Holiday Rentals in Fairfield, CT

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Fairfield, CT holiday rentals
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245 Holiday rentals and Airbnb in Fairfield, CT

Best family friendly Fairfield, CT holiday rentals

Among the 245 accommodations in Fairfield, CT, here are the 4 best family friendly rentals

Modern Beach Bungalow - Fairfield, CT
9.9 74 reviews
Fairfield, CT
29/07 – 07/08
395 €/nighttotal: 3555 € (9 )

Modern Beach Bungalow

2 2
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.
Polita’s Place #1 - Fairfield, CT
9.9 98 reviews
Fairfield, CT
23/10 – 25/10
296 €/nighttotal: 592 € (2 )

Polita’s Place #1

1 7
apartment , Bridgeport
This three-bedroom flat is conveniently located in the centre of Bridgeport, within walking distance of the Beardsley Zoo and a short drive from the Downtown Bridgeport area and the Bridgeport Art Center. It has received excellent ratings for location, cleanliness and user experience.
The flat is spacious and has a modern and coastal decor. It comes with a fully equipped kitchen, air conditioning, a garden, parking and internet access, making it perfect for a comfortable and enjoyable stay.
Lake House Cozy To Relax With A Family. 6 Bedroom Very Spacious House. - Fairfield, CT
9.6 5 reviews
Fairfield, CT
17/07 – 19/07
3185 €/nighttotal: 6370 € (2 )

Lake House Cozy To Relax With A Family. 6 Bedroom Very Spacious House.

6 12
apartment , Trumbull
This Trumbull, Connecticut holiday home is conveniently located near major highways, offering easy access to local parks such as Boothe Memorial Park and museums including the National Helicopter Museum.
The six-bedroom, four-bathroom property sleeps twelve guests and boasts amenities including a jacuzzi, garden, free WiFi, and a fully equipped kitchen with dishwasher; nearby attractions include Beardsley Zoo and the Discovery Museum.
Westport Luxury Family Retreat | Resort Pool Debut - Fairfield, CT
9.6 41 reviews
Fairfield, CT
27/06 – 04/07
961 €/nighttotal: 6727 € (7 )

Westport Luxury Family Retreat | Resort Pool Debut

3 2
apartment , Westport
This stylish three-bedroom home is located on a charming New England street in Westport, just a short distance from both the beautiful Compo Beach and the vibrant downtown area. The property has received excellent ratings for location, cleanliness, and overall user experience.
The apartment is spacious and comfortable, with a large eat-in kitchen, a comfy family room, and a sunken patio. It can accommodate up to five guests and offers a fully equipped kitchen, a private home gym, a family-friendly yard, and convenient amenities like a laundry room and a two-car garage.

Best Fairfield, CT holiday rentals with a pool

Among the 245 accommodations in Fairfield, CT, here are the 4 best rentals with a pool

Summer Estate Close To Ny, Nj, Ma W Heated Pool Sleeps 16+ - Fairfield, CT
10 73 reviews
Fairfield, CT
06/08 – 09/08
3154 €/nighttotal: 9462 € (3 )

Summer Estate Close To Ny, Nj, Ma W Heated Pool Sleeps 16+

1 5
apartment , Fairfield
This spacious apartment is situated on a secluded two-acre property in the countryside of Fairfield, Connecticut, offering peace and privacy away from the town centre. It has received excellent ratings for its location, cleanliness, and overall user experience.
The apartment spans 465 square metres and comfortably accommodates up to 16 guests. It boasts a range of amenities including a private pool and pool house, a fitness centre with a Peloton bike and treadmill, and a fully equipped kitchen.
Victorian Apartment - Fairfield, CT
9.8 74 reviews
Fairfield, CT
29/07 – 07/08
169 €/nighttotal: 1521 € (9 )

Victorian Apartment

1 2
apartment , Bridgeport
This one-bedroom apartment is situated in the historic Black Rock neighbourhood of Bridgeport, a short walk from the Fairfield Metro Train Station and minutes from the I-95 highway, offering easy access to both the city and the surrounding area. The property has excellent ratings for location, cleanliness, and user experience.
The downstairs flat has a separate entrance and can accommodate up to two guests. It features a private washer and dryer, two smart TVs, strong Wi-Fi, and a spacious living area. There is a shared swimming pool available during the summer months, as well as a private patio, a barbecue, and a large garden.
Westport Summer Retreat: Available 6/21-7/6 - Fairfield, CT
Fairfield, CT
27/06 – 04/07
1727 €/nighttotal: 12089 € (7 )

