Westport Vacation Rentals, Connecticut: house rentals & more

Discover a selection of 51 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.

Find spaces that suit your style

House

Condo/Apartment

Find properties near top attractions in Westport

Compo Beach

Find the best place to stay - Westport

Your perfect Westport getaway is here!

Sleeps 4 · 2 bedrooms · 1 bathroom

Farmhouse 1899: Westport, CT - Minutes to Downtown, family and pet-friendly.

Sleeps 9 · 3 bedrooms · 2 bathrooms

Come to your summer home-mile to Saugatuck/Compo-bright, open, airy, fenced yard

Sleeps 8 · 4 bedrooms · 2+ bathrooms

Top rated rentals - Westport

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Find out more about Westport

Why visit Westport

Beautiful beaches: Enjoy the stunning coastline and sandy shores, perfect for relaxation and outdoor activities.
Outdoor adventures: Explore vibrant parks and recreational opportunities along Hillspoint Road for an active getaway.
Family-friendly activities: Discover a range of attractions suitable for families, ensuring fun for all ages.
Charming accommodations: Choose from cozy cottages and modern apartments, catering to every traveler's needs.
Romantic atmosphere: Experience a delightful setting for couples, making it ideal for a romantic retreat.

Popular types of accommodation in Westport

Planning a getaway to Westport? Discover the perfect accommodation to suit your needs! From charming cottages and spacious houses to modern apartments, Westport offers a variety of rental options. Whether you’re searching for rentals near Westport, apartments with pools, or cozy bedroom apartments, you’ll find a range of choices that provide comfort and convenience. Start your adventure today and find your ideal home away from home!

Houses: The top choice for visitors in Westport, offering spacious and comfortable settings ideal for families or groups.
Apartments: A popular option for those seeking modern amenities and convenient locations for a memorable stay.
Cottages: Quaint and charming, these rentals provide a cozy retreat for a relaxing getaway.
Cabins: Perfect for nature lovers, offering rustic charm and proximity to the great outdoors.
Condos: Stylish living spaces that combine comfort with community amenities, great for short or extended stays.**

Top attractions in Westport

Westport, Connecticut, is an ideal destination for outdoor enthusiasts, families, and couples seeking a romantic getaway. With its stunning beaches, vibrant urban parks, and modern college campuses, the area offers a diverse range of attractions. Visitors can enjoy a mix of outdoor adventures and cultural experiences, making it a perfect spot for creating lasting memories while exploring the local charm.

Fairfield University: A vibrant campus with modern architecture and a lively atmosphere, just 8.0km from Westport. Experience the energy of student life and explore cultural events, art exhibitions, and beautiful green spaces.
Compo Beach: A stunning local beach offering soft sand, calm waters, and picturesque views. Perfect for sunbathing, picnicking, or enjoying water activities, Compo Beach provides a relaxing seaside escape right within Westport.
Historic South Norwalk: Rich in history and culture, located 6.4km away. Discover charming streets, artisanal shops, and museums that showcase the area’s heritage, making it a delightful spot for leisurely exploration.

Things to do recommended for couples

Discover the charm of Westport, Connecticut, with a romantic evening at Levitt Pavilion's live concerts. Enjoy an adventurous day at Waterski Connecticut, or indulge in wine tasting at Harmony Vineyards, perfect for couples seeking entertainment and romance amidst beautiful scenery.

Things to do recommended for families

Your family will love visiting Rolnick Observatory for a fun-filled day of stargazing. Enjoy outdoor activities at Seaside Park, perfect for relaxation, and catch an event at the Hartford HealthCare Amphitheater for an exciting sports atmosphere, all within a short drive from Westport.

Things to do recommended for groups

Experience the vibrant culture at the Westport Country Playhouse, enjoy fresh produce at the Westport Farmers Market, or indulge in shopping and entertainment at Stamford Town Center, located 17.7km away. These activities promise a memorable group experience in Westport!

