Holiday Rentals in Fairfield, CT

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Fairfield, CT holiday rentals
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245 Holiday rentals and Airbnb in Fairfield, CT

Bright, Private 1,000 Sq. Ft. 1-bedroom Apartment - Fairfield, CT
10 83 reviews
Fairfield, CT
29/07 – 07/08
138 €/nighttotal: 1242 € (9 )

Bright, Private 1,000 Sq. Ft. 1-bedroom Apartment

1 2
apartment, Fairfield
This Fairfield apartment is located just a short distance from the Fairfield Town Open Space and a creek, offering a peaceful setting with views of nature. It has consistently received excellent ratings for its cleanliness, location, and overall user experience.
This self-catering property is a second-story suite with a separate entrance, accommodating up to three guests. The apartment features a well-equipped kitchen with a fridge, freezer, microwave oven, and dishwasher, as well as a comfortable living area with a large screen TV, a selection of board games, books, and movies, and a modern bathroom.
A Breezy Beachside Retreat - Fairfield, CT
Fairfield, CT
29/07 – 07/08
219 €/nighttotal: 1971 € (9 )

A Breezy Beachside Retreat

2 2
apartment, Fairfield
This two-bedroom flat in Fairfield offers direct walking access to Penfield Beach and is a short 10-kilometre drive from Westport, with a 112-kilometre journey to New York City.
This pet-friendly apartment accommodates up to four guests and features air conditioning, a kitchen with a freezer and dishwasher, and a garden, providing a convenient base for exploring local attractions like the Fairfield Theatre Company and Beardsley Zoo.
Luxury Family Retreat With Lake & Comfort. - Fairfield, CT
9.7 43 reviews
Fairfield, CT
17/07 – 19/07
3057 €/nighttotal: 6114 € (2 )

Luxury Family Retreat With Lake & Comfort.

6 12
apartment, Trumbull
This spacious house is located in Trumbull, just a short distance from the lake and local attractions, offering a tranquil escape from the hustle and bustle. It consistently receives excellent ratings for its cleanliness, location, and overall guest experience.
The house has six bedrooms and four bathrooms, comfortably accommodating up to twelve guests. The house also features two kitchens, two living rooms, an office, and a patio, making it perfect for families or groups looking for a relaxing getaway.
Lake House Cozy To Relax With A Family. 6 Bedroom Very Spacious House. - Fairfield, CT
9.6 5 reviews
Fairfield, CT
17/07 – 19/07
3185 €/nighttotal: 6370 € (2 )

Lake House Cozy To Relax With A Family. 6 Bedroom Very Spacious House.

6 12
apartment, Trumbull
This Trumbull, Connecticut holiday home is conveniently located near major highways, offering easy access to local parks such as Boothe Memorial Park and museums including the National Helicopter Museum.
The six-bedroom, four-bathroom property sleeps twelve guests and boasts amenities including a jacuzzi, garden, free WiFi, and a fully equipped kitchen with dishwasher; nearby attractions include Beardsley Zoo and the Discovery Museum.
Quiet Westport Studio/travel Nurse Friendly - Fairfield, CT
10 2 reviews
Fairfield, CT
17/08 – 31/08
119 €/nighttotal: 1666 € (14 )

Quiet Westport Studio/travel Nurse Friendly

1 2
house, Westport
This detached dwelling in central Westport is located within 3.2 kilometres of the coastline and beaches, and a short walk from downtown amenities including CVS, Trader Joe's, Sweetgreen and Soul Cycle.
This one-bedroom, one-bathroom property accommodates two guests and offers internet, air conditioning, and parking.
3-bedroom 2-bath House In Norwalk With In-law Suite, Pool, Bbq - Fairfield, CT
8.8 8 reviews
Fairfield, CT
23/10 – 25/10
532 €/nighttotal: 1064 € (2 )

