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Fairfield holiday lettings

We found 692 holiday rentals — enter your dates for availability

Discover a selection of 54 homes and other holiday rentals in Fairfield that are perfect for your trip. Whether you're travelling with family, friends or just your furry companion, holiday rentals have the best amenities for spending time at your holiday home, such as Wi-Fi and cable TV. At the end of the day, you'll find a property to rent for everyone's needs, including a place that is accessible or non-smoking.

Holiday rentals with weekly discounts - Fairfield

Showing deals for:16 Jan - 23 Jan

Image gallery for Renovated Milford Beach home by Charles Island/Silver Sands Pk

Beach
10 out of 10, Exceptional, (6 reviews)
Exceptional
(6 reviews)

Renovated Milford Beach home by Charles Island/Silver Sands Pk

Milford, CT

8% off
Price is £1,947
for 7 nights, 1 cottage
£278 per night
includes taxes & fees
Renovated Milford Beach home by Charles Island/Silver Sands Pk

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Why visit Fairfield

  • Charming Beaches: Fairfield boasts beautiful sandy beaches perfect for relaxation and family outings.
  • Quaint Neighbourhoods: Explore vibrant local areas that showcase unique shops, cafés, and community spirit.
  • Outdoor Adventures: Enjoy various parks and outdoor activities, ideal for nature enthusiasts and families alike.
  • Cultural Experiences: Discover the rich history and culture through local attractions and events throughout the year.
  • Comfortable Accommodations: A range of delightful vacation rentals, from cottages to apartments, cater to all preferences.

Popular types of accommodation in Fairfield

Vrbo offers a delightful selection of vacation rentals in Fairfield. Whether you're seeking a charming studio apartment, a spacious bedroom apartment, or a cosy holiday cottage, we have something to suit every traveller. Our popular Fairfield cottages provide a perfect blend of comfort and charm, ensuring a memorable getaway. Discover the ideal accommodation for your next adventure, tailored to your needs and preferences.

  • Houses: The top choice for visitors to Fairfield, offering spacious and comfortable settings for families or groups.
  • Apartments: A popular option, perfect for those seeking a home-like atmosphere with convenient amenities.
  • Cottages: Quaint and inviting, these provide a charming escape for a peaceful retreat.
  • Condos: A desirable option, combining modern comforts with shared facilities for a community feel.
  • Villas: Luxurious and spacious, ideal for those looking for an upscale experience during their stay.**

Top attractions in and around Fairfield

Fairfield, Connecticut, offers a delightful blend of city life and outdoor experiences, making it ideal for cultural getaways. Visitors can explore beautiful beaches, urban parks, and modern colleges and universities. Whether travelling with family or friends, Fairfield's attractions promise enriching experiences in a charming setting, perfect for creating lasting memories.

  • Fairfield University: A vibrant institution with a modern campus, offering a lively atmosphere. Explore its beautiful grounds and engage with the local student community, enjoying a taste of collegiate life.
  • Jennings Beach: A picturesque beach perfect for relaxation and recreation, featuring soft sands and stunning views. It’s an ideal spot for sunbathing, picnicking, or a leisurely stroll along the shore.
  • Total Mortgage Arena: A buzzing entertainment venue located 2.5km away, hosting concerts and sports events. It’s a family-friendly place where you can enjoy a variety of shows and activities.

Things to do recommended for couples

For a romantic getaway in Fairfield, enjoy an evening at Levitt Pavilion for live music, embrace adventure at Waterski Connecticut, or indulge in wine tasting at Harmony Vineyards. Each experience offers a unique atmosphere perfect for couples looking to create lasting memories together.

Things to do recommended for families

During your family holiday in Fairfield, you can enjoy the lively atmosphere at Hartford HealthCare Amphitheater, unwind at Seaside Park, or explore the wonders of the Rolnick Observatory, all within 2.5km. These activities offer a perfect blend of entertainment, relaxation, and family fun.

Things to do recommended for groups

Groups visiting Fairfield can enjoy a round of golf at the beautiful Fairchild Wheeler Golf Course or the Pine Creek Par 3 Golf Course, both offering splendid outdoor settings. Additionally, the Fairfield Theater Company provides a delightful cultural experience with family-friendly performances.

