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

Charming Westport Retreat - Fairfield, CT
9.6 5 reviews

Charming Westport Retreat

apartment, Westport
This Westport apartment is located in a peaceful and private retreat, within walking distance of the town center and the Westport House & Gardens. It has excellent user, location, and cleanliness ratings.
The apartment has 4 bedrooms, 3 bathrooms, and can accommodate up to 9 guests. It features a spacious living room, a fully equipped kitchen, a private garden with barbecue facilities, and free Wi-Fi. Guests can also enjoy stunning views of the lawn, English gardens, and river frontage from the double-height porch.
Compo Beach Access Gated Private House In Westport - Fairfield, CT
10 1 review

Compo Beach Access Gated Private House In Westport

apartment, Westport
This exclusive, gated 1-acre Gold Coast estate in Westport offers a luxurious experience, situated 14 minutes from Compo Beach and 10 minutes from Downtown Westport.
This 3,280 sq ft residence features 3 bedrooms and 3 bathrooms, accommodating up to 10 guests with amenities including a well-equipped kitchen, a playroom, a ping-pong table, and an 85" TV.
The Elijah Sterling House - Fairfield, CT
10 66 reviews

The Elijah Sterling House

apartment, Trumbull
This Trumbull apartment is conveniently located close to highways for easy access to nearby attractions like state parks, beaches, and the Bridgeport Amphitheater, just a 10-minute drive away.
The Elijah Sterling House, built in 1791, offers a spacious family-friendly layout with a large dining room, a sunroom, and three bedrooms with three full bathrooms, accommodating up to 7 guests.
Hermoso, Limpio Y Tranquilo Lugar Para Relajase - Fairfield, CT
9.9 108 reviews

Hermoso, Limpio Y Tranquilo Lugar Para Relajase

apartment, Bridgeport
This Bridgeport apartment rental is centrally located, offering easy access to Bridgeport's attractions; precise distances to specific landmarks require further clarification.
The 2-bedroom, 1-bathroom unit sleeps 4 guests and includes amenities such as air conditioning, internet, and parking.

Best Fairfield, CT lodging with a balcony

The B&w Haven: Stylish 3br Escape With Private Office By Li Ferry - Fairfield, CT
No reviews

The B&w Haven: Stylish 3br Escape With Private Office By Li Ferry

apartment, Bridgeport
This Bridgeport apartment rental, located in the Brooklawn-St. Vincent neighborhood, offers easy access to Beardsley Zoo, the Discovery Museum, and Fairchild Wheeler Golf Course.
The 2000-square-foot unit features three luxurious bedrooms, one bathroom, a gourmet kitchen, high-speed internet, smart TVs, and a private balcony, accommodating up to six guests.
The Blue Sapphire: Modern & Stylish 2br W/ 2 King Beds & Full Kitchen - Fairfield, CT
9.0 2 reviews

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

apartment, Bridgeport
This two-bedroom Bridgeport apartment rental, located in the Brooklawn-St. Vincent neighborhood, offers convenient proximity to Beardsley Zoo, the Discovery Museum, and Fairchild Wheeler Golf Course.
The 2,000-square-foot residence features a fully equipped kitchen, a spacious backyard, smart TVs, high-speed internet, and sleeps up to five guests comfortably.
Cozy Cottage With Fire Pit, Near Beach, 1 Mile To Nyc Train - Fairfield, CT
10 38 reviews

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

apartment, Fairfield
This Fairfield, Connecticut vacation home is located within 3 miles of Fairfield University, 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 4-bedroom, 2-bathroom house sleeps 8 guests and features a fully equipped kitchen, game room, and private garden; pets are welcome.
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 vacation home is located less than 1.2 miles from Lake Mohegan and its beach, and within 3 miles of Fairfield University and the Fairchild Wheeler Golf Course.
This 3-bedroom, 1.5-bathroom house sleeps 7, features a fully equipped kitchen, in-house laundry, on-site barbecue grills, and a smart TV, perfect for families or groups visiting Fairfield.

