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

Scandinavian Designer 2 Bed Cabin In The Woods - Fairfield, CT
10 57 reviews

Scandinavian Designer 2 Bed Cabin In The Woods

cabin, Easton
This designer lodge is situated in the woods, just a short drive from Westport and a 20-minute journey to beaches, shops and supermarkets in Easton. The property has received excellent ratings for cleanliness, location and overall user experience.
The two-bedroom lodge can accommodate up to four guests and features a modern interior with a fully equipped kitchen, a wood-burning fireplace and a large outdoor deck. Enjoy the panoramic views of the surrounding woodland, relax in the hammock by the fire pit or take advantage of the on-site generator for peace of mind.
Zen, Spacious & Comfy, Lux Beds - Fairfield, CT
9.8 39 reviews

Zen, Spacious & Comfy, Lux Beds

apartment, Bridgeport
This basement flat is situated in a peaceful neighbourhood just 2 kilometres from Bridgeport's two main hospitals, Sacred Heart and Bridgeport Hospital, making it easy to access the city centre. It has received excellent ratings for cleanliness, location, and user experience.
The two-bedroom flat comfortably accommodates up to four guests and comes equipped with a well-stocked kitchen, a washing machine and dryer, a large yard with a swing, and high-speed internet. Enjoy the peace and quiet of this comfortable flat with its memory foam beds and entertainment system.
Modern Beach Bungalow - Fairfield, CT
9.9 78 reviews

Modern Beach Bungalow

apartment, Fairfield
This modern house in Fairfield is just a short walk from the beach, offering easy access to the sand and the serene Long Island Sound. The accommodation has received excellent ratings for its location, cleanliness, and overall experience.
The house features a spacious open plan layout, comfortably accommodating up to four guests. It offers a range of amenities, including a fully equipped kitchen, air conditioning, a private garden, and a large smart TV. Guests can also enjoy the outdoor shower, beach amenities, and convenient access to nearby golf courses, hiking trails, and the town's shops and restaurants.
Stay At Black Rock Harbor - Fairfield, CT
9.9 70 reviews

Stay At Black Rock Harbor

house, Bridgeport
This apartment is in Black Rock, a short walk from the beach and downtown, making it ideal for exploring the area. It has excellent user, location and cleanliness ratings, ensuring a comfortable stay.
This home has three bedrooms and two bathrooms, comfortably accommodating up to six guests. It has a fully equipped kitchen, a backyard with a picnic table, a Tesla EV charger, and offers flexible check-in and hassle-free departure.

Best Fairfield, CT holiday rentals with a pool

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

The "Grant" Estate - Fairfield, CT
10 1 review

The "Grant" Estate

apartment, Fairfield
This five-bedroom, four-bathroom colonial house in Fairfield, Connecticut, is situated near Westport, a 16km drive from Long Island Sound beaches and surrounded by forests offering hiking, fishing, and rock climbing opportunities.
The 2-acre property boasts a heated outdoor pool, hot tub, chef's kitchen with a 4.5-metre marble island, basement gym with Peloton and Nintendo Switch, EV charging, and accommodates up to ten guests.
Large Family Home W/ Pool, Hot Tub, Sauna & Gym - Fairfield, CT
10 1 review

Large Family Home W/ Pool, Hot Tub, Sauna & Gym

apartment, Weston
This spacious house is located in Weston, just over 100km from Manhattan, offering easy access to the town centre and its amenities. It has received excellent user, location and cleanliness ratings, ensuring a comfortable and enjoyable stay.
The property has four bedrooms and five bathrooms, comfortably accommodating up to four guests. The house features a range of amenities, including a swimming pool, jacuzzi, sauna, fitness centre, and a fully equipped kitchen, perfect for both relaxation and entertainment.
House ∙ 3 Bedrooms ∙ 6 Guests - Fairfield, CT
No reviews

