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Fairfield, CT vacation rentals
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Best Vacation rentals and Airbnb offers in Fairfield, CT

Best family friendly Fairfield, CT vacation rentals

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

Beach And Pool Escape In Luxury Westport Home - Fairfield, CT
Fairfield, CT
08/27 – 08/30
$2129/nighttotal: $6387 (3 )

Beach And Pool Escape In Luxury Westport Home

1 11
apartment , Westport
This Westport, Connecticut home is located less than a mile from downtown Westport's shops and restaurants and within 3 miles of two beaches, one public and one private.
This luxurious 4-bedroom, 3-bathroom house sleeps 8, boasting a saltwater pool, 60-jet spa hot tub, outdoor movie setup, fully fenced backyard with fire pit, and a finished basement with playroom and 60" TV.
Beautiful Brand New Inviting Farmhouse - Fairfield, CT
9.8 31 reviews
Fairfield, CT
08/06 – 08/09
$1347/nighttotal: $4041 (3 )

Beautiful Brand New Inviting Farmhouse

1 5
apartment , Westport
This family-friendly apartment in Westport, nestled in a serene neighborhood on a private 1-acre lot, offers a peaceful retreat with ample outdoor space. With excellent user, location, and cleanliness ratings, this 5-bedroom, 3-bathroom apartment comfortably accommodates 10 guests.
The open and bright first floor features a gourmet kitchen, dining room, family room with fireplace, and gaming room. The basement entertainment area offers games, trampoline mats, and aerial silks. Outdoor amenities include a deck with furniture, grill, bonfire pit, zipline, and ropes course. Winter and summer gear is also provided, making this apartment perfect for any season.
Fairfield Beach â›±Renovated Cape - 3 Bed 2 Bath - Fairfield, CT
9.9 24 reviews
Fairfield, CT
09/06 – 09/20
$608/nighttotal: $8512 (14 )

Fairfield Beach â›±Renovated Cape - 3 Bed 2 Bath

1 2
apartment , Fairfield
This Fairfield house is conveniently located less than a mile from the beach, downtown, and the Metro North train station, making it easy to explore all that the town has to offer. The accommodation has received excellent ratings for its location, cleanliness, and overall experience.
The house has three bedrooms and two bathrooms, comfortably accommodating up to four guests. Enjoy modern comforts, including a full kitchen, central AC, high-speed Wi-Fi, a smart TV, an office area, a private garden with a fire pit, and a new outdoor shower.
Beautiful Home In The Town Of Fairfield. - Fairfield, CT
10 4 reviews
Fairfield, CT
08/06 – 08/09
$595/nighttotal: $1785 (3 )

Beautiful Home In The Town Of Fairfield.

4 5
apartment , Fairfield
This recently renovated 4-bedroom, 2-bathroom house is located in Fairfield, just minutes from Sacred Heart University and central to local amenities.
This pet-friendly rental accommodates up to 9 guests and features hardwood floors, a full kitchen with a microwave and dishwasher, air conditioning, parking, and a backyard with a fire pit.

Best Fairfield, CT vacation rentals with a pool

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

Home In Fairfield - Fairfield, CT
10 5 reviews
Fairfield, CT
09/25 – 09/28
$1103/nighttotal: $3309 (3 )

Home In Fairfield

1 3
apartment , Fairfield
This modern home in Fairfield is conveniently located less than a mile from the freeway exit and Metro North station, placing you within easy reach of both New York City and local attractions. The town center, shopping, and restaurants are just a 10-minute walk away.
This 5-bedroom, 3-bathroom house comfortably accommodates up to 10 guests. The home offers a range of amenities, including a fully equipped kitchen, a private pool, a fenced-in backyard, and a fitness center, ensuring a comfortable and enjoyable stay for families and groups.
Paradise Awaits
5 Acre Estate - Sasco Hill - Fairfield, CT
10 5 reviews
Fairfield, CT
10/22 – 10/26
$5791/nighttotal: $23164 (4 )

Paradise Awaits 5 Acre Estate - Sasco Hill

1 2
apartment , Fairfield
This luxury estate sits on Sasco Hill in Fairfield, just steps from Sasco Beach and a short distance from the charming town center. The property boasts excellent user, location, and cleanliness ratings, making it a top choice for travelers seeking a comfortable and enjoyable stay. This spacious home features 5 bedrooms and 5 bathrooms, comfortably accommodating up to 10 guests. The property offers a range of amenities, including a private pool, gardens, a martini lounge, and a dedicated children's suite, ensuring a memorable and relaxing vacation for all.
Access To Relax! - Fairfield, CT
10 4 reviews
Fairfield, CT
10/22 – 10/26
$1331/nighttotal: $5324 (4 )

Access To Relax!

