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Spencertown Holiday Apartments

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50 rentals in Spencertown.
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Modern Cozy Wooded Retreat On 30 Private Acres, holiday rental in Spencertown
Modern Cozy Wooded Retreat On 30 Private Acres, holiday rental in Spencertown
Modern Cozy Wooded Retreat On 30 Private Acres, holiday rental in Spencertown

Modern Cozy Wooded Retreat On 30 Private Acres

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Modern Cozy Wooded Retreat, holiday rental in Spencertown
Modern Cozy Wooded Retreat, holiday rental in Spencertown
Modern Cozy Wooded Retreat, holiday rental in Spencertown

Modern Cozy Wooded Retreat

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
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Hudson Valley Berkshires Cottage, holiday rental in Spencertown
Hudson Valley Berkshires Cottage, holiday rental in Spencertown
Hudson Valley Berkshires Cottage, holiday rental in Spencertown

Hudson Valley Berkshires Cottage

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Suite 3 - Quiet and private accommodations in a country setting., holiday rental in Spencertown
Suite 3 - Quiet and private accommodations in a country setting., holiday rental in Spencertown
Suite 3 - Quiet and private accommodations in a country setting., holiday rental in Spencertown

Suite 3 - Quiet and private accommodations in a country setting.

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
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Suite 4 - Quiet and private accommodations in a country setting., holiday rental in Spencertown
Suite 4 - Quiet and private accommodations in a country setting., holiday rental in Spencertown
Suite 4 - Quiet and private accommodations in a country setting., holiday rental in Spencertown

Suite 4 - Quiet and private accommodations in a country setting.

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
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Suite 1 - Quiet and private accommodations in a country setting., holiday rental in Spencertown
Suite 1 - Quiet and private accommodations in a country setting., holiday rental in Spencertown
Suite 1 - Quiet and private accommodations in a country setting., holiday rental in Spencertown

Suite 1 - Quiet and private accommodations in a country setting.

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
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Suite 2 - Quiet and private accommodations in a country setting., holiday rental in Spencertown
Suite 2 - Quiet and private accommodations in a country setting., holiday rental in Spencertown
Suite 2 - Quiet and private accommodations in a country setting., holiday rental in Spencertown

Suite 2 - Quiet and private accommodations in a country setting.

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
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Suite 5 - Quiet and private accommodations in a country setting., holiday rental in Spencertown
Suite 5 - Quiet and private accommodations in a country setting., holiday rental in Spencertown
Suite 5 - Quiet and private accommodations in a country setting., holiday rental in Spencertown

Suite 5 - Quiet and private accommodations in a country setting.

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
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Beauty in the Berkshires .., holiday rental in Spencertown
Beauty in the Berkshires .., holiday rental in Spencertown
Beauty in the Berkshires .., holiday rental in Spencertown

Beauty in the Berkshires ..

Holiday Rental House
6 bedrooms
5 bathrooms
Sleeps 16
Match: Sleeps
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CHARMING, VIEWS For Miles, Come RELAX, Go Hiking!, holiday rental in Spencertown
CHARMING, VIEWS For Miles, Come RELAX, Go Hiking!, holiday rental in Spencertown
CHARMING, VIEWS For Miles, Come RELAX, Go Hiking!, holiday rental in Spencertown

CHARMING, VIEWS For Miles, Come RELAX, Go Hiking!

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Charming, Quiet, Modern, Wooded, River Front, holiday rental in Spencertown
Charming, Quiet, Modern, Wooded, River Front, holiday rental in Spencertown
Charming, Quiet, Modern, Wooded, River Front, holiday rental in Spencertown

Charming, Quiet, Modern, Wooded, River Front

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 13
Match: Sleeps
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Close to Skiing Heated Pool /Hot Tub/20 acres/Fiber Optic/Chef by Arrangement, holiday rental in Spencertown
Close to Skiing Heated Pool /Hot Tub/20 acres/Fiber Optic/Chef by Arrangement, holiday rental in Spencertown
Close to Skiing Heated Pool /Hot Tub/20 acres/Fiber Optic/Chef by Arrangement, holiday rental in Spencertown

Close to Skiing Heated Pool /Hot Tub/20 acres/Fiber Optic/Chef by Arrangement

Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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Quiet Guest House In The Green River Valley, holiday rental in Spencertown
Quiet Guest House In The Green River Valley, holiday rental in Spencertown
Quiet Guest House In The Green River Valley, holiday rental in Spencertown

Quiet Guest House In The Green River Valley

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Welcome to WIndswept Acres in the Berkshire Mts!, holiday rental in Spencertown
Welcome to WIndswept Acres in the Berkshire Mts!, holiday rental in Spencertown
Welcome to WIndswept Acres in the Berkshire Mts!, holiday rental in Spencertown

Welcome to WIndswept Acres in the Berkshire Mts!

