Fairfield County holiday homes

We found 1,490 holiday rentals — enter your dates for availability
Select from 396 houses, 251 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 Fairfield County destinations on Bookabach

Holiday rentals with weekly discounts – Fairfield County

Showing deals for:13 Nov - 20 Nov

Private kitchen
Living area
Dining
Balcony
Exceptional
(8 reviews)

Nature & Luxury @Lavender Lake Est (Kosher optional)

Roxbury

8% off
NZ$15,994
for 7 nights, 1 home
NZ$2,285 per night
includes taxes & fees
Nature & Luxury @Lavender Lake Est (Kosher optional)
Living room
View of back of house
Front of house
Stairs leading to third floor
Exceptional
(7 reviews)

Fairfield Beach Modern Colonial

Fairfield

8% off
NZ$14,817
for 7 nights, 1 home
NZ$2,117 per night
includes taxes & fees
Fairfield Beach Modern Colonial
Steam shower
Gorgeous sunsets every night
Private kitchen
Movie room with 85" 4k screen and surround sound Sonos System
Exceptional
(55 reviews)

Litchfield County Four Season Country Paradise

Roxbury

7% off
NZ$14,458
for 7 nights, 1 home
NZ$2,065 per night
includes taxes & fees
Litchfield County Four Season Country Paradise
Kitchen
Sunset
Living Room
Bedroom 1: King
Exceptional
(9 reviews)

6-Acre Luxurious Country Home with Goddess Point Lookout

Woodbury

8% off
NZ$21,630
for 7 nights, 1 home
NZ$3,090 per night
includes taxes & fees
6-Acre Luxurious Country Home with Goddess Point Lookout
Private kitchen
Interior
Interior
Interior
Exceptional
(20 reviews)

Beautiful, Fun Lakefront Retreat -- Perfect for family reunions / groups

Brookfield

17% off
NZ$21,409
for 7 nights, 1 home
NZ$3,058 per night
includes taxes & fees
Beautiful, Fun Lakefront Retreat -- Perfect for family reunions / groups
Pool
Terrace/patio
Dining
Interior
Exceptional
(5 reviews)

Lake house cozy to relax with a family. 6 bedroom very spacious house.

Trumbull

8% off
NZ$17,329
for 7 nights, 1 home
NZ$2,476 per night
includes taxes & fees
Lake house cozy to relax with a family. 6 bedroom very spacious house.
Pool
Living area
Room
Living area
Exceptional
(5 reviews)

2 Beautiful Homes, 1 Stunning Retreat: Pool HotTub Pizza Oven + Near Beach & NYC

Fairfield

8% off
NZ$31,484
for 7 nights, 1 home
NZ$4,498 per night
includes taxes & fees
2 Beautiful Homes, 1 Stunning Retreat: Pool HotTub Pizza Oven + Near Beach & NYC
Property grounds
Living area
Private kitchen
Living area
Exceptional
(9 reviews)

Renovated Milford Beach home by Charles Island/Silver Sands Pk

Milford

8% off
NZ$4,885
for 7 nights, 1 cottage
NZ$698 per night
includes taxes & fees
Renovated Milford Beach home by Charles Island/Silver Sands Pk
Large comfortable sectional with a 70" smart tv
Enjoy lounging after a long beach day on the sectional looking out at the water
Fully stocked kitchen with stainless steel appliances and breakfast counter
Exterior
Exceptional
(10 reviews)

Luxury Beach Oasis with Amazing Panoramic Ocean Views

Milford

8% off
NZ$10,141
for 7 nights, 1 home
NZ$1,449 per night
includes taxes & fees
Luxury Beach Oasis with Amazing Panoramic Ocean Views
Property grounds
Outdoor dining
Dining
Exterior
Exceptional
(5 reviews)

On the Water Spacious Comfortable Historic Home

West Haven

8% off
NZ$11,832
for 7 nights, 1 home
NZ$1,690 per night
includes taxes & fees
On the Water Spacious Comfortable Historic Home
Bar (on property)
Golf
Property grounds
Bar (on property)
Exceptional
(71 reviews)

Northport quaint restored Boathouse with sunset views!

Northport

8% off
NZ$5,163
for 7 nights, 1 cottage
NZ$738 per night
includes taxes & fees
Northport quaint restored Boathouse with sunset views!
Property grounds
Outdoor dining
Interior
Living area
Exceptional
(20 reviews)

Beautiful lake view home on Whaley Lake in Holmes, NY.

