Holiday Rentals in Fairfield

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Fairfield holiday rentals
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Fairfield holiday rentals: compare the best deals

Best family friendly Fairfield holiday rentals

Among the 245 accommodations in Fairfield, here are the 4 best family friendly rentals

Modern + Spacious 5br/2ba Home, Renovated Backyard - Fairfield
9.6 5 reviews
Fairfield
12/19 – 01/02
HK$5635/nighttotal: HK$78890 (14 )

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

5 4
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.
Paradise Awaits
5 Acre Estate - Sasco Hill - Fairfield
10 5 reviews
Fairfield
10/22 – 10/26
HK$39127/nighttotal: HK$156508 (4 )

Paradise Awaits 5 Acre Estate - Sasco Hill

1 2
apartment , Fairfield
This luxury estate is situated on Sasco Hill in Fairfield, just a short walk from Sasco Beach and the Long Island Sound, offering a peaceful retreat with stunning views. The property has received excellent ratings for location, cleanliness, and user experience, making it a popular choice for travellers.
The five-bedroom house comfortably sleeps up to ten guests, ideal for families or groups of friends. With an Olympic-sized swimming pool, twin cabanas, a spacious den, a martini lounge, and a dedicated children's suite, the estate provides a luxurious and comfortable stay with plenty of entertainment options.
The "Grant" Estate - Fairfield
10 1 review
Fairfield
06/27 – 07/04
HK$10027/nighttotal: HK$70189 (7 )

The "Grant" Estate

5 2
apartment , Fairfield
This five-bedroom, four-bathroom colonial house in Fairfield, Connecticut, is situated near Westport, a 16km drive from Long Island Sound beaches and surrounded by forests offering hiking, fishing, and rock climbing opportunities.
The 2-acre property boasts a heated outdoor pool, hot tub, chef's kitchen with a 4.5-metre marble island, basement gym with Peloton and Nintendo Switch, EV charging, and accommodates up to ten guests.
House In Westport, Mid And Long Term Available - Fairfield
Fairfield
10/22 – 10/26
HK$7849/nighttotal: HK$31396 (4 )

House In Westport, Mid And Long Term Available

4 2
apartment , Westport
This four-bedroom, two-bathroom flat in Westport is located on a quiet residential street, just a 2-kilometre drive from Compo Beach, 800 metres from downtown Westport's shops and restaurants, and a 10-minute drive to the Westport train station for direct access to London.
This property accommodates up to eight guests and features bright, open living spaces with hardwood floors, a living room fireplace, a fully equipped kitchen, and outdoor areas for relaxation.

Best Fairfield holiday rentals with a pool

Among the 245 accommodations in Fairfield, here are the 4 best rentals with a pool

Very Special Getaway Home - Fairfield
Fairfield
10/01 – 01/31
HK$8414/nighttotal: HK$1026508 (122 )

Very Special Getaway Home

3 4
apartment , Weston
This newly renovated barn-style house is situated on a ridge overlooking the trees in Southern Connecticut, offering both tranquil privacy and easy access to Weston's town amenities.
The spacious home features three bedrooms and three bathrooms, comfortably accommodating up to six guests. The property boasts a private pool, hot tub, and a well-equipped kitchen, ensuring a comfortable and enjoyable stay.
1br Guest Apt. Suite /Full Bath, Kitchen -Pool/spa - Fairfield
10 6 reviews
Fairfield
08/17 – 08/31
HK$3514/nighttotal: HK$49196 (14 )

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

1 2
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.
6-bedroom House With Fitness Room And Pool In Westport - Fairfield
Fairfield
10/22 – 10/26
HK$21171/nighttotal: HK$84684 (4 )

6-bedroom House With Fitness Room And Pool In Westport

7 2
apartment , Westport
This spacious 604 square metre residence in Westport offers 7 bedrooms and 8 bathrooms, accommodating up to 14 guests with a private swimming pool, outdoor pavilion with a fireplace, and an on-site fitness room.
Conveniently located near the Country Club of Fairfield and Gateway Shopping Centre, this property provides easy access to golf courses, shopping, and entertainment at the Pitt Centre and Total Mortgage Arena, with pets and families welcome.
Spacious Cottage Loft - Fairfield
10 107 reviews
Fairfield
10/22 – 10/26
HK$1701/nighttotal: HK$6804 (4 )

Spacious Cottage Loft

1 2
apartment , Bridgeport
The Spacious Cottage Loft is located in Black Rock, a charming seaside neighbourhood in Bridgeport, Connecticut, set on the grounds of a historic Victorian house dating back to the 1840s. The cottage has received excellent ratings for location, cleanliness, and user experience, making it a popular choice for travellers.
The cottage has one bedroom and one bathroom, comfortably accommodating two guests. It offers a range of amenities including a fully equipped kitchen, two smart TVs, a dedicated workspace, a private patio, and access to a swimming pool during the warmer months.

