Find Vacation Rentals in Fairfield (CT)

Highlights Fairfield (CT)

  • Wildlife sanctuary
  • Long Island Sound beaches
  • Historic district
  • Small town
  • Peaceful getaway

Best Vacation Rentals in Fairfield (CT)

Guests agree: these stays are highly rated for location, cleanliness, and more.
Fairfield, Fairfield County
Vacation Rental • 3197 ft² • 5 Bedrooms
(6 reviews)
Location, Location, Location. Covered in ivy, this beautiful English Tudor is perfectly sited on the Old Post Road only 1 block to downtown Fairfield with restaurants, theatre, shopping and a Metro North station (1 hour to NYC). Or walk 3 blocks the other way to Fairfield's private Penfield Beach with pavilion, lockers/showers and concessions.The Home is grand and welcoming ensuring the perfect stay:- lush landscaping and private heated pool- designer Kitchen with marble counters, seating island, stainless steel appliances- cozy Living Room with fireplace and large flat screen TV- elegant D...
from $1,003 / night
Fairfield, Fairfield County
Vacation Rental • 2390 ft² • 3 Bedrooms
(4 reviews)
Stunning direct waterfront beach house with sandy beach renovated in 2016! Large family room with built-ins leads to amazing patio for relaxing. All three bedrooms boast high ceilings. Master bedroom has an amazing water view and large sitting deck to capture beach breezes. Custom commercial style kitchen (Sub-Zero fridge & Viking range). Three full updated bathrooms. Plenty of parking. Six minute Uber from Fairfield train station to house.
from $750 / night
Fairfield, Fairfield County
Vacation Rental • 10 Guests • 5 Bedrooms
(8 reviews)
State-of-the-art home remodeled in 2014, available weekly.- 5 bedrooms, 3 full baths, granite counter tops, dishwasher, microwave oven, washer and dryer, and central air conditioning. - Sliding doors lead to upper and lower balconies on both sides of the house which provide panoramic views of Fairfield Beach and Long Island Sound including its historic lighthouse, and on a clear day a view of Long Island itself (approximately 18 miles away).- A private beach only steps away from the water for residents and their guests.- An outdoor grill and table are provided on the large beachside dec...
from $924 / night

Prices and availability

Current Vacation rental prices Fairfield (CT)

$519for 10 Jun - 17 Jun
$593 annual average
Average price per week

Current vacation rental availability Fairfield (CT)

39%for 10 Jun - 17 Jun
26% annual average
Percentage of available rentals

Vacation rentals in Fairfield

A charming town on the Long Island Sound

Fairfield, Connecticut is a peaceful and affluent small-town set on a part of the Long Island Sound referred to as the “Gold Coast of Connecticut.” The town is consistently ranked as one of the best places to live in the United States, and is considered one of the prettiest towns in New England. Fairfield features a five-mile shoreline with five different beaches, as well as several parks, wildlife sanctuaries, museums, entertainment venues, top-rated restaurants, bars, and historic sites. With so much to do and see, the town is a fantastic destination for couples, families, or groups of friends traveling together.

Finding your perfect Fairfield accommodation

Ranked among the best towns in New England, you’ll truly get to embrace the New England lifestyle with a stay at a vacation rental in Fairfield. The town is home to countless vacation rentals, available in varying sizes, locations, and design features. Families and large groups can opt for an oversized vacation rental with a spacious yard and enough bedrooms for everyone. Stay in a leafy neighborhood surrounded by trees and walking paths, or opt to stay closer to the downtown area within walking distance of restaurants and shops. The majority of vacation rentals in this area come equipped with modern amenities, full kitchens, and high-speed Wi-Fi. Pet-friendly accommodations are available for those traveling with pets.

Holidays in Fairfield

The area and getting around

Arriving in Connecticut’s Gold Coast

The town of Fairfield sits on the southwest corner of Connecticut, along the Gold Coast. It’s only 50 miles from New York City and easily accessible from I-95 and the Merritt Parkway. The closest airport is Sikorsky Memorial Airport, which is just 7 miles outside of town. Arriving to Fairfield by train is an option for visitors, as the town has three train stations that extend from New Haven to New York.

Getting around the town

Getting around by bike or by car are the preferred ways to navigate through the town of Fairfield. There are several bike paths throughout the town, making it easy to get from place to place by bike. The downtown area of Fairfield is small and walkable, but getting around to attractions and places outside the downtown area is best done by car. Taxis and car rental services are available.

Travelers and activities

Fairfield for Couples

Fairfield is full of romantic date-night options. Head to the Barcelona Wine Bar with your significant other for an upscale menu of Latin-style cuisine and drinks in an ambient setting. Another classic Fairfield date-night option is Brick+Wood, a restaurant that serves delicious and authentic Italian cuisine. All the food is made from scratch using fresh ingredients and the menu features some ultra-unique, must-try offerings.

