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Best Short term and Weekly rentals in Fairfield, CT
10 5 reviews
Fairfield, CT
10/22 – 10/26
$5791/nighttotal: $23164 (4 )
Paradise Awaits
5 Acre Estate - Sasco Hill
1 2
apartment , Fairfield
This luxury estate sits on Sasco Hill in Fairfield, just steps from Sasco Beach and a short distance from the charming town center. The property boasts excellent user, location, and cleanliness ratings, making it a top choice for travelers seeking a comfortable and enjoyable stay. This spacious home features 5 bedrooms and 5 bathrooms, comfortably accommodating up to 10 guests. The property offers a range of amenities, including a private pool, gardens, a martini lounge, and a dedicated children's suite, ensuring a memorable and relaxing vacation for all.
Fairfield, CT
10/22 – 10/26
$184/nighttotal: $736 (4 )
Studio In Westport
1 2
apartment , Westport
This Westport studio apartment is located a 5-minute walk from the town center and a 15-minute walk from the beach, with public transportation stops just 1 minute away. This independent accommodation for two guests offers air conditioning, internet, and access to a fitness center, with vehicle rental available for exploring the area.
9.6 5 reviews
Fairfield, CT
07/17 – 07/19
$3683/nighttotal: $7366 (2 )
Lake House Cozy To Relax With A Family. 6 Bedroom Very Spacious House.
6 12
apartment , Trumbull
This Trumbull vacation home provides easy access to major highways and is conveniently located near Boothe Memorial Park and the Discovery Museum. This six-bedroom, four-bathroom house comfortably sleeps twelve guests and offers free WiFi, air conditioning, and amenities such as hair dryers and bathtubs in each bathroom; nearby attractions include Beardsley Zoo and the SportsCenter of Connecticut.
Fairfield, CT
10/22 – 10/26
$222/nighttotal: $888 (4 )
Cozy Private 2br/2ba Retreat W/separate Entrance
1 2
apartment , Bridgeport
This newly renovated 2-bedroom, 2-bathroom basement apartment in Bridgeport offers a private entrance and is located in a residential area with convenient access to local amenities. This pet-friendly rental accommodates up to 4 guests and includes a fully equipped kitchen, in-unit laundry, air conditioning, and access to a backyard, with assigned parking available.
8.0 1 review
Fairfield, CT
10/01 – 01/31
$179/nighttotal: $21838 (122 )
Pet-friendly Cottage, 2 Mi To Saugatuck Falls
1 4
cottage , Redding
This secluded 7-acre cottage in Redding offers a private setting with proximity to Saugatuck Falls Natural Area (10,560 feet) and Putnam Memorial State Park and Collis P. Huntington State Park (within 3 miles), with New Haven 29 miles away. This pet-friendly cabin, accommodating up to 4 guests across 700 square feet with 2 bedrooms, features a wood-burning fire pit, BBQ grills, a covered patio, and a loft bedroom, providing a comfortable base for outdoor recreation and day trips.
8.4 6 reviews
Fairfield, CT
10/01 – 01/31
$519/nighttotal: $63318 (122 )
Modern + Spacious 5br/2ba Home, Renovated Backyard
5 4
apartment , Bridgeport
This West End, West Side home is located less than 2 miles from Bridgeport's Downtown South Historic District and Lafayette Park, and within 3 miles of the Housatonic Museum of Art and Downtown Cabaret Theatre. This 2,500-square-foot vacation rental boasts five bedrooms, two bathrooms, sleeps twelve guests, and includes amenities such as free Wi-Fi, a fully equipped kitchen, and a fireplace.
Fairfield, CT
09/25 – 09/28
$397/nighttotal: $1191 (3 )
Modern 2 Bedroom In Black Rock
1 3
apartment , Bridgeport
This Bridgeport apartment rental, located in the Black Rock neighborhood, offers easy access to Silver Sands State Park (10 miles away) and is within 20 miles of Yale University and the Connecticut Post Mall. The 9,690-square-foot, two-bedroom unit sleeps four and includes a fully equipped kitchen, in-unit laundry, air conditioning, and free Wi-Fi.