House ∙ 3 Bedrooms ∙ 6 Guests

house, Fairfield
This beachfront property is located in Fairfield's Pine Creek district, offering direct access to the Long Island Sound and is a short drive from downtown Fairfield's amenities.
This three-storey residence accommodates six guests with three bedrooms and four bathrooms, featuring a private hot tub, kayaks, and paddleboards, and is close to the Pine Creek recreation area.
Home In Fairfield - Fairfield, CT
9.8 13 reviews

Home In Fairfield

apartment, Fairfield
This modern house is located in Fairfield, just a short distance from the town centre and a kilometre from the freeway exit and Metro North station. The area is quiet and residential, with easy access to shops, restaurants and amenities.
This five-bedroom property can comfortably accommodate up to ten guests. The house includes a fully equipped kitchen, a spacious living area, a private garden and a swimming pool. Guests can enjoy a range of amenities, including a fitness centre, a games room, a barbecue area and a mudroom with direct access to the pool.

Frequently asked questions about holiday rentals in Fairfield, CT

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

    Fairfield boasts a lovely coastline, so a visit to Jennings Beach or Lake Mohegan is a must. The historic Fairfield Museum and History Center offers a fascinating glimpse into the town's past. For architecture buffs, a stroll through the charming downtown area, admiring the historic buildings, is recommended.
  • 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's location on Long Island Sound provides stunning coastal views and diverse wildlife. While there aren't unique geological phenomena like geysers, the tidal marshes and beaches offer a rich ecosystem to explore. Look out for migratory birds during certain seasons.
  • What are the most popular Airbnbs in Fairfield, CT?

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

    Comfortable walking shoes are a must, as you'll likely be doing a fair bit of exploring on foot. Sunscreen and a hat are crucial, especially during the summer months. Depending on the time of year, a light jacket or raincoat might also be useful. Don't forget your 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 doesn't host huge, internationally renowned festivals. However, the town often has smaller, local events throughout the year. Check the Fairfield Parks and Recreation Department's website for details on local events and concerts in the summer months. The annual Memorial Day parade is a community highlight.
  • What are the best rentals for families and kids in Fairfield, CT?

  • What is the average daily budget you should plan for (accommodation, food, transportation, activities) in Fairfield, Connecticut?

    A daily budget of £150-£300 per person should be sufficient, depending on your accommodation choices and dining preferences. This estimate includes mid-range accommodation, meals at a mix of restaurants and cafes, local transport, and entry fees to attractions. Budget travellers could manage on less, while luxury travellers would need more.
  • What are the best rentals or Airbnbs with a jacuzzi 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 varied culinary scene. For fresh seafood, try The Black Bear Saloon or another restaurant along the coast. There are also numerous Italian restaurants reflecting the area's heritage. There isn't one specific 'must-try' Fairfield specialty, but exploring the different cuisines available is part of the experience.
  • What are some less-famous attractions in Fairfield, Connecticut that are worth a visit?

    The Pequotsepos Nature Center offers beautiful walking trails and opportunities for wildlife spotting. Exploring the various smaller parks scattered throughout the town provides a quieter alternative to the more popular beaches. A walk along the Fairfield Beach Road offers beautiful views of the Long Island Sound.
  • What are the best activities for engaging with locals and understanding their culture in Fairfield, Connecticut?

    Visiting local farmers' markets is a great way to interact with residents and sample local produce. Attending a community event, like a concert in a local park, provides opportunities for casual interaction. Simply striking up conversations with people in local shops and cafes can offer insights into the community.
  • What unique natural landscapes and terrain features can travellers explore in Fairfield, Connecticut?

    Fairfield's landscape is primarily coastal, with beaches, tidal marshes, and relatively flat terrain. The coastline offers diverse habitats, from sandy beaches to rocky outcrops. The Pequotsepos Nature Center provides a glimpse into the area's natural environment.
  • How many days are ideal for a visit to Fairfield, Connecticut, and what are some itinerary suggestions?

    Two to three days is a good amount of time to explore Fairfield. A possible itinerary could include a day exploring the beaches and coastline, a day visiting the Fairfield Museum and History Center and downtown, and a day at the Pequotsepos Nature Center or exploring other local parks.

