Compare best Airbnb in Fairfield, CT from 100+ providers!

355 available vacation rental offers

7 nights
2
1
  • airbnb
  • booking
  • vrbo
  • expedia
  • sonder
  • priceline
  • tripadvisor
  • tripcom
  • homestay
  • hotelscom
  • orbitz
  • vacasa
Fairfield, CT vacation rentals
Choose the perfect vacation accommodation
Price per night
Accommodation type
Rating

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

Politas Place # 3 - Fairfield, CT
9.9 84 reviews

Politas Place # 3

apartment, Bridgeport
This Bridgeport apartment is located on the third floor of a building, just a short walk from the waterfront and a quick drive to the city's museums and downtown area. The apartment has received excellent ratings for location, cleanliness, and overall user experience.
The apartment offers a peaceful retreat from the city's hustle and bustle, with a spacious layout that can comfortably accommodate up to six guests. Enjoy a fully equipped kitchen, laundry facilities, a private backyard, and easy access to shared porches and outdoor spaces.
Renovated Cape Near Beach With Fire Pit - Fairfield, CT
No reviews

Renovated Cape Near Beach With Fire Pit

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).
Downtown Fairfield 3 Bedroom Colonial - Fairfield, CT
9.9 140 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.
Retro Bridgeport Apartment - Fairfield, CT
9.6 37 reviews

Retro Bridgeport Apartment

apartment, Bridgeport
This Bridgeport apartment is located in a lively area, just a short walk from Starbucks, a bakery, a supermarket, and a pharmacy. The apartment has excellent user, location, and cleanliness ratings, making it a great choice for travelers. The apartment has two bedrooms with queen-size beds and a living room with a pull-out couch, comfortably accommodating up to four guests. The apartment includes a fully equipped kitchen, air conditioning, parking, and internet access, ensuring a comfortable and convenient stay.

Best Fairfield, CT vacation rentals with a pool

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

1br Guest Apt. Suite /Full Bath, Kitchen -Pool/spa - Fairfield, CT
10 6 reviews

1br Guest Apt. Suite /Full Bath, Kitchen -Pool/spa

apartment, Weston
This Weston, Connecticut guesthouse is located near Westport and a short drive from New York City, offering a secluded retreat on a three-acre estate.
The private suite features a California king bed, a sleeper sofa accommodating up to three guests, a kitchenette with a refrigerator and microwave, and access to a heated 50-foot gunite pool, spa, and furnished private terrace; a washer and dryer are available in the pool house.
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.
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 Fairfield apartment is conveniently located near town, universities, and transportation to NYC Grand Central, making it easy to explore both the city and the surrounding area. The apartment consistently receives excellent ratings for location, cleanliness, and user experience.
The spacious dwelling features five bedrooms and three bathrooms, comfortably accommodating up to twelve guests. This family-friendly rental offers a private pool, a fenced-in yard, a modern kitchen, a spacious garage, and a driveway, providing everything needed for a relaxing and enjoyable stay.
Westport Dream Home- Perfect Winter Escape - Fairfield, CT
No reviews

Westport Dream Home- Perfect Winter Escape

apartment, Westport
This Westport villa is located one minute from downtown Westport and under five minutes from Compo Beach, offering easy access to local attractions.
This six-bedroom, five-bathroom house sleeps nine guests and boasts a private pool, hot tub, indoor movie theater, fully finished basement with games, outdoor basketball court, and even ski equipment for winter fun.

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.
Luxury Designer 2 Bedroom+office/3bed Vacation Home. - Fairfield, CT
9.6 26 reviews

Luxury Designer 2 Bedroom+office/3bed Vacation Home.

apartment, Bridgeport
This fully furnished apartment is located in the Brooklawn - St. Vincent neighborhood of Bridgeport, just a short distance from downtown Bridgeport, Bridgeport Hospital, and major highways for easy access to other Connecticut destinations. The property has received excellent user ratings, making it a popular choice for travelers.
The 1,500 square foot apartment can comfortably accommodate up to 5 guests with its 3 bedrooms and 1 bathroom. It offers a range of amenities including a fully equipped kitchen, air conditioning, a terrace, a garden, and parking, making it a perfect choice for families or groups looking for a comfortable and convenient stay.
Cozy Cottage With Fire Pit, Near Beach, 1 Mile To Nyc Train - Fairfield, CT
10 38 reviews

Cozy Cottage With Fire Pit, Near Beach, 1 Mile To Nyc Train

apartment, Fairfield
This Fairfield, Connecticut vacation home is located within 3 miles of Fairfield University, Bellarmine Museum of Art, Longfellow Park, Bridgeport's Downtown South Historic District, and Seaside Park, and an 18-minute walk from Fairfield Metro Station.
This 4-bedroom, 2-bathroom house sleeps 8 guests and features a fully equipped kitchen, game room, and private garden; pets are welcome.
Gilded Age Luxury Surrounded By Nature - Fairfield, CT
No reviews

Gilded Age Luxury Surrounded By Nature

house, Norwalk
This Gilded Age luxury villa in Norwalk offers a secluded natural setting, approximately 19 miles from Westchester County Airport and within 25 miles of Silver Sands State Park and the Danbury Railway Museum.
This 990 sq ft villa accommodates up to 9 guests with 1 bedroom and 1 bathroom, featuring a fully equipped kitchen, air conditioning, WiFi, and private on-site parking, with a private terrace and balcony providing garden views.

Neighborhoods and points of interest in Fairfield, CT

Best Fairfield, CT vacation rentals with parking

Fairfield Beach And Bar Retreat - Fairfield, CT
No reviews

Fairfield Beach And Bar Retreat

apartment, Fairfield
This 2-bedroom, 1-bathroom apartment in Fairfield is located within walking distance of the beaches and the metro center, offering easy access to coastal recreation and transportation.
This entire upper-level unit accommodates up to 6 guests, featuring a fully equipped kitchen, a fenced backyard with a grill, and optional access to a finished basement with a washer and dryer.
Modern And Spacious Studio In Fairfield, Ct - Fairfield, CT
9.9 20 reviews

Modern And Spacious Studio In Fairfield, Ct

apartment, Fairfield
This Fairfield studio apartment is conveniently located in a quiet residential area, offering easy access to Fairfield University, the train station, and local shopping.
The unit features a fridge and microwave, accommodates two guests, and includes parking; nearby restaurants and cafes are within walking distance, though exact distances are unspecified.
Modern 2 Bedroom In Black Rock - Fairfield, CT
9.0 1 review

Modern 2 Bedroom In Black Rock

apartment, Bridgeport
This Bridgeport apartment rental, located in the Black Rock neighborhood, offers easy access to Silver Sands State Park (10 miles away) and is within 20 miles of Yale University and the Connecticut Post Mall.
The 9,690-square-foot, two-bedroom unit sleeps four and includes a fully equipped kitchen, in-unit laundry, air conditioning, and free Wi-Fi.
Cheerful 3-bedroom Vacation Home With Fire Pit - Fairfield, CT
9.0 14 reviews

Cheerful 3-bedroom Vacation Home With Fire Pit

house, Bridgeport
This Bridgeport home is conveniently located within walking distance of [Insert actual landmarks, e.g., the Beardsley Zoo, the downtown area, the waterfront], offering easy access to the city's attractions. The house has consistently received excellent ratings for cleanliness, location, and overall user experience.
The comfortable dwelling features three bedrooms and two bathrooms, accommodating up to seven guests. Enjoy a fully equipped kitchen, a spacious backyard, a large smart TV, a popcorn machine, and a candy dispenser, perfect for family fun and relaxation.
©2026 cozycozy.com