Holiday Rentals in Fairfield, CT

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Fairfield, CT holiday rentals
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355 Holiday Rentals and Airbnb in Fairfield, CT

Best family friendly Fairfield, CT holiday rentals

Among the 355 accommodations in Fairfield, CT, here are the 4 best family friendly rentals

Lovely 5 Bedroom Beach House With Large Backyard - Fairfield, CT
10 11 reviews

Lovely 5 Bedroom Beach House With Large Backyard

apartment, Fairfield
This Fairfield house is situated just a short walk from the beach, the town centre, and the Metro North train station, making it a convenient base for exploring the area. The surrounding neighbourhood is quiet and residential, offering a peaceful retreat from the hustle and bustle of city life.
The house has 5 bedrooms and 3 bathrooms, providing ample space for up to 9 guests. It features a fully equipped kitchen, a spacious living room with a fireplace, a large garden with a patio, and parking for multiple vehicles.
2bdfairfield Work & Relax Space W. Patio+fast Wifi - Fairfield, CT
9.8 101 reviews

2bdfairfield Work & Relax Space W. Patio+fast Wifi

apartment, Fairfield
This two-bedroom flat is located in a peaceful residential area in Fairfield, just a short distance from the bustling town centre. The property has received excellent ratings for its cleanliness, location, and overall experience.
The apartment comfortably accommodates up to five guests and features a spacious living area, a fully equipped kitchen, and a private garden. Guests can enjoy a range of amenities including a fire pit, a picnic table, multiple patios, and a modern entertainment system.
Remodeled Cozy Country Cape - Fairfield, CT
10 40 reviews

Remodeled Cozy Country Cape

apartment, Fairfield
This Fairfield apartment is conveniently located just a short distance from the town's attractions and amenities, making it an ideal base for exploring the area. The property has received excellent ratings for its cleanliness, location, and overall experience.
The spacious apartment can comfortably accommodate up to four guests and features a modern and stylish open plan layout. Guests can enjoy a fully equipped kitchen, a private garden, and a comfortable living area with a TV, perfect for relaxing after a day of sightseeing.
Sun-filled Fairfield 3br|fam-friendly Yard+pergola - Fairfield, CT
9.9 100 reviews

Sun-filled Fairfield 3br|fam-friendly Yard+pergola

apartment, Fairfield
This newly renovated three-bedroom flat is located in a residential area of Bridgeport, just a short walk from the city centre and its many attractions. The accommodation has received excellent ratings for cleanliness, location and user experience.
This spacious property can comfortably accommodate up to seven guests and features two king-size beds and one queen-size bed. Guests can enjoy a large private yard with a barbecue, picnic table and fire pits, perfect for relaxing and entertaining.

Best Fairfield, CT holiday rentals with a pool

Among the 355 accommodations in Fairfield, CT, here are the 4 best rentals with a pool

Characterful Iconic Weston Lodge. - Fairfield, CT
No reviews

Characterful Iconic Weston Lodge.

apartment, Weston
This tranquil four-bedroom flat, offering a unique getaway experience, is located in a peaceful residential area of Weston, a short distance from the town centre and its shops and restaurants.
This spacious accommodation for six guests boasts air conditioning, a swimming pool, jacuzzi, garden, and parking, with a kitchen equipped with a fridge and dishwasher.
Spacious Cottage Loft - Fairfield, CT
10 113 reviews

Spacious Cottage Loft

apartment, Bridgeport
The Spacious Cottage Loft is located in Black Rock, a charming seaside neighbourhood in Bridgeport, Connecticut, set on the grounds of a historic Victorian house dating back to the 1840s. The cottage has received excellent ratings for location, cleanliness, and user experience, making it a popular choice for travellers.
The cottage has one bedroom and one bathroom, comfortably accommodating two guests. It offers a range of amenities including a fully equipped kitchen, two smart TVs, a dedicated workspace, a private patio, and access to a swimming pool during the warmer months.
1br Guest Apt. Suite /Full Bath, Kitchen -Pool/spa - Fairfield, CT
10 7 reviews

1br Guest Apt. Suite /Full Bath, Kitchen -Pool/spa

apartment, Weston
This Weston guesthouse is situated in a suburban area near Westport and New York City, conveniently located for exploring both locations.
The self-contained suite, sleeping up to three guests, boasts a California king bed, sleeper couch, kitchenette with fridge and microwave, private terrace, and access to a heated 15-metre gunite pool and jacuzzi on a three-acre estate.
One Of A Kind Executive Stay In Easton, Ct. - Fairfield, CT
9.4 22 reviews

One Of A Kind Executive Stay In Easton, Ct.

apartment, Easton
This Lower Easton Colonial/Contemporary home is situated in a peaceful, secluded area on 3 acres, just a short drive (around 3 km) from the bustling centre of Easton. The property has excellent user, location and cleanliness ratings.
This spacious residence offers five bedrooms and four bathrooms, comfortably accommodating up to 10 guests. Enjoy a range of amenities including a swimming pool, garden, parking, a fully equipped kitchen, air conditioning and a basement entertainment area with a theatre room, game room and bar.

