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Holiday Homes in Ridgefield

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49 rentals in Ridgefield.
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The West Lane Inn - Queen Room, holiday rental in Ridgefield

The West Lane Inn - Queen Room

1 bedroom
1 bathroom
Sleeps 1
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Elegant Country Estate with Equestrian Farm, holiday rental in Ridgefield

Elegant Country Estate with Equestrian Farm

6 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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Exceptional Beauty On The Water!! Candlewood Lake - Danbury, CT, holiday rental in Ridgefield

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

5 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
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Lakeside Modern Farmhouse/Craftsman Chalet, holiday rental in Ridgefield

Lakeside Modern Farmhouse/Craftsman Chalet

4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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1905 Remodeled New England Cape Quintessential Connecticut Countryside Getaway, holiday rental in Ridgefield

1905 Remodeled New England Cape Quintessential Connecticut Countryside Getaway

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Gorgeous Lake Adjacent Home - Pet Friendly and Fenced!, holiday rental in Ridgefield

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 Ridgefield

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

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Private 3.5 acre estate  Zen House /Historic mid century modern  / lap pool, holiday rental in Ridgefield

Private 3.5 acre estate Zen House /Historic mid century modern / lap pool

1 bedroom
2 bathrooms
Sleeps 2
Match: Sleeps
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The Lookout on Candlewood Lake, holiday rental in Ridgefield

The Lookout on Candlewood Lake

3 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Level, direct lakefront, expansive western views, beach on Candlewood Lake, holiday rental in Ridgefield

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

5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Luxe CT Country Home w/ Hi-end WiFi for WFH & School, holiday rental in Ridgefield

Luxe CT Country Home w/ Hi-end WiFi for WFH & School

6 bedrooms
8 bathrooms
Sleeps 16
Match: Sleeps
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Luxurious Retreat in the Country only 1 hour from NYC, holiday rental in Ridgefield

Luxurious Retreat in the Country only 1 hour from NYC

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Westport: Walk to Town (Really) Private Yard, One Floor, Fall 2020 Reno KHS BMS, holiday rental in Ridgefield

Westport: Walk to Town (Really) Private Yard, One Floor, Fall 2020 Reno KHS BMS

3 bedrooms
2 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 Ridgefield

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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Stunning Waterfront Lake House with Amazing Views, holiday rental in Ridgefield

Stunning Waterfront Lake House with Amazing Views

3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Charming Cottage located on Historic Estate 1 Hour from NYC!, holiday rental in Ridgefield

Charming Cottage located on Historic Estate 1 Hour from NYC!

3 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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3 BR Cabin in Private Candlewood Lake Community, holiday rental in Ridgefield

3 BR Cabin in Private Candlewood Lake Community

3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Beautiful Home for Your Family Vacation, holiday rental in Ridgefield

Beautiful Home for Your Family Vacation

7 bedrooms
6 bathrooms
Sleeps 12
Match: Sleeps
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Back Country Estate with Pool - Greenwich CT, holiday rental in Ridgefield

Back Country Estate with Pool - Greenwich CT

5 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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5-Br 3-bath Skylit Home on 3 Forested Acres, holiday rental in Ridgefield

5-Br 3-bath Skylit Home on 3 Forested Acres

5 bedrooms
3 bathrooms
Sleeps 11
Match: Sleeps
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Cozy Cottage in Westport, CT (charming & pristine in fabulous location), holiday rental in Ridgefield

Cozy Cottage in Westport, CT (charming & pristine in fabulous location)

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Serene Connecticut Retreat - Luxury 2 bedroom apt, holiday rental in Ridgefield

Serene Connecticut Retreat - Luxury 2 bedroom apt

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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North Stamford Guest House, holiday rental in Ridgefield

North Stamford Guest House

2 bedrooms
2 bathrooms
Sleeps 3
Match: Sleeps
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1/2 block to Compo Beach on Long Island Sound!, holiday rental in Ridgefield

1/2 block to Compo Beach on Long Island Sound!

4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Less than 1 block to the beach in Westport! Long Term Rentals too., holiday rental in Ridgefield

Less than 1 block to the beach in Westport! Long Term Rentals too.