Frequently asked questions about holiday rentals in Fairfield

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

    Fairfield offers a charming blend of history and nature. The Fairfield Museum and History Center is a great place to start, showcasing the town's rich past. For a dose of nature, Lake Mohegan offers lovely walking trails and scenic views. The town green, a historic central space, is also a must-see, often hosting community events.
  • What are the best Airbnb and vacation rentals in Fairfield?

    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 among travelers.

  • Are there unique natural phenomena in Fairfield, United States?

    While Fairfield doesn't boast dramatic natural wonders like geysers or massive canyons, its location offers appealing natural beauty. The coastline provides opportunities for birdwatching, and the varied landscapes around Lake Mohegan offer pleasant hiking and walking trails. The changing seasons bring different colours and textures to the area.
  • What are the most popular Airbnbs in Fairfield?

  • What essentials should you bring along for a trip to Fairfield, United States?

    Pack comfortable walking shoes, as you'll likely be doing a fair bit of exploring on foot. Depending on the season, bring layers of clothing, as the weather can be unpredictable. Sunscreen, a hat, and sunglasses are recommended, especially during summer. Don't forget your camera to capture the beautiful scenery.
  • What are the best vacation rentals with a pool in Fairfield?

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

    Fairfield hosts various local events throughout the year. Information on specific dates and events is best found closer to your travel dates through local listings. However, many smaller community events and farmers' markets take place regularly in the town green.
  • What are the best rentals for families and kids in Fairfield?

  • Where can you find the best restaurants serving local dishes in Fairfield, United States, and what are the must-try specialties?

    Fairfield has a variety of restaurants. While there aren't specific 'Fairfield' specialties, many restaurants offer fresh seafood given the proximity to the coast. Checking local review sites closer to your travel dates will give you the most up-to-date information on highly-rated establishments.
  • What are the best rentals or Airbnbs with a jacuzzi in Fairfield?

  • What are some less-famous attractions in Fairfield, United States that are worth a visit?

    The smaller parks and nature trails around town offer a peaceful escape. Exploring the residential streets can reveal charming architecture and hidden gems. Many local shops and businesses offer a glimpse into the community's character.
  • What are the best activities for engaging with locals and understanding their culture in Fairfield, United States?

    Attending local events at the town green is a great way to interact with residents. Visiting local shops and businesses allows for casual conversations with owners and staff. Simply exploring the town and striking up conversations with people you encounter can provide insights into the local culture.
  • What unique natural landscapes and terrain features can travellers explore in Fairfield, United States?

    Fairfield's landscape is a mix of coastal areas, residential neighbourhoods, and smaller parks. Lake Mohegan provides a significant natural area for walking and enjoying the scenery. The coastline offers views of Long Island Sound.
  • How many days are ideal for a visit to Fairfield, United States, and what are some itinerary suggestions?

    A long weekend (3-4 days) is sufficient to explore Fairfield's main attractions. A possible itinerary could include: Day 1: Fairfield Museum and History Center, Town Green; Day 2: Lake Mohegan, exploring local shops; Day 3: Coastal walk, relaxation.

Nearby regions

Best Fairfield holiday rentals with a balcony

Fairfield Cottage -Top Rated Gem, Fire Pit, Near Beach, 90 Min To Nyc - Fairfield
9.7 3 reviews
Fairfield
07/29 – 08/07
HK$4873/nighttotal: HK$43857 (9 )

Fairfield Cottage -Top Rated Gem, Fire Pit, Near Beach, 90 Min To Nyc

3 2
house , Fairfield
This charming cottage is located in Fairfield, just 18 kilometres from Silver Sands State Park, 22 kilometres from Connecticut Post Mall Shopping Centre, and 32 kilometres from The Yale Bowl, offering a peaceful retreat away from the hustle and bustle. It has consistently received excellent ratings for location, cleanliness, and overall user experience.
The cottage features three bedrooms and one bathroom, spanning 130 square metres and comfortably accommodating up to six guests. It boasts a fully equipped kitchen, private patio, air conditioning, complimentary Wi-Fi, and private parking, along with a garden and outdoor play equipment for families.
Cozy Cottage With Fire Pit, Near Beach, 1 Mile To Nyc Train - Fairfield
10 36 reviews
Fairfield
07/29 – 08/07
HK$5941/nighttotal: HK$53469 (9 )

