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Westport Vacation Rentals

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41 rentals in Westport.
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Ideal Westport location - Compo Beach, Longshore Club Park, fine dining, vacation rental in Westport
Ideal Westport location - Compo Beach, Longshore Club Park, fine dining, vacation rental in Westport
Ideal Westport location - Compo Beach, Longshore Club Park, fine dining, vacation rental in Westport

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, vacation rental in Westport
Westport: Walk to Town (Really) Private Yard, One Floor, vacation rental in Westport
Westport: Walk to Town (Really) Private Yard, One Floor, vacation rental in Westport

Westport: Walk to Town (Really) Private Yard, One Floor

Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Nama-stay, sweet pink Saugatuck Shores beach cottage, vacation rental in Westport
Nama-stay, sweet pink Saugatuck Shores beach cottage, vacation rental in Westport
Nama-stay, sweet pink Saugatuck Shores beach cottage, vacation rental in Westport

Nama-stay, sweet pink Saugatuck Shores beach cottage

Rental Home
3 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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1/2 block to Compo Beach on Long Island Sound!, vacation rental in Westport
1/2 block to Compo Beach on Long Island Sound!, vacation rental in Westport
1/2 block to Compo Beach on Long Island Sound!, vacation rental in Westport

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

Rental Home
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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A private summer compound in Westport, CT - total seclusion yet close to it all, vacation rental in Westport
A private summer compound in Westport, CT - total seclusion yet close to it all, vacation rental in Westport
A private summer compound in Westport, CT - total seclusion yet close to it all, vacation rental in Westport

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

Rental Home
6 bedrooms
8 bathrooms
Sleeps 12
Match: Sleeps
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Modern Waterfront Home  
steps from the water in quiet beachside neighborhood, vacation rental in Westport
Modern Waterfront Home  
steps from the water in quiet beachside neighborhood, vacation rental in Westport
Modern Waterfront Home  
steps from the water in quiet beachside neighborhood, vacation rental in Westport

Modern Waterfront Home steps from the water in quiet beachside neighborhood

Rental Home
3 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Mill Pond Retreat, vacation rental in Westport
Mill Pond Retreat, vacation rental in Westport
Mill Pond Retreat, vacation rental in Westport

Mill Pond Retreat

Rental Home
4 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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New modern house near the water (WESTPORT RESIDENTS ONLY), vacation rental in Westport
New modern house near the water (WESTPORT RESIDENTS ONLY), vacation rental in Westport
New modern house near the water (WESTPORT RESIDENTS ONLY), vacation rental in Westport

New modern house near the water (WESTPORT RESIDENTS ONLY)

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Suburban Getaway. Heated Pool. NO PARTIES., vacation rental in Westport
Suburban Getaway. Heated Pool. NO PARTIES., vacation rental in Westport
Suburban Getaway. Heated Pool. NO PARTIES., vacation rental in Westport

Suburban Getaway. Heated Pool. NO PARTIES.

Rental Home
5 bedrooms
3 bathrooms
Sleeps 11
Match: Sleeps
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Summer in Westport, CT! - Renovated, Private, Close to everything!, vacation rental in Westport
Summer in Westport, CT! - Renovated, Private, Close to everything!, vacation rental in Westport
Summer in Westport, CT! - Renovated, Private, Close to everything!, vacation rental in Westport

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

Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Newly renovated 6BR, Pool, Spa, ScreenPorch, 2 private acres, Heart of Westport., vacation rental in Westport
Newly renovated 6BR, Pool, Spa, ScreenPorch, 2 private acres, Heart of Westport., vacation rental in Westport
Newly renovated 6BR, Pool, Spa, ScreenPorch, 2 private acres, Heart of Westport., vacation rental in Westport

Newly renovated 6BR, Pool, Spa, ScreenPorch, 2 private acres, Heart of Westport.

Rental Home
6 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
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Modern Farmhouse - Recently Renovated, vacation rental in Westport
Modern Farmhouse - Recently Renovated, vacation rental in Westport
Modern Farmhouse - Recently Renovated, vacation rental in Westport

Modern Farmhouse - Recently Renovated

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

Historic Apartment in Downtown Westport

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Historic oyster shack., vacation rental in Westport
Historic oyster shack., vacation rental in Westport
Historic oyster shack., vacation rental in Westport

Historic oyster shack.