What do I need to keep in mind when booking a vacation in Westport

When travelling with a group, family, pets, or planning an extended stay, it's important to prioritize your preferences. Here are some helpful Vrbo booking tips for you.

Traveling to Westport with a group: Think about how many bedrooms you require, along with features like a complete kitchen or outdoor area for group get-togethers. Luckily, you can easily refine your search for all these options and more on Vrbo.
Traveling to Westport with young kids: Traveling with young children can present its own set of challenges. It's essential to prioritize their comfort and safety, along with providing age-appropriate facilities, 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 getaway feels incomplete without their furry companions. If you can relate, take a look at Vrbo properties that welcome pets. Most pet-friendly accommodations come equipped with feeding bowls and beds, ensuring that everyone feels comfortable and at home.
Planning for a long term stay visiting Westport: If you're in search of vacation rentals offering discounts for month-long stays, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Also, think about including features like parking availability, a well-equipped kitchen, or a private pool in your search criteria.

Where to stay in Westport

Westport, Connecticut, offers a delightful blend of outdoor adventures and family-friendly activities, making it an ideal vacation spot. Explore nearby cities like West Vancouver and New Westminster for a cozy retreat, or enjoy the recreational opportunities along Hillspoint Road. With its sunny weather and friendly people, Westport promises a romantic atmosphere perfect for couples and families alike, ensuring a memorable getaway.

Stamford: Located 17.7km from Westport, Stamford is a vibrant city that offers a delightful blend of family-friendly activities and urban experiences. Known for its shopping areas and cultural venues, Stamford's modern square is a must-visit. Here, you can enjoy a variety of restaurants, theatres, and educational institutions. The city’s dynamic atmosphere makes it an excellent destination for those looking to explore lively urban life while also appreciating outdoor spaces and parks. Don't miss the local tourist precinct, where you can immerse yourself in community events and activities.
Norwalk: Just 4.8km from Westport, Norwalk is a charming city that attracts visitors with its family-oriented attractions and outdoor adventures. Known for its beautiful beaches and historic sites, Norwalk offers a unique coastal experience. Families can enjoy a day at the beach or visit the local casino for entertainment. The shopping areas in Norwalk are also appealing for those looking to take home unique finds. With its blend of education, recreation, and culture, Norwalk is perfect for those seeking both relaxation and exploration.
Fairfield: Situated 8.0km from Westport, Fairfield is a lively city renowned for its outdoor activities and cultural experiences. The presence of a modern college university enhances the city's vibrant atmosphere, making it a hub for education and community events. Visitors can enjoy recreational areas and family-friendly beaches, perfect for a day of sun and sand. With its array of shopping options and casinos, Fairfield invites tourists to indulge in both leisure and excitement, ensuring a well-rounded experience during your stay.

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 simple

Are you hoping to save on your upcoming journey? Being flexible with your travel dates can lead to great savings, as prices often fluctuate. Additionally, booking a longer stay can provide you with substantial discounts. To discover a Vrbo property that aligns with your budget, feel free to use our convenient 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 cutting-edge Trip Board offers you a dedicated space to plan new trips, pick up right where you left off, or easily manage and arrange your travel plans. You can now find the properties you've saved and booked categorized under Potential, Upcoming, or Current Trips. To start using 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)
Fairchild Wheeler Golf Course (7.7 mi / 12.4 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)
Great River Golf Club (17.1 mi / 27.5 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)
Southport Beach (3.3 mi / 5.4 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)

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 most popular type of vacation rental accommodation in Westport?

The most desirable types of vacation rentals in Westport are houses. After something a little different? Vrbo has a variety of options to match our guests’ needs, so you’ll see vacation homes in lots of shapes and sizes. The ideal home away from home is waiting for you — snap up yours today.

How much does it cost to rent a vacation rental in Westport?

Property type, length of stay and time of year are some factors that can influence the price of a vacation home. Simply add your travel dates to find your perfect match. From cozy chalets to sprawling villas, all Vrbo vacation rentals provide incredible value.