Nearby regions

Best Fairfield, CT holiday rentals with a balcony

Fairfield Cottage -Top Rated Gem, Fire Pit, Near Beach, 90 Min To Nyc - Fairfield, CT
9.3 4 reviews

Fairfield Cottage -Top Rated Gem, Fire Pit, Near Beach, 90 Min To Nyc

house, Fairfield
This charming cottage is located in Fairfield, just 18 kilometres from Silver Sands State Park, 22 kilometres from Connecticut Post Mall Shopping Centre, and 32 kilometres from The Yale Bowl, offering a peaceful retreat away from the hustle and bustle. It has consistently received excellent ratings for location, cleanliness, and overall user experience.
The cottage features three bedrooms and one bathroom, spanning 130 square metres and comfortably accommodating up to six guests. It boasts a fully equipped kitchen, private patio, air conditioning, complimentary Wi-Fi, and private parking, along with a garden and outdoor play equipment for families.
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.
Cozy Cottage With Fire Pit, Near Beach, 1 Mile To Nyc Train - Fairfield, CT
10 39 reviews

Cozy Cottage With Fire Pit, Near Beach, 1 Mile To Nyc Train

apartment, Fairfield
This Fairfield property is situated within 5km of Fairfield University, the Bellarmine Museum of Art, Longfellow Park, Bridgeport's Downtown South Historic District, and Seaside Park, and an 18-minute walk from Fairfield Metro station.
This four-bedroom, two-bathroom house sleeps eight guests and boasts a fully equipped kitchen (fridge, microwave, dishwasher), air conditioning, a garden, parking, Wi-Fi, and an on-site games room; pets are welcome.
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.

Best Fairfield, CT holiday rentals with parking

Modern 3 Bedroom House In The Heart Of Black Rock - Fairfield, CT
9.4 29 reviews

Modern 3 Bedroom House In The Heart Of Black Rock

house, Bridgeport
Blackrock Suites is located in the Blackrock district of Bridgeport, just a short distance from beautiful beaches, museums, lighthouses, and parks. The area offers a peaceful retreat from the hustle and bustle of the city, with easy access to a variety of attractions.
The suite is a comfortable and spacious three-bedroom apartment that can accommodate up to seven guests. It features a fully equipped kitchen, laundry facilities, air conditioning, parking, and internet access, ensuring a comfortable and convenient stay.
Modern 2 Bedroom Apt In Black Rock Near The Beach - Fairfield, CT
9.3 22 reviews

Modern 2 Bedroom Apt In Black Rock Near The Beach

apartment, Bridgeport
This modern two-bedroom flat is situated in the peaceful Black Rock neighbourhood of Bridgeport, just a short distance from the city's beaches, museums, and parks. The area is known for its quiet streets and proximity to the sea, offering a tranquil escape from the city centre.
The flat is ideal for families or groups of up to four people, with a fully equipped kitchen, laundry facilities, and air conditioning. Guests can enjoy the modern design, peaceful location, and access to a variety of local restaurants and activities.
Charming Beach Apartment - Fairfield, CT
10 2 reviews

Charming Beach Apartment

apartment, Fairfield
This Fairfield apartment, recently renovated in January 2025, is centrally located within walking distance of Fairfield Beach and the town centre, and directly opposite a park with bocce, volleyball, and tennis courts.
The three-bedroom, one-bathroom flat sleeps four guests and offers amenities including parking, internet access, and air conditioning; pets are welcome.
2-bedroom Modern Apartment For Relaxing Stays - Fairfield, CT
No reviews

2-bedroom Modern Apartment For Relaxing Stays

apartment, Bridgeport
This two-bedroom flat is situated in Bridgeport's West End - West Side, offering convenient access to Silver Sands State Park and The Coastal Centre at Milford Point, with Beardsley Zoo and the Regina A. Quick Centre for the Arts also within proximity.
This accommodation for four guests boasts air conditioning, a balcony, and parking, with nearby attractions including the Hartford HealthCare Amphitheatre and Total Mortgage Arena, making it ideal for exploring local events and natural beauty.
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