Photo by Marina Timo

Westport holiday homes

We found 493 holiday rentals — enter your dates for availability

Discover a selection of 58 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:26 Dec - 2 Jan
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Why visit Westport

  • Stunning beaches: Relax on Westport's beautiful sandy beaches, perfect for swimming and sunbathing.
  • Charming downtown: Discover a vibrant downtown filled with unique shops and delightful eateries.
  • Outdoor adventures: Engage in various outdoor activities at urban parks and nature reserves nearby.
  • Cultural experiences: Explore local history and art at nearby universities and cultural sites.
  • Family-friendly activities: Enjoy a range of activities suitable for all ages, ensuring fun for the whole family.

Top attractions in and around Westport

Westport, Connecticut, offers a delightful blend of outdoor adventures, family-friendly activities, and romantic getaways. Visitors can explore beautiful beaches, urban parks, and modern universities, making it a great spot for cultural experiences. Whether you're wandering through the charming town of Westport or enjoying the surrounding natural beauty, there's plenty to see and do for everyone, ensuring a memorable holiday experience.

  • Southport Beach: A stunning beach located 4.8km from Westport, Southport Beach offers a relaxed atmosphere with beautiful sand and gentle waves, perfect for sunbathing and picnicking.
  • Westport Historical Society: Situated within Westport, this history museum showcases the rich cultural heritage of the area through engaging exhibits and local artifacts, immersing visitors in the past.
  • The Glass House: Located 14.5km away, this unique museum features modern architecture and art, blending seamlessly with its natural surroundings, providing an inspiring cultural experience.

Things to do recommended for couples

For a romantic getaway in Westport, enjoy live music at Levitt Pavilion, where the atmosphere buzzes with entertainment. Venture to Del Vino Vineyards, 25.7km away, for a charming wine-tasting experience, or explore Harmony Vineyards, 30.6km away, both offering beautiful settings and a touch of romance.

Things to do recommended for families

Families can unwind at Seaside Park, only 12.9km from Westport, soaking in its relaxing atmosphere. For sports enthusiasts, the Hartford HealthCare Amphitheater, 14.5km away, offers vibrant events. Closer to home, the Rolnick Observatory provides entertaining family experiences in astronomy.

Things to do recommended for groups

Experience the local charm at the Westport Farmers Market, soak up culture at the Westport Country Playhouse, or enjoy a shopping spree at The SoNo Collection, just 6.4km away. Each spot offers vibrant vibes perfect for group fun.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

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

If you're travelling with a group, family, pets, or planning an extended stay, be sure to refine your search based on what matters most to you. Here are some helpful Vrbo booking tips to consider.

  • Traveling to Westport with a group: Think about how many bedrooms you'll require, along with features like a full kitchen or outdoor areas for group get-togethers. Luckily, you can easily filter for all these options and more on Vrbo.
  • Traveling to Westport with young kids: When travelling with young kids, it’s important to prioritise their comfort and safety, along with ensuring there are suitable amenities like a private swimming pool. Additionally, it’s wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Westport: For many, a family holiday isn’t quite right without their furry companion. If this resonates with you, explore Vrbo properties that welcome pets. Many of these pet-friendly options come equipped with feeding bowls and beds, ensuring that everyone feels at home.
  • Planning for a long term stay visiting Westport: If you're in search of holiday rentals with special offers for stays of a month or more, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on long-term rentals. Don’t forget to include features like a parking space, a well-equipped kitchen, or a private pool in your search as well.

Where to stay near Westport

Westport, Connecticut, offers a delightful mix of outdoor adventures and family-friendly activities. Explore the vibrant downtown area, where charming shops and eateries await. Relax on the sandy beaches or delve into the rich history of nearby regions. Whether you're seeking romance or a friendly atmosphere, Westport has it all, making it the perfect destination for your vacation. Enjoy a memorable stay with plenty of accommodation options to suit every need.

