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Montgomery Holiday Apartments

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50 rentals in Montgomery.
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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
3 bathrooms
Sleeps 10
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The Perfect Vermont Modern Victorian, holiday rental in Montgomery
The Perfect Vermont Modern Victorian, holiday rental in Montgomery
The Perfect Vermont Modern Victorian, holiday rental in Montgomery

The Perfect Vermont Modern Victorian

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 10
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NEW! Secluded Upscale Cabin - Near Jay Peak Resort, holiday rental in Montgomery
NEW! Secluded Upscale Cabin - Near Jay Peak Resort, holiday rental in Montgomery
NEW! Secluded Upscale Cabin - Near Jay Peak Resort, holiday rental in Montgomery

NEW! Secluded Upscale 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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Farmhouse in the mountains, easy drive to Jay Peak, holiday rental in Montgomery
Farmhouse in the mountains, easy drive to Jay Peak, holiday rental in Montgomery
Farmhouse in the mountains, easy drive to Jay Peak, holiday rental in Montgomery

Farmhouse in the mountains, easy drive to Jay Peak

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 7
Match: Sleeps
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Farmhouse, outdoor kitchen, surrounded in mountain views, close to Jay Peak, holiday rental in Montgomery
Farmhouse, outdoor kitchen, surrounded in mountain views, close to Jay Peak, holiday rental in Montgomery
Farmhouse, outdoor kitchen, surrounded in mountain views, close to Jay Peak, holiday rental in Montgomery

Farmhouse, outdoor kitchen, surrounded in mountain views, close to Jay Peak

Holiday Rental House
4 bedrooms
1 bathroom
Sleeps 6
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 5
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
4 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Beautiful Log Cabin Chalet on 15 Wooded Acres in the Mountains, holiday rental in Montgomery
Beautiful Log Cabin Chalet on 15 Wooded Acres in the Mountains, holiday rental in Montgomery
Beautiful Log Cabin Chalet on 15 Wooded Acres in the Mountains, holiday rental in Montgomery

Beautiful Log Cabin Chalet on 15 Wooded Acres in the Mountains

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Serene Mountain Cabin on 25 Acres with Private Pond, holiday rental in Montgomery
Serene Mountain Cabin on 25 Acres with Private Pond, holiday rental in Montgomery
Serene Mountain Cabin on 25 Acres with Private Pond, holiday rental in Montgomery

Serene Mountain Cabin on 25 Acres with Private Pond

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
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New Construction Home!, holiday rental in Montgomery
New Construction Home!, holiday rental in Montgomery
New Construction Home!, holiday rental in Montgomery

New Construction Home!

Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 12
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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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
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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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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
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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
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Ski In Trailside Condo - Steps away from WaterPark & Ice Rink, holiday rental in Montgomery
Ski In Trailside Condo - Steps away from WaterPark & Ice Rink, holiday rental in Montgomery
Ski In Trailside Condo - Steps away from WaterPark & Ice Rink, holiday rental in Montgomery

Ski In Trailside Condo - Steps away from WaterPark & Ice Rink

Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Comfy Ski-In/Ski-Out Hideaway in Jay Peak Resort!, holiday rental in Montgomery
Comfy Ski-In/Ski-Out Hideaway in Jay Peak Resort!, holiday rental in Montgomery
Comfy Ski-In/Ski-Out Hideaway in Jay Peak Resort!, holiday rental in Montgomery

Comfy Ski-In/Ski-Out Hideaway in Jay Peak Resort!

Condo/Apartment
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Ski-In Resort Family Condo w/ Deck at Jay Peak!, holiday rental in Montgomery
Ski-In Resort Family Condo w/ Deck at Jay Peak!, holiday rental in Montgomery
Ski-In Resort Family Condo w/ Deck at Jay Peak!, holiday rental in Montgomery

Ski-In Resort Family Condo w/ Deck at Jay Peak!