Frequently Asked Questions about short term rentals in Fairfield, CT

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

    A week in Fairfield offers plenty to explore! You could spend a day at Lake Mohegan, enjoying its walking trails and scenic views. Another day might be dedicated to exploring the historic Fairfield Museum and History Center, learning about the town's rich past. Downtown Fairfield has some great shopping and dining options, and you could easily spend an afternoon there. Consider a visit to the Pequotsepos Nature Center for a nature walk and wildlife viewing. For a relaxing day, head to Jennings Beach for some sun and sand. A final day trip could be to nearby Southport, with its charming shops and waterfront views.
  • What are the best short term rentals in Fairfield, CT?

  • What attractions should you visit when you spend a month in Fairfield, Connecticut?

    With a month, you can really delve into Fairfield's offerings. In addition to the suggestions for a week-long stay, you could explore more of the town's parks and green spaces, such as Mill River Park. You could take day trips to nearby towns like Westport or Bridgeport, exploring their unique attractions. Consider visiting the Connecticut Audubon Coastal Center at Milford Point for birdwatching. A longer stay allows for more leisurely exploration of the shops and restaurants in Fairfield Center and Southport. You could also plan some longer hikes on the trails around Lake Mohegan or explore the coastline further. Check out local event listings for concerts, farmers' markets, and other activities that might be happening during your stay.
  • What are the best short term rentals with a pool in Fairfield, CT?

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

    Yes, Fairfield experiences beautiful autumn foliage typically peaking in October and November, offering stunning colors. While not as renowned for cherry blossoms as some other areas, you might catch some flowering trees in the spring, particularly around Lake Mohegan and in local parks.
  • 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?

    To connect with locals, visit the farmers' markets held throughout the warmer months. These markets offer opportunities to chat with vendors and sample local produce. Many local restaurants feature seasonal menus highlighting Connecticut ingredients. Attending community events, like concerts in Mill River Park or festivals, offers another chance to interact with residents. Exploring the historic downtown area and engaging with shop owners can also provide a glimpse 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?

    Fairfield offers various cultural activities. The Fairfield Museum and History Center often hosts workshops and exhibits. Check local community centers and art galleries for classes in pottery, painting, or other crafts. The Pequotsepos Nature Center might offer nature-based workshops. Look for seasonal events and festivals that might include hands-on activities.
  • What are some secret spots or hidden treasures to visit in Fairfield, Connecticut?

    While Fairfield is not known for hidden gems in the same way as some larger cities, a lesser-known spot is the charming neighborhood of Southport. It offers a quieter, more residential feel than downtown Fairfield, with beautiful homes and waterfront views. Exploring the various side streets and residential areas can reveal some lovely hidden gardens and architecture.
  • What should not be left out of your suitcase if you are going to Fairfield, Connecticut?

    Pack comfortable walking shoes, as you'll likely be doing a lot of walking, especially if you plan to explore the downtown area and waterfront. Depending on the season, pack layers as the weather can be unpredictable. Don't forget sunscreen and insect repellent, especially during warmer months. A light rain jacket is also advisable.

Nearby regions

Best Fairfield, CT lodging with a kitchen

Historic Loft, Co-work, River View - Fairfield, CT
9.9 365 reviews

Historic Loft, Co-work, River View

apartment, Fairfield
This Westport apartment is just a short drive from Southport Beach, Burying Hill Beach, and the Country Club of Fairfield, offering easy access to both relaxation and entertainment. It has consistently received excellent ratings for cleanliness, location, and overall user experience.
The one-bedroom apartment comfortably accommodates four guests with its 850 square feet of space. Guests can enjoy a fully equipped kitchen, free Wi-Fi, in-house entertainment, and a private jacuzzi, making it the perfect place to unwind after a day exploring Westport.
Historic Colonial Farmhouse - Fairfield, CT
No reviews