Fairfield for Families

Fairfield is a fantastic destination for families of all ages. Visit the Maritime Aquarium at Norwalk for real-life encounters with an abundance of sea creatures from the Long Island Sound. The aquarium houses a wide variety of sea life from around the world, hands-on touch tanks for kids, and a 4D theater. Enjoy a day spent in nature with the whole family at Roy and Margot Larson Wildlife Sanctuary. The area spans over 155 acres and is home to an array of wildlife, flora and fauna, and over 7 walking trails. Kids will love trying to spot some of the more commonly seen creatures around the park, such as frogs, turtles, deer, and ducks.

In July 2006, Money magazine ranked Fairfield as the ninth-best place to live in the USA and the overall best place to live in New England.

Top 5 travel tips in Fairfield

1. Visit The Philip Johnson Glass House

The Glass House was built in 1949 by famed architect, Philip Johnson. The incredible all-glass house is set on a vibrant green 47-acre estate and is a must-see while in the area. The entire exterior of the house is comprised of floor-to-ceiling sheets of glass held together by steel beams. It is considered to be one of the first most noteworthy works of modern architecture in the world, and is the first of fourteen structures that Johnson built on his estate over the span of his fifty years living there.

2. Spend an afternoon at Jennings Beach

This is one of the largest beaches in Fairfield with over 27-acres of golden, sandy shores and unmatched views of the Long Island Sound. The beach has volleyball nets, bathroom facilities, concession stands, food trucks, and a boardwalk. It’s a great place for families, couples, or groups to gather and soak up some sun rays, to enjoy a swim, or to go for a long sunset walk.

3. Visit Fairfield’s most impressive museum

For a small town, Fairfield boasts an impressively good history museum. The Fairfield Museum and History Center features over 13,000 square feet of exhibition galleries, an 80-seat theater, a library, educational rooms for children, a museum shop, and more. The museum features a variety of events and programs throughout the year for kids and families.

4. Go rock climbing

Whether you’re a seasoned rock climber or you’ve never tried it before, Rock Climb Fairfield is an excellent place for a climbing adventure. The indoor climbing center features several rock climb walls of varying levels of difficulty, some of which reach up to 40 feet high. There are different types of features for advanced rock climbers, such as bouldering walls, top ropes, hang boards, campus boards, and more. Get the whole family in on the fun and test out your rock climbing skills!

5. Stroll through Fairfield’s old town district

The old town center of Fairfield is a stretch of road comprised of over 75 historic buildings, many of which date back to the 18th century. This area features the town hall, the public library, and a handful of charming old homes. Make sure to stop by the Rising Sun Tavern, which was built in 1783, and The Silliman House, which dates back to 1791.

FAQs: Vacation Rentals in Fairfield (CT)

How much does it cost to book a vacation rental in Fairfield?

At an average cost of $465 per night, Fairfield lies at the upper end of the price range for vacation rentals in the USA.

During which months are vacation rentals cheaper in Fairfield?

If you want to save the maximum during your visit to Fairfield, travel in November ($243 per night on average), February ($243), or October ($245), to find the lowest prices for the whole year.

In which months is it more expensive to rent a vacation rental in Fairfield?

Last year, the month that offered the highest average prices in Fairfield was August, with an average price of $581 per night. This was followed by July, with an average of $577, and then May, with $566.

Is Fairfield a good location for a last-minute getaway?

It's worthwhile if you can book your stay with plenty of time when visiting Fairfield, as only 21% of our accommodations are usually available throughout the year.

What are the best months for a last-minute getaway?

Last year, the months with the largest number of accommodations available of the year in Fairfield were February, July and January, with average availabilities of 43%, 40%, and 39%, respectively.

Are there many rentals in Fairfield?

We have 80 properties for you in Fairfield, provided by our 2 local and international partners.

Holidu compares hundreds of websites to find your perfect holiday rental for the best price. Vacation Rentals in Fairfield (CT) Vacation Rentals in Fairfield (CT)
Airbnb Vacation Rentals in Fairfield (CT)Airbnb Vacation Rentals in Fairfield (CT)
Vrbo Vacation Rentals in Fairfield (CT)Vrbo Vacation Rentals in Fairfield (CT)
Bookiply Vacation Rentals in Fairfield (CT)Bookiply Vacation Rentals in Fairfield (CT)
FeWo-direkt Vacation Rentals in Fairfield (CT)FeWo-direkt Vacation Rentals in Fairfield (CT)
Abritel Vacation Rentals in Fairfield (CT)Abritel Vacation Rentals in Fairfield (CT)
HRS Vacation Rentals in Fairfield (CT)HRS Vacation Rentals in Fairfield (CT)
500+ more
  1. Vacation Rentals
  2. USA
  3. New England
  4. Connecticut
  5. Fairfield (CT)