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Petersburg Holiday Rentals

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50 rentals in Petersburg.
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Tutti Farm - 6 Bed 3 Bath 1847 Farmhouse Upstate NY, holiday rental in Petersburg

Tutti Farm - 6 Bed 3 Bath 1847 Farmhouse Upstate NY

6 bedrooms
3 bathrooms
Sleeps 12
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The Lodge at Fox Hollow, holiday rental in Petersburg

The Lodge at Fox Hollow

2 bedrooms
3 bathrooms
Sleeps 7
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Romantic Bennington Vermont Cottage, holiday rental in Petersburg

Romantic Bennington Vermont Cottage

1 bedroom
1 bathroom
Sleeps 4
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Huge Luxe Williamstown Updated Victorian,  All Ensuite Baths, Walk to Spring St!, holiday rental in Petersburg

Huge Luxe Williamstown Updated Victorian, All Ensuite Baths, Walk to Spring St!

5 bedrooms
6 bathrooms
Sleeps 15
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Charming Downtown Williamstown Cottage - 5 Min Walk to Campus, holiday rental in Petersburg

Charming Downtown Williamstown Cottage - 5 Min Walk to Campus

3 bedrooms
2 bathrooms
Sleeps 7
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New Rates! BEAUTIFUL Ski-In/Ski-Out - Jiminy Peak Mountain Resort - Berkshires, holiday rental in Petersburg

New Rates! BEAUTIFUL Ski-In/Ski-Out - Jiminy Peak Mountain Resort - Berkshires

2 bedrooms
2 bathrooms
Sleeps 6
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Victorian Home in Bennington, Vermont, holiday rental in Petersburg

Victorian Home in Bennington, Vermont

3 bedrooms
3 bathrooms
Sleeps 7
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Perfect for a peaceful get away in clean fresh Vermont air!, holiday rental in Petersburg

Perfect for a peaceful get away in clean fresh Vermont air!

3 bedrooms
5 bathrooms
Sleeps 6
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Cozy renovated cabin in Williamstown, steps from hiking trails, holiday rental in Petersburg

Cozy renovated cabin in Williamstown, steps from hiking trails

2 bedrooms
2 bathrooms
Sleeps 5
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19th c. Renovated Barn in the Berkshires, holiday rental in Petersburg

19th c. Renovated Barn in the Berkshires

3 bedrooms
2 bathrooms
Sleeps 10
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A roomy remodeled retreat close to MassMoCA, holiday rental in Petersburg

A roomy remodeled retreat close to MassMoCA

4 bedrooms
2 bathrooms
Sleeps 8
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Attn MA residents - Private Ski in/Ski out 4 BR Home on Jiminy Peak, holiday rental in Petersburg

Attn MA residents - Private Ski in/Ski out 4 BR Home on Jiminy Peak

4 bedrooms
3 bathrooms
Sleeps 12
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Home in the Berkshires, holiday rental in Petersburg

Home in the Berkshires

4 bedrooms
3 bathrooms
Sleeps 8
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Vermont Hillside Retreat, holiday rental in Petersburg

Vermont Hillside Retreat

4 bedrooms
2 bathrooms
Sleeps 12
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Berkshire Gorge House, 15 minutes to Williamstown, 15 minutes to Jiminy Peak., holiday rental in Petersburg

Berkshire Gorge House, 15 minutes to Williamstown, 15 minutes to Jiminy Peak.

5 bedrooms
3 bathrooms
Sleeps 6
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Bennington Guest Farmhouse, holiday rental in Petersburg

Bennington Guest Farmhouse

5 bedrooms
2 bathrooms
Sleeps 9
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1920's Bennington Vermont Guest Barn, holiday rental in Petersburg

1920's Bennington Vermont Guest Barn

3 bedrooms
1 bathroom
Sleeps 7
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6BR Berkshire Bliss - 38 Acres of nature - minutes from Jiminy Peak Ski Resort, holiday rental in Petersburg

6BR Berkshire Bliss - 38 Acres of nature - minutes from Jiminy Peak Ski Resort

6 bedrooms
5 bathrooms
Sleeps 14
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Country Cottage Charm, Close To Albany And Ski Areas Of New England, holiday rental in Petersburg

Country Cottage Charm, Close To Albany And Ski Areas Of New England

2 bedrooms
1 bathroom
Sleeps 4
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Cozy and quaint country cottage, walk to downtown Williamstown, holiday rental in Petersburg

Cozy and quaint country cottage, walk to downtown Williamstown

2 bedrooms
1 bathroom
Sleeps 4
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Beautifully decorated with holiday lights and tree, holiday rental in Petersburg

Beautifully decorated with holiday lights and tree

5 bedrooms
2 bathrooms
Sleeps 10
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Historic c.1880 Victorian MA/VT border near Williams College MassMoCA Freshgrass, holiday rental in Petersburg

Historic c.1880 Victorian MA/VT border near Williams College MassMoCA Freshgrass

5 bedrooms
2 bathrooms
Sleeps 12
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The Gathering at High Mowing Williamstown, holiday rental in Petersburg

The Gathering at High Mowing Williamstown

4 bedrooms
3 bathrooms
Sleeps 7
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Newly renovated, spacious and sunlight filled condo with mountain views, holiday rental in Petersburg

Newly renovated, spacious and sunlight filled condo with mountain views

2 bedrooms
2 bathrooms
Sleeps 6
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6BR Berkshire Bliss - 38 private acres - close to skiing and town, holiday rental in Petersburg

6BR Berkshire Bliss - 38 private acres - close to skiing and town

6 bedrooms
5 bathrooms
Sleeps 15
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Mounatin Getaway in the Heart of the Berkshires!, holiday rental in Petersburg

Mounatin Getaway in the Heart of the Berkshires!

