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Montgomery Vacation Rentals

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50 rentals in Montgomery.
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Rustic Vermont Farm Home Near Jay Peak, vacation rental in Montgomery
Rustic Vermont Farm Home Near Jay Peak, vacation rental in Montgomery
Rustic Vermont Farm Home Near Jay Peak, vacation rental in Montgomery

Rustic Vermont Farm Home Near Jay Peak

Rental Home
3 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Private Log Home - �Friendly, Get Away from it all, vacation rental in Montgomery
Private Log Home - �Friendly, Get Away from it all, vacation rental in Montgomery
Private Log Home - �Friendly, Get Away from it all, vacation rental in Montgomery

Private Log Home - �Friendly, Get Away from it all

Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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The Perfect Vermont Modern Victorian, vacation rental in Montgomery
The Perfect Vermont Modern Victorian, vacation rental in Montgomery
The Perfect Vermont Modern Victorian, vacation rental in Montgomery

The Perfect Vermont Modern Victorian

Rental Home
5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Secluded Upscale Cabin - Near Jay Peak Resort, vacation rental in Montgomery
Secluded Upscale Cabin - Near Jay Peak Resort, vacation rental in Montgomery
Secluded Upscale Cabin - Near Jay Peak Resort, vacation rental in Montgomery

Secluded Upscale Cabin - Near Jay Peak Resort

Rental Home
4 bedrooms
1 bathroom
Sleeps 7
Match: Sleeps
More info
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Dog-friendly, riverfront home w/ full kitchen, patio, fireplace, & firepit, vacation rental in Montgomery
Dog-friendly, riverfront home w/ full kitchen, patio, fireplace, & firepit, vacation rental in Montgomery
Dog-friendly, riverfront home w/ full kitchen, patio, fireplace, & firepit, vacation rental in Montgomery

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

Rental Home
3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Farmhouse, outdoor kitchen, surrounded in mountain views, close to Jay Peak, vacation rental in Montgomery
Farmhouse, outdoor kitchen, surrounded in mountain views, close to Jay Peak, vacation rental in Montgomery
Farmhouse, outdoor kitchen, surrounded in mountain views, close to Jay Peak, vacation rental in Montgomery

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

Rental Home
4 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Farmhouse, MTN views, vacation rental in Montgomery
Farmhouse, MTN views, vacation rental in Montgomery
Farmhouse, MTN views, vacation rental in Montgomery

Farmhouse, MTN views

Rental Home
3 bedrooms
1 bathroom
Sleeps 7
Match: Sleeps
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Cozy apartment with fantastic views 5 miles from Jay Peak, vacation rental in Montgomery
Cozy apartment with fantastic views 5 miles from Jay Peak, vacation rental in Montgomery
Cozy apartment with fantastic views 5 miles from Jay Peak, vacation rental in Montgomery

Cozy apartment with fantastic views 5 miles from Jay Peak

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
More info
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Beautiful ski-in, ski-out 2-BR Village Condo at Jay Peak, right on the trail!, vacation rental in Montgomery
Beautiful ski-in, ski-out 2-BR Village Condo at Jay Peak, right on the trail!, vacation rental in Montgomery
Beautiful ski-in, ski-out 2-BR Village Condo at Jay Peak, right on the trail!, vacation 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
More info
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Jay Peak Ski-In/Ski-Out 2BR Upgraded Condo - Great Family Getaway, vacation rental in Montgomery
Jay Peak Ski-In/Ski-Out 2BR Upgraded Condo - Great Family Getaway, vacation rental in Montgomery
Jay Peak Ski-In/Ski-Out 2BR Upgraded Condo - Great Family Getaway, vacation 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!

