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New Preston Vacation Rentals

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50 rentals in New Preston.
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Lovely Cottage, Completely Remodeled Two Bedroom One Bath Can Accommodate Six., vacation rental in New Preston
Lovely Cottage, Completely Remodeled Two Bedroom One Bath Can Accommodate Six., vacation rental in New Preston
Lovely Cottage, Completely Remodeled Two Bedroom One Bath Can Accommodate Six., vacation rental in New Preston

Lovely Cottage, Completely Remodeled Two Bedroom One Bath Can Accommodate Six.

Rental Home
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Lake Waramaug Cottage, vacation rental in New Preston
Lake Waramaug Cottage, vacation rental in New Preston
Lake Waramaug Cottage, vacation rental in New Preston

Lake Waramaug Cottage

Rental Home
2 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
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Waterfront House on Lake Waramaug!, vacation rental in New Preston
Waterfront House on Lake Waramaug!, vacation rental in New Preston
Waterfront House on Lake Waramaug!, vacation rental in New Preston

Waterfront House on Lake Waramaug!

Rental Home
5 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Lakefront New Preston Cottage w/Dock & Fire Pit!, vacation rental in New Preston
Lakefront New Preston Cottage w/Dock & Fire Pit!, vacation rental in New Preston
Lakefront New Preston Cottage w/Dock & Fire Pit!, vacation rental in New Preston

Lakefront New Preston Cottage w/Dock & Fire Pit!

Rental Home
3 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Modern Barn, NEW Luxurious Home, vacation rental in New Preston
Modern Barn, NEW Luxurious Home, vacation rental in New Preston
Modern Barn, NEW Luxurious Home, vacation rental in New Preston

Modern Barn, NEW Luxurious Home

Rental Home
4 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
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New Listing: Live the good life in this chic designer lake home!, vacation rental in New Preston
New Listing: Live the good life in this chic designer lake home!, vacation rental in New Preston
New Listing: Live the good life in this chic designer lake home!, vacation rental in New Preston

New Listing: Live the good life in this chic designer lake home!

Rental Home
5 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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Country Lake House Nestled Between Vineyards, vacation rental in New Preston
Country Lake House Nestled Between Vineyards, vacation rental in New Preston
Country Lake House Nestled Between Vineyards, vacation rental in New Preston

Country Lake House Nestled Between Vineyards

Rental Home
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Summer Cottage - Bike to Lake Waramaug, vacation rental in New Preston
Summer Cottage - Bike to Lake Waramaug, vacation rental in New Preston
Summer Cottage - Bike to Lake Waramaug, vacation rental in New Preston

Summer Cottage - Bike to Lake Waramaug

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Check Out Cute Summer Cottage on Lake Warmaug, vacation rental in New Preston
Check Out Cute Summer Cottage on Lake Warmaug, vacation rental in New Preston
Check Out Cute Summer Cottage on Lake Warmaug, vacation rental in New Preston

Check Out Cute Summer Cottage on Lake Warmaug

Rental Home
3 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
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Newly Renovated 18th Century Cottage On 4 Acres, vacation rental in New Preston
Newly Renovated 18th Century Cottage On 4 Acres, vacation rental in New Preston
Newly Renovated 18th Century Cottage On 4 Acres, vacation rental in New Preston

Newly Renovated 18th Century Cottage On 4 Acres

Rental Home
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Beautiful contemporary house in Kent, CT, built in 2018., vacation rental in New Preston
Beautiful contemporary house in Kent, CT, built in 2018., vacation rental in New Preston
Beautiful contemporary house in Kent, CT, built in 2018., vacation rental in New Preston

Beautiful contemporary house in Kent, CT, built in 2018.

