Fairfield, CT Short term rentals

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Fairfield, CT short term rentals
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Best Short term and Weekly rentals in Fairfield, CT

Best family friendly Fairfield, CT Short term rentals

Among the 212 accommodations in Fairfield, CT, here are the 4 best family friendly rentals

Cozy, Updated Single Family In Fairfield County - Fairfield, CT
9.9 68 reviews
Fairfield, CT
23/10 – 25/10
SG$872/nighttotal: SG$1744 (2 )

Cozy, Updated Single Family In Fairfield County

1 7
apartment , Trumbull
This Trumbull apartment, a short 1.6km drive from Sacred Heart University and the Merritt Parkway, offers easy access to parks, beaches, shopping, and restaurants in Fairfield County.
Sleeping seven guests, this three-bedroom, one-bathroom property features a newly renovated kitchen, spacious backyard with patio and fire pit, family room/office, and covered patio with outdoor dining; private parking is also available.
Luxury Family Retreat With Lake & Comfort. - Fairfield, CT
9.7 43 reviews
Fairfield, CT
17/07 – 19/07
SG$4544/nighttotal: SG$9088 (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.
Beautiful Beach Escape In Fairfield - Fairfield, CT
9.0 4 reviews
Fairfield, CT
27/06 – 04/07
SG$1923/nighttotal: SG$13461 (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.
Westport: Walk To Town, Private Natural Setting, Lovely Neighborhood - Fairfield, CT
9.8 37 reviews
Fairfield, CT
01/10 – 31/01
SG$807/nighttotal: SG$98454 (122 )

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 short term rentals with a balcony

Grand Fairfield Getaway- 5br Fam-friendly Near I95&shops - Spacious&gracious\n\n - Fairfield, CT
9.4 20 reviews
Fairfield, CT
19/12 – 02/01
SG$1290/nighttotal: SG$18060 (14 )

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

5 4
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.
2-bedroom Modern Apartment For Relaxing Stays - Fairfield, CT
Fairfield, CT
19/12 – 02/01
SG$250/nighttotal: SG$3500 (14 )

2-bedroom Modern Apartment For Relaxing Stays

2 4
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.
Renovated Retreat With Heated Pool - Fairfield, CT
10 2 reviews
Fairfield, CT
23/10 – 25/10
SG$1398/nighttotal: SG$2796 (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.
Cozy Condo With Yard And Patio. Long-stay Discount Available - Fairfield, CT
9.7 162 reviews
Fairfield, CT
17/08 – 31/08
SG$418/nighttotal: SG$5852 (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.

Frequently asked questions about short term rentals in Fairfield, CT

  • What attractions should one visit during a week-long stay in Fairfield, Connecticut, United States?

    A week in Fairfield offers plenty! Start with a stroll along the Fairfield Beach, enjoying the Long Island Sound views. Explore the historic Fairfield Museum and History Center to learn about the town's rich past. For nature lovers, a visit to Lake Mohegan is a must, offering walking trails and beautiful scenery. Downtown Fairfield has charming shops and restaurants; consider a visit to the Sherman Green for a relaxing break. If time allows, take a short trip to nearby Southport, known for its picturesque harbour and upscale shops.
  • What are the best short term rentals in Fairfield, CT?

  • What attractions should one visit when spending a month in Fairfield, Connecticut, United States?

    A month gives you ample time to explore Fairfield and its surroundings thoroughly. In addition to the attractions mentioned for a week-long stay, you could explore the various parks and nature reserves, including Jennings Beach and the Lake Mohegan State Park. Consider day trips to nearby towns like Westport or New Haven. Explore the different neighbourhoods, discovering hidden gems and local businesses. You could also dedicate time to specific interests, such as visiting art galleries, exploring the local culinary scene, or participating in community events. Consider a visit to the Pequot Library, a beautiful historic building with a vast collection.
  • What are the best short term rentals with a pool in Fairfield, CT?

