Fairfield holiday homes

We found 702 holiday rentals — enter your dates for availability
Discover a selection of 49 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:18 Dec - 25 Dec

Stairs leading to third floor
View of back of house
Kitchen
Living room
Exceptional
(7 reviews)

Fairfield Beach Modern Colonial

Fairfield

8% off
NZ$15,257
for 7 nights, 1 home
NZ$2,180 per night
includes taxes & fees
Fairfield Beach Modern Colonial
Dining
Outdoor dining
Interior
Property grounds
Exceptional
(5 reviews)

On the Water Spacious Comfortable Historic Home

West Haven

8% off
NZ$12,183
for 7 nights, 1 home
NZ$1,740 per night
includes taxes & fees
On the Water Spacious Comfortable Historic Home
Property grounds
Terrace/patio
Interior
Pool
Exceptional
(5 reviews)

Lake house cozy to relax with a family. 6 bedroom very spacious house.

Trumbull

8% off
NZ$17,843
for 7 nights, 1 home
NZ$2,549 per night
includes taxes & fees
Lake house cozy to relax with a family. 6 bedroom very spacious house.
Room
Living area
Pool
Terrace/patio
Exceptional
(5 reviews)

2 Beautiful Homes, 1 Stunning Retreat: Pool HotTub Pizza Oven + Near Beach & NYC

Fairfield

8% off
NZ$37,624
for 7 nights, 1 home
NZ$5,375 per night
includes taxes & fees
2 Beautiful Homes, 1 Stunning Retreat: Pool HotTub Pizza Oven + Near Beach & NYC
Large comfortable sectional with a 70" smart tv
Enjoy lounging after a long beach day on the sectional looking out at the water
Exterior
Fully stocked kitchen with stainless steel appliances and breakfast counter
Exceptional
(10 reviews)

Luxury Beach Oasis with Amazing Panoramic Ocean Views

Milford

8% off
NZ$11,423
for 7 nights, 1 home
NZ$1,632 per night
includes taxes & fees
Luxury Beach Oasis with Amazing Panoramic Ocean Views
Living area
Living area
Interior
Private kitchen
Exceptional
(11 reviews)

Renovated Milford Beach home by Charles Island/Silver Sands Pk

Milford

8% off
NZ$5,030
for 7 nights, 1 cottage
NZ$719 per night
includes taxes & fees
Renovated Milford Beach home by Charles Island/Silver Sands Pk
Living area
Outdoor dining
Kitchen
Living area
Exceptional
(8 reviews)

Silver Sands Beach Getaway

Milford

16% off
NZ$5,538
for 7 nights, 1 home
NZ$791 per night
includes taxes & fees
Silver Sands Beach Getaway
Living area
Marina
Interior
Outdoor dining
Wonderful
(16 reviews)

<br>❤️High-Line Harbor Flat 2 BD | Train🚊 | Harbor Point Access | 40 Minutes to NYC🗽

Stamford

7% off
NZ$2,408
for 7 nights, 1 apartment
NZ$344 per night
includes taxes & fees
<br>❤️High-Line Harbor Flat 2 BD | Train🚊 | Harbor Point Access | 40 Minutes to NYC🗽
Kitchen
Stairwell to Master
Dining Room
Queen Bedroom 2
Excellent
(6 reviews)

Beach Apartment in Woodmont Milford

Milford

8% off
NZ$3,935
for 7 nights, 1 apartment
NZ$562 per night
includes taxes & fees
Beach Apartment in Woodmont Milford
Living area
Living area
Dining
Room
Very good
(13 reviews)

❤️High-Line Harbor Pad 2 BDTrain🚊Harbor Point Access 40 Minutes to NYC

Stamford

7% off
NZ$2,451
for 7 nights, 1 apartment
NZ$350 per night
includes taxes & fees
❤️High-Line Harbor Pad 2 BDTrain🚊Harbor Point Access 40 Minutes to NYC
Interior
Interior
Room
Private kitchen
Exceptional
(10 reviews)

