Fairfield County holiday rentals

We found 1,488 holiday rentals — enter your dates for availability
Select from 392 houses, 241 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 Stayz

Holiday rentals with weekly discounts – Fairfield County

Showing deals for:25 Dec - 1 Jan

Foyer
Sunset
Kitchen
Bedroom 1: King
Exceptional
(9 reviews)

6-Acre Luxurious Country Home with Goddess Point Lookout

Woodbury

5% off
AU$18,877
for 7 nights, 1 home
AU$2,697 per night
includes taxes & fees
6-Acre Luxurious Country Home with Goddess Point Lookout
18' x 36' heated pool.
Gorgeous sunsets every night
Steam shower
Private kitchen
Exceptional
(56 reviews)

Litchfield County Four Season Country Paradise

Roxbury

8% off
AU$13,328
for 7 nights, 1 home
AU$1,904 per night
includes taxes & fees
Litchfield County Four Season Country Paradise
Stairs leading to third floor
View of back of house
Front of house
Kitchen
Exceptional
(7 reviews)

Fairfield Beach Modern Colonial

Fairfield

8% off
AU$12,432
for 7 nights, 1 home
AU$1,776 per night
includes taxes & fees
Fairfield Beach Modern Colonial
Family room by night with garage doors retracted.
Outdoor dining
Well stocked eat-in kitchen with stainless appliances.
Private kitchen
Exceptional
(122 reviews)

Direct Waterfront Home~Panoramic Views & Hot Tub on Candlewood Lake~Weekly Disct

Danbury

8% off
AU$5,920
for 7 nights, 1 home
AU$846 per night
includes taxes & fees
Direct Waterfront Home~Panoramic Views & Hot Tub on Candlewood Lake~Weekly Disct
Property grounds
Terrace/patio
Dining
Interior
Exceptional
(5 reviews)

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

Trumbull

8% off
AU$14,532
for 7 nights, 1 home
AU$2,076 per night
includes taxes & fees
Lake house cozy to relax with a family. 6 bedroom very spacious house.
Open layout living
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
Large comfortable sectional with a 70" smart tv
Exceptional
(10 reviews)

Luxury Beach Oasis with Amazing Panoramic Ocean Views

Milford

8% off
AU$10,631
for 7 nights, 1 home
AU$1,519 per night
includes taxes & fees
Luxury Beach Oasis with Amazing Panoramic Ocean Views
Pool
Living area
Terrace/patio
Room
Exceptional
(5 reviews)

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

Fairfield

8% off
AU$30,411
for 7 nights, 1 home
AU$4,344 per night
includes taxes & fees
2 Beautiful Homes, 1 Stunning Retreat: Pool HotTub Pizza Oven + Near Beach & NYC
Living area
Living area
Interior
Private kitchen
Exceptional
(11 reviews)

Renovated Milford Beach home by Charles Island/Silver Sands Pk

Milford

8% off
AU$4,075
for 7 nights, 1 cottage
AU$582 per night
includes taxes & fees
Renovated Milford Beach home by Charles Island/Silver Sands Pk
double fridge for extea space
Flat yard,
Living area
View from property
Exceptional
(87 reviews)

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

New Fairfield

8% off
AU$19,022
for 7 nights, 1 home
AU$2,717 per night
includes taxes & fees
Entertainers Dream, Candlewood Lake, Hot Tub,Disco,Theatre,Music studio..more!
Front of Cottage 2024
small, covered front porch on cottage
Interior
New refrigerator, microwave, air fryer, coffee maker 2022
Exceptional
(9 reviews)

Clean & Bright 2 Bedroom Cottage shares 8 Acres

Southbury

16% off
AU$3,640
for 7 nights, 1 cottage
AU$520 per night
includes taxes & fees
Clean & Bright 2 Bedroom Cottage shares 8 Acres
Room
Outdoor dining
Living area
Property grounds
Exceptional
(21 reviews)

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

Holmes

8% off
AU$6,877
for 7 nights, 1 home
AU$982 per night
includes taxes & fees
Beautiful lake view home on Whaley Lake in Holmes, NY.
Living area
Outdoor dining
Bedroom 2
Living area
Exceptional
(8 reviews)

Silver Sands Beach Getaway

Milford

16% off
AU$4,488
for 7 nights, 1 home
AU$641 per night
includes taxes & fees
Silver Sands Beach Getaway
Room
Private kitchen
Interior
Dining
Exceptional
(6 reviews)

Darien family home on a Cul de Sac with pond.

Darien

8% off
AU$8,955
for 7 nights, 1 home
AU$1,279 per night
includes taxes & fees
Darien family home on a Cul de Sac with pond.
Exterior
Family room
Primary BR
Interior
Exceptional
(22 reviews)

Beautiful Escape! Hudson Valley House. 90min from NYC & 30min from Beacon.

