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Fairfield Vacation Rentals

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48 rentals in Fairfield.
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Westport 'Gold Coast' across from Southport beach, vacation rental in Fairfield
Westport 'Gold Coast' across from Southport beach, vacation rental in Fairfield
Westport 'Gold Coast' across from Southport beach, vacation rental in Fairfield

Westport 'Gold Coast' across from Southport beach

Rental Home
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Luxe CT Country Home w/ Hi-end WiFi for WFH & School, vacation rental in Fairfield
Luxe CT Country Home w/ Hi-end WiFi for WFH & School, vacation rental in Fairfield
Luxe CT Country Home w/ Hi-end WiFi for WFH & School, vacation rental in Fairfield

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

Rental Home
6 bedrooms
8 bathrooms
Sleeps 16
Match: Sleeps
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Gem by the Sound Summ, vacation rental in Fairfield
Gem by the Sound Summ, vacation rental in Fairfield
Gem by the Sound Summ, vacation rental in Fairfield

Gem by the Sound Summ

Rental Home
0 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Charming Cottage By The Sea on Fairfield Beach, vacation rental in Fairfield
Charming Cottage By The Sea on Fairfield Beach, vacation rental in Fairfield
Charming Cottage By The Sea on Fairfield Beach, vacation rental in Fairfield

Charming Cottage By The Sea on Fairfield Beach

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Fairfield Old Post Road with pool - walk to  NYC train and Beach, vacation rental in Fairfield
Fairfield Old Post Road with pool - walk to  NYC train and Beach, vacation rental in Fairfield
Fairfield Old Post Road with pool - walk to  NYC train and Beach, vacation rental in Fairfield

Fairfield Old Post Road with pool - walk to NYC train and Beach

Rental Home
5 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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Elegant Beachfront, beautiful views. Come  enjoy!, vacation rental in Fairfield
Elegant Beachfront, beautiful views. Come  enjoy!, vacation rental in Fairfield
Elegant Beachfront, beautiful views. Come  enjoy!, vacation rental in Fairfield

Elegant Beachfront, beautiful views. Come enjoy!

Rental Home
5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Cozy getaway in Fairfield - EXPERTLY SANITIZED, vacation rental in Fairfield
Cozy getaway in Fairfield - EXPERTLY SANITIZED, vacation rental in Fairfield
Cozy getaway in Fairfield - EXPERTLY SANITIZED, vacation rental in Fairfield

Cozy getaway in Fairfield - EXPERTLY SANITIZED

Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Stunning direct waterfront beach house!, vacation rental in Fairfield
Stunning direct waterfront beach house!, vacation rental in Fairfield
Stunning direct waterfront beach house!, vacation rental in Fairfield

Stunning direct waterfront beach house!

Rental Home
3 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
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Lakefront getaway walkable to restaurants and shops, vacation rental in Fairfield
Lakefront getaway walkable to restaurants and shops, vacation rental in Fairfield
Lakefront getaway walkable to restaurants and shops, vacation rental in Fairfield

Lakefront getaway walkable to restaurants and shops

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Summer Rental:  4 Car Garage 1/4 mile to town of Fairfeild Center, vacation rental in Fairfield
Summer Rental:  4 Car Garage 1/4 mile to town of Fairfeild Center, vacation rental in Fairfield
Summer Rental:  4 Car Garage 1/4 mile to town of Fairfeild Center, vacation rental in Fairfield

Summer Rental: 4 Car Garage 1/4 mile to town of Fairfeild Center

Rental Home
4 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
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Nature Lovers Perfect Location, an hour from Manhattan, vacation rental in Fairfield
Nature Lovers Perfect Location, an hour from Manhattan, vacation rental in Fairfield
Nature Lovers Perfect Location, an hour from Manhattan, vacation rental in Fairfield

Nature Lovers Perfect Location, an hour from Manhattan

Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Private house ,direct creek front, walk to Pine Creek beach, Boat dock and decks, vacation rental in Fairfield
Private house ,direct creek front, walk to Pine Creek beach, Boat dock and decks, vacation rental in Fairfield
Private house ,direct creek front, walk to Pine Creek beach, Boat dock and decks, vacation rental in Fairfield