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

3 2
apartment , Fairfield
This Fairfield property is situated within 5km of Fairfield University, the 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 four-bedroom, two-bathroom house sleeps eight guests and boasts a fully equipped kitchen (fridge, microwave, dishwasher), air conditioning, a garden, parking, Wi-Fi, and an on-site games room; pets are welcome.
Charming Colonial For Events!  Perfect For Family Reunions And Group Getaways! - Fairfield
8.8 10 reviews
Fairfield
08/03 – 08/21
HK$9424/nighttotal: HK$169632 (18 )

Charming Colonial For Events! Perfect For Family Reunions And Group Getaways!

6 2
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.
Cozy Condo With Yard And Patio. Long-stay Discount Available - Fairfield
9.7 162 reviews
Fairfield
08/17 – 08/31
HK$2551/nighttotal: HK$35714 (14 )

Cozy Condo With Yard And Patio. Long-stay Discount Available

3 2
apartment , Fairfield
This Fairfield apartment is conveniently located just 10 miles from Silver Sands State Park and 13 miles from the Connecticut Post Mall Shopping Center, offering a great base for exploring the area. The property has consistently received excellent ratings for location, cleanliness, and overall user experience.
This three-bedroom apartment can comfortably accommodate up to six guests. It features a fully equipped kitchen, a private patio, a garden, and free parking, making it a great choice for families or groups looking for a comfortable and convenient stay.

Best Fairfield holiday rentals with parking

Modern Apartment In Black Rock- - Fairfield
10 4 reviews
Fairfield
07/29 – 08/07
HK$2168/nighttotal: HK$19512 (9 )

Modern Apartment In Black Rock-

1 2
apartment , Bridgeport
This Black Rock, Bridgeport flat is conveniently located near Bridgeport's Downtown South Historic District and beautiful beaches, offering easy access to attractions such as the Connecticut Audubon Birdcraft Museum and the Discovery Museum.
The 83 square metre (893 square feet) one-bedroom, one-bathroom apartment sleeps four guests and includes amenities such as free internet, parking, air conditioning, and a kitchen with a fridge and microwave; nearby water activities, including motor boating, are also available.
4 Mi To Beach & Dtwn! Charming Fairfield Home - Fairfield
Fairfield
12/19 – 01/02
HK$7343/nighttotal: HK$102802 (14 )

4 Mi To Beach & Dtwn! Charming Fairfield Home

4 4
apartment , Fairfield
This apartment is situated in Fairfield's Tunxis Hill district, offering convenient access to Fairfield University (3.2 kilometres), downtown Bridgeport (6.4 kilometres), and local beaches.
This 139 square metre flat accommodates up to nine guests with four bedrooms and two bathrooms, featuring a well-equipped kitchen, air conditioning, a garden, and parking, alongside outdoor dining facilities and a fire pit for entertaining.
Charming 2-bedroom Apartment In Delightful Bridgeport With Wifi - Fairfield
Fairfield
07/01 – 07/31
HK$1427/nighttotal: HK$42810 (30 )

Charming 2-bedroom Apartment In Delightful Bridgeport With Wifi

2 1
apartment , Bridgeport
This Bridgeport apartment, situated in the Brooklawn-St. Vincent neighbourhood, is an 11-minute walk (approximately 0.8 km) from Svihra Park and a 2-minute drive (approximately 0.3 km) from Bridgeport's Downtown South Historic District.
The two-bedroom, one-bathroom flat offers on-site parking, a fully equipped kitchen, and sleeps up to two guests, with amenities including towels, bedding and heating; nearby attractions include the Bridgeport Bluefish Baseball Club and Hartford HealthCare Amphitheater.
Modern + Spacious 5br/2ba Home, Renovated Backyard - Fairfield
9.7 27 reviews
Fairfield
10/01 – 01/31
HK$4458/nighttotal: HK$543876 (122 )

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

1 4
apartment , Bridgeport
This five-bedroom, two-bathroom house in Bridgeport offers excellent accommodation for up to 12 guests, situated within walking distance of Seaside Park, Captain's Cove Seaport, and Beardsley Zoo.
The property features two fully equipped kitchens, two living rooms, a private garden with parking, high-speed internet, and is newly renovated throughout.
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