How much does it cost to rent a beach house in Westport?

Prices for beach houses in Westport differ depending on the style and size of the property and time of year you’re traveling. Simply enter your travel dates into Vrbo and the number of guests to view your options and prices. From there you can use our filters to refine your search by ratings, amenities and more.

Are there pet-friendly vacation rentals in Westport?

Pack a suitcase for your pooch because Westport has 48 vacation rentals that put out the welcome mat to pets. Let your furriest pal enjoy fun with the family at one of our pet-friendly vacation rentals on Vrbo. Simply enter your travel dates then check our “Pets allowed” filter box.

Can I rent a house with a pool in Westport?

Mark the “pool” box in our filter tool and you can choose from 20 houses with private pools in Westport on Vrbo. Lazy soak or ball games and races? How you spend your leisure time is up to you when your vacation home comes with its own swimming pool.

What are popular rental amenities in Westport?

When it comes to rental amenities that guests prefer in Westport, an electric car charging station, a nearby waterfront and a sauna rank the highest. With Vrbo vacation rentals, there are choices to suit your taste and style, whether you’re planning to get away with family members, friends or even pets.

Are there large group vacation rentals in Westport?

Westport has 11 vacation rentals that can fit 10 or more people. These stays come with plenty of space to share good times with loved ones.

Are there vacation rentals in Westport that welcome kids?

Westport has 47 family-friendly vacation rentals to choose from. And booking a stay that welcomes kiddos is a breeze with Vrbo’s “Properties good for families” filter. As well as having the whole place to yourselves, you’ll enjoy access to amenities and perks such as living rooms, kitchens and pools.

What are the top attractions for families in Westport?

There are plenty of awesome things to do and see with the family in Westport, such as:

Compo Beach
Norwalk Maritime Aquarium
Jennings Beach

Are there one-bedroom vacation rentals in Westport?

Yes, you can take your pick from five one-bedroom rentals in Westport. Whether you’re looking for a cozy cottage or a fancy condo, Vrbo’s one-bedroom properties are perfect if you don’t require a huge amount of space. One of the major perks of having your own digs? You won’t ever have to share your adventure with strangers.

Can I find two-bedroom vacation rentals in Westport?

Take off with your loved ones and relax in total privacy and comfort in one of the three two-bedroom vacation properties Westport has to offer.

Are there vacation rentals with WiFi in Westport?

Westport has 15 vacation rentals with WiFi, so you can stay connected while you’re on vacation. Simply check the “WiFi” box in our search filter for a list of properties with this feature. From streaming movies with your family to catching up on social media, these Vrbo homes will keep you online.

How can I find vacation rentals with air conditioning in Westport?

Pick your travel dates and then use our filters to view vacation rentals with air conditioning in Westport on Vrbo. With 46 air-conditioned properties on offer here, you can look forward to a comfortable and cool stay.

How old do you have to be to rent a vacation rental in Westport?

The minimum age is typically 16, 18 or 21. It can differ between properties on Vrbo, so check the rules of your chosen Westport stay before booking your escape.

How long can I rent a vacation rental in Westport for?

The length of time you can book a vacation rental in Westport is up to the property. Just enter your selected travel dates to look at a list of options offering extended stays. With many creature comforts such as kitchens and air conditioning, as well as some offering discounted weekly or monthly prices, you’re sure to get someplace just right to call your home away from home in Westport.

Explore destinations around Westport

Sherwood Island State Park (270)

Old Mill Beach (301)

Compo Beach (260)

Alvord Beach (265)

Burying Hill Beach (264)

Earthplace Museum (271)

Westport Historical Society (759)

Levitt Pavilion (759)

Westport Country Playhouse (761)

It's easy to contact hosts and keep track of all your messages when you have a Vrbo account

Find spaces that suit your style

Find properties near top attractions in Westport

Compo Beach