Vacation rentals in Westport, CT

Best vacation rentals and Airbnb offers in Westport, CT

Cozy 2 bedroom 2 bath house with in charming private house near Fairfield Border

Holiday Home, Westport

Cozy 2 bedroom 2 bath house with in charming private house near Fairfield Border is a holiday home in Westport, with pet-friendly space, parking, and kitchen access. This stay gives…

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About Cozy 2 bedroom 2 bath house with in charming private house near Fairfield Border

Cozy 2 bedroom 2 bath house with in charming private house near Fairfield Border is a holiday home in Westport, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: pet friendly, pets friendly, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,051.

From$150/night

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Lovely 1-bedroom Basement apartment in Stamford

Apartment, Westport

Lovely 1-bedroom Basement apartment in Stamford is a apartment in Westport, with pet-friendly space and room for a group. This stay gives travelers a comfortable base for exploring the…

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About Lovely 1-bedroom Basement apartment in Stamford

Lovely 1-bedroom Basement apartment in Stamford is a apartment in Westport, with pet-friendly space and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pet friendly, pets friendly, washer, and heating.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,071.

From$153/night

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Stamford : The Comfy Cove Hideout

Holiday Home, Westport

Stamford : The Comfy Cove Hideout is a holiday home in Westport, with pet-friendly space. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and…

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About Stamford : The Comfy Cove Hideout

Stamford : The Comfy Cove Hideout is a holiday home in Westport, with pet-friendly space. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pet friendly, pets friendly, ac, and air conditioning.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,085.

From$155/night

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Charming 2-bedroom apartment in delightful Bridgeport with WiFi

Apartment, Westport

Charming 2-bedroom apartment in delightful Bridgeport with WiFi is a apartment in Westport, with parking and room for a group. This stay gives travelers a comfortable base for exploring the…

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About Charming 2-bedroom apartment in delightful Bridgeport with WiFi

Charming 2-bedroom apartment in delightful Bridgeport with WiFi is a apartment in Westport, with parking and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, parking, free parking, heating, and internet.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,151.

From$164/night

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Vacation rentals with a pool in Westport, CT

Add a pool to the search when you want an easy place to cool off between outings.

Spacious Easton 2BR Townhouse with Big Yard

Condo, Westport

Spacious Easton 2BR Townhouse with Big Yard is a condo in Westport, with pet-friendly space, pool access, and room for a group. This stay gives travelers a comfortable base for exploring…

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About Spacious Easton 2BR Townhouse with Big Yard

Spacious Easton 2BR Townhouse with Big Yard is a condo in Westport, with pet-friendly space, pool access, and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: pool, hot tub, pet friendly, and pets friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,497.

From$357/night

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Guest House at Norwalk Inn

Guest House, Westport

Guest House at Norwalk Inn is a guest house in Westport, with pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time…

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About Guest House at Norwalk Inn

Guest House at Norwalk Inn is a guest house in Westport, with pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, free wifi, and gym.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,292.

From$409/night

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Modern 4 bed 4.5 bath w hot tub & heated pool close to beach

Holiday Home, Westport

Modern 4 bed 4.5 bath w hot tub & heated pool close to beach is a holiday home in Westport, with pool access and easy beach access. This stay gives travelers a comfortable base for…

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About Modern 4 bed 4.5 bath w hot tub & heated pool close to beach

Modern 4 bed 4.5 bath w hot tub & heated pool close to beach is a holiday home in Westport, with pool access and easy beach access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: pool, hot tub, and free wifi.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $10,224.

From$1,461/night

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Westport Dream Home 6 Bedroom / 5 Bathroom Pool and Jacuzzi Steps to town

Holiday Home, Westport

Westport Dream Home 6 Bedroom / 5 Bathroom Pool and Jacuzzi Steps to town is a holiday home in Westport, with pool access and room for a group. This stay gives travelers a comfortable base…

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About Westport Dream Home 6 Bedroom / 5 Bathroom Pool and Jacuzzi Steps to town

Westport Dream Home 6 Bedroom / 5 Bathroom Pool and Jacuzzi Steps to town is a holiday home in Westport, with pool access and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, gym, washer, and dryer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $14,395.

