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

*Pool Open* Designer Home  Hot Tub & Fire Pits - Fairfield, CT
9.7 22 reviews

*Pool Open* Designer Home Hot Tub & Fire Pits

apartment, Fairfield
This Fairfield chalet, situated centrally between Fairfield town centre and Southport, offers easy walking access to both the beach and local restaurants.
Sleeping up to ten guests, this four-bedroom property boasts a chef's kitchen, private pool and spa, spacious recreation room with fireplace, and the option of renting a self-contained annexe next door (additional fee applies).
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.
Modern + Spacious 5br/2ba Home, Renovated Backyard - Fairfield, CT
9.6 5 reviews

Modern + Spacious 5br/2ba Home, Renovated Backyard

apartment, Bridgeport
This West End, West Side property is less than 2km from Bridgeport's Downtown South Historic District and Lafayette Park, and within 3km of the Housatonic Museum of Art and Downtown Cabaret Theatre.
This five-bedroom house, boasting 232 square metres of floor space, comfortably sleeps 12 guests and includes a fully equipped kitchen, terrace, garden, parking, and free Wi-Fi.
*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 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.

Best Fairfield, CT vacation rentals with a pool

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

Designer Villa Bordering  Westport - Fairfield, CT
9.9 18 reviews

Designer Villa Bordering Westport

house, Fairfield
This designer cottage is situated in a tranquil setting near Westport, just minutes from the beach, the town centre, the historic sailing town of Southport, and the train station. The property has received excellent ratings for its location, cleanliness, and overall experience.
This spacious house offers four bedrooms and four bathrooms, accommodating up to six guests. Guests can enjoy a range of amenities, including a heated pool, hot tub, two kitchens, multiple living spaces, a game room, a fire pit, and a bocci court.
Modern Art&architecture Retreat - Fairfield, CT
10 12 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.
Characterful Iconic Weston Lodge. - Fairfield, CT
No reviews

Characterful Iconic Weston Lodge.

apartment, Weston
This tranquil four-bedroom flat, offering a unique getaway experience, is located in a peaceful residential area of Weston, a short distance from the town centre and its shops and restaurants.
This spacious accommodation for six guests boasts air conditioning, a swimming pool, jacuzzi, garden, and parking, with a kitchen equipped with a fridge and dishwasher.
Beautiful Beach Escape In Fairfield - Fairfield, CT
9.0 4 reviews

Beautiful Beach Escape In Fairfield

apartment, Fairfield
This Fairfield apartment is just a two-minute walk from the town centre and a short distance from the beach, making it ideal for exploring the area. It has consistently received excellent ratings for its location, cleanliness, and overall experience.
The property is spacious, with four bedrooms and four bathrooms, comfortably accommodating up to eight guests. It features a well-equipped kitchen, a swimming pool, a garden, and a fitness centre, ensuring a comfortable and enjoyable stay.

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

The B&w Haven 3br Private Office By Li Ferry - Fairfield, CT
8.7 3 reviews

The B&w Haven 3br Private Office By Li Ferry

apartment, Bridgeport
This Bridgeport apartment, situated 13km from Silver Sands State Park and 18km from the Connecticut Post Mall, offers easy access to both coastal and shopping attractions.
The 186 square metre, three-bedroom property sleeps eleven guests and boasts a fully equipped kitchen, free Wi-Fi, on-site parking, a shared garden, and a fireplace; additional cleaning is available fortnightly.
Luxury Cabin For 6 - Stream - Pond - Custom Kitchen - Fairfield, CT
10 1 review

Luxury Cabin For 6 - Stream - Pond - Custom Kitchen

cabin, Redding
This luxury A-frame lodge is located in the wooded outskirts of Redding, Connecticut, offering a secluded natural setting just a short drive from New York City.
This renovated two-bedroom, two-bathroom accommodation boasts a custom chef's kitchen with Miele appliances, a king suite with a wet bar, an upstairs bedroom with two queen beds and a private balcony, and exclusive access to the entire property, including a private pond and stream, and is conveniently located within 5 kilometres of the Discovery Museum, The Cave, Monroe Plaza Shopping Centre and Bethel Plaza Shopping Centre.
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.
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.

Best Fairfield, CT vacation rentals with parking

Sunrise Water Views Fairfield Ct - Fairfield, CT
No reviews

Sunrise Water Views Fairfield Ct

apartment, Fairfield
This four-bedroom apartment is located in Fairfield, Connecticut, just a short walk from Penfield Beach and less than 1.6 kilometres from the town centre. The apartment is ideal for families, with a capacity of eight guests, and is equipped with three cribs, multiple bikes and beach equipment.
The apartment features a fully equipped kitchen, a spacious living room with stunning water views, a back deck with picnic tables, a covered deck, an outdoor shower, a natural gas Weber grill, and a fitness centre. Guests can also enjoy the use of two paddle boards to explore the nearby waters.
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 spacious house is located in Weston, just over 100km from Manhattan, offering easy access to the town centre and its amenities. It has received excellent user, location and cleanliness ratings, ensuring a comfortable and enjoyable stay.
The property has four bedrooms and five bathrooms, comfortably accommodating up to four guests. The house features a range of amenities, including a swimming pool, jacuzzi, sauna, fitness centre, and a fully equipped kitchen, perfect for both relaxation and entertainment.
Cozy Family Home On Quiet Street - Fairfield, CT
9.7 49 reviews

Cozy Family Home On Quiet Street

apartment, Fairfield
This two-bedroom flat is located in the Fairfield Beach district, approximately 1.6 kilometres from town beaches and a ten-minute drive from outdoor recreation.
This newly remodelled residence accommodates up to four guests and features a fully equipped eat-in kitchen with GE appliances, a three-season porch, a fenced yard, WiFi, and a gas BBQ grill.
Westport Beachfront Retreat! *Steps To The Ocean* - Fairfield, CT
10 10 reviews

Westport Beachfront Retreat! *Steps To The Ocean*

apartment, Westport
This charming beach house is located in Westport, Connecticut, just a short walk from the beach and a few minutes' drive from the town centre, train stations, and the I-95. This makes it a great base for exploring the local area and enjoying the beautiful Connecticut coastline.
The property has four bedrooms and two bathrooms, sleeping up to eight guests. It offers a fully equipped kitchen, a spacious living area, a private outdoor space, and a basement with a queen bed and bathroom.
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