Vacation Rentals in Fairfield County, CT: Compare 10+ Sites & Save

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33 Best Vacation Rentals in Fairfield County (Starting from $95)

Chickens On-Site Cottage, 2 Mi to Saugatuck Falls
Chickens On-Site Cottage, 2 Mi to Saugatuck Falls
House
Redding, CT, USA
3.1k from Fairfield County center

Accommodations, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Places to stay

1 Bedroom4 Guests
New to Booking
$271
Average price / night
Check Availability
Pet-Friendly Cottage, 2 Mi to Saugatuck Falls
Pet-Friendly Cottage, 2 Mi to Saugatuck Falls
Cottage
Redding, CT, 06896, United States
3.1k from Fairfield County center

AC, Barbecue, Dryer, Fireplace, Free Parking, Heater, Kitchen, Microwave, No Smoking

1 Bedroom4 Guests
8.0

Good

1 reviews

$251
Average price / night
Check Availability
Relaxing 2 Bedroom 2 Bath Apt in Beautiful Nature
Relaxing 2 Bedroom 2 Bath Apt in Beautiful Nature
Apartment
Fairfield County, Connecticut, USA
4.3k from Fairfield County center

Air Conditioner, Parking, Balcony/Terrace, Pet Friendly, Internet, Child Friendly

2 Bedrooms3 Guests
New to Booking
$179
Average price / night
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Relaxing studio in weston woods
Relaxing studio in weston woods
Apartment
Weston, CT, 06883, United States
3.9k from Fairfield County center

AC, Barbecue, Dryer, Free Parking, Heater, Internet, Laundry, Microwave, No Smoking

New to Booking
$132
Average price / night
Check Availability
Cozy Retreat Near Westport
Cozy Retreat Near Westport
House
Fairfield, CT, USA
9.8k from Fairfield County center

View, Security/Safety, Guest Services, Air Conditioner, Parking, Child Friendly

1 Bedroom2 Guests
New to Booking
$180
Average price / night
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Enjoy our 3-story, family-friendly Carriage House Fireplace and outdoor fire pit
Enjoy our 3-story, family-friendly Carriage House Fireplace and outdoor fire pit
House
West Redding, CT, 06896, United States
4.1k from Fairfield County center

AC, Arcade, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen

3 Bedrooms7 Guests
10.0

Exceptional

88 reviews

$627
Average price / night
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Perfect 3-bedroom house with AC in adorable Redding
Perfect 3-bedroom house with AC in adorable Redding
House
Redding, CT, 06896, United States
4.2k from Fairfield County center

AC, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, No Smoking, Patio

3 Bedrooms4 Guests
New to Booking
$479
Average price / night
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Relaxing apartment in weston woods
Relaxing apartment in weston woods
Cottage
Weston, CT, 06883, United States
4.4k from Fairfield County center

AC, Dryer, Heater, Internet, Laundry, No Smoking, Washer

2 Bedrooms3 Guests
New to Booking
$171
Average price / night
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Meeker Hill House - Country Escape w/ Heated Pool
Meeker Hill House - Country Escape w/ Heated Pool
House
Redding, CT, 06896, United States
5.1k from Fairfield County center

AC, Balcony, Barbecue, Crib, Dryer, Fireplace, Free Parking, Heater, Internet

3 Bedrooms6 Guests
6.0

Review score

1 reviews

$1146
Average price / night
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5+ Acres | < 90 Minutes to NYC | Pool + EV Charger | 4BR / 5BA | Sleeps 8 + 2 Kids
5+ Acres | < 90 Minutes to NYC | Pool + EV Charger | 4BR / 5BA | Sleeps 8 + 2 Kids
House
Redding, CT, 06896, United States
5.2k from Fairfield County center

AC, Crib, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen, Microwave

4 Bedrooms8 Guests
New to Booking
$2253
Average price / night
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Historic Designer City Getaway
Historic Designer City Getaway
House
Easton, CT, 06612, United States
5.4k from Fairfield County center

