Vacation rentals in Chester, VT

30 available vacation rental offers

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Best vacation rentals and Airbnb offers in Chester, VT

Peaceful Brookside Getaway ~10 Mi to Okemo Slopes! - Chester, VT
10 ★ 2 reviews

Peaceful Brookside Getaway ~10 Mi to Okemo Slopes!

Cottage, Chester

Peaceful Brookside Getaway ~10 Mi to Okemo Slopes! is a cottage in Chester, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Peaceful Brookside Getaway ~10 Mi to Okemo Slopes!

Peaceful Brookside Getaway ~10 Mi to Okemo Slopes! is a cottage in Chester, 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, Sep 26 - Sat, Oct 3 · 7 nights · total from $1,650.

From$190/night
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Cozy Ski-in/ski-out Condo on Magic Mountain - Chester, VT
10 ★ 2 reviews

Cozy Ski-in/ski-out Condo on Magic Mountain

Apartment, Chester

Cozy Ski-in/ski-out Condo on Magic Mountain is a apartment in Chester, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About Cozy Ski-in/ski-out Condo on Magic Mountain

Cozy Ski-in/ski-out Condo on Magic Mountain is a apartment in Chester, 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, free wifi, kitchen, with kitchen, and parking.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $2,371.

From$273/night
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Lovely Ludlow Farmhouse ~ 1 Mi to Town & Slopes! - Chester, VT
10 ★ 1 reviews

Lovely Ludlow Farmhouse ~ 1 Mi to Town & Slopes!

Cottage, Chester

Lovely Ludlow Farmhouse ~ 1 Mi to Town & Slopes! is a cottage in Chester, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Lovely Ludlow Farmhouse ~ 1 Mi to Town & Slopes!

Lovely Ludlow Farmhouse ~ 1 Mi to Town & Slopes! is a cottage in Chester, 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, Sep 26 - Sat, Oct 3 · 7 nights · total from $2,670.

From$303/night
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Hike, Ski & Unwind: Cabin w/ Deck in Chester! - Chester, VT
4 ★ 1 reviews

Hike, Ski & Unwind: Cabin w/ Deck in Chester!

Cottage, Chester

Hike, Ski & Unwind: Cabin w/ Deck in Chester! is a cottage in Chester, with outdoor space and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Hike, Ski & Unwind: Cabin w/ Deck in Chester!

Hike, Ski & Unwind: Cabin w/ Deck in Chester! is a cottage in Chester, with outdoor 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, hot tub, free wifi, kitchen, and with kitchen.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $1,766.

From$193/night
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Family-friendly vacation rentals in Chester, VT

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

8 Mi to Okemo Mountain Resort: Mtn-view Retreat! - Chester, VT
10 ★ 1 reviews

8 Mi to Okemo Mountain Resort: Mtn-view Retreat!

Cottage, Chester

8 Mi to Okemo Mountain Resort: Mtn-view Retreat! is a cottage in Chester, with pet-friendly space, kitchen access, and a quieter setting. This stay gives travelers a comfortable base for…

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About 8 Mi to Okemo Mountain Resort: Mtn-view Retreat!

8 Mi to Okemo Mountain Resort: Mtn-view Retreat! is a cottage in Chester, with pet-friendly space, 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, pet friendly, pets friendly, and kitchen.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $7,751.

From$946/night
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Peaceful All-season Getaway for Families in Ludlow - Chester, VT

Peaceful All-season Getaway for Families in Ludlow

Cottage, Chester

Peaceful All-season Getaway for Families in Ludlow is a cottage in Chester, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Peaceful All-season Getaway for Families in Ludlow

Peaceful All-season Getaway for Families in Ludlow is a cottage in Chester, 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, free wifi, kitchen, with kitchen, and parking.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $2,020.

From$228/night
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Londonderry Retreat ~ 3 Mi to Lowell Lake! - Chester, VT

Londonderry Retreat ~ 3 Mi to Lowell Lake!

Cottage, Chester

Londonderry Retreat ~ 3 Mi to Lowell Lake! is a cottage in Chester, with pet-friendly space, kitchen access, and a quieter setting. This stay gives travelers a comfortable base for…

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About Londonderry Retreat ~ 3 Mi to Lowell Lake!

Londonderry Retreat ~ 3 Mi to Lowell Lake! is a cottage in Chester, with pet-friendly space, 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, pet friendly, pets friendly, and kitchen.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $2,908.

From$334/night
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Renovated Farmhouse < 1 Mile to Okemo Mountain! - Chester, VT

Renovated Farmhouse < 1 Mile to Okemo Mountain!

Cottage, Chester

Renovated Farmhouse < 1 Mile to Okemo Mountain! is a cottage in Chester, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Renovated Farmhouse < 1 Mile to Okemo Mountain!

Renovated Farmhouse < 1 Mile to Okemo Mountain! is a cottage in Chester, 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, free wifi, kitchen, with kitchen, and parking.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $3,624.

From$426/night
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Pet-friendly vacation rentals in Chester, VT

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

Ludlow Townhome: 3 Mi to Okemo Mountain! - Chester, VT

Ludlow Townhome: 3 Mi to Okemo Mountain!

Apartment, Chester

Ludlow Townhome: 3 Mi to Okemo Mountain! is a apartment in Chester, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Ludlow Townhome: 3 Mi to Okemo Mountain!

Ludlow Townhome: 3 Mi to Okemo Mountain! is a apartment in Chester, 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, Sep 26 - Sat, Oct 3 · 7 nights · total from $2,237.