Westport Summer Retreat: Available 6/21-7/6

6 2
apartment , Westport
This six-bedroom, five-bathroom residence in Westport offers a prime location, situated conveniently within 1 kilometre of the town centre, the beach, and the train station.
This spacious property accommodates up to 12 guests and features a saltwater swimming pool, jacuzzi, two offices, and a recreation room with a gym and wine cellar, perfect for a relaxing holiday.
Designer Villa Bordering  Westport - Fairfield, CT
9.9 18 reviews
Fairfield, CT
17/08 – 31/08
1024 €/nighttotal: 14336 € (14 )

Designer Villa Bordering Westport

1 2
house , Fairfield
This designer cottage is situated in a tranquil setting near Westport, just minutes from the beach, the town centre, the historic sailing town of Southport, and the train station. The property has received excellent ratings for its location, cleanliness, and overall experience.
This spacious house offers four bedrooms and four bathrooms, accommodating up to six guests. Guests can enjoy a range of amenities, including a heated pool, hot tub, two kitchens, multiple living spaces, a game room, a fire pit, and a bocci court.

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

Charming Colonial For Events!  Perfect For Family Reunions And Group Getaways! - Fairfield, CT
8.8 10 reviews
Fairfield, CT
16/08 – 28/08
940 €/nighttotal: 11280 € (12 )

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

6 2
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.
Grand Fairfield Getaway- 5br Fam-friendly Near I95&shops - Spacious&gracious - Fairfield, CT
9.4 20 reviews
Fairfield, CT
19/12 – 02/01
868 €/nighttotal: 12152 € (14 )

Grand Fairfield Getaway- 5br Fam-friendly Near I95&shops - Spacious&gracious

5 4
apartment , Fairfield
This Fairfield house is conveniently located within 3km of Fairfield University, Bridgeport Downtown South Historic District, and Longfellow Park, offering easy access to local attractions. It has received excellent user ratings, suggesting a comfortable and enjoyable stay.
The property can accommodate up to 12 guests in its 5 bedrooms and 2 bathrooms, making it ideal for families or groups of friends. Amenities include a fully equipped kitchen, a terrace or balcony, a garden, a tennis court, and parking.
Cozy Cottage With Fire Pit, Near Beach, 1 Mile To Nyc Train - Fairfield, CT
10 34 reviews
Fairfield, CT
29/07 – 07/08
656 €/nighttotal: 5904 € (9 )

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

3 2
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.
2-bedroom Modern Apartment For Relaxing Stays - Fairfield, CT
Fairfield, CT
17/08 – 31/08
134 €/nighttotal: 1876 € (14 )

2-bedroom Modern Apartment For Relaxing Stays

2 2
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.

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
Fairfield, CT
01/07 – 08/09
220 €/nighttotal: 15180 € (69 )

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

1 2
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.
Luxurious & Peaceful Home, Perfect Location! 5 Min From Everything. - Fairfield, CT
Fairfield, CT
01/10 – 31/01
107 €/nighttotal: 13054 € (122 )

Luxurious & Peaceful Home, Perfect Location! 5 Min From Everything.

2 4
apartment , Bridgeport
This Bridgeport flat offers a central city location, providing easy access to attractions such as the Beardsley Zoo and the Discovery Museum, with nearby shopping centres and proximity to outdoor pursuits like motor boating and fishing.
Accommodating up to six guests, this two-bedroom, two-bathroom residence features a fully equipped kitchen with a coffee/espresso and smoothie machine, a dedicated office space with high-speed internet, and a private stone side yard for relaxation.
Captain House In Black Rock-academic Rental - Fairfield, CT
Fairfield, CT
19/12 – 02/01
401 €/nighttotal: 5614 € (14 )

Captain House In Black Rock-academic Rental

3 4
apartment , Bridgeport
This three-bedroom flat is located in Bridgeport's historic Black Rock district, offering waterfront views of Burr Creek and situated 6 kilometres from Silver Sands State Park.
This property, spanning 33 square metres and accommodating up to seven guests, features a kitchen with a fridge, microwave, and dishwasher, air conditioning, a garden, parking, and a laundry room, with a check-out time of 10:00 AM.
Modern + Spacious 5br/2ba Home, Renovated Backyard - Fairfield, CT
8.4 6 reviews
Fairfield, CT
17/08 – 31/08
477 €/nighttotal: 6678 € (14 )

Modern + Spacious 5br/2ba Home, Renovated Backyard

5 2
apartment , Bridgeport
This West End, West Side property is less than 2km from Bridgeport's Downtown South Historic District and Lafayette Park, and within 3km of the Housatonic Museum of Art and Downtown Cabaret Theatre.
This five-bedroom house, boasting 232 square metres of floor space, comfortably sleeps 12 guests and includes a fully equipped kitchen, terrace, garden, parking, and free Wi-Fi.
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