Rental Home
4 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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Historic Warren/Kent Home, vacation rental in New Preston
Historic Warren/Kent Home, vacation rental in New Preston
Historic Warren/Kent Home, vacation rental in New Preston

Historic Warren/Kent Home

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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In town, walk to everything, close to Kent, South Kent and Marvelwood schools, vacation rental in New Preston
In town, walk to everything, close to Kent, South Kent and Marvelwood schools, vacation rental in New Preston
In town, walk to everything, close to Kent, South Kent and Marvelwood schools, vacation rental in New Preston

In town, walk to everything, close to Kent, South Kent and Marvelwood schools

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Beautiful Cottage and Waterfront Access, vacation rental in New Preston
Beautiful Cottage and Waterfront Access, vacation rental in New Preston
Beautiful Cottage and Waterfront Access, vacation rental in New Preston

Beautiful Cottage and Waterfront Access

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
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Private Annex/Former Artist Studo, vacation rental in New Preston
Private Annex/Former Artist Studo, vacation rental in New Preston
Private Annex/Former Artist Studo, vacation rental in New Preston

Private Annex/Former Artist Studo

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Beautiful Modern Architectural Home in Washington, Ct. 5 Star with video, vacation rental in New Preston
Beautiful Modern Architectural Home in Washington, Ct. 5 Star with video, vacation rental in New Preston
Beautiful Modern Architectural Home in Washington, Ct. 5 Star with video, vacation rental in New Preston

Beautiful Modern Architectural Home in Washington, Ct. 5 Star with video

Rental Home
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
More info
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Warren country retreat, vacation rental in New Preston
Warren country retreat, vacation rental in New Preston
Warren country retreat, vacation rental in New Preston

Warren country retreat

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Expansive Countryside House, 7 Serene Acres with Pond & Woods, vacation rental in New Preston
Expansive Countryside House, 7 Serene Acres with Pond & Woods, vacation rental in New Preston
Expansive Countryside House, 7 Serene Acres with Pond & Woods, vacation rental in New Preston

Expansive Countryside House, 7 Serene Acres with Pond & Woods

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Cottage in Lake Community - Blocked for bathroom renovation (2 bed 2 bath), vacation rental in New Preston
Cottage in Lake Community - Blocked for bathroom renovation (2 bed 2 bath), vacation rental in New Preston
Cottage in Lake Community - Blocked for bathroom renovation (2 bed 2 bath), vacation rental in New Preston

Cottage in Lake Community - Blocked for bathroom renovation (2 bed 2 bath)

Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Stylish antique barn with heated pool. SUMMER 2020 BOOKED. FALL & 2021 AVAIL.

Rental Home
3 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Beautifully Appointed Riverfront Cottage Close to Bantam and Washington, vacation rental in New Preston
Beautifully Appointed Riverfront Cottage Close to Bantam and Washington, vacation rental in New Preston
Beautifully Appointed Riverfront Cottage Close to Bantam and Washington, vacation rental in New Preston

Beautifully Appointed Riverfront Cottage Close to Bantam and Washington

Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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Waterfront Retreat on Bantam Lake with Private Beach - Winter Ski Getaway, vacation rental in New Preston
Waterfront Retreat on Bantam Lake with Private Beach - Winter Ski Getaway, vacation rental in New Preston
Waterfront Retreat on Bantam Lake with Private Beach - Winter Ski Getaway, vacation rental in New Preston

Waterfront Retreat on Bantam Lake with Private Beach - Winter Ski Getaway

Rental Home
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
More info
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Experience Perch Rocks!  A Unique Private Waterfront Cottage on Bantam Lake, vacation rental in New Preston
Experience Perch Rocks!  A Unique Private Waterfront Cottage on Bantam Lake, vacation rental in New Preston
Experience Perch Rocks!  A Unique Private Waterfront Cottage on Bantam Lake, vacation rental in New Preston

Experience Perch Rocks! A Unique Private Waterfront Cottage on Bantam Lake

Rental Home
2 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
More info
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Private Kent Getaway With Views, Pond & Pool, vacation rental in New Preston
Private Kent Getaway With Views, Pond & Pool, vacation rental in New Preston
Private Kent Getaway With Views, Pond & Pool, vacation rental in New Preston