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Jay Peak, Luxury 5 BR Ski-in Ski-Out with Hot tub, vacation rental in Montgomery
Jay Peak, Luxury 5 BR Ski-in Ski-Out with Hot tub, vacation rental in Montgomery
Jay Peak, Luxury 5 BR Ski-in Ski-Out with Hot tub, vacation rental in Montgomery

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

Rental Home
5 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
More info
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Jay Peak - Ski-in / Ski-Out at the Best in the East, vacation rental in Montgomery
Jay Peak - Ski-in / Ski-Out at the Best in the East, vacation rental in Montgomery
Jay Peak - Ski-in / Ski-Out at the Best in the East, vacation 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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Ski In Trailside Condo - Steps away from WaterPark & Ice Rink Discount Lift Tix, vacation rental in Montgomery
Ski In Trailside Condo - Steps away from WaterPark & Ice Rink Discount Lift Tix, vacation rental in Montgomery
Ski In Trailside Condo - Steps away from WaterPark & Ice Rink Discount Lift Tix, vacation rental in Montgomery

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

Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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Warm&Cozy Ski-In/Ski-Out Condo in Jay Peak Resort!, vacation rental in Montgomery
Warm&Cozy Ski-In/Ski-Out Condo in Jay Peak Resort!, vacation rental in Montgomery
Warm&Cozy Ski-In/Ski-Out Condo in Jay Peak Resort!, vacation rental in Montgomery

Warm&Cozy Ski-In/Ski-Out Condo in Jay Peak Resort!

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

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

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

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

Rental Home
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
More info
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Ski-in/Ski-out Luxury Condo at Jay Peak Resort!, vacation rental in Montgomery
Ski-in/Ski-out Luxury Condo at Jay Peak Resort!, vacation rental in Montgomery
Ski-in/Ski-out Luxury Condo at Jay Peak Resort!, vacation rental in Montgomery

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

Condo/Apartment
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
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Enjoy the HOT TUB after a day on the slopes of the best resort in the east, vacation rental in Montgomery
Enjoy the HOT TUB after a day on the slopes of the best resort in the east, vacation rental in Montgomery
Enjoy the HOT TUB after a day on the slopes of the best resort in the east, vacation rental in Montgomery

Enjoy the HOT TUB after a day on the slopes of the best resort in the east

Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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Charming Cottage by Jay Peak, vacation rental in Montgomery
Charming Cottage by Jay Peak, vacation rental in Montgomery
Charming Cottage by Jay Peak, vacation rental in Montgomery

Charming Cottage by Jay Peak

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Log Cabin - One Mile From Jay Peak Resort, vacation rental in Montgomery
Log Cabin - One Mile From Jay Peak Resort, vacation rental in Montgomery
Log Cabin - One Mile From Jay Peak Resort, vacation rental in Montgomery

Log Cabin - One Mile From Jay Peak Resort

Rental Home
4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
More info
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2 Bedroom Suite With Room For 6

Rental Home
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
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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
More info
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Modern, Ideal Location, Family Friendly!, vacation rental in Montgomery
Modern, Ideal Location, Family Friendly!, vacation rental in Montgomery
Modern, Ideal Location, Family Friendly!, vacation rental in Montgomery

Modern, Ideal Location, Family Friendly!

Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
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Ski in Ski Out Jay Peak Luxury 2 Bedroom Condo, vacation rental in Montgomery
Ski in Ski Out Jay Peak Luxury 2 Bedroom Condo, vacation rental in Montgomery
Ski in Ski Out Jay Peak Luxury 2 Bedroom Condo, vacation rental in Montgomery

Ski in Ski Out Jay Peak Luxury 2 Bedroom Condo

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Four Bedroom Log Cabin -Jay Peak - Views - Private - Fireplace -, vacation rental in Montgomery
Four Bedroom Log Cabin -Jay Peak - Views - Private - Fireplace -, vacation rental in Montgomery
Four Bedroom Log Cabin -Jay Peak - Views - Private - Fireplace -, vacation rental in Montgomery

Four Bedroom Log Cabin -Jay Peak - Views - Private - Fireplace -

Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
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Ski-in ski-out, 3 floor deluxe Townhouse at Jay Peak Resort, vacation rental in Montgomery
Ski-in ski-out, 3 floor deluxe Townhouse at Jay Peak Resort, vacation rental in Montgomery
Ski-in ski-out, 3 floor deluxe Townhouse at Jay Peak Resort, vacation rental in Montgomery

