Photo by Marina Timo

Westport holiday lettings

We found 498 holiday rentals — enter your dates for availability

Discover a selection of 55 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:10 Oct - 17 Oct

Why visit Westport

  • Stunning beaches: Westport boasts beautiful beaches ideal for sunbathing, swimming, and relaxing by the shore.
  • Picturesque parks: Enjoy recreational activities and scenic walks in Westport's charming urban parks.
  • Cultural experiences: Explore the town's historical sites and vibrant arts scene, catering to diverse interests.
  • Family-friendly attractions: Discover a variety of activities perfect for families, ensuring fun for all ages.
  • Unique accommodations: Choose from a range of delightful holiday rentals, from cosy cottages to stylish apartments.

Popular types of accommodation in Westport

Discover the charm of Westport with our exceptional holiday rentals, ranging from houses and cosy cottages to stylish apartments. Whether you’re seeking a peaceful retreat or a base for adventure, Westport accommodation offers something for every traveller. Explore our variety of holiday cottages and rentals, designed to provide transparency, savings, and reassurance for your perfect getaway.

  • Houses: The top choice among visitors to Westport, offering spacious and comfortable living for families or groups seeking a home-away-from-home experience.
  • Apartments: A popular option for those who prefer a self-contained space, providing convenient access to local amenities.
  • Cottages: These delightful, quaint retreats offer a charming escape for couples or small families looking for a peaceful getaway.
  • Cabins: Ideal for outdoor enthusiasts, these rustic lodgings provide a cosy haven amidst nature.
  • Condos: A practical choice for visitors, offering modern comforts and communal facilities in a vibrant setting.**

Top attractions in and around Westport

Westport, Connecticut, is an ideal destination for outdoor enthusiasts, families, and couples alike. With its stunning beaches, picturesque urban parks, and modern universities, there's plenty to explore. Visitors can enjoy a variety of activities that cater to those seeking outdoor adventures, family fun, and cultural experiences. Make the most of your time in Westport and discover its charming attractions.

  • Compo Beach: A delightful seaside escape right in Westport, Compo Beach offers a stunning shoreline, perfect for sunbathing, swimming, and picnicking. With its vibrant beach vibes, it’s an ideal spot for relaxation or a stroll along the sandy shores.
  • Fairfield University: Located 3.1km from Westport, this modern university boasts impressive architecture and a lively atmosphere, embodying city vibes. The campus is a beautiful space for a leisurely walk, featuring art installations and green areas.
  • Historic South Norwalk: Just 2.5km away, Historic South Norwalk is rich in culture, showcasing charming 19th-century architecture, boutique shops, and delightful eateries. This area invites exploration and appreciation of its vibrant history.

Things to do recommended for couples

Looking for a romantic getaway in Westport? Enjoy an evening at the Levitt Pavilion for a delightful music concert. For a touch of romance, visit Harmony Vineyards or Del Vino Vineyards, both just a short drive away, offering exquisite wines and charming atmospheres.

Things to do recommended for families

Families can enjoy a thrilling experience at the Hartford HealthCare Amphitheater, just 5.6km away, or unwind at Seaside Park, 5.0km away, for some wellness and relaxation. Don't miss the Rolnick Observatory in Westport for an entertaining family outing under the stars.

Things to do recommended for groups

In Westport, groups can enjoy a captivating performance at the Westport Country Playhouse, savour fresh produce at the vibrant Farmers Market, and indulge in shopping and entertainment at the nearby Center Seven Shopping Centre, just a short drive away, ensuring a delightful local experience.

Booking with Vrbo is simple

Are you aiming to save on your upcoming getaway? Being flexible with your travel dates can make a real difference, as prices often fluctuate. Additionally, consider booking a longer stay to enjoy considerable savings. To discover a Vrbo property that suits your budget, utilise our filters to sort by price, location, and type of holiday rental.

Where to stay near Westport

Westport, Connecticut, offers a delightful blend of outdoor activities, family-friendly attractions, and romantic spots perfect for a getaway. With easy access to central Westport, visitors can explore charming neighbourhoods that radiate warmth and friendliness. Whether enjoying picturesque parks or delving into the town's historical sites, you'll find it an ideal location for families and couples alike. Discover the unique vibes and experiences that make Westport a memorable destination.

