Compare Vacation Rentals & Airbnb in Fairfield, CT

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Fairfield, CT vacation rentals
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355 Rentals and Airbnb in Fairfield, CT

Best family friendly Fairfield, CT vacation rentals

Among the 355 accommodations in Fairfield, CT, here are the 4 best family friendly rentals

House ∙ 3 Bedrooms ∙ 8 Guests - Fairfield, CT
No reviews

House ∙ 3 Bedrooms ∙ 8 Guests

house, Trumbull
This detached house, Canoe Brook Cottage, is located in a tranquil residential lake community in Trumbull, Fairfield County, offering direct access to the motor-free Canoe Brook Lake.
This pet-friendly accommodation sleeps up to eight guests across three bedrooms and features dual living spaces, two full kitchens, an expansive screened porch, and an outdoor patio with a gas fire table and grill, providing ample room for families or multi-generational groups.
Southport Shoreline Charm: Elegant Coastal Escape - Fairfield, CT
8.8 5 reviews

Southport Shoreline Charm: Elegant Coastal Escape

apartment, Fairfield
This three-bedroom flat is conveniently located in Southport, Fairfield, just a short 5-minute drive from the beaches and a few minutes from the town centre. The surrounding area offers a range of shops, restaurants, and attractions, making it an ideal base for exploring the local area.
The property features a spacious living area, dining room, and a cosy back room with a large flat-screen TV. It can comfortably accommodate up to seven guests. The apartment is fully equipped with everything you need for a comfortable stay, including a kitchen with a dishwasher, a washing machine, and a dryer, plus a ping pong table in the basement for entertainment.
Summer Hideaway | Close To Beach And Hiking Trails - Fairfield, CT
10 1 review

Summer Hideaway | Close To Beach And Hiking Trails

apartment, Fairfield
This three-bedroom home is located in a peaceful Fairfield neighbourhood, just a short drive from the beach and a local playground. It has received excellent ratings for its cleanliness, location, and overall experience.
The property is ideal for families or groups of up to seven guests. The spacious living area features a fireplace and an open-plan kitchen, while the large garden includes a patio and fire pit for outdoor dining and relaxation.
Fairfield! 5 Bedroom, 3.5 Bath On Cul-de-sac - Fairfield, CT
10 52 reviews

Fairfield! 5 Bedroom, 3.5 Bath On Cul-de-sac

apartment, Fairfield
This spacious, renovated apartment in Fairfield is conveniently located just a short distance from the town centre, universities, and transportation to NYC Grand Central. The apartment boasts excellent user, location and cleanliness ratings, making it a popular choice for travellers.
The apartment has 5 bedrooms and 3 bathrooms, comfortably accommodating up to 12 guests. Amenities include a private heated pool, a well-equipped kitchen, a spacious living area, a family room with a large TV, and a fully furnished garden with outdoor furniture.

Best Fairfield, CT vacation rentals with a pool

Among the 355 accommodations in Fairfield, CT, here are the 4 best rentals with a pool

Sunny Modern 3 Bedroom House Walk To  Beach And Town - Fairfield, CT
No reviews

Sunny Modern 3 Bedroom House Walk To Beach And Town

apartment, Fairfield
This three-bedroom flat is located in Downtown Fairfield, a 14-minute walk from the Fairfield Museum and History Centre and a 10-minute walk from South Benson Marina.
This apartment offers accommodation for six guests with air conditioning, a hot tub, on-site laundry facilities, and essential toiletries.
Fairfield Favorite - Fairfield, CT
10 23 reviews

Fairfield Favorite

apartment, Fairfield
This Fairfield property is situated on a hill overlooking Brooklawn Country Club, offering a peaceful escape from the city bustle just 1.5 km from the centre of Fairfield. The accommodation is set in a quiet and tranquil setting, ideal for a relaxing getaway.
The house is a spacious four-bedroom property, comfortably accommodating up to eight guests. It boasts a modern kitchen, a swimming pool, a sauna, and a fitness centre, ensuring a comfortable and enjoyable stay.
Modern Artist Retreat Near Beach - Fairfield, CT
9.3 47 reviews