From$2,056/night

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Vacation rentals with parking in Westport, CT

Find vacation rentals that make arriving by car easier.

<br>❤️High-Line Harbor Flat 2 BD | Train🚊 | Harbor Point Access | 40 Minutes to NYC🗽

Apartment, Westport

<br>❤️High-Line Harbor Flat 2 BD · Train🚊 · Harbor Point Access · 40 Minutes to NYC🗽 is a apartment in Westport, with parking, kitchen access, and room for a group. This stay gives…

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About <br>❤️High-Line Harbor Flat 2 BD | Train🚊 | Harbor Point Access | 40 Minutes to NYC🗽

<br>❤️High-Line Harbor Flat 2 BD · Train🚊 · Harbor Point Access · 40 Minutes to NYC🗽 is a apartment in Westport, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free wifi, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,230.

From$176/night

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Serenity Haven: A Modern Retreat

Holiday Home, Westport

Serenity Haven: A Modern Retreat is a holiday home in Westport, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Serenity Haven: A Modern Retreat

Serenity Haven: A Modern Retreat is a holiday home in Westport, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: pet friendly, pets friendly, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,607.

From$230/night

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59 Rennell St, Bridgeport · Lovely 1 bedroom cozy modern apartment w/75” 4K TV

Apartment, Westport

59 Rennell St, Bridgeport · Lovely 1 bedroom cozy modern apartment w/75” 4K TV is a apartment in Westport, with parking, kitchen access, and room for a group. This stay gives travelers a…

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About 59 Rennell St, Bridgeport · Lovely 1 bedroom cozy modern apartment w/75” 4K TV

59 Rennell St, Bridgeport · Lovely 1 bedroom cozy modern apartment w/75” 4K TV is a apartment in Westport, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: kitchen, with kitchen, parking, free parking, and fireplace.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,752.

From$250/night

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Darien Home

Holiday Home, Westport

Darien Home is a holiday home in Westport, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time…

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About Darien Home

Darien Home is a holiday home in Westport, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,826.

From$261/night

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Pet-friendly vacation rentals in Westport, CT

Bring your pet along with stays that welcome four-legged travelers.

3 Bedrm Apt at Black Rock Suites

Apartment, Westport

3 Bedrm Apt at Black Rock Suites is a apartment in Westport, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About 3 Bedrm Apt at Black Rock Suites

3 Bedrm Apt at Black Rock Suites is a apartment in Westport, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,213.

From$316/night

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Modern 3-Bdrm Apt in Black Rock

Apartment, Westport

Modern 3-Bdrm Apt in Black Rock is a apartment in Westport, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Modern 3-Bdrm Apt in Black Rock

Modern 3-Bdrm Apt in Black Rock is a apartment in Westport, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,213.

From$316/night

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Modern House in Black Rock

Holiday Home, Westport

Modern House in Black Rock is a holiday home in Westport, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Modern House in Black Rock

Modern House in Black Rock is a holiday home in Westport, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,223.

From$318/night

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Westport: Walk to Town, Private Natural Setting, Lovely Neighborhood

Holiday Home, Westport

Westport: Walk to Town, Private Natural Setting, Lovely Neighborhood is a holiday home in Westport, with pet-friendly space. This stay gives travelers a comfortable base for exploring the…

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About Westport: Walk to Town, Private Natural Setting, Lovely Neighborhood

Westport: Walk to Town, Private Natural Setting, Lovely Neighborhood is a holiday home in Westport, with pet-friendly space. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, hot tub, free wifi, pet friendly, and pets friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $5,607.

From$801/night

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Vacation rentals with a kitchen in Westport, CT

Compare stays with kitchen access for longer trips and easier meals.