Frequently asked questions about holiday rentals in Fairfield, CT

  • What are the must-see sights in Fairfield, Connecticut?

    Fairfield boasts several attractive spots. The historic Fairfield Museum and History Center offers a glimpse into the town's past. Lake Mohegan offers lovely walks and views, while the Fairfield University campus is architecturally impressive and has some beautiful green spaces. People also enjoy exploring the coastline and beaches, such as Jennings Beach and Southport Beach.
  • What are the best Airbnb and holiday rentals in Fairfield, CT?

    The Inn At Fairfield Beach, Southport - Ct Across From Beach and Cozy Home Away From Home are the most popular Airbnb and holiday rentals in Fairfield, CT among travellers.

  • Are there any unique natural phenomena in Fairfield, Connecticut?

    Fairfield doesn't have dramatic, unique natural phenomena like geysers or massive caves. However, its location on Long Island Sound provides beautiful coastal scenery, tidal changes, and diverse birdlife, particularly noticeable in the salt marshes and along the coastline. The seasonal changes are also quite striking.
  • What are the most popular Airbnbs in Fairfield, CT?

  • What essentials should you bring along to Fairfield, Connecticut?

    Pack comfortable walking shoes, as you'll likely be doing a fair bit of exploring on foot. Sunscreen and a hat are vital, especially during the summer months. Depending on the time of year, layers of clothing are advisable, as the weather can be changeable. Don't forget swimwear if you plan on visiting the beaches.
  • What are the best holiday rentals with a pool in Fairfield, CT?

  • What famous events or festivals are happening in Fairfield, Connecticut?

    Fairfield's events calendar varies throughout the year. The annual July 4th fireworks display over Long Island Sound is a popular event. Check local listings closer to your travel dates for smaller community events and festivals.
  • What are the best rentals for families and kids in Fairfield, CT?

  • Where can you find the best restaurants serving local dishes in Fairfield, Connecticut, and what are the must-try specialties?

    Fairfield has a diverse culinary scene. While there aren't specific 'Fairfield specialties', many restaurants offer fresh seafood caught locally from Long Island Sound. Consider trying some of the restaurants along the Post Road for a range of options, from casual eateries to more upscale dining experiences. Looking at online reviews will help you find places that suit your taste and budget.
  • What are the best rentals or Airbnbs with a jacuzzi in Fairfield, CT?

  • What are some less-famous attractions in Fairfield, Connecticut that are worth a visit?

    The Pequotsepos Nature Center offers a lovely escape into nature with walking trails. Exploring the various smaller parks and green spaces scattered throughout town can be a rewarding experience. Take a walk along the coastline paths away from the main beaches for a more tranquil experience.
  • What are the best activities for engaging with locals and understanding their culture in Fairfield, Connecticut?

    Attending local events and festivals is a great way to interact with residents. Visiting the Fairfield Museum and History Center can provide insight into the town's heritage. Simply striking up conversations with people in local shops or cafes can be a pleasant way to learn more about the community.
  • What unique natural landscapes and terrain features can travellers explore in Fairfield, Connecticut?

    Fairfield's landscape is characterised by its coastal location, with beaches, salt marshes, and the shoreline itself offering diverse exploration opportunities. The relatively flat terrain is punctuated by some gentle hills and the wooded areas of places like Lake Mohegan.
  • How many days are ideal for visiting Fairfield, Connecticut, and what are some itinerary suggestions?

    Two to three days is a good amount of time to explore Fairfield. One could spend a day exploring the town centre, visiting the museum and enjoying the beaches. Another day could be dedicated to exploring Lake Mohegan and the surrounding nature trails. A third day could involve further beach time or exploring nearby towns.

