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Southwick Vacation Rentals

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49 rentals in Southwick.
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Serene & cozy lakefront getaway on Congamond's pristine North Pond, vacation rental in Southwick
Serene & cozy lakefront getaway on Congamond's pristine North Pond, vacation rental in Southwick
Serene & cozy lakefront getaway on Congamond's pristine North Pond, vacation rental in Southwick

Serene & cozy lakefront getaway on Congamond's pristine North Pond

Rental Home
3 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
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Fully renovated lakeview Cottage, Southwick,  MA, vacation rental in Southwick
Fully renovated lakeview Cottage, Southwick,  MA, vacation rental in Southwick
Fully renovated lakeview Cottage, Southwick,  MA, vacation rental in Southwick

Fully renovated lakeview Cottage, Southwick, MA

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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ISLAND WATERFRONT Sleeps up to 8, vacation rental in Southwick
ISLAND WATERFRONT Sleeps up to 8, vacation rental in Southwick
ISLAND WATERFRONT Sleeps up to 8, vacation rental in Southwick

ISLAND WATERFRONT Sleeps up to 8

Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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4Br/3bath Lakefront/Ski House in Berkshires. Fully fitted kitchen. Hi speed wifi, vacation rental in Southwick
4Br/3bath Lakefront/Ski House in Berkshires. Fully fitted kitchen. Hi speed wifi, vacation rental in Southwick
4Br/3bath Lakefront/Ski House in Berkshires. Fully fitted kitchen. Hi speed wifi, vacation rental in Southwick

4Br/3bath Lakefront/Ski House in Berkshires. Fully fitted kitchen. Hi speed wifi

Rental Home
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Big farmhouse in the foothills of the Berkshires, vacation rental in Southwick
Big farmhouse in the foothills of the Berkshires, vacation rental in Southwick
Big farmhouse in the foothills of the Berkshires, vacation rental in Southwick

Big farmhouse in the foothills of the Berkshires

Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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The Loft * Lost Acres ~ A Peaceful Rural Escape on a Farm Winery!, vacation rental in Southwick
The Loft * Lost Acres ~ A Peaceful Rural Escape on a Farm Winery!, vacation rental in Southwick
The Loft * Lost Acres ~ A Peaceful Rural Escape on a Farm Winery!, vacation rental in Southwick

The Loft * Lost Acres ~ A Peaceful Rural Escape on a Farm Winery!

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Luxurious rural get away, vacation rental in Southwick
Luxurious rural get away, vacation rental in Southwick
Luxurious rural get away, vacation rental in Southwick

Luxurious rural get away

Rental Home
6 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
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Mountain View: 48 hours between bookings., vacation rental in Southwick
Mountain View: 48 hours between bookings., vacation rental in Southwick
Mountain View: 48 hours between bookings., vacation rental in Southwick

Mountain View: 48 hours between bookings.

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Bamboo:  48 hours between bookings., vacation rental in Southwick
Bamboo:  48 hours between bookings., vacation rental in Southwick
Bamboo:  48 hours between bookings., vacation rental in Southwick

Bamboo: 48 hours between bookings.

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Spacious waterfront Berkshire home family private get-away, vacation rental in Southwick
Spacious waterfront Berkshire home family private get-away, vacation rental in Southwick
Spacious waterfront Berkshire home family private get-away, vacation rental in Southwick

Spacious waterfront Berkshire home family private get-away

Rental Home
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Modern Berkshires Cottage  � Gas Stove, Large Deck & W/D + 7 mins to Otis Ridge, vacation rental in Southwick
Modern Berkshires Cottage  � Gas Stove, Large Deck & W/D + 7 mins to Otis Ridge, vacation rental in Southwick
Modern Berkshires Cottage  � Gas Stove, Large Deck & W/D + 7 mins to Otis Ridge, vacation rental in Southwick

Modern Berkshires Cottage � Gas Stove, Large Deck & W/D + 7 mins to Otis Ridge

Rental Home
3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Dee's  Granby Staycation  ! Convenient location, New Gameroom, Charming interior, vacation rental in Southwick
Dee's  Granby Staycation  ! Convenient location, New Gameroom, Charming interior, vacation rental in Southwick
Dee's  Granby Staycation  ! Convenient location, New Gameroom, Charming interior, vacation rental in Southwick

Dee's Granby Staycation ! Convenient location, New Gameroom, Charming interior

Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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A European Country Getaway ~ 1930s Stone Cottage In Connecticut!, vacation rental in Southwick
A European Country Getaway ~ 1930s Stone Cottage In Connecticut!, vacation rental in Southwick
A European Country Getaway ~ 1930s Stone Cottage In Connecticut!, vacation rental in Southwick

A European Country Getaway ~ 1930s Stone Cottage In Connecticut!