Private house ,direct creek front, walk to Pine Creek beach, Boat dock and decks

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Beautiful Connecticut Abode, close to park & beach, vacation rental in Fairfield
Beautiful Connecticut Abode, close to park & beach, vacation rental in Fairfield
Beautiful Connecticut Abode, close to park & beach, vacation rental in Fairfield

Beautiful Connecticut Abode, close to park & beach

Rental Home
0 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Peaceful Pinewood Retreat 1 hour from NYC, close to Yale, SHU, & FU!, vacation rental in Fairfield
Peaceful Pinewood Retreat 1 hour from NYC, close to Yale, SHU, & FU!, vacation rental in Fairfield
Peaceful Pinewood Retreat 1 hour from NYC, close to Yale, SHU, & FU!, vacation rental in Fairfield

Peaceful Pinewood Retreat 1 hour from NYC, close to Yale, SHU, & FU!

Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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FANTASTIC BEACHFRONT HOUSE- BEAUTIFUL VIEW AND BEACH, COME ENJOY !!!!, vacation rental in Fairfield
FANTASTIC BEACHFRONT HOUSE- BEAUTIFUL VIEW AND BEACH, COME ENJOY !!!!, vacation rental in Fairfield
FANTASTIC BEACHFRONT HOUSE- BEAUTIFUL VIEW AND BEACH, COME ENJOY !!!!, vacation rental in Fairfield

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

Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Ideal Westport location - Compo Beach, Longshore Club Park, fine dining, vacation rental in Fairfield
Ideal Westport location - Compo Beach, Longshore Club Park, fine dining, vacation rental in Fairfield
Ideal Westport location - Compo Beach, Longshore Club Park, fine dining, vacation rental in Fairfield

Ideal Westport location - Compo Beach, Longshore Club Park, fine dining

Rental Home
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, vacation rental in Fairfield
Westport: Walk to Town (Really) Private Yard, One Floor, Fall 2020 Reno KHS BMS, vacation rental in Fairfield
Westport: Walk to Town (Really) Private Yard, One Floor, Fall 2020 Reno KHS BMS, vacation rental in Fairfield

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

Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Romantic Riverfront Farm House at Historic Aspetuck Corners, vacation rental in Fairfield
Romantic Riverfront Farm House at Historic Aspetuck Corners, vacation rental in Fairfield
Romantic Riverfront Farm House at Historic Aspetuck Corners, vacation rental in Fairfield

Romantic Riverfront Farm House at Historic Aspetuck Corners

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Charming house water views 2 houses from the clean deep sandy Private beach., vacation rental in Fairfield
Charming house water views 2 houses from the clean deep sandy Private beach., vacation rental in Fairfield
Charming house water views 2 houses from the clean deep sandy Private beach., vacation rental in Fairfield

Charming house water views 2 houses from the clean deep sandy Private beach.

Rental Home
5 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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Cozy Cottage in Westport, CT (charming & pristine in fabulous location), vacation rental in Fairfield
Cozy Cottage in Westport, CT (charming & pristine in fabulous location), vacation rental in Fairfield
Cozy Cottage in Westport, CT (charming & pristine in fabulous location), vacation rental in Fairfield

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

Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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A private summer compound in Westport, CT - total seclusion yet close to it all, vacation rental in Fairfield
A private summer compound in Westport, CT - total seclusion yet close to it all, vacation rental in Fairfield
A private summer compound in Westport, CT - total seclusion yet close to it all, vacation rental in Fairfield

A private summer compound in Westport, CT - total seclusion yet close to it all

Rental Home
6 bedrooms
8 bathrooms
Sleeps 12
Match: Sleeps
More info
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Mill Pond Retreat, vacation rental in Fairfield
Mill Pond Retreat, vacation rental in Fairfield
Mill Pond Retreat, vacation rental in Fairfield

Mill Pond Retreat

Rental Home
4 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Westport 'Gold Coast' across from Southport beach, vacation rental in Fairfield
Westport 'Gold Coast' across from Southport beach, vacation rental in Fairfield
Westport 'Gold Coast' across from Southport beach, vacation rental in Fairfield

Westport 'Gold Coast' across from Southport beach

Rental Home
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
More info
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A New England Jewel with Scenic Beauty, vacation rental in Fairfield
A New England Jewel with Scenic Beauty, vacation rental in Fairfield
A New England Jewel with Scenic Beauty, vacation rental in Fairfield

A New England Jewel with Scenic Beauty

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
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Summer rental House Westport, vacation rental in Fairfield
Summer rental House Westport, vacation rental in Fairfield
Summer rental House Westport, vacation rental in Fairfield

Summer rental House Westport

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Real log house on Directly on the River with heated pool one hour from NYC., vacation rental in Fairfield
Real log house on Directly on the River with heated pool one hour from NYC., vacation rental in Fairfield
Real log house on Directly on the River with heated pool one hour from NYC., vacation rental in Fairfield

Real log house on Directly on the River with heated pool one hour from NYC.