Private Kent Getaway With Views, Pond & Pool

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
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Beautiful, All-Season, Rustic Family Getaway, vacation rental in New Preston
Beautiful, All-Season, Rustic Family Getaway, vacation rental in New Preston
Beautiful, All-Season, Rustic Family Getaway, vacation rental in New Preston

Beautiful, All-Season, Rustic Family Getaway

Rental Home
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
More info
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SUN HILL FARM 1/4 MILE FROM LAKE WARAMAU, vacation rental in New Preston
SUN HILL FARM 1/4 MILE FROM LAKE WARAMAU, vacation rental in New Preston
SUN HILL FARM 1/4 MILE FROM LAKE WARAMAU, vacation rental in New Preston

SUN HILL FARM 1/4 MILE FROM LAKE WARAMAU

Rental Home
5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
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Spectacular Cottage on Bantam Lake, Sleeps 12, vacation rental in New Preston
Spectacular Cottage on Bantam Lake, Sleeps 12, vacation rental in New Preston
Spectacular Cottage on Bantam Lake, Sleeps 12, vacation rental in New Preston

Spectacular Cottage on Bantam Lake, Sleeps 12

Rental Home
7 bedrooms
2 bathrooms
Sleeps 12
Match: Sleeps
More info
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Charming country home in Roxbury, vacation rental in New Preston
Charming country home in Roxbury, vacation rental in New Preston
Charming country home in Roxbury, vacation rental in New Preston

Charming country home in Roxbury

Rental Home
3 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
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100% WASHINGTON! PoshPadsCT 'SHEARER RD' Mint 3BR, Pool, BBQ, 2FPs 90-day min., vacation rental in New Preston
100% WASHINGTON! PoshPadsCT 'SHEARER RD' Mint 3BR, Pool, BBQ, 2FPs 90-day min., vacation rental in New Preston
100% WASHINGTON! PoshPadsCT 'SHEARER RD' Mint 3BR, Pool, BBQ, 2FPs 90-day min., vacation rental in New Preston

100% WASHINGTON! PoshPadsCT 'SHEARER RD' Mint 3BR, Pool, BBQ, 2FPs 90-day min.

Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
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Mabels Hollow Farm, En suite bedroom farm stay,, vacation rental in New Preston
Mabels Hollow Farm, En suite bedroom farm stay,, vacation rental in New Preston
Mabels Hollow Farm, En suite bedroom farm stay,, vacation rental in New Preston

Mabels Hollow Farm, En suite bedroom farm stay,

Rental Home
1 bedroom
2 bathrooms
Sleeps 4
Match: Sleeps
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NEW! Long Meadow Manor, POOL is OPEN for summer!, vacation rental in New Preston
NEW! Long Meadow Manor, POOL is OPEN for summer!, vacation rental in New Preston
NEW! Long Meadow Manor, POOL is OPEN for summer!, vacation rental in New Preston

NEW! Long Meadow Manor, POOL is OPEN for summer!

Rental Home
4 bedrooms
2 bathrooms
Sleeps 12
Match: Sleeps
More info
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Barn Apartment Hideaway, vacation rental in New Preston
Barn Apartment Hideaway, vacation rental in New Preston
Barn Apartment Hideaway, vacation rental in New Preston

Barn Apartment Hideaway

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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100% WASHINGTON PoshPadsCT 'SOUTH ST' Mint 4 BR, Heated Pool, BBQ, Bikes, vacation rental in New Preston
100% WASHINGTON PoshPadsCT 'SOUTH ST' Mint 4 BR, Heated Pool, BBQ, Bikes, vacation rental in New Preston
100% WASHINGTON PoshPadsCT 'SOUTH ST' Mint 4 BR, Heated Pool, BBQ, Bikes, vacation rental in New Preston

100% WASHINGTON PoshPadsCT 'SOUTH ST' Mint 4 BR, Heated Pool, BBQ, Bikes

Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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Gracious Country Home in Washington, Ct, vacation rental in New Preston
Gracious Country Home in Washington, Ct, vacation rental in New Preston
Gracious Country Home in Washington, Ct, vacation rental in New Preston