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

Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
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Fabulous ski-in/ski out 2 bedroom condo, steps away from Grammy Jay trail!, vacation rental in Montgomery
Fabulous ski-in/ski out 2 bedroom condo, steps away from Grammy Jay trail!, vacation rental in Montgomery
Fabulous ski-in/ski out 2 bedroom condo, steps away from Grammy Jay trail!, vacation 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
More info
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Ski-in/ski-out Jay Peak Resort condo near water park, ice skating, & hiking!, vacation rental in Montgomery
Ski-in/ski-out Jay Peak Resort condo near water park, ice skating, & hiking!, vacation rental in Montgomery
Ski-in/ski-out Jay Peak Resort condo near water park, ice skating, & hiking!, vacation rental in Montgomery

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

Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
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Gorgeous, secluded home w/private balcony, deck, ski lockers, & free WiFi!, vacation rental in Montgomery
Gorgeous, secluded home w/private balcony, deck, ski lockers, & free WiFi!, vacation rental in Montgomery
Gorgeous, secluded home w/private balcony, deck, ski lockers, & free WiFi!, vacation rental in Montgomery

Gorgeous, secluded home w/private balcony, deck, ski lockers, & free WiFi!

Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
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Jay Peak 3 miles, Big Jay, Catamount & Long trails from your door!, vacation rental in Montgomery
Jay Peak 3 miles, Big Jay, Catamount & Long trails from your door!, vacation rental in Montgomery
Jay Peak 3 miles, Big Jay, Catamount & Long trails from your door!, vacation rental in Montgomery

Jay Peak 3 miles, Big Jay, Catamount & Long trails from your door!

Rental Home
2 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
More info
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Stylish ski-in/out getaway w/easy access to trails, golf, & downhill runs, vacation rental in Montgomery
Stylish ski-in/out getaway w/easy access to trails, golf, & downhill runs, vacation rental in Montgomery
Stylish ski-in/out getaway w/easy access to trails, golf, & downhill runs, vacation 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
More info
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ALWAYS PET FRIENDLY! ��, vacation rental in Montgomery
ALWAYS PET FRIENDLY! ��, vacation rental in Montgomery
ALWAYS PET FRIENDLY! ��, vacation rental in Montgomery

ALWAYS PET FRIENDLY! ��

Rental Home
1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
More info
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Relaxation in the mountains. Hike, Ski & explore around Jay Peak, vacation rental in Montgomery
Relaxation in the mountains. Hike, Ski & explore around Jay Peak, vacation rental in Montgomery
Relaxation in the mountains. Hike, Ski & explore around Jay Peak, vacation rental in Montgomery

Relaxation in the mountains. Hike, Ski & explore around Jay Peak

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
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4 bedroom, 2 bath, large finished basement 2.4 miles to Jay Peak Resort!, vacation rental in Montgomery
4 bedroom, 2 bath, large finished basement 2.4 miles to Jay Peak Resort!, vacation rental in Montgomery
4 bedroom, 2 bath, large finished basement 2.4 miles to Jay Peak Resort!, vacation rental in Montgomery

4 bedroom, 2 bath, large finished basement 2.4 miles to Jay Peak Resort!

Rental Home
4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
More info
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Riverfront Cottage-Pet Friendly, vacation rental in Montgomery
Riverfront Cottage-Pet Friendly, vacation rental in Montgomery
Riverfront Cottage-Pet Friendly, vacation rental in Montgomery

Riverfront Cottage-Pet Friendly

Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Jay Peak Resort - Luxury ski-In/ski-out - 5 bedroom, 4 bath end unit townhouse, vacation rental in Montgomery
Jay Peak Resort - Luxury ski-In/ski-out - 5 bedroom, 4 bath end unit townhouse, vacation rental in Montgomery
Jay Peak Resort - Luxury ski-In/ski-out - 5 bedroom, 4 bath end unit townhouse, vacation rental in Montgomery

Jay Peak Resort - Luxury ski-In/ski-out - 5 bedroom, 4 bath end unit townhouse

Rental Home
5 bedrooms
4 bathrooms
Sleeps 11
Match: Sleeps
More info
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Ski-in/ski-out condo with access to water park, fitness room, golf, & much more!, vacation rental in Montgomery
Ski-in/ski-out condo with access to water park, fitness room, golf, & much more!, vacation rental in Montgomery
Ski-in/ski-out condo with access to water park, fitness room, golf, & much more!, vacation 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
More info
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Bright, family-friendly condo w/ a full kitchen & balcony - near the slopes!, vacation rental in Montgomery
Bright, family-friendly condo w/ a full kitchen & balcony - near the slopes!, vacation rental in Montgomery
Bright, family-friendly condo w/ a full kitchen & balcony - near the slopes!, vacation rental in Montgomery

Bright, family-friendly condo w/ a full kitchen & balcony - near the slopes!