AC, Dryer, Heater, Internet, Laundry, No Smoking, Washer

5 Bedrooms10 Guests
10.0

Exceptional

13 reviews

$1092
Average price / night
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Retreat with Heated Salt Water Pool, 1 Mile to NYC Train
Retreat with Heated Salt Water Pool, 1 Mile to NYC Train
House
Redding, CT, 06896, United States
5.6k from Fairfield County center

AC, Arcade, Balcony, Barbecue, Crib, Dryer, Fireplace, Free Parking, Heater

4 Bedrooms9 Guests
10.0

Exceptional

2 reviews

$493
Average price / night
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Bedroom, bathroom with beautiful shower, second room with work or eating area.
Bedroom, bathroom with beautiful shower, second room with work or eating area.
Apartment
Redding, CT, 06896, United States
5.8k from Fairfield County center

AC, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

1 Bedroom3 Guests
10.0

Exceptional

18 reviews

$273
Average price / night
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Summer getaway with Pool and  Fully stocked Chef's Kitchen
Summer getaway with Pool and Fully stocked Chef's Kitchen
House
Wilton, CT, 06897, United States
6.0k from Fairfield County center

AC, Arcade, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen

5 Bedrooms9 Guests
10.0

Exceptional

2 reviews

$714
Average price / night
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Charming 2-bedroom apartment above horse stables on Tuckers Ridge Farm in Easton
Charming 2-bedroom apartment above horse stables on Tuckers Ridge Farm in Easton
Apartment
Easton, CT, 06612, United States
6.2k from Fairfield County center

AC, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Microwave

2 Bedrooms4 Guests
10.0

Exceptional

2 reviews

$367
Average price / night
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Cozy In-law Garden Suite in Colonial Home
Cozy In-law Garden Suite in Colonial Home
Apartment
Redding, CT, 06896, United States
6.4k from Fairfield County center

AC, Dryer, Free Parking, Heater, Internet, Laundry, Microwave, No Smoking, TV

1 Bedroom2 Guests
New to Booking
$165
Average price / night
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Private Luxury Stay in Expansive Home & Property
Private Luxury Stay in Expansive Home & Property
House
EASTON, CT, 06612, United States
6.4k from Fairfield County center

AC, Arcade, Barbecue, Dryer, Extra Bed, Fireplace, Free Parking, Heater, Internet

6 Bedrooms11 Guests
9.6

Exceptional

4 reviews

$1071
Average price / night
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MidCenturyMod spectacularly Renovated 1 LEVEL living paradise +EV charger
MidCenturyMod spectacularly Renovated 1 LEVEL living paradise +EV charger
House
Redding, CT, 06896, United States
6.8k from Fairfield County center

AC, Balcony, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen

3 Bedrooms6 Guests
10.0

Exceptional

7 reviews

$923
Average price / night
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Luxury Retreat-5BR plus 3rd floor that sleeps 26 adults; 1 mile to town center
Luxury Retreat-5BR plus 3rd floor that sleeps 26 adults; 1 mile to town center
House
Ridgefield, CT, 06877, United States
6.9k from Fairfield County center

AC, Barbecue, Dryer, Fireplace, Fitness Equipment, Free Parking, Heater, Internet, Laundry

6 Bedrooms26 Guests
New to Booking
$645
Average price / night
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Escape to 'River Cottage. Ready for hiking, fishing, or a peaceful break?
Escape to 'River Cottage. Ready for hiking, fishing, or a peaceful break?
Cottage
Weston, CT, 06883, United States
7.3k from Fairfield County center

AC, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Microwave, No Smoking

2 Bedrooms4 Guests
10.0

Exceptional

13 reviews

$431
Average price / night
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Modern 4 bed 4.5 bath w hot tub & heated pool close to beach
Modern 4 bed 4.5 bath w hot tub & heated pool close to beach
House
Weston, CT, 06883, United States
7.3k from Fairfield County center

AC, Balcony, Barbecue, Dryer, Fireplace, Free Parking, Heater, Hot Tub, Internet

5 Bedrooms8 Guests
9.8

Exceptional

6 reviews

$1292
Average price / night
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Luxury 3-Acre Estate: Private Pool, Basketball Court & Designer Interiors
Luxury 3-Acre Estate: Private Pool, Basketball Court & Designer Interiors
House
Weston, CT, 06883, United States
7.4k from Fairfield County center