Modern Artist Retreat Near Beach

apartment, Fairfield
This Fairfield apartment is conveniently located just a short walk from the beach, shops, historical sites, and a wide selection of restaurants. With excellent user, location, and cleanliness ratings, this property offers a comfortable and enjoyable stay.
The apartment has two bedrooms and one bathroom, comfortably accommodating up to four guests. Amenities include a fully equipped kitchen, air conditioning, a private garden, a swimming pool, a jacuzzi bath, and a separate in-law suite option available for an extra fee.
1br Guest Apt. Suite /Full Bath, Kitchen -Pool/spa - Fairfield, CT
10 7 reviews

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

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.

Frequently Asked Questions about vacation rentals in Fairfield, CT

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

    Fairfield Beach is a classic, offering beautiful sand and views. The Fairfield Museum and History Center provides a great overview of the town's past. Lake Mohegan offers scenic walks and opportunities for water activities. Downtown Fairfield has charming shops and restaurants.
  • What are the best Airbnb and vacation 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 vacation rentals in Fairfield, CT among travelers.

  • Are there unique natural phenomena in Fairfield, Connecticut?

    While Fairfield doesn't have dramatic geological formations, its coastline offers tidal pools teeming with marine life at low tide, especially near Fairfield Beach. The diverse birdlife around Lake Mohegan and the coastline is also noteworthy. The seasonal changes in foliage are beautiful throughout town.
  • What are the most popular Airbnbs in Fairfield, CT?

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

    Comfortable walking shoes are a must, as is sunscreen and a hat, especially during the summer months. Depending on the season, a light jacket or raincoat might be needed. Don't forget your swimwear if you plan on visiting the beach.
  • What are the best vacation rentals with a pool in Fairfield, CT?

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

    Fairfield's events calendar varies, but the annual Memorial Day parade is a significant community event. Check local listings for smaller, seasonal festivals and events throughout the year. The town often hosts concerts and farmers' markets in the warmer months.
  • 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 will vary greatly depending on your choices. Accommodation can range from budget-friendly motels to upscale hotels. Food costs can range from $25 to $75 per day depending on dining choices. Transportation costs depend on whether you rent a car; public transportation is limited. Activities can range from free (hiking, beach visits) to several hundred dollars for more elaborate experiences. A reasonable estimate might be between $150 and $400 per day per person, but this is a broad range.
  • 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 diverse culinary scene. For seafood, try one of the restaurants along the coast. Many restaurants offer New England classics like clam chowder and lobster rolls. There are also many Italian restaurants reflecting the area's history. Specific restaurant names change frequently, so it's best to check current reviews and guides.
  • What are some less-famous attractions in Fairfield, Connecticut that are worth the visit?

    The Pequotsepos Nature Center offers a quieter escape into nature with hiking trails and wildlife viewing opportunities. Exploring the various neighborhoods reveals charming architecture and historical homes. The coastline offers many less-crowded areas for walking and enjoying the views beyond the main beach areas.
  • What are the best activities for engaging with locals and understanding their culture in Fairfield, Connecticut?

    Attending local events like farmers' markets or concerts provides opportunities to interact with residents. Visiting the Fairfield Museum and History Center can give insight into the town's heritage. Simply striking up conversations with people in local shops or restaurants can offer a glimpse into the community's character.
  • What unique natural landscapes and terrain features can travelers explore in Fairfield, Connecticut?

    Fairfield's landscape is a mix of coastline, wetlands, and residential areas. The coastline offers sandy beaches, rocky areas, and tidal pools. Lake Mohegan provides a freshwater environment with walking trails. The town also has several smaller parks and green spaces.
  • How many days are ideal for visiting Fairfield, Connecticut, and what are some itinerary suggestions?

    A long weekend (3 days/2 nights) is sufficient to explore the main attractions. A possible itinerary could include a day exploring Fairfield Beach and downtown, a day at Lake Mohegan and the Pequotsepos Nature Center, and a day for shopping and dining. A longer stay allows for more relaxed exploration and deeper engagement with the community.

