Photo by Marina Timo

Westport vacation rentals

We found 490 vacation rentals — enter your dates for availability

Discover a selection of 57 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.

Vacation rentals with weekly discounts - Westport

Showing deals for:Apr 17 - Apr 24

Image gallery for Updated Farmhouse Retreat

Exterior
10 out of 10, Exceptional, (8 reviews)
Exceptional
(8 reviews)

Updated Farmhouse Retreat

Wilton

9% off
Price is $1,271
$8,900 for 7 nights
All fees included
Updated Farmhouse Retreat

Find spaces that suit your style

  • Peace of mind

    Our Book with Confidence guarantee gives you 24/7 support

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, yards and more

  • More for less

    More space, more privacy, more amenities — more value

  • A place for everyone

    We stand for diversity, inclusion and families everywhere.
    Learn more

Find out more about Westport

Why visit Westport

  • Stunning Beaches: Westport boasts beautiful sandy beaches perfect for sunbathing, swimming, and picnicking.
  • Scenic Parks: Explore urban parks that offer walking trails, playgrounds, and stunning views of nature.
  • Cultural Experiences: Immerse yourself in local arts, history, and vibrant college atmospheres.
  • Charming Neighborhoods: Discover friendly, historical neighborhoods that enhance the coastal town's charm.
  • Diverse Accommodations: Choose from private homes, cozy apartments, and charming cottages for a perfect stay.

Popular types of accommodation in Westport

If you're exploring vacation rentals in Westport, you're in for a treat. Our most popular accommodations include houses, cozy apartments, and charming cottages. Whether you’re seeking a spacious house rental or a stylish apartment, we have a variety of rental listings in Westport to suit your needs. Enjoy transparency, savings, and reassurance as you find the perfect spot to unwind and explore this beautiful coastal town.

  • Houses: The top choice for visitors in Westport, offering spacious and comfortable accommodations ideal for families, friends, or couples.
  • Apartments: A favored option for those seeking modern living spaces with convenient amenities, perfect for a leisurely stay.
  • Cottages: These quaint and charming retreats provide a cozy atmosphere, perfect for a romantic getaway or a peaceful escape.
  • Cabins: A rustic option for nature enthusiasts, offering a serene setting amidst the beauty of the outdoors.
  • Condos: A practical choice combining comfort and community amenities, great for travelers wanting a home-like experience.**

Top attractions in and around Westport

Westport, Connecticut, is perfect for outdoor adventures and family or romantic getaways. Visitors can explore beautiful beaches, scenic urban parks, and the vibrant atmosphere of local colleges and universities. With a focus on outdoor activities and cultural experiences, Westport offers a variety of attractions that cater to all types of travelers seeking memorable experiences in this charming coastal town.

  • Fairfield University: This modern university offers a vibrant campus atmosphere just 5 miles from Westport. Visitors can enjoy its contemporary architecture, lush green spaces, and engaging cultural events that reflect a lively academic community.
  • Compo Beach: Located within Westport, Compo Beach boasts soft sands and inviting waters, making it a perfect spot for sunbathing, picnicking, and water sports. Its picturesque scenery is ideal for relaxation and family fun.
  • Historic South Norwalk: Just 4 miles away, this historic district is rich in culture, featuring charming architecture, waterfront dining, and boutique shops. Stroll through its streets to experience a blend of history and modern vibrancy.

Things to do recommended for couples

For a romantic getaway in Westport, enjoy a concert at Levitt Pavilion, savor exquisite wines at nearby Harmony Vineyards, or visit Del Vino Vineyards for a delightful tasting experience. Each spot offers a charming atmosphere perfect for couples to create lasting memories together.

Things to do recommended for families

For a memorable family vacation in Westport, explore the excitement at the Hartford HealthCare Amphitheater, enjoy the tranquility of Seaside Park, and discover the wonders of the Rolnick Observatory for a delightful blend of sports, relaxation, and entertainment.

Things to do recommended for groups

Group travelers in Westport can enjoy a captivating performance at the Westport Country Playhouse, explore local produce at the Westport Farmers Market, and indulge in shopping and entertainment at Stamford Town Center, located 11 miles away, offering a vibrant city atmosphere.

