Weston holiday lettings

We found 378 holiday rentals — enter your dates for availability

Discover a selection of 14 homes and other holiday rentals in Weston that are perfect for your trip. Whether you’re staying in a holiday home with your children or with friends, you'll have the amenities that you expect and more, which might include parking and a hot tub. At the end of the day, you'll be sure to find a property to rent that has what everyone needs, including a place that's non-smoking or offers accessibility.

Holiday rentals with weekly discounts - Weston

Showing deals for:24 Oct - 31 Oct
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Why visit Weston

  • Scenic outdoor activities: Enjoy a variety of outdoor pursuits in Weston, from hiking to leisurely walks in tranquil parks.
  • Charming neighbourhoods: Explore picturesque streets lined with stunning homes, reflecting the town's unique character.
  • Cultural experiences: Discover local culture through nearby historical sites and engaging community events.
  • Romantic getaways: Perfect for couples, Weston offers a serene atmosphere ideal for a romantic retreat.
  • Diverse accommodation: Choose from an array of delightful rentals, including cosy cottages and modern apartments.

Popular types of accommodation in Weston

Planning a getaway to Weston? You're in for a treat! Discover the charm of this destination with an array of accommodation options. From houses and cosy cottages to comfortable apartments, there's something to suit every traveller's needs. Explore our extensive rental listings in Weston to find the perfect home rentals and house rentals that promise a delightful stay. Your ideal holiday retreat awaits!

  • Houses: The most sought-after option, ideal for families or groups seeking a home-away-from-home experience in Weston.
  • Apartments: A popular choice for those looking for convenience and a touch of urban living during their stay in Weston.
  • Cottages: Quaint and charming, these accommodations offer a picturesque retreat in the heart of Weston.
  • Cabins: Perfect for nature lovers, cabins provide a rustic experience amidst the beautiful surroundings.
  • Condos: These stylish living spaces offer modern amenities and are great for a comfortable stay in Weston.**

Top attractions near Weston

Weston, Connecticut, is an ideal destination for outdoor enthusiasts and couples seeking a romantic getaway. With its stunning beaches, urban parks, and modern colleges, the area offers a variety of attractions that cater to those interested in culture and family experiences. Whether you're exploring scenic landscapes or enjoying leisurely activities, Weston provides a charming backdrop for an unforgettable holiday.

  • Fairfield University: A modern institution boasting vibrant city vibes, Fairfield University offers beautiful campus grounds, contemporary architecture, and a lively atmosphere. It's an excellent spot for a leisurely stroll or to enjoy cultural events.
  • Historic South Norwalk: Rich in culture and history, this charming area features cobblestone streets, historic buildings, and an array of quaint shops and eateries. It's perfect for exploring local heritage and enjoying the arts.
  • Compo Beach: A picturesque beach destination, Compo Beach presents stunning coastal views and a relaxing atmosphere, ideal for sunbathing, swimming, and beachside picnics.

Things to do recommended for couples

Searching for a romantic getaway in Weston? Be sure to catch a concert at Levitt Pavilion, only 2.5km away, for a lively atmosphere. Alternatively, indulge in a wine tasting at DiGrazia Winery, located 11.8km away, where romance meets entertainment in a charming setting.

Things to do recommended for families

Families visiting Weston, Connecticut, can enjoy a relaxing day at Seaside Park, explore the stars at Rolnick Observatory, or engage in sports activities at Pitt Center, all within a short drive from the town.

Things to do recommended for groups

While in Weston, groups can enjoy a captivating performance at the Westport Country Playhouse, indulge in retail therapy at the nearby Center Seven Shopping Center, or explore the Caldor Shopping Center for a delightful mix of shopping and dining experiences, all within a short distance.

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

If you're planning a trip with a group, family, pets, or seeking longer stays, it's essential to filter according to your specific needs. Here are some helpful Vrbo booking tips for you.

  • Traveling to Weston with a group: Think about how many bedrooms you'll require, along with features like a fully equipped kitchen or outdoor space for group gatherings. Thankfully, you can easily refine your search for these options and more on Vrbo.
  • Traveling to Weston with young kids: Going on holiday with young children can be quite demanding. It's important to prioritise their comfort and safety, along with suitable amenities for their age, like a private swimming pool. Additionally, it's wise to think about how close you are to attractions that are suitable for families.
  • Taking your pets with you to Weston: For many, a family holiday isn't truly complete without their furry companion by their side. If this resonates with you, explore Vrbo properties that welcome pets. Most pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Weston: If you're in search of holiday rentals offering discounts for stays of a month or more, you've come to the right spot. By using the appropriate 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 Weston

Weston, Connecticut, offers a delightful blend of outdoor activities and picturesque scenery, perfect for a romantic getaway or a family-friendly vacation. Explore charming neighbourhoods with stunning homes, and enjoy the welcoming atmosphere that defines this lovely town. Nearby areas present a wealth of historical sites and engaging experiences, making it an ideal base for discovering the beauty of New England. From tranquil parks to vibrant local culture, Weston is a hidden gem waiting to be explored.

