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

Fairfield Favorite - Fairfield, CT
10 23 reviews

Fairfield Favorite

apartment, Fairfield
This Fairfield property is situated on a hill overlooking Brooklawn Country Club, offering a peaceful escape from the city bustle just 1.5 km from the centre of Fairfield. The accommodation is set in a quiet and tranquil setting, ideal for a relaxing getaway.
The house is a spacious four-bedroom property, comfortably accommodating up to eight guests. It boasts a modern kitchen, a swimming pool, a sauna, and a fitness centre, ensuring a comfortable and enjoyable stay.
3br Family Apt, Renovated With Easy Check-in - Fairfield, CT
9.4 54 reviews

3br Family Apt, Renovated With Easy Check-in

apartment, Bridgeport
This apartment is conveniently located just a short distance from Seaside Park and Captain's Cove Seaport, offering easy access to the beach and Bridgeport's waterfront attractions. It has consistently received excellent ratings for cleanliness, location, and overall user experience.
The apartment has three bedrooms, accommodating up to eight guests, perfect for families or groups of friends. The fully equipped kitchen, comfortable living area, and smart TVs provide everything you need for a relaxing and enjoyable stay, while the dedicated workspace with Wi-Fi is ideal for those who need to work remotely.
Fairfield Horse Country Serene Getaway - Fairfield, CT
9.4 7 reviews

Fairfield Horse Country Serene Getaway

apartment, Fairfield
This apartment is located in a tranquil countryside setting in Fairfield, offering a peaceful retreat from the hustle and bustle of city life. It is highly rated by previous guests, receiving excellent scores for location, cleanliness, and overall experience.
The apartment has three bedrooms and three bathrooms, comfortably accommodating up to seven guests. It comes equipped with modern amenities such as a fully fitted kitchen, air conditioning, a garden, a fitness centre, and parking, ensuring a comfortable and enjoyable stay.
Villa Après Sea - Fairfield, CT
9.0 8 reviews

Villa Après Sea

house, Westport
This stylish apartment is located on a private 1-acre gated estate, offering seclusion while remaining a short distance from Westport's amenities.
This 4-bedroom, 3-bathroom property sleeps six guests and features a dedicated playroom, ping-pong table, fire pit, outdoor furniture, and an 85-inch television, making it ideal for family stays.

Best Fairfield, CT holiday rentals with a pool

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

Spacious Easton 2br Townhouse With Big Yard - Fairfield, CT
No reviews

Spacious Easton 2br Townhouse With Big Yard

apartment, Easton
This secluded 2-bedroom cottage on a 2-hectare estate offers a tranquil natural setting in Easton, bordering a nature preserve and located 8-22 kilometres from attractions including Trout Brook Valley Conservation Area, Silverman's Farm and Compo Beach.
This well-equipped townhouse provides accommodation for up to 5 guests with its 177 square metre floor area, featuring a king-size bed, queen-size bed, sofa bed, a fully equipped kitchen, high-speed WiFi, a shared seasonal swimming pool, hot tub, and private garden with hammock and views.
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.
Last Minute Availability - 5-bed W Heated Pool - Fairfield, CT
10 1 review

Last Minute Availability - 5-bed W Heated Pool

apartment, Westport
This expansive Westport house, near the town centre and beaches, offers easy access to New York City, approximately 60 kilometres away.
The 9,600 sq ft property sleeps twelve guests in five en-suite bedrooms, boasting a gourmet kitchen with Sub-Zero appliances, a saltwater pool, spa, extensive outdoor entertaining area, a 2,500 sq ft finished basement with a wine room, and a fitness centre.
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.

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

Luxury Cabin For 6 - Stream - Pond - Custom Kitchen - Fairfield, CT
10 1 review

Luxury Cabin For 6 - Stream - Pond - Custom Kitchen

cabin, Redding
This luxury A-frame lodge is located in the wooded outskirts of Redding, Connecticut, offering a secluded natural setting just a short drive from New York City.
This renovated two-bedroom, two-bathroom accommodation boasts a custom chef's kitchen with Miele appliances, a king suite with a wet bar, an upstairs bedroom with two queen beds and a private balcony, and exclusive access to the entire property, including a private pond and stream, and is conveniently located within 5 kilometres of the Discovery Museum, The Cave, Monroe Plaza Shopping Centre and Bethel Plaza Shopping Centre.
Zen, Spacious & Comfy 2 Bed, Lux Beds - Fairfield, CT
10 2 reviews

Zen, Spacious & Comfy 2 Bed, Lux Beds

apartment, Bridgeport
This two-bedroom basement flat is situated in Bridgeport's Brooklawn-St. Vincent neighbourhood, conveniently close to Sacred Heart University and Bridgeport Hospital.
The 2-bedroom property sleeps 5, boasts high-speed internet, a washer/dryer, and a fully equipped kitchen, plus access to a large yard with a swing; nearby attractions include the Bridgeport Downtown South Historic District and Fairchild Wheeler Golf Course.
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.
The Blue Sapphire: Modern & Stylish 2br W/ 2 King Beds & Full Kitchen - Fairfield, CT
9.0 2 reviews

The Blue Sapphire: Modern & Stylish 2br W/ 2 King Beds & Full Kitchen

apartment, Bridgeport
This Bridgeport apartment, situated in the Brooklawn-St. Vincent neighbourhood, offers convenient proximity to attractions such as Beardsley Zoo, the Discovery Museum, and Fairchild Wheeler Golf Course.
The 186 square metre (1999 square foot) property boasts two bedrooms, one bathroom, and sleeps five, featuring a fully equipped kitchen, smart TVs, a terrace, garden access, and high-speed internet.

Best Fairfield, CT holiday rentals with parking

Charming 2br Getaway With Modern Comforts - Fairfield, CT
8.4 13 reviews

Charming 2br Getaway With Modern Comforts

apartment, Bridgeport
This Bridgeport apartment, situated 15.3 km from Silver Sands State Park and 19.3 km from the Connecticut Post Mall, offers convenient access to both natural beauty and shopping.
This two-bedroom flat boasts 186 square metres of floor space, a fully equipped kitchen with dishwasher and microwave, accommodating up to nine guests and including free Wi-Fi, on-site parking, a garden, and a barbecue.
Pleasant Wellness Home Bridgeport-2 - Fairfield, CT
10 3 reviews

Pleasant Wellness Home Bridgeport-2

apartment, Bridgeport
This three-bedroom flat in Bridgeport is located in a convenient district, offering easy access to the Bridgeport Museum and the historic Barnum Museum, both within 1 kilometre.
This stylish apartment accommodates up to nine guests and features air conditioning, internet, a kitchen, and parking, making it an ideal base for exploring Bridgeport.
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.
Black Rock Suites-86-1 - Fairfield, CT
9.0 3 reviews

Black Rock Suites-86-1

apartment, Bridgeport
Black Rock Suites offers a one-bedroom apartment in Bridgeport's Black Rock neighbourhood, conveniently located 2.7 kilometres from Jennings Beach.
This self-contained flat provides free Wi-Fi, in-unit laundry, air conditioning, and parking, sleeping one guest and is ideal for exploring Bridgeport and its surroundings.
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