*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 traveling with friends, family, pets, or planning an extended stay, be sure to prioritize your filters accordingly. Here are some helpful Vrbo booking tips for you.

  • Traveling to Westport with a group: Think about how many bedrooms you'll require, along with additional features like a complete kitchen or outdoor areas for group gatherings. Luckily, you can easily filter for all of these options, and more, on Vrbo.
  • Traveling to Westport with young kids: Traveling with young kids can be quite a task. 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 family-friendly attractions.
  • Taking your pets with you to Westport: For many families, a vacation just isn’t the same without their furry companions. If you can relate, take a look at Vrbo listings that welcome pets. Most of these pet-friendly properties come equipped with feeding bowls and cozy beds, ensuring that everyone feels at home.
  • Planning for a long term stay visiting Westport: If you're seeking vacation rentals that offer discounts for stays of a month or more, you've come to the right spot. By applying the right filters, you can effortlessly discover and save on monthly rentals. Don't forget to include preferences 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 blend of outdoor adventures and charming local amenities, perfect for family, romantic, or business getaways. Explore the picturesque beaches and parks that highlight Westport's natural beauty. Nearby, experience the vibrant atmosphere of New York City while enjoying the friendly, historical neighborhoods that surround Westport. With its welcoming vibe and desirable locations, your vacation in Westport promises unforgettable moments and lasting memories.

  • Stamford: Stamford is a vibrant city located 11 miles from Westport, offering travelers a dynamic mix of family-friendly attractions and urban experiences. The city boasts a bustling shopping area, a thriving theater scene, and educational institutions that cater to all ages. Visitors can explore the charming tourist precinct and the lively square, including the popular modern square, which features a variety of shops and restaurants. Stamford's outdoor spaces provide opportunities for recreation and relaxation, making it a great spot for families looking to enjoy a day out in the city.
  • Norwalk: Just 3 miles from Westport, Norwalk is a delightful city that attracts families and outdoor enthusiasts alike. Known for its picturesque beaches and family-friendly attractions, Norwalk offers a variety of activities, from historic site explorations to beach outings. The city features a bustling shopping area and educational opportunities, making it perfect for a day trip. Visitors can relax at the family beach or enjoy a visit to one of the city’s historic places, creating memorable experiences in this charming coastal location.
  • Bridgeport: Located 9 miles from Westport, Bridgeport is a lively city that combines outdoor adventures with urban attractions. Families will find plenty to do, from visiting recreational areas to enjoying educational experiences. The city's shopping area offers a variety of retail options, while local landmarks such as the beach and family beach provide opportunities for fun in the sun. Sports enthusiasts can also catch events at the local stadium, making Bridgeport a must-visit for those looking to enjoy both culture and outdoor activities.

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

Booking with Vrbo is a breeze

Are you hoping to save on your upcoming trip? Being flexible with your travel dates can really help, as prices can vary quite a bit. Additionally, if you opt for a longer stay, you often unlock substantial savings. To discover the perfect Vrbo property that fits your budget, make use of our filters to sort by price, location, and type of vacation rental. We're here to help you find the best option for your needs.

Unlock savings with One Key

Reserve a qualifying Vrbo for your group getaway and earn OneKeyCash on your booking. Being the planner definitely has its perks. When you join our travel rewards program, One Key, you can immediately access member discounts and earn and redeem OneKeyCash on eligible reservations. Sign up now and begin enjoying your savings.

Vrbo Trips: Planning as easy as it gets

Vrbo's Trip Board is designed to help you plan your travel effortlessly. You can easily create new trips, manage your existing plans, or review and organize your bookings in one convenient place. Your saved or booked properties are neatly categorized into Potential, Upcoming, or Current Trips for quick access. To check out the Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

Gatsby-inspired vacations

From its gleaming Tiffany's store to its historic theater, Westport lives up to its reputation as the Beverly Hills of the East. For decades the riverside town has lured a constant stream of artists, celebrities and well-heeled holidaymakers. In fact, Westport was supposedly the inspiration for F. Scott Fitzgerald's The Great Gatsby. Not to mention Ira Levin's The Stepford Wives. Want to join the tribe? With Westport vacation rentals, you can unlock access to a host of exclusive properties in Westport's most coveted neighborhoods. Chances are, you'll soon be enjoying a G&T with your neighbor.

