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

Renovated Retreat With Heated Pool - Fairfield, CT
9.4 3 reviews

Renovated Retreat With Heated Pool

apartment, Redding
This Redding, Connecticut rental is located in the peaceful Redding Center, five minutes from top-rated restaurants, ten minutes from Ridgefield's shopping and dining, and fifteen minutes from Collis P. Huntington State Park. This five-bedroom, three-bathroom home, boasting a heated saltwater pool, pizza oven, and fire pit, comfortably sleeps nine guests and features a modern gourmet kitchen with Taj Mahal quartzite countertops.
Beautiful Brand New Inviting Farmhouse - Fairfield, CT
9.8 32 reviews

Beautiful Brand New Inviting Farmhouse

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.
Downtown Fairfield 3 Bedroom Colonial - Fairfield, CT
9.9 143 reviews

Downtown Fairfield 3 Bedroom Colonial

apartment, Fairfield
This charming Colonial home is situated in a quiet neighborhood, just a short walk from the bustling Post Road and a mile from Fairfield's beautiful beaches. It has excellent user, location, and cleanliness ratings.
The home has over 1500 square feet with 3 bedrooms, 2 full bathrooms, and a guest capacity of 6. It includes a kitchen with a fridge, freezer, microwave oven, and dishwasher, as well as air conditioning, a garden, parking, and a paved basketball court.
Spacious Family Home, Sleeps 10, Pet Friendly - Fairfield, CT
9.6 49 reviews

Spacious Family Home, Sleeps 10, Pet Friendly

apartment, Bridgeport
This Bridgeport apartment is conveniently located in Brooklawn, close to Fairfield University, Sacred Heart University, and the University of Bridgeport, making it ideal for travelers visiting the area. The apartment has received excellent ratings for its location, cleanliness, and overall experience, ensuring a comfortable and enjoyable stay.
The apartment features four bedrooms and two bathrooms, comfortably accommodating up to ten guests. Guests can enjoy a fully equipped kitchen, a spacious living area, a private garden, and on-site parking, along with other amenities like air conditioning and internet access.

Best Fairfield, CT vacation rentals with a pool

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

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 2-bedroom, 1-bathroom rental unit is located in Bridgeport, just a 4-minute drive from Sacred Heart University.
This Airbnb offers high-speed WiFi, a fully stocked kitchen, and a private balcony, comfortably sleeping up to 5 guests with brand new Serta Sleeper mattresses.
Private Resort Mansion With Pool - Fairfield, CT
10 16 reviews

Private Resort Mansion With Pool

house, Fairfield
This Georgian Colonial estate is a fully gated 2-acre property in Fairfield, offering secluded luxury and proximity to local shops and restaurants.
This spacious residence accommodates up to 16 guests with 7 bathrooms, a chef's kitchen, home theater, game room, heated swimming pool, tennis court, and a separate guest house with a gym and sauna.
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 exceptional accommodation in Weston offers an unparalleled experience for families seeking comfort and luxury. With excellent user, location, and cleanliness ratings, guests can expect an unforgettable stay.
The property features four spacious bedrooms and five bathrooms, accommodating up to four guests. Its fully equipped kitchen, air conditioning, and private garden create a homely ambiance, while the swimming pool, jacuzzi, sauna, and fitness center provide ample opportunities for relaxation and recreation.
The "Grant" Estate - Fairfield, CT
10 1 review

The "Grant" Estate

apartment, Fairfield
This colonial estate is located near the Long Island Sound in Fairfield, offering convenient access to beaches and forest trails within a 10-minute drive, and is adjacent to Westport.
This 5-bedroom, 4-bathroom vacation home accommodates up to 10 guests and features a heated outdoor swimming pool, a Hot Spring Jacuzzi, a chef's kitchen with a 15-foot marble island, a basement with a Peloton and Nintendo, and EV car charging ports.

