Holiday Rentals in Fairfield, CT

245 available vacation rental offers

7 nights
2
1
  • airbnb
  • booking
  • vrbo
  • expedia
  • premierinn
  • sykescottages
  • plumguide
  • hotelscom
  • tripadvisor
  • homestay
  • tuivillas
  • hostelworld
Fairfield, CT holiday rentals
Choose the perfect holiday accommodation
Price per night
Accommodation type
Rating

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

Stay At Black Rock Harbor - Fairfield, CT
10 26 reviews
Fairfield, CT
06/08 – 09/08
1064 €/nighttotal: 3192 € (3 )

Stay At Black Rock Harbor

3 5
apartment , Bridgeport
This apartment is located in the Black Rock district of Bridgeport, a short stroll from the beach and a 10-minute drive from Fairfield University, offering a peaceful escape in a quiet neighbourhood. The apartment has excellent user ratings and is a great choice for families or groups of friends. This three-bedroom property can accommodate up to six guests, providing ample space for everyone. The apartment comes equipped with a range of amenities including a fully equipped kitchen, a sunroom, a tranquil backyard, and parking for two vehicles, including an EV charger.
Studio Flat Above Historic Cider Mill - Fairfield, CT
9.9 364 reviews
Fairfield, CT
16/08 – 28/08
161 €/nighttotal: 1932 € (12 )

Studio Flat Above Historic Cider Mill

1 2
studio , Westport
This Westport apartment is conveniently located within a 3-mile radius of Southport Beach, Burying Hill Beach, and the Country Club of Fairfield, making it ideal for exploring the area. It has received excellent ratings for location, cleanliness, and user experience, ensuring a comfortable and enjoyable stay.
The apartment offers a spacious 79 square metre layout with one bedroom and one bathroom, comfortably accommodating up to four guests. It is fully equipped with a kitchen, laundry facilities, air conditioning, a jacuzzi, and parking, as well as free Wi-Fi, a Smart TV, and a coffee/tea maker for a relaxing and convenient stay.
Remodeled Cozy Country Cape - Fairfield, CT
9.9 34 reviews
Fairfield, CT
16/08 – 28/08
370 €/nighttotal: 4440 € (12 )

Remodeled Cozy Country Cape

1 2
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.
1 Bedroom - Bridgeport Apartment - Fairfield, CT
9.6 19 reviews
Fairfield, CT
22/10 – 26/10
170 €/nighttotal: 680 € (4 )

1 Bedroom - Bridgeport Apartment

1 2
apartment , Bridgeport
This apartment is situated above a Tabernacle Church in Bridgeport, offering a unique cultural experience, especially on Sundays at 11 am and Wednesdays at 5 pm. The church's location is likely central, making it easy to explore the city.
The apartment offers a queen-size bed and a pull-out couch, comfortably sleeping up to three guests. It includes a kitchen with a fridge, freezer, and microwave oven, plus parking and internet access.

Best Fairfield, CT holiday rentals with a pool

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

Designer Villa Bordering  Westport - Fairfield, CT
9.9 18 reviews
Fairfield, CT
25/09 – 28/09
1250 €/nighttotal: 3750 € (3 )

Designer Villa Bordering Westport

1 3
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.
Summer Estate Close To Ny, Nj, Ma W Heated Pool Sleeps 16+ - Fairfield, CT
10 73 reviews
Fairfield, CT
27/08 – 30/08
3479 €/nighttotal: 10437 € (3 )

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

1 11
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
22/10 – 26/10
166 €/nighttotal: 664 € (4 )

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.
The "Grant" Estate - Fairfield, CT
10 1 review
Fairfield, CT
27/06 – 04/07
1107 €/nighttotal: 7749 € (7 )

The "Grant" Estate

1 2
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.