  • Can visitors to Fairfield, Connecticut, United States witness any unique natural cycles, like cherry blossom season or autumn colours?

    Yes, Fairfield experiences beautiful autumn colours typically peaking in October and November, transforming the landscape with vibrant reds, oranges, and yellows. While not as renowned for cherry blossoms as some other locations, you can still find some flowering trees in spring, though it's not a major seasonal event like in Washington D.C.
  • What are the best short term rentals with a jacuzzi in Fairfield, CT?

  • What are the most meaningful ways to engage with locals and discover the culture in Fairfield, Connecticut, United States?

    To connect with locals, visit the farmers' markets held regularly throughout the year, offering a chance to interact with vendors and sample local produce. Attend community events, like concerts or festivals at the Sherman Green. Support local businesses by dining at restaurants and shopping at independent stores. Participating in activities at the Fairfield University campus might offer opportunities for interaction with students and faculty. A friendly chat with staff at the Fairfield Museum and History Centre can also provide insight into the local culture.
  • What are the best short term rentals for families and kids in Fairfield, CT?

  • Are there any distinctive cultural activities or hands-on workshops in Fairfield, Connecticut, United States?

    Fairfield offers various cultural activities. The Fairfield Theatre Company hosts regular performances, and the Pequot Library often runs workshops and events. Check local listings for art classes, cooking demonstrations, or other hands-on workshops offered by community centres or local businesses. The Fairfield Museum and History Center may also offer workshops related to local history.
  • What are some secret spots or hidden treasures to visit in Fairfield, Connecticut, United States?

    Some lesser-known spots include the quiet trails within Lake Mohegan State Park, offering peaceful walks away from the main areas. Exploring the backstreets of Southport can reveal charming hidden shops and cafes. The views from the top of the hill overlooking the Long Island Sound from various residential areas offer unexpectedly beautiful panoramas. The specific locations are less about addresses and more about exploring the less travelled paths.
  • What should not be left out of one's suitcase if one is going to Fairfield, Connecticut, United States?

    Pack comfortable walking shoes, as you'll likely be doing a lot of exploring on foot. Layers of clothing are recommended, as the weather can be unpredictable. Sunscreen and a hat are essential, especially during summer months. Don't forget a light rain jacket, as showers can occur unexpectedly. Depending on the time of year, you might need warmer clothing for evenings.
  • What are the most popular festivals in Fairfield, Connecticut, United States?

    Fairfield doesn't have large-scale, internationally renowned festivals. However, local events are held throughout the year. Check local event listings closer to your travel dates for information on specific events, such as those held at the Sherman Green or in Southport. These are usually smaller, community-based events.

Nearby regions

Best Fairfield, CT short term rentals with a kitchen

Gorgeous, Luxury Cape In Westport! - Fairfield, CT
9.8 45 reviews
Fairfield, CT
01/10 – 31/01
SG$589/nighttotal: SG$71858 (122 )

Gorgeous, Luxury Cape In Westport!

3 4
apartment , Westport
This Cape Cod-style house is located in Westport, Connecticut, just a short distance from the beach and the charming downtown area, making it perfect for exploring both the natural beauty and the urban amenities of the town. The accommodation has consistently received excellent ratings for its location, cleanliness, and overall experience.
The house is spread over three floors, offering ample space for up to six guests. It comes equipped with a fully fitted kitchen, a garden, and parking, ensuring a comfortable and enjoyable stay.
Charming Colonial For Events!  Perfect For Family Reunions And Group Getaways! - Fairfield, CT
8.8 10 reviews
Fairfield, CT
17/07 – 19/07
SG$2608/nighttotal: SG$5216 (2 )

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

6 12
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.
Captain House In Black Rock-academic Rental - Fairfield, CT
Fairfield, CT
01/10 – 31/01
SG$447/nighttotal: SG$54534 (122 )