Condo/Apartment
4 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Ski-in/ski-out townhome w/ great views & deluxe, resort amenities, holiday rental in Montgomery
Ski-in/ski-out townhome w/ great views & deluxe, resort amenities, holiday rental in Montgomery
Ski-in/ski-out townhome w/ great views & deluxe, resort amenities, holiday rental in Montgomery

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

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Ski-in/Ski-out Luxury Condo at Jay Peak Resort!, holiday rental in Montgomery
Ski-in/Ski-out Luxury Condo at Jay Peak Resort!, holiday rental in Montgomery
Ski-in/Ski-out Luxury Condo at Jay Peak Resort!, holiday rental in Montgomery

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

Condo/Apartment
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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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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2 Bedroom Suite With Room For 6

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Ski-in/Ski-out Village Condo with Two 2 BR/2 BA Connecting Units!

Condo/Apartment
4 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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Ski in Ski Out Jay Peak Luxury Two Bedroom Apartment, holiday rental in Montgomery
Ski in Ski Out Jay Peak Luxury Two Bedroom Apartment, holiday rental in Montgomery
Ski in Ski Out Jay Peak Luxury Two Bedroom Apartment, holiday rental in Montgomery

Ski in Ski Out Jay Peak Luxury Two Bedroom Apartment

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Ski-in ski-out, 3 floor deluxe Townhouse at Jay Peak Resort, holiday rental in Montgomery
Ski-in ski-out, 3 floor deluxe Townhouse at Jay Peak Resort, holiday rental in Montgomery
Ski-in ski-out, 3 floor deluxe Townhouse at Jay Peak Resort, holiday rental in Montgomery

Ski-in ski-out, 3 floor deluxe Townhouse at Jay Peak Resort

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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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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Ski-in/ski-out Jay Peak Resort condo near water park, ice skating, & hiking!, holiday rental in Montgomery
Ski-in/ski-out Jay Peak Resort condo near water park, ice skating, & hiking!, holiday rental in Montgomery
Ski-in/ski-out Jay Peak Resort condo near water park, ice skating, & hiking!, holiday rental in Montgomery

Ski-in/ski-out Jay Peak Resort condo near water park, ice skating, & hiking!

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Unit #1 on the Trout River **PET FRIENDLY ��, holiday rental in Montgomery
Unit #1 on the Trout River **PET FRIENDLY ��, holiday rental in Montgomery
Unit #1 on the Trout River **PET FRIENDLY ��, holiday rental in Montgomery

Unit #1 on the Trout River **PET FRIENDLY ��

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Jay Peak 3 miles - hike, mountain bike & waterpark!, holiday rental in Montgomery
Jay Peak 3 miles - hike, mountain bike & waterpark!, holiday rental in Montgomery
Jay Peak 3 miles - hike, mountain bike & waterpark!, holiday rental in Montgomery

Jay Peak 3 miles - hike, mountain bike & waterpark!

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
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Stylish ski-in/out getaway w/easy access to trails, golf, & downhill runs, holiday rental in Montgomery
Stylish ski-in/out getaway w/easy access to trails, golf, & downhill runs, holiday rental in Montgomery
Stylish ski-in/out getaway w/easy access to trails, golf, & downhill runs, holiday rental in Montgomery

Stylish ski-in/out getaway w/easy access to trails, golf, & downhill runs

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Unit #2 on the Trout River ** PET FRIENDLY! ��, holiday rental in Montgomery
Unit #2 on the Trout River ** PET FRIENDLY! ��, holiday rental in Montgomery
Unit #2 on the Trout River ** PET FRIENDLY! ��, holiday rental in Montgomery

Unit #2 on the Trout River ** PET FRIENDLY! ��

Holiday Rental House
1 bedroom
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
5 bedrooms
1 bathroom
Sleeps 10
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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Ski-in/ski-out condo with access to water park, fitness room, golf, & much more!, holiday rental in Montgomery
Ski-in/ski-out condo with access to water park, fitness room, golf, & much more!, holiday rental in Montgomery
Ski-in/ski-out condo with access to water park, fitness room, golf, & much more!, holiday rental in Montgomery

Ski-in/ski-out condo with access to water park, fitness room, golf, & much more!

