Fairfield, CT Vacation Rentals

Our Favorite Vacation Rentals in Fairfield

  • A New England Jewel with Scenic Beauty
     3br Home/Apartment
    HolidayLettings
    From
    $809
  • Westport "Gold Coast" across from Southport beach
     Cottage
    HolidayLettings
    From
    $271
  • Luxury Executive Estate 1 Hr from New York City
     6br Home/Apartment
    HolidayLettings
    From
    $1,431
  • COZY CAPE
     3br Home/Apartment
    HolidayLettings
    From
    $810
  • Country Home Away From Home
     4br Home/Apartment
    HolidayLettings
    From
    $584
  • Spectacular Modern Home Near NYC
     5br Home/Apartment
    HolidayLettings
    From
    $1,239
  • NEW-Stratford Home w/Porch, Walk to Housatonic Rvr
     4br Home/Apartment
    HolidayLettings
    From
    $296
  • Fairfield CT- Marsh Views-Walk Everywhere!
    Excellent3br Home/Apartment
    Airbnb
    From
    $396

Check prices for these upcoming dates

Fairfield Vacation Rentals with a Pool

  • Victorian apartment
    ExcellentHome/Apartment
    Airbnb
    From
    $167
  • Spring Paradise in Weston/Westport
    Good5br Home/Apartment
    Airbnb
    From
    $1,017
  • Trumford Guest House
    ExcellentHome/Apartment
    Airbnb
    From
    $220
  • Vibrant home in the heart of Norwalk !
     3br Home/Apartment
    Airbnb
    From
    $151

Fairfield Vacation Rentals with Wi-Fi

  • Spacious Cozy Private Apartment on a cul-de-sac
    GoodHome/Apartment
    Airbnb
    From
    $243
  • Luxurious Two Bedroom Suite
    Excellent2br Home/Apartment
    Airbnb
    From
    $149
  • Gem by the Sound
    ExcellentHome/Apartment
    Airbnb
    From
    $339
  • Historic Southport Village
    ExcellentCountry House
    Airbnb
    From
    $101

Fairfield Pet-Friendly Vacation Rentals

  • Westport CT In Town, Private Street, Sleeps 6
    Excellent3br Home/Apartment
    Airbnb
    From
    $607
  • Fairfield Home Away from Home - Close to Colleges
    Nice4br Home/Apartment
    Airbnb
    From
    $703
  • Great energy sweet beach cottage: Saugatuck Shores
    Excellent3br Home/Apartment
    Airbnb
    From
    $367
  • LAKE FRONT STUDIO
    ExcellentHome/Apartment
    Airbnb
    From
    $130

Fairfield, Connecticut Travel Guide

When it comes to quintessential New England towns, Fairfield, Connecticut holds a lot of appeal for visitors for many reasons. Given its prime location on the Long Island Sound, five miles of pristine shoreline and the picturesque Southport Harbor, this charming destination offers ample opportunity to spend time outdoors, whether making sandcastles on the beach, hiking, biking, and exploring the shops, sites, and quaint Colonial, Federalist and Victorian architecture found in the Historic District, which by the way happens to be listed on the National Register of Historic Places. Dining is also delightful with traditional taverns serving pub classics, seafood spots and fine dining establishments serving something to satisfy every craving.

Things to Do in Fairfield, Connecticut

A good place to enjoy the scenery and fresh air is the Lake Mohegan Recreation Area. Located off Morehouse Highway, the popular point of interest features tons of trails, quiet picnic areas as well as swimming during the warmer months. Nature lovers will also want to spend time at The Connecticut Audubon Society featuring the Larsen Sanctuary Trails and a beautiful backdrop to see all sorts of birds up close. Over at the Fairfield Museum and History Center, fascinating exhibitions such as 'Flappers: Fashion and Freedom' and 'Culper Ring: The Spies of George Washington' definitely keep it interesting. In the evening, on the campus of Fairfield University, culture abounds at the Fairfield Theatre Company which presents an outstanding program packed with stand-up comedians, well-known musicians, dance companies, films and more.

Best Time to Visit Fairfield, Connecticut

While Fairfield experiences all four seasons, summer is perhaps a favorite time to go with out-of-towners and locals flocking to Jennings Beach and Penfield Beach for the sun, surf and sand. Those who prefer to golf have the H. Smith Richardson Golf Course, which is open to the public for play. Finally, fall is perfect for watching the turning of the leaves, while winter is great for special holiday events.

Price and Availability in Fairfield

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The cheapest day to stay at a vacation rental in Fairfield tends to be Tuesday, while the most expensive day tends to be Saturday. Vacation homes in Fairfield tend to be busiest on Saturdays, while it tends to be much quieter on Tuesdays.
The most expensive month to stay in a vacation rental in Fairfield is in July, while the cheapest month is in February. The most popular time to book a vacation rental in Fairfield is in the high season in July. Fairfield has its low season in September, when less people are visiting and the vacation home occupancy rate drops.

The Weather in Fairfield

Rainy days
58°
4
56° 10°
3
63° 13°
3
70° 29°
6
83° 43°
5
91° 47°
3
99° 64°
8
90° 57°
3
84° 47°
1
87° 38°
6
71° 22°
1
56° 16°
7
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Nov
Dec
Rainy days

This climate histogram shows you the weather patterns in Fairfield. The warmest months in Fairfield are June and July, when temperatures reach 99 ˚F. The coolest month is December, when temperatures drop to 3 ˚F. The wettest month in Fairfield is June with 7.57 inches of rain, while the driest month is April with 0.93 inches of rain.

What Expert Travelers Think

  • — My favorite thing about AllTheRooms is that it combines both rentals and hotels available so you can see an entire view of what is available in a certain area. I was able to see listings on AllTheRooms that I never even saw on other travel sites!

    Daniella Flores
    Daniella FloresILIKETODABBLE
  • — I love AllTheRooms because it is not only local homes for renting, and not only hotels, but everything combined. When I am about to book a place to stay, I usually spend a couple of hours looking through both hotel sites and local home sites, comparing the prices and places.

    Alli Sims
    Alli SimsAlli Sims
  • — Whenever I am making travel plans I always use comparison sites to find the best accommodation for us at the best price. Whether it be for hotel stays or private rentals AllTheRooms makes this so much easier and quicker as it brings all my searches into one place, with a great offering of options

    Sarah Pool
    Sarah PoolTammymum

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