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Southfield Vacation Rentals

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Bedrooms

Bathrooms

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5 mi
48 rentals in Southfield.
Cozy escape in the trees of the Berkshires, vacation rental in Southfield
Cozy escape in the trees of the Berkshires, vacation rental in Southfield
Cozy escape in the trees of the Berkshires, vacation rental in Southfield

Cozy escape in the trees of the Berkshires

Rental Home
5 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Modern Farmhouse in the Southern Berkshires, vacation rental in Southfield
Modern Farmhouse in the Southern Berkshires, vacation rental in Southfield
Modern Farmhouse in the Southern Berkshires, vacation rental in Southfield

Modern Farmhouse in the Southern Berkshires

Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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The following properties within 20 miles of Southfield match all your filters:
Stay at Beaver Lodge!, vacation rental in Southfield
Stay at Beaver Lodge!, vacation rental in Southfield
Stay at Beaver Lodge!, vacation rental in Southfield

Stay at Beaver Lodge!

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Waterfront oasis in heart of Berkshires, vacation rental in Southfield
Waterfront oasis in heart of Berkshires, vacation rental in Southfield
Waterfront oasis in heart of Berkshires, vacation rental in Southfield

Waterfront oasis in heart of Berkshires

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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'The Mill River Cabin’ w/ Fireplace & River View!, vacation rental in Southfield
'The Mill River Cabin’ w/ Fireplace & River View!, vacation rental in Southfield
'The Mill River Cabin’ w/ Fireplace & River View!, vacation rental in Southfield

'The Mill River Cabin’ w/ Fireplace & River View!

Rental Home
4 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Rustic Berkshires Cottage at Lake Buel w/ Kayaks!, vacation rental in Southfield
Rustic Berkshires Cottage at Lake Buel w/ Kayaks!, vacation rental in Southfield
Rustic Berkshires Cottage at Lake Buel w/ Kayaks!, vacation rental in Southfield

Rustic Berkshires Cottage at Lake Buel w/ Kayaks!

Rental Home
2 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
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Perfect Vacation Get Away - Historical New Marlborough, vacation rental in Southfield
Perfect Vacation Get Away - Historical New Marlborough, vacation rental in Southfield
Perfect Vacation Get Away - Historical New Marlborough, vacation rental in Southfield

Perfect Vacation Get Away - Historical New Marlborough

Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Romantic weekend getaway!, vacation rental in Southfield
Romantic weekend getaway!, vacation rental in Southfield
Romantic weekend getaway!, vacation rental in Southfield

Romantic weekend getaway!

Rental Home
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Gorgeous Sheffield Home in Heart of Berkshires, vacation rental in Southfield
Gorgeous Sheffield Home in Heart of Berkshires, vacation rental in Southfield
Gorgeous Sheffield Home in Heart of Berkshires, vacation rental in Southfield

Gorgeous Sheffield Home in Heart of Berkshires

Rental Home
5 bedrooms
4 bathrooms
Sleeps 15
Match: Sleeps
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Quiet rustic cottage with shared lake access, vacation rental in Southfield
Quiet rustic cottage with shared lake access, vacation rental in Southfield
Quiet rustic cottage with shared lake access, vacation rental in Southfield

Quiet rustic cottage with shared lake access

Rental Home
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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5-bed Colonial Berkshires Farmhouse, aka Grandaddy's House, Family Friendly home, vacation rental in Southfield
5-bed Colonial Berkshires Farmhouse, aka Grandaddy's House, Family Friendly home, vacation rental in Southfield
5-bed Colonial Berkshires Farmhouse, aka Grandaddy's House, Family Friendly home, vacation rental in Southfield

5-bed Colonial Berkshires Farmhouse, aka Grandaddy's House, Family Friendly home

Rental Home
5 bedrooms
4 bathrooms
Sleeps 11
Match: Sleeps
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Romantic and Secluded Berkshire's Gem, vacation rental in Southfield
Romantic and Secluded Berkshire's Gem, vacation rental in Southfield
Romantic and Secluded Berkshire's Gem, vacation rental in Southfield

Romantic and Secluded Berkshire's Gem

Rental Home
4 bedrooms
2 bathrooms
Sleeps 12
Match: Sleeps
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Cabin in the woods w cedar Hot Tub + private pond, vacation rental in Southfield
Cabin in the woods w cedar Hot Tub + private pond, vacation rental in Southfield
Cabin in the woods w cedar Hot Tub + private pond, vacation rental in Southfield