The Season’s Luxe One Bedroom Apartment, Center of Stamford, Train2NYC

Stamford

5% off
NZ$1,777
for 7 nights, 1 apartment
NZ$254 per night
includes taxes & fees
The Season’s Luxe One Bedroom Apartment, Center of Stamford, Train2NYC

  • Peace of mind

    Our Book with Confidence guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

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)
  • 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)
  • Connecticut Golf Club (9.3 mi / 14.9 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)
  • Seaside Beach (3.3 mi / 5.3 km)
  • Seaside Park (3.6 mi / 5.8 km)
  • Lake Mohegan (4.7 mi / 7.6 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

Where are the best areas for renting a beach house in Fairfield?
For renting a beach house in Fairfield, the area along the Long Island Sound is particularly appealing. The beachfront neighbourhoods, such as Southport and Fairfield Beach, offer a selection of charming properties with easy access to sandy shores and picturesque views of the water. Many of the rentals in these areas come equipped with amenities like private decks, outdoor dining spaces, and beach gear, making them superb for families or groups looking to enjoy coastal living.In Southport, you can find lovely cottages and larger homes located among trees, often featuring well-appointed kitchens and spacious living areas, ideal for relaxing after a day at the beach. The beach here is known for its calm waters, making it suitable for swimming and water sports. Additionally, the proximity to local shops, cafes, and restaurants enhances the convenience for visitors.Fairfield Beach itself boasts a vibrant community atmosphere, where you can find amenities such as outdoor showers for rinsing off after the beach, as well as easy access to nearby parks and recreational areas. The area is also great for those looking to enjoy activities like kayaking or paddleboarding.
What is the most popular type of holiday rental accomodation in Fairfield?
In Fairfield, holiday houses are the most prevalent type of holiday rental, with around 140 available in various neighbourhoods. These spacious homes often come with multiple bedrooms, fully equipped kitchens, and outdoor spaces such as gardens or patios, making them great for families or larger groups. Additionally, there are about 28 apartments and 24 cottages, providing more intimate accommodations for those looking for a cozier stay. Some condominiums are also available, offering modern amenities and convenient locations.
Are there any family house rentals in Fairfield?
In Fairfield, Connecticut, families can choose from a variety of holiday rentals—approximately 30 options are available throughout the area. The town is well-situated near beautiful beaches and parks, making it an ideal destination for those travelling with children. Many properties feature spacious living areas, fully equipped kitchens for preparing family meals, and outdoor spaces where kids can enjoy themselves.Visitors will find accommodations that typically include amenities such as Wi-Fi, air conditioning, and laundry facilities, ensuring a comfortable stay. Notable nearby attractions include the scenic Fairfield Beach, which offers opportunities for swimming and picnicking, as well as the expansive Lake Mohegan, great for hiking and outdoor activities.
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 feature pools and hot tubs, making it a delightful choice for those seeking relaxation and luxury. This charming coastal town offers a mix of residential neighbourhoods, including the picturesque Southport area, known for its scenic beaches and quaint shops, as well as the more suburban settings found throughout Fairfield.Travellers can expect amenities such as private pools, inviting hot tubs, spacious outdoor living areas, and fully equipped kitchens great for family gatherings. Many properties also offer additional comforts like Wi-Fi, air conditioning, and proximity to local attractions, ensuring a comfortable stay.
Are there pet-friendly house rentals in Fairfield?
In Fairfield, Connecticut, there are several pet-friendly house rentals available, providing a welcoming environment for travellers with pets. Many of these properties come equipped with modern amenities such as spacious kitchens, private gardens, and comfortable living areas, making them ideal for families or groups.The neighbourhood features easy access to local parks, such as Jennings Beach and Lake Mohegan, which are superb spots for walking pets and enjoying the outdoors. Jennings Beach offers sandy shores and scenic views, while Lake Mohegan has hiking trails and picnic areas, allowing for enjoyable outings with your furry companions.Additionally, the area is known for its charming downtown, where visitors can find pet-friendly cafes and shops, enhancing the overall experience for those travelling with their pets.
Are there any remote work holiday rentals in Fairfield?