A slice of Broadway at the Westport Country Playhouse

Founded in 1931, the Westport Country Playhouse is one of Connecticut's most prestigious performing arts venues. Over the decades, the lovingly converted barn has staged hundreds of productions, overseen by local legends Paul Newman and Joanne Woodward. Check the website to see what's on. The Westport Arts Center takes a more casual approach, with colorful exhibits, theatrical performances, kids' classes and more. For a dose of sunshine, head to Sherwood Island State Park. Calm surf, shallow water and grassy picnic spots make its sandy beaches perfect for families.

Boutique hopping

Get your bearings with a stroll along Westport's upmarket main street. It's lined with an irresistible collection of designer boutiques, breezy cafes and upmarket seafood restaurants. For an in-depth introduction to the town, check out what's on at the Westport Historical Society. Based at the 1795 Bradley-Wheeler House, they offer walks and guided tours run by friendly locals. Westport enjoys a scenic setting by the Saugatuck River which means there are plenty of opportunities to swim, fish and paddle. Snag a riverfront Westport vacation rentals property and you'll have exclusive access to the water.

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)
  • 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)
  • Seaside Beach (8.2 mi / 13.2 km)

Transportation options to and around Westport

The nearest airport is in Westchester County Airport (HPN), located 18.7 mi (30.1 km) from the city center. If you can't find a flight that's convenient for your trip, you can also fly into New Haven, CT (HVN-Tweed - New Haven Regional), which is 25.8 mi (41.6 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, a popular area to stay is the Saugatuck neighborhood. This charming waterfront area is known for its picturesque views and vibrant atmosphere. Saugatuck is home to several top attractions, including the Saugatuck River, which offers opportunities for kayaking and paddleboarding, as well as a selection of delightful cafes and restaurants along the riverfront. The neighborhood is well-equipped with numerous vacation rental properties, providing a range of options for visitors looking for a cozy escape.

Another great area to explore is Compo Beach, which is great for those who enjoy sun, sand, and outdoor activities. The beach itself is a popular spot for swimming and picnicking, and it offers beautiful sunset views. Compo Beach is also close to the Westport Country Playhouse, a renowned theater known for its quality performances, making it an ideal choice for those interested in arts and culture.
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 traveling 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. To get the best value, book early and take advantage of Vrbo's free rewards program.
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 areas along the Long Island Sound are particularly appealing. The neighborhood near Compo Beach is a prime choice, where travelers can find charming beach houses that offer amenities such as spacious decks, outdoor grills, and stunning water views. Many properties in this area provide easy access to the sandy beach, making it ideal for families looking to spend time by the water.

Further along the coastline, the Saugatuck area presents additional options, with rentals that often come equipped with modern kitchens, cozy living spaces, and proximity to local dining and shopping. The Saugatuck River adds a picturesque backdrop, and some properties may even offer kayak rentals or access to boating activities.

In addition, the area around Burying Hill Beach features quieter, more secluded beach houses, superb for those seeking tranquility. Properties here typically include amenities like private outdoor spaces and easy access to walking trails along the shore. Find your rental near the beach in Westport.
What is the most popular type of vacation rental accomodation in Westport?
In Westport, vacation houses are the most popular type of rental accommodation, with about 35 available throughout the area. These houses often feature spacious layouts, multiple bedrooms, fully equipped kitchens, and outdoor areas such as patios or decks for enjoying the pleasant surroundings. Many are located in serene neighborhoods, providing a peaceful retreat while still being close to local attractions like Compo Beach and the charming downtown area. Additionally, there are several apartments, cottages, and condos available, which cater to different preferences and group sizes.
Are there any family house rentals in Westport?
In Westport, Connecticut, there are numerous family-friendly house rentals available, with around 29 options to choose from. This charming town is known for its picturesque coastal views and vibrant community, making it an excellent choice for families. Many of the homes feature spacious living rooms, full kitchens that are great for preparing family meals, and outdoor areas where children can play safely.

Visitors can find properties with amenities such as game rooms, private yards, and even access to nearby beaches for summer fun. The neighborhoods of Compo Beach and Saugatuck are particularly appealing, as they offer quick access to local parks, recreational activities, and waterfront dining options.

