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New Fairfield Holiday Rentals

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49 rentals in New Fairfield.
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Lakefront Luxury Retreat on Candlewood Lake, holiday rental in New Fairfield

Lakefront Luxury Retreat on Candlewood Lake

5 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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The Lookout on Candlewood Lake, holiday rental in New Fairfield

The Lookout on Candlewood Lake

3 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Amazing Adirondack Candlewood Lake Front Compound, holiday rental in New Fairfield

Amazing Adirondack Candlewood Lake Front Compound

5 bedrooms
6 bathrooms
Sleeps 8
Match: Sleeps
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3 BR Cabin in Private Candlewood Lake Community, holiday rental in New Fairfield

3 BR Cabin in Private Candlewood Lake Community

3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Newly Listed Lake House! Private Beach on Candlewood Lake, New Construction Beau, holiday rental in New Fairfield

Newly Listed Lake House! Private Beach on Candlewood Lake, New Construction Beau

2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Night Light Lake House, holiday rental in New Fairfield

Night Light Lake House

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Welcome to The Lake: Your Private Paradise Awaits!, holiday rental in New Fairfield

Welcome to The Lake: Your Private Paradise Awaits!

4 bedrooms
3 bathrooms
Sleeps 11
Match: Sleeps
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Charming 4BR 2BA Direct Waterfront Home w/Panoramic Views on Candlewood Lake, holiday rental in New Fairfield

Charming 4BR 2BA Direct Waterfront Home w/Panoramic Views on Candlewood Lake

4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Lakefront Escape with Gorgeous Views a Short Trip from New York City!, holiday rental in New Fairfield

Lakefront Escape with Gorgeous Views a Short Trip from New York City!

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Elegant Country Estate with Equestrian Farm, holiday rental in New Fairfield

Elegant Country Estate with Equestrian Farm

6 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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Peaceful Candlewood  lake/woods retreat., holiday rental in New Fairfield

Peaceful Candlewood lake/woods retreat.

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Exceptional Beauty On The Water!! Candlewood Lake - Danbury, CT, holiday rental in New Fairfield

Exceptional Beauty On The Water!! Candlewood Lake - Danbury, CT

5 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
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House on Appalachian Trail, walking distance from NYC trains. 3bd/1ba, 3 acres, holiday rental in New Fairfield

House on Appalachian Trail, walking distance from NYC trains. 3bd/1ba, 3 acres

3 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
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Lake Home with Hot Tub, Pool Table, Ping Pong Table, Fishing, Boats, Fire Pit, holiday rental in New Fairfield

Lake Home with Hot Tub, Pool Table, Ping Pong Table, Fishing, Boats, Fire Pit

3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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Lakeside Modern Farmhouse/Craftsman Chalet, holiday rental in New Fairfield

Lakeside Modern Farmhouse/Craftsman Chalet

4 bedrooms
4 bathrooms
Sleeps 8
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Direct Water Front Home, holiday rental in New Fairfield

Direct Water Front Home

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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1905 Remodeled New England Cape Quintessential Connecticut Countryside Getaway, holiday rental in New Fairfield

1905 Remodeled New England Cape Quintessential Connecticut Countryside Getaway

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Modern cottage on the Housatonic River, holiday rental in New Fairfield

Modern cottage on the Housatonic River

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Gorgeous Lake Adjacent Home - Pet Friendly and Fenced!, holiday rental in New Fairfield

Gorgeous Lake Adjacent Home - Pet Friendly and Fenced!

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Lakefront home with private dock, kayaks,  and paddleboard.  Boat rentals nearby, holiday rental in New Fairfield

Lakefront home with private dock, kayaks, and paddleboard. Boat rentals nearby

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Level, direct lakefront, expansive western views, beach on Candlewood Lake, holiday rental in New Fairfield

Level, direct lakefront, expansive western views, beach on Candlewood Lake

5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Serene, Peaceful Get-Away (Log Cabin by the Lake), holiday rental in New Fairfield

Serene, Peaceful Get-Away (Log Cabin by the Lake)

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Direct Waterfront on Candlewood Lake with/ boat slip & expansive outdoor kitchen, holiday rental in New Fairfield

Direct Waterfront on Candlewood Lake with/ boat slip & expansive outdoor kitchen

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Luxurious Retreat in the Country only 1 hour from NYC, holiday rental in New Fairfield

Luxurious Retreat in the Country only 1 hour from NYC

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Secluded country cabin upstate New York, near  metro north train, holiday rental in New Fairfield

Secluded country cabin upstate New York, near metro north train

1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
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Stunning Waterfront Lake House with Amazing Views, holiday rental in New Fairfield

Stunning Waterfront Lake House with Amazing Views

3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Direct Lakefront Home on Lake Lillinonah with Elevator Access, holiday rental in New Fairfield

Direct Lakefront Home on Lake Lillinonah with Elevator Access

3 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Entire Guest House at Fox Pond Farm with Access to In ground Pool, holiday rental in New Fairfield

Entire Guest House at Fox Pond Farm with Access to In ground Pool

4 bedrooms
3 bathrooms
Sleeps 11
Match: Sleeps
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The Hilltop - Stunning, holiday rental in New Fairfield

The Hilltop - Stunning

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Rustic Country Beach Cottage Candlewood Lake, holiday rental in New Fairfield

Rustic Country Beach Cottage Candlewood Lake

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Stately 1792 retreat on 23 acres, chic modern renovation with gunite pool, holiday rental in New Fairfield

Stately 1792 retreat on 23 acres, chic modern renovation with gunite pool

3 bedrooms
3 bathrooms
Sleeps 5
Match: Sleeps
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Charming country home in Roxbury, holiday rental in New Fairfield

Charming country home in Roxbury

3 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
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Mabels Hollow Farm, En suite bedroom farm stay,, holiday rental in New Fairfield

Mabels Hollow Farm, En suite bedroom farm stay,

1 bedroom
2 bathrooms
Sleeps 4
Match: Sleeps
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Stunning Lakefront Home w/ Private Dock for Swimming (and Kayaks For Use)., holiday rental in New Fairfield

Stunning Lakefront Home w/ Private Dock for Swimming (and Kayaks For Use).

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Lake House Rental On Your Own Private Lake, holiday rental in New Fairfield

Lake House Rental On Your Own Private Lake

4 bedrooms
3 bathrooms
Sleeps 11
Match: Sleeps
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2 Bedroom Suite with Kitchen, holiday rental in New Fairfield

2 Bedroom Suite with Kitchen

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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100% WASHINGTON PoshPadsCT 'SOUTH ST' Mint 4 BR, Heated Pool, BBQ, Bikes, holiday rental in New Fairfield

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

4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Tentrr - Cooke's Creek, holiday rental in New Fairfield

Tentrr - Cooke's Creek

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Tentrr Signature Site - Holmestead Woods, holiday rental in New Fairfield

Tentrr Signature Site - Holmestead Woods

1 bedroom
1 bathroom
Sleeps 8
Match: Sleeps
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Studio Cottage on working Horse Farm/ SwimSpa, holiday rental in New Fairfield

Studio Cottage on working Horse Farm/ SwimSpa

0 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
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Lake Summer Home with a Dog (Monthly rental only), holiday rental in New Fairfield

Lake Summer Home with a Dog (Monthly rental only)

4 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
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One of a Kind Cotswold Summer Retreat on 18 Secluded Acres, holiday rental in New Fairfield

One of a Kind Cotswold Summer Retreat on 18 Secluded Acres

4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Nature & Luxury *Lavender Lake Est (Kosher optional), holiday rental in New Fairfield

Nature & Luxury *Lavender Lake Est (Kosher optional)

7 bedrooms
6 bathrooms
Sleeps 18
Match: Sleeps
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Country Condo ( 3 Months mimimun ), holiday rental in New Fairfield

Country Condo ( 3 Months mimimun )

2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Serene haven in the country, holiday rental in New Fairfield

Serene haven in the country

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Award Winning Private Pool House on Spectacular Historic and Rare 24-Acre Estate, holiday rental in New Fairfield

Award Winning Private Pool House on Spectacular Historic and Rare 24-Acre Estate

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Sunset Manor, holiday rental in New Fairfield

Sunset Manor

6 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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Private Estate Large Private Pool, holiday rental in New Fairfield

Private Estate Large Private Pool

4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Tentrr Signature Site - Maybrook Farm - The Ridge, holiday rental in New Fairfield

Tentrr Signature Site - Maybrook Farm - The Ridge

1 bedroom
1 bathroom
Sleeps 5
Match: Sleeps
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The West Lane Inn - Queen Room, holiday rental in New Fairfield

The West Lane Inn - Queen Room

1 bedroom
1 bathroom
Sleeps 1
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