1 bedroom
1 bathroom
Sleeps 4
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Berkshires Living!! Beautiful Location, Breathtaking Sunset, Fully Renovated Hom, holiday rental in Petersburg

Berkshires Living!! Beautiful Location, Breathtaking Sunset, Fully Renovated Hom

3 bedrooms
2 bathrooms
Sleeps 10
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Cozy 1 Bedroom farm stay cottage, holiday rental in Petersburg

Cozy 1 Bedroom farm stay cottage

1 bedroom
1 bathroom
Sleeps 4
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Whitman Woods - A Berkshire Vacation, holiday rental in Petersburg

Whitman Woods - A Berkshire Vacation

4 bedrooms
2 bathrooms
Sleeps 8
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Golden Triangle in the Berkshires, holiday rental in Petersburg

Golden Triangle in the Berkshires

2 bedrooms
2 bathrooms
Sleeps 4
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Bentley/Wyndham Hancock Mass at Jiminy Peak, holiday rental in Petersburg

Bentley/Wyndham Hancock Mass at Jiminy Peak

2 bedrooms
2 bathrooms
Sleeps 6
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The Meadow House 4 bdrm 4 bath house, holiday rental in Petersburg

The Meadow House 4 bdrm 4 bath house

4 bedrooms
4 bathrooms
Sleeps 12
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Christmas in The Berkshires, holiday rental in Petersburg

Christmas in The Berkshires

1 bedroom
2 bathrooms
Sleeps 4
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Karin's Place, holiday rental in Petersburg

Karin's Place

7 bedrooms
6 bathrooms
Sleeps 20
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Thanksgiving week lux condo/4 Berkshires, holiday rental in Petersburg

Thanksgiving week lux condo/4 Berkshires

2 bedrooms
1 bathroom
Sleeps 4
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Country Farmhouse with Views, holiday rental in Petersburg

Country Farmhouse with Views

4 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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Hancock, MA: Studio w/Valley Views at All-Seasons Resort: Skiing, Hiking & More!, holiday rental in Petersburg

Hancock, MA: Studio w/Valley Views at All-Seasons Resort: Skiing, Hiking & More!

0 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Beautiful Jiminy Peak Mountainside Condo Near Lifts - Just Remodeled, holiday rental in Petersburg

Beautiful Jiminy Peak Mountainside Condo Near Lifts - Just Remodeled

2 bedrooms
2 bathrooms
Sleeps 6
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The Bear Den, holiday rental in Petersburg

The Bear Den

1 bedroom
1 bathroom
Sleeps 2
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Tentrr Signature Site - Center Berlin Campsite, holiday rental in Petersburg

Tentrr Signature Site - Center Berlin Campsite

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Tentrr Signature Site - Hidden Hoosic   Riverside Camp, holiday rental in Petersburg

Tentrr Signature Site - Hidden Hoosic Riverside Camp

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Tentrr Signature Site - Round Mountain Camp, holiday rental in Petersburg

Tentrr Signature Site - Round Mountain Camp

1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
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1 Bed, 1st floor, furnished, includes utilities, TV+internet, holiday rental in Petersburg

1 Bed, 1st floor, furnished, includes utilities, TV+internet

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Hancock Log Cabin Retreat: 2 Miles to Jiminy Peak!, holiday rental in Petersburg

Hancock Log Cabin Retreat: 2 Miles to Jiminy Peak!

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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A MAGIC SPOT: Booking Fall and the Ski Season now!, holiday rental in Petersburg

A MAGIC SPOT: Booking Fall and the Ski Season now!

4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Two Brooks Lodge, holiday rental in Petersburg

Two Brooks Lodge

3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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NEW! Peaceful Family Home w/ Fire Pit & Large Yard, holiday rental in Petersburg

NEW! Peaceful Family Home w/ Fire Pit & Large Yard

4 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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The Brookman - Newly Renovated 6,000 SF Estate on 40 Acres, holiday rental in Petersburg

The Brookman - Newly Renovated 6,000 SF Estate on 40 Acres

8 bedrooms
6 bathrooms
Sleeps 25
Match: Sleeps
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Tentrr Signature Site - Hancock Haven, holiday rental in Petersburg

Tentrr Signature Site - Hancock Haven

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Gorgeous Newly Renovated Victorian with an Amazing treehouse and playground, holiday rental in Petersburg

Gorgeous Newly Renovated Victorian with an Amazing treehouse and playground

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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