Compare Vacation Rentals & Airbnb in Fairfield, CT

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Fairfield, CT vacation rentals
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355 Rentals and Airbnb 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

Charming Westport Retreat - Fairfield, CT
9.6 5 reviews

Charming Westport Retreat

apartment, Westport
This Westport house, situated near a river and within easy reach of Westport town centre, offers a peaceful retreat with convenient access to shops and restaurants.
Sleeping up to nine guests, this spacious property boasts a four/five-bedroom layout, three bathrooms, a cook’s kitchen with cathedral ceilings, and a private lawn with direct river frontage; amenities include air conditioning, Wi-Fi, parking, and a dishwasher.
2bdfairfield Work & Relax Space W. Patio+fast Wifi - Fairfield, CT
9.8 101 reviews

2bdfairfield Work & Relax Space W. Patio+fast Wifi

apartment, Fairfield
This two-bedroom flat is located in a peaceful residential area in Fairfield, just a short distance from the bustling town centre. The property has received excellent ratings for its cleanliness, location, and overall experience.
The apartment comfortably accommodates up to five guests and features a spacious living area, a fully equipped kitchen, and a private garden. Guests can enjoy a range of amenities including a fire pit, a picnic table, multiple patios, and a modern entertainment system.
Lovely 5 Bedroom Beach House With Large Backyard - Fairfield, CT
10 11 reviews

Lovely 5 Bedroom Beach House With Large Backyard

apartment, Fairfield
This Fairfield house is situated just a short walk from the beach, the town centre, and the Metro North train station, making it a convenient base for exploring the area. The surrounding neighbourhood is quiet and residential, offering a peaceful retreat from the hustle and bustle of city life.
The house has 5 bedrooms and 3 bathrooms, providing ample space for up to 9 guests. It features a fully equipped kitchen, a spacious living room with a fireplace, a large garden with a patio, and parking for multiple vehicles.
Renovated 3br Apt / Easy Check-in / Familyfriendly - Fairfield, CT
No reviews

Renovated 3br Apt / Easy Check-in / Familyfriendly

apartment, Bridgeport
This three-bedroom Bridgeport West Side apartment, near the Adventure Park at Discovery Museum and South Benson Marina, offers convenient access to Bridgeport's attractions.
The 84 square metre self-catering flat sleeps eight, boasting a fully equipped kitchen, high-speed internet, smart TVs, and a shared garden; self check-in is available.

Best Fairfield, CT vacation rentals with a pool

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

Modern Artist Retreat Near Beach - Fairfield, CT
9.3 47 reviews

Modern Artist Retreat Near Beach

apartment, Fairfield
This Fairfield apartment is conveniently located just a short walk from the beach, shops, historical sites, and a wide selection of restaurants. With excellent user, location, and cleanliness ratings, this property offers a comfortable and enjoyable stay.
The apartment has two bedrooms and one bathroom, comfortably accommodating up to four guests. Amenities include a fully equipped kitchen, air conditioning, a private garden, a swimming pool, a jacuzzi bath, and a separate in-law suite option available for an extra fee.
Waterfront Living In Westport - Fairfield, CT
No reviews

Waterfront Living In Westport

apartment, Westport
This spacious five-bedroom, six-bathroom holiday home in Westport offers a tranquil coastal retreat, situated just a stone's throw from the beach and a short 2-kilometre drive from the town centre.
This well-equipped residence accommodates up to 10 guests and features a swimming pool, jacuzzi, fitness centre, and private parking, providing a comfortable and convenient base for exploring the local area and enjoying seaside activities.
Renovated Retreat With Heated Pool - Fairfield, CT
10 2 reviews

Renovated Retreat With Heated Pool

apartment, Redding
This Redding, Connecticut apartment, situated in the peaceful Redding Centre, is 8km from restaurants such as The Redding Roadhouse, 16km from Ridgefield's shops, and 24km from Collis P. Huntington State Park.
This five-bedroom, three-bathroom property sleeps nine guests and boasts a modern gourmet kitchen with Taj Mahal quartzite countertops, a heated saltwater pool, and a private garden; nearby activities include hiking trails and convenient access to restaurants and shopping.
1br Guest Apt. Suite /Full Bath, Kitchen -Pool/spa - Fairfield, CT
10 7 reviews

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

apartment, Weston
This Weston guesthouse is situated in a suburban area near Westport and New York City, conveniently located for exploring both locations.
The self-contained suite, sleeping up to three guests, boasts a California king bed, sleeper couch, kitchenette with fridge and microwave, private terrace, and access to a heated 15-metre gunite pool and jacuzzi on a three-acre estate.

Frequently Asked Questions about vacation rentals in Fairfield, CT

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

    Fairfield Beach is a classic, offering beautiful sand and views. The Fairfield Museum and History Center provides a great overview of the town's past. Lake Mohegan offers scenic walks and opportunities for water activities. Downtown Fairfield has charming shops and restaurants.
  • 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 formations, its coastline offers tidal pools teeming with marine life at low tide, especially near Fairfield Beach. The diverse birdlife around Lake Mohegan and the coastline is also noteworthy. The seasonal changes in foliage are beautiful throughout town.
  • 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 season, a light jacket or raincoat might be needed. Don't forget your swimwear if you plan on visiting the beach.
  • What are the best vacation rentals with a pool in Fairfield, CT?