Holmes

8% off
NZ$8,299
for 7 nights, 1 home
NZ$1,186 per night
includes taxes & fees
Beautiful lake view home on Whaley Lake in Holmes, NY.
Property grounds
Interior
Private kitchen
Property grounds
Exceptional
(30 reviews)

Candlewood Lake - Family Getaway with direct lake access. 3775 sqft home.

Danbury

8% off
NZ$13,689
for 7 nights, 1 home
NZ$1,956 per night
includes taxes & fees
Candlewood Lake - Family Getaway with direct lake access. 3775 sqft home.
Living area
Outdoor dining
Living area
Kitchen
Exceptional
(6 reviews)

Silver Sands Beach Getaway

Milford

16% off
NZ$5,378
for 7 nights, 1 home
NZ$768 per night
includes taxes & fees
Silver Sands Beach Getaway
main floor, king bed with bathroom, fireplace, slider opens to deck and hot tub.
Flat yard,
Living area
double fridge for extea space
Exceptional
(85 reviews)

Entertainers Dream, Candlewood Lake, Hot Tub,Disco,Theatre,Music studio..more!

New Fairfield

8% off
NZ$21,247
for 7 nights, 1 home
NZ$3,035 per night
includes taxes & fees
Entertainers Dream, Candlewood Lake, Hot Tub,Disco,Theatre,Music studio..more!
Stone fireplace is the centerpiece of the home and a great place to take photos
Property grounds
Lovely outdoor area and screened in porch to enjoy nature (without the bugs!)
Guests love spending quality time together in the living room
Exceptional
(84 reviews)

Historic Warren/Kent Home

Cornwall Bridge

7% off
NZ$4,521
for 7 nights, 1 home
NZ$646 per night
includes taxes & fees
Historic Warren/Kent Home
Private kitchen
Children’s area
Outdoor dining
Interior
Exceptional
(49 reviews)

Quaint duplex with private yard. Walk to beach, dining, & shopping!

Greenwich

7% off
NZ$3,959
for 7 nights, 1 home
NZ$566 per night
includes taxes & fees
Quaint duplex with private yard. Walk to beach, dining, & shopping!
Interior
Private kitchen
Exterior
Room
Exceptional
(6 reviews)

Darien family home on a Cul de Sac with pond.

Darien

8% off
NZ$10,854
for 7 nights, 1 home
NZ$1,551 per night
includes taxes & fees
Darien family home on a Cul de Sac with pond.
Private kitchen
Property grounds
Property grounds
Interior
Exceptional
(7 reviews)

A Peaceful Bucolic Retreat by the Water at the Gateway of Hudson Valley

Holmes

8% off
NZ$4,906
for 7 nights, 1 home
NZ$701 per night
includes taxes & fees
A Peaceful Bucolic Retreat by the Water at the Gateway of Hudson Valley
Comfortable Living Room with 42" Smart TV.
Well stocked newly renovated kitchen. Prepare quick breakfast or a holiday meal.
Bedroom 1 (largest).Queen Bed, Smart TV, Dresser Desk with Ergonomic Chair.
Dining room seats 6 and expands for 8 with leaf.
Exceptional
(14 reviews)

Quiet suburban home close to Fairfield beaches and universities

Fairfield

8% off
NZ$3,686
for 7 nights, 1 home
NZ$527 per night
includes taxes & fees
Quiet suburban home close to Fairfield beaches and universities
Enjoy the view of the lake from the kitchen/ living room.
Autumn at the cottage, leaves from our favorite tree a Red Maple.
Spiral staircase leading to the mezzanine where the bedroom is located.
The pool and the lounge area available from May- September.
Exceptional
(16 reviews)

The Cottage by the Lake: Hudson Valley Indulgence/1 hr. from NYC/welcome pets!.

Brewster

25% off
NZ$2,905
for 7 nights, 1 room
NZ$415 per night
includes taxes & fees
The Cottage by the Lake: Hudson Valley Indulgence/1 hr. from NYC/welcome pets!.
Exterior
Marina
Living area
Outdoor dining
Exceptional
(14 reviews)

<br>❤️High-Line Harbor Flat 2 BD | Train🚊 | Harbor Point Access | 40 Minutes to NYC🗽

Stamford

7% off
NZ$2,229
for 7 nights, 1 apartment
NZ$318 per night
includes taxes & fees
<br>❤️High-Line Harbor Flat 2 BD | Train🚊 | Harbor Point Access | 40 Minutes to NYC🗽
Living area
Your view everyday!
Living area
Interior
Exceptional
(45 reviews)