THIS IS MY HAPPY PLACE

Apartment, Westport

THIS IS MY HAPPY PLACE is a apartment in Westport, with kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with…

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About THIS IS MY HAPPY PLACE

THIS IS MY HAPPY PLACE is a apartment in Westport, with kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: kitchen, with kitchen, ac, air conditioning, and tv.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,177.

From$168/night

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Modern Luxe 1BR Apt in Downtown Stamford

Apartment, Westport

Modern Luxe 1BR Apt in Downtown Stamford is a apartment in Westport, with kitchen access and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Modern Luxe 1BR Apt in Downtown Stamford

Modern Luxe 1BR Apt in Downtown Stamford is a apartment in Westport, with kitchen access and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, kitchen, with kitchen, and gym.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,400.

From$200/night

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The Blue Sapphire: Modern & Stylish 2BR w/ 2 King Beds & Full Kitchen

Apartment, Westport

The Blue Sapphire: Modern & Stylish 2BR w/ 2 King Beds & Full Kitchen is a apartment in Westport, with kitchen access and room for a group. This stay gives travelers a comfortable base for…

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About The Blue Sapphire: Modern & Stylish 2BR w/ 2 King Beds & Full Kitchen

The Blue Sapphire: Modern & Stylish 2BR w/ 2 King Beds & Full Kitchen is a apartment in Westport, with kitchen access and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, kitchen, with kitchen, ac, and air conditioning.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,653.

From$236/night

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Lavish 1 bed Apt + Rooftop & Gym - Downtown Stamford

Apartment, Westport

Lavish 1 bed Apt + Rooftop & Gym - Downtown Stamford is a apartment in Westport, with kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About Lavish 1 bed Apt + Rooftop & Gym - Downtown Stamford

Lavish 1 bed Apt + Rooftop & Gym - Downtown Stamford is a apartment in Westport, with kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, kitchen, with kitchen, and gym.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,993.

From$285/night

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Family-friendly vacation rentals in Westport, CT

Plan a trip with stays that give families more room to spread out.

Family-Friendly 2BR with Parking Near NYC + Hospital

Apartment, Westport

Family-Friendly 2BR with Parking Near NYC + Hospital is a apartment in Westport, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for…

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About Family-Friendly 2BR with Parking Near NYC + Hospital

Family-Friendly 2BR with Parking Near NYC + Hospital is a apartment in Westport, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,687.

From$241/night

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Cozy country cottage in horse country ,private 1 hour toNYC

Cottage, Westport

Cozy country cottage in horse country ,private 1 hour toNYC is a cottage in Westport, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring…

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About Cozy country cottage in horse country ,private 1 hour toNYC

Cozy country cottage in horse country ,private 1 hour toNYC is a cottage in Westport, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, pet friendly, pets friendly, and kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,780.

From$254/night

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Modern Home off I-95 Perfect for Families & Business Stay with Ample Parking

Villa, Westport

Modern Home off I-95 Perfect for Families & Business Stay with Ample Parking is a villa in Westport, with pet-friendly space and parking. This stay gives travelers a comfortable base for…

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About Modern Home off I-95 Perfect for Families & Business Stay with Ample Parking

Modern Home off I-95 Perfect for Families & Business Stay with Ample Parking is a villa in Westport, with pet-friendly space and parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, pet friendly, pets friendly, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,899.

From$333/night

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Seaside Serenity: 2B 1B, Patio,Near Beach

Cottage, Westport

Seaside Serenity: 2B 1B, Patio,Near Beach is a cottage in Westport, with pet-friendly space, easy beach access, and outdoor space. This stay gives travelers a comfortable base for exploring…

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About Seaside Serenity: 2B 1B, Patio,Near Beach

Seaside Serenity: 2B 1B, Patio,Near Beach is a cottage in Westport, with pet-friendly space, easy beach access, and outdoor space. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free wifi, pet friendly, pets friendly, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,660.

From$380/night

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