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

If you're travelling with a group, family, pets, or planning an extended stay, it's important to filter your options according to your priorities. Here are some helpful booking tips for using Vrbo.

  • Traveling to Fairfield with a group: Think about how many bedrooms you require, as well as features like a fully equipped kitchen or outdoor areas for socialising. Thankfully, you can easily filter for these options and much more on Vrbo.
  • Traveling to Fairfield with young kids: Travelling with young children can present its challenges. It's important to prioritise their comfort and safety, alongside ensuring access to suitable amenities like a private swimming pool. Additionally, it's wise to think about how close you are to attractions that cater to families.
  • Taking your pets with you to Fairfield: For many, a family holiday wouldn’t be the same without their furry companion. If this resonates with you, take a look at Vrbo accommodations that welcome pets. Most of these pet-friendly properties offer feeding bowls and beds, ensuring that every member of the family feels comfortable and at home.
  • Planning for a long term stay visiting Fairfield: If you're in search of holiday rentals with great offers 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 accommodations. Don't forget to include options like a parking space, a well-equipped kitchen, or a private pool in your search as well.

Where to stay near Fairfield

Fairfield, Connecticut, offers a delightful blend of city charm and outdoor adventure, making it an ideal destination for families and couples alike. Explore the picturesque cottages nearby or indulge in a romantic getaway amidst the friendly atmosphere. With its sunny weather and welcoming locals, Fairfield is perfect for those seeking both cultural experiences and a relaxing rural escape. Don't miss the vibrant neighbourhoods and attractions that showcase the best of this lovely region.

  • Stamford: Located 9.9km from Fairfield, Stamford is a vibrant city that offers a delightful blend of urban experiences and outdoor activities. Visitors are drawn to its bustling shopping areas and dynamic theatre scene. The city’s attractions include the modern square and tourist precinct, where you can enjoy a range of shops and restaurants. Stamford is perfect for families seeking a day out, with ample parks and green spaces for picnics and leisure activities, making it a great spot for a city-themed adventure.
  • Bridgeport: Just 3.1km from Fairfield, Bridgeport is an inviting city known for its family-friendly atmosphere and outdoor recreational activities. The city's highlights include its beautiful beaches and a lively stadium that hosts various events. With a variety of shopping areas and educational venues, Bridgeport is an excellent destination for those looking to enjoy a mix of relaxation and entertainment. Families will particularly appreciate the access to lovely beaches, perfect for a sunny day by the water.
  • Norwalk: Situated 5.0km away from Fairfield, Norwalk is a charming city that attracts visitors with its combination of outdoor activities and cultural experiences. Known for its family beaches and historic sites, Norwalk offers a great selection of shopping and educational opportunities. Whether you're interested in exploring its scenic coastline or visiting its ski areas, Norwalk promises a delightful experience for tourists seeking adventure and a taste of local history.

Booking with Vrbo is a breeze

Are you keen to make the most of your budget on your next getaway? Being flexible with your travel dates can lead to considerable savings, as prices often fluctuate. Additionally, opting for a longer stay can unlock even greater discounts. To discover a Vrbo property that suits your financial plans, simply utilise our filters to organise your search by price, location, and type of holiday rental.

Vrbo Trips: Planning made easy

Vrbo's Trip Board provides a convenient area for you to plan new getaways, refine your existing arrangements, or manage your reservations. The properties you've either saved or booked are now neatly categorised into Potential, Upcoming, or Current Trips. To discover the Trip Boards, please visit: https://www.vrbo.com/en-gb/trips.

**Based on Vrbo properties bookings.

Why people love visiting friendly Fairfield

The beaches and surrounding scenery provide a peaceful ambience to your holiday home in Fairfield. Revered for its university setting, restaurants and shopping, this city is both welcoming and romantic. Whether you're planning a family holiday, romantic stay or trip with friends, holiday rentals offer features like full kitchens and laundry facilities for a more convenient stay.