  • Stamford: Located 8.1km from Weston, Stamford is a vibrant city that offers a rich array of experiences for every visitor. Known for its family-friendly atmosphere, Stamford combines urban sophistication with outdoor charm. The city boasts an impressive shopping area, a variety of theatres, and educational institutions. Noteworthy attractions include the bustling tourist precinct and Modern Square, where you can enjoy dining and entertainment. Perfect for a day trip, Stamford’s blend of city life and scenic parks makes it an ideal destination for those seeking both leisure and culture.
  • Norwalk: Just 3.7km from Weston, Norwalk is a delightful city perfect for families and outdoor enthusiasts. Visitors can explore its picturesque beaches, including family-friendly options, and delve into the area's rich history at its historic sites. Norwalk also features a vibrant shopping area and educational facilities, making it a well-rounded destination. Whether you’re looking to relax on the shore or partake in various seasonal activities like skiing, Norwalk offers a charming blend of attractions that cater to all interests.
  • Bridgeport: Situated 6.2km away from Weston, Bridgeport is a lively city known for its welcoming atmosphere, making it a great spot for families. With recreational areas and educational institutions, it promises a fulfilling visit. The city's coastline features beautiful beaches, perfect for a day of sun and sand, while the famous stadium adds a touch of excitement for sports enthusiasts. Bridgeport's shopping areas offer a variety of options for those looking to indulge in retail therapy, ensuring a well-rounded experience for all visitors.

Best time to go to Weston

If you're planning a trip to Weston, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs in June to July and September, while off-peak times, like December to February tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January30.6°F (-0.8°C)Light RainMostly SunnySlightly LowSlightly Low
February32.0°F (0.0°C)Light RainMostly SunnySlightly LowSlightly Low
March38.7°F (3.7°C)Light RainMostly SunnyAverageSlightly Low
April48.9°F (9.4°C)Light RainMostly SunnyAverageAverage
May59.0°F (15.0°C)Light RainMostly SunnyAverageAverage
June67.8°F (19.9°C)Light RainMostly SunnySlightly HighSlightly High
July74.7°F (23.7°C)Light RainMostly SunnySlightly HighSlightly High
August73.4°F (23.0°C)Light RainMostly SunnyAverageSlightly High
September66.7°F (19.3°C)Light RainMostly SunnySlightly HighAverage
October56.7°F (13.7°C)Light RainMostly SunnyAverageAverage
November45.3°F (7.4°C)Light RainMostly SunnyAverageAverage
December36.9°F (2.7°C)Light RainMostly SunnySlightly LowAverage

Booking with Vrbo is simple

Are you keen to make some savings on your next getaway? Being flexible with your travel dates can be beneficial, as prices often fluctuate. Additionally, opting for a longer stay can lead to substantial discounts. To discover a Vrbo property that suits your budget, utilise our filters to sort by price, location, and type of holiday rental.

Vrbo Trips: Planning made easy

Vrbo’s Trip Board provides a convenient platform for you to plan new journeys, refine your existing arrangements, or manage your bookings with ease. Your saved or reserved properties are now categorised into Potential, Upcoming, or Current Trips for better organisation. To discover the features of Trip Boards, please visit: https://www.vrbo.com/en-gb/trips.

**Based on Vrbo properties bookings.

Book a holiday rental for your Weston getaway

Learn about the unique charm of Weston with a stay in a holiday home rental. This city has something for everyone. A holiday rental can help make your stay complete—many rentals come with a full kitchen and laundry facilities.

Activities and attractions in and around Weston

Are you looking for things to do in the city? Venture out of your holiday home and experience everything that makes Weston a fun spot to go on holiday. These 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 (7.2 mi / 11.7 km)
  • Beardsley Zoo (10.4 mi / 16.7 km)
  • Chelsea Piers (12.4 mi / 19.9 km)
  • Hand & Stone Massage and Facial Spa (12.6 mi / 20.3 km)
  • E. Gaynor Brennan Golf Course (13.5 mi / 21.8 km)
  • Stanwich Club (13.8 mi / 22.1 km)

Exploring the natural landscape of Weston

Whether you're looking for exciting outdoor activities or just want to take in the scenery, Weston is a great place to spend some time outside. These are some of the area's most eye-catching features, all within 30 miles (48.2 km) of the city centre:

