Fairfield County holiday lettings

We found 1,146 holiday rentals — enter your dates for availability

your current months are September, 2023 and October, 2023.
September 2023
October 2023
Select from 333 houses, 104 apartments and other holiday rentals to find the perfect place for your stay in Fairfield County. Holiday rentals offer the amenities that you expect for you and your friends, family or even pets, such as Wi-Fi and a pool. You'll be sure to find a property to rent that has what everyone needs, including places that are non-smoking or accessible.

Popular cities in Fairfield County

Find spaces that suit your style

  • Peace of mind
    Our Book with Confidence Guarantee gives you 24/7 support
  • More quality time
    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home
    Enjoy full kitchens, pools, gardens and more
  • More for less
    More space, more privacy, more amenities — more value

Choose a holiday rental for your Fairfield County getaway

Learn about the unique charm of Fairfield County with a stay in a holiday home rental. This city has something for everyone. With a holiday rental, you get a home away from home – many rentals offer full kitchens and outdoor grills for some home cooking.

Sightseeing in and around Fairfield County

Do you want to find top things to see and do while you're in town? Venture out of your holiday home and experience everything that makes Fairfield County a fun place to get away to. Here are some of the major attractions to see, all within 30 miles (48.2 km) of the city centre:

  • Beardsley Zoo (12 mi / 19.3 km)
  • Country Club of Fairfield (12.3 mi / 19.9 km)
  • Norwalk Maritime Aquarium (12.7 mi / 20.4 km)
  • Chelsea Piers (17.1 mi / 27.5 km)
  • Thunder Ridge Ski Resort (18.4 mi / 29.6 km)
  • Putnam County Golf Course (20.4 mi / 32.8 km)

Exploring the natural landscape of Fairfield County

Whether you're an outdoor enthusiast or just want to appreciate the scenery, Fairfield County is a great place to spend some time outside. Here are a few of the area's most eye-catching sights, all within 30 miles (48.2 km) of the city centre:

  • Compo Beach (12.5 mi / 20.1 km)
  • Jennings Beach (12.6 mi / 20.3 km)
  • Penfield Beach (12.9 mi / 20.8 km)
  • Seaside Beach (13 mi / 21 km)
  • Fairfield Beach (13.1 mi / 21 km)
  • Seaside Park (13.1 mi / 21.1 km)

How to get to and around Fairfield County

The nearest airport is in Danbury, CT (DXR-Danbury Municipal), located 7.9 mi (12.8 km) from the city centre. If you're unable to find a flight that fits your schedule, you might consider flying into Bridgeport, CT (BDR-Igor I. Sikorsky Memorial), which is 15.9 mi (25.6 km) away.

If you prefer to travel by train, Westport Station, Southport Station and Fairfield Metro Station are the main stations in the city.

Frequently asked questions

What are the top holiday rentals in Fairfield County?

Whether you're planning an adventurous break with friends or a romantic rendezvous with your special someone, one of these top holiday rentals in Fairfield County is sure to catch your eye:

  • "Cosy Cottage With Wi Fi Close To Stratford On Avon And The Cotswolds": This Cos Cob rental offers 3 bedrooms and is rated highly among guests. Amenities such as a dishwasher and a toaster help make your stay an enjoyable one.
  • "A Secluded Modern Getaway": Put your bags down and your feet up at this favourite in Fairfield County. It features 5 bedrooms, WiFi, a TV and more.

For even more great options, use the search bar at the top of the page to find the perfect Fairfield County holiday rental for you.

Can I find log cabins to rent in Fairfield County?

Sometimes, you just want to get away from the chaos of everyday life. That's where Vrbo can help. We've got a great range of log cabin rentals in and around Fairfield County where you can relax in nature. Try these on for size:

  • "Cosy Log Cabin On Sleeping Giant" will help ensure your Fairfield County holiday is just what you wanted it to be. With conveniences such as a fireplace and a firepit to make life easy, all you have to do is put your feet up and enjoy yourself.
  • Invite a few friends along or snuggle up with your partner at "Cosy Log Cabin Retreat With Pool On 4 Acres". An oven and a kitchen are just some of the amenities included at this tempting option.

What are the top-rated holiday rentals for weekend getaways in Fairfield County?

While extended holidays to new places are incredible, there's something lovely about slipping off for a weekend getaway. These properties in Fairfield County are perfect for just that:

  • "Private Family Friendly Home With In" - This retreat in Fairfield County features amenities that'll make your visit nice and comfortable, such as a washing machine and off-street parking options. Its terrific location also makes it a great base to do some exploring.
  • "Bedroom, Beautiful Bathroom And Second Room With Work Or Eating Area" - This is another top choice with all the ingredients that make for a fab weekend away. Expect towels and off-street parking options at this New England rental.

Can I find studio apartments for rent in Fairfield County?

Ditch the boring hotel room and secure one of our studio apartments in Fairfield County. Here's where you can hunker down in your own digs and experience your next holiday destination like a local:

  • Get comfy at "Bedroom, Beautiful Bathroom And Second Room With Work Or Eating Area", situated in New England. There are plenty of amenities you can take advantage of here, including a washing machine and high-speed internet services.
  • Filled with character and with more privacy than a bustling hotel, "Beautiful Apartment In Rural Redding Surrounded By New Enland Foliage" is another great pick. It's located in Ramsau am Dachstein and comes with a fridge and heating.

