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Shaftsbury Holiday Rentals

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50 rentals in Shaftsbury.
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200 Yr old Farmhouse on 45 acres, holiday rental in Shaftsbury

200 Yr old Farmhouse on 45 acres

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Escape the Chaos! Private cabin/ 40 Acres, holiday rental in Shaftsbury

Escape the Chaos! Private cabin/ 40 Acres

3 bedrooms
1 bathroom
Sleeps 7
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Vermont Hillside Retreat, holiday rental in Shaftsbury

Vermont Hillside Retreat

4 bedrooms
2 bathrooms
Sleeps 12
Match: Sleeps
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Stunning Post and Beam Art Studio/House, holiday rental in Shaftsbury

Stunning Post and Beam Art Studio/House

3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Country Farmhouse with Views, holiday rental in Shaftsbury

Country Farmhouse with Views

4 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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Renovated 2 Bedroom Cottage With View Of The Roaring Branch From 2nd Floor, holiday rental in Shaftsbury

Renovated 2 Bedroom Cottage With View Of The Roaring Branch From 2nd Floor

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Spacious Three-level Home , Well-Furnished, Fun Playroom, Minutes to Mt. Snow, holiday rental in Shaftsbury

Spacious Three-level Home , Well-Furnished, Fun Playroom, Minutes to Mt. Snow

4 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Romantic Bennington Vermont Cottage, holiday rental in Shaftsbury

Romantic Bennington Vermont Cottage

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Spacious Mountain view home Booking Fall/Winter 2020-21, holiday rental in Shaftsbury

Spacious Mountain view home Booking Fall/Winter 2020-21

5 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Great Place to get away and have clean fresh air surround you!, holiday rental in Shaftsbury

Great Place to get away and have clean fresh air surround you!

1 bedroom
1 bathroom
Sleeps 6
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Victorian Home in Bennington, Vermont, holiday rental in Shaftsbury

Victorian Home in Bennington, Vermont

3 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
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All season lake front getaway!, holiday rental in Shaftsbury

All season lake front getaway!

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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1828 Vermont Cottage Feet From The Famous Battenkill River, holiday rental in Shaftsbury

1828 Vermont Cottage Feet From The Famous Battenkill River

3 bedrooms
2 bathrooms
Sleeps 5
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Perfect for a peaceful get away in clean fresh Vermont air!, holiday rental in Shaftsbury

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

3 bedrooms
5 bathrooms
Sleeps 6
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HUGE Mansion: Privacy. Great for groups, retreats, yoga, DIY weddings. Sleeps 34, holiday rental in Shaftsbury

HUGE Mansion: Privacy. Great for groups, retreats, yoga, DIY weddings. Sleeps 34

15 bedrooms
13 bathrooms
Sleeps 34
Match: Sleeps
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Historic 1913 Railroad Station Full of History, Views and Modern Amentities!, holiday rental in Shaftsbury

Historic 1913 Railroad Station Full of History, Views and Modern Amentities!

3 bedrooms
2 bathrooms
Sleeps 6
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LITTLE BIT OF HEAVEN in Southern VT - Mt Snow, Berkshires, Bennington, Mass Moca, holiday rental in Shaftsbury

LITTLE BIT OF HEAVEN in Southern VT - Mt Snow, Berkshires, Bennington, Mass Moca

3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Stunning Slope-side Ski-on Ski-off 4 bedroom 4.5 bath Townhouse at Trails Edge, holiday rental in Shaftsbury

Stunning Slope-side Ski-on Ski-off 4 bedroom 4.5 bath Townhouse at Trails Edge

4 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
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3 Bedroom Chalet with Hot Tub 10 Mins to Mt Snow with Clubhouse Amenities, holiday rental in Shaftsbury

3 Bedroom Chalet with Hot Tub 10 Mins to Mt Snow with Clubhouse Amenities

3 bedrooms
2 bathrooms
Sleeps 10
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Country Getaway Lodge / Ranch, holiday rental in Shaftsbury

Country Getaway Lodge / Ranch

5 bedrooms
4 bathrooms
Sleeps 14
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Beautiful  Vermont Vacation Home- Mount Snow!!, holiday rental in Shaftsbury

Beautiful Vermont Vacation Home- Mount Snow!!

