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Holiday Homes in Petersburg

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49 rentals in Petersburg.
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COZY, WOODED RETREAT In The Taconic Hills 2+ BR 2.5 BA, large, open LR ., holiday rental in Petersburg
COZY, WOODED RETREAT In The Taconic Hills 2+ BR 2.5 BA, large, open LR ., holiday rental in Petersburg
COZY, WOODED RETREAT In The Taconic Hills 2+ BR 2.5 BA, large, open LR ., holiday rental in Petersburg

COZY, WOODED RETREAT In The Taconic Hills 2+ BR 2.5 BA, large, open LR .

Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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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, holiday rental in Petersburg
Tutti Farm - 6 Bed 3 Bath 1847 Farmhouse Upstate NY, holiday rental in Petersburg

Tutti Farm - 6 Bed 3 Bath 1847 Farmhouse Upstate NY

Holiday Rental House
6 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
More info
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The Lodge at Fox Hollow, holiday rental in Petersburg
The Lodge at Fox Hollow, holiday rental in Petersburg
The Lodge at Fox Hollow, holiday rental in Petersburg

The Lodge at Fox Hollow

Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
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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!, holiday rental in Petersburg
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!

Holiday Rental House
5 bedrooms
6 bathrooms
Sleeps 10
Match: Sleeps
More info
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Romantic Bennington Vermont Cottage, holiday rental in Petersburg
Romantic Bennington Vermont Cottage, holiday rental in Petersburg
Romantic Bennington Vermont Cottage, holiday rental in Petersburg

Romantic Bennington Vermont Cottage

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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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, holiday rental in Petersburg
Charming Downtown Williamstown Cottage - 5 Min Walk to Campus, holiday rental in Petersburg

Charming Downtown Williamstown Cottage - 5 Min Walk to Campus

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Victorian Home in Bennington, Vermont, holiday rental in Petersburg
Victorian Home in Bennington, Vermont, holiday rental in Petersburg
Victorian Home in Bennington, Vermont, holiday rental in Petersburg

Victorian Home in Bennington, Vermont

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
More info
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Secluded Luxury In The Country, Close To Culture, holiday rental in Petersburg
Secluded Luxury In The Country, Close To Culture, holiday rental in Petersburg
Secluded Luxury In The Country, Close To Culture, holiday rental in Petersburg

Secluded Luxury In The Country, Close To Culture

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 24
Match: Sleeps
More info
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Book your Summer Getaway Today!, holiday rental in Petersburg
Book your Summer Getaway Today!, holiday rental in Petersburg
Book your Summer Getaway Today!, holiday rental in Petersburg

Book your Summer Getaway Today!

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
More info
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Quarry Hill Farm - stunning views - cozy yet expansive, holiday rental in Petersburg
Quarry Hill Farm - stunning views - cozy yet expansive, holiday rental in Petersburg
Quarry Hill Farm - stunning views - cozy yet expansive, holiday rental in Petersburg

Quarry Hill Farm - stunning views - cozy yet expansive

Holiday Rental House
8 bedrooms
5 bathrooms
Sleeps 15
Match: Sleeps
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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, holiday rental in Petersburg
Cozy renovated cabin in Williamstown, steps from hiking trails, holiday rental in Petersburg

Cozy renovated cabin in Williamstown, steps from hiking trails

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Quiet, private setting with panoramic mountain views on our small horse farm., holiday rental in Petersburg
Quiet, private setting with panoramic mountain views on our small horse farm., holiday rental in Petersburg
Quiet, private setting with panoramic mountain views on our small horse farm., holiday rental in Petersburg

Quiet, private setting with panoramic mountain views on our small horse farm.

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Historic Home in Old Bennington, Vermont, holiday rental in Petersburg
Historic Home in Old Bennington, Vermont, holiday rental in Petersburg
Historic Home in Old Bennington, Vermont, holiday rental in Petersburg

Historic Home in Old Bennington, Vermont

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
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A roomy remodeled retreat close to MassMoCA, holiday rental in Petersburg
A roomy remodeled retreat close to MassMoCA, holiday rental in Petersburg
A roomy remodeled retreat close to MassMoCA, holiday rental in Petersburg

A roomy remodeled retreat close to MassMoCA

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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Beautiful Southern Vermont Farmhouse on 100 Acres, Spectacular Views, Swim Pond, holiday rental in Petersburg
Beautiful Southern Vermont Farmhouse on 100 Acres, Spectacular Views, Swim Pond, holiday rental in Petersburg
Beautiful Southern Vermont Farmhouse on 100 Acres, Spectacular Views, Swim Pond, holiday rental in Petersburg

Beautiful Southern Vermont Farmhouse on 100 Acres, Spectacular Views, Swim Pond

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
More info
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In town 2 bedroom, one bath carriage barn. Sleeps 5., holiday rental in Petersburg
In town 2 bedroom, one bath carriage barn. Sleeps 5., holiday rental in Petersburg
In town 2 bedroom, one bath carriage barn. Sleeps 5., holiday rental in Petersburg

In town 2 bedroom, one bath carriage barn. Sleeps 5.