3-bedroom 2-bath House In Norwalk With In-law Suite, Pool, Bbq

3 7
apartment, Norwalk
This apartment in Norwalk is located a mere 400 metres from Earthplace Museum and Lockwood Mathews Mansion Museum, with The SoNo Collection and Center Seven Shopping Centre also within easy reach.
This 3-bedroom, 2-bathroom flat accommodates up to 8 guests and includes a microwave oven, dishwasher, air conditioning, and parking, with a swimming pool available on site.
The Divine At Fairfield Beach - Fairfield, CT
Fairfield, CT
01/07 – 31/07
261 €/nighttotal: 7830 € (30 )

The Divine At Fairfield Beach

1 1
apartment, Fairfield
This Fairfield flat, located on a quiet lane, offers a prime position for enjoying July 4th fireworks and is within 1 kilometre of Penfield Beach and the amenities of downtown Fairfield, providing a peaceful summer retreat.
This property accommodates up to eight guests and features air conditioning, a kitchen, and two bathrooms, with ample natural light throughout, making it ideal for relaxation and unplugging.
Romantic Riverfront Antique Farmhouse In Historic Aspetuck Corners - Fairfield, CT
9.0 16 reviews
Fairfield, CT
01/10 – 31/01
203 €/nighttotal: 24766 € (122 )

Romantic Riverfront Antique Farmhouse In Historic Aspetuck Corners

1 4
manor house, Easton
This charming apartment is situated in the historic Aspetuck Corners, just minutes from Main Street Westport, highways, and the beaches of Long Island Sound. It has received excellent user ratings, a very good location rating, and a good cleanliness rating.
The apartment offers 167 square metres of space with three bedrooms and can comfortably accommodate six guests. It features a modern kitchen, a garden, a fitness centre, parking, and a complimentary bike, perfect for exploring the surrounding area.
Westport Summer Escape - Fairfield, CT
Fairfield, CT
01/10 – 31/01
491 €/nighttotal: 59902 € (122 )

Westport Summer Escape

1 4
apartment, Westport
This Westport, Connecticut house provides easy access to the town's amenities and is a short drive from the beaches and Long Island Sound.
The four-bedroom, three-bathroom property sleeps six guests and features a spacious slate patio with a fireplace/BBQ, an eat-in kitchen, and a family room, ideal for family gatherings.
Stay At Black Rock Harbor - Fairfield, CT
10 69 reviews
Fairfield, CT
03/08 – 21/08
715 €/nighttotal: 12870 € (18 )

Stay At Black Rock Harbor

3 2
apartment, Bridgeport
This apartment is in Black Rock, a short walk from the beach and downtown, making it ideal for exploring the area. It has excellent user, location and cleanliness ratings, ensuring a comfortable stay.
This home has three bedrooms and two bathrooms, comfortably accommodating up to six guests. It has a fully equipped kitchen, a backyard with a picnic table, a Tesla EV charger, and offers flexible check-in and hassle-free departure.
Southport Shoreline Charm: Elegant Coastal Escape - Fairfield, CT
9.6 143 reviews
Fairfield, CT
17/08 – 31/08
388 €/nighttotal: 5432 € (14 )

Southport Shoreline Charm: Elegant Coastal Escape

3 2
apartment, Fairfield
This 3-bedroom house in Fairfield is located just a short distance from the town centre and a 5-minute drive from the beach. It has received excellent ratings for cleanliness, location, and overall experience.
The house spans 9 square metres and comfortably accommodates up to 7 guests. It includes a fully equipped kitchen, a spacious living area, a private garden, and a range of amenities for a comfortable and enjoyable stay, including a ping pong table, sound machines in each bedroom, and a work-from-home friendly setup.
Coastal Lifestyle - Fairfield, CT
10 3 reviews
Fairfield, CT
03/08 – 21/08
433 €/nighttotal: 7794 € (18 )

Coastal Lifestyle

1 2
apartment, Fairfield
This Fairfield apartment is situated just a short distance from the beach and offers stunning views of the salt marsh, a tranquil setting just an hour's train ride from New York City and 25 minutes from New Haven. The property has consistently received excellent ratings for user experience, location, and cleanliness.
The apartment comfortably accommodates up to six guests in its four bedrooms and two bathrooms. It comes equipped with modern amenities such as air conditioning, a dishwasher, and a private deck with scenic views, making it a perfect choice for families or groups looking for a comfortable and relaxing stay.

