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Westport Holiday Rentals

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Bedrooms

Bathrooms

Amenities

Suitability

Property type

Distinctive Features

Distance from

5 mi
57 rentals in Westport.
Sunny Studio APT above historic Westport Mill, holiday rental in Westport
Sunny Studio APT above historic Westport Mill, holiday rental in Westport
Sunny Studio APT above historic Westport Mill, holiday rental in Westport

Sunny Studio APT above historic Westport Mill

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Sunny Westport 2BR Retreat above historic Mill, holiday rental in Westport
Sunny Westport 2BR Retreat above historic Mill, holiday rental in Westport
Sunny Westport 2BR Retreat above historic Mill, holiday rental in Westport

Sunny Westport 2BR Retreat above historic Mill

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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European style country chic with pool & privacy!, holiday rental in Westport
European style country chic with pool & privacy!, holiday rental in Westport
European style country chic with pool & privacy!, holiday rental in Westport

European style country chic with pool & privacy!

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Historic oyster shack., holiday rental in Westport
Historic oyster shack., holiday rental in Westport
Historic oyster shack., holiday rental in Westport

Historic oyster shack.

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 10
Match: Sleeps
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Historic Apartment in Downtown Westport, holiday rental in Westport
Historic Apartment in Downtown Westport, holiday rental in Westport
Historic Apartment in Downtown Westport, holiday rental in Westport

Historic Apartment in Downtown Westport

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Westport Paradise With Every Amenity!, holiday rental in Westport
Westport Paradise With Every Amenity!, holiday rental in Westport
Westport Paradise With Every Amenity!, holiday rental in Westport

Westport Paradise With Every Amenity!

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Your perfect Westport getaway is here!, holiday rental in Westport
Your perfect Westport getaway is here!, holiday rental in Westport
Your perfect Westport getaway is here!, holiday rental in Westport

Your perfect Westport getaway is here!

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Luxurious Water Front House -- With large dock!, holiday rental in Westport
Luxurious Water Front House -- With large dock!, holiday rental in Westport
Luxurious Water Front House -- With large dock!, holiday rental in Westport

Luxurious Water Front House -- With large dock!

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Summer rental House Westport, holiday rental in Westport
Summer rental House Westport, holiday rental in Westport
Summer rental House Westport, holiday rental in Westport

Summer rental House Westport

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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ESCAPE to Westport Direct WATERFRONT Beachouse w/Rooftop Deck, holiday rental in Westport
ESCAPE to Westport Direct WATERFRONT Beachouse w/Rooftop Deck, holiday rental in Westport
ESCAPE to Westport Direct WATERFRONT Beachouse w/Rooftop Deck, holiday rental in Westport

ESCAPE to Westport Direct WATERFRONT Beachouse w/Rooftop Deck

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Modern Waterfront Home  steps from the water in quiet beachside neighborhood, holiday rental in Westport
Modern Waterfront Home  steps from the water in quiet beachside neighborhood, holiday rental in Westport
Modern Waterfront Home  steps from the water in quiet beachside neighborhood, holiday rental in Westport

Modern Waterfront Home steps from the water in quiet beachside neighborhood

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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3 Bedroom Luxury Cape - Walk To Train & Beach, holiday rental in Westport
3 Bedroom Luxury Cape - Walk To Train & Beach, holiday rental in Westport
3 Bedroom Luxury Cape - Walk To Train & Beach, holiday rental in Westport

3 Bedroom Luxury Cape - Walk To Train & Beach

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Cozy House Westport., holiday rental in Westport
Cozy House Westport., holiday rental in Westport
Cozy House Westport., holiday rental in Westport

Cozy House Westport.