Activities and attractions in and around Fairfield

Do you want to find attractions to visit while you're in the area? Although it can be tempting to stay in your comfortable holiday rental, you'll want to experience everything that makes Fairfield a one-of-a-kind holiday spot. Here are some of the top attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • Beardsley Zoo (6.4 mi / 10.3 km)
  • Norwalk Maritime Aquarium (8.6 mi / 13.8 km)
  • Great River Golf Club (13.1 mi / 21.1 km)
  • Chelsea Piers (14.5 mi / 23.4 km)
  • Del Vino Vineyards (16.1 mi / 25.9 km)
  • Country Club of Fairfield (1.1 mi / 1.8 km)

Exploring the natural landscape of Fairfield

Whether you're an outdoor enthusiast or just want to spend some time taking in the scenery, Fairfield is a great place to spend some time outside. Here are a few of the area's most eye-catching features, all within 30 miles (48.2 km) of the city centre:

  • Penfield Beach (1.2 mi / 1.9 km)
  • Fairfield Beach (1.2 mi / 1.9 km)
  • Jennings Beach (1.3 mi / 2 km)
  • Southport Beach (2.2 mi / 3.5 km)
  • Seaside Beach (3.3 mi / 5.3 km)
  • Seaside Park (3.6 mi / 5.8 km)

Seasonal weather averages in Fairfield

If warm-weather activities are high on your list, July, August, June and September are the hottest months to visit, when temperatures average 22°C.

Transport to and around Fairfield

The nearest airport is in Bridgeport, CT (BDR-Igor I. Sikorsky Memorial), located 6.9 mi (11.1 km) from the city centre. If you can't find a flight that works for your travel itinerary, you might consider flying into Danbury, CT (DXR-Danbury Municipal), which is 19.8 mi (31.9 km) away.

If you're travelling by train, make your way to Fairfield Station or Fairfield Metro Station and explore the city from there.

Frequently asked questions

What is the best area to stay in Fairfield when booking a holiday rental?
When considering a holiday rental in Fairfield, Connecticut, the best area to stay in is the Greenfield Hill neighbourhood. This charming area is known for its picturesque landscapes and historic homes, providing a tranquil retreat while still being close to local attractions. One of the highlights of Greenfield Hill is the picturesque Greenfield Hill Church, a beautiful landmark that adds to the area's charm. Additionally, the nearby Fairfield Museum and History Centre offers a fascinating insight into the local history and culture, making it a great spot for those interested in learning more about the region.

Another excellent option is the Southport neighbourhood, which is located along the coast and boasts stunning waterfront views. This quaint area is home to Southport Beach, a lovely spot for relaxation and enjoying the scenic beauty of Long Island Sound. The charming village atmosphere of Southport is great for leisurely strolls, and you'll find delightful shops and eateries that add to the overall experience.

For those interested in a more vibrant atmosphere, the downtown Fairfield area provides a great mix of restaurants, shops, and entertainment options. Here, you can explore the local culinary scene or enjoy a performance at one of the nearby theatres. The downtown area features a relatively high number of rental properties, suiting various preferences and budgets.
How much does it cost to rent a holiday home in Fairfield?
Prices for holiday rentals in Fairfield 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 Fairfield 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 Fairfield holiday house rentals?
You can find great discounts on house rentals in Fairfield 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 Fairfield?
For renting a beach house in Fairfield, Connecticut, the area around the Penfield Beach and Fairfield Beach offers excellent options. These neighbourhoods provide a picturesque coastal setting with easy access to sandy shores and stunning views of Long Island Sound. Many beach houses in this vicinity feature amenities such as private decks, outdoor seating areas, and fully equipped kitchens, great for families or groups looking to enjoy a relaxing seaside getaway.

Additionally, the nearby Southport area, known for its charming village atmosphere, has waterfront properties that often include gardens, patios, and sometimes even direct beach access. Guests can enjoy leisurely strolls along the coast or partake in local dining options, which add to the overall appeal of the area.
What is the most popular type of holiday rental accomodation in Fairfield?
In Fairfield, holiday houses are the most popular type of rental, with around 39 available throughout the area. These homes are typically situated in family-friendly neighbourhoods, providing a spacious environment great for gatherings. Most of these houses come equipped with multiple bedrooms, fully furnished kitchens, and comfortable living spaces, making them ideal for families or groups. Additionally, several cottages, apartments, and condos are also available, offering diverse options for travellers. Cottages generally provide a quaint, homely atmosphere, while apartments and condos typically feature modern amenities such as Wi-Fi and laundry facilities.
Are there any family house rentals in Fairfield?
In Fairfield, Connecticut, there are numerous family-friendly house rentals available, with around 37 options to choose from. The town is known for its welcoming atmosphere and proximity to various attractions, making it an excellent choice for families. Many of these homes feature spacious living areas, fully equipped kitchens, and outdoor spaces for children to play.