Carmel

12% off
AU$6,979
for 7 nights, 1 home
AU$997 per night
includes taxes & fees
Beautiful Escape! Hudson Valley House. 90min from NYC & 30min from Beacon.
Children’s area
Children’s area
Outdoor dining
Private kitchen
Exceptional
(25 reviews)

Stylish downstairs apt. Walk to town, train, & beach ferry! Off-street parking.

Greenwich

8% off
AU$4,588
for 7 nights, 1 home
AU$655 per night
includes taxes & fees
Stylish downstairs apt. Walk to town, train, & beach ferry! Off-street parking.
Private kitchen
Property grounds
Dining
Property grounds
Exceptional
(7 reviews)

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

Holmes

8% off
AU$4,014
for 7 nights, 1 home
AU$573 per night
includes taxes & fees
A Peaceful Bucolic Retreat by the Water at the Gateway of Hudson Valley
Interior
Marina
Living area
Exterior
Wonderful
(16 reviews)

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

Stamford

7% off
AU$2,134
for 7 nights, 1 apartment
AU$305 per night
includes taxes & fees
<br>❤️High-Line Harbor Flat 2 BD | Train🚊 | Harbor Point Access | 40 Minutes to NYC🗽
Living Room
Stairwell to Master
Dining Room
Queen Bedroom 2
Excellent
(6 reviews)

Beach Apartment in Woodmont Milford

Milford

8% off
AU$3,551
for 7 nights, 1 apartment
AU$507 per night
includes taxes & fees
Beach Apartment in Woodmont Milford
Bathroom
View of the Pond
Kitchen
Living Room
Exceptional
(7 reviews)

Private Apartment in Southbury 101

Southbury

8% off
AU$2,336
for 7 nights, 1 apartment
AU$334 per night
includes taxes & fees
Private Apartment in Southbury 101
Living area
Private kitchen
Private kitchen
Interior
Exceptional
(17 reviews)

Downtown One Bedroom Suite Steps to Metro North

Harrison

16% off
AU$2,670
for 7 nights, 1 apartment
AU$381 per night
includes taxes & fees
Downtown One Bedroom Suite Steps to Metro North
Interior
Living area
Interior
Room
Exceptional
(37 reviews)

1 bedroom Cozy, comfy, super clean, great location and own entrance!!

Shelton

7% off
AU$810
for 7 nights, 1 apartment
AU$116 per night
includes taxes & fees
1 bedroom Cozy, comfy, super clean, great location and own entrance!!
Dining
Living area
Room
Private kitchen
Very good
(13 reviews)

❤️High-Line Harbor Pad 2 BDTrain🚊Harbor Point Access 40 Minutes to NYC

Stamford

7% off
AU$2,262
for 7 nights, 1 apartment
AU$323 per night
includes taxes & fees
❤️High-Line Harbor Pad 2 BDTrain🚊Harbor Point Access 40 Minutes to NYC
Interior
Interior
Private kitchen
Interior
Exceptional
(10 reviews)

The Season’s Luxe One Bedroom Apartment, Center of Stamford, Train2NYC

Stamford

5% off
AU$1,440
for 7 nights, 1 apartment
AU$206 per night
includes taxes & fees
The Season’s Luxe One Bedroom Apartment, Center of Stamford, Train2NYC
Outdoors
Open Concept Living Room, Dining Room, Kitchen
Dining Room
Queen Bedroom
Wonderful
(6 reviews)

Private Apartment in Southbury 102

Southbury

8% off
AU$2,126
for 7 nights, 1 apartment
AU$304 per night
includes taxes & fees
Private Apartment in Southbury 102

Why visit Fairfield County

  • Scenic Coastal Beauty: Enjoy sandy beaches along the Long Island Sound, perfect for relaxation and seaside activities.
  • Cultural Experiences: Immerse yourself in local arts and history through charming towns and historical landmarks.
  • Outdoor Activities: Discover urban parks and serene nature preserves ideal for hiking, picnicking, and family outings.
  • Vibrant Neighbourhoods: Explore unique neighbourhoods that offer a mix of contemporary living and local culture.
  • Family-Friendly Atmosphere: Experience a welcoming environment with plenty of attractions for both families and couples.

Popular types of accommodation in Fairfield County

Discover Fairfield County, Connecticut, where holiday rentals offer the perfect base for exploring local attractions such as historic sites, scenic coastlines, and charming villages. Enjoy a choice of private holiday homes, apartments, or cottages. Whether you’re seeking rent Fairfield County, home or Fairfield County rentals, you’ll find Fairfield County homes that perfectly match your travel needs. Experience the best of local culture and leisure in this delightful province_state.

  • Private