Westport vacation rentals

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.

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.

Calendar Month	Temperature	Precipitation	Cloudiness	Occupancy	Pricing
January	31.5°F (-0.3°C)	Light Rain	Mostly Sunny	Slightly Low	Slightly Low
February	32.7°F (0.4°C)	Light Rain	Mostly Sunny	Slightly Low	Slightly Low
March	39.2°F (4.0°C)	Light Rain	Mostly Sunny	Average	Slightly Low
April	49.5°F (9.7°C)	Light Rain	Mostly Sunny	Slightly High	Average
May	59.4°F (15.2°C)	Light Rain	Mostly Sunny	Slightly High	Average
June	68.4°F (20.2°C)	Light Rain	Mostly Sunny	Average	Slightly High
July	75.4°F (24.1°C)	Light Rain	Mostly Sunny	Slightly High	Slightly High
August	74.1°F (23.4°C)	Light Rain	Mostly Sunny	Average	Slightly High
September	67.6°F (19.8°C)	Light Rain	Mostly Sunny	Average	Average
October	57.4°F (14.1°C)	Light Rain	Mostly Sunny	Slightly Low	Average
November	45.9°F (7.7°C)	Light Rain	Mostly Sunny	Average	Average
December	37.9°F (3.3°C)	Light Rain	Mostly Sunny	Average	Average

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.

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.