Best family friendly Fairfield, CT holiday rentals

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

Cozy Condo With Yard And Patio. Long-stay Discount Available - Fairfield, CT
9.7 162 reviews
Fairfield, CT
17/08 – 31/08
281 €/nighttotal: 3934 € (14 )

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

1 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.
2br Flat Above Historic Cider Mill - Fairfield, CT
9.9 343 reviews
Fairfield, CT
17/08 – 31/08
297 €/nighttotal: 4158 € (14 )

2br Flat Above Historic Cider Mill

1 2
apartment, Westport
This charming apartment is situated on top of a renovated historic mill in Westport, just a short distance from several beaches. It has consistently received excellent ratings for location, cleanliness, and overall user experience.
The property offers two bedrooms and one bathroom, comfortably accommodating up to five guests. Enjoy modern amenities like smart TVs, a fully equipped kitchen with a dishwasher, and a washer and dryer, along with unique features like a co-working space and a garden.
Beechmont-charming Colonial For Events And Getaways! - Fairfield, CT
8.0 1 review
Fairfield, CT
17/08 – 31/08
582 €/nighttotal: 8148 € (14 )

Beechmont-charming Colonial For Events And Getaways!

6 2
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.
Westport: Walk To Town, Private Natural Setting, Lovely Neighborhood - Fairfield, CT
9.8 37 reviews
Fairfield, CT
19/12 – 02/01
708 €/nighttotal: 9912 € (14 )

Westport: Walk To Town, Private Natural Setting, Lovely Neighborhood

1 4
apartment, Westport
This spacious apartment is located in a quiet cul-de-sac neighbourhood in Westport, just a short walk from the bus stop for the commuter rail to Grand Central Station in Manhattan and a short drive from the town centre and the beach. It has consistently received excellent ratings for its location, cleanliness, and user experience.
The property offers one-floor living with 186 square metres of space, accommodating up to 8 guests. Amenities include a fully equipped kitchen, a private garden, a jacuzzi, a sauna, a spa, a fitness centre, and a range of entertainment options for all ages.

Best Fairfield, CT holiday rentals with a pool

Among the 245 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
Fairfield, CT
17/08 – 31/08
388 €/nighttotal: 5432 € (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.
Renovated Retreat With Heated Pool - Fairfield, CT
10 2 reviews
Fairfield, CT
23/10 – 25/10
941 €/nighttotal: 1882 € (2 )

Renovated Retreat With Heated Pool

4 7
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.
Beautiful Beach Escape In Fairfield - Fairfield, CT
9.0 4 reviews
Fairfield, CT
27/06 – 04/07
1294 €/nighttotal: 9058 € (7 )

Beautiful Beach Escape In Fairfield

1 2
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.
One Of A Kind Executive Stay In Easton, Ct. - Fairfield, CT
9.4 22 reviews
Fairfield, CT
01/07 – 08/09
1202 €/nighttotal: 82938 € (69 )

One Of A Kind Executive Stay In Easton, Ct.

1 2
apartment, Easton
This Lower Easton Colonial/Contemporary home is situated in a peaceful, secluded area on 3 acres, just a short drive (around 3 km) from the bustling centre of Easton. The property has excellent user, location and cleanliness ratings.
This spacious residence offers five bedrooms and four bathrooms, comfortably accommodating up to 10 guests. Enjoy a range of amenities including a swimming pool, garden, parking, a fully equipped kitchen, air conditioning and a basement entertainment area with a theatre room, game room and bar.