Captain House In Black Rock-academic Rental

3 4
apartment , Bridgeport
This three-bedroom flat is located in Bridgeport's historic Black Rock district, offering waterfront views of Burr Creek and situated 6 kilometres from Silver Sands State Park.
This property, spanning 33 square metres and accommodating up to seven guests, features a kitchen with a fridge, microwave, and dishwasher, air conditioning, a garden, parking, and a laundry room, with a check-out time of 10:00 AM.
Fairfield Beach ⛱Renovated Cape - 3 Bed 2 Bath - Fairfield, CT
9.9 24 reviews
Fairfield, CT
03/08 – 21/08
SG$778/nighttotal: SG$14004 (18 )

Fairfield Beach ⛱Renovated Cape - 3 Bed 2 Bath

2 2
apartment , Fairfield
This charming holiday home is ideally situated in Fairfield, just a short walk from the beach, town centre, and train station, making it an excellent base for exploring all that the area has to offer. The property has received excellent ratings for its location, cleanliness, and overall experience.
The home has three bedrooms and two bathrooms, comfortably accommodating up to four guests. It is fully equipped with modern amenities including air conditioning, a kitchen with a dishwasher, a jacuzzi, a garden, and parking, ensuring a comfortable and enjoyable stay.

Best Fairfield, CT short term rentals with laundry available

Fairfield Beach Summer Rental - Fairfield, CT
8.6 16 reviews
Fairfield, CT
01/07 – 31/07
SG$381/nighttotal: SG$11430 (30 )

Fairfield Beach Summer Rental

3 1
apartment , Fairfield
This Fairfield property is located directly across the street from the beach, within walking distance of the town centre, restaurants, and other beaches. The accommodation has received very good user ratings, with excellent location and cleanliness ratings.
This three-bedroom, two-bathroom house comfortably sleeps eight people, making it ideal for families or groups of friends. The property offers a range of amenities, including a fully renovated kitchen and bathrooms, a washer and dryer, parking for five cars, and all utilities included.
Westport Gem - Walk To Shops, Dining, Town Center, Pet-friendly - Fairfield, CT
10 15 reviews
Fairfield, CT
01/10 – 31/01
SG$816/nighttotal: SG$99552 (122 )

Westport Gem - Walk To Shops, Dining, Town Center, Pet-friendly

2 4
apartment , Westport
This Westport seaside property is a short walk from the Westport Historical Society and Levitt Pavilion, and within 3.2km of the Westport Country Playhouse and Westport Farmers' Market.
The two-bedroom, two-bathroom house sleeps four and offers a fully equipped kitchen with microwave and dishwasher, plus amenities including a washing machine, coffee maker, office space, Smart TV, and a terrace; enjoy easy beach access and stunning sea views.
Charming Beach Apartment - Fairfield, CT
Fairfield, CT
01/07 – 31/07
SG$492/nighttotal: SG$14760 (30 )

Charming Beach Apartment

1 1
apartment , Fairfield
This Fairfield apartment, recently renovated in January 2025, is centrally located within walking distance of Fairfield Beach and the town centre, and directly opposite a park with bocce, volleyball, and tennis courts.
The three-bedroom, one-bathroom flat sleeps four guests and offers amenities including parking, internet access, and air conditioning; pets are welcome.
Cape On The Water - Fairfield, CT
9.9 105 reviews
Fairfield, CT
29/07 – 07/08
SG$465/nighttotal: SG$4185 (9 )

Cape On The Water

2 2
apartment , Bridgeport
This charming Cape Cod house is situated in the peaceful residential area of Black Rock, Bridgeport, just a short distance from Fairfield, with views of Ash Creek and Long Island Sound. The property enjoys excellent ratings for its location, cleanliness, and overall guest experience.
The house has two bedrooms and two bathrooms, comfortably accommodating up to four guests. Amenities include a fully equipped kitchen, a spacious deck overlooking the water, off-street parking, a washer and dryer, fast Wi-Fi, two smart TVs, and a pet-friendly policy for smaller, non-shedding breeds.
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