10 3 reviews
Fairfield, CT
06/27 – 07/04
$414/nighttotal: $2898 (7 )
Fairfield! Spacious 3bd/1ba On A Quiet Cul De Sac
1 2
apartment , Fairfield
This Fairfield apartment rental boasts three bedrooms, one bathroom, and sleeps five guests, offering a private upper-floor location with self check-in via smart lock. The spacious unit features a fully equipped kitchen with granite countertops and stainless steel appliances, a large private deck with a Weber grill, a 65” Samsung Smart TV, Sonos sound system, jacuzzi tub, and in-unit washer/dryer; high-speed Wi-Fi (500+ Mbps) is also included.
9.6 32 reviews
Fairfield, CT
08/16 – 08/28
$196/nighttotal: $2352 (12 )
Westport Barn
1 2
farm , Westport
This Westport, Connecticut farm stay is conveniently located near the Metro-North Railroad station, Compo Beach, and several excellent restaurants. The one-bedroom, one-bathroom guesthouse offers guests exclusive nighttime use, accommodating two people and featuring air conditioning, parking, and Wi-Fi.
10 8 reviews
Fairfield, CT
09/06 – 09/20
$558/nighttotal: $7812 (14 )
Walkable Beach Home W/ Bikes & Bonfire
1 2
apartment , Fairfield
This Fairfield Beach rental is a 5-minute walk from the beach and a 10-minute walk from downtown Fairfield, offering easy access to both the beautiful coastline and local attractions. The apartment has consistently received excellent ratings for its cleanliness, location, and overall experience. The two-bedroom rental comfortably accommodates up to 5 guests with a flexible sleeping arrangement. You'll enjoy a fully equipped kitchen, a private garden, outdoor amenities like a grill, bonfire pit, and ping pong table, and even beach cruiser bikes for exploring the area.
Fairfield, CT
10/01 – 01/31
$568/nighttotal: $69296 (122 )
Westport Summer Escape
1 4
apartment , Westport
This Westport home, ideally located near downtown, offers easy access to shops and restaurants within walking distance. The 4-bedroom, 3-bathroom house sleeps 6, features a spacious slate patio with a fireplace and BBQ, central air conditioning, a fitness center, and ample parking.
Fairfield, CT
10/23 – 10/25
$1998/nighttotal: $3996 (2 )
Westport Summer Retreat: Available 6/21-7/6
6 7
apartment , Westport
This 6-bedroom, 5-bathroom residence in Westport offers convenient access to the town center, beaches, and train station, all within 0.5 miles. This expansive vacation home accommodates up to 12 guests and features a saltwater pool, spa, outdoor TV, recreation room, gym, and wine cellar.
Best family friendly Fairfield, CT Short term rentals
Among the 212 accommodations in Fairfield, CT, here are the 4 best family friendly rentals
9.0 4 reviews
Fairfield, CT
10/22 – 10/26
$1795/nighttotal: $7180 (4 )
Beautiful Beach Escape In Fairfield
1 2
apartment , Fairfield
This Fairfield apartment is conveniently located just two minutes from the downtown area and a short walk to the beach, offering easy access to Fairfield's best restaurants and attractions. The apartment consistently receives excellent ratings for its cleanliness, location, and overall experience. This four-bedroom, four-bathroom home comfortably accommodates eight guests, providing ample space for families or groups of friends. The apartment is equipped with a gourmet kitchen, a spacious backyard, a swimming pool, a fitness center, and parking, ensuring a comfortable and enjoyable stay.
9.6 41 reviews
Fairfield, CT
06/27 – 07/04
$1111/nighttotal: $7777 (7 )
Westport Luxury Family Retreat | Resort Pool Debut
3 2
apartment , Westport
This stylish 3-bedroom home is located on a charming New England street in Westport, just a short distance from Compo Beach and the downtown area. The apartment has earned excellent ratings for location, cleanliness, and overall user experience. This Westport rental is perfect for a family vacation or a group getaway, comfortably accommodating up to five guests. The apartment includes a spacious kitchen, a private patio with a dining table, a home gym, and a backyard with a swing set and slide.
