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.
2br Flat Above Historic Cider Mill - Fairfield, CT
9.9 351 reviews

2br Flat Above Historic Cider Mill

apartment, Westport
This charming apartment is situated on top of a renovated historic mill in Westport, just a short distance from several beaches. It has consistently received excellent ratings for location, cleanliness, and overall user experience.
The property offers two bedrooms and one bathroom, comfortably accommodating up to five guests. Enjoy modern amenities like smart TVs, a fully equipped kitchen with a dishwasher, and a washer and dryer, along with unique features like a co-working space and a garden.
Sunny Fairfield Studio Apartment - Fairfield, CT
10 191 reviews

Sunny Fairfield Studio Apartment

apartment, Fairfield
This charming studio apartment is located in a historic carriage house in Fairfield, just a short drive from the town centre, the beach and Fairfield University. The studio has received excellent ratings for its location, cleanliness and overall experience, making it a great choice for travellers looking for a comfortable and convenient stay.
The studio is ideal for a couple or a small family, with a queen-size bed and a twin daybed with a pull-out trundle. It features a well-equipped kitchenette, a comfortable living space, a 55-inch Smart LED TV, a private entrance and a dedicated parking space.
Southport Shoreline Charm: Elegant Coastal Escape - Fairfield, CT
9.6 146 reviews

Southport Shoreline Charm: Elegant Coastal Escape

apartment, Fairfield
This 3-bedroom house in Fairfield is located just a short distance from the town centre and a 5-minute drive from the beach. It has received excellent ratings for cleanliness, location, and overall experience.
The house spans 9 square metres and comfortably accommodates up to 7 guests. It includes a fully equipped kitchen, a spacious living area, a private garden, and a range of amenities for a comfortable and enjoyable stay, including a ping pong table, sound machines in each bedroom, and a work-from-home friendly setup.

Best Fairfield, CT holiday rentals with a pool

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

Modern Beach Area Vacation Home With Pool - Fairfield, CT
9.2 30 reviews

Modern Beach Area Vacation Home With Pool

apartment, Fairfield
This Fairfield apartment is located on a quiet historic street, just a block away from the lively Post Road, offering easy access to shops, restaurants and the town centre. The property has received excellent ratings for its cleanliness, location and overall experience.
The home is spacious and designed to evoke a relaxed beach atmosphere. Guests can enjoy outdoor dining by the pool, relax in the garden, and make use of the fully equipped kitchen, which includes a dishwasher, fridge, freezer and microwave.
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.
Newly Renovated Home In Westport Ct, Private Pool, Walk To Town, Close To Beach - Fairfield, CT
No reviews

Newly Renovated Home In Westport Ct, Private Pool, Walk To Town, Close To Beach

apartment, Westport
This three-bedroom house is located in central Westport, just under 2 kilometres from the Westport Historical Society, Levitt Pavilion, and Westport Country Playhouse. The property boasts a private swimming pool, a fully equipped kitchen with a dishwasher, and a barbecue grill for outdoor dining, making it ideal for families or groups of up to 10 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.

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 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.
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.
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.

Best Fairfield, CT holiday rentals with parking

Spacious Westport Apt Surrounded By Nature! - Fairfield, CT
9.8 328 reviews

Spacious Westport Apt Surrounded By Nature!

apartment, Westport
This apartment is located in a quiet residential area, just 8-10 kilometres from the centres of Westport, Fairfield, and Southport. It has received excellent ratings for location, cleanliness and user experience.
The property offers a spacious layout with two bedrooms and a bathroom, suitable for up to four guests. Amenities include a fully equipped kitchen, a private garden, parking, and a walk-in shower, as well as easy access to nearby beaches, golf courses, and nature reserves.
Beach Area 2 Bedroom 
3rd Br / Office On Request - Fairfield, CT
10 13 reviews

Beach Area 2 Bedroom 3rd Br / Office On Request

apartment, Fairfield
This renovated bungalow is located in Fairfield's beach area, just a 1 kilometre walk from the town centre, train station, theatres, restaurants, shops, and beaches. The property is a short distance from the vibrant heart of Fairfield, offering a peaceful retreat while still being within easy reach of all the action.
This two-bedroom flat can comfortably accommodate up to three guests. It features a modern kitchen and bathroom, a fireplace, a cosy patio with a grill, a side yard, a fire pit, parking, 5G WiFi, cable TV with 130 channels, a washer/dryer, and access to bikes, scooters, a kayak, or a stand-up paddleboard with the host's approval.
One Of A Kind Executive Stay In Easton, Ct. - Fairfield, CT
9.4 22 reviews

One Of A Kind Executive Stay In Easton, Ct.

apartment, Easton
This Lower Easton Colonial/Contemporary home is situated in a peaceful, secluded area on 3 acres, just a short drive (around 3 km) from the bustling centre of Easton. The property has excellent user, location and cleanliness ratings.
This spacious residence offers five bedrooms and four bathrooms, comfortably accommodating up to 10 guests. Enjoy a range of amenities including a swimming pool, garden, parking, a fully equipped kitchen, air conditioning and a basement entertainment area with a theatre room, game room and bar.
Peaceful Suburban Colonial W/new Kitchen. - Fairfield, CT
10 135 reviews

Peaceful Suburban Colonial W/new Kitchen.

apartment, Fairfield
This newly renovated three-bedroom house is situated in a quiet, tree-lined suburban neighbourhood in Fairfield, just a short drive from both Fairfield University and Sacred Heart University, as well as shopping and Long Island Sound. The property has received excellent ratings for user experience, location, and cleanliness.
The spacious home can accommodate up to seven guests and is fully equipped with a kitchen, including a fridge, microwave oven, and dishwasher. Amenities include air conditioning, parking, internet access, and a dedicated workspace in the largest bedroom, making it ideal for work-from-home travellers.
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