Nearby regions

Best Fairfield, CT vacation rentals with a balcony

Luxury Cabin For 6 - Stream - Pond - Custom Kitchen - Fairfield, CT
No reviews

Luxury Cabin For 6 - Stream - Pond - Custom Kitchen

cabin, Redding
This luxury A-frame lodge is located in the wooded outskirts of Redding, Connecticut, offering a secluded natural setting just a short drive from New York City.
This renovated two-bedroom, two-bathroom accommodation boasts a custom chef's kitchen with Miele appliances, a king suite with a wet bar, an upstairs bedroom with two queen beds and a private balcony, and exclusive access to the entire property, including a private pond and stream, and is conveniently located within 5 kilometres of the Discovery Museum, The Cave, Monroe Plaza Shopping Centre and Bethel Plaza Shopping Centre.
Renovated Retreat With Heated Pool - Fairfield, CT
10 2 reviews

Renovated Retreat With Heated Pool

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.
Renovated House Steps Away From The Ocean - Fairfield, CT
9.6 319 reviews

Renovated House Steps Away From The Ocean

apartment, Milford
This house is located in Milford, just a mile from Walnut Beach and The Coastal Center at Milford Point, and within a two-mile radius of Silver Sands State Park and Silver Sands. The house has received excellent ratings for user experience, location, and cleanliness.
The property has three bedrooms and two bathrooms, comfortably accommodating up to six guests. The house offers a range of amenities, including a fully equipped kitchen, a private garden, a terrace, parking, and air conditioning.
Zen, Spacious & Comfy 2 Bed, Lux Beds - Fairfield, CT
10 2 reviews

Zen, Spacious & Comfy 2 Bed, Lux Beds

apartment, Bridgeport
This two-bedroom basement flat is situated in Bridgeport's Brooklawn-St. Vincent neighbourhood, conveniently close to Sacred Heart University and Bridgeport Hospital.
The 2-bedroom property sleeps 5, boasts high-speed internet, a washer/dryer, and a fully equipped kitchen, plus access to a large yard with a swing; nearby attractions include the Bridgeport Downtown South Historic District and Fairchild Wheeler Golf Course.

Best Fairfield, CT vacation rentals with parking

Spacious Studio With Pool Table - Fairfield, CT
8.6 7 reviews

Spacious Studio With Pool Table

studio, Westport
This Westport studio apartment is centrally located, a short drive (approximately 0.8km) from Westport town centre, 1.1km from Compo Beach, and 0.6km from the Westport Country Playhouse.
The 107-square-metre self-contained apartment sleeps four, features a fully equipped kitchenette with microwave, a private entrance, on-site parking for two cars, and amenities including a pool table, iMac, and home theatre system.
Modern Beach Area Vacation Home With Pool - Fairfield, CT
9.2 30 reviews

Modern Beach Area Vacation Home With Pool

apartment, Fairfield
This Fairfield apartment is located on a quiet historic street, just a block away from the lively Post Road, offering easy access to shops, restaurants and the town centre. The property has received excellent ratings for its cleanliness, location and overall experience.
The home is spacious and designed to evoke a relaxed beach atmosphere. Guests can enjoy outdoor dining by the pool, relax in the garden, and make use of the fully equipped kitchen, which includes a dishwasher, fridge, freezer and microwave.
Retro Bridgeport Apartment - Fairfield, CT
9.6 37 reviews

Retro Bridgeport Apartment

apartment, Bridgeport
This apartment in Bridgeport is conveniently located within a kilometre of a Starbucks, bakery, supermarket, and pharmacy, making it a practical choice for travellers. The apartment has received excellent ratings for cleanliness, location, and overall user experience.
The apartment has two bedrooms with queen-size beds and a living room with a pull-out couch, comfortably accommodating up to four guests. It is equipped with air conditioning, parking, internet access, and a kitchen with a fridge, freezer, microwave oven, and dishwasher.
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 apartment in Bridgeport's Black Rock neighbourhood offers a peaceful retreat, situated 16 kilometres from Silver Sands State Park and 21 kilometres from the Connecticut Post Mall.
The 930 square metre property boasts a fully equipped kitchen, in-unit laundry, free Wi-Fi, and comfortably accommodates up to 13 guests.
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