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Two Rooms with En-Suite in Quiet Woodland, holiday rental in Spencertown
Two Rooms with En-Suite in Quiet Woodland, holiday rental in Spencertown
Two Rooms with En-Suite in Quiet Woodland, holiday rental in Spencertown

Two Rooms with En-Suite in Quiet Woodland

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Modern Rustic Artist's Getaway, holiday rental in Spencertown
Modern Rustic Artist's Getaway, holiday rental in Spencertown
Modern Rustic Artist's Getaway, holiday rental in Spencertown

Modern Rustic Artist's Getaway

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Austerlitz , New York, Columbia County, holiday rental in Spencertown
Austerlitz , New York, Columbia County, holiday rental in Spencertown
Austerlitz , New York, Columbia County, holiday rental in Spencertown

Austerlitz , New York, Columbia County

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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��HUDSON VALLEY ENTIRE HOUSE RENTAL��, holiday rental in Spencertown
��HUDSON VALLEY ENTIRE HOUSE RENTAL��, holiday rental in Spencertown
��HUDSON VALLEY ENTIRE HOUSE RENTAL��, holiday rental in Spencertown

��HUDSON VALLEY ENTIRE HOUSE RENTAL��

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Relax in the Country - Peace, quiet and family friendly, holiday rental in Spencertown
Relax in the Country - Peace, quiet and family friendly, holiday rental in Spencertown
Relax in the Country - Peace, quiet and family friendly, holiday rental in Spencertown

Relax in the Country - Peace, quiet and family friendly

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Cozy apartment overlooking our small farm.  Family Friendly., holiday rental in Spencertown
Cozy apartment overlooking our small farm.  Family Friendly., holiday rental in Spencertown
Cozy apartment overlooking our small farm.  Family Friendly., holiday rental in Spencertown

Cozy apartment overlooking our small farm. Family Friendly.

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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The Pinetop Cabin | Modern ∙ Surrounded by Trees ∙ Sustainably-built, holiday rental in Spencertown
The Pinetop Cabin | Modern ∙ Surrounded by Trees ∙ Sustainably-built, holiday rental in Spencertown
The Pinetop Cabin | Modern ∙ Surrounded by Trees ∙ Sustainably-built, holiday rental in Spencertown

The Pinetop Cabin | Modern ∙ Surrounded by Trees ∙ Sustainably-built

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Secluded Family-Friendly Home, holiday rental in Spencertown
Secluded Family-Friendly Home, holiday rental in Spencertown
Secluded Family-Friendly Home, holiday rental in Spencertown

Secluded Family-Friendly Home

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Hillhouse Log Cabin, holiday rental in Spencertown
Hillhouse Log Cabin, holiday rental in Spencertown
Hillhouse Log Cabin, holiday rental in Spencertown

Hillhouse Log Cabin

Cabin Holiday Rental
3 bedrooms
2 bathrooms
Sleeps 13
Match: Sleeps
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Total Privacy! Tanglewood Retreat With Berkshire Views!, holiday rental in Spencertown
Total Privacy! Tanglewood Retreat With Berkshire Views!, holiday rental in Spencertown
Total Privacy! Tanglewood Retreat With Berkshire Views!, holiday rental in Spencertown

Total Privacy! Tanglewood Retreat With Berkshire Views!