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

The B&w Haven 5br Home With Yard Theater + Office - Fairfield, CT
8.8 9 reviews
Fairfield, CT
01/10 – 31/01
376 €/nighttotal: 45872 € (122 )

The B&w Haven 5br Home With Yard Theater + Office

5 4
apartment , Bridgeport
This five-bedroom house in Bridgeport's Brooklawn-St. Vincent neighbourhood is a short walk from the Bridgeport Downtown South Historic District and St Vincent's Medical Center, with Svihra and Lafayette Parks less than 1.6km away.
This 186 square metre family home, sleeping up to 11 guests, boasts a fully equipped kitchen, free WiFi, a balcony, and parking, plus housekeeping is available on request; Bridgeport Station is approximately 2.4km away.
Renovated Cape Near Beach With Fire Pit - Fairfield, CT
Fairfield, CT
06/08 – 09/08
591 €/nighttotal: 1773 € (3 )

Renovated Cape Near Beach With Fire Pit

3 5
house , Fairfield
Fairfield Retreat, a one-bedroom house in Fairfield, Connecticut, is conveniently located 18km from the Connecticut Post Mall, 18km from Silver Sands State Park, and 35km from Yale University.
This self-catering property sleeps up to 17 guests and boasts two bathrooms, free Wi-Fi, private parking, a garden, and air conditioning.
2-bedroom Modern Apartment For Relaxing Stays - Fairfield, CT
Fairfield, CT
25/09 – 28/09
197 €/nighttotal: 591 € (3 )

2-bedroom Modern Apartment For Relaxing Stays

2 3
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.
Charming Colonial For Events!  Perfect For Family Reunions And Group Getaways! - Fairfield, CT
8.8 10 reviews
Fairfield, CT
01/07 – 08/09
787 €/nighttotal: 54303 € (69 )

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.

Best Fairfield, CT holiday rentals with parking

Charming 3-bedroom Beach Cottage In Beautiful Fairfield With Ac - Fairfield, CT
Fairfield, CT
06/08 – 09/08
495 €/nighttotal: 1485 € (3 )

Charming 3-bedroom Beach Cottage In Beautiful Fairfield With Ac

3 5
cottage , Fairfield
This cottage is located in the exclusive Fairfield Beach community, approximately 60 metres from Long Island Sound, a short drive from downtown Fairfield and Southport, and within walking distance of a Par 3 golf course.
This 93 square metre holiday home offers accommodation for up to five guests, featuring three bedrooms, one bathroom, air conditioning, internet, and a kitchen equipped with a fridge, microwave oven, and dishwasher, with direct access to a private beach, playground, and nature trails.
Modern 3-bdrm Apt In Black Rock - Fairfield, CT
9.4 3 reviews
Fairfield, CT
25/09 – 28/09
474 €/nighttotal: 1422 € (3 )

Modern 3-bdrm Apt In Black Rock

3 3
apartment , Bridgeport
This Bridgeport beachfront apartment, near Fairfield, is less than 2km from Longfellow and Seaside Parks and within 5km of Fairfield Museum and History Centre and Fairfield University.
The 111 square metre property boasts four bedrooms, one bathroom, sleeps ten guests, and includes a fully equipped kitchen, in-unit laundry, and on-site parking.
Indulge In Prime Luxury 3br 3-7 Guest - Fairfield, CT
9.6 17 reviews
Fairfield, CT
22/10 – 26/10
687 €/nighttotal: 2748 € (4 )

Indulge In Prime Luxury 3br 3-7 Guest

3 2
house , Bridgeport
This house is conveniently located in Bridgeport, just a short distance from major hospitals, universities, and transport hubs. It has excellent user, location, and cleanliness ratings, making it a great choice for travellers.
The house is spacious and can comfortably accommodate up to 7 guests. It offers a range of modern amenities, including a fully equipped kitchen, a Samsung 85” TV, and a smart night table with a built-in refrigerator drawer, Bluetooth speakers, LED lighting, and charging ports.
3-bedroom 2-bath House In Norwalk With In-law Suite, Pool, Bbq - Fairfield, CT
8.8 8 reviews
Fairfield, CT
23/10 – 25/10
532 €/nighttotal: 1064 € (2 )

3-bedroom 2-bath House In Norwalk With In-law Suite, Pool, Bbq

3 7
apartment , Norwalk
This apartment in Norwalk is located a mere 400 metres from Earthplace Museum and Lockwood Mathews Mansion Museum, with The SoNo Collection and Center Seven Shopping Centre also within easy reach.
This 3-bedroom, 2-bathroom flat accommodates up to 8 guests and includes a microwave oven, dishwasher, air conditioning, and parking, with a swimming pool available on site.
©2026 cozycozy.com