  • What famous events or festivals are happening in Fairfield, Connecticut?

    Fairfield's events calendar varies, but the annual Memorial Day parade is a significant community event. Check local listings for smaller, seasonal festivals and events throughout the year. The town often hosts concerts and farmers' markets in the warmer months.
  • What are the best rentals for families and kids 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 range from $25 to $75 per day depending on dining choices. Transportation costs depend on whether you rent a car; public transportation is limited. Activities can range from free (hiking, beach visits) to several hundred dollars for more elaborate experiences. A reasonable estimate might be between $150 and $400 per day per person, but this is a broad range.
  • What are the best rentals or Airbnbs with a jacuzzi 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 one of the restaurants along the coast. Many restaurants offer New England classics like clam chowder and lobster rolls. There are also many Italian restaurants reflecting the area's history. Specific restaurant names change frequently, so it's best to check current reviews and guides.
  • What are some less-famous attractions in Fairfield, Connecticut that are worth the visit?

    The Pequotsepos Nature Center offers a quieter escape into nature with hiking trails and wildlife viewing opportunities. Exploring the various neighborhoods reveals charming architecture and historical homes. The coastline offers many less-crowded areas for walking and enjoying the views beyond the main beach areas.
  • What are the best activities for engaging with locals and understanding their culture in Fairfield, Connecticut?

    Attending local events like farmers' markets or concerts provides opportunities to interact with residents. Visiting the Fairfield Museum and History Center can give insight into the town's heritage. Simply striking up conversations with people in local shops or restaurants can offer a glimpse into the community's character.
  • What unique natural landscapes and terrain features can travelers explore in Fairfield, Connecticut?

    Fairfield's landscape is a mix of coastline, wetlands, and residential areas. The coastline offers sandy beaches, rocky areas, and tidal pools. Lake Mohegan provides a freshwater environment with walking trails. The town also has several smaller parks and green spaces.
  • 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 explore the main attractions. A possible itinerary could include a day exploring Fairfield Beach and downtown, a day at Lake Mohegan and the Pequotsepos Nature Center, and a day for shopping and dining. A longer stay allows for more relaxed exploration and deeper engagement with the community.

Nearby regions

Best Fairfield, CT vacation rentals with a balcony

90-sec Walk To Beach - Walnut Beach Luxury House - Fairfield, CT
10 1 review

90-sec Walk To Beach - Walnut Beach Luxury House

apartment, Milford
This new-build seaside flat in Milford is situated just 6 houses from the beach and close to Silver Sands State Park, offering approximately 242 square meters of living space. This property features a chef's kitchen with a quartz island and GE Profile Smart Air Fryer Oven, a spa-inspired primary suite with a balcony, a dedicated office, and a third-floor rec room with water views, accommodating up to 6 guests.
Stareway To Heaven Su - Fairfield, CT
10 22 reviews

Stareway To Heaven Su

apartment, Fairfield
This Fairfield beachfront flat, situated a short walk from Fairfield's shops and restaurants, offers easy access to Bridgeport and Westport.
The five-bedroom, four-bathroom property sleeps eight, boasting a chef's kitchen, rooftop deck with coastal views, and optional beach cruiser and paddleboard rentals.
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 West End apartment, conveniently located near Beardsley Zoo and the Discovery Museum, offers easy access to Fairfield's attractions.
The 93 square metre (1000 square foot) property sleeps seven guests across four bedrooms and one bathroom, boasting a fully equipped kitchen, garden, terrace, parking, and a bonus games room (additional fee applies) featuring a pool table, darts, arcade game, and table football.
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.

Best Fairfield, CT vacation rentals with parking

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.
House ∙ 3 Bedrooms ∙ 8 Guests - Fairfield, CT
No reviews

House ∙ 3 Bedrooms ∙ 8 Guests

house, Trumbull
This detached house, Canoe Brook Cottage, is located in a tranquil residential lake community in Trumbull, Fairfield County, offering direct access to the motor-free Canoe Brook Lake.
This pet-friendly accommodation sleeps up to eight guests across three bedrooms and features dual living spaces, two full kitchens, an expansive screened porch, and an outdoor patio with a gas fire table and grill, providing ample room for families or multi-generational groups.
Light Filled Zen 3br Penthouse - 7 Min To Westport - Fairfield, CT
No reviews

Light Filled Zen 3br Penthouse - 7 Min To Westport

apartment, Wilton
This Weston penthouse, near Westport (a 7-minute drive, approximately 11.3km), offers easy access to attractions such as Richter Park Golf Course and SUNY Purchase, both within 32km.
This spacious 60 square metre, three-bedroom apartment sleeps nine, boasting a fully equipped kitchen with dishwasher, private entrance, outdoor seating, free Wi-Fi, and a washing machine.
Charming Colonial For Events And Getaways! - Fairfield, CT
10 6 reviews

Charming Colonial For Events And Getaways!

apartment, Bridgeport
This six-bedroom Bridgeport house, sleeping up to twelve guests, offers easy access to local attractions, though precise distances aren't specified.
The 3,300 square foot property boasts two bathrooms, a kitchen, air conditioning, parking, and ample outdoor space including a large front porch, rear porch, and patio; ideal for family reunions or group getaways.
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