Holiday Rental House
5 bedrooms
5 bathrooms
Sleeps 14
Match: Sleeps
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NEW! Clean & Cozy Hillsdale Cabin, minutes to Catamount, Tanglewood, holiday rental in Spencertown
NEW! Clean & Cozy Hillsdale Cabin, minutes to Catamount, Tanglewood, holiday rental in Spencertown
NEW! Clean & Cozy Hillsdale Cabin, minutes to Catamount, Tanglewood, holiday rental in Spencertown

NEW! Clean & Cozy Hillsdale Cabin, minutes to Catamount, Tanglewood

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Home Sweet Home in a Best Place to Live Locale, holiday rental in Spencertown
Home Sweet Home in a Best Place to Live Locale, holiday rental in Spencertown
Home Sweet Home in a Best Place to Live Locale, holiday rental in Spencertown

Home Sweet Home in a Best Place to Live Locale

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Ski House -charming house near Catamount/Butternut/ Jiminy Peak, holiday rental in Spencertown
Ski House -charming house near Catamount/Butternut/ Jiminy Peak, holiday rental in Spencertown
Ski House -charming house near Catamount/Butternut/ Jiminy Peak, holiday rental in Spencertown

Ski House -charming house near Catamount/Butternut/ Jiminy Peak

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Serene Berkshires Family Vacation Rental  on 45 Acres, holiday rental in Spencertown
Serene Berkshires Family Vacation Rental  on 45 Acres, holiday rental in Spencertown
Serene Berkshires Family Vacation Rental  on 45 Acres, holiday rental in Spencertown

Serene Berkshires Family Vacation Rental on 45 Acres

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Berkshires Hudson Valley View Cottage - Private & Quiet, holiday rental in Spencertown
Berkshires Hudson Valley View Cottage - Private & Quiet, holiday rental in Spencertown
Berkshires Hudson Valley View Cottage - Private & Quiet, holiday rental in Spencertown

Berkshires Hudson Valley View Cottage - Private & Quiet

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Chalet near 4 ski resorts with hot tub, holiday rental in Spencertown
Chalet near 4 ski resorts with hot tub, holiday rental in Spencertown
Chalet near 4 ski resorts with hot tub, holiday rental in Spencertown

Chalet near 4 ski resorts with hot tub

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Spacious secluded  yet close to everything, holiday rental in Spencertown
Spacious secluded  yet close to everything, holiday rental in Spencertown
Spacious secluded  yet close to everything, holiday rental in Spencertown

Spacious secluded yet close to everything

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Tranquil Berkshires Retreat, holiday rental in Spencertown
Tranquil Berkshires Retreat, holiday rental in Spencertown
Tranquil Berkshires Retreat, holiday rental in Spencertown

Tranquil Berkshires Retreat

Holiday Rental House
6 bedrooms
7 bathrooms
Sleeps 11
Match: Sleeps
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Tentrr Signature Site - The Lodge's Campsite, holiday rental in Spencertown
Tentrr Signature Site - The Lodge's Campsite, holiday rental in Spencertown
Tentrr Signature Site - The Lodge's Campsite, holiday rental in Spencertown

Tentrr Signature Site - The Lodge's Campsite

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
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Private Vacation Getaway - Berkshires, holiday rental in Spencertown
Private Vacation Getaway - Berkshires, holiday rental in Spencertown
Private Vacation Getaway - Berkshires, holiday rental in Spencertown

Private Vacation Getaway - Berkshires

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Enchanting Country House on 18 acres, Sunset Views, <15 minutes from Tanglewood, holiday rental in Spencertown
Enchanting Country House on 18 acres, Sunset Views, <15 minutes from Tanglewood, holiday rental in Spencertown
Enchanting Country House on 18 acres, Sunset Views, <15 minutes from Tanglewood, holiday rental in Spencertown

Enchanting Country House on 18 acres, Sunset Views, <15 minutes from Tanglewood

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Cute little ranch in the country, holiday rental in Spencertown
Cute little ranch in the country, holiday rental in Spencertown
Cute little ranch in the country, holiday rental in Spencertown

Cute little ranch in the country

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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NEW! Austerlitz Home w/ Updated Interior + Porch!, holiday rental in Spencertown
NEW! Austerlitz Home w/ Updated Interior + Porch!, holiday rental in Spencertown
NEW! Austerlitz Home w/ Updated Interior + Porch!, holiday rental in Spencertown

NEW! Austerlitz Home w/ Updated Interior + Porch!

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Midcentury modern retreat nestled between Hudson Valley and The Berkshires!, holiday rental in Spencertown
Midcentury modern retreat nestled between Hudson Valley and The Berkshires!, holiday rental in Spencertown
Midcentury modern retreat nestled between Hudson Valley and The Berkshires!, holiday rental in Spencertown

Midcentury modern retreat nestled between Hudson Valley and The Berkshires!