Cabin in the woods w cedar Hot Tub + private pond

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Charming Cottage, New Marlborough Village Green in the Berkshires, vacation rental in Southfield
Charming Cottage, New Marlborough Village Green in the Berkshires, vacation rental in Southfield
Charming Cottage, New Marlborough Village Green in the Berkshires, vacation rental in Southfield

Charming Cottage, New Marlborough Village Green in the Berkshires

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Cozy Cabin in the Berkshires, vacation rental in Southfield
Cozy Cabin in the Berkshires, vacation rental in Southfield
Cozy Cabin in the Berkshires, vacation rental in Southfield

Cozy Cabin in the Berkshires

Rental Home
2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Lake Community - Near Town, Attractions, vacation rental in Southfield
Lake Community - Near Town, Attractions, vacation rental in Southfield
Lake Community - Near Town, Attractions, vacation rental in Southfield

Lake Community - Near Town, Attractions

Rental Home
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Peaceful, Post and Beam Loft, Sleeps 9, vacation rental in Southfield
Peaceful, Post and Beam Loft, Sleeps 9, vacation rental in Southfield
Peaceful, Post and Beam Loft, Sleeps 9, vacation rental in Southfield

Peaceful, Post and Beam Loft, Sleeps 9

Rental Home
2 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
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Meadow Top Cottage: beautiful mountain views, vacation rental in Southfield
Meadow Top Cottage: beautiful mountain views, vacation rental in Southfield
Meadow Top Cottage: beautiful mountain views, vacation rental in Southfield

Meadow Top Cottage: beautiful mountain views

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Beautiful Berkshire rental, rustic elegance, August through fall, vacation rental in Southfield
Beautiful Berkshire rental, rustic elegance, August through fall, vacation rental in Southfield
Beautiful Berkshire rental, rustic elegance, August through fall, vacation rental in Southfield

Beautiful Berkshire rental, rustic elegance, August through fall

Rental Home
3 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Charming Ashley Falls Getaway, vacation rental in Southfield
Charming Ashley Falls Getaway, vacation rental in Southfield
Charming Ashley Falls Getaway, vacation rental in Southfield

Charming Ashley Falls Getaway

Rental Home
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Beautiful Berkshire classic home nestled in a quiet peaceful area, vacation rental in Southfield
Beautiful Berkshire classic home nestled in a quiet peaceful area, vacation rental in Southfield
Beautiful Berkshire classic home nestled in a quiet peaceful area, vacation rental in Southfield

Beautiful Berkshire classic home nestled in a quiet peaceful area

Rental Home
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Elegant Lake Buel Home, vacation rental in Southfield
Elegant Lake Buel Home, vacation rental in Southfield
Elegant Lake Buel Home, vacation rental in Southfield

Elegant Lake Buel Home

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Converted Berkshire schoolhouse on a quiet river, vacation rental in Southfield
Converted Berkshire schoolhouse on a quiet river, vacation rental in Southfield
Converted Berkshire schoolhouse on a quiet river, vacation rental in Southfield

Converted Berkshire schoolhouse on a quiet river

Rental Home
3 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Konkapot Cottage, Pastoral Bliss With Wide Views, vacation rental in Southfield
Konkapot Cottage, Pastoral Bliss With Wide Views, vacation rental in Southfield
Konkapot Cottage, Pastoral Bliss With Wide Views, vacation rental in Southfield

Konkapot Cottage, Pastoral Bliss With Wide Views

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Enjoy Winter in the Berkshires at this cozy private getaway, vacation rental in Southfield
Enjoy Winter in the Berkshires at this cozy private getaway, vacation rental in Southfield
Enjoy Winter in the Berkshires at this cozy private getaway, vacation rental in Southfield

Enjoy Winter in the Berkshires at this cozy private getaway

Rental Home
4 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
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Pine View Cottage, Berkshires Getaway Lake Buel w/ lake rights. Pet friendly!, vacation rental in Southfield
Pine View Cottage, Berkshires Getaway Lake Buel w/ lake rights. Pet friendly!, vacation rental in Southfield
Pine View Cottage, Berkshires Getaway Lake Buel w/ lake rights. Pet friendly!, vacation rental in Southfield

Pine View Cottage, Berkshires Getaway Lake Buel w/ lake rights. Pet friendly!

