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Featured Vacation Homes in Westport

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Newly Renovated Summer Home in Westport CT Private Pool & Spa, Near Beach & Town

Newly Renovated Summer Home in Westport CT Private Pool & Spa, Near Beach & Town

Westport, CT
This vacation home features an outdoor pool and a fitness center. Enjoy the spa tub and conveniences like a garden and barbecue grills.
 
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1/2 Block to Compo Beach on Long Island Sound!

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

Westport, CT
An outdoor tennis court is featured at this vacation home, along with a garden and barbecue grills.
 
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Dramatic Waterfront Family Home Directly on the Saugatuck River in Westport, CT

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

Westport, CT
This vacation home features barbecue grills.
 
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Westport Summer Estate

Westport Summer Estate

Westport, CT
A fitness center is featured at this vacation home, along with concierge services and barbecue grills.
 
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Westport Family Home 3 Miles To Beach

Westport Family Home 3 Miles To Beach

Westport, CT
A fitness center is featured at this vacation home, along with limo/town car service.
 
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1+ Bdrm Antique Home In Westport, CT

1+ Bdrm Antique Home In Westport, CT

Westport, CT
Situated in Westport, this vacation home is 0.7 mi (1.1 km) from Old Mill Beach and 2.8 mi (4.6 km) from Norwalk Maritime Aquarium. Norwalk City Hall and Levitt Pavilion are also within 3 mi (5 km). Westport Station is 8 minutes by foot.
 
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Pool & Beach Vacation in Westport, Connecticut

Pool & Beach Vacation in Westport, Connecticut

Westport, CT
An outdoor pool is available at this vacation home.
 
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European Style Country Chic With Pool & Privacy!

European Style Country Chic With Pool & Privacy!

Westport, CT
A garden is available at this vacation home.
 
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Amazing Westport Beach House Just One Block From Compo Beach

Amazing Westport Beach House Just One Block From Compo Beach

Westport, CT
Situated on the waterfront, this vacation home is 0.4 mi (0.6 km) from Compo Beach and within 3 mi (5 km) of Old Mill Beach and Levitt Pavilion. Westport Country Playhouse and Westport Historical Society are also within 3 mi (5 km). Westport Station is 29 minutes by foot.
 
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Walk-to-town Gem! Charming Renovated Colonial in Sought After Neighborhood

Walk-to-town Gem! Charming Renovated Colonial in Sought After Neighborhood

Westport, CT
A garden is available at this vacation home.
 
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Vacation Ready: Beautiful House With Heated Pool

Vacation Ready: Beautiful House With Heated Pool

Westport, CT
This vacation home features an outdoor pool and a fitness center. Barbecue grills are provided for your convenience.
 
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Amazing New Construction Home With Large Yard. 5 Minutes to Everything!

Amazing New Construction Home With Large Yard. 5 Minutes to Everything!

Westport, CT
A garden is available at this vacation home.
 
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Westport Vacation Home Rentals

What kind of vacation do you want in Westport? The answer to that question will help you choose the right lodging for your stay. The wise wanderer knows that a vacation home is an essential part of the traveling experience. It’s more than just a place to crash at night—it’s where you wake up in the morning, where you lounge when you’re not exploring, and it’s the starting point for all your adventures. No matter what type of vacation homes strike your fancy, Travelocity has something in Westport that will speak to you.

Do you want a fully equipped kitchen so you can exercise your culinary mastery and impress your travel buddies? How about a romantic terrace for your anniversary trip? Have you always wished to fall asleep to the sound of waves crashing on the shore? One of our vacation home rentals is bound to add that extra magic to your trip. In fact, we’ve got plenty of options lined up just for you in Westport, including luxury vacation home rentals. On a budget? We can work with your funds and still give you a great place to sleep at night.

Take a look at what we have on offer. You’ll find rental houses close to the big tourist draws, as well as rentals that keep you away from the crowd. Consider vacation homes a little off the beaten path where you can live like a local and discover hidden gems that never make it to the tourist sites. Book through Travelocity and start your getaway today.


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Newly Renovated Summer Home in Westport CT Private Pool & Spa, Near Beach & Town

Newly Renovated Summer Home in Westport CT Private Pool & Spa, Near Beach & Town

Westport, CT
Situated in a rural location, this historic vacation home is 2.9 mi (4.7 km) from Earthplace Museum and 2.9 mi (4.7 km) from Westport Historical Society. Levitt Pavilion and Westport Country Playhouse are also within 6 mi (10 km).
 
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The Westport Inn

The Westport Inn

2.5 out of 5.0 1595 Post Road East, Westport, CT
Situated by the ocean, this motel is within 3 mi (5 km) of Southport Beach, Burying Hill Beach, and Sherwood Island State Park. Westport Country Playhouse and Country Club of Fairfield are also within 3 mi (5 km). Southport Station is 24 minutes by foot.
 
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Charming Historic Cottage Perfectly Kept in Westport, CT Close to New York City

Charming Historic Cottage Perfectly Kept in Westport, CT Close to New York City

Westport, CT
Situated by the ocean, this historic cottage is within 3 mi (5 km) of Earthplace Museum, Westport Historical Society, and Levitt Pavilion. Westport Country Playhouse and Wilton Historical Society are also within 3 mi (5 km).
 
*Price based on the lowest price found within past 24 hours and based upon one night stay for two adults over the next thirty days. Prices and availability subject to change. Additional terms may apply.