Can I find short term rentals in Fairfield County?

With Vrbo's fantastic range of short-term rentals in Fairfield County, you're sure to find a property to suit your needs. Whether you're after somewhere to wind down on your own or to catch up with friends and family, these options are difficult to beat:

  • Located close to central Fairfield County, "Private Family Friendly Home With In" is an ideal place for a short-term stay. Set up base here and head out to explore all the interesting attractions around the area.
  • Otherwise, spend a day or two at "Bedroom, Beautiful Bathroom And Second Room With Work Or Eating Area" and discover the attractions of New England. This property also welcomes short-stay guests and is a great choice if you like to be close to the action.

What are the best romantic weekend getaways in Fairfield County?

Whether you've been paired up for a few months, a decade or an eternity, there's nothing like a romantic weekend getaway to keep passions alive. If you're searching for somewhere idyllic to spend a couple of days with your significant other, you'll fall headfirst for these retreats:

  • Unleash your inner Casanova at "Cosy Cottage With Wi Fi Close To Stratford On Avon And The Cotswolds". This Cos Cob retreat is perfect for romance, offering amenities like beauty services and a nearby marina to help set the mood.
  • Alternatively, organise a loved-up weekend escape at "A Secluded Modern Getaway". Located in Fairfield County, it offers a fireplace, a swimming pool and other highlights.

What's the best place to stay if you're looking to rent a house for a weekend in Fairfield County?

There's no better way to spend a weekend than by the sea. If you're up for a couple of relaxing days near the water, we've got some terrific houses for rent at Seaside Beach. This delightful strip is located in Bridgeport and is perfect for a quick fix of fun under the sun.

What are the best large group holiday rentals in Fairfield County?

If you're planning that special trip away, don't travel alone; bring the whole gang along. You'll have more fun sharing the adventure with the people you love. These holiday rentals in Fairfield County are perfect for larger groups:

  • "Celebrate Rosh Hashanah And The Holidays W": With 6 bedrooms, everyone is invited to this impressive retreat in Fairfield. A swimming pool and a kitchen are among the many amenities offered here.
  • "Huge Executive Home In Charming Rural Town 1hr Nyc": You'll get your crew's stamp of approval at this option in Easton which comes with a garden, off-street parking options and more. It has 7 bedrooms that will comfortably accommodate any large group.

What are the best houses for rent with a pool in Fairfield County?

In Fairfield County, there's no shortage of house rentals where a pool day can be every day. Having a splashing good time will be your main priority at one of these sought-after properties:

  • The pool at "Holiday Ready: Beautiful House With Heated Pool" is guaranteed to add another layer of fun to your adventure. Located in Westport, this rental home also comes with a fridge and a barbecue grill.
  • Hop out of bed and enjoy a refreshing morning dip at "3 - Level Retro House/close To Beach" in Norwalk. A kitchen and coffee and tea making facilities are other amenities at this exceptional option.

What are the best large family holiday rentals in Fairfield County?

The first step to any memorable family getaway is finding the perfect place to stay. If you want a home away from home with enough space for everyone, one of these large family holiday rentals in Fairfield County will be just the ticket:

  • For family-friendly properties in Fairfield County, "A Secluded Modern Getaway" is a fabulous choice. It features 5 bedrooms and can sleep up to 10 lucky guests. A microwave oven and a smart TV are two of the useful amenities you'll find here.
  • "Private Family Friendly Home With In" in Fairfield County is another appealing option. It caters for up to 8 guests over 4 bedrooms. Coffee and tea making facilities and a DVD player will help keep your crew happy and comfortable.

Bust out of the house and head to Norwalk Maritime Aquarium — one of Fairfield County's finest family-friendly attractions. Greenwich Avenue and Beardsley Zoo are also worth checking out while you're in the area.

Can I find family cabin rentals in Fairfield County?

Renting a cabin in Fairfield County is an ideal excuse to reconnect with your nearest and dearest. Consider these popular options:

  • "Secluded Cabin For The Perfect Weekend Escape" - Located in Lakeville, this cosy escape features useful amenities such as childrens activities and coffee and tea making facilities.
  • "Luxe Lakefront Cottage With King Size Bed And Beach" - Make fond memories with the kids at this popular cabin. Located in Coventry Lake, it features a DVD player, a microwave oven and more.

For more options, use the search bar at the top of the page and adjust the filters to find the Fairfield County holiday rental that's perfect for your needs.

What are the best large houses to rent with indoor pools in Fairfield County?

Relaxation bliss for adults and a source of entertainment for kids, an indoor pool will add extra pizazz to your escape. If you're seeking someplace spacious where everyone can enjoy a swim, check out these gorgeous large houses in Fairfield County:

  • Come in, the water's fine at "Greenwich Back Country Farm House". Located in Greenwich, this exceptional holiday rental has 5 bedrooms sleeping up to 10 guests. A swimming pool and a kitchen are other amenities that help make this place a top pick.
  • Alternatively, stay a week or more at "Apartment Al Pescatore In Mal" in Bozzana. When you're not splashing around in the water, take advantage of a nearby waterfront and a garden. This property has 5 bedrooms accommodating up to 10 people.

Eager to see some more options? Check out the search bar at the top of the page, adjust the filters to find the Fairfield County holiday rental that's perfect for your needs and lock in your dream escape today.

More Holiday Rentals ideas

People also search for