Westport holiday rentals

We found 499 holiday rentals — enter your dates for availability
Discover a selection of 54 homes and other holiday rentals in Westport that are perfect for your trip. Whether you’re travelling with friends, family or just with your pet, holiday rentals have the best amenities for spending time at your holiday home, which might include parking and a washer and dryer. You'll be sure to find a property to rent for everyone's needs, including options that are accessible or non-smoking.

Holiday rentals with weekly discounts – Westport

Showing deals for:22 Jan - 29 Jan

Property grounds
Outdoor dining
Pool
Exterior
Exceptional
(8 reviews)

Updated Farmhouse Retreat

Wilton

8% off
S$12,548
for 7 nights, 1 home
S$1,793 per night
includes taxes & fees
Updated Farmhouse Retreat
Room
Living area
Pool
Terrace/patio
Exceptional
(5 reviews)

2 Beautiful Homes, 1 Stunning Retreat: Pool HotTub Pizza Oven + Near Beach & NYC

Fairfield

8% off
S$27,874
for 7 nights, 1 home
S$3,982 per night
includes taxes & fees
2 Beautiful Homes, 1 Stunning Retreat: Pool HotTub Pizza Oven + Near Beach & NYC
Kitchen
View of back of house
Front of house
Stairs leading to third floor
Exceptional
(7 reviews)

Fairfield Beach Modern Colonial

Fairfield

8% off
S$11,187
for 7 nights, 1 home
S$1,598 per night
includes taxes & fees
Fairfield Beach Modern Colonial
Dining
Terrace/patio
Pool
Interior
Exceptional
(5 reviews)

Lake house cozy to relax with a family. 6 bedroom very spacious house.

Trumbull

8% off
S$13,762
for 7 nights, 1 home
S$1,966 per night
includes taxes & fees
Lake house cozy to relax with a family. 6 bedroom very spacious house.
Exterior
Private kitchen
Interior
Room
Exceptional
(7 reviews)

Darien family home on a Cul de Sac with pond.

Darien

8% off
S$8,258
for 7 nights, 1 home
S$1,180 per night
includes taxes & fees
Darien family home on a Cul de Sac with pond.
Dining
Living area
Private kitchen
Exterior
Exceptional
(16 reviews)

Historic Designer City Getaway

Easton

8% off
S$9,487
for 7 nights, 1 home
S$1,355 per night
includes taxes & fees
Historic Designer City Getaway
Bedroom 1 (largest).Queen Bed, Smart TV, Dresser Desk with Ergonomic Chair.
Well stocked newly renovated kitchen. Prepare quick breakfast or a holiday meal.
Exterior
Dining room seats 6 and expands for 8 with leaf.
Exceptional
(17 reviews)

Quiet suburban home close to Fairfield beaches and universities

Fairfield

7% off
S$2,868
for 7 nights, 1 home
S$410 per night
includes taxes & fees
Quiet suburban home close to Fairfield beaches and universities
Exterior
Property grounds
Interior
Interior
Exceptional
(105 reviews)

Westport "Gold Coast" across from Southport beach

Southport

8% off
S$2,721
for 7 nights, 1 cottage
S$389 per night
includes taxes & fees
Westport "Gold Coast" across from Southport beach
Outdoor dining
Exterior
Living Room
Kitchen
Exceptional
(21 reviews)

Entire House on Scenic Estate with Private Pond in Exclusive Neighborhood

Norwalk

11% off
S$3,055
for 7 nights, 1 home
S$436 per night
includes taxes & fees
Entire House on Scenic Estate with Private Pond in Exclusive Neighborhood
Dining
Living area
Private kitchen
Living area
Very good
(13 reviews)

❤️High-Line Harbor Pad 2 BDTrain🚊Harbor Point Access 40 Minutes to NYC

Stamford

7% off
S$1,567
for 7 nights, 1 apartment
S$224 per night
includes taxes & fees
❤️High-Line Harbor Pad 2 BDTrain🚊Harbor Point Access 40 Minutes to NYC
Interior
Interior
Room
Interior
Exceptional
(11 reviews)

The Season’s Luxe One Bedroom Apartment, Center of Stamford, Train2NYC

Stamford

5% off
S$1,325
for 7 nights, 1 apartment
S$189 per night
includes taxes & fees
The Season’s Luxe One Bedroom Apartment, Center of Stamford, Train2NYC
Room
Interior
Private kitchen
Interior
Exceptional
(9 reviews)

Luxurious 3BR/2BA Modern Haven Downtown Stamford

Stamford

8% off
S$4,438
for 7 nights, 1 apartment
S$634 per night
includes taxes & fees
Luxurious 3BR/2BA Modern Haven Downtown Stamford
  • Peace of mind

    Our Book with Confidence guarantee gives you 24/7 support
  • More quality time

    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more
  • More for less

    More space, more privacy, more amenities — more value

The waterfront setting of Westport is ready to explore

Take a holiday to Westport and enjoy the area's opera, entertainment and theatre scene. This city is well-known for its football games and restaurants. With a holiday rental, you get a home away from home – many rentals offer full kitchens and outdoor grills for some home cooking.