Frequently asked questions about holiday rentals in Fairfield, CT

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

    Fairfield boasts a lovely coastline, so a visit to Jennings Beach or Lake Mohegan is a must. The historic Fairfield Museum and History Center offers a fascinating glimpse into the town's past. For architecture buffs, a stroll through the charming downtown area, admiring the historic buildings, is recommended.
  • What are the best Airbnb and holiday 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 holiday rentals in Fairfield, CT among travellers.

  • Are there any unique natural phenomena in Fairfield, Connecticut?

    Fairfield's location on Long Island Sound provides stunning coastal views and diverse wildlife. While there aren't unique geological phenomena like geysers, the tidal marshes and beaches offer a rich ecosystem to explore. Look out for migratory birds during certain seasons.
  • What are the most popular Airbnbs in Fairfield, CT?

  • What essentials should you bring along to Fairfield, Connecticut?

    Comfortable walking shoes are a must, as you'll likely be doing a fair bit of exploring on foot. Sunscreen and a hat are crucial, especially during the summer months. Depending on the time of year, a light jacket or raincoat might also be useful. Don't forget your swimwear if you plan on visiting the beaches.
  • What are the best holiday rentals with a pool in Fairfield, CT?

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

    Fairfield doesn't host huge, internationally renowned festivals. However, the town often has smaller, local events throughout the year. Check the Fairfield Parks and Recreation Department's website for details on local events and concerts in the summer months. The annual Memorial Day parade is a community highlight.
  • 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 of £150-£300 per person should be sufficient, depending on your accommodation choices and dining preferences. This estimate includes mid-range accommodation, meals at a mix of restaurants and cafes, local transport, and entry fees to attractions. Budget travellers could manage on less, while luxury travellers would need more.
  • 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 varied culinary scene. For fresh seafood, try The Black Bear Saloon or another restaurant along the coast. There are also numerous Italian restaurants reflecting the area's heritage. There isn't one specific 'must-try' Fairfield specialty, but exploring the different cuisines available is part of the experience.
  • What are some less-famous attractions in Fairfield, Connecticut that are worth a visit?

    The Pequotsepos Nature Center offers beautiful walking trails and opportunities for wildlife spotting. Exploring the various smaller parks scattered throughout the town provides a quieter alternative to the more popular beaches. A walk along the Fairfield Beach Road offers beautiful views of the Long Island Sound.
  • What are the best activities for engaging with locals and understanding their culture in Fairfield, Connecticut?

    Visiting local farmers' markets is a great way to interact with residents and sample local produce. Attending a community event, like a concert in a local park, provides opportunities for casual interaction. Simply striking up conversations with people in local shops and cafes can offer insights into the community.
  • What unique natural landscapes and terrain features can travellers explore in Fairfield, Connecticut?

    Fairfield's landscape is primarily coastal, with beaches, tidal marshes, and relatively flat terrain. The coastline offers diverse habitats, from sandy beaches to rocky outcrops. The Pequotsepos Nature Center provides a glimpse into the area's natural environment.
  • How many days are ideal for a visit to Fairfield, Connecticut, and what are some itinerary suggestions?

    Two to three days is a good amount of time to explore Fairfield. A possible itinerary could include a day exploring the beaches and coastline, a day visiting the Fairfield Museum and History Center and downtown, and a day at the Pequotsepos Nature Center or exploring other local parks.

