Vacation rentals in Montgomery, VT

Best vacation rentals and Airbnb offers in Montgomery, VT

Jay Peak Village Home 367B

Apartment, Montgomery

Jay Peak Village Home 367B is a apartment in Montgomery, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with…

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About Jay Peak Village Home 367B

Jay Peak Village Home 367B is a apartment in Montgomery, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: parking, paid parking, heating, non smoking::room, and non smoking rooms.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,204.

From$113/night

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Slopeside 705

Apartment, Montgomery

Slopeside 705 is a apartment in Montgomery, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or…

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About Slopeside 705

Slopeside 705 is a apartment in Montgomery, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free wifi, parking, paid parking, and heating.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,214.

From$120/night

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Grammy Jay Getaway #V363

Apartment, Montgomery

Grammy Jay Getaway #V363 is a apartment in Montgomery, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with…

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About Grammy Jay Getaway #V363

Grammy Jay Getaway #V363 is a apartment in Montgomery, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free wifi, gym, parking, and paid parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,427.

From$143/night

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

Apartment, Montgomery

Cozy apartment that’s conveniently located just on the edge of town. is a apartment in Montgomery, with kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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

Cozy apartment that’s conveniently located just on the edge of town. is a apartment in Montgomery, with kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, kitchen, with kitchen, tv, and heating.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,222.

From$175/night

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Vacation rentals with a pool in Montgomery, VT

Add a pool to the search when you want an easy place to cool off between outings.

Spacious 2-BR Ski-in, Ski-out Jay Peak Village Condo, right on trail. A/C incl!

Condo, Montgomery

Spacious 2-BR Ski-in, Ski-out Jay Peak Village Condo, right on trail. A/C incl! is a condo in Montgomery, with pool access, kitchen access, and room for a group. This stay gives travelers a…

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About Spacious 2-BR Ski-in, Ski-out Jay Peak Village Condo, right on trail. A/C incl!

Spacious 2-BR Ski-in, Ski-out Jay Peak Village Condo, right on trail. A/C incl! is a condo in Montgomery, with pool access, kitchen access, and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, free wifi, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,252.

From$179/night

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Spacious ski-in, ski-out 2-BR Jay Peak Village Condo, right on trail. A/C incl.!

Condo, Montgomery

Spacious ski-in, ski-out 2-BR Jay Peak Village Condo, right on trail. A/C incl.! is a condo in Montgomery, with pool access, kitchen access, and room for a group. This stay gives travelers…

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About Spacious ski-in, ski-out 2-BR Jay Peak Village Condo, right on trail. A/C incl.!

Spacious ski-in, ski-out 2-BR Jay Peak Village Condo, right on trail. A/C incl.! is a condo in Montgomery, with pool access, kitchen access, and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, free wifi, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,252.

From$179/night

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Ski in/out 4 BR townhome directly on Raccoon Run and the Village Chair Lift !!

Holiday Home, Montgomery

Ski in/out 4 BR townhome directly on Raccoon Run and the Village Chair Lift !! is a holiday home in Montgomery, with pool access, kitchen access, and room for a group. This stay gives…

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About Ski in/out 4 BR townhome directly on Raccoon Run and the Village Chair Lift !!

Ski in/out 4 BR townhome directly on Raccoon Run and the Village Chair Lift !! is a holiday home in Montgomery, with pool access, kitchen access, and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, free wifi, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,167.

From$310/night

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Best Ski In/Ski Out Location - ❄️❄️ Jay Peak Large 3 BR

Condo, Montgomery

Best Ski In/Ski Out Location - ❄️❄️ Jay Peak Large 3 BR is a condo in Montgomery, with pool access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring…

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About Best Ski In/Ski Out Location - ❄️❄️ Jay Peak Large 3 BR

Best Ski In/Ski Out Location - ❄️❄️ Jay Peak Large 3 BR is a condo in Montgomery, with pool access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: pool, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,614.

From$373/night

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Vacation rentals with parking in Montgomery, VT

Find vacation rentals that make arriving by car easier.