From$267/night
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Londonderry Retreat ~ 3 Mi to Lowell Lake! - Chester, VT

Londonderry Retreat ~ 3 Mi to Lowell Lake!

Holiday Home, Chester

Londonderry Retreat ~ 3 Mi to Lowell Lake! is a holiday home in Chester, with pet-friendly space and a quieter setting. This stay gives travelers a comfortable base for exploring the area,…

Read more

About Londonderry Retreat ~ 3 Mi to Lowell Lake!

Londonderry Retreat ~ 3 Mi to Lowell Lake! is a holiday home in Chester, with pet-friendly space 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, hot tub, free wifi, pet friendly, and pets friendly.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $2,880.

From$295/night
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Spacious Mountain Retreat - Chester, VT

Spacious Mountain Retreat

Holiday Home, Chester

Spacious Mountain Retreat is a holiday home in Chester, with pet-friendly space and a quieter setting. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About Spacious Mountain Retreat

Spacious Mountain Retreat is a holiday home in Chester, with pet-friendly space 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, pet friendly, and pets friendly.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $3,928.

From$408/night
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All-Season Ludlow Apartment: 3 Mi to Okemo Resort! - Chester, VT

All-Season Ludlow Apartment: 3 Mi to Okemo Resort!

Apartment, Chester

All-Season Ludlow Apartment: 3 Mi to Okemo Resort! is a apartment in Chester, with pet-friendly space and parking. This stay gives travelers a comfortable base for exploring the area,…

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About All-Season Ludlow Apartment: 3 Mi to Okemo Resort!

All-Season Ludlow Apartment: 3 Mi to Okemo Resort! is a apartment in Chester, with pet-friendly space and 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, free wifi, pet friendly, pets friendly, and parking.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $3,839.

From$412/night
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Vacation rentals with parking in Chester, VT

Find vacation rentals that make arriving by car easier.

Ludlow Hideout - Chester, VT

Ludlow Hideout

Holiday Home, Chester

Ludlow Hideout is a holiday home in Chester, 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 Ludlow Hideout

Ludlow Hideout is a holiday home in Chester, 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, Sep 26 - Sat, Oct 3 · 7 nights · total from $2,439.

From$241/night
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Renovated Farmhouse < 1 Mile to Okemo Mountain! - Chester, VT

Renovated Farmhouse < 1 Mile to Okemo Mountain!

Holiday Home, Chester

Renovated Farmhouse < 1 Mile to Okemo Mountain! is a holiday home in Chester, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings,…

Read more

About Renovated Farmhouse < 1 Mile to Okemo Mountain!

Renovated Farmhouse < 1 Mile to Okemo Mountain! is a holiday home in Chester, 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, free wifi, parking, paid parking, and heating.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $3,616.

From$383/night
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Cozy Ski-In/Ski-Out Condo on Magic Mountain - Chester, VT

Cozy Ski-In/Ski-Out Condo on Magic Mountain

Holiday Home, Chester

Cozy Ski-In/Ski-Out Condo on Magic Mountain is a holiday home in Chester, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and…

Read more

About Cozy Ski-In/Ski-Out Condo on Magic Mountain

Cozy Ski-In/Ski-Out Condo on Magic Mountain is a holiday home in Chester, 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, free wifi, gym, parking, and paid parking.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $2,347.

From$236/night
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Vibrant Views - Chester, VT

Vibrant Views

Holiday Home, Chester

Vibrant Views is a holiday home in Chester, 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 Vibrant Views

Vibrant Views is a holiday home in Chester, 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, ac, and air conditioning.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $2,722.

From$286/night
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Vacation rentals with a kitchen in Chester, VT

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

All-season Ludlow Apartment: 3 Mi to Okemo Resort! - Chester, VT

All-season Ludlow Apartment: 3 Mi to Okemo Resort!

Apartment, Chester

All-season Ludlow Apartment: 3 Mi to Okemo Resort! is a apartment in Chester, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the…

Read more

About All-season Ludlow Apartment: 3 Mi to Okemo Resort!

All-season Ludlow Apartment: 3 Mi to Okemo Resort! is a apartment in Chester, 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, Sep 26 - Sat, Oct 3 · 7 nights · total from $3,846.

From$456/night
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Spacious Ludlow Hideaway < 1 Mi to Okemo Mountain! - Chester, VT

Spacious Ludlow Hideaway < 1 Mi to Okemo Mountain!

Cottage, Chester

Spacious Ludlow Hideaway < 1 Mi to Okemo Mountain! is a cottage in Chester, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

Read more

About Spacious Ludlow Hideaway < 1 Mi to Okemo Mountain!

Spacious Ludlow Hideaway < 1 Mi to Okemo Mountain! is a cottage in Chester, 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, Sep 26 - Sat, Oct 3 · 7 nights · total from $7,177.

From$884/night
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Luxe Mountain Home w/ Chefs Kitchen & Okemo Views - Chester, VT

Luxe Mountain Home w/ Chefs Kitchen & Okemo Views

Cottage, Chester

Luxe Mountain Home w/ Chefs Kitchen & Okemo Views is a cottage in Chester, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Luxe Mountain Home w/ Chefs Kitchen & Okemo Views

Luxe Mountain Home w/ Chefs Kitchen & Okemo Views is a cottage in Chester, 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, free wifi, kitchen, with kitchen, and parking.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $11,219.

From$1,374/night
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Other places to stay in Chester, VT

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