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Waterfront Getaway - Saugatuck Shores, Westport, holiday rental in Westport
Waterfront Getaway - Saugatuck Shores, Westport, holiday rental in Westport
Waterfront Getaway - Saugatuck Shores, Westport, holiday rental in Westport

Waterfront Getaway - Saugatuck Shores, Westport

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
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Westport, CT - Walk To The Beach - NYC Getaway, holiday rental in Westport
Westport, CT - Walk To The Beach - NYC Getaway, holiday rental in Westport
Westport, CT - Walk To The Beach - NYC Getaway, holiday rental in Westport

Westport, CT - Walk To The Beach - NYC Getaway

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Newly Renovated Home in Westport CT, Private Pool, Walk to Town, Close to Beach, holiday rental in Westport
Newly Renovated Home in Westport CT, Private Pool, Walk to Town, Close to Beach, holiday rental in Westport
Newly Renovated Home in Westport CT, Private Pool, Walk to Town, Close to Beach, holiday rental in Westport

Newly Renovated Home in Westport CT, Private Pool, Walk to Town, Close to Beach

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Monthly Rental-4 Bedroom Colonial in Westport, CT, holiday rental in Westport
Monthly Rental-4 Bedroom Colonial in Westport, CT, holiday rental in Westport
Monthly Rental-4 Bedroom Colonial in Westport, CT, holiday rental in Westport

Monthly Rental-4 Bedroom Colonial in Westport, CT

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Endless water views on estate property and walk to downtown and beaches!, holiday rental in Westport
Endless water views on estate property and walk to downtown and beaches!, holiday rental in Westport
Endless water views on estate property and walk to downtown and beaches!, holiday rental in Westport

Endless water views on estate property and walk to downtown and beaches!

Holiday Rental House
5 bedrooms
8 bathrooms
Sleeps 12
Match: Sleeps
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Affiliated with FlipKey
Amazing New Construction Home with Large Yard.  5 Minutes to EVERYTHING!, holiday rental in Westport
Amazing New Construction Home with Large Yard.  5 Minutes to EVERYTHING!, holiday rental in Westport
Amazing New Construction Home with Large Yard.  5 Minutes to EVERYTHING!, holiday rental in Westport

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

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Westport: Walk to Town (Really) Private Yard, One Floor, holiday rental in Westport
Westport: Walk to Town (Really) Private Yard, One Floor, holiday rental in Westport
Westport: Walk to Town (Really) Private Yard, One Floor, holiday rental in Westport

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

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Ideal location-Compo Beach, Longshore Park, fine dining
academic-term potential, holiday rental in Westport
Ideal location-Compo Beach, Longshore Park, fine dining
academic-term potential, holiday rental in Westport
Ideal location-Compo Beach, Longshore Park, fine dining
academic-term potential, holiday rental in Westport

Ideal location-Compo Beach, Longshore Park, fine dining academic-term potential

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Walk-To-Town Cozy Colonial with Fireplace!, holiday rental in Westport
Walk-To-Town Cozy Colonial with Fireplace!, holiday rental in Westport
Walk-To-Town Cozy Colonial with Fireplace!, holiday rental in Westport

Walk-To-Town Cozy Colonial with Fireplace!

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Spacious Family Home, holiday rental in Westport
Spacious Family Home, holiday rental in Westport
Spacious Family Home, holiday rental in Westport

Spacious Family Home

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Mill Pond Retreat, holiday rental in Westport
Mill Pond Retreat, holiday rental in Westport
Mill Pond Retreat, holiday rental in Westport

Mill Pond Retreat

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Modern Farmhouse, holiday rental in Westport
Modern Farmhouse, holiday rental in Westport
Modern Farmhouse, holiday rental in Westport

Modern Farmhouse

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Beautiful Westport Historic 4 Bedroom Gem, holiday rental in Westport
Beautiful Westport Historic 4 Bedroom Gem, holiday rental in Westport
Beautiful Westport Historic 4 Bedroom Gem, holiday rental in Westport

Beautiful Westport Historic 4 Bedroom Gem

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 2
Match: Sleeps
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Pool & beach vacation in Westport, Connecticut, holiday rental in Westport
Pool & beach vacation in Westport, Connecticut, holiday rental in Westport
Pool & beach vacation in Westport, Connecticut, holiday rental in Westport

Pool & beach vacation in Westport, Connecticut

Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 7
Match: Sleeps
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Your luxury dream villa! �, holiday rental in Westport
Your luxury dream villa! �, holiday rental in Westport
Your luxury dream villa! �, holiday rental in Westport