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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New listing! Walk to lifts, Pump House Waterpark, golf course & much more!, holiday rental in Montgomery
New listing! Walk to lifts, Pump House Waterpark, golf course & much more!, holiday rental in Montgomery
New listing! Walk to lifts, Pump House Waterpark, golf course & much more!, holiday rental in Montgomery

New listing! Walk to lifts, Pump House Waterpark, golf course & much more!

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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New listing! Walk to the ski lifts, water park, golf course & more!, holiday rental in Montgomery
New listing! Walk to the ski lifts, water park, golf course & more!, holiday rental in Montgomery
New listing! Walk to the ski lifts, water park, golf course & more!, holiday rental in Montgomery

New listing! Walk to the ski lifts, water park, golf course & more!

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
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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Private Riverfront Oasis near Jay Peak Resort, holiday rental in Montgomery
Private Riverfront Oasis near Jay Peak Resort, holiday rental in Montgomery
Private Riverfront Oasis near Jay Peak Resort, holiday rental in Montgomery

Private Riverfront Oasis near Jay Peak Resort

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 11
Match: Sleeps
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Ski in Ski Out  2 bedroom condo at Jay Peak Resort, holiday rental in Montgomery
Ski in Ski Out  2 bedroom condo at Jay Peak Resort, holiday rental in Montgomery
Ski in Ski Out  2 bedroom condo at Jay Peak Resort, holiday rental in Montgomery

Ski in Ski Out 2 bedroom condo at Jay Peak Resort

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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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
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Jay Peak 3 Bedroom Trailside Condo directly on the mountain., holiday rental in Montgomery
Jay Peak 3 Bedroom Trailside Condo directly on the mountain., holiday rental in Montgomery
Jay Peak 3 Bedroom Trailside Condo directly on the mountain., holiday rental in Montgomery

Jay Peak 3 Bedroom Trailside Condo directly on the mountain.

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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NEW! Ski In, Ski Out Escape: Steps to Jay Trail!, holiday rental in Montgomery
NEW! Ski In, Ski Out Escape: Steps to Jay Trail!, holiday rental in Montgomery
NEW! Ski In, Ski Out Escape: Steps to Jay Trail!, holiday rental in Montgomery

NEW! Ski In, Ski Out Escape: Steps to Jay Trail!

Condo/Apartment
2 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
5 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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First Tracks Jay Peak Ski-in Ski-out Condo, holiday rental in Montgomery
First Tracks Jay Peak Ski-in Ski-out Condo, holiday rental in Montgomery
First Tracks Jay Peak Ski-in Ski-out Condo, holiday rental in Montgomery

First Tracks Jay Peak Ski-in Ski-out Condo

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Unit #3 on the Trout River **Pet Friendly**, holiday rental in Montgomery
Unit #3 on the Trout River **Pet Friendly**, holiday rental in Montgomery
Unit #3 on the Trout River **Pet Friendly**, holiday rental in Montgomery

Unit #3 on the Trout River **Pet Friendly**

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Jay Peak 3mi - hike, mountain bike & waterpark!, holiday rental in Montgomery
Jay Peak 3mi - hike, mountain bike & waterpark!, holiday rental in Montgomery
Jay Peak 3mi - hike, mountain bike & waterpark!, holiday rental in Montgomery

Jay Peak 3mi - hike, mountain bike & waterpark!

Condo/Apartment
3 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
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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
3 bedrooms
1 bathroom
Sleeps 7
Match: Sleeps
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Ski Chalet, holiday rental in Montgomery
Ski Chalet, holiday rental in Montgomery
Ski Chalet, holiday rental in Montgomery

Ski Chalet

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 4
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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