AC, Barbecue, Crib, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

4 Bedrooms8 Guests
New to Booking
$1150
Average price / night
Check Availability
50%OFF Riverfront WestonHome 1.6 Acers-NYC 1 hour Near estaurants I-95& Parkway
50%OFF Riverfront WestonHome 1.6 Acers-NYC 1 hour Near estaurants I-95& Parkway
House
Weston, CT, 06883, United States
7.7k from Fairfield County center

AC, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Microwave, No Smoking

2 Bedrooms6 Guests
7.4

Good

14 reviews

$202
Average price / night
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Cozy, fully renovated 2BR home with a barn in peaceful Weston, CT for relaxation
Cozy, fully renovated 2BR home with a barn in peaceful Weston, CT for relaxation
House
Weston, CT, 06883, United States
7.8k from Fairfield County center

AC, Dryer, Heater, Internet, Laundry, No Smoking, Washer

2 Bedrooms6 Guests
10.0

Exceptional

1 reviews

$359
Average price / night
Check Availability
Elegant Country Estate with Equestrian Farm
Elegant Country Estate with Equestrian Farm
House
Newtown, CT, 06470, United States
8.3k from Fairfield County center

AC, Arcade, Barbecue, Crib, Dryer, Fireplace, Free Parking, Heater, Internet

6 Bedrooms12 Guests
10.0

Exceptional

90 reviews

$1150
Average price / night
Check Availability
A private room for any traveler
A private room for any traveler
House
Weston, CT, 06883, United States
8.5k from Fairfield County center

AC, Free Parking, Heater, Internet, No Smoking, Outdoor Space, Patio, Pool

1 Bedroom1 Guest
6.0

Review score

4 reviews

$95
Average price / night
Check Availability
Charming 3-bedroom Ranch in Weston Near Westport & Fairfield
Charming 3-bedroom Ranch in Weston Near Westport & Fairfield
House
Weston, CT, 06883, United States
8.8k from Fairfield County center

AC, Barbecue, Dryer, Free Parking, Heater, Internet, Laundry, Microwave, No Smoking

3 Bedrooms6 Guests
10.0

Exceptional

1 reviews

$519
Average price / night
Check Availability

Other accommodation types in Fairfield County:

Pro Tip:
VacationByOwnerRentals aggregates the best inventory from leading travel sites, including Booking.com, Agoda.com, Expedia.com, Vrbo.com, and Airbnb.com. Use our Advanced Filters to compare verified homes, villas, cabins, condos, cottages, vacation rentals, hotels, and eco-friendly stays. Our goal is to help you find the absolute best Vacation Rentals in Fairfield County.

Fairfield County Vacation Rentals on the Map

Frequently Asked Questions

You can explore 33 verified vacation rentals in Fairfield County. Our listings are sourced from a range of trusted providers, giving you access to a wide selection of private homes, apartments, and unique stays—all in one place.

Vacation rental prices in Fairfield County vary depending on the season, property size, and location. Rates typically start from around $95 per night, with higher prices for larger homes or peak travel periods. Comparing available options can help you find a stay that matches both your budget and travel plans.

Most vacation rentals in Fairfield County include fully equipped kitchens, making it easy to prepare meals and enjoy a more flexible stay. This is especially useful for families, longer stays, or travelers who prefer a home-like experience.

Yes, many vacation rentals in Fairfield County welcome pets. Currently, 15 listings allow pets, although specific policies may vary by property. You can filter for pet-friendly options to quickly find suitable accommodations.

For popular travel periods such as holidays or peak seasons, it’s recommended to book your vacation rental 60 to 90 days in advance to secure the best options. During quieter times, you may still find good availability closer to your travel dates.

Vacation rentals in Fairfield County often include amenities such as Fireplace/Heating, Bedding/Linens, and Laundry. These features provide added comfort and convenience, making them a popular choice for travelers seeking more space and privacy.

You can use filters to narrow down your search by criteria such as number of bedrooms, guest ratings, or specific amenities like private pools or beachfront access. This makes it easier to find a property that fits your exact needs and preferences.