Westport holiday homes

We found 498 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 Dec - 1 Jan

Kitchen
View of back of house
Living room
Stairs leading to third floor
Exceptional
(7 reviews)

Fairfield Beach Modern Colonial

Fairfield

8% off
NZ$15,244
for 7 nights, 1 home
NZ$2,178 per night
includes taxes & fees
Fairfield Beach Modern Colonial
Interior
Terrace/patio
Property grounds
Pool
Exceptional
(5 reviews)

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

Trumbull

8% off
NZ$17,828
for 7 nights, 1 home
NZ$2,547 per night
includes taxes & fees
Lake house cozy to relax with a family. 6 bedroom very spacious house.
Living area
Living area
Pool
Room
Exceptional
(5 reviews)

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

Fairfield

8% off
NZ$37,592
for 7 nights, 1 home
NZ$5,370 per night
includes taxes & fees
2 Beautiful Homes, 1 Stunning Retreat: Pool HotTub Pizza Oven + Near Beach & NYC
Interior
Private kitchen
Room
Dining
Exceptional
(6 reviews)

Darien family home on a Cul de Sac with pond.

Darien

8% off
NZ$11,167
for 7 nights, 1 home
NZ$1,595 per night
includes taxes & fees
Darien family home on a Cul de Sac with pond.
Interior
Marina
Outdoor dining
Exterior
Wonderful
(16 reviews)

<br>❤️High-Line Harbor Flat 2 BD | Train🚊 | Harbor Point Access | 40 Minutes to NYC🗽

Stamford

7% off
NZ$2,580
for 7 nights, 1 apartment
NZ$369 per night
includes taxes & fees
<br>❤️High-Line Harbor Flat 2 BD | Train🚊 | Harbor Point Access | 40 Minutes to NYC🗽
Private kitchen
Living area
Room
Living area
Very good
(13 reviews)

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

Stamford

7% off
NZ$2,735
for 7 nights, 1 apartment
NZ$391 per night
includes taxes & fees
❤️High-Line Harbor Pad 2 BDTrain🚊Harbor Point Access 40 Minutes to NYC
Private kitchen
Interior
Interior
Room
Exceptional
(10 reviews)

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

Stamford

5% off
NZ$1,776
for 7 nights, 1 apartment
NZ$254 per night
includes taxes & fees
The Season’s Luxe One Bedroom Apartment, Center of Stamford, Train2NYC