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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THRILLING Mountain VIEWS, Modern Farmhouse, holiday rental in Spencertown
THRILLING Mountain VIEWS, Modern Farmhouse, holiday rental in Spencertown
THRILLING Mountain VIEWS, Modern Farmhouse, holiday rental in Spencertown

THRILLING Mountain VIEWS, Modern Farmhouse

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Open GOURMET Kitchen, THRILLING Views, holiday rental in Spencertown
Open GOURMET Kitchen, THRILLING Views, holiday rental in Spencertown
Open GOURMET Kitchen, THRILLING Views, holiday rental in Spencertown

Open GOURMET Kitchen, THRILLING Views

Holiday Rental House
6 bedrooms
4 bathrooms
Sleeps 14
Match: Sleeps
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Fog Hill Cabin is a peaceful retreat set among a wooded landscape., holiday rental in Spencertown
Fog Hill Cabin is a peaceful retreat set among a wooded landscape., holiday rental in Spencertown
Fog Hill Cabin is a peaceful retreat set among a wooded landscape., holiday rental in Spencertown

Fog Hill Cabin is a peaceful retreat set among a wooded landscape.

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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The Upstate Cabin: A secluded getaway in the woods, holiday rental in Spencertown
The Upstate Cabin: A secluded getaway in the woods, holiday rental in Spencertown
The Upstate Cabin: A secluded getaway in the woods, holiday rental in Spencertown

The Upstate Cabin: A secluded getaway in the woods

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Cozy Loft on a Country Road, holiday rental in Spencertown
Cozy Loft on a Country Road, holiday rental in Spencertown
Cozy Loft on a Country Road, holiday rental in Spencertown

Cozy Loft on a Country Road

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
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Award-winning architectural gem, 17 acres, swimming pond, sited in state forest, holiday rental in Spencertown
Award-winning architectural gem, 17 acres, swimming pond, sited in state forest, holiday rental in Spencertown
Award-winning architectural gem, 17 acres, swimming pond, sited in state forest, holiday rental in Spencertown

Award-winning architectural gem, 17 acres, swimming pond, sited in state forest

Holiday Rental House
4 bedrooms
6 bathrooms
Sleeps 4
Match: Sleeps
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Entire Chalet-Style Stunner on a Country Road, holiday rental in Spencertown
Entire Chalet-Style Stunner on a Country Road, holiday rental in Spencertown
Entire Chalet-Style Stunner on a Country Road, holiday rental in Spencertown

Entire Chalet-Style Stunner on a Country Road

Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Serene Hillsdale Cottage Amped with Tech and Wifi, holiday rental in Spencertown
Serene Hillsdale Cottage Amped with Tech and Wifi, holiday rental in Spencertown
Serene Hillsdale Cottage Amped with Tech and Wifi, holiday rental in Spencertown

Serene Hillsdale Cottage Amped with Tech and Wifi

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Chalet-Style Stunner on a Country Road, holiday rental in Spencertown
Chalet-Style Stunner on a Country Road, holiday rental in Spencertown
Chalet-Style Stunner on a Country Road, holiday rental in Spencertown

Chalet-Style Stunner on a Country Road

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Dream getaway - mtn views, ski, pool, deck, nearby lake, work from home setups, holiday rental in Spencertown
Dream getaway - mtn views, ski, pool, deck, nearby lake, work from home setups, holiday rental in Spencertown
Dream getaway - mtn views, ski, pool, deck, nearby lake, work from home setups, holiday rental in Spencertown

Dream getaway - mtn views, ski, pool, deck, nearby lake, work from home setups

Holiday Rental House
6 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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19th Century Farm House on 300 Acre Farm, holiday rental in Spencertown
19th Century Farm House on 300 Acre Farm, holiday rental in Spencertown
19th Century Farm House on 300 Acre Farm, holiday rental in Spencertown

19th Century Farm House on 300 Acre Farm

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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CHALET-STYLE STUNNER ON A COUNTRY ROAD, holiday rental in Spencertown
CHALET-STYLE STUNNER ON A COUNTRY ROAD, holiday rental in Spencertown
CHALET-STYLE STUNNER ON A COUNTRY ROAD, holiday rental in Spencertown

CHALET-STYLE STUNNER ON A COUNTRY ROAD

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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