Nearby regions

Best Fairfield, CT holiday rentals with a balcony

The Blue Sapphire: Modern & Stylish 2br W/ 2 King Beds & Full Kitchen - Fairfield, CT
8.0 1 review
Fairfield, CT
09/07 – 31/08
237 €/nighttotal: 12561 € (53 )

The Blue Sapphire: Modern & Stylish 2br W/ 2 King Beds & Full Kitchen

2 1
apartment, Bridgeport
This Bridgeport apartment, situated in the Brooklawn-St. Vincent neighbourhood, offers convenient proximity to attractions such as Beardsley Zoo, the Discovery Museum, and Fairchild Wheeler Golf Course.
The 186 square metre (1999 square foot) property boasts two bedrooms, one bathroom, and sleeps five, featuring a fully equipped kitchen, smart TVs, a terrace, garden access, and high-speed internet.
Private Compo Beach Access Home - Fairfield, CT
9.0 1 review
Fairfield, CT
19/12 – 02/01
678 €/nighttotal: 9492 € (14 )

Private Compo Beach Access Home

3 4
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.
2-bedroom Modern Apartment For Relaxing Stays - Fairfield, CT
Fairfield, CT
22/10 – 26/10
189 €/nighttotal: 756 € (4 )

2-bedroom Modern Apartment For Relaxing Stays

2 2
apartment, Bridgeport
This two-bedroom flat is situated in Bridgeport's West End - West Side, offering convenient access to Silver Sands State Park and The Coastal Centre at Milford Point, with Beardsley Zoo and the Regina A. Quick Centre for the Arts also within proximity.
This accommodation for four guests boasts air conditioning, a balcony, and parking, with nearby attractions including the Hartford HealthCare Amphitheatre and Total Mortgage Arena, making it ideal for exploring local events and natural beauty.
The B&w Haven 5br Home With Yard Theater + Office - Fairfield, CT
8.8 9 reviews
Fairfield, CT
09/07 – 31/08
340 €/nighttotal: 18020 € (53 )

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

5 1
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.

Best Fairfield, CT holiday rentals with parking

Modern House In Black Rock - Fairfield, CT
9.0 11 reviews
Fairfield, CT
29/07 – 07/08
395 €/nighttotal: 3555 € (9 )

Modern House In Black Rock

3 2
apartment, Bridgeport
This Fairfield beachfront property, less than 2km from Longfellow and Seaside Parks and within 5km of Fairfield Museum and History Centre and Fairfield University, offers easy access to Bridgeport's attractions.
This 140 square metre house sleeps seven, boasting four bedrooms, one bathroom, a fully equipped kitchen including a dishwasher and washing machine, plus a garden, parking, and excellent guest reviews.
Bright, Airy Singlefamily Home In Fairfield, Minutes From Fairfield Beach - Fairfield, CT
10 1 review
Fairfield, CT
19/12 – 02/01
447 €/nighttotal: 6258 € (14 )

Bright, Airy Singlefamily Home In Fairfield, Minutes From Fairfield Beach

4 4
apartment, Fairfield
This Fairfield flat is located in the Tunxis Hill district, approximately 1.6 kilometres from Sacred Heart University and Fairfield University, and is also conveniently close to Fairfield Beach.
This 139 square metre residence accommodates up to nine guests with four bedrooms and two bathrooms, offering air conditioning, heating, a hair dryer, an iron, and a garden for outdoor enjoyment, with easy access to the Downtown Cabaret Theatre, Barnum Museum, Fairchild Wheeler Golf Course, and The Adventure Park at Discovery Museum.
2 Bed Apt In Blackrock By Beach - Fairfield, CT
9.0 1 review
Fairfield, CT
29/07 – 07/08
268 €/nighttotal: 2412 € (9 )

2 Bed Apt In Blackrock By Beach

2 2
apartment, Bridgeport
This two-bedroom flat in Bridgeport's Black Rock neighbourhood is conveniently located near the beach, approximately 16 km from Silver Sands State Park and 22 km from the Connecticut Post Mall.
The 1000 square metre property boasts a fully equipped kitchen, air conditioning, Wi-Fi, and accommodates up to six guests, making it ideal for families or groups visiting Bridgeport.
Modern + Spacious 5br/2ba Home, Renovated Backyard - Fairfield, CT
9.6 5 reviews
Fairfield, CT
17/08 – 31/08
477 €/nighttotal: 6678 € (14 )

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

5 2
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.
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