Activities and attractions in Westport

Are you looking for top things to see and do during your stay? Venture out of your cosy holiday rental and experience everything that makes Westport a one-of-a-kind holiday spot. Here are some of the most popular attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • Norwalk Maritime Aquarium (4.2 mi / 6.7 km)
  • Chelsea Piers (10.2 mi / 16.4 km)
  • Beardsley Zoo (10.4 mi / 16.7 km)
  • Del Vino Vineyards (15.9 mi / 25.6 km)
  • Country Club of Fairfield (4.5 mi / 7.2 km)
  • Fairchild Wheeler Golf Course (7.7 mi / 12.4 km)

Exploring the natural features in Westport

Whether you're looking for adventure or just want to spend some time taking in the scenery, Westport is a great place to get outside. Here are a few of the area's most stunning features, all within 30 miles (48.2 km) of the city centre:

  • Compo Beach (2.6 mi / 4.2 km)
  • Fairfield Beach (5.5 mi / 8.9 km)
  • Penfield Beach (6.1 mi / 9.8 km)
  • Jennings Beach (6.3 mi / 10.1 km)
  • Lucius Pond Ordway / Devil's Den Preserve (6.9 mi / 11.1 km)
  • Lake Mohegan (7.1 mi / 11.4 km)

Transport options to and around Westport

The nearest airport is in Bridgeport, CT (BDR-Igor I. Sikorsky Memorial), located 11.9 mi (19.1 km) from the city centre. If you can't find a flight that works for your travel itinerary, you could book a flight to Danbury, CT (DXR-Danbury Municipal), which is 17.3 mi (27.8 km) away.

If you're travelling by train, make your way to Westport Station or Green's Farms Station to see more of the city.

Frequently asked questions

What is the most popular type of holiday rental accommodation in Westport?
The most desirable types of holiday rentals in Westport are houses. After something a little different? Vrbo has a variety of options to match our guests' needs, so you'll see holiday homes in lots of shapes and sizes. The ideal home away from home is waiting for you — snap up yours today.
How much does it cost to rent a holiday rental in Westport?
Property type, length of stay and time of year are some factors that can influence the price of a holiday home. Simply add your travel dates to find your perfect match. From cosy chalets to sprawling villas, all Vrbo holiday rentals provide incredible value.
How much does it cost to rent a beach house in Westport?
Prices for beach houses in Westport differ depending on the style and size of the property and time of year you're travelling. Simply enter your travel dates into Vrbo and the number of guests to view your options and prices. From there you can use our filters to refine your search by ratings, amenities and more.
Are there pet-friendly holiday rentals in Westport?
Pack a suitcase for your pooch because Westport has 48 holiday rentals that put out the welcome mat to pets. Let your furriest pal enjoy fun with the family at one of our pet-friendly holiday rentals on Vrbo. Simply enter your travel dates then check our "Pets allowed" filter box.
Can I rent a house with a pool in Westport?
Mark the "pool" box in our filter tool and you can choose from 20 houses with private pools in Westport on Vrbo. Lazy soak or ball games and races? How you spend your leisure time is up to you when your holiday home comes with its own swimming pool.
What are popular rental amenities in Westport?
When it comes to rental amenities that guests prefer in Westport, an electric car charging station, a nearby waterfront and a sauna rank the highest. With Vrbo holiday rentals, there are choices to suit your taste and style, whether you're planning to get away with family members, friends or even pets.
Are there large group holiday rentals in Westport?
Westport has 11 holiday rentals that can fit 10 or more people. These stays come with plenty of space to share good times with loved ones.
Are there holiday rentals in Westport that welcome kids?
Westport has 47 family-friendly holiday rentals to choose from. And booking a stay that welcomes kiddos is a breeze with Vrbo's "Properties good for families" filter. As well as having the whole place to yourselves, you'll enjoy access to amenities and perks such as living rooms, kitchens and pools.
What are the top attractions for families in Westport?
There are plenty of awesome things to do and see with the family in Westport, such as:
  • Compo Beach
  • Norwalk Maritime Aquarium
  • Jennings Beach
Are there one-bedroom holiday rentals in Westport?
Yes, you can take your pick from five one-bedroom rentals in Westport. Whether you're looking for a cosy cottage or a fancy condo, Vrbo's one-bedroom properties are perfect if you don't require a huge amount of space. One of the major perks of having your own digs? You won't ever have to share your adventure with strangers.
Can I find two-bedroom holiday rentals in Westport?
Take off with your loved ones and relax in total privacy and comfort in one of the three two-bedroom holiday properties Westport has to offer.
Are there holiday rentals with WiFi in Westport?
Westport has 15 holiday rentals with WiFi, so you can stay connected while you're on holiday. Simply check the "WiFi" box in our search filter for a list of properties with this feature. From streaming movies with your family to catching up on social media, these Vrbo homes will keep you online.
How can I find holiday rentals with air conditioning in Westport?
Pick your travel dates and then use our filters to view holiday rentals with air conditioning in Westport on Vrbo. With 46 air-conditioned properties on offer here, you can look forward to a comfortable and cool stay.
How old do you have to be to rent a holiday rental in Westport?
The minimum age is typically 16, 18 or 21. It can differ between properties on Vrbo, so check the rules of your chosen Westport stay before booking your escape.
How long can I rent a holiday rental in Westport for?
The length of time you can book a holiday rental in Westport is up to the property. Just enter your selected travel dates to look at a list of options offering extended stays. With many creature comforts such as kitchens and air conditioning, as well as some offering discounted weekly or monthly prices, you're sure to get someplace just right to call your home away from home in Westport.

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