Westport holiday rentals
We found 494 holiday rentals — enter your dates for availability
Holiday rentals with weekly discounts – Westport
Showing deals for:25 Dec - 1 Jan
Exceptional
(7 reviews)
Fairfield Beach Modern Colonial
Fairfield
S$10,873
for 7 nights, 1 home
S$1,553 per night
includes taxes & fees
Exceptional
(5 reviews)
2 Beautiful Homes, 1 Stunning Retreat: Pool HotTub Pizza Oven + Near Beach & NYC
Fairfield
S$27,208
for 7 nights, 1 home
S$3,887 per night
includes taxes & fees
Exceptional
(5 reviews)
Lake house cozy to relax with a family. 6 bedroom very spacious house.
Trumbull
S$12,818
for 7 nights, 1 home
S$1,831 per night
includes taxes & fees
Exceptional
(6 reviews)
Darien family home on a Cul de Sac with pond.
Darien
S$7,777
for 7 nights, 1 home
S$1,111 per night
includes taxes & fees
Wonderful
(16 reviews)
<br>❤️High-Line Harbor Flat 2 BD | Train🚊 | Harbor Point Access | 40 Minutes to NYC🗽
Stamford
S$1,821
for 7 nights, 1 apartment
S$260 per night
includes taxes & fees
Very good
(13 reviews)
❤️High-Line Harbor Pad 2 BDTrain🚊Harbor Point Access 40 Minutes to NYC
Stamford
S$1,926
for 7 nights, 1 apartment
S$275 per night
includes taxes & fees
Exceptional
(10 reviews)
The Season’s Luxe One Bedroom Apartment, Center of Stamford, Train2NYC
Stamford
S$1,248
for 7 nights, 1 apartment
S$178 per night
includes taxes & fees
Exceptional
(9 reviews)
Luxurious 3BR/2BA Modern Haven Downtown Stamford
Stamford
S$4,948
for 7 nights, 1 apartment
S$707 per night
includes taxes & fees
Find spaces that suit your style
House
Condo/Apartment
Cabin
Cottage
Villa
Chalet
Find properties near top attractions in Westport
Sherwood Island State Park
More information about Sherwood Island State Park. Opens in a new window.Find the best place to stay - Westport
Westport Gem - walk to shops, dining, town center, pet-friendly
Sleeps 4 · 2 bedrooms · 2 bathrooms
The Riverside
Sleeps 3 · 2 bedrooms · 1 bathroom
Historic Loft, Co-Work, River View
Sleeps 3 · 1 bedroom · 1 bathroom
Historic oyster shack.
Sleeps 10 · 1 bedroom · 1 bathroom
Westport: Walk to Town, Private Natural Setting, Lovely Neighborhood
Sleeps 8 · 5 bedrooms · 2 bathrooms
Boho Chic Private Home in the Heart of Westport CT
Sleeps 4 · 2 bedrooms · 1 bathroom
Peace of mindOur Book with Confidence guarantee gives you 24/7 support
More quality timeFrom booking to staying, the whole process is simple and enjoyable
All the privacy of homeEnjoy full kitchens, laundry, pools, gardens and more
More for lessMore space, more privacy, more amenities — more value
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.