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

Cozy Condo With Yard And Patio. Long-stay Discount Available - Fairfield, CT
9.7 169 reviews

Cozy Condo With Yard And Patio. Long-stay Discount Available

apartment, Fairfield
This Fairfield apartment is conveniently located just 10 miles from Silver Sands State Park and 13 miles from the Connecticut Post Mall Shopping Center, offering a great base for exploring the area. The property has consistently received excellent ratings for location, cleanliness, and overall user experience.
This three-bedroom apartment can comfortably accommodate up to six guests. It features a fully equipped kitchen, a private patio, a garden, and free parking, making it a great choice for families or groups looking for a comfortable and convenient stay.
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.
Stay At Black Rock Harbor - Fairfield, CT
9.9 73 reviews

Stay At Black Rock Harbor

apartment, 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.
*Pool Open* Multi Family Retreat - Nature Spa Fire - Fairfield, CT
9.8 8 reviews

*Pool Open* Multi Family Retreat - Nature Spa Fire

farm, Fairfield
This Fairfield County farmhouse, located within walking distance of Fairfield's beaches, restaurants, and shops, offers convenient access to New York City via a 45-minute train journey from Grand Central Terminal or a 1-hour drive (approx. 64km).
The property comprises two homes with designer interiors, sleeping up to 14 guests across 6 bedrooms and 4 bathrooms, boasting a swimming pool, jacuzzi, large garden, and chef's kitchen; amenities include a dishwasher, microwave, and large TVs.

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.
Quaint Private Two Bdrm With Balcony, Stream View! - Fairfield, CT
9.3 15 reviews

Quaint Private Two Bdrm With Balcony, Stream View!

apartment, Bridgeport
This two-bedroom flat in Bridgeport offers convenient access, being just a 4-minute drive from Sacred Heart University.
This Airbnb provides high-speed WiFi, a fully equipped kitchen, and a private balcony, comfortably accommodating up to five guests with new Serta Sleeper mattresses.
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.
Fairfield! 5 Bedroom, 3.5 Bath On Cul-de-sac - Fairfield, CT
10 52 reviews

Fairfield! 5 Bedroom, 3.5 Bath On Cul-de-sac

apartment, Fairfield
This spacious, renovated apartment in Fairfield is conveniently located just a short distance from the town centre, universities, and transportation to NYC Grand Central. The apartment boasts excellent user, location and cleanliness ratings, making it a popular choice for travellers.
The apartment has 5 bedrooms and 3 bathrooms, comfortably accommodating up to 12 guests. Amenities include a private heated pool, a well-equipped kitchen, a spacious living area, a family room with a large TV, and a fully furnished garden with outdoor furniture.

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

The B&w Haven: Stylish 3br Escape With Private Office By Li Ferry - Fairfield, CT
No reviews

The B&w Haven: Stylish 3br Escape With Private Office By Li Ferry

apartment, Bridgeport
This Bridgeport apartment, situated in the Brooklawn-St. Vincent neighbourhood, offers convenient proximity to Beardsley Zoo, the Discovery Museum, and Fairchild Wheeler Golf Course.
The 186 square metre (1991 square feet) property comprises four bedrooms, one bathroom, and accommodates six guests, boasting a stylish black and white interior, a fully equipped kitchen, high-speed internet, smart TVs, and a private balcony with access to a shared garden and 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.
The B&w Haven 5br Home With Yard Theater + Office - Fairfield, CT
8.8 10 reviews

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

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.
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.

Best Fairfield, CT holiday rentals with parking

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.
Blackrock One Bedroom Apt. By The Park & St.marys - Fairfield, CT
10 18 reviews

Blackrock One Bedroom Apt. By The Park & St.marys

apartment, Bridgeport
This Bridgeport apartment, ideally located near Saint Mary's by the Sea boardwalk, offers easy access to coastal walks.
The first-floor flat features a spacious layout including a living room, dining room, breakfast nook, and sun porch, sleeping two guests and boasting a fully equipped kitchen, private garden and parking.
Brooklawn House Classic Victorian - Fairfield, CT
8.9 86 reviews

Brooklawn House Classic Victorian

apartment, Bridgeport
This Bridgeport apartment, near Seaside Park Beach and Bridgeport's Metro-North station, is a historically restored property designed by James Northrup and featured in the film "Away We Go".
The one-bedroom, one-bathroom flat sleeps four guests and offers a full kitchen, washer/dryer, complimentary bicycles, and access to a yard and veranda; nearby attractions include parks, restaurants, and shops.
Modern Westport Studio With Pool Table & Lounge - Fairfield, CT
8.7 14 reviews

Modern Westport Studio With Pool Table & Lounge

studio, Westport
This Westport studio apartment is conveniently located approximately 32 to 43 kilometres from the Connecticut Post Mall and the Russian Railway Museum.
The 107-square-metre self-contained unit sleeps seven guests and features a fully equipped kitchen, air conditioning, free Wi-Fi, a private entrance, and a pool table.
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