Westport vacation rentals

We found 498 vacation rentals — enter your dates for availability
Discover a selection of 54 homes and other vacation rentals in Westport that are perfect for your trip. Whether you're traveling with your kids or with friends, vacation rentals have the amenities you need and want for your stay, which might include parking and a garden. You'll be sure to find a rental to meet everyone's needs, including options that are accessible or non-smoking.

Holiday rentals with weekly discounts - Westport

Showing deals for:Feb 12 - Feb 19

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

Interior
10 out of 10, Exceptional, (11 reviews)
Exceptional
(11 reviews)

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

Stamford

7% off
Price is CA $149
CA $1,392 total
Total includes taxes & fees
The Season’s Luxe One Bedroom Apartment, Center of Stamford, Train2NYC

Find spaces that suit your style

Find out more about Westport

Why visit Westport

  • Scenic Beaches: Westport boasts beautiful coastal views and pristine beaches, perfect for relaxation and outdoor fun.
  • Charming Downtown: Explore downtown Westport, filled with unique shops, cafes, and a welcoming atmosphere.
  • Cultural Experiences: Enjoy local museums and art galleries that showcase the region's rich cultural heritage.
  • Family-Friendly Activities: Westport offers a variety of activities suitable for families, ensuring fun for all ages.
  • Outdoor Adventures: Take advantage of urban parks and nature trails for hiking, biking, and enjoying the great outdoors.

Popular types of accommodation in Westport

If you’re exploring Westport for your next getaway, you’ll find a variety of popular accommodation options to suit your needs. From charming private holiday homes and cozy cottages to modern apartments for rent, there’s something for everyone. Whether you’re looking for a whole home in Westport or a comfortable apartment, you can expect a range of choices that prioritize comfort and convenience for your stay.

  • Private Holiday Homes: These spacious, fully-equipped residences offer a comfortable and private retreat for families and groups looking to enjoy Westport's charm.
  • Apartments: Ideal for couples or solo travellers, these stylish living spaces provide convenience and a local vibe in the heart of the town.
  • Cottages: Quaint and cozy, these charming dwellings are perfect for those seeking a peaceful escape surrounded by nature.
  • Cabins: Rustic and inviting, these accommodations offer a unique experience, often nestled in wooded areas, perfect for nature lovers.
  • Condos: These modern units typically feature amenities and are great for enjoying a comfortable stay with easy access to local attractions.**

Top attractions in and around Westport

Westport, Connecticut, offers a charming blend of outdoor activities and romantic scenery, making it an ideal holiday destination. Visitors can enjoy beautiful beaches, urban parks, and local museums, catering to a variety of interests including culture and family experiences. Whether you're exploring the coastline or soaking in the local arts, Westport provides a delightful escape for all types of travellers seeking adventure and relaxation.

  • Compo Beach: Enjoy the quintessential beach vibes at Compo Beach, a beautiful sandy stretch perfect for sunbathing, picnicking, and swimming. The scenic views and recreational activities make it a delightful spot for families and nature lovers alike.
  • Historic South Norwalk: Just 6km from Westport, this charming district is rich in culture and history. Explore its unique shops, galleries, and waterfront restaurants, all set against a backdrop of beautifully preserved architecture.
  • The Glass House: Located 14km away, this museum showcases modernist architecture and stunning art. Designed by Philip Johnson, the Glass House offers a unique experience with its seamless integration of nature and design.

Things to do recommended for couples

Looking for a romantic getaway in Westport? Explore the scenic beauty of Compo Beach at sunset, or take a leisurely stroll along the Saugatuck River. Don't miss a cozy dinner at one of the charming local restaurants, perfect for creating unforgettable memories together.

Things to do recommended for families

Discover the beautiful Compo Beach, perfect for sunbathing and picnics, or explore the interactive exhibits at the Westport Historical Society. Families can also enjoy a fun day at the Westport Weston Family YMCA, which offers various recreational activities for all ages.

Things to do recommended for groups

Groups visiting Westport can experience the thrill of The Adventure Park at Discovery Museum, an exciting zipline and ropes course located 13km away. Enjoy the great outdoors while challenging yourselves with fun activities that foster teamwork and adventure.

*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 planning a trip with a group, your family, or even your pets, or if you're considering a longer stay, be sure to use the appropriate filters to match your needs. Here are some helpful Vrbo booking tips to assist you.

  • Traveling to Westport with a group: Think about how many bedrooms you'll require, along with features like a fully equipped kitchen or outdoor areas for group gatherings. Thankfully, you can easily filter for all of these options and more on Vrbo.
  • Traveling to Westport with young kids: Traveling with young children can present some challenges. It's important to prioritize their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, it's wise to think about how close you are to attractions that cater to families.
  • Taking your pets with you to Westport: For many, a family getaway isn't truly satisfying without their furry companion by their side. If that resonates with you, explore Vrbo properties that welcome pets. Most of these pet-friendly accommodations offer feeding bowls and cozy beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Westport: If you're searching for vacation rentals with special offers for stays of a month or more, you've come to the perfect spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to include options 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 activities, romantic scenery, and a family-friendly atmosphere. Visitors can explore charming downtown Westport, enjoy the beautiful coastal views, and discover nearby neighborhoods that radiate warmth and friendliness. Whether you're seeking a sunny getaway or a serene escape, Westport and its surrounding areas provide the perfect backdrop for a memorable holiday experience.