In Fairfield, Connecticut, there are numerous remote work holiday rentals available, with around 192 options to choose from. This charming coastal town offers a variety of properties that cater to remote workers, featuring essential amenities such as high-speed Wi-Fi, comfortable office spaces, and the convenience of fully equipped kitchens for those who prefer to prepare their own meals. Many rentals also provide outdoor areas where you can take breaks and enjoy the pleasant surroundings.The town's location offers easy access to local parks, scenic beaches, and cultural attractions, making it an ideal spot for balancing work and leisure. With a mix of modern apartments and traditional homes, travellers can find accommodations that suit their style and needs. To help narrow your search, insert your dates and apply the "WiFi" filter on Bookabach.
What are popular rental amenities in Fairfield?
In Fairfield, popular holiday rental amenities typically include kitchens, allowing guests to prepare their own meals, and outdoor spaces such as decks or patios for enjoying the pleasant Connecticut weather. Many rentals also come equipped with coffee and tea makers for convenient morning brews, and onsite parking is commonly available, making it easier for travellers with vehicles.
When is the best time to visit Fairfield for a holiday rental?
July is the most popular time to visit Fairfield, Connecticut, attracting families and beach enthusiasts eager to enjoy the summer sun. This peak season, spanning from July to September, offers a vibrant setting with plenty of outdoor activities, including sunbathing on the sandy beaches, picnicking in serene parks, and exploring the picturesque seaside.During July, visitors can expect warm temperatures averaging around 25 to 30 degrees Celsius, creating an inviting environment for leisurely strolls along the coastline or engaging in water sports. The town comes alive with various events, and families often flock to its charming beaches, making it a lively and enjoyable destination.If you're looking for a more budget-friendly option, consider visiting in November. While this month is outside the high tourist season, it brings a unique charm to Fairfield. You can enjoy a quieter experience, great for unwinding and discovering local shops and eateries without the summer crowds.
What are the top attractions in Fairfield?
In Fairfield, Connecticut, visitors can enjoy a variety of attractions that showcase the charm of this coastal town. The Fairfield Museum and History Centre offers insights into the local heritage and hosts engaging exhibits throughout the year. Nearby, the scenic Jennings Beach provides a lovely spot for sunbathing, picnicking, and enjoying the waterfront, with playgrounds and walking paths for families. The historic town centre features a mix of local shops, cafes, and restaurants, making it a pleasant area to explore on foot.For nature lovers, the nearby Southport Beach is another great option, providing beautiful views and opportunities for leisurely strolls along the shore. Additionally, the Fairfield Theatre Company presents a vibrant arts scene, hosting live performances that attract both locals and visitors.
Are all fees included in the Fairfield holiday homes prices shown on Bookabach?
Bookabach 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.
Are there any Fairfield holiday homes with parking?
Bookabach offers a wide selection of holiday homes 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 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.
Are there any discounts for Fairfield holiday homes?
You can find great discounts on holiday homes in Fairfield on Bookabach, 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.
Can I change or cancel my Fairfield holiday home booking on Bookabach?
To find Fairfield holiday rentals with free cancellation, just use Bookabach'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". Whether you're adjusting your plans or looking for flexible payment options, Bookabach makes it easy to book with confidence.
Can I find long-stay holiday homes in Fairfield?
A long-stay holiday home 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 vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Bookabach?
Bookabach's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favourites, and build the perfect itinerary together.
How early should I book a Fairfield holiday home?
Book your Fairfield holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Bookabach booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Fairfield?
Prices for holiday homes 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 travelling solo, as a couple, with family, or in a group. Bookabach offers something for every taste and budget, from affordable homes in Fairfield to more spacious homes.
What can I expect from Bookabach customer service and Bookabach Care™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, Bookabach Care™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Bookabach customer service is available 24/7 to support you every step of the way. Bookabach also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is Bookabach Care™ and how does it work?
Bookabach's mission is to help guests relax, reconnect, and enjoy precious time together. With Bookabach Care™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
Why should I join Bookabach as a host?
Joining Bookabach 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, Bookabach makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Bookabach handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

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