Gracious Country Home in Washington, Ct

Rental Home
4 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
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5 Acre Sunny, Modern Farmhouse with Outdoor Deck, Patio, and Pool (No weddings), vacation rental in New Preston
5 Acre Sunny, Modern Farmhouse with Outdoor Deck, Patio, and Pool (No weddings), vacation rental in New Preston
5 Acre Sunny, Modern Farmhouse with Outdoor Deck, Patio, and Pool (No weddings), vacation rental in New Preston

5 Acre Sunny, Modern Farmhouse with Outdoor Deck, Patio, and Pool (No weddings)

Rental Home
3 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
More info
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Charming, Riverfront Compound, vacation rental in New Preston
Charming, Riverfront Compound, vacation rental in New Preston
Charming, Riverfront Compound, vacation rental in New Preston

Charming, Riverfront Compound

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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100% WASHINGTON GREEN - Zoom in Map! PoshPadsCT KIRBY ROAD - 3BR Perfect Setting, vacation rental in New Preston
100% WASHINGTON GREEN - Zoom in Map! PoshPadsCT KIRBY ROAD - 3BR Perfect Setting, vacation rental in New Preston
100% WASHINGTON GREEN - Zoom in Map! PoshPadsCT KIRBY ROAD - 3BR Perfect Setting, vacation rental in New Preston

100% WASHINGTON GREEN - Zoom in Map! PoshPadsCT KIRBY ROAD - 3BR Perfect Setting

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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100% ROXBURY PoshPadsCT 'PAINTER RIDGE' Mint 3BR, Pool, BBQ,Bikes 90-day minimum, vacation rental in New Preston
100% ROXBURY PoshPadsCT 'PAINTER RIDGE' Mint 3BR, Pool, BBQ,Bikes 90-day minimum, vacation rental in New Preston
100% ROXBURY PoshPadsCT 'PAINTER RIDGE' Mint 3BR, Pool, BBQ,Bikes 90-day minimum, vacation rental in New Preston

100% ROXBURY PoshPadsCT 'PAINTER RIDGE' Mint 3BR, Pool, BBQ,Bikes 90-day minimum

Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
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100% WASHINGTON! (Zoom in Map++) PoshPadsCT 'SUNNY RIDGE' 8-BR Estate, Pool, BBQ, vacation rental in New Preston
100% WASHINGTON! (Zoom in Map++) PoshPadsCT 'SUNNY RIDGE' 8-BR Estate, Pool, BBQ, vacation rental in New Preston
100% WASHINGTON! (Zoom in Map++) PoshPadsCT 'SUNNY RIDGE' 8-BR Estate, Pool, BBQ, vacation rental in New Preston

100% WASHINGTON! (Zoom in Map++) PoshPadsCT 'SUNNY RIDGE' 8-BR Estate, Pool, BBQ

Rental Home
8 bedrooms
8 bathrooms
Sleeps 16
Match: Sleeps
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100% WASHINGTON! PoshPadsCT'Calhoun' 4BR, Views!,Meadows,Pool,25Acres, 90day min, vacation rental in New Preston
100% WASHINGTON! PoshPadsCT'Calhoun' 4BR, Views!,Meadows,Pool,25Acres, 90day min, vacation rental in New Preston
100% WASHINGTON! PoshPadsCT'Calhoun' 4BR, Views!,Meadows,Pool,25Acres, 90day min, vacation rental in New Preston

100% WASHINGTON! PoshPadsCT'Calhoun' 4BR, Views!,Meadows,Pool,25Acres, 90day min

Rental Home
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
More info
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100% Washington! 'Kielwasser Barn'  PoshPadsCT Pool, 4 FPs, Bikes 90-Day Minimum, vacation rental in New Preston
100% Washington! 'Kielwasser Barn'  PoshPadsCT Pool, 4 FPs, Bikes 90-Day Minimum, vacation rental in New Preston
100% Washington! 'Kielwasser Barn'  PoshPadsCT Pool, 4 FPs, Bikes 90-Day Minimum, vacation rental in New Preston