Rental Home
2 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
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The Cliffview Farmhouse in the Heart of Horse Country!, vacation rental in Southwick
The Cliffview Farmhouse in the Heart of Horse Country!, vacation rental in Southwick
The Cliffview Farmhouse in the Heart of Horse Country!, vacation rental in Southwick

The Cliffview Farmhouse in the Heart of Horse Country!

Rental Home
5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Privacy, entertainment, comfort galore 2 BR LR 1BA Home Theater, Pool Table, vacation rental in Southwick
Privacy, entertainment, comfort galore 2 BR LR 1BA Home Theater, Pool Table, vacation rental in Southwick
Privacy, entertainment, comfort galore 2 BR LR 1BA Home Theater, Pool Table, vacation rental in Southwick

Privacy, entertainment, comfort galore 2 BR LR 1BA Home Theater, Pool Table

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Historic home located on scenic Farmington River., vacation rental in Southwick
Historic home located on scenic Farmington River., vacation rental in Southwick
Historic home located on scenic Farmington River., vacation rental in Southwick

Historic home located on scenic Farmington River.

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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The Creation Station is a cozy place so make yourself at home., vacation rental in Southwick
The Creation Station is a cozy place so make yourself at home., vacation rental in Southwick
The Creation Station is a cozy place so make yourself at home., vacation rental in Southwick

The Creation Station is a cozy place so make yourself at home.

Rental Home
1 bedroom
1 bathroom
Sleeps 10
Match: Sleeps
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Beachfront home with direct lake access, private sandy beach, vacation rental in Southwick
Beachfront home with direct lake access, private sandy beach, vacation rental in Southwick
Beachfront home with direct lake access, private sandy beach, vacation rental in Southwick

Beachfront home with direct lake access, private sandy beach

Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Private, spacious In-Law Suite (BR, LR, Bath, Kit), vacation rental in Southwick
Private, spacious In-Law Suite (BR, LR, Bath, Kit), vacation rental in Southwick
Private, spacious In-Law Suite (BR, LR, Bath, Kit), vacation rental in Southwick

Private, spacious In-Law Suite (BR, LR, Bath, Kit)

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Charming cedar shingle cottage, vacation rental in Southwick
Charming cedar shingle cottage, vacation rental in Southwick
Charming cedar shingle cottage, vacation rental in Southwick

Charming cedar shingle cottage

Rental Home
3 bedrooms
1 bathroom
Sleeps 7
Match: Sleeps
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Relax And Enjoy A Fun Getaway At The Bacchus Cottage!, vacation rental in Southwick
Relax And Enjoy A Fun Getaway At The Bacchus Cottage!, vacation rental in Southwick
Relax And Enjoy A Fun Getaway At The Bacchus Cottage!, vacation rental in Southwick

Relax And Enjoy A Fun Getaway At The Bacchus Cottage!

Rental Home
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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!!upscaled Home In A Quiet Neighborhood! You Have the Entire Home to Yourself, vacation rental in Southwick
!!upscaled Home In A Quiet Neighborhood! You Have the Entire Home to Yourself, vacation rental in Southwick
!!upscaled Home In A Quiet Neighborhood! You Have the Entire Home to Yourself, vacation rental in Southwick

!!upscaled Home In A Quiet Neighborhood! You Have the Entire Home to Yourself

Rental Home
4 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Berkshires Retreat & Respite ⭐️ Walk to the water. Peaceful, renovated property., vacation rental in Southwick
Berkshires Retreat & Respite ⭐️ Walk to the water. Peaceful, renovated property., vacation rental in Southwick
Berkshires Retreat & Respite ⭐️ Walk to the water. Peaceful, renovated property., vacation rental in Southwick

Berkshires Retreat & Respite ⭐️ Walk to the water. Peaceful, renovated property.