4 bedrooms
2 bathrooms
Sleeps 14
Match: Sleeps
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4 BR, 2BA: Comfy, Clean & Family Friendly - 15 mins to Mount Snow!, holiday rental in Shaftsbury

4 BR, 2BA: Comfy, Clean & Family Friendly - 15 mins to Mount Snow!

4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Kayaker & Fly-fisher DREAM, private BattenKill waterfront super charming home, holiday rental in Shaftsbury

Kayaker & Fly-fisher DREAM, private BattenKill waterfront super charming home

3 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Walk To Mt. Snow - Newly Updated - Open Concept - Mountain Views, holiday rental in Shaftsbury

Walk To Mt. Snow - Newly Updated - Open Concept - Mountain Views

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Cozy Mountain Escape to Southern Vermont, holiday rental in Shaftsbury

Cozy Mountain Escape to Southern Vermont

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Bennington Guest Farmhouse, holiday rental in Shaftsbury

Bennington Guest Farmhouse

5 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
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New home in the heart of the Green Mountain Forest, holiday rental in Shaftsbury

New home in the heart of the Green Mountain Forest

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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1920's Bennington Vermont Guest Barn, holiday rental in Shaftsbury

1920's Bennington Vermont Guest Barn

3 bedrooms
1 bathroom
Sleeps 7
Match: Sleeps
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Cozy Vermont home for your Summer and Fall getaway, holiday rental in Shaftsbury

Cozy Vermont home for your Summer and Fall getaway

4 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
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Large Family Home Near Bromley, Stratton Mountains, holiday rental in Shaftsbury

Large Family Home Near Bromley, Stratton Mountains

5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Ski Season Special! $29,500 (+ heat & electric) 6 bedroom/6 bath, dogs ok, holiday rental in Shaftsbury

Ski Season Special! $29,500 (+ heat & electric) 6 bedroom/6 bath, dogs ok

6 bedrooms
6 bathrooms
Sleeps 20
Match: Sleeps
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Levity Mountain: Farmhouse, Cottage, and Event Barn, holiday rental in Shaftsbury

Levity Mountain: Farmhouse, Cottage, and Event Barn

8 bedrooms
5 bathrooms
Sleeps 24
Match: Sleeps
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NEW LISTING - Cozy Mountain Retreat on the Roaring Branch - dogs welcome, holiday rental in Shaftsbury

NEW LISTING - Cozy Mountain Retreat on the Roaring Branch - dogs welcome

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Designer Vermont Vacation Retreat, holiday rental in Shaftsbury

Designer Vermont Vacation Retreat

4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Historic c.1880 Victorian MA/VT border near Williams College MassMoCA Freshgrass, holiday rental in Shaftsbury

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

5 bedrooms
2 bathrooms
Sleeps 12
Match: Sleeps
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Cozy 4 season getaway in Vermont near Mt. Snow, holiday rental in Shaftsbury

Cozy 4 season getaway in Vermont near Mt. Snow

3 bedrooms
2 bathrooms
Sleeps 13
Match: Sleeps
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Awesome Mountain Views at this Studio with Loft, holiday rental in Shaftsbury

Awesome Mountain Views at this Studio with Loft

2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Private Retreat on Battenkill Near Manchester Village, holiday rental in Shaftsbury

Private Retreat on Battenkill Near Manchester Village

5 bedrooms
5 bathrooms
Sleeps 9
Match: Sleeps
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Cozy 1 Bedroom farm stay cottage, holiday rental in Shaftsbury

Cozy 1 Bedroom farm stay cottage

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Stunning Views of the Equinox, holiday rental in Shaftsbury

Stunning Views of the Equinox

5 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Karin's Place, holiday rental in Shaftsbury

Karin's Place

7 bedrooms
6 bathrooms
Sleeps 20
Match: Sleeps
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Mountain Retreat - Chimney Hill - 7 Miles to Mount Snow - direct VAST access, holiday rental in Shaftsbury

Mountain Retreat - Chimney Hill - 7 Miles to Mount Snow - direct VAST access

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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The Lodge at Fox Hollow, holiday rental in Shaftsbury

The Lodge at Fox Hollow

2 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
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Tentrr Signature Site - Fortunate Ewe Farm, holiday rental in Shaftsbury

Tentrr Signature Site - Fortunate Ewe Farm

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Tentrr Signature Site - Runamuk Farm, holiday rental in Shaftsbury

Tentrr Signature Site - Runamuk Farm

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Meme's High Mountain Lake House, holiday rental in Shaftsbury

Meme's High Mountain Lake House

3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Two Brooks Lodge, holiday rental in Shaftsbury

Two Brooks Lodge

3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Unique Vermont Log Cabin Nestled in Red Mountains

0 bedrooms
0 bathrooms
Sleeps 0
Match: Sleeps
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Tentrr Signature Site - Bargate Trail Tent at Sky Parlor Farm, holiday rental in Shaftsbury

Tentrr Signature Site - Bargate Trail Tent at Sky Parlor Farm

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Tentrr Signature Site - Grateful Acres Vermont, holiday rental in Shaftsbury

Tentrr Signature Site - Grateful Acres Vermont

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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