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Private Woodland Getaway minutes from Ski Butternut, vacation rental in Southfield
Private Woodland Getaway minutes from Ski Butternut, vacation rental in Southfield
Private Woodland Getaway minutes from Ski Butternut, vacation rental in Southfield

Private Woodland Getaway minutes from Ski Butternut

Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Fickle Fox Farm.  Leaf Peepers and Skiers! This is your season., vacation rental in Southfield
Fickle Fox Farm.  Leaf Peepers and Skiers! This is your season., vacation rental in Southfield
Fickle Fox Farm.  Leaf Peepers and Skiers! This is your season., vacation rental in Southfield

Fickle Fox Farm. Leaf Peepers and Skiers! This is your season.

Rental Home
4 bedrooms
3 bathrooms
Sleeps 11
Match: Sleeps
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1847 New Marlborough Farmhouse. a 4-BR home right in our quiet village., vacation rental in Southfield
1847 New Marlborough Farmhouse. a 4-BR home right in our quiet village., vacation rental in Southfield
1847 New Marlborough Farmhouse. a 4-BR home right in our quiet village., vacation rental in Southfield

1847 New Marlborough Farmhouse. a 4-BR home right in our quiet village.

Rental Home
4 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
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sweet dreams retreat, vacation rental in Southfield
sweet dreams retreat, vacation rental in Southfield
sweet dreams retreat, vacation rental in Southfield

sweet dreams retreat

Rental Home
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
More info
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Renovated Lakefront House w/ Dock: Pets Welcome!, vacation rental in Southfield
Renovated Lakefront House w/ Dock: Pets Welcome!, vacation rental in Southfield
Renovated Lakefront House w/ Dock: Pets Welcome!, vacation rental in Southfield

Renovated Lakefront House w/ Dock: Pets Welcome!

Rental Home
5 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Luxurious Mountain Retreat - Private 40-Acre Family Haven, vacation rental in Southfield
Luxurious Mountain Retreat - Private 40-Acre Family Haven, vacation rental in Southfield
Luxurious Mountain Retreat - Private 40-Acre Family Haven, vacation rental in Southfield

Luxurious Mountain Retreat - Private 40-Acre Family Haven

Rental Home
4 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
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1700s Farmhouse with Modern Amenities and Comfort. Pool, Hot Tub, Views., vacation rental in Southfield
1700s Farmhouse with Modern Amenities and Comfort. Pool, Hot Tub, Views., vacation rental in Southfield
1700s Farmhouse with Modern Amenities and Comfort. Pool, Hot Tub, Views., vacation rental in Southfield

1700s Farmhouse with Modern Amenities and Comfort. Pool, Hot Tub, Views.

Rental Home
4 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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Spacious, Modern House 5 Bedrooms, 2.5 Bathrooms, Sleep 12 on small horse farm., vacation rental in Southfield
Spacious, Modern House 5 Bedrooms, 2.5 Bathrooms, Sleep 12 on small horse farm., vacation rental in Southfield
Spacious, Modern House 5 Bedrooms, 2.5 Bathrooms, Sleep 12 on small horse farm., vacation rental in Southfield

Spacious, Modern House 5 Bedrooms, 2.5 Bathrooms, Sleep 12 on small horse farm.

Rental Home
5 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Canaan Valley Home, A Berkshires Getaway, vacation rental in Southfield
Canaan Valley Home, A Berkshires Getaway, vacation rental in Southfield
Canaan Valley Home, A Berkshires Getaway, vacation rental in Southfield

Canaan Valley Home, A Berkshires Getaway

Rental Home
4 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
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Lake Buel Lakefront - 4 Bedrooms with private dock, vacation rental in Southfield
Lake Buel Lakefront - 4 Bedrooms with private dock, vacation rental in Southfield
Lake Buel Lakefront - 4 Bedrooms with private dock, vacation rental in Southfield

Lake Buel Lakefront - 4 Bedrooms with private dock

Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
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Beautiful farmhouse for perfect country escape - close to skiing, 5 fireplaces., vacation rental in Southfield
Beautiful farmhouse for perfect country escape - close to skiing, 5 fireplaces., vacation rental in Southfield
Beautiful farmhouse for perfect country escape - close to skiing, 5 fireplaces., vacation rental in Southfield

Beautiful farmhouse for perfect country escape - close to skiing, 5 fireplaces.