100% Washington! 'Kielwasser Barn' PoshPadsCT Pool, 4 FPs, Bikes 90-Day Minimum

Rental Home
5 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
More info
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Serene haven in the country, vacation rental in New Preston
Serene haven in the country, vacation rental in New Preston
Serene haven in the country, vacation rental in New Preston

Serene haven in the country

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
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A Haven in the Country--just renovated, vacation rental in New Preston
A Haven in the Country--just renovated, vacation rental in New Preston
A Haven in the Country--just renovated, vacation rental in New Preston

A Haven in the Country--just renovated

Rental Home
3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
More info
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Direct Lakefront, Bantam Lake, Private Deer Island, vacation rental in New Preston
Direct Lakefront, Bantam Lake, Private Deer Island, vacation rental in New Preston
Direct Lakefront, Bantam Lake, Private Deer Island, vacation rental in New Preston

Direct Lakefront, Bantam Lake, Private Deer Island

Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
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Mabels Hollow Farm, In the heart of Litchfield County, vacation rental in New Preston
Mabels Hollow Farm, In the heart of Litchfield County, vacation rental in New Preston
Mabels Hollow Farm, In the heart of Litchfield County, vacation rental in New Preston

Mabels Hollow Farm, In the heart of Litchfield County

Rental Home
5 bedrooms
6 bathrooms
Sleeps 6
Match: Sleeps
More info
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Stay on an Alpaca Farm, vacation rental in New Preston
Stay on an Alpaca Farm, vacation rental in New Preston
Stay on an Alpaca Farm, vacation rental in New Preston

Stay on an Alpaca Farm

Rental Home
2 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
More info
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100% Washington 45 Calhoun PoshPadsCT - Gardens, Pool, BBQ, Bikes 90-day Minimum, vacation rental in New Preston
100% Washington 45 Calhoun PoshPadsCT - Gardens, Pool, BBQ, Bikes 90-day Minimum, vacation rental in New Preston
100% Washington 45 Calhoun PoshPadsCT - Gardens, Pool, BBQ, Bikes 90-day Minimum, vacation rental in New Preston

100% Washington 45 Calhoun PoshPadsCT - Gardens, Pool, BBQ, Bikes 90-day Minimum

Rental Home
5 bedrooms
6 bathrooms
Sleeps 12
Match: Sleeps
More info
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'Tunnel Rd' Mint Reno 4-BR Best Best 100% Roxbury Location PoshPadsCT on Shepaug, vacation rental in New Preston
'Tunnel Rd' Mint Reno 4-BR Best Best 100% Roxbury Location PoshPadsCT on Shepaug, vacation rental in New Preston
'Tunnel Rd' Mint Reno 4-BR Best Best 100% Roxbury Location PoshPadsCT on Shepaug, vacation rental in New Preston

'Tunnel Rd' Mint Reno 4-BR Best Best 100% Roxbury Location PoshPadsCT on Shepaug

Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Mint Warren 1-BR Cottage  - Ski Mohawk, Swim Lake Waramaug - PoshPadsCT, vacation rental in New Preston
Mint Warren 1-BR Cottage  - Ski Mohawk, Swim Lake Waramaug - PoshPadsCT, vacation rental in New Preston
Mint Warren 1-BR Cottage  - Ski Mohawk, Swim Lake Waramaug - PoshPadsCT, vacation rental in New Preston

Mint Warren 1-BR Cottage - Ski Mohawk, Swim Lake Waramaug - PoshPadsCT

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
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Tranquil, Private, Luxury Retreat, vacation rental in New Preston
Tranquil, Private, Luxury Retreat, vacation rental in New Preston
Tranquil, Private, Luxury Retreat, vacation rental in New Preston

Tranquil, Private, Luxury Retreat

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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