Find Vacation Rentals in Southport, Fairfield

We have 54 properties to choose from
Westport
Anytime
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Popular Westport Vacation Rentals

Find the perfect Westport vacation rental

Cottage Westport
$403 per night
Cottage ∙ 4 guests ∙ 2 bedrooms
Westport, Fairfield County, Connecticut, United States
Details
Vrbo
Details
Details
House Westport
$856 per night
House ∙ 8 guests ∙ 4 bedrooms
Westport, Fairfield County, Connecticut, United States
Details
Vrbo
Details
Details
House Westport
$440 per night
House ∙ 6 guests ∙ 3 bedrooms
4.4
Very good (20 ratings)
Westport, Fairfield County, Connecticut, United States
Details
Vrbo
Details
Details
Apartment Westport
$100 per night
Apartment ∙ 4 guests ∙ 1 bedroom
4.9
Outstanding (60 ratings)
Westport, Fairfield County, Connecticut, United States
Details
Vrbo
Details
Details
Apartment Westport
$147 per night
Apartment ∙ 6 guests ∙ 2 bedrooms
5.0
Outstanding (2 ratings)
Westport, Fairfield County, Connecticut, United States
Details
Vrbo
Details
Details
Cottage Westport
$500 per night
Cottage ∙ 6 guests ∙ 4 bedrooms
5.0
Outstanding (14 ratings)
Westport, Fairfield County, Connecticut, United States
Details
Vrbo
Details
Details
House Westport
$480 per night
House ∙ 6 guests ∙ 3 bedrooms
5.0
Outstanding (23 ratings)
Westport, Fairfield County, Connecticut, United States
Details
Vrbo
Details
Details
House Westport
$172 per night
House ∙ 4 guests ∙ 2 bedrooms
5.0
Outstanding (7 ratings)
Westport, Fairfield County, Connecticut, United States
Details
Vrbo
Details
Details
House Westport
$700 per night
House ∙ 8 guests ∙ 4 bedrooms
5.0
Outstanding (23 ratings)
Westport, Fairfield County, Connecticut, United States
Details
Vrbo
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Recommended Rentals With Pools

House  Westport
$930 per night
House ∙ 8 guests ∙ 4 bedrooms
5.0
Outstanding (2 ratings)
Westport, Fairfield County, Connecticut, United States
Pool
Details
Vrbo
Details
Details
Villa  Westport
$1,461 per night
Villa ∙ 8 guests ∙ 4 bedrooms
Westport, Fairfield County, Connecticut, United States
Pool
Details
Vrbo
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Details
House  Westport
$1,155 per night
House ∙ 6 guests ∙ 3 bedrooms
Westport, Fairfield County, Connecticut, United States
Pool
Details
Vrbo
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Best vacation rentals with a balcony

House  Westport
$1,010 per night
House ∙ 6 guests ∙ 3 bedrooms
4.4
Very good (12 ratings)
Westport, Fairfield County, Connecticut, United States
Balcony
Details
Vrbo
Details
Details
Apartment  Westport
$192 per night
Apartment ∙ 4 guests ∙ 3 bedrooms
5.0
Outstanding (2 ratings)
Westport, Fairfield County, Connecticut, United States
Balcony
Details
Vrbo
Details
Details
House  Westport
$1,547 per night
House ∙ 8 guests ∙ 4 bedrooms
5.0
Outstanding (6 ratings)
Westport, Fairfield County, Connecticut, United States
Balcony
Details
Vrbo
Details
Details
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Vacation Homes With Terraces

House  Westport
$790 per night
House ∙ 8 guests ∙ 3 bedrooms
5.0
Outstanding (5 ratings)
Westport, Fairfield County, Connecticut, United States
Balcony/Patio
Details
Vrbo
Details
Details
House  Westport
$1,963 per night
House ∙ 11 guests ∙ 6 bedrooms
5.0
Outstanding (2 ratings)
Westport, Fairfield County, Connecticut, United States
Balcony/Patio
Details
Vrbo
Details
Details
House  Westport
$950 per night
House ∙ 10 guests ∙ 5 bedrooms
Westport, Fairfield County, Connecticut, United States
Balcony/Patio
Details
Vrbo
Details
Details
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Frequently Asked Questions

Can I find cheap vacation rentals in Westport?

Vacation rentals in Westport are priced starting at $101 per night.

Is it possible to compare multiple vacation rentals in Westport?

Currently, there are 54 vacation rentals available for you to compare and book.

Finding the perfect vacation home has never been easier. Tripping.com searches the world's top vacation rental sites to find the best properties in 190 countries worldwide. One search lets you filter, compare and sort over 10 million available vacation rentals from trusted partners including HomeAway, VRBO, TripAdvisor, Booking.com and more. When you use Tripping.com to plan your trip and book your vacation rental, you never have to wonder if you're getting the best deal.

Vacation Rentals in Westport

Save hundreds with a vacation home rental from Tripping.com and forget the hotel room. For the ultimate getaway, Westport offers 66 affordable vacation rentals with a price to match your budget and accommodation needs. Prices in Westport start at an average price of $414 a night with long-term rentals averaging $25 a month. These vacation rentals offer a range of amenities, so you’ll feel right at home. For those looking to stay in a corporate rental, 59 of Westport’s rentals offer high speed WiFi Internet so you can easily keep in touch with your company or team. Go for a swim at one of the 23 properties complete with pool or jacuzzi, or relax with a night of cable TV in any of our 55 vacation home rentals. Traveling with your dog or cat? Choose from 23 pet-friendly rentals in Westport that allow you to bring your extended family along.Tripping.com’s home rentals offer far more room and comfort than a hotel, providing a safe and spacious place for you and your pets. Many properties allow you to book directly online, so once you find that perfect vacation rental, you’ll be all set to go! Search properties from 4 vacation rental sites in Westport where the top providers in that area are HomeAway, TripAdvisor, and Booking.com. There are 58 HomeAway rentals, 4 TripAdvisor short term rentals and 2 Booking.com vacation rentals.

Popular Day Trips Near Westport

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