Westport holiday homes

We found 488 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:25 Sept - 2 Oct

Image gallery for Fairfield Beach Modern Colonial

Front of house
10 out of 10, Exceptional, (7 reviews)
Exceptional
(7 reviews)

Fairfield Beach Modern Colonial

Fairfield

8% off
Price is NZ$15,880
for 7 nights, 1 home
NZ$2,269 per night
includes taxes & fees
Fairfield Beach Modern Colonial

Find spaces that suit your style

  • 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

Why visit Westport

  • Coastal charm: Enjoy Westport's scenic beaches and seaside escapes, perfect for romantic walks and family outings.
  • Lush urban parks: Discover picturesque parks offering tranquil outdoor seating areas and scenic paths.
  • Cultural heritage: Explore engaging museums that celebrate Westport's rich history and local traditions.
  • Relaxed atmosphere: Experience a blend of leisure and business vibes with friendly locals and a laid-back pace.
  • Outdoor adventures: Embrace a mix of relaxation and adventure, from coastal strolls to nature-filled explorations.

Top attractions in and around Westport

Westport, Connecticut, offers a delightful blend of outdoor activities and cultural experiences, perfect for a romantic getaway or a family holiday. Enjoy scenic beaches, picturesque urban parks, and engaging museums that showcase the area's rich heritage. Whether you're exploring the coastline or strolling through lush green spaces, Westport caters to those seeking relaxation and adventure alike, making it an inviting destination for travellers from all walks of life.

  • The Glass House: Immerse yourself in a museum with a cultural vibe, located 14km from Westport, offering fascinating insights into art and history.
  • Southport Beach: Enjoy the beach vibe at this scenic stretch 5km from Westport, perfect for sunbathing and seaside strolls.
  • Westport Historical Society: Explore local history within Westport at this museum that captures the rich cultural heritage of the area.

Things to do recommended for couples

For a romantic getaway in Westport, explore the picturesque Compo Beach at sunset or enjoy a scenic boat tour along the Saugatuck River. Don’t miss a charming dinner at one of the local bistros, perfect for couples seeking a delightful culinary experience together.

Things to do recommended for families

Families visiting Westport can enjoy exploring the local art scene at nearby galleries and spending a day at Westport's beautiful parks and beaches, perfect for a family outing and a taste of local charm.

Things to do recommended for groups

Groups visiting Westport can enjoy the Adventure Park at Discovery Museum, an exhilarating zipline ropes course 13km away, offering an adventurous, outdoor experience perfect for group travellers looking to embrace local thrills.

*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

No matter if you're travelling with a group, as a family, or bringing your pets along, or if you're considering an extended stay, it's important to filter according to your key priorities. Here are some helpful Vrbo booking tips for you.

  • Traveling to Westport with a group: Think about how many bedrooms you'll require and any additional features you might want, like a full kitchen or outdoor area for group get-togethers. Luckily, you can easily filter for these options, and plenty more, on Vrbo.
  • Traveling to Westport with young kids: Traveling with young children can be quite a task. It's important to prioritise their comfort and safety, as well as provide suitable amenities like a private swimming pool. Additionally, it's wise to think about your closeness to family-friendly attractions.
  • Taking your pets with you to Westport: For many, a family holiday isn’t truly complete without their furry companion by their side. If that resonates with you, take a look at Vrbo properties that welcome pets. Most of these pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Westport: If you're after holiday rentals offering discounts for month-long stays, you've come to the right spot. With just a few filters, you can effortlessly discover and save on monthly bookings. You might also want to include extras like a parking space, a quality kitchen, or a private pool in your search.

Where to stay near Westport

Explore Westport, Connecticut, where a stroll along its scenic paths reveals natural features and outdoor seating areas perfect for a sunny, family-friendly and romantic escape. Enjoy the city's blend of business and leisure vibes as you discover its relaxed pace and friendly locals, making it a delightful destination for both outdoor adventures and tranquil moments by the sea.

  • Stamford: Stamford, a vibrant city located 18km from Westport, offers a fantastic blend of family-friendly attractions and city-themed adventures with an outdoor twist. Visitors can enjoy a mix of retail therapy at shopping areas, cultural indulgence at theatres, and enriching experiences at local education centres. The city's tourist precinct and modern squares provide lively hubs for exploration, making it an ideal destination for those seeking a dynamic urban escape.
  • Norwalk: Situated merely 5km from Westport, Norwalk presents an inviting urban atmosphere perfect for families and city enthusiasts alike. With its close proximity, travellers can quickly access a range of activities from engaging educational ventures to leisurely strolls around shopping areas and a challenging round at the local golf course. Attractions such as the beach and modern college university add to the charm of this coastal city.
  • Fairfield: Fairfield, located 8km from Westport, is a city that beautifully marries urban chic with a rich cultural tapestry. Designed for those who relish a city-themed experience with outdoor adventures, Fairfield offers a blend of educational opportunities, recreational areas, and golf courses. The modern college university and various beach attractions, including a family beach, provide a multifaceted experience for any traveller looking to explore the area.

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.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
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

Considering your upcoming trip? Flexibility with your travel dates can play a big role in reducing costs, as fares often fluctuate. You may also enjoy substantial savings by choosing a longer stay. To discover a Vrbo property that aligns with your budget, simply use our filters to sort by price, location, and type of holiday rental.

Vrbo Trips: Planning as easy as it gets

Vrbo’s innovative Trip Board offers you a dedicated space to start planning new adventures, pick up where you left off, or neatly organise your travel plans. You can now find properties you’ve saved or booked in your Potential, Upcoming, or Current Trips. To explore your Trip Boards, simply visit: 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)
  • H. Smith Richardson Golf Course (7.1 mi / 11.4 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)
  • E. Gaynor Brennan Golf Course (11.9 mi / 19.2 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)
  • 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)
  • South Pine Creek Beach (4.8 mi / 7.8 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 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.

More holiday ideas