  • Stamford: Located approximately 18km from Westport, Stamford is a vibrant city that offers a diverse blend of family-friendly activities and urban charm. Visitors can enjoy a bustling shopping district, catch a show at the local theatre, or explore educational venues. The city’s modern square is a popular gathering spot, ideal for leisurely strolls and socializing. Stamford's waterfront is also a highlight, providing scenic views and outdoor recreation opportunities, making it a perfect spot for families and city enthusiasts alike.
  • Norwalk: Just 5km from Westport, Norwalk is a welcoming city known for its family-oriented attractions and engaging outdoor experiences. Visitors can explore local beaches, which are perfect for a day of sun and fun, or enjoy the picturesque surroundings at the modern college university. Norwalk also features shopping areas and golf courses, catering to a variety of interests. With its mix of recreational activities and educational opportunities, Norwalk is an ideal destination for a well-rounded family outing.
  • Fairfield: Situated about 8km from Westport, Fairfield offers a delightful combination of culture, outdoor experiences, and urban appeal. The city is home to a renowned modern college university and features beautiful beaches that are perfect for family outings. Outdoor enthusiasts can take advantage of the recreational areas and golf courses available. Fairfield's vibrant community and local attractions make it a great choice for those looking to immerse themselves in both culture and nature.

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.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
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

Booking with Vrbo is a breeze

Are you hoping to save on your next adventure? Being flexible with your travel dates can make a big difference, as prices often fluctuate. Additionally, consider booking a longer stay to unlock even more savings. To discover a Vrbo property that suits your budget, take advantage of our filters to sort by price, location, and type of vacation rental. We're here to help you find the perfect getaway.

Vrbo Trips: Planning made easy

Vrbo’s Trip Board offers a user-friendly platform where you can effortlessly create new trips, continue from where you last left off, or manage your travel plans. You’ll find your saved or booked properties neatly organized into categories: Potential, Upcoming, or Current Trips. To begin exploring Trip Boards, simply visit: https://www.vrbo.com/en-ca/trips.

**Based on Vrbo properties bookings.

The waterfront setting of Westport is ready to explore

Take a vacation to Westport and enjoy the area's opera, entertainment and theater scene. This city is well-known for its football games and restaurants. With a vacation 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 searching for attractions to visit while you're in town? Although it can be tempting to stay in your comfortable vacation rental, you'll want to experience everything that Westport has to offer. Here are some of the major attractions to see, all within 30 miles (48.2 km) of the city center:

  • 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 an outdoor enthusiast or just want to appreciate the scenery, Westport is a great place to get outside. Here are a few of the area's most stunning natural features, all within 30 miles (48.2 km) of the city center:

  • Compo Beach (2.6 mi / 4.2 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)
  • Lake Mohegan (7.1 mi / 11.4 km)

Transportation 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 center. If you can't find a flight that's convenient for your trip, you can also fly into Danbury, CT (DXR-Danbury Municipal), which is 17.3 mi (27.8 km) away.

If you prefer train travel, 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 vacation rental?
When considering a vacation 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.
How much does it cost to rent a vacation home in Westport?
Prices for vacation rentals 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. Vrbo offers something for every taste and budget, from affordable rentals in Westport to more spacious homes.
Are there any discounts for Westport vacation house rentals?
You can find great discounts on house rentals in Westport on Vrbo, 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.
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 vacation rental accomodation in Westport?
In Westport, vacation houses are the most popular type of vacation 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 vacation 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 vacation home with a pool or hot tub in Westport?
In Westport, Connecticut, there are several vacation 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.
Can I find long-stay vacation rentals in Westport?
A long-stay vacation rental 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 travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
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 vacation rentals in Westport?
In Westport, Connecticut, there are numerous options for remote work vacation 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 Vrbo.
Are there any Westport vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals 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 on Vrbo 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.
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 vacation rental?
The peak season for vacation 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 vacation 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.
How early should I book a Westport vacation rental?
Book your Westport vacation rental 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 Vrbo booking and occupancy data for 2024 stays.
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.
Can I change or cancel my Westport home rental booking on Vrbo?
To find Westport vacation rentals with free cancellation, just use Vrbo'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". Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo 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, Vrbo 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 Vrbo handle the heavy lifting to help you thrive.

Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Westport vacation rental prices shown on Vrbo?
Vrbo 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.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, 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.

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.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way.

Vrbo 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.
Can I plan a group trip on Vrbo?
Vrbo'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 favorites, and build the perfect itinerary together.

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