Historic Colonial Farmhouse

apartment, Westport
This charming colonial farmhouse is located in Westport, just a short walk from downtown and a 20-minute stroll from the beautiful Compo Beach. The neighborhood offers a peaceful atmosphere while being close to the vibrant energy of downtown Westport.
This spacious 4-bedroom, 2-bathroom home comfortably accommodates 6 guests. Enjoy amenities like a fireplace, air conditioning, a fully equipped kitchen, and parking, along with easy access to a range of activities, including the Westport Country Playhouse, Winslow Park, and the main street of downtown Westport.
Beach And Pool Escape In Luxury Westport Home - Fairfield, CT
No reviews

Beach And Pool Escape In Luxury Westport Home

apartment, Westport
This Westport, Connecticut home is located less than a mile from downtown Westport's shops and restaurants and within 3 miles of two beaches, one public and one private.
This luxurious 4-bedroom, 3-bathroom house sleeps 8, boasting a saltwater pool, 60-jet spa hot tub, outdoor movie setup, fully fenced backyard with fire pit, and a finished basement with playroom and 60" TV.
Lovely Bohemian Loft Downtwn, Amphitheater,seaside Park,metro North,2-10min Walk - Fairfield, CT
9.8 14 reviews

Lovely Bohemian Loft Downtwn, Amphitheater,seaside Park,metro North,2-10min Walk

apartment, Bridgeport
This pet-friendly Bridgeport apartment is centrally located in the Downtown district, a short walk from the Bridgeport Train Station and Baldwin Plaza Shopping Center.
The one-bedroom, one-bathroom unit sleeps two guests and features a fully equipped kitchen, in-unit fireplace, air conditioning, free Wi-Fi, a smart TV, and on-site parking, placing you near attractions like the Beardsley Zoo and Silver Sands State Park.

Neighborhoods and points of interest in Fairfield, CT

Best Fairfield, CT lodging with laundry available

Charming East Norwalk Home. Walk To Calf Pasture. - Fairfield, CT
10 1 review

Charming East Norwalk Home. Walk To Calf Pasture.

apartment, Norwalk
This 3-bedroom, 1-bathroom East Norwalk residence offers a convenient coastal getaway, situated in a walkable neighborhood just a short distance to Calf Pasture Beach and 1.4 miles from the East Norwalk train station. This apartment includes internet, a kitchen, air conditioning, and parking, accommodating up to 6 guests with sun-drenched living spaces ideal for exploring nearby restaurants and shops.
3 Bedrm Apt At Black Rock Suites - Fairfield, CT
9.0 1 review

3 Bedrm Apt At Black Rock Suites

apartment, Bridgeport
This three-bedroom Bridgeport apartment is situated in the Black Rock neighborhood, ten miles from Silver Sands State Park and within 25 miles of Yale University and Tweed-New Haven Airport.
This 1,076-square-foot rental boasts a fully equipped kitchen, in-unit laundry, free Wi-Fi, and accommodates up to thirteen guests, perfect for families or groups visiting Bridgeport.
Charming Beach Apartment - Fairfield, CT
10 2 reviews

Charming Beach Apartment

apartment, Fairfield
This Fairfield, Connecticut apartment is centrally located, within walking distance of Fairfield Beach and the town center, and directly across from a park with bocce, volleyball, and tennis courts.
This three-bedroom, one-bathroom rental sleeps four and features a fully equipped kitchen, air conditioning, parking, internet access, and was recently renovated in January 2025.
Modern 3 Bedroom Apt In The Heart Of Black Rock - Fairfield, CT
9.3 38 reviews

Modern 3 Bedroom Apt In The Heart Of Black Rock

apartment, Bridgeport
This Bridgeport apartment is located in the Black Rock neighborhood, close to beaches, museums, lighthouses, and parks, offering a peaceful escape from the city's hustle and bustle. The apartment is ideal for families or groups of friends, featuring three bedrooms and one bathroom, accommodating up to seven guests.
The apartment includes modern amenities like air conditioning, internet, and a fully equipped kitchen, perfect for preparing meals. Enjoy the quiet location and explore the nearby beaches, parks, and cultural attractions, making this apartment an ideal base for exploring Bridgeport.
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