In addition to its beautiful scenery, Westport boasts a rich cultural scene, with nearby attractions like the Westport Country Playhouse and the charming shops and restaurants along Main Street. See all family-friendly rentals in Westport.
Can I rent a vacation home with a pool or hot tub in Westport?
In Westport, there are several vacation homes available for rent that feature pools and hot tubs, with around 11 options to choose from. This picturesque coastal town offers a blend of suburban charm and easy access to the waterfront. Many of the properties come equipped with private pools, hot tubs, and spacious outdoor areas ideal for relaxation and entertaining.

Travelers can expect various amenities in these rentals, including fully equipped kitchens, expansive living spaces, and well-maintained gardens. Find your rental in Westport with a pool or a hot tub.
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. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* 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.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Are there pet-friendly house rentals in Westport?
In Westport, travelers can find a variety of pet-friendly house rentals, with around 19 options available. The area is known for its charming coastal atmosphere and beautiful beaches, making it a great choice for those looking to enjoy a seaside getaway with their pets. Many of the vacation rentals in Westport come equipped with amenities such as spacious backyards, fully equipped kitchens, and outdoor spaces superb for relaxing after a day of exploring.

The neighborhood's proximity to Compo Beach is a highlight, where pet owners can enjoy the sandy shores and scenic views while walking their dogs. Additionally, the nearby Sherwood Island State Park offers walking trails and picnic areas, ideal for spending time outdoors with pets. See all pet-friendly rentals in Westport.
Are there any remote work vacation rentals in Westport?
In Westport, Connecticut, there are numerous options for remote work vacation rentals, with around 29 properties available. This charming coastal town offers a variety of accommodations that cater to remote workers, featuring amenities such as dedicated office spaces, high-speed Wi-Fi, comfortable desk chairs, and even computer monitors in some rooms. Travelers can expect well-appointed homes that provide a peaceful environment for productivity while being close to local attractions.

The town is known for its picturesque waterfront, beautiful parks, and vibrant downtown area, which includes shops, cafes, and restaurants, superb for breaks in between work. The nearby Compo Beach and Longshore Club Park offer opportunities for relaxation and outdoor activities after a day of work. 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 travelers 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 vacation rental amenities include kitchens, allowing guests to prepare their own meals, and WiFi for staying connected. Many rentals also feature coffee and tea makers, ideal for enjoying a warm beverage in the morning. Additionally, travelers can expect patios for outdoor relaxation, making it easy to enjoy the fresh coastal air.
When is the best time to visit Westport for a vacation rental?
The best time to book a vacation rental in Westport is during the peak season from May to July, particularly in July when the town is buzzing with activity. This is the ideal period for travelers seeking a vibrant atmosphere, as the warm summer weather creates superb conditions for enjoying outdoor activities. Expect pleasant temperatures generally ranging from the mid-60s to the low 80s Fahrenheit, making it comfortable for sunbathing on the beach, strolling along the scenic boardwalk, or indulging in local seafood at waterfront restaurants.

In addition to sun-soaked days, July is also a prime time for cultural events, including summer festivals and art shows that showcase the best of Westport's creative community. Visitors can experience firsthand the local culture while enjoying a variety of outdoor concerts and performances.

For those looking for a more economical option, consider visiting in October. This month, while quieter, offers its own charm with the stunning fall foliage transforming the landscape into a tapestry of colors.
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 explore a variety of attractions that highlight the town's coastal charm and artistic culture. The Saugatuck River runs through the heart of Westport, offering scenic views and opportunities for kayaking or paddleboarding. The area around the river is lively, with shops, cafes, and restaurants that provide a vibrant atmosphere.

The Westport Country Playhouse is a cultural gem, showcasing a range of theatrical performances and engaging events throughout the year. For those interested in art, the Westport Arts Center offers exhibitions and classes, further enriching the local creative scene.

Another attraction is Compo Beach, a popular spot for both locals and visitors, featuring sandy shores, picnic areas, and a scenic boardwalk superb for walks and relaxation. Additionally, the nearby Sherwood Island State Park offers hiking trails and beautiful views of Long Island Sound, making it an ideal place for outdoor enthusiasts.
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 rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, 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 travelers 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 cozy cabin or a beach condo, 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 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.
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 like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively.Vrbo also offers support via live chat through our Help Center, 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 organizing 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.

More Vacation Ideas