Your luxury dream villa! �

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Vacation Home away from home with private pool-mins away from beach, holiday rental in Westport
Vacation Home away from home with private pool-mins away from beach, holiday rental in Westport
Vacation Home away from home with private pool-mins away from beach, holiday rental in Westport

Vacation Home away from home with private pool-mins away from beach

Holiday Rental House
6 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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5500 sqft SUMMER HOME in Minutes from the BEACH + more (WESTPORT), holiday rental in Westport
5500 sqft SUMMER HOME in Minutes from the BEACH + more (WESTPORT), holiday rental in Westport
5500 sqft SUMMER HOME in Minutes from the BEACH + more (WESTPORT), holiday rental in Westport

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

Holiday Rental House
4 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
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Fabulous private home on desirable street in Westport., holiday rental in Westport
Fabulous private home on desirable street in Westport., holiday rental in Westport
Fabulous private home on desirable street in Westport., holiday rental in Westport

Fabulous private home on desirable street in Westport.

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Spectacular Country Home, holiday rental in Westport
Spectacular Country Home, holiday rental in Westport
Spectacular Country Home, holiday rental in Westport

Spectacular Country Home

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Classic Colonial Farmhouse with lush garden near the beach, holiday rental in Westport
Classic Colonial Farmhouse with lush garden near the beach, holiday rental in Westport
Classic Colonial Farmhouse with lush garden near the beach, holiday rental in Westport

Classic Colonial Farmhouse with lush garden near the beach

Holiday Rental House
4 bedrooms
5 bathrooms
Sleeps 8
Match: Sleeps
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Westport Summer Estate, holiday rental in Westport
Westport Summer Estate, holiday rental in Westport
Westport Summer Estate, holiday rental in Westport

Westport Summer Estate

Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Private Oasis in Westport with heated pool!, holiday rental in Westport
Private Oasis in Westport with heated pool!, holiday rental in Westport
Private Oasis in Westport with heated pool!, holiday rental in Westport

Private Oasis in Westport with heated pool!

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Summer in Westport, CT! - Renovated, Private, Close to everything!, holiday rental in Westport
Summer in Westport, CT! - Renovated, Private, Close to everything!, holiday rental in Westport
Summer in Westport, CT! - Renovated, Private, Close to everything!, holiday rental in Westport

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

Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Real log house on Directly on the River with heated pool one hour from NYC., holiday rental in Westport
Real log house on Directly on the River with heated pool one hour from NYC., holiday rental in Westport
Real log house on Directly on the River with heated pool one hour from NYC., holiday rental in Westport

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

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Private Oasis: Completely Renovated Old Farmhouse With Pool And Guesthouse, holiday rental in Westport
Private Oasis: Completely Renovated Old Farmhouse With Pool And Guesthouse, holiday rental in Westport
Private Oasis: Completely Renovated Old Farmhouse With Pool And Guesthouse, holiday rental in Westport

Private Oasis: Completely Renovated Old Farmhouse With Pool And Guesthouse

Holiday Rental House
4 bedrooms
5 bathrooms
Sleeps 8
Match: Sleeps
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Luxury beach home at Compo Beach, Westport CT, holiday rental in Westport
Luxury beach home at Compo Beach, Westport CT, holiday rental in Westport
Luxury beach home at Compo Beach, Westport CT, holiday rental in Westport

Luxury beach home at Compo Beach, Westport CT

Holiday Rental House
4 bedrooms
5 bathrooms
Sleeps 7
Match: Sleeps
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Dramatic family home directly on the Saugatuck River in Westport, CT, holiday rental in Westport
Dramatic family home directly on the Saugatuck River in Westport, CT, holiday rental in Westport
Dramatic family home directly on the Saugatuck River in Westport, CT, holiday rental in Westport

Dramatic family home directly on the Saugatuck River in Westport, CT

Holiday Rental House
5 bedrooms
5 bathrooms
Sleeps 8
Match: Sleeps
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Beautiful Summer Escape, holiday rental in Westport
Beautiful Summer Escape, holiday rental in Westport
Beautiful Summer Escape, holiday rental in Westport

