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Fairfield Holiday Rentals

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48 rentals in Fairfield.
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Luxe CT Country Home w/ Hi-end WiFi for WFH & School, holiday rental in Fairfield

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

6 bedrooms
8 bathrooms
Sleeps 16
Match: Sleeps
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Charming Cottage By The Sea on Fairfield Beach, holiday rental in Fairfield

Charming Cottage By The Sea on Fairfield Beach

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Elegant Beachfront, beautiful views. Come  enjoy!, holiday rental in Fairfield

Elegant Beachfront, beautiful views. Come enjoy!

5 bedrooms
3 bathrooms
Sleeps 10
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A Fine Waterfront Private Home, In Park-like seaing, holiday rental in Fairfield

A Fine Waterfront Private Home, In Park-like seaing

3 bedrooms
3 bathrooms
Sleeps 10
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Nature Lovers Perfect Location, an hour from Manhattan, holiday rental in Fairfield

Nature Lovers Perfect Location, an hour from Manhattan

4 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Milford Beach House - New Construction!, holiday rental in Fairfield

Milford Beach House - New Construction!

3 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Elegant Country Estate with Equestrian Farm, holiday rental in Fairfield

Elegant Country Estate with Equestrian Farm

6 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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Direct Beach Front Apartment - Discounts available for long term stays., holiday rental in Fairfield

Direct Beach Front Apartment - Discounts available for long term stays.

3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Beach Vacation Get-Away – Near All Conveniences. You Decide Which You Want., holiday rental in Fairfield

Beach Vacation Get-Away – Near All Conveniences. You Decide Which You Want.

4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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FANTASTIC BEACHFRONT HOUSE- BEAUTIFUL VIEW AND BEACH, COME ENJOY !!!!, holiday rental in Fairfield

FANTASTIC BEACHFRONT HOUSE- BEAUTIFUL VIEW AND BEACH, COME ENJOY !!!!

4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Beach side rental booking winter 2020\2021 Available December17 2020, holiday rental in Fairfield

Beach side rental booking winter 2020\2021 Available December17 2020

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Nice Duplex with view of Long Island Sound, holiday rental in Fairfield

Nice Duplex with view of Long Island Sound

4 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Westport: Walk to Town (Really) Private Yard, One Floor, Fall 2020 Reno KHS BMS, holiday rental in Fairfield

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

3 bedrooms
2 bathrooms
Sleeps 8
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Entire Guest House at Fox Pond Farm with Access to In ground Pool, holiday rental in 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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Darien Family Home with Bedroom/Nursery - sleeps 12 & easy 50 min. train to NYC, holiday rental in Fairfield

Darien Family Home with Bedroom/Nursery - sleeps 12 & easy 50 min. train to NYC

4 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Charming Cottage located on Historic Estate 1 Hour from NYC!, holiday rental in Fairfield

Charming Cottage located on Historic Estate 1 Hour from NYC!

3 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Enjoy the serenity of the countryside at Pleasant Valley Trails - Home & Acres, holiday rental in Fairfield

Enjoy the serenity of the countryside at Pleasant Valley Trails - Home & Acres

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Secluded cottage on cul de sac in Rowayton., holiday rental in Fairfield

Secluded cottage on cul de sac in Rowayton.

2 bedrooms
1 bathroom
Sleeps 4
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Beautiful Home for Your Family Vacation, holiday rental in Fairfield

Beautiful Home for Your Family Vacation

7 bedrooms
6 bathrooms
Sleeps 12
Match: Sleeps
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Cozy Cottage in Westport, CT (charming & pristine in fabulous location), holiday rental in Fairfield

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

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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1/2 block to Compo Beach on Long Island Sound!, holiday rental in Fairfield

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

4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Premiere beach property, holiday rental in Fairfield

Premiere beach property

1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Modern Waterfront Home  * WESTPORT RESIDENTS/PROSPECTIVE RESIDENTS ONLY, holiday rental in Fairfield