  • Stamford: Stamford is a vibrant city located 17.7km from Westport, offering a dynamic blend of urban and outdoor experiences. Known for its family-friendly atmosphere, Stamford features a lively shopping area and a variety of theatres that cater to culture enthusiasts. Visitors can explore the popular tourist precinct and Modern Square, where you’ll find an array of dining options and entertainment venues. Whether you're strolling through its bustling streets or enjoying the scenic vistas along the waterfront, Stamford promises a delightful day out for all ages.
  • Norwalk: Situated just 4.8km from Westport, Norwalk is a charming city that’s perfect for families and outdoor lovers alike. This area is renowned for its picturesque beaches, including the popular family beach, where you can soak up the sun and enjoy water activities. Norwalk also hosts educational attractions and a variety of shopping options that make it an ideal spot for a leisurely outing. History buffs will appreciate the numerous historic sites scattered throughout the city, providing a rich backdrop to your exploration.
  • Bridgeport: Located 14.5km away from Westport, Bridgeport is a bustling city that offers a wealth of activities for families and adventurers. With its lively recreational areas and shopping venues, there's something for everyone to enjoy. The city's attractions include beautiful beaches and a family beach that are perfect for relaxation and play. Sports enthusiasts can catch a game at the local stadium, adding to the city's vibrant atmosphere. Overall, Bridgeport is a fantastic destination for those looking to combine outdoor fun with urban excitement.

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.

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

Booking with Vrbo is a breeze

Looking to save on your next holiday? Consider being flexible with your travel dates, as prices can fluctuate. Plus, booking a longer stay can often lead to significant savings. To discover the ideal Vrbo property that fits your budget, take advantage of our filters to search by price, location, and type of holiday rental.

Vrbo Trips: Planning made easy

Vrbo’s Trip Board offers a handy space for you to plan new adventures, resume your trip planning, or keep track of your arrangements. You’ll easily find any properties you’ve saved or booked, sorted into categories like Potential, Upcoming, or Current Trips. To get started with Trip Boards, head over to: https://www.bookabach.co.nz/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)
  • E. Gaynor Brennan Golf Course (11.9 mi / 19.2 km)
  • Stanwich Club (14 mi / 22.5 km)
  • Del Vino Vineyards (15.9 mi / 25.6 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)
  • 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)
  • Penfield Beach (6.1 mi / 9.8 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 home accommodation in Westport?
The most desirable types of holiday homes in Westport are houses. After something a little different? Bookabach 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 home 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 Bookabach holiday homes 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 Bookabach 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 homes in Westport?
Pack a suitcase for your pooch because Westport has 48 holiday homes that put out the welcome mat to pets. Let your furriest pal enjoy fun with the family at one of our pet-friendly holiday homes on Bookabach. 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 Bookabach. 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 home amenities in Westport?
When it comes to home amenities that guests prefer in Westport, an electric car charging station, a nearby waterfront and a sauna rank the highest. With Bookabach holiday homes, 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 homes in Westport?
Westport has 11 holiday homes that can fit 10 or more people. These stays come with plenty of space to share good times with loved ones.
Are there holiday homes in Westport that welcome kids?
Westport has 47 family-friendly holiday homes to choose from. And booking a stay that welcomes kiddos is a breeze with Bookabach'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 homes in Westport?
Yes, you can take your pick from five one-bedroom homes in Westport. Whether you're looking for a cosy cottage or a fancy condo, Bookabach'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 homes 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 homes with WiFi in Westport?
Westport has 15 holiday homes 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 Bookabach homes will keep you online.
How can I find holiday homes with air conditioning in Westport?
Pick your travel dates and then use our filters to view holiday homes with air conditioning in Westport on Bookabach. 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 home in Westport?
The minimum age is typically 16, 18 or 21. It can differ between properties on Bookabach, so check the rules of your chosen Westport stay before booking your escape.
How long can I rent a holiday home in Westport for?
The length of time you can book a holiday home 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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