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
More info
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Home in the Berkshires

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
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1K sf APT, Harvest to Holiday to Farm Activities, holiday rental in Petersburg
1K sf APT, Harvest to Holiday to Farm Activities, holiday rental in Petersburg
1K sf APT, Harvest to Holiday to Farm Activities, holiday rental in Petersburg

1K sf APT, Harvest to Holiday to Farm Activities

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
More info
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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., holiday rental in Petersburg
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.

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
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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, holiday rental in Petersburg
Cozy and quaint country cottage, walk to downtown Williamstown, holiday rental in Petersburg

Cozy and quaint country cottage, walk to downtown Williamstown

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Gracious Home with Pool: Private and Spacious,  Close to Town, holiday rental in Petersburg
Gracious Home with Pool: Private and Spacious,  Close to Town, holiday rental in Petersburg
Gracious Home with Pool: Private and Spacious,  Close to Town, holiday rental in Petersburg

Gracious Home with Pool: Private and Spacious, Close to Town

Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
More info
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Beautifully decorated with holiday lights and tree, holiday rental in Petersburg
Beautifully decorated with holiday lights and tree, holiday rental in Petersburg
Beautifully decorated with holiday lights and tree, holiday rental in Petersburg

Beautifully decorated with holiday lights and tree

Holiday Rental House
5 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
More info
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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!, holiday rental in Petersburg
A MAGIC SPOT: Booking Fall and the Ski Season now!, holiday rental in Petersburg

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

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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Tranquil Farmhouse away from the Crowds, holiday rental in Petersburg
Tranquil Farmhouse away from the Crowds, holiday rental in Petersburg
Tranquil Farmhouse away from the Crowds, holiday rental in Petersburg

Tranquil Farmhouse away from the Crowds

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
More info
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Large, family-friendly farmhouse located in the beautiful Berkshires, holiday rental in Petersburg
Large, family-friendly farmhouse located in the beautiful Berkshires, holiday rental in Petersburg
Large, family-friendly farmhouse located in the beautiful Berkshires, holiday rental in Petersburg

Large, family-friendly farmhouse located in the beautiful Berkshires

Holiday Rental House
7 bedrooms
3 bathrooms
Sleeps 14
Match: Sleeps
More info
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The Henry House & Authentic Red Covered Bridge!, holiday rental in Petersburg
The Henry House & Authentic Red Covered Bridge!, holiday rental in Petersburg
The Henry House & Authentic Red Covered Bridge!, holiday rental in Petersburg

The Henry House & Authentic Red Covered Bridge!

Holiday Rental House
6 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
More info
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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!, holiday rental in Petersburg
Hancock Log Cabin Retreat: 2 Miles to Jiminy Peak!, holiday rental in Petersburg

Hancock Log Cabin Retreat: 2 Miles to Jiminy Peak!

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Two Brooks Lodge - Beautiful Waterfront Vermont Retreat, holiday rental in Petersburg
Two Brooks Lodge - Beautiful Waterfront Vermont Retreat, holiday rental in Petersburg
Two Brooks Lodge - Beautiful Waterfront Vermont Retreat, holiday rental in Petersburg

Two Brooks Lodge - Beautiful Waterfront Vermont Retreat

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
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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, holiday rental in Petersburg
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

Holiday Rental House
5 bedrooms
2 bathrooms
Sleeps 12
Match: Sleeps
More info
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Chic Berkshire Dollhouse!, holiday rental in Petersburg
Chic Berkshire Dollhouse!, holiday rental in Petersburg
Chic Berkshire Dollhouse!, holiday rental in Petersburg

Chic Berkshire Dollhouse!

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Private Estate, 5 Bedrooms, Hot Tub, Tranquil Setting!, holiday rental in Petersburg
Private Estate, 5 Bedrooms, Hot Tub, Tranquil Setting!, holiday rental in Petersburg
Private Estate, 5 Bedrooms, Hot Tub, Tranquil Setting!, holiday rental in Petersburg

Private Estate, 5 Bedrooms, Hot Tub, Tranquil Setting!