Rental Home
3 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
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Creekside Country Comfort, Northampton Access! Lovely apartment sleeps 7, vacation rental in Southwick
Creekside Country Comfort, Northampton Access! Lovely apartment sleeps 7, vacation rental in Southwick
Creekside Country Comfort, Northampton Access! Lovely apartment sleeps 7, vacation rental in Southwick

Creekside Country Comfort, Northampton Access! Lovely apartment sleeps 7

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 7
Match: Sleeps
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Convenient Granby Charm, vacation rental in Southwick
Convenient Granby Charm, vacation rental in Southwick
Convenient Granby Charm, vacation rental in Southwick

Convenient Granby Charm

Rental Home
3 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
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5BD Downtown Brownstone - 3 blocks from MGM Casino, vacation rental in Southwick
5BD Downtown Brownstone - 3 blocks from MGM Casino, vacation rental in Southwick
5BD Downtown Brownstone - 3 blocks from MGM Casino, vacation rental in Southwick

5BD Downtown Brownstone - 3 blocks from MGM Casino

Rental Home
5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Charming Cabin Lake Rights, Private Dock 3 bedroom, 2 bath, vacation rental in Southwick
Charming Cabin Lake Rights, Private Dock 3 bedroom, 2 bath, vacation rental in Southwick
Charming Cabin Lake Rights, Private Dock 3 bedroom, 2 bath, vacation rental in Southwick

Charming Cabin Lake Rights, Private Dock 3 bedroom, 2 bath

Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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private andj cozy in east otis, vacation rental in Southwick
private andj cozy in east otis, vacation rental in Southwick
private andj cozy in east otis, vacation rental in Southwick

private andj cozy in east otis

Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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NEW! Manitook Lake Escape w/ Private Dock & Kayaks, vacation rental in Southwick
NEW! Manitook Lake Escape w/ Private Dock & Kayaks, vacation rental in Southwick
NEW! Manitook Lake Escape w/ Private Dock & Kayaks, vacation rental in Southwick

NEW! Manitook Lake Escape w/ Private Dock & Kayaks

Rental Home
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Star gazer no city lights, vacation rental in Southwick
Star gazer no city lights, vacation rental in Southwick
Star gazer no city lights, vacation rental in Southwick

Star gazer no city lights

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 7
Match: Sleeps
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COZY HOME- Located on a quiet Worthy Street with a home in its own compound., vacation rental in Southwick
COZY HOME- Located on a quiet Worthy Street with a home in its own compound., vacation rental in Southwick
COZY HOME- Located on a quiet Worthy Street with a home in its own compound., vacation rental in Southwick

COZY HOME- Located on a quiet Worthy Street with a home in its own compound.

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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One Bedroom Guest House Nestled in the mountain, vacation rental in Southwick
One Bedroom Guest House Nestled in the mountain, vacation rental in Southwick
One Bedroom Guest House Nestled in the mountain, vacation rental in Southwick

One Bedroom Guest House Nestled in the mountain

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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East Otis Reservoir Cabin w/ Porch - Walk to Lake!, vacation rental in Southwick
East Otis Reservoir Cabin w/ Porch - Walk to Lake!, vacation rental in Southwick
East Otis Reservoir Cabin w/ Porch - Walk to Lake!, vacation rental in Southwick

East Otis Reservoir Cabin w/ Porch - Walk to Lake!

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Lily's Lodge, vacation rental in Southwick
Lily's Lodge, vacation rental in Southwick
Lily's Lodge, vacation rental in Southwick

Lily's Lodge

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
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Hilda’s Riverside Retreat, vacation rental in Southwick
Hilda’s Riverside Retreat, vacation rental in Southwick
Hilda’s Riverside Retreat, vacation rental in Southwick

Hilda’s Riverside Retreat

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Lakeside Cottage in the Berkshires, vacation rental in Southwick
Lakeside Cottage in the Berkshires, vacation rental in Southwick
Lakeside Cottage in the Berkshires, vacation rental in Southwick

Lakeside Cottage in the Berkshires

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Enjoy horses and the largest recreational lake in Massachusetts, vacation rental in Southwick
Enjoy horses and the largest recreational lake in Massachusetts, vacation rental in Southwick
Enjoy horses and the largest recreational lake in Massachusetts, vacation rental in Southwick

Enjoy horses and the largest recreational lake in Massachusetts

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Corner Cottage in 16 Acres Springfield, vacation rental in Southwick
Corner Cottage in 16 Acres Springfield, vacation rental in Southwick
Corner Cottage in 16 Acres Springfield, vacation rental in Southwick

Corner Cottage in 16 Acres Springfield

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Mansion & Private 3.5 Acre Estate, vacation rental in Southwick
Mansion & Private 3.5 Acre Estate, vacation rental in Southwick
Mansion & Private 3.5 Acre Estate, vacation rental in Southwick