  • Lucius Pond Ordway / Devil's Den Preserve (2.6 mi / 4.2 km)
  • Old Mill Beach (5.3 mi / 8.5 km)
  • Lake Mohegan (6.5 mi / 10.5 km)
  • Southport Beach (6.8 mi / 10.9 km)
  • Compo Beach (6.9 mi / 11 km)
  • Calf Pasture Beach (7.9 mi / 12.7 km)

Transport options to and around Weston

The nearest airport is in Danbury, CT (DXR-Danbury Municipal), located 13.1 mi (21 km) from the city centre. If you can't find a flight that works for your travel itinerary, you could also fly into Bridgeport, CT (BDR-Igor I. Sikorsky Memorial), which is 13.3 mi (21.3 km) away.

Frequently asked questions

What is the most popular type of holiday rental accommodation in Weston?
Houses are the most popular style of holiday rental in Weston, according to our data. Even if you've got a different idea about what you want, Vrbo has holiday homes in all shapes and sizes. Browse our options to find your perfect Weston pad.
How much does it cost to rent a holiday rental in Weston?
A range of things affect the price of a holiday rental in Weston, including the length of stay, type of property and season. Still, all of our holiday homes have something in common — amazing value. Simply enter your travel dates to find your ideal escape.
How much does it cost to rent a beach house in Weston?
Prices for beach houses in Weston may vary depending on the size and type of the property and when you're travelling. Simply enter your dates of travel into Vrbo and how many guests to see your options and prices. From there you can use our filters to refine your search by amenities, ratings, nearby activities and more.
Are there pet-friendly holiday rentals in Weston?
Pack a suitcase for your canine companion because Weston has 11 holiday rentals that throw open their doors to pets. Let your furriest pal join in on the family trip at one of our pet-friendly holiday rentals on Vrbo. Simply enter your destination and travel dates, then check our "Pets allowed" filter box.
Can I rent a house with a pool in Weston?
Add a whole other level of fun to your trip by booking your group into one of the six houses with a private pool in Weston. Use our handy search filter to find the kind of property you want on Vrbo, and then spend lazy days splishing and splashing in a swimming pool that's all your own.
What are popular rental amenities in Weston?
When it comes to rental amenities that guests look for in Weston, a firepit, a nearby waterfront and nearby museums are the most popular. With Vrbo holiday homes, there are choices to suit your style and taste, whether you're taking a trip with family members, friends or even pets.
Are there large group holiday rentals in Weston?
Yes, you can choose one of four holiday rentals in Weston that can accommodate five or more guests. From family reunions to events like birthday parties, these stays have enough room to kick back with the people that matter the most.
Are there holiday rentals in Weston that welcome kids?
With 11 family-friendly holiday properties to pick from in Weston, now is the perfect time to introduce the little ones to the excitement of travel. Just click on our "Properties good for families" filter box to discover stays loaded with amenities perfect for families on the move, like extra bedrooms, pools, bunk beds and hot tubs.
What are the top attractions for families in Weston?
There are lots of fabulous things to see and do with the family in Weston, such as:

  • Compo Beach
  • Norwalk Maritime Aquarium
  • Jennings Beach

Are there one-bedroom holiday rentals in Weston?
Yes, there are three one-bedroom properties in Weston to pick from. A one-bedroom holiday home is an excellent option if it's just you and your sweetheart or if you're holidaying solo. Add in more space, privacy and convenience compared to a standard hotel, and you're bound to have an unforgettable trip.
Are there holiday rentals with WiFi in Weston?
Whether you want to keep up with the headlines, look over emails or update your social media, there are seven holiday homes with WiFi in Weston. Check the "WiFi" box when searching on Vrbo and stay connected on your holiday.
How can I find holiday rentals with air conditioning in Weston?
Choose from 11 Vrbo holiday homes with air conditioning in Weston providing that cool, cool breeze and extra element of comfort. Enter your desired travel dates and then take advantage of our filter tool to help you book stays with air conditioning.
How old do you have to be to rent a holiday rental in Weston?
The minimum age can differ across properties on Vrbo, so be sure to check the rules of the holiday rental in Weston you want to book. But normally, it's 16, 18 or 21.
How long can I rent a holiday rental in Weston for?
The amount of time you can stay in a Weston holiday rental for is up to the property. Just enter your preferred travel dates to view options that offer long-term stays. They feature all the things you need to make your extended trip more convenient and enjoyable, such as kitchens and backyards. Some properties may also offer weekly or monthly discounted prices, so you can hang around longer for less.

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