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

Apartment, Montgomery

Relaxation in the mountains. Hike, Ski & explore around Jay Peak is a apartment in Montgomery, with parking, kitchen access, and a quieter setting. This stay gives travelers a comfortable…

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

Relaxation in the mountains. Hike, Ski & explore around Jay Peak is a apartment in Montgomery, with parking, kitchen access, and a quieter setting. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $989.

From$141/night

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Jay Peak ski on-ski-off condo in the newest buildings directly on the mountain.

Condo, Montgomery

Jay Peak ski on-ski-off condo in the newest buildings directly on the mountain. is a condo in Montgomery, with parking and kitchen access. This stay gives travelers a comfortable base for…

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About Jay Peak ski on-ski-off condo in the newest buildings directly on the mountain.

Jay Peak ski on-ski-off condo in the newest buildings directly on the mountain. is a condo in Montgomery, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: kitchen, with kitchen, parking, free parking, and fireplace.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,263.

From$180/night

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Ski On/Off - Trailside Condo 5 Star Rating other platforms, newly listed on VRBO

Condo, Montgomery

Ski On/Off - Trailside Condo 5 Star Rating other platforms, newly listed on VRBO is a condo in Montgomery, with parking and kitchen access. This stay gives travelers a comfortable base for…

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About Ski On/Off - Trailside Condo 5 Star Rating other platforms, newly listed on VRBO

Ski On/Off - Trailside Condo 5 Star Rating other platforms, newly listed on VRBO is a condo in Montgomery, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,278.

From$183/night

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

Country House, Montgomery

Jay Peak ski house mins to the mountain in quaint Vermont village is a country house in Montgomery, with parking and kitchen access. This stay gives travelers a comfortable base for…

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

Jay Peak ski house mins to the mountain in quaint Vermont village is a country house in Montgomery, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free wifi, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,098.

From$300/night

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Pet-friendly vacation rentals in Montgomery, VT

Bring your pet along with stays that welcome four-legged travelers.

Absolute best ski on-off Slopeside location. Summer 2025 Reno just completed.

Condo, Montgomery

Absolute best ski on-off Slopeside location. Summer 2025 Reno just completed. is a condo in Montgomery, with parking. This stay gives travelers a comfortable base for exploring the area,…

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About Absolute best ski on-off Slopeside location. Summer 2025 Reno just completed.

Absolute best ski on-off Slopeside location. Summer 2025 Reno just completed. is a condo in Montgomery, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free wifi, parking, free parking, and fireplace.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,333.

From$190/night

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Ski in Ski out - fantastic location on Raccoon Run

Holiday Home, Montgomery

Ski in Ski out - fantastic location on Raccoon Run is a holiday home in Montgomery, with kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Ski in Ski out - fantastic location on Raccoon Run

Ski in Ski out - fantastic location on Raccoon Run is a holiday home in Montgomery, with kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free wifi, kitchen, with kitchen, and gym.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,655.

From$236/night

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Rustic Vermont Barn Home Near Jay Peak w/Pizza Oven

Holiday Home, Montgomery

Rustic Vermont Barn Home Near Jay Peak w/Pizza Oven is a holiday home in Montgomery, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring…

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About Rustic Vermont Barn Home Near Jay Peak w/Pizza Oven

Rustic Vermont Barn Home Near Jay Peak w/Pizza Oven is a holiday home in Montgomery, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, pet friendly, pets friendly, and kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,505.

From$358/night

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The Retreat - An smazing spa-grade 1BR suite located adjacent to SpaVermont, northern Vermont's most amazing day spa. Only 7 minutes to Jay Peak Resort. With Breakfast Included!

B & B, Montgomery

The Retreat - An smazing spa-grade 1BR suite located adjacent to SpaVermont, northern Vermont's most amazing day spa. Only 7 minutes to Jay Peak Resort. With Breakfast Included! is a b & b…

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About The Retreat - An smazing spa-grade 1BR suite located adjacent to SpaVermont, northern Vermont's most amazing day spa. Only 7 minutes to Jay Peak Resort. With Breakfast Included!

The Retreat - An smazing spa-grade 1BR suite located adjacent to SpaVermont, northern Vermont's most amazing day spa. Only 7 minutes to Jay Peak Resort. With Breakfast Included! is a b & b in Montgomery, with parking, room for a group, and a quieter setting. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: hot tub, free wifi, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,438.