  • Stamford: Stamford is a vibrant city located 6.8km from Westport, offering a delightful mix of family-friendly activities and urban charm. Visitors can enjoy an array of shopping options, from boutique stores to major retailers, as well as a variety of entertainment venues, including theatres and cultural centres. The city’s landmarks, such as the bustling Stamford Town Center and the scenic modern square, provide ample opportunities for exploration and relaxation, making it an ideal destination for a day trip or a leisurely afternoon.
  • Norwalk: Situated a mere 1.9km from Westport, Norwalk is a lovely city that caters to families and outdoor enthusiasts alike. The city is known for its beautiful beaches, including the popular family beach, where visitors can bask in the sun or enjoy water activities. Norwalk also boasts a rich history, with several historic sites to explore, alongside a vibrant shopping district. With educational attractions and seasonal skiing options, Norwalk offers a well-rounded experience for all ages.
  • Fairfield: Fairfield, located 3.1km from Westport, is a charming city that combines culture and outdoor enjoyment. The city features a mix of recreational areas, shopping districts, and educational institutions, including a modern college university. Visitors can relax on the sandy shores of the beach or explore the family-friendly beach area, making it a perfect spot for both relaxation and adventure. The emphasis on culture and community makes Fairfield a delightful place to visit.

Best time to go to Westport

If you're planning a trip to Westport, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs in April to May and July, while off-peak times, like January to February and October tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January31.5°F (-0.3°C)Light RainMostly SunnySlightly LowSlightly Low
February32.7°F (0.4°C)Light RainMostly SunnySlightly LowSlightly Low
March39.2°F (4.0°C)Light RainMostly SunnyAverageSlightly Low
April49.5°F (9.7°C)Light RainMostly SunnySlightly HighAverage
May59.4°F (15.2°C)Light RainMostly SunnySlightly HighAverage
June68.4°F (20.2°C)Light RainMostly SunnyAverageSlightly High
July75.4°F (24.1°C)Light RainMostly SunnySlightly HighSlightly High
August74.1°F (23.4°C)Light RainMostly SunnyAverageSlightly High
September67.6°F (19.8°C)Light RainMostly SunnyAverageAverage
October57.4°F (14.1°C)Light RainMostly SunnySlightly LowAverage
November45.9°F (7.7°C)Light RainMostly SunnyAverageAverage
December37.9°F (3.3°C)Light RainMostly SunnyAverageAverage

What do I need to keep in mind when booking a vacation in 'Westport

If you're travelling with a group, family, or pets, or if you're seeking extended stays, be sure to refine your search according to your key priorities. Here are some helpful tips for booking with Vrbo.

  • Traveling to Westport with a group: Think about how many bedrooms you require, along with features like a complete kitchen or outdoor area for group gatherings. Thankfully, you can refine your search for all of these options, and more, on Vrbo.
  • Traveling to Westport with young kids: Travelling with young children can be quite demanding. It's essential to prioritise their comfort and safety, along with suitable amenities for their age, like a private swimming pool. Additionally, it would be wise to take into account your closeness to family-friendly attractions.
  • Taking your pets with you to Westport: For many families, a holiday wouldn't feel complete without their furry companion by their side. If this resonates with you, explore Vrbo properties that welcome pets. Most of these pet-friendly accommodations offer feeding bowls and beds, ensuring that all members of the family feel completely at home.
  • Planning for a long term stay visiting Westport: If you're in search of holiday rentals with offers for stays of a month or more, you've come to the right spot. By using the appropriate filter, you can effortlessly discover and save on monthly rentals. You might also want to include features like a parking space, a well-equipped kitchen, or a private pool in your search criteria.

Vrbo Trips: Planning as easy as it gets

Vrbo's clever Trip Board offers you a dedicated area to plan new adventures, pick up from where you last stopped, or review and arrange your itinerary. You can easily access properties you've previously saved or booked under Potential, Upcoming, or Current Trips. To start using Trip Boards, simply visit: https://www.vrbo.com/en-gb/trips.

**Based on Vrbo properties bookings.

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)
  • Hand & Stone Massage and Facial Spa (11.1 mi / 17.8 km)
  • Del Vino Vineyards (15.9 mi / 25.6 km)
  • Great River Golf Club (17.1 mi / 27.5 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:

  • Old Mill Beach (1.5 mi / 2.5 km)
  • Compo Beach (2.6 mi / 4.2 km)
  • Burying Hill Beach (2.7 mi / 4.3 km)
  • Southport Beach (3.3 mi / 5.4 km)
  • Calf Pasture Beach (4.2 mi / 6.7 km)
  • Fairfield Beach (5.5 mi / 8.9 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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