9.7 159 reviews
Fairfield, CT
08/16 – 08/28
$327/nighttotal: $3924 (12 )
Cozy Condo With Yard And Patio. Long-stay Discount Available
1 2
apartment , Fairfield
This Fairfield apartment is conveniently located about 10 miles from Silver Sands State Park and 13 miles from Connecticut Post Mall Shopping Center, making it a great base for exploring the area. The apartment has received excellent ratings for location, cleanliness, and overall user experience, ensuring a comfortable and enjoyable stay. The spacious apartment can comfortably accommodate up to 6 guests in its 3 bedrooms and 2 bathrooms. Guests can enjoy a private patio and yard, a fully equipped kitchen with a dishwasher, and access to free parking and Wi-Fi.
Fairfield, CT
08/06 – 08/09
$929/nighttotal: $2787 (3 )
Bright, Airy Singlefamily Home In Fairfield, Minutes From Fairfield Beach
4 5
apartment , Fairfield
This 4-bedroom house is located in the Tunxis Hill neighborhood of Fairfield, offering convenient access to Sacred Heart and Fairfield University within a 10-minute drive. This 1500 square foot residence accommodates up to 9 guests and features a backyard, air conditioning, and is located minutes from Fairfield Beach and close to cultural attractions like the Barnum Museum.
Best Fairfield, CT lodging with a balcony
8.0 1 review
Fairfield, CT
07/01 – 09/08
$272/nighttotal: $18768 (69 )
The Blue Sapphire: Modern & Stylish 2br W/ 2 King Beds & Full Kitchen
2 2
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.
Fairfield, CT
09/06 – 09/20
$154/nighttotal: $2156 (14 )
2-bedroom Modern Apartment For Relaxing Stays
2 2
apartment , Bridgeport
This 2-bedroom, 1-bathroom apartment is located in Bridgeport's West End, offering easy access to Silver Sands State Park (approximately 4 miles away), The Coastal Center at Milford Point (approximately 4 miles away), Beardsley Zoo (approximately 1 mile away), and the Regina A. Quick Center for the Arts (approximately 1 mile away), as well as being within walking distance to the Hartford HealthCare Amphitheater and Total Mortgage Arena. This pet-friendly rental accommodates up to 4 guests with a king bed and a queen bed, featuring air conditioning, internet, a terrace/balcony, and on-site parking for your convenience.
10 11 reviews
Fairfield, CT
08/06 – 08/09
$888/nighttotal: $2664 (3 )
Renovated Cape Near Beach, With Fire Pit And Bbq, 1 Mile To Nyc Train
3 5
apartment , Fairfield
This Fairfield vacation home, near Sacred Heart University and minutes from Jennings and Penfield Beaches, offers easy access to the Norwalk Aquarium and Beardsley Zoo. This five-bedroom, two-bathroom house sleeps ten, features a fully equipped kitchen, outdoor patio with BBQ, Roku smart TVs, fast Wi-Fi, driveway parking for three cars, and pet-friendly accommodations for dogs under 30 pounds.
9.4 20 reviews
Fairfield, CT
08/16 – 08/28
$799/nighttotal: $9588 (12 )
Grand Fairfield Getaway- 5br Fam-friendly Near I95&shops - Spacious&gracious\n\n
5 2
apartment , Fairfield
This Fairfield home is conveniently located within a 3km radius of Fairfield University, Bridgeport Downtown South Historic District, and Longfellow Park, making it easy to explore the area's attractions. The property has received excellent user ratings, indicating a comfortable and enjoyable stay for guests. This 5-bedroom house can accommodate up to 12 guests, providing ample space for families or groups. The home offers a range of amenities, including a fully equipped kitchen, a garden with barbecue grills, a terrace, and a tennis court, ensuring a relaxing and entertaining stay.
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
10 59 reviews
Fairfield, CT
10/22 – 10/26
$540/nighttotal: $2160 (4 )
The Elijah Sterling House
1 2
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.