  • 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)
  • 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)
  • 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)
  • Jennings Beach (6.3 mi / 10.1 km)
  • Lucius Pond Ordway / Devil's Den Preserve (6.9 mi / 11.1 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 best area to stay in Westport when booking a holiday rental?
When considering a holiday rental in Westport, Connecticut, the charming neighbourhood of Saugatuck is often regarded as an excellent choice. This vibrant area is known for its picturesque waterfront, with the Saugatuck River weaving through, offering a delightful backdrop for leisurely strolls. Visitors can enjoy the local boutique shops, cosy cafes, and a selection of restaurants that cater to diverse tastes.Another appealing neighbourhood is the Old Hill area, characterised by its serene residential atmosphere and lush, green spaces. This area is particularly close to the Westport Country Playhouse, a renowned venue for live performances, and the scenic Compo Beach, which provides a superb spot for sunbathing, swimming, and enjoying beautiful sunsets.
Where are the best areas for renting a beach house in Westport?
For renting a beach house in Westport, Connecticut, the area around Compo Beach is highly desirable. This picturesque beach features beautiful sandy shores and scenic views of Long Island Sound, making it an ideal spot for beach house rentals. Properties here typically include amenities such as spacious outdoor decks, private beach access, and modern kitchens, great for family gatherings or entertaining guests.Additionally, the Saugatuck area, with its charming waterfront and proximity to local restaurants and shops, offers a variety of rental options. Many houses in this neighbourhood come with features like outdoor showers, patio spaces with grills, and easy access to boating and water sports. The Saugatuck River adds to the appeal, offering opportunities for kayaking and paddleboarding right from your doorstep.Furthermore, the nearby Longshore Club Park provides a lovely setting for outdoor activities, including picnicking and walking trails, enhancing the beachside experience. Rentals in Westport often reflect a blend of comfort and convenience, allowing travellers to enjoy both the beach and the vibrant local culture.
What is the most popular type of holiday rental accomodation in Westport?
In Westport, holiday houses are the most popular type of holiday rental, with around 152 available throughout the area. These properties are typically spacious and are often situated in peaceful neighbourhoods, making them ideal for families or groups seeking a relaxing getaway. Most holiday houses come equipped with multiple bedrooms, full kitchens, and outdoor spaces such as gardens or patios, superb for enjoying the lovely Connecticut weather. Additionally, there are about 20 apartments and 16 cottages available, providing more compact options for solo travellers or couples.
Are there any family house rentals in Westport?
In Westport, Connecticut, there is a solid selection of family-friendly house rentals, with around 32 options available. This charming coastal town offers a variety of properties that cater to families, particularly in neighbourhoods like Saugatuck and Compo Beach. Many of these homes boast spacious living areas, fully equipped kitchens for preparing family meals, and outdoor spaces superb for kids to play and explore.Visitors can expect amenities such as Wi-Fi, air conditioning, and laundry facilities, ensuring a comfortable stay. The proximity to local attractions, including the beach and parks, provides ample opportunities for outdoor activities and family outings. Westport's vibrant community features beautiful waterfronts, picturesque walking trails, and a rich arts scene, making it an excellent destination for families seeking both relaxation and adventure.
Can I rent a holiday home with a pool or hot tub in Westport?
In Westport, Connecticut, there are several holiday homes available for rent that feature pools or hot tubs, with around 14 options to choose from. This picturesque coastal town offers a charming blend of seaside beauty and suburban tranquillity, making it an excellent choice for a relaxing getaway.Travellers can expect amenities such as private swimming pools, inviting hot tubs, spacious outdoor patios for sunbathing or dining al fresco, and fully equipped kitchens that cater to all your culinary needs. Many properties are also designed with families in mind, featuring large living areas and multiple bedrooms to accommodate groups comfortably.Westport's proximity to the beach adds to the allure, and visitors can enjoy nearby parks and waterfront activities.
Are there pet-friendly house rentals in Westport?
In Westport, there are several pet-friendly house rentals available, offering a range of amenities that cater to both travellers and their furry companions. Many of these properties feature spacious layouts with modern kitchens, outdoor spaces such as private gardens or decks, and comfortable living areas ideal for relaxation after a day of exploring.The neighbourhood provides easy access to local parks, which are superb for walking pets and enjoying the outdoors. Notable spots include Winslow Park, where you can find walking trails and picnic areas, and the scenic Compo Beach, which is also welcoming to pets during certain hours.
Are there any remote work holiday rentals in Westport?
In Westport, Connecticut, there are numerous options for remote work holiday rentals, with around 144 properties available. These rentals cater well to those needing a workspace, featuring amenities such as dedicated desks, ergonomic chairs, and reliable Wi-Fi for seamless connectivity. Many properties also offer free internet access, ensuring that you can stay productive during your stay.The charming town of Westport is known for its scenic coastal views, local parks, and vibrant arts scene, providing a pleasant backdrop for both work and leisure. After hours, you can explore the nearby beaches, enjoy the waterfront dining, or visit the local shops and galleries. To help narrow your search, insert your dates and apply the "WiFi" filter on Bookabach.
What are popular rental amenities in Westport?
In Westport, popular rental amenities include kitchens that allow for convenient meal preparation, fireplaces providing a cosy atmosphere, and deck or patio areas superb for enjoying the outdoors. Many properties also feature blenders and coffee/tea makers, suiting those who appreciate a morning brew or want to whip up smoothies.
When is the best time to visit Westport for a holiday rental?
The peak season for holiday rentals in Westport typically spans from May to July, with July being the most popular month for visitors. This vibrant period draws families and beachgoers alike, eager to enjoy the sun-soaked beaches and the charming coastal atmosphere. The warm temperatures, often reaching the mid to high 20s Celsius, create great conditions for outdoor activities, from sunbathing to kayaking in the Long Island Sound.During these months, Westport comes alive with various events, farmers' markets, and cultural activities, making it an ideal time for those seeking a lively holiday experience filled with local flavour. You'll also find that the town's picturesque parks and scenic waterfront are great for leisurely strolls or picnics.If you're looking for a more budget-friendly option, consider visiting in October. This month offers a quieter experience, allowing you to appreciate the stunning autumn foliage and the serenity of Westport's natural beauty without the summer crowds. The crisp air can be refreshing, great for scenic walks along the coast or exploring the local shops and eateries.
What are the top attractions in Westport?
In Westport, visitors can enjoy a blend of natural beauty and cultural attractions. The town's beautiful beaches, such as Compo Beach, offer stunning views of the Long Island Sound and are superb for sunbathing and picnicking. Nearby, the Westport Country Playhouse presents a range of theatrical performances, making it a cultural highlight in the area.For those interested in art, the Westport Arts Centre features exhibitions and events that showcase local talent. Additionally, the picturesque Saugatuck River runs through the town, providing opportunities for kayaking and scenic walks along the riverfront.
Are all fees included in the Westport holiday homes prices shown on Bookabach?
Bookabach provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
Are there any Westport holiday homes with parking?
Bookabach offers a wide selection of holiday homes in Westport with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Are there any discounts for Westport holiday homes?
You can find great discounts on holiday homes in Westport on Bookabach, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for last-minute bookings, and early-bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Can I change or cancel my Westport holiday home booking on Bookabach?
To find Westport holiday rentals with free cancellation, just use Bookabach's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Whether you're adjusting your plans or looking for flexible payment options, Bookabach makes it easy to book with confidence.
Can I find long-stay holiday homes in Westport?
A long-stay holiday home in Westport is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Bookabach?
Bookabach's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favourites, and build the perfect itinerary together.
How early should I book a Westport holiday home?
Book your Westport holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Bookabach booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Westport?
Prices for holiday homes in Westport vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Bookabach offers something for every taste and budget, from affordable homes in Westport to more spacious homes.
What can I expect from Bookabach customer service and Bookabach Care™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, Bookabach Care™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Bookabach customer service is available 24/7 to support you every step of the way. Bookabach also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is Bookabach Care™ and how does it work?
Bookabach's mission is to help guests relax, reconnect, and enjoy precious time together. With Bookabach Care™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
Why should I join Bookabach as a host?
Joining Bookabach as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Bookabach makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Bookabach handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

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