Rental Home
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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LAKE FRONT LAKE BUEL Monterey 10 M GREAT BARRINGTON HOUSE VIEWS PRIVATE DOCK, vacation rental in Southfield
LAKE FRONT LAKE BUEL Monterey 10 M GREAT BARRINGTON HOUSE VIEWS PRIVATE DOCK, vacation rental in Southfield
LAKE FRONT LAKE BUEL Monterey 10 M GREAT BARRINGTON HOUSE VIEWS PRIVATE DOCK, vacation rental in Southfield

LAKE FRONT LAKE BUEL Monterey 10 M GREAT BARRINGTON HOUSE VIEWS PRIVATE DOCK

Rental Home
6 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Ski Relax Enjoy the Berkshires! Sparkling, New, Open and Spacious!, vacation rental in Southfield
Ski Relax Enjoy the Berkshires! Sparkling, New, Open and Spacious!, vacation rental in Southfield
Ski Relax Enjoy the Berkshires! Sparkling, New, Open and Spacious!, vacation rental in Southfield

Ski Relax Enjoy the Berkshires! Sparkling, New, Open and Spacious!

Rental Home
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Serenity Summit: Hot Tub, Mountain Views, Book Now, vacation rental in Southfield
Serenity Summit: Hot Tub, Mountain Views, Book Now, vacation rental in Southfield
Serenity Summit: Hot Tub, Mountain Views, Book Now, vacation rental in Southfield

Serenity Summit: Hot Tub, Mountain Views, Book Now

Rental Home
5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
More info
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Relaxing retreat in the Berkshires! Perfect for outdoor enthusiast!, vacation rental in Southfield
Relaxing retreat in the Berkshires! Perfect for outdoor enthusiast!, vacation rental in Southfield
Relaxing retreat in the Berkshires! Perfect for outdoor enthusiast!, vacation rental in Southfield

Relaxing retreat in the Berkshires! Perfect for outdoor enthusiast!

Rental Home
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
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Steepletop: Nature Lover’s Paradise w/Rec Room, vacation rental in Southfield
Steepletop: Nature Lover’s Paradise w/Rec Room, vacation rental in Southfield
Steepletop: Nature Lover’s Paradise w/Rec Room, vacation rental in Southfield

Steepletop: Nature Lover’s Paradise w/Rec Room

Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Relax, Read, Entertain, Or Walk To West Lake From Our Berkshire Home., vacation rental in Southfield
Relax, Read, Entertain, Or Walk To West Lake From Our Berkshire Home., vacation rental in Southfield
Relax, Read, Entertain, Or Walk To West Lake From Our Berkshire Home., vacation rental in Southfield

Relax, Read, Entertain, Or Walk To West Lake From Our Berkshire Home.

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Spacious 4-bedroom house in peaceful Southfield with AC, WiFi and more!, vacation rental in Southfield
Spacious 4-bedroom house in peaceful Southfield with AC, WiFi and more!, vacation rental in Southfield
Spacious 4-bedroom house in peaceful Southfield with AC, WiFi and more!, vacation rental in Southfield

Spacious 4-bedroom house in peaceful Southfield with AC, WiFi and more!

Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
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Beautiful Berkshire Home - Enjoy summer, fall & winter attractions, vacation rental in Southfield
Beautiful Berkshire Home - Enjoy summer, fall & winter attractions, vacation rental in Southfield
Beautiful Berkshire Home - Enjoy summer, fall & winter attractions, vacation rental in Southfield

Beautiful Berkshire Home - Enjoy summer, fall & winter attractions

Rental Home
4 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
More info
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Waterfront Cottage 10 Min From Great Barrington, vacation rental in Southfield
Waterfront Cottage 10 Min From Great Barrington, vacation rental in Southfield
Waterfront Cottage 10 Min From Great Barrington, vacation rental in Southfield

Waterfront Cottage 10 Min From Great Barrington

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Bygone era Lake Buel cottage with access to shared dock and canoe, vacation rental in Southfield
Bygone era Lake Buel cottage with access to shared dock and canoe, vacation rental in Southfield
Bygone era Lake Buel cottage with access to shared dock and canoe, vacation rental in Southfield

Bygone era Lake Buel cottage with access to shared dock and canoe

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Meadow Top Cottage: Countryside Cottage on 72 Acres, vacation rental in Southfield
Meadow Top Cottage: Countryside Cottage on 72 Acres, vacation rental in Southfield
Meadow Top Cottage: Countryside Cottage on 72 Acres, vacation rental in Southfield

Meadow Top Cottage: Countryside Cottage on 72 Acres

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Showing results 1-48 of 48
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