10 7 reviews
Fairfield, CT
08/06 – 08/09
$535/nighttotal: $1605 (3 )
Big Family Home | 3br W/ Piano, Deck, Fire Pit
1 5
apartment , Fairfield
This Fairfield, Connecticut apartment rental is centrally located, within a 10-minute walk of Tunxis Hill Park and a short drive from Fairfield University, Fairfield beaches (Penfield and Jennings), and the Fairfield Metro-North train station providing easy access to New York City and New Haven. This three-bedroom, two-bathroom home, perfect for families or groups of up to six, boasts a home office, piano, oversized soaking tub, deck, fire pit, patio, driveway with space for three cars and a universal EV charging station, plus kayaks available for guest use (with agreement and deposit).
10 2 reviews
Fairfield, CT
09/25 – 09/28
$342/nighttotal: $1026 (3 )
Pleasant Wellness Home Bridgeport-2
1 3
apartment , Bridgeport
This 3-bedroom, 1-bathroom apartment is located in a well-connected Bridgeport district, offering easy access to local attractions and transport links, with the Beardsley Zoo approximately 2 miles away and the historic Park City Hospital within 1 mile. This accommodation comfortably sleeps 9 guests and features essential amenities like internet, kitchen, air conditioning, and parking, making it an ideal base for group travel and exploring Bridgeport's offerings.
9.9 20 reviews
Fairfield, CT
06/27 – 07/04
$213/nighttotal: $1491 (7 )
Modern And Spacious Studio In Fairfield, Ct
1 2
apartment , Fairfield
This Fairfield studio apartment is conveniently located in a quiet residential area, offering easy access to Fairfield University, the train station, and local shopping. The unit features a fridge and microwave, accommodates two guests, and includes parking; nearby restaurants and cafes are within walking distance, though exact distances are unspecified.
Neighborhoods and points of interest in Fairfield, CT
Best Fairfield, CT lodging with laundry available
10 3 reviews
Fairfield, CT
07/01 – 07/31
$94/nighttotal: $2820 (30 )
Cozy Master Bedroom W/private Entrance
1 2
apartment , Bridgeport
This 1-bedroom, 1-bathroom apartment in Bridgeport offers a private retreat with a separate entrance and dedicated parking. This accommodation features air conditioning, internet, and a shared kitchen, laundry, and living areas, accommodating up to 2 guests and ideal for traveling professionals.
Fairfield, CT
10/01 – 01/31
$273/nighttotal: $33306 (122 )
Family Home Near Roosevelt Forest & Historic Sites
4 4
apartment , Stratford
This Stratford rental is located less than 1 mile from Roosevelt Forest and Boothe Memorial Park & Stratford Veterans Museum, with easy access to the Merritt Parkway and within a short drive of universities like Yale. This 1580 square foot apartment accommodates up to 8 guests, featuring 4 bedrooms, 2 bathrooms, a full kitchen with a dishwasher, air conditioning, free WiFi, and a step-free entry.
9.7 49 reviews
Fairfield, CT
09/25 – 09/28
$391/nighttotal: $1173 (3 )
Cozy Family Home On Quiet Street
1 3
apartment , Fairfield
This recently remodeled 3-bedroom, 2-bathroom home is located in the Fairfield Beach area, a short walk to Historic downtown Fairfield shopping and dining, and one mile from town beaches. This family-friendly rental offers a fenced yard on a quiet cul-de-sac, a three-season porch, a fully equipped eat-in kitchen with GE appliances, WiFi, and a gas grill, accommodating up to 4 guests with amenities like books and toys for children.
9.9 46 reviews
Fairfield, CT
08/16 – 08/28
$363/nighttotal: $4356 (12 )
The Stone House
1 2
apartment , Easton
This Easton house rental, perfect for families or groups, offers four bedrooms and two bathrooms, comfortably sleeping eight guests, and includes modern amenities such as a dishwasher, microwave, and air conditioning. The property features a spacious open floor plan, a separate apartment for added privacy, and private parking, all within easy reach of Easton's attractions (exact location details require further clarification).