From$348/night

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Vacation rentals with a kitchen in Montgomery, VT

Compare stays with kitchen access for longer trips and easier meals.

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

Condo, Montgomery

Ski in/Ski out 2 Bedroom Directly on Grammy Jay Run is a condo in Montgomery, with kitchen access and room for a group. This stay gives travelers a comfortable base for exploring the area,…

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

Ski in/Ski out 2 Bedroom Directly on Grammy Jay Run is a condo in Montgomery, with kitchen access and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, hot tub, free wifi, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,446.

From$207/night

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Jay Peak 3 miles - ski home via Big Jay!

Holiday Home, Montgomery

Jay Peak 3 miles - ski home via Big Jay! is a holiday home in Montgomery, with kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings,…

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About Jay Peak 3 miles - ski home via Big Jay!

Jay Peak 3 miles - ski home via Big Jay! is a holiday home in Montgomery, with kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, kitchen, with kitchen, fireplace, and washer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,560.

From$223/night

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Jay Peak 3mi - ski home via Big Jay!

Apartment, Montgomery

Jay Peak 3mi - ski home via Big Jay! is a apartment in Montgomery, with kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and…

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About Jay Peak 3mi - ski home via Big Jay!

Jay Peak 3mi - ski home via Big Jay! is a apartment in Montgomery, with kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, kitchen, with kitchen, fireplace, and washer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,579.

From$226/night

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Beautiful Jay Peak ski-in/ski-out condo w/HOT TUB!

Condo, Montgomery

Beautiful Jay Peak ski-in/ski-out condo w/HOT TUB! is a condo in Montgomery, with kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About Beautiful Jay Peak ski-in/ski-out condo w/HOT TUB!

Beautiful Jay Peak ski-in/ski-out condo w/HOT TUB! is a condo in Montgomery, with kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, hot tub, free wifi, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,649.

From$236/night

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Family-friendly vacation rentals in Montgomery, VT

Plan a trip with stays that give families more room to spread out.

Whimsy Cottage - Perfect ski cottage & discounted lift tickets

Cottage, Montgomery

Whimsy Cottage - Perfect ski cottage & discounted lift tickets is a cottage in Montgomery, with kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Whimsy Cottage - Perfect ski cottage & discounted lift tickets

Whimsy Cottage - Perfect ski cottage & discounted lift tickets is a cottage in Montgomery, with kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free wifi, kitchen, with kitchen, kids friendly, and kids friendly videos or books.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,387.

From$198/night

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Ski, Golf, Bike, Hiking, snowmobiles and more

Cottage, Montgomery

Ski, Golf, Bike, Hiking, snowmobiles and more is a cottage in Montgomery, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and…

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About Ski, Golf, Bike, Hiking, snowmobiles and more

Ski, Golf, Bike, Hiking, snowmobiles and more is a cottage in Montgomery, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, parking, free parking, fireplace, and washer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,461.

From$209/night

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Jay Peak 3 Bedroom Trailside Condo directly on the mountain. Walk to water park

Holiday Home, Montgomery

Jay Peak 3 Bedroom Trailside Condo directly on the mountain. Walk to water park is a holiday home in Montgomery, with kitchen access and room for a group. This stay gives travelers a…

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About Jay Peak 3 Bedroom Trailside Condo directly on the mountain. Walk to water park

Jay Peak 3 Bedroom Trailside Condo directly on the mountain. Walk to water park is a holiday home in Montgomery, with kitchen access and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free wifi, kitchen, with kitchen, kids friendly, and kids friendly videos or books.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,868.

From$267/night

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Great Family Getaway! Ski-In Ski-Out Luxury Condo at Jay Peak Resort.

Condo, Montgomery

Great Family Getaway! Ski-In Ski-Out Luxury Condo at Jay Peak Resort. is a condo in Montgomery, with kitchen access and room for a group. This stay gives travelers a comfortable base for…

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About Great Family Getaway! Ski-In Ski-Out Luxury Condo at Jay Peak Resort.

Great Family Getaway! Ski-In Ski-Out Luxury Condo at Jay Peak Resort. is a condo in Montgomery, with kitchen access and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, kitchen, with kitchen, and gym.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,876.

From$268/night

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