1 2
apartment , Fairfield
This Fairfield home is located a short walk from the beach, downtown, and the train station, offering easy access to restaurants, shops, and the Fairfield Theater Company. The train station provides a quick commute to Grand Central Terminal in New York City.
The three-bedroom home comfortably sleeps five guests and features a kitchen, a fireplace, and a heated pool. You can enjoy a relaxing atmosphere, swimming, sunbathing, and exploring the beautiful Fairfield coastline.
Fairfield Beach Modern Colonial - Fairfield, CT
10 7 reviews
Fairfield, CT
10/01 – 01/31
$621/nighttotal: $75762 (122 )

Fairfield Beach Modern Colonial

1 4
apartment , Fairfield
This 4-bedroom colonial apartment is located in the heart of Fairfield's beach neighborhood, just steps from Penfield Beach and a short stroll to the vibrant town center. It has an excellent user rating and offers 3500 square feet of living space.
The apartment features a chef's kitchen with a large island, a private backyard with a pool house doubling as a gym, a dining room with seating for 8, and a 3rd-floor bonus space. It also includes amenities such as air conditioning, a swimming pool, a garden, a fitness center, and parking.

Frequently Asked Questions about vacation rentals in Fairfield, CT

  • What are the must-see sights in Fairfield, Connecticut?

    Fairfield Beach is a must, especially during summer. The historic Fairfield Museum and History Center offers a glimpse into the town's past. Lake Mohegan offers beautiful scenery and recreational opportunities. The Sherman Green is a lovely park in the center of town, perfect for a stroll.
  • What are the best Airbnb and vacation 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 vacation rentals in Fairfield, CT among travelers.

  • Are there unique natural phenomena in Fairfield, Connecticut?

    While Fairfield doesn't have dramatic geological features, its location on Long Island Sound provides beautiful coastal scenery and diverse wildlife. The tidal marshes are important ecosystems, and you'll find a variety of bird species. The beaches themselves are a significant natural feature.
  • What are the most popular Airbnbs in Fairfield, CT?

  • What essentials should you bring along for a trip to Fairfield, Connecticut?

    Comfortable walking shoes are a must, as is sunscreen and a hat, especially during the summer months. Depending on the time of year, you might also want a light jacket or sweater. Don't forget swimwear if you plan on visiting the beach.
  • What are the best vacation rentals with a pool in Fairfield, CT?

  • What is the average daily budget you should plan for (accommodation, food, transportation, activities) in Fairfield, Connecticut?

    A daily budget will vary greatly depending on your choices. Accommodation can range from budget-friendly motels to upscale hotels. Food costs can vary from inexpensive takeout to fine dining. Transportation costs depend on whether you rent a car or use public transportation (which is limited). A reasonable estimate for a mid-range daily budget might be between $150-$300 per person, but it could easily be higher or lower.
  • 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. For seafood, try the Black Bear Saloon or another restaurant along the coast. There are also many Italian restaurants reflecting the area's heritage. There isn't one specific 'must-try' Fairfield specialty, but the focus is on fresh, seasonal ingredients.
  • 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 the visit?

    The Pequotsepos Nature Center offers nature trails and educational programs. The various smaller parks scattered throughout town provide peaceful escapes. Exploring the residential streets can reveal charming architecture and historical homes.
  • What are the best activities for engaging with locals and understanding their culture in Fairfield, Connecticut?

    Visiting local businesses, like independent shops and restaurants, is a great way to interact with residents. Attending community events, if any are scheduled during your visit, can also provide opportunities to meet locals. Simply striking up conversations with people you encounter is another way to experience the local culture.
  • What unique natural landscapes and terrain features can travelers explore in Fairfield, Connecticut?

    Fairfield's main natural features are its coastline, including the beaches and tidal marshes, and Lake Mohegan. The terrain is relatively flat, with rolling hills in some areas, but nothing dramatically mountainous.
  • How many days are ideal for visiting Fairfield, Connecticut, and what are some itinerary suggestions?

    A long weekend (3 days/2 nights) is sufficient to see the main attractions. A possible itinerary could include: Day 1 - Fairfield Beach and the Fairfield Museum; Day 2 - Lake Mohegan and exploring the downtown area; Day 3 - Pequotsepos Nature Center and a relaxing walk through Sherman Green. Longer stays allow for more exploration of the surrounding areas.
  • How is the weather in Fairfield, Connecticut in high season?

    Fairfield's high season is summer (June-August). Expect warm temperatures, often in the 70s and 80s Fahrenheit (20s and 30s Celsius), with humidity. There's always a chance of rain showers, so packing layers and rain gear is advisable.