Rental Home
1 bedroom
1 bathroom
Sleeps 10
Match: Sleeps
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Dramatic Waterfront Family Home Directly on the Saugatuck River in Westport, CT, vacation rental in Westport
Dramatic Waterfront Family Home Directly on the Saugatuck River in Westport, CT, vacation rental in Westport
Dramatic Waterfront Family Home Directly on the Saugatuck River in Westport, CT, vacation rental in Westport

Dramatic Waterfront Family Home Directly on the Saugatuck River in Westport, CT

Rental Home
5 bedrooms
5 bathrooms
Sleeps 8
Match: Sleeps
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Beautiful Summer Escape, vacation rental in Westport
Beautiful Summer Escape, vacation rental in Westport
Beautiful Summer Escape, vacation rental in Westport

Beautiful Summer Escape

Rental Home
5 bedrooms
7 bathrooms
Sleeps 10
Match: Sleeps
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Newly renovated summer home in Westport CT private pool & spa, near beach & town, vacation rental in Westport
Newly renovated summer home in Westport CT private pool & spa, near beach & town, vacation rental in Westport
Newly renovated summer home in Westport CT private pool & spa, near beach & town, vacation rental in Westport

Newly renovated summer home in Westport CT private pool & spa, near beach & town

Rental Home
6 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
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Summer rental House Westport, vacation rental in Westport
Summer rental House Westport, vacation rental in Westport
Summer rental House Westport, vacation rental in Westport

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 Westport
Real log house on Directly on the River with heated pool one hour from NYC., vacation rental in Westport
Real log house on Directly on the River with heated pool one hour from NYC., vacation rental in Westport

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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Spectacular Country Home, vacation rental in Westport
Spectacular Country Home, vacation rental in Westport
Spectacular Country Home, vacation rental in Westport

Spectacular Country Home

Rental Home
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Historic Updated Carriage House, vacation rental in Westport
Historic Updated Carriage House, vacation rental in Westport
Historic Updated Carriage House, vacation rental in Westport

Historic Updated Carriage House

Rental Home
4 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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Exquisite Westport Manor for Winter Vacation, vacation rental in Westport
Exquisite Westport Manor for Winter Vacation, vacation rental in Westport
Exquisite Westport Manor for Winter Vacation, vacation rental in Westport

Exquisite Westport Manor for Winter Vacation

Rental Home
6 bedrooms
6 bathrooms
Sleeps 12
Match: Sleeps
More info
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Amazing New Construction Home with Large Yard.  5 Minutes to EVERYTHING!, vacation rental in Westport
Amazing New Construction Home with Large Yard.  5 Minutes to EVERYTHING!, vacation rental in Westport
Amazing New Construction Home with Large Yard.  5 Minutes to EVERYTHING!, vacation rental in Westport

Amazing New Construction Home with Large Yard. 5 Minutes to EVERYTHING!

Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
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Family friendly home with an open floor plan on an acre of wooded land, vacation rental in Westport
Family friendly home with an open floor plan on an acre of wooded land, vacation rental in Westport
Family friendly home with an open floor plan on an acre of wooded land, vacation rental in Westport

Family friendly home with an open floor plan on an acre of wooded land

Rental Home
3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
More info
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Waterfront Getaway - Saugatuck Shores, Westport, vacation rental in Westport
Waterfront Getaway - Saugatuck Shores, Westport, vacation rental in Westport
Waterfront Getaway - Saugatuck Shores, Westport, vacation rental in Westport

Waterfront Getaway - Saugatuck Shores, Westport

Rental Home
4 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
More info
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Vacation Ready: Beautiful House with Heated Pool, vacation rental in Westport
Vacation Ready: Beautiful House with Heated Pool, vacation rental in Westport
Vacation Ready: Beautiful House with Heated Pool, vacation rental in Westport

Vacation Ready: Beautiful House with Heated Pool

Rental Home
6 bedrooms
7 bathrooms
Sleeps 11
Match: Sleeps
More info
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Pool & beach vacation in Westport, Connecticut, vacation rental in Westport
Pool & beach vacation in Westport, Connecticut, vacation rental in Westport
Pool & beach vacation in Westport, Connecticut, vacation rental in Westport

Pool & beach vacation in Westport, Connecticut

Rental Home
5 bedrooms
4 bathrooms
Sleeps 7
Match: Sleeps
More info
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Walk-To-Town Gem! Charming renovated Colonial in sought after neighborhood., vacation rental in Westport
Walk-To-Town Gem! Charming renovated Colonial in sought after neighborhood., vacation rental in Westport
Walk-To-Town Gem! Charming renovated Colonial in sought after neighborhood., vacation rental in Westport

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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Amazing  Westport Beach House Just One Block From Compo Beach, vacation rental in Westport
Amazing  Westport Beach House Just One Block From Compo Beach, vacation rental in Westport
Amazing  Westport Beach House Just One Block From Compo Beach, vacation rental in Westport