Mansion & Private 3.5 Acre Estate

Rental Home
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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UPSCALEDHOME IN A QUIET NEIGHBORHOOD. ENTIRE4BED HOME TO YOURSELF Co-Vid 19 Safe, vacation rental in Southwick
UPSCALEDHOME IN A QUIET NEIGHBORHOOD. ENTIRE4BED HOME TO YOURSELF Co-Vid 19 Safe, vacation rental in Southwick
UPSCALEDHOME IN A QUIET NEIGHBORHOOD. ENTIRE4BED HOME TO YOURSELF Co-Vid 19 Safe, vacation rental in Southwick

UPSCALEDHOME IN A QUIET NEIGHBORHOOD. ENTIRE4BED HOME TO YOURSELF Co-Vid 19 Safe

Rental Home
4 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Historic Springfield House w/Patio, 10Min to Dwtn!, vacation rental in Southwick
Historic Springfield House w/Patio, 10Min to Dwtn!, vacation rental in Southwick
Historic Springfield House w/Patio, 10Min to Dwtn!, vacation rental in Southwick

Historic Springfield House w/Patio, 10Min to Dwtn!

Rental Home
2 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
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Front apartment in East Otis, vacation rental in Southwick
Front apartment in East Otis, vacation rental in Southwick
Front apartment in East Otis, vacation rental in Southwick

Front apartment in East Otis

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 5
Match: Sleeps
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Scenic   River  View, vacation rental in Southwick
Scenic   River  View, vacation rental in Southwick
Scenic   River  View, vacation rental in Southwick

Scenic River View

Rental Home
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Fair Vacation rentals, vacation rental in Southwick
Fair Vacation rentals, vacation rental in Southwick
Fair Vacation rentals, vacation rental in Southwick

Fair Vacation rentals

Rental Home
3 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Artist Longmeadow 3bdrmHOUSE worldly retreat, vacation rental in Southwick
Artist Longmeadow 3bdrmHOUSE worldly retreat, vacation rental in Southwick
Artist Longmeadow 3bdrmHOUSE worldly retreat, vacation rental in Southwick

Artist Longmeadow 3bdrmHOUSE worldly retreat

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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An evolving Oasis in the the Upper Hill area, with access to points of interest., vacation rental in Southwick
An evolving Oasis in the the Upper Hill area, with access to points of interest., vacation rental in Southwick
An evolving Oasis in the the Upper Hill area, with access to points of interest., vacation rental in Southwick

An evolving Oasis in the the Upper Hill area, with access to points of interest.

Condo/Apartment
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Newly Renovated 2 Floor Apartment Getaway 6 ROOM 7 BED, vacation rental in Southwick
Newly Renovated 2 Floor Apartment Getaway 6 ROOM 7 BED, vacation rental in Southwick
Newly Renovated 2 Floor Apartment Getaway 6 ROOM 7 BED, vacation rental in Southwick

Newly Renovated 2 Floor Apartment Getaway 6 ROOM 7 BED

Condo/Apartment
6 bedrooms
2 bathrooms
Sleeps 14
Match: Sleeps
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Beautiful Springfield rental- close to MGM And Basket ball hall of fame, vacation rental in Southwick
Beautiful Springfield rental- close to MGM And Basket ball hall of fame, vacation rental in Southwick
Beautiful Springfield rental- close to MGM And Basket ball hall of fame, vacation rental in Southwick

Beautiful Springfield rental- close to MGM And Basket ball hall of fame

Condo/Apartment
5 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Historic Huntington Home - Walk to Westfield River, vacation rental in Southwick
Historic Huntington Home - Walk to Westfield River, vacation rental in Southwick
Historic Huntington Home - Walk to Westfield River, vacation rental in Southwick

Historic Huntington Home - Walk to Westfield River

Rental Home
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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NOT A FULL HOUSE RENTAL ~ SINGLE ROOM AVAILABLE IN BLOOMFIELD, CT , vacation rental in Southwick
NOT A FULL HOUSE RENTAL ~ SINGLE ROOM AVAILABLE IN BLOOMFIELD, CT , vacation rental in Southwick
NOT A FULL HOUSE RENTAL ~ SINGLE ROOM AVAILABLE IN BLOOMFIELD, CT , vacation rental in Southwick

NOT A FULL HOUSE RENTAL ~ SINGLE ROOM AVAILABLE IN BLOOMFIELD, CT

Rental Home
1 bedroom
1 bathroom
Sleeps 1
More info
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