Rental Home
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Historic Apartment in Downtown Westport, vacation rental in Fairfield
Historic Apartment in Downtown Westport, vacation rental in Fairfield
Historic Apartment in Downtown Westport, vacation rental in Fairfield

Historic Apartment in Downtown Westport

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Interior Designer's Enchanting And Bucolic Home, vacation rental in Fairfield
Interior Designer's Enchanting And Bucolic Home, vacation rental in Fairfield
Interior Designer's Enchanting And Bucolic Home, vacation rental in Fairfield

Interior Designer's Enchanting And Bucolic Home

Rental Home
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Summer in Westport, CT! - Renovated, Private, Close to everything!, vacation rental in Fairfield
Summer in Westport, CT! - Renovated, Private, Close to everything!, vacation rental in Fairfield
Summer in Westport, CT! - Renovated, Private, Close to everything!, vacation rental in Fairfield

Summer in Westport, CT! - Renovated, Private, Close to everything!

Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
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Historic oyster shack., vacation rental in Fairfield
Historic oyster shack., vacation rental in Fairfield
Historic oyster shack., vacation rental in Fairfield

Historic oyster shack.

Rental Home
1 bedroom
1 bathroom
Sleeps 10
Match: Sleeps
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Beach Cottage on the Harbor; discounted weekly rental in summer, vacation rental in Fairfield
Beach Cottage on the Harbor; discounted weekly rental in summer, vacation rental in Fairfield
Beach Cottage on the Harbor; discounted weekly rental in summer, vacation rental in Fairfield

Beach Cottage on the Harbor; discounted weekly rental in summer

Rental Home
4 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Walk to the beach from this modern home, vacation rental in Fairfield
Walk to the beach from this modern home, vacation rental in Fairfield
Walk to the beach from this modern home, vacation rental in Fairfield

Walk to the beach from this modern home

Rental Home
3 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Available ONLY 6/23-7/4 for entire term, vacation rental in Fairfield
Available ONLY 6/23-7/4 for entire term, vacation rental in Fairfield
Available ONLY 6/23-7/4 for entire term, vacation rental in Fairfield

Available ONLY 6/23-7/4 for entire term

Rental Home
6 bedrooms
6 bathrooms
Sleeps 8
Match: Sleeps
More info
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Brand New Laurel Beach House!, vacation rental in Fairfield
Brand New Laurel Beach House!, vacation rental in Fairfield
Brand New Laurel Beach House!, vacation rental in Fairfield

Brand New Laurel Beach House!

Rental Home
4 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Beach house 3 BR/3&1/half bath home with private beach in CT., vacation rental in Fairfield
Beach house 3 BR/3&1/half bath home with private beach in CT., vacation rental in Fairfield
Beach house 3 BR/3&1/half bath home with private beach in CT., vacation rental in Fairfield

Beach house 3 BR/3&1/half bath home with private beach in CT.

Rental Home
3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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Westport Family Home 3 miles To Beach, vacation rental in Fairfield
Westport Family Home 3 miles To Beach, vacation rental in Fairfield
Westport Family Home 3 miles To Beach, vacation rental in Fairfield

Westport Family Home 3 miles To Beach

Rental Home
5 bedrooms
6 bathrooms
Sleeps 8
Match: Sleeps
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Vacation Ready: Beautiful House with Heated Pool, vacation rental in Fairfield
Vacation Ready: Beautiful House with Heated Pool, vacation rental in Fairfield
Vacation Ready: Beautiful House with Heated Pool, vacation rental in Fairfield

Vacation Ready: Beautiful House with Heated Pool

Rental Home
6 bedrooms
7 bathrooms
Sleeps 11
Match: Sleeps
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Walk-To-Town Gem! Charming renovated Colonial in sought after neighborhood., vacation rental in Fairfield
Walk-To-Town Gem! Charming renovated Colonial in sought after neighborhood., vacation rental in Fairfield
Walk-To-Town Gem! Charming renovated Colonial in sought after neighborhood., vacation rental in Fairfield

Walk-To-Town Gem! Charming renovated Colonial in sought after neighborhood.

Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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PRIVATE AIRY SUMMER HOME in Minutes from the BEACH and more (WESTPORT), vacation rental in Fairfield
PRIVATE AIRY SUMMER HOME in Minutes from the BEACH and more (WESTPORT), vacation rental in Fairfield
PRIVATE AIRY SUMMER HOME in Minutes from the BEACH and more (WESTPORT), vacation rental in Fairfield

PRIVATE AIRY SUMMER HOME in Minutes from the BEACH and more (WESTPORT)

Rental Home
4 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
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Historic Updated Carriage House, vacation rental in Fairfield
Historic Updated Carriage House, vacation rental in Fairfield
Historic Updated Carriage House, vacation rental in Fairfield

Historic Updated Carriage House

Rental Home
4 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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Live/work loft with view and exposed brick, vacation rental in Fairfield
Live/work loft with view and exposed brick, vacation rental in Fairfield
Live/work loft with view and exposed brick, vacation rental in Fairfield

Live/work loft with view and exposed brick

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Riverfront retreat in the woods of scenic Weston, Connecticut., vacation rental in Fairfield
Riverfront retreat in the woods of scenic Weston, Connecticut., vacation rental in Fairfield
Riverfront retreat in the woods of scenic Weston, Connecticut., vacation rental in Fairfield

Riverfront retreat in the woods of scenic Weston, Connecticut.

Rental Home
6 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Comtemporary 1Bdr w/ Queen Bed + Free Wifi, vacation rental in Fairfield
Comtemporary 1Bdr w/ Queen Bed + Free Wifi, vacation rental in Fairfield
Comtemporary 1Bdr w/ Queen Bed + Free Wifi, vacation rental in Fairfield

Comtemporary 1Bdr w/ Queen Bed + Free Wifi

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Beautiful 3-Story Colonial Home -10 Min. from DWTN Bridgeport, vacation rental in Fairfield
Beautiful 3-Story Colonial Home -10 Min. from DWTN Bridgeport, vacation rental in Fairfield
Beautiful 3-Story Colonial Home -10 Min. from DWTN Bridgeport, vacation rental in Fairfield

Beautiful 3-Story Colonial Home -10 Min. from DWTN Bridgeport

Rental Home
5 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Lake side retreat with wow views from most rooms, vacation rental in Fairfield
Lake side retreat with wow views from most rooms, vacation rental in Fairfield
Lake side retreat with wow views from most rooms, vacation rental in Fairfield

Lake side retreat with wow views from most rooms

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Exquisite Westport Manor for Winter Vacation, vacation rental in Fairfield
Exquisite Westport Manor for Winter Vacation, vacation rental in Fairfield
Exquisite Westport Manor for Winter Vacation, vacation rental in Fairfield

Exquisite Westport Manor for Winter Vacation

Rental Home
6 bedrooms
6 bathrooms
Sleeps 12
Match: Sleeps
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My little place, vacation rental in Fairfield
My little place, vacation rental in Fairfield
My little place, vacation rental in Fairfield

My little place

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
More info
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Shanz Lofts Syle Apartment, vacation rental in Fairfield
Shanz Lofts Syle Apartment, vacation rental in Fairfield
Shanz Lofts Syle Apartment, vacation rental in Fairfield

Shanz Lofts Syle Apartment

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Charming and comfy  bedroom, vacation rental in Fairfield
Charming and comfy  bedroom, vacation rental in Fairfield
Charming and comfy  bedroom, vacation rental in Fairfield

Charming and comfy bedroom

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 1
More info
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Pied-à-terre in prestigious Long Lots area of Westport, vacation rental in Fairfield
Pied-à-terre in prestigious Long Lots area of Westport, vacation rental in Fairfield
Pied-à-terre in prestigious Long Lots area of Westport, vacation rental in Fairfield

Pied-à-terre in prestigious Long Lots area of Westport

Rental Home
1 bedroom
1 bathroom
Sleeps 1
More info
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