Amazing Westport Beach House Just One Block From Compo Beach

Rental Home
5 bedrooms
5 bathrooms
Sleeps 8
Match: Sleeps
More info
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5500 sqft SUMMER HOME in Minutes from the BEACH + more (WESTPORT), vacation rental in Westport
5500 sqft SUMMER HOME in Minutes from the BEACH + more (WESTPORT), vacation rental in Westport
5500 sqft SUMMER HOME in Minutes from the BEACH + more (WESTPORT), vacation rental in Westport

5500 sqft SUMMER HOME in Minutes from the BEACH + more (WESTPORT)

Rental Home
4 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
More info
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Luxurious Water Front House -- With large dock!, vacation rental in Westport
Luxurious Water Front House -- With large dock!, vacation rental in Westport
Luxurious Water Front House -- With large dock!, vacation rental in Westport

Luxurious Water Front House -- With large dock!

Rental Home
3 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
More info
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Westport Villa- Luxury Pool, Spa - minutes from Town & Compo Beach, vacation rental in Westport
Westport Villa- Luxury Pool, Spa - minutes from Town & Compo Beach, vacation rental in Westport
Westport Villa- Luxury Pool, Spa - minutes from Town & Compo Beach, vacation rental in Westport

Westport Villa- Luxury Pool, Spa - minutes from Town & Compo Beach

Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
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Coastal Summer Haven | Walk to Beach | Rooftop Deck w/ Amazing Views, vacation rental in Westport
Coastal Summer Haven | Walk to Beach | Rooftop Deck w/ Amazing Views, vacation rental in Westport
Coastal Summer Haven | Walk to Beach | Rooftop Deck w/ Amazing Views, vacation rental in Westport

Coastal Summer Haven | Walk to Beach | Rooftop Deck w/ Amazing Views

Rental Home
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Every Amenity, Right Here!, vacation rental in Westport
Every Amenity, Right Here!, vacation rental in Westport
Every Amenity, Right Here!, vacation rental in Westport

Every Amenity, Right Here!

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Beautiful Old Hill Colonial, vacation rental in Westport
Beautiful Old Hill Colonial, vacation rental in Westport
Beautiful Old Hill Colonial, vacation rental in Westport

Beautiful Old Hill Colonial

Rental Home
6 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Westport, CT - Walk To The Beach - NYC Getaway, vacation rental in Westport
Westport, CT - Walk To The Beach - NYC Getaway, vacation rental in Westport
Westport, CT - Walk To The Beach - NYC Getaway, vacation rental in Westport

Westport, CT - Walk To The Beach - NYC Getaway

Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Upscale custom home minutes from NYC, vacation rental in Westport
Upscale custom home minutes from NYC, vacation rental in Westport
Upscale custom home minutes from NYC, vacation rental in Westport

Upscale custom home minutes from NYC

Rental Home
3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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Walk-to-Town New home w/new furnishings, Grill Center & Playset, vacation rental in Westport
Walk-to-Town New home w/new furnishings, Grill Center & Playset, vacation rental in Westport
Walk-to-Town New home w/new furnishings, Grill Center & Playset, vacation rental in Westport

Walk-to-Town New home w/new furnishings, Grill Center & Playset

Rental Home
6 bedrooms
6 bathrooms
Sleeps 10
Match: Sleeps
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Luxurious, Spacious Property 7 min from beach & town, 1hr from NYC with discount, vacation rental in Westport
Luxurious, Spacious Property 7 min from beach & town, 1hr from NYC with discount, vacation rental in Westport
Luxurious, Spacious Property 7 min from beach & town, 1hr from NYC with discount, vacation rental in Westport

Luxurious, Spacious Property 7 min from beach & town, 1hr from NYC with discount

Rental Home
8 bedrooms
8 bathrooms
Sleeps 15
Match: Sleeps
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Westport,Compo Beach 4 bedroom 2bath private home, vacation rental in Westport
Westport,Compo Beach 4 bedroom 2bath private home, vacation rental in Westport
Westport,Compo Beach 4 bedroom 2bath private home, vacation rental in Westport

Westport,Compo Beach 4 bedroom 2bath private home

Rental Home
4 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Westport Villa- Luxury Pool & Spa, vacation rental in Westport
Westport Villa- Luxury Pool & Spa, vacation rental in Westport
Westport Villa- Luxury Pool & Spa, vacation rental in Westport

Westport Villa- Luxury Pool & Spa

Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Pied-à-terre in prestigious Long Lots area of Westport, vacation rental in Westport
Pied-à-terre in prestigious Long Lots area of Westport, vacation rental in Westport
Pied-à-terre in prestigious Long Lots area of Westport, vacation rental in Westport

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

Rental Home
1 bedroom
1 bathroom
Sleeps 1
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