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
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New! Luxury 5 bedroom- on mountain!, vacation rental in Montgomery
New! Luxury 5 bedroom- on mountain!, vacation rental in Montgomery
New! Luxury 5 bedroom- on mountain!, vacation rental in Montgomery

New! Luxury 5 bedroom- on mountain!

Condo/Apartment
5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
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New listing! Walk to lifts, Pump House Waterpark, golf course & much more!, vacation rental in Montgomery
New listing! Walk to lifts, Pump House Waterpark, golf course & much more!, vacation rental in Montgomery
New listing! Walk to lifts, Pump House Waterpark, golf course & much more!, vacation 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
More info
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NEW! Cabin in the Untouched Woods, 3 Miles to Ski!, vacation rental in Montgomery
NEW! Cabin in the Untouched Woods, 3 Miles to Ski!, vacation rental in Montgomery
NEW! Cabin in the Untouched Woods, 3 Miles to Ski!, vacation rental in Montgomery

NEW! Cabin in the Untouched Woods, 3 Miles to Ski!

Rental Home
1 bedroom
1 bathroom
Sleeps 8
Match: Sleeps
More info
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Quaint old farmhouse, vacation rental in Montgomery
Quaint old farmhouse, vacation rental in Montgomery
Quaint old farmhouse, vacation rental in Montgomery

Quaint old farmhouse

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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New listing! Walk to the ski lifts, water park, golf course & more!, vacation rental in Montgomery
New listing! Walk to the ski lifts, water park, golf course & more!, vacation rental in Montgomery
New listing! Walk to the ski lifts, water park, golf course & more!, vacation 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
More info
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Tentrr Signature Site - Missisquoi Magic, vacation rental in Montgomery
Tentrr Signature Site - Missisquoi Magic, vacation rental in Montgomery
Tentrr Signature Site - Missisquoi Magic, vacation rental in Montgomery

Tentrr Signature Site - Missisquoi Magic

Rental Home
0 bedrooms
1 bathroom
Sleeps 12
Match: Sleeps
More info
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Luxury Family Chalet with views of Jay Peak (3 miles from Jay Peak Resort), vacation rental in Montgomery
Luxury Family Chalet with views of Jay Peak (3 miles from Jay Peak Resort), vacation rental in Montgomery
Luxury Family Chalet with views of Jay Peak (3 miles from Jay Peak Resort), vacation rental in Montgomery

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

Rental Home
4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
More info
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Private Riverfront Oasis near Jay Peak Resort, vacation rental in Montgomery
Private Riverfront Oasis near Jay Peak Resort, vacation rental in Montgomery
Private Riverfront Oasis near Jay Peak Resort, vacation rental in Montgomery

Private Riverfront Oasis near Jay Peak Resort

Rental Home
3 bedrooms
1 bathroom
Sleeps 11
Match: Sleeps
More info
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New listing! Two neighboring condos - walk to lifts, water park & golf course!, vacation rental in Montgomery
New listing! Two neighboring condos - walk to lifts, water park & golf course!, vacation rental in Montgomery
New listing! Two neighboring condos - walk to lifts, water park & golf course!, vacation rental in Montgomery

New listing! Two neighboring condos - walk to lifts, water park & golf course!

Condo/Apartment
4 bedrooms
4 bathrooms
Sleeps 11
Match: Sleeps
More info
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Ski in Ski Out  2 bedroom condo at Jay Peak Resort, vacation rental in Montgomery
Ski in Ski Out  2 bedroom condo at Jay Peak Resort, vacation rental in Montgomery
Ski in Ski Out  2 bedroom condo at Jay Peak Resort, vacation rental in Montgomery

Ski in Ski Out 2 bedroom condo at Jay Peak Resort

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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Private Log Cabin Chalet in the Mountains

Rental Home
0 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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