Modern Waterfront Home * WESTPORT RESIDENTS/PROSPECTIVE RESIDENTS ONLY

3 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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#2 - Your own place on the Beach near Silver Sands Park, holiday rental in Fairfield

#2 - Your own place on the Beach near Silver Sands Park

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Mill Pond Retreat, holiday rental in Fairfield

Mill Pond Retreat

4 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Spectacular Modern Home Near NYC, holiday rental in Fairfield

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 Fairfield

Westport 'Gold Coast' across from Southport beach

1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Romantic Riverfront Farm House at Historic Aspetuck Corners, holiday rental in Fairfield

Romantic Riverfront Farm House at Historic Aspetuck Corners

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Luxury Executive Estate 1 Hr from New York City, holiday rental in Fairfield

Luxury Executive Estate 1 Hr from New York City

6 bedrooms
5 bathrooms
Sleeps 20
Match: Sleeps
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Apartment in great location, suburban, holiday rental in Fairfield

Apartment in great location, suburban

1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
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#1 - A beach place by Silver Sands Park, holiday rental in Fairfield

#1 - A beach place by Silver Sands Park

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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New modern house near the water (WESTPORT RESIDENTS ONLY), holiday rental in Fairfield

New modern house near the water (WESTPORT RESIDENTS ONLY)

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Beachfront Cottage w/Porch on Long Island Sound, holiday rental in Fairfield

Beachfront Cottage w/Porch on Long Island Sound

3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Beach Cottage next to Silver Sands State Park, holiday rental in Fairfield

Beach Cottage next to Silver Sands State Park

2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Rowayton House Close To Town, holiday rental in Fairfield

Rowayton House Close To Town

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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A New England Jewel with Scenic Beauty, holiday rental in Fairfield

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 Fairfield

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 Fairfield

Updated Farmhouse Retreat

5 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
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Suburban Getaway. Heated Pool. NO PARTIES., holiday rental in Fairfield

Suburban Getaway. Heated Pool. NO PARTIES.

5 bedrooms
3 bathrooms
Sleeps 11
Match: Sleeps
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Award Winning Private Pool House on Spectacular Historic and Rare 24-Acre Estate, holiday rental in 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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Large Studio by the Beach w/private entrance, holiday rental in Fairfield

Large Studio by the Beach w/private entrance

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Newly listed Property, Home Away from Home, Close to restaurants and local beach, holiday rental in Fairfield

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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Live/work loft with view and exposed brick, holiday rental in Fairfield

Live/work loft with view and exposed brick

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Private Estate Large Private Pool, holiday rental in Fairfield

Private Estate Large Private Pool

4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Lovely River view property, holiday rental in Fairfield

Lovely River view property

2 bedrooms
1 bathroom
Sleeps 7
Match: Sleeps
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NEW! Luxury Forest Escape w/ Creek On-Site + Deck!, holiday rental in Fairfield

NEW! Luxury Forest Escape w/ Creek On-Site + Deck!

5 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
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Comtemporary 1Bdr w/ Queen Bed + Free Wifi, holiday rental in Fairfield

Comtemporary 1Bdr w/ Queen Bed + Free Wifi

1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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New Stylish Beach Home near Stamford Downtown/Cove Beach/ 40 min to NYC �, holiday rental in Fairfield

New Stylish Beach Home near Stamford Downtown/Cove Beach/ 40 min to NYC �

5 bedrooms
2 bathrooms
Sleeps 12
Match: Sleeps
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CLEAN, COMFORTABLE APT.  NEAR YALE, NEW HAVEN, AND AREA COMPANIES, holiday rental in Fairfield

CLEAN, COMFORTABLE APT. NEAR YALE, NEW HAVEN, AND AREA COMPANIES

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

The West Lane Inn - Queen Room

1 bedroom
1 bathroom
Sleeps 1
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