Nearby regions

Best Fairfield, CT vacation rentals with a balcony

Cozy Condo With Yard And Patio. Long-stay Discount Available - Fairfield, CT
9.7 159 reviews
Fairfield, CT
08/16 – 08/28
$328/nighttotal: $3936 (12 )

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

3 2
apartment , Fairfield
This Fairfield apartment is conveniently located about 10 miles from Silver Sands State Park and 13 miles from Connecticut Post Mall Shopping Center, making it a great base for exploring the area. The apartment has received excellent ratings for location, cleanliness, and overall user experience, ensuring a comfortable and enjoyable stay.
The spacious apartment can comfortably accommodate up to 6 guests in its 3 bedrooms and 2 bathrooms. Guests can enjoy a private patio and yard, a fully equipped kitchen with a dishwasher, and access to free parking and Wi-Fi.
Renovated Cape Near Beach With Fire Pit - Fairfield, CT
Fairfield, CT
08/06 – 08/09
$683/nighttotal: $2049 (3 )

Renovated Cape Near Beach With Fire Pit

3 5
house , Fairfield
Fairfield Retreat, a one-bedroom house in Fairfield, Connecticut, is conveniently located 11 miles from Silver Sands State Park and 14 miles from the Connecticut Post Mall.
This two-bathroom home sleeps up to 17 guests and offers free Wi-Fi, private parking, a fully equipped kitchen, and a relaxing garden; enjoy easy access to shopping, beaches, and Yale University (22 miles away).
4 Mi To Beach & Dtwn! Charming Fairfield Home - Fairfield, CT
Fairfield, CT
08/06 – 08/09
$729/nighttotal: $2187 (3 )

4 Mi To Beach & Dtwn! Charming Fairfield Home

4 5
house , Fairfield
This Fairfield house is located 4 miles from the beach and downtown Fairfield, 10 miles from Silver Sands State Park, and 20 miles from Yale University.
This 1500 square foot home offers 4 bedrooms, 2 bathrooms, a full kitchen with a dishwasher and microwave, air conditioning, and free private parking, accommodating up to 17 guests.
2-bedroom Modern Apartment For Relaxing Stays - Fairfield, CT
Fairfield, CT
09/06 – 09/20
$154/nighttotal: $2156 (14 )

2-bedroom Modern Apartment For Relaxing Stays

2 2
apartment , Bridgeport
This 2-bedroom, 1-bathroom apartment is located in Bridgeport's West End, offering easy access to Silver Sands State Park (approximately 4 miles away), The Coastal Center at Milford Point (approximately 4 miles away), Beardsley Zoo (approximately 1 mile away), and the Regina A. Quick Center for the Arts (approximately 1 mile away), as well as being within walking distance to the Hartford HealthCare Amphitheater and Total Mortgage Arena.
This pet-friendly rental accommodates up to 4 guests with a king bed and a queen bed, featuring air conditioning, internet, a terrace/balcony, and on-site parking for your convenience.

Neighborhoods and points of interest in Fairfield, CT

Best Fairfield, CT vacation rentals with parking

Lake Hills Suite - Fairfield, CT
10 26 reviews
Fairfield, CT
09/06 – 09/20
$232/nighttotal: $3248 (14 )

Lake Hills Suite

1 2
apartment , Fairfield
This modern one-bedroom suite is located in Fairfield's upscale Lake Hills neighborhood, offering convenient proximity to local universities, restaurants, and shops.
The 1-bedroom apartment features a queen bed, queen-size pull-out sofa, full kitchenette, in-unit washer/dryer, private balcony overlooking a garden, dedicated parking, and central air conditioning, comfortably accommodating up to four guests.
Family Home Near Roosevelt Forest & Historic Sites - Fairfield, CT
Fairfield, CT
10/01 – 01/31
$273/nighttotal: $33306 (122 )

Family Home Near Roosevelt Forest & Historic Sites

4 4
apartment , Stratford
This Stratford rental is located less than 1 mile from Roosevelt Forest and Boothe Memorial Park & Stratford Veterans Museum, with easy access to the Merritt Parkway and within a short drive of universities like Yale.
This 1580 square foot apartment accommodates up to 8 guests, featuring 4 bedrooms, 2 bathrooms, a full kitchen with a dishwasher, air conditioning, free WiFi, and a step-free entry.
Stay At Black Rock Harbor - Fairfield, CT
8.7 3 reviews
Fairfield, CT
08/16 – 08/28
$950/nighttotal: $11400 (12 )

Stay At Black Rock Harbor

3 2
house , Bridgeport
This Bridgeport beach house is located 11 miles from Silver Sands State Park and 14 miles from the Connecticut Post Mall, offering easy access to both beach activities and shopping.
The 1300-square-foot home features three bedrooms, two bathrooms, sleeps up to 11 guests, and includes amenities such as a fully equipped kitchen, free Wi-Fi, and on-site electric vehicle charging.
Modern 2 Bedroom In Black Rock - Fairfield, CT
9.8 8 reviews
Fairfield, CT
06/27 – 07/04
$342/nighttotal: $2394 (7 )

Modern 2 Bedroom In Black Rock

2 2
apartment , Bridgeport
This Bridgeport apartment rental in Black Rock offers easy access to nearby beaches, the Connecticut Audubon Birdcraft Museum, and the Discovery Museum.
The two-bedroom, one-bathroom unit sleeps four guests and includes in-suite laundry, a fully equipped kitchen with a fridge and microwave, air conditioning, parking, and internet access.
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