Holiday Rental House
5 bedrooms
5 bathrooms
Sleeps 16
Match: Sleeps
More info
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family-friendly, private cottage in the beautiful Berkshires, holiday rental in Petersburg
family-friendly, private cottage in the beautiful Berkshires, holiday rental in Petersburg
family-friendly, private cottage in the beautiful Berkshires, holiday rental in Petersburg

family-friendly, private cottage in the beautiful Berkshires

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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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, holiday rental in Petersburg
Berkshires Living!! Beautiful Location, Breathtaking Sunset, Fully Renovated Hom, holiday rental in Petersburg

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

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
More info
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Whitman Woods - A Berkshire Vacation, holiday rental in Petersburg
Whitman Woods - A Berkshire Vacation, holiday rental in Petersburg
Whitman Woods - A Berkshire Vacation, holiday rental in Petersburg

Whitman Woods - A Berkshire Vacation

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Golden Triangle in the Berkshires, holiday rental in Petersburg
Golden Triangle in the Berkshires, holiday rental in Petersburg
Golden Triangle in the Berkshires, holiday rental in Petersburg

Golden Triangle in the Berkshires

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
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Furnished Remote Work Dream near Albany, holiday rental in Petersburg
Furnished Remote Work Dream near Albany, holiday rental in Petersburg
Furnished Remote Work Dream near Albany, holiday rental in Petersburg

Furnished Remote Work Dream near Albany

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
More info
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Karin's Place, holiday rental in Petersburg
Karin's Place, holiday rental in Petersburg
Karin's Place, holiday rental in Petersburg

Karin's Place

Holiday Rental House
7 bedrooms
6 bathrooms
Sleeps 20
Match: Sleeps
More info
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11 acre mid-century estate, newly renovated, holiday rental in Petersburg
11 acre mid-century estate, newly renovated, holiday rental in Petersburg
11 acre mid-century estate, newly renovated, holiday rental in Petersburg

11 acre mid-century estate, newly renovated

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
More info
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Studio Sleeps 2 In Country Setting, holiday rental in Petersburg
Studio Sleeps 2 In Country Setting, holiday rental in Petersburg
Studio Sleeps 2 In Country Setting, holiday rental in Petersburg

Studio Sleeps 2 In Country Setting

Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
More info
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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, holiday rental in Petersburg
1 Bed, 1st floor, furnished, includes utilities, TV+internet, holiday rental in Petersburg

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

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Charming, Fully Restored, Greek Revival House, Farmland Setting, holiday rental in Petersburg
Charming, Fully Restored, Greek Revival House, Farmland Setting, holiday rental in Petersburg
Charming, Fully Restored, Greek Revival House, Farmland Setting, holiday rental in Petersburg

Charming, Fully Restored, Greek Revival House, Farmland Setting

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
More info
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Ultra Luxury new home in Williamstown  (3 miles from Williams College, 10 miles, holiday rental in Petersburg
Ultra Luxury new home in Williamstown  (3 miles from Williams College, 10 miles, holiday rental in Petersburg
Ultra Luxury new home in Williamstown  (3 miles from Williams College, 10 miles, holiday rental in Petersburg

Ultra Luxury new home in Williamstown (3 miles from Williams College, 10 miles

Holiday Rental House
7 bedrooms
8 bathrooms
Sleeps 17
Match: Sleeps
More info
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Luxury Living High Above the Center of Town., holiday rental in Petersburg
Luxury Living High Above the Center of Town., holiday rental in Petersburg
Luxury Living High Above the Center of Town., holiday rental in Petersburg

Luxury Living High Above the Center of Town.

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Two Brooks Lodge, holiday rental in Petersburg
Two Brooks Lodge, holiday rental in Petersburg
Two Brooks Lodge, holiday rental in Petersburg

Two Brooks Lodge

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
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Best Western Bennington - Deluxe King Bed #5, holiday rental in Petersburg
Best Western Bennington - Deluxe King Bed #5, holiday rental in Petersburg
Best Western Bennington - Deluxe King Bed #5, holiday rental in Petersburg

Best Western Bennington - Deluxe King Bed #5

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Art House! Spacious Getaway By Mass Moca, holiday rental in Petersburg
Art House! Spacious Getaway By Mass Moca, holiday rental in Petersburg
Art House! Spacious Getaway By Mass Moca, holiday rental in Petersburg

Art House! Spacious Getaway By Mass Moca

Holiday Rental House
6 bedrooms
2 bathrooms
Sleeps 12
Match: Sleeps
More info
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Best Western Bennington - Deluxe King Bed #4, holiday rental in Petersburg
Best Western Bennington - Deluxe King Bed #4, holiday rental in Petersburg
Best Western Bennington - Deluxe King Bed #4, holiday rental in Petersburg

Best Western Bennington - Deluxe King Bed #4

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Enchanting forest hide-away, holiday rental in Petersburg
Enchanting forest hide-away, holiday rental in Petersburg
Enchanting forest hide-away, holiday rental in Petersburg

Enchanting forest hide-away

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
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Private Country home near Berkshires, holiday rental in Petersburg
Private Country home near Berkshires, holiday rental in Petersburg
Private Country home near Berkshires, holiday rental in Petersburg

Private Country home near Berkshires

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
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Pleasant on Pleasant, holiday rental in Petersburg
Pleasant on Pleasant, holiday rental in Petersburg
Pleasant on Pleasant, holiday rental in Petersburg

Pleasant on Pleasant

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 1
More info
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