condo, holiday rental in Montgomery

Beautiful, Large 3 bdrm Jay Peak Ski-in/Ski-out Condo

Condo/Apartment
3 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
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★Jay Peak Mountain Chalet★secluded/pool/snowsports, holiday rental in Montgomery
★Jay Peak Mountain Chalet★secluded/pool/snowsports, holiday rental in Montgomery
★Jay Peak Mountain Chalet★secluded/pool/snowsports, holiday rental in Montgomery

★Jay Peak Mountain Chalet★secluded/pool/snowsports

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Luxury Family Chalet with views of Jay Peak, 3 miles from Jay Peak Resort, holiday rental in Montgomery
Luxury Family Chalet with views of Jay Peak, 3 miles from Jay Peak Resort, holiday rental in Montgomery
Luxury Family Chalet with views of Jay Peak, 3 miles from Jay Peak Resort, holiday rental in Montgomery

Luxury Family Chalet with views of Jay Peak, 3 miles from Jay Peak Resort

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Circa 1850s fully renovated Vermont farmhouse less than 15 miles from Jay Peak, holiday rental in Montgomery
Circa 1850s fully renovated Vermont farmhouse less than 15 miles from Jay Peak, holiday rental in Montgomery
Circa 1850s fully renovated Vermont farmhouse less than 15 miles from Jay Peak, holiday rental in Montgomery

Circa 1850s fully renovated Vermont farmhouse less than 15 miles from Jay Peak

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Jay Peak Ski-in/out Townhome, holiday rental in Montgomery
Jay Peak Ski-in/out Townhome, holiday rental in Montgomery
Jay Peak Ski-in/out Townhome, holiday rental in Montgomery

Jay Peak Ski-in/out Townhome

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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Ski-in, Ski-out Vacation Condo at Jay, holiday rental in Montgomery
Ski-in, Ski-out Vacation Condo at Jay, holiday rental in Montgomery
Ski-in, Ski-out Vacation Condo at Jay, holiday rental in Montgomery

Ski-in, Ski-out Vacation Condo at Jay

Condo/Apartment
4 bedrooms
4 bathrooms
Sleeps 14
Match: Sleeps
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Beautiful 4bd Condo w/ hot tub!, holiday rental in Montgomery
Beautiful 4bd Condo w/ hot tub!, holiday rental in Montgomery
Beautiful 4bd Condo w/ hot tub!, holiday rental in Montgomery

Beautiful 4bd Condo w/ hot tub!

Condo/Apartment
4 bedrooms
4 bathrooms
Sleeps 13
Match: Sleeps
More info
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Jay Peak Resort - Luxury ski-in/ski-out 5-bedroom, 4 bath townhouse, holiday rental in Montgomery
Jay Peak Resort - Luxury ski-in/ski-out 5-bedroom, 4 bath townhouse, holiday rental in Montgomery
Jay Peak Resort - Luxury ski-in/ski-out 5-bedroom, 4 bath townhouse, holiday rental in Montgomery

Jay Peak Resort - Luxury ski-in/ski-out 5-bedroom, 4 bath townhouse

Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 14
Match: Sleeps
More info
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Ski-in/Ski-out Jay Peak Resort South Village 125 Trailside, holiday rental in Montgomery
Ski-in/Ski-out Jay Peak Resort South Village 125 Trailside, holiday rental in Montgomery
Ski-in/Ski-out Jay Peak Resort South Village 125 Trailside, holiday rental in Montgomery

Ski-in/Ski-out Jay Peak Resort South Village 125 Trailside

Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 14
Match: Sleeps
More info
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Showing results 1-50 of 50
Frequently Asked Questions about Montgomery