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

Minutes To Walnut Beach, Newly Renovated 3 Bedroom Home - Fairfield, CT
9.8 18 reviews

Minutes To Walnut Beach, Newly Renovated 3 Bedroom Home

apartment, Milford
This three-bedroom apartment is located in Milford, just a short distance from Walnut Beach and attractions like Boothe Memorial Park and Museum. It has received excellent user ratings, making it a popular choice for travellers.
This comfortable apartment can accommodate up to six guests and features a well-equipped kitchen, a garden, parking, and internet access. Guests can also enjoy air conditioning, a washing machine, and a dishwasher, making their stay as pleasant as possible.
2br Flat Above Historic Cider Mill - Fairfield, CT
10 25 reviews

2br Flat Above Historic Cider Mill

apartment, Westport
This Westport apartment, situated in Southport, enjoys a waterfront location within 5km of Southport Beach, Burying Hill Beach, Sasco Hill Beach, and the Country Club of Fairfield, and a 12-minute walk from Southport Station.
The 112 square metre dwelling offers two bedrooms, one bathroom, sleeps five guests, and includes a fully equipped kitchen, in-unit laundry, free WiFi, a garden, parking, and air conditioning.
Quiet Suburban Home Close To Fairfield Beaches And Universities - Fairfield, CT
10 14 reviews

Quiet Suburban Home Close To Fairfield Beaches And Universities

apartment, Fairfield
This Fairfield house, situated less than 1.6km from Lake Mohegan and within 4.8km of Fairfield University, offers easy access to both the lake's beach and the university campus.
Sleeping up to seven guests, this three-bedroom, two-bathroom property boasts a fully equipped kitchen, laundry facilities, a Smart TV, barbecue grills, and is conveniently located near the Fairchild Wheeler Golf Course.
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.

Best Fairfield, CT vacation rentals with a pool

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

*Pool Open* Multi Family Retreat - Nature Spa Fire - Fairfield, CT
10 6 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 New York City via a 45-minute train journey from Grand Central Terminal or a 1-hour drive (approx. 64km).
The property comprises two homes with designer interiors, sleeping up to 14 guests across 6 bedrooms and 4 bathrooms, boasting a swimming pool, jacuzzi, large garden, and chef's kitchen; amenities include a dishwasher, microwave, and large TVs.
Business Or Weekend Escape - Fairfield, CT
9.2 58 reviews

Business Or Weekend Escape

apartment, Stratford
This Stratford holiday home is situated within 3.2 kilometres of the Housatonic River, Perry House, and the Stratford Historical Society's Captain David Judson House, offering easy access to Stratford's historical landmarks.
The one-bedroom property sleeps four guests, boasting a sofa bed, Smart TV, barbecue facilities, and is within easy reach of Academy Hill and Newfield Park, perfect for outdoor recreation.
Modern Art&architecture Retreat - Fairfield, CT
10 8 reviews

Modern Art&architecture Retreat

apartment, Westport
This Westport, Connecticut apartment, an eight-minute drive from the beaches and an hour and 20 minutes from New York City via Metro-North, offers easy access to Westport's restaurants and shops.
Sleeping fourteen comfortably in seven bedrooms and six and a half bathrooms, this luxurious dwelling boasts a private pool, hot tub, media room, and fire pit, alongside high-speed Wi-Fi and smart features.
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 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

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.
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 three-bedroom flat is located in the Brooklawn-St. Vincent neighbourhood of Bridgeport, just a short distance from downtown and major highways. It has received excellent user ratings and is ideal for families or groups of friends.
The apartment spans 139 square metres and comfortably accommodates up to five guests. It is fully furnished and features a modern kitchen, a private terrace, a garden, and parking, making it a perfect choice for those looking for a comfortable and convenient stay in Bridgeport.
The B&w Haven 5br Home With Yard Theater + Office - Fairfield, CT
8.8 10 reviews

The B&w Haven 5br Home With Yard Theater + Office

apartment, Bridgeport
This five-bedroom house in Bridgeport's Brooklawn-St. Vincent neighbourhood is a short walk from the Bridgeport Downtown South Historic District and St Vincent's Medical Center, with Svihra and Lafayette Parks less than 1.6km away.
This 186 square metre family home, sleeping up to 11 guests, boasts a fully equipped kitchen, free WiFi, a balcony, and parking, plus housekeeping is available on request; Bridgeport Station is approximately 2.4km away.
Grand Fairfield Getaway- 5br Fam-friendly Near I95&shops - Spacious&gracious - Fairfield, CT
9.4 20 reviews

Grand Fairfield Getaway- 5br Fam-friendly Near I95&shops - Spacious&gracious

apartment, Fairfield
This Fairfield house is conveniently located within 3km of Fairfield University, Bridgeport Downtown South Historic District, and Longfellow Park, offering easy access to local attractions. It has received excellent user ratings, suggesting a comfortable and enjoyable stay.
The property can accommodate up to 12 guests in its 5 bedrooms and 2 bathrooms, making it ideal for families or groups of friends. Amenities include a fully equipped kitchen, a terrace or balcony, a garden, a tennis court, and parking.

Best Fairfield, CT vacation rentals with parking

Modern 3 Bedroom House In The Heart Of Black Rock - Fairfield, CT
9.4 29 reviews

Modern 3 Bedroom House In The Heart Of Black Rock

house, Bridgeport
Blackrock Suites is located in the Blackrock district of Bridgeport, just a short distance from beautiful beaches, museums, lighthouses, and parks. The area offers a peaceful retreat from the hustle and bustle of the city, with easy access to a variety of attractions.
The suite is a comfortable and spacious three-bedroom apartment that can accommodate up to seven guests. It features a fully equipped kitchen, laundry facilities, air conditioning, parking, and internet access, ensuring a comfortable and convenient stay.
Greenfield Hill Fairfield Horse Country Getaway - Fairfield, CT
No reviews

Greenfield Hill Fairfield Horse Country Getaway

farm, Fairfield
This charming antique barn cottage is located in the historic Greenfield Hill district of Fairfield County, Connecticut, just a short distance from Sasco Creek and Fairfield's town centre. The cottage is a unique and cosy New England barn conversion offering a true taste of Connecticut country living.
The cottage has five bedrooms and two bathrooms, comfortably sleeping six guests. The property offers a range of amenities including a garden, fire pit, and nature trails, along with a fully equipped kitchen and air conditioning.
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 situated in a peaceful residential area, conveniently located near Fairfield University and within easy reach of local shops and train stations providing access to wider Connecticut.
The self-contained apartment sleeps two guests and includes a fridge, microwave, and parking, offering a tranquil base for exploring Fairfield and its surroundings.
Walkable Beach Home W/ Bikes & Bonfire - Fairfield, CT
10 8 reviews

Walkable Beach Home W/ Bikes & Bonfire

apartment, Fairfield
This Fairfield apartment is a short walk from both the beach and the town centre, making it ideal for exploring the area. It has excellent ratings for location, cleanliness and overall experience.
The property has two bedrooms and a bathroom, plus a third room that can be used as an extra bedroom, making it suitable for groups of up to five guests. You'll find everything you need for a comfortable stay, including a fully equipped kitchen, outdoor space with a barbecue and fire pit, and even paddle boards for exploring the water.
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