Visitors can find properties in neighbourhoods like Southport and the Beach area, which provide easy access to local parks, such as Jennings Beach and Lake Mohegan, great for day outings. These rentals often come equipped with modern amenities, including Wi-Fi and air conditioning, ensuring a comfortable stay.
Can I rent a holiday home with a pool or hot tub in Fairfield?
In Fairfield, Connecticut, there are several holiday homes available for rent that come with pools or hot tubs, with around 11 options to choose from. This charming town, located along the coastline, offers a variety of neighbourhoods where these properties can be found, including the picturesque beachfront areas and the more tranquil residential districts.
Can I find long-stay holiday rentals in Fairfield?
A long-stay holiday rental in Fairfield 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 Fairfield?
Fairfield, Connecticut, offers a variety of pet-friendly house rentals, with approximately 27 options available for travellers. Many of these properties are situated in charming residential neighbourhoods, providing an inviting space for both guests and their furry friends. Amenities commonly found in these rentals include spacious backyards, modern kitchens, and comfortable living areas, superb for families or groups looking to enjoy a home-like experience during their stay.
Are there any remote work holiday rentals in Fairfield?
In Fairfield, Connecticut, there is a robust selection of remote work holiday rentals, with approximately 47 options available. This charming coastal town is well-suited for those looking to blend work and leisure, providing a variety of comfortable accommodations that cater to remote workers. Many properties come equipped with essential amenities such as high-speed Wi-Fi, dedicated workspace areas with desks and ergonomic chairs, and sometimes even additional features like computer monitors and safe storage for valuables. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Fairfield holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in Fairfield 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 Fairfield?
In Fairfield, popular rental amenities typically include kitchens equipped with essential appliances such as microwaves and dishwashers. Many properties also provide cookware, dishware, and utensils, allowing guests to prepare their own meals during their stay. Additionally, coffee makers are commonly found in the rentals, great for enjoying a morning brew before heading out to explore local attractions like the scenic beaches or the vibrant downtown area.
When is the best time to visit Fairfield for a holiday rental?
The most popular time to visit Fairfield for a holiday rental is during the peak season from July to September. This vibrant period draws families and beachgoers eager to soak up the summer sun along the picturesque coastline. Visitors can enjoy a variety of outdoor activities, including swimming, sailing, and exploring the scenic parks, all while experiencing the lively atmosphere that Fairfield has to offer.

July, in particular, stands out as the height of the summer season, with warm temperatures averaging in the high 20s Celsius. This month is superb for those looking to engage in beach activities or partake in local events, such as the famous Fairfield Museum's summer programming, which adds a cultural touch to your holiday.

If you're considering a visit during a more budget-friendly time, November is an excellent option. While it's outside the main tourist season, you can relish the serene beauty of Fairfield, with fewer crowds and the opportunity to enjoy the charming local cafés and shops at a more leisurely pace.
How early should I book a Fairfield holiday rental?
Book your Fairfield 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.
What are the top attractions in Fairfield?
In Fairfield, Connecticut, visitors can enjoy a variety of attractions spread throughout its charming neighbourhoods. The town's historic district offers a glimpse into its rich heritage, featuring beautiful historic architecture and the Fairfield Museum and History Centre, which showcases local history and art.

For outdoor enthusiasts, the beaches along the Long Island Sound, particularly Jennings Beach and Penfield Beach, are popular spots for sunbathing, swimming, and picnicking during the warmer months. The picturesque Fairfield Beachfront area provides a relaxing atmosphere with nearby parks for leisurely strolls.

In the Greenfield Hill neighbourhood, visitors can explore the scenic landscapes and enjoy the tranquillity of the area's nature trails. Additionally, the Fairfield University campus is home to top art collections and cultural events, making it a point of interest for those looking to engage with local arts.
Can I change or cancel my Fairfield home rental booking on Vrbo?
To find Fairfield 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 Fairfield 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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