#2 Beautiful Milford Beach Right Across Street - Charles Island/Silver Sands Pk

Milford

8% off
NZ$4,017
for 7 nights, 1 apartment
NZ$574 per night
includes taxes & fees
#2 Beautiful Milford Beach Right Across Street - Charles Island/Silver Sands Pk
Living Room
Stairwell to Master
Queen Bedroom 2
Kitchen
Excellent
(6 reviews)

Beach Apartment in Woodmont Milford

Milford

8% off
NZ$3,761
for 7 nights, 1 apartment
NZ$537 per night
includes taxes & fees
Beach Apartment in Woodmont Milford

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:

  • Norwalk Maritime Aquarium (10.4 mi / 16.7 km)
  • Country Club of Fairfield (10.5 mi / 17 km)
  • Beardsley Zoo (11.4 mi / 18.4 km)
  • Chelsea Piers (14.9 mi / 23.9 km)
  • Thunder Ridge Ski Resort (20.3 mi / 32.7 km)
  • Putnam County Golf Course (21.1 mi / 34 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:

  • Weir Farm National Historic Site (3.2 mi / 5.1 km)
  • Compo Beach (10.3 mi / 16.5 km)
  • Jennings Beach (11.1 mi / 17.9 km)
  • Calf Pasture Beach (11.2 mi / 18 km)
  • Penfield Beach (11.3 mi / 18.2 km)
  • Fairfield Beach (11.3 mi / 18.3 km)

How to get to and around Fairfield County

The nearest airport is in Danbury, CT (DXR-Danbury Municipal), located 9.8 mi (15.7 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 mi (24.2 km) away.

If you prefer to travel by train, Westport Station, Southport Station and Green's Farms Station are the main stations in the city.

Frequently asked questions

What is the best area to stay in Fairfield County when booking a holiday home?
One of the more in-demand destinations to book your holiday home in Fairfield County is Westport. Stay here and visit its big-ticket attractions, like Compo Beach and Westport Country Playhouse.
What is the most popular type of holiday home accommodation in Fairfield County?
According to our data, houses are considered the most popular type of holiday property in Fairfield County. But as you know, everyone's idea of an awesome trip isn't going to be the same. Bookabach has holiday homes of all sizes, shapes and budgets, so you're sure to discover the best fit for your needs.
How much does it cost to rent a holiday home in Fairfield County?
The average price for a holiday home in Fairfield County depends on several factors, such as season, property type and length of stay. Whether you're in search of a sprawling house with room for friends and family or a quaint cabin just for the two of you, just enter your dates of travel to see stays with terrific value.
How much does it cost to rent a beach house in Fairfield County?
Prices for beach houses in Fairfield County may vary depending on the size and style of the property and when you plan to travel. Simply enter your travel dates into Bookabach and the number of guests to view holiday home options and prices. From there you can use the filters to tailor your search by ratings, amenities and more.
What are popular home amenities in Fairfield County?
When it comes to home amenities that guests are on the lookout for in Fairfield County, a washing machine, a dryer and a microwave oven are at the top of the list. With Bookabach holiday homes, you'll enjoy options to match your style and taste, whether you're planning to get away with relatives, friends or even pets.
Are there large group holiday homes in Fairfield County?
Fairfield County has 76 holiday homes that can accommodate 10 or more guests. These stays come with the space and privacy you need to enjoy good times with your favourite people.
What are the top attractions for families in Fairfield County?
There's a ton of wonderful things to see and do with the family in Fairfield County, such as:
  • Chelsea Piers
  • Norwalk Maritime Aquarium
  • Hartford HealthCare Amphitheatre
Can I find two-bedroom holiday homes in Fairfield County?
You can pick from 71 two-bedroom homes in Fairfield County. Put the kids in the second room or maybe fill it with a couple of your best friends. There's a comfy spot for whoever's fortunate enough to be joining your adventure.
Are there holiday homes with WiFi in Fairfield County?
Fairfield County has 185 holiday homes with WiFi, so you can stay connected during your holiday. Simply check the "WiFi" box in our handy search filter for a list of properties with this feature. From streaming movie blockbusters to catching up on social media, these Bookabach homes will keep you online.
How old do you have to be to rent a holiday home in Fairfield County?
We recommend checking with the Fairfield County holiday property you're considering on Bookabach as the minimum age varies. However, it's normally 16, 18 or 21.
How long can I rent a holiday home in Fairfield County for?
How long you can rent a holiday home in Fairfield County varies according to the property. Just enter your desired travel dates to see a list of options offering extended stays. With tons of amenities like air conditioning and laundries, as well as some offering weekly or monthly discounts, you're sure to get the perfect place to call your home away from home in Fairfield County.

More holiday ideas