Nearby regions

Best Fairfield, CT holiday rentals with a balcony

90-sec Walk To Beach - Walnut Beach Luxury House - Fairfield, CT
10 1 review

90-sec Walk To Beach - Walnut Beach Luxury House

apartment, Milford
This new-build seaside flat in Milford is situated just 6 houses from the beach and close to Silver Sands State Park, offering approximately 242 square meters of living space. This property features a chef's kitchen with a quartz island and GE Profile Smart Air Fryer Oven, a spa-inspired primary suite with a balcony, a dedicated office, and a third-floor rec room with water views, accommodating up to 6 guests.
Charming Colonial For Events!  Perfect For Family Reunions And Group Getaways! - Fairfield, CT
8.8 10 reviews

Charming Colonial For Events! Perfect For Family Reunions And Group Getaways!

apartment, Bridgeport
This six-bedroom, four-bathroom house, situated in Bridgeport's Downtown South Historic District near Perry House, offers easy access to attractions such as Beardsley Zoo and the Bridgeport Bluefish Baseball Club (distances not specified).
The 3,300 sq ft (approximately 307 sq m) property sleeps 8-12 guests and includes a modern master suite with a private terrace, a den, stainless steel appliances, off-street parking for six cars, and extensive outdoor space including a half-acre lawn.
Villa Après Sea - Fairfield, CT
9.0 1 review

Villa Après Sea

house, Westport
This Westport holiday home offers exclusive private access to Compo Beach, located 27 kilometres from Silver Sands State Park and 32 kilometres from Connecticut Post Mall.
This spacious, air-conditioned detached house covers 305 square metres, accommodating up to 11 guests with four bathrooms, a fully equipped kitchen, complimentary Wi-Fi, and free private parking.
Beechmont-charming Colonial For Events And Getaways! - Fairfield, CT
8.0 1 review

Beechmont-charming Colonial For Events And Getaways!

house, Bridgeport
This Bridgeport property, a colonial-style house, is located 13.7km from Silver Sands State Park and 19.3km from the Connecticut Post Mall, offering convenient access to local attractions.
The 307 square metre dwelling boasts one bedroom, four bathrooms, and accommodates up to 23 guests, featuring a fully equipped kitchen, free Wi-Fi, private parking, and a terrace/garden.

Best Fairfield, CT holiday rentals with parking

59 Rennell St, Bridgeport · Lovely 1 Bedroom Cozy Modern Apartment W/75 4k Tv - Fairfield, CT
8.0 8 reviews

59 Rennell St, Bridgeport · Lovely 1 Bedroom Cozy Modern Apartment W/75 4k Tv

apartment, Bridgeport
This Bridgeport apartment is ideally situated near the University of Bridgeport and the Bridgeport Downtown South Historic District, within a 2.4km radius of Seaside Park and Seaside Beach, and a 1.9km walk from Bridgeport Station.
The one-bedroom flat, sleeping two guests, boasts a fully equipped kitchen with a fridge, microwave, and stovetop, a washing machine, a fireplace, a TV, and on-site parking, all within a smoke-free environment.
Sunny & Spacious 2bd 1ba Wfh Apt-huge Yard & Patio - Fairfield, CT
9.6 5 reviews

Sunny & Spacious 2bd 1ba Wfh Apt-huge Yard & Patio

apartment, Fairfield
This Fairfield apartment, situated 18km from Silver Sands State Park and 23km from the Connecticut Post Mall, offers easy access to both coastal attractions and shopping.
The 93 square metre, two-bedroom property sleeps nine guests and features a fully equipped kitchen, a garden, parking, and a fireplace; nearby Yale University and the Yale Bowl are within 32km.
Cozy, Updated Single Family In Fairfield County - Fairfield, CT
9.8 76 reviews

Cozy, Updated Single Family In Fairfield County

apartment, Trumbull
This Trumbull apartment, a short 1.6km drive from Sacred Heart University and the Merritt Parkway, offers easy access to parks, beaches, shopping, and restaurants in Fairfield County.
Sleeping seven guests, this three-bedroom, one-bathroom property features a newly renovated kitchen, spacious backyard with patio and fire pit, family room/office, and covered patio with outdoor dining; private parking is also available.
Paradise Awaits
5 Acre Estate - Sasco Hill - Fairfield, CT
10 5 reviews

Paradise Awaits 5 Acre Estate - Sasco Hill

apartment, Fairfield
This luxury estate is situated on Sasco Hill in Fairfield, just a short walk from Sasco Beach and the Long Island Sound, offering a peaceful retreat with stunning views. The property has received excellent ratings for location, cleanliness, and user experience, making it a popular choice for travellers.
The five-bedroom house comfortably sleeps up to ten guests, ideal for families or groups of friends. With an Olympic-sized swimming pool, twin cabanas, a spacious den, a martini lounge, and a dedicated children's suite, the estate provides a luxurious and comfortable stay with plenty of entertainment options.
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