Weston holiday lettings

We found 376 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:12 Dec - 19 Dec

Image gallery for Fairfield Old Post Road-heated pool & Guest Cottage-walk to NYC train and Beach!

Ivy Covered Tudor on the Old Post Road in Fairfield.
9.8 out of 10 rating
Exceptional
(19 reviews)

Fairfield Old Post Road-heated pool & Guest Cottage-walk to NYC train and Beach!

Fairfield, CT

8% off
Price is £9,141
for 7 nights, 1 home
£1,306 per night
includes taxes & fees
Fairfield Old Post Road-heated pool & Guest Cottage-walk to NYC train and Beach!

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Find out more about Weston

Find out more about Weston

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)
  • Country Club of Fairfield (7.5 mi / 12.1 km)
  • Beardsley Zoo (10.4 mi / 16.7 km)
  • Chelsea Piers (12.4 mi / 19.9 km)
  • Great River Golf Club (16.4 mi / 26.3 km)
  • Richter Park Golf Course (16.4 mi / 26.5 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:

  • 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)
  • South Pine Creek Beach (8 mi / 12.9 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 best area to stay in Weston when booking a holiday rental?
When considering a holiday rental in Weston, Connecticut, the best area to stay is around the scenic Weston Town Centre. This charming neighbourhood offers a blend of picturesque surroundings and convenient access to local attractions. The Town Centre is home to several delightful shops and eateries, making it an ideal spot for those who enjoy a vibrant community atmosphere.

Another appealing area is near the Aspetuck Valley Country Club, which not only provides beautiful views but also offers recreational activities for golf enthusiasts. Additionally, nature lovers will appreciate the proximity to the scenic Weston Woods, an excellent location for hiking and enjoying the great outdoors.
How much does it cost to rent a holiday home in Weston?
Prices for holiday rentals in Weston 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 Weston 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 Weston holiday house rentals?
You can find great discounts on house rentals in Weston 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 Weston?
For renting a beach house in Weston, Connecticut, travellers may want to explore the nearby coastal towns of Westport and Southport, both of which offer charming beachside living. Westport, located just a short drive away, features lovely properties along the Saugatuck River and near Compo Beach. Many of the rentals in this area come with amenities such as spacious outdoor decks, barbecues, and access to private beach areas, making them great for family gatherings or relaxing getaways.

Southport, with its picturesque coastline and quaint village charm, is another excellent choice. Here, visitors can find delightful cottages and larger homes that often include features like modern kitchens, open-plan living spaces, and proximity to local parks and waterfront dining options. Properties in this area may also offer views of Long Island Sound, enhancing the seaside experience.
Where are the best Weston ski resort rentals?
For skiing near Weston, Connecticut, the closest ski resort options are located in the nearby region of the Berkshires in Massachusetts, particularly around towns like Great Barrington and Lenox. These areas offer a variety of holiday rentals, from cosy cabins to larger homes suitable for families or groups. Many properties come with amenities such as fireplaces, fully equipped kitchens, and outdoor spaces for après-ski relaxation.

In Great Barrington, you can find rentals that provide easy access to the slopes, with some properties featuring hot tubs for unwinding after a day of skiing. The town itself boasts a vibrant arts scene, local shops, and dining options, making it a convenient base for travellers.

Lenox, known for its cultural attractions, including the renowned Tanglewood Music Centre, offers charming properties set in picturesque surroundings. Many rentals here provide spacious living areas, modern conveniences, and are often located near scenic hiking trails for winter walks or snowshoeing.
What is the most popular type of holiday rental accomodation in Weston?
In Weston, holiday houses and cottages are the most popular types of rental accommodations, with several options available throughout the area. These properties tend to be spacious and well-equipped, often featuring multiple bedrooms, fully furnished kitchens, and inviting living areas. Many of these rentals also boast outdoor spaces such as gardens or patios, providing great spots for relaxation after exploring the picturesque surroundings.
Are there any family house rentals in Weston?
In Weston, Connecticut, there are ten family-friendly house rentals available, offering a variety of options for those travelling with children. This charming town is known for its picturesque landscapes and family-friendly atmosphere. Many of these homes provide spacious living areas, fully equipped kitchens for preparing meals together, and outdoor spaces where children can play safely.
Can I rent a holiday home with a pool or hot tub in Weston?
In Weston, Connecticut, there are several holiday homes available for rent that come equipped with pools or hot tubs. This picturesque town offers a tranquil escape with its beautiful natural surroundings, making it an ideal location for a relaxing getaway. The properties often feature spacious outdoor areas, allowing guests to enjoy the poolside ambiance, as well as well-appointed interiors with modern amenities. Travellers can expect features like fully equipped kitchens, comfortable living spaces, and sometimes even outdoor dining options.
Can I find long-stay holiday rentals in Weston?
A long-stay holiday rental in Weston 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 Weston?
In Weston, there are several pet-friendly house rentals available, offering a variety of amenities to ensure a comfortable stay for both you and your furry companions. Many of these properties feature spacious yards, allowing pets to roam freely, as well as modern kitchens and cosy living areas superb for family gatherings.
Are there any remote work holiday rentals in Weston?
In Weston, Connecticut, there are several remote work holiday rentals available, with around 10 options to choose from. This picturesque town is renowned for its serene environment, making it an ideal setting for those looking to combine work and leisure. Many of these properties come equipped with essential amenities for remote work, including high-speed Wi-Fi, dedicated desks, comfortable desk chairs, and laptop workspaces. Some may even feature offices or computer monitors to enhance your productivity. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Weston holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in Weston 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 Weston?
In Weston, popular rental amenities include fully equipped kitchens, which allow guests to prepare their own meals during their stay. Many properties also feature microwaves for quick meal options and patios where visitors can relax outdoors. Additionally, coffee-making facilities are commonly available, making it easy to enjoy a fresh brew in the comfort of your rental. Cookware, dishware, and utensils are typically provided, ensuring that guests have everything they need for a convenient and enjoyable experience.
When is the best time to visit Weston for a holiday rental?
July is the most popular time to visit Weston, Connecticut, offering a vibrant atmosphere as families and adventure seekers flock to this charming town. The peak season runs from May through July, with visitors drawn to the area's picturesque landscapes and a variety of outdoor activities. This period is ideal for those who enjoy sunny days great for hiking, biking, and exploring the scenic parks and nature reserves nearby.

During July, you can expect pleasant weather, with temperatures typically in the mid to high 20s Celsius, creating an inviting environment for outdoor adventures and leisurely strolls through the town. The lush greenery and beautiful gardens are in full bloom, making it a wonderful time for sightseeing and enjoying the local attractions.

For those looking for a more budget-friendly option, February can be an appealing time to visit. During this time, you can still enjoy the charm of Weston without the hustle and bustle of peak season. This month often features mild winter days, allowing for peaceful walks and a chance to appreciate the serene beauty of the area.
How early should I book a Weston holiday rental?
Book your Weston holiday 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 holiday rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Can I change or cancel my Weston home rental booking on Vrbo?
To find Weston holiday 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 flat or a countryside retreat, you can turn your space into a standout destination—become a host and let Vrbo handle the heavy lifting to help you thrive.
Are all fees included in the Weston holiday 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.

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