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

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 Bridgeport colonial home rental, located in the Downtown South Historic District near Perry House, offers easy access to Beardsley Zoo, The Discovery Museum's Adventure Park, and Fairchild Wheeler Golf Course.
This 3,300-square-foot residence boasts six bedrooms, four bathrooms, off-street parking for six cars, and an expansive lawn, comfortably accommodating up to twelve guests with amenities including a microwave, air conditioning, and updated stainless steel appliances.
Charming &Spacious 3bd, 1ba, Fam-friendly-yard&porch - Fairfield, CT
10 3 reviews

Charming &Spacious 3bd, 1ba, Fam-friendly-yard&porch

apartment, Fairfield
This Fairfield, Connecticut apartment rental is located in the West End - West Side neighborhood, near Baldwin Plaza Shopping Center and within easy driving distance of Beardsley Zoo and the Discovery Museum.
This spacious 1,000-square-foot home features four bedrooms, one bathroom, and accommodates up to seven guests, boasting a fully equipped kitchen, a private yard with fire pits, a game room (additional fee applies), and a home theater with massage chairs.
Renovated Cape Near Beach, With Fire Pit And Bbq, 1 Mile To Nyc Train - Fairfield, CT
10 18 reviews

Renovated Cape Near Beach, With Fire Pit And Bbq, 1 Mile To Nyc Train

apartment, Fairfield
This Fairfield vacation home, near Sacred Heart University and minutes from Jennings and Penfield Beaches, offers easy access to the Norwalk Aquarium and Beardsley Zoo.
This five-bedroom, two-bathroom house sleeps ten, features a fully equipped kitchen, outdoor patio with BBQ, Roku smart TVs, fast Wi-Fi, driveway parking for three cars, and pet-friendly accommodations for dogs under 30 pounds.
2-bedroom Modern Apartment For Relaxing Stays - Fairfield, CT
No reviews

2-bedroom Modern Apartment For Relaxing Stays

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

Westport Summer Rental Of Love - Fairfield, CT
No reviews

Westport Summer Rental Of Love

apartment, Westport
This Westport apartment rental is located less than one minute from downtown Westport's shops and restaurants and under five minutes from Compo Beach, including beach passes.
The six-bedroom, six-bathroom home comfortably sleeps twelve guests and boasts a saltwater pool, Jacuzzi, kids' basement with basketball court and soccer goal, outdoor movie theater, and a family SUV for local use.
Remodeled Cozy Country Cape - Fairfield, CT
10 40 reviews

Remodeled Cozy Country Cape

apartment, Fairfield
This Fairfield apartment is conveniently located near the town center, making it easy to explore shops, restaurants, and attractions. The property has received excellent ratings for location, cleanliness, and overall user experience.
This two-bedroom, two-bathroom home comfortably accommodates up to four guests. The apartment features a fully equipped kitchen, a private backyard with a patio, and a finished lower level with a workspace and laundry facilities.
Zen, Spacious & Comfy, Lux Beds - Fairfield, CT
9.8 39 reviews

Zen, Spacious & Comfy, Lux Beds

apartment, Bridgeport
This basement apartment is located in Bridgeport, conveniently close to both Sacred Heart and Bridgeport hospitals. It's a quiet and comfortable retreat offering a peaceful escape from the city. The apartment consistently receives excellent ratings for cleanliness, location, and user experience.
This two-bedroom rental comfortably sleeps four guests and includes a fully equipped kitchen with a fridge, freezer, microwave, and coffee maker. Guests can enjoy high-speed internet, a large yard with a swing, a washer and dryer, and a new TV with a soundbar for streaming.
*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 NYC via a 1-hour drive or a 45-minute train ride from Grand Central Terminal.
This two-home property features six bedrooms, four bathrooms, and accommodates up to 14 guests, boasting a chef's kitchen, a wood-burning fireplace, a swimming pool, a jacuzzi, and a spacious yard perfect for recreation.
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