Beautiful Summer Escape

Holiday Rental House
5 bedrooms
7 bathrooms
Sleeps 10
Match: Sleeps
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Westport summer 5 bed home on quiet street 6 mins to the beach!, holiday rental in Westport
Westport summer 5 bed home on quiet street 6 mins to the beach!, holiday rental in Westport
Westport summer 5 bed home on quiet street 6 mins to the beach!, holiday rental in Westport

Westport summer 5 bed home on quiet street 6 mins to the beach!

Holiday Rental House
5 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
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Exquisite Waterfront Villa, holiday rental in Westport
Exquisite Waterfront Villa, holiday rental in Westport
Exquisite Waterfront Villa, holiday rental in Westport

Exquisite Waterfront Villa

Holiday Rental House
4 bedrooms
6 bathrooms
Sleeps 8
Match: Sleeps
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Westport Wonder Summer Rental with Pool!, holiday rental in Westport
Westport Wonder Summer Rental with Pool!, holiday rental in Westport
Westport Wonder Summer Rental with Pool!, holiday rental in Westport

Westport Wonder Summer Rental with Pool!

Holiday Rental House
5 bedrooms
6 bathrooms
Sleeps 8
Match: Sleeps
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Chic, Impeccably Decorated 5000 sq ft Estate, Coveted Greens Farms, Summer Rentl, holiday rental in Westport
Chic, Impeccably Decorated 5000 sq ft Estate, Coveted Greens Farms, Summer Rentl, holiday rental in Westport
Chic, Impeccably Decorated 5000 sq ft Estate, Coveted Greens Farms, Summer Rentl, holiday rental in Westport

Chic, Impeccably Decorated 5000 sq ft Estate, Coveted Greens Farms, Summer Rentl

Holiday Rental House
5 bedrooms
6 bathrooms
Sleeps 8
Match: Sleeps
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Newly renovated 6BR, Pool, Spa, ScreenPorch, 2 private acres, Heart of Westport., holiday rental in Westport
Newly renovated 6BR, Pool, Spa, ScreenPorch, 2 private acres, Heart of Westport., holiday rental in Westport
Newly renovated 6BR, Pool, Spa, ScreenPorch, 2 private acres, Heart of Westport., holiday rental in Westport

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

Holiday Rental House
6 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
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June to Sept Rental, Spectacular Views, INFINITY Pool, Perfect Location, holiday rental in Westport
June to Sept Rental, Spectacular Views, INFINITY Pool, Perfect Location, holiday rental in Westport
June to Sept Rental, Spectacular Views, INFINITY Pool, Perfect Location, holiday rental in Westport

June to Sept Rental, Spectacular Views, INFINITY Pool, Perfect Location

Holiday Rental House
5 bedrooms
6 bathrooms
Sleeps 10
Match: Sleeps
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Walk-to-Town New home w/new furnishings, Grill Center & Playset, holiday rental in Westport
Walk-to-Town New home w/new furnishings, Grill Center & Playset, holiday rental in Westport
Walk-to-Town New home w/new furnishings, Grill Center & Playset, holiday rental in Westport

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

Holiday Rental House
5 bedrooms
6 bathrooms
Sleeps 10
Match: Sleeps
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Newly renovated summer home in Westport CT private pool & spa, near beach & town, holiday rental in Westport
Newly renovated summer home in Westport CT private pool & spa, near beach & town, holiday rental in Westport
Newly renovated summer home in Westport CT private pool & spa, near beach & town, holiday rental in Westport

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

Holiday Rental House
6 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
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Designer Modern Westport Estate, holiday rental in Westport
Designer Modern Westport Estate, holiday rental in Westport
Designer Modern Westport Estate, holiday rental in Westport

Designer Modern Westport Estate

Holiday Rental House
5 bedrooms
7 bathrooms
Sleeps 12
Match: Sleeps
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Showing results 1-50 of 57
Frequently Asked Questions about Westport