4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Modern Waterfront Home  * WESTPORT RESIDENTS/PROSPECTIVE RESIDENTS ONLY, holiday rental in Ridgefield

Modern Waterfront Home * WESTPORT RESIDENTS/PROSPECTIVE RESIDENTS ONLY

3 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Spectacular Modern Home Near NYC, holiday rental in Ridgefield

Spectacular Modern Home Near NYC

5 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Westport 'Gold Coast' across from Southport beach, holiday rental in Ridgefield

Westport 'Gold Coast' across from Southport beach

1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Luxury Executive Estate 1 Hr from New York City, holiday rental in Ridgefield

Luxury Executive Estate 1 Hr from New York City

6 bedrooms
5 bathrooms
Sleeps 20
Match: Sleeps
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New modern house near the water (WESTPORT RESIDENTS ONLY), holiday rental in Ridgefield

New modern house near the water (WESTPORT RESIDENTS ONLY)

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Tentrr Signature Site - Holmestead Woods, holiday rental in Ridgefield

Tentrr Signature Site - Holmestead Woods

1 bedroom
1 bathroom
Sleeps 8
Match: Sleeps
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A New England Jewel with Scenic Beauty, holiday rental in Ridgefield

A New England Jewel with Scenic Beauty

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Interior Designer's Enchanting And Bucolic Home, holiday rental in Ridgefield

Interior Designer's Enchanting And Bucolic Home

4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Updated Farmhouse Retreat, holiday rental in Ridgefield

Updated Farmhouse Retreat

5 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
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Studio Cottage on working Horse Farm/ SwimSpa, holiday rental in Ridgefield

Studio Cottage on working Horse Farm/ SwimSpa

0 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
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One of a Kind Cotswold Summer Retreat on 18 Secluded Acres, holiday rental in Ridgefield

One of a Kind Cotswold Summer Retreat on 18 Secluded Acres

4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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A Beautiful Nature Retreat, holiday rental in Ridgefield

A Beautiful Nature Retreat

1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Country Condo ( 3 Months mimimun ), holiday rental in Ridgefield

Country Condo ( 3 Months mimimun )

2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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NEW! Private Getaway <2 Mi to Croton Falls Station, holiday rental in Ridgefield

NEW! Private Getaway <2 Mi to Croton Falls Station

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Suburban Getaway. Heated Pool. NO PARTIES., holiday rental in Ridgefield

Suburban Getaway. Heated Pool. NO PARTIES.

5 bedrooms
3 bathrooms
Sleeps 11
Match: Sleeps
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Sophisticated Country Living, holiday rental in Ridgefield

Sophisticated Country Living

4 bedrooms
4 bathrooms
Sleeps 5
Match: Sleeps
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Nature Lovers Perfect Location, an hour from Manhattan, holiday rental in Ridgefield

Nature Lovers Perfect Location, an hour from Manhattan

4 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Mill Pond Retreat, holiday rental in Ridgefield

Mill Pond Retreat

4 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
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A Fine Waterfront Private Home, In Park-like seaing, holiday rental in Ridgefield

A Fine Waterfront Private Home, In Park-like seaing

3 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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See Beautiful Fall Foliage - Lovely CT country home sleeps 10 + heated  pool!, holiday rental in Ridgefield

See Beautiful Fall Foliage - Lovely CT country home sleeps 10 + heated pool!

3 bedrooms
5 bathrooms
Sleeps 9
Match: Sleeps
More info
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Emerald's Farm, holiday rental in Ridgefield

Emerald's Farm

5 bedrooms
4 bathrooms
Sleeps 16
Match: Sleeps
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Award Winning Private Pool House on Spectacular Historic and Rare 24-Acre Estate, holiday rental in Ridgefield

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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Newly listed Property, Home Away from Home, Close to restaurants and local beach, holiday rental in Ridgefield

Newly listed Property, Home Away from Home, Close to restaurants and local beach

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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US Senior Women's Open - Private Estate Large Private Pool, holiday rental in Ridgefield

US Senior Women's Open - Private Estate Large Private Pool

4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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NEWLY LISTED! Walk to Private Beach on Candlewood Lake, New Construction with Be, holiday rental in Ridgefield

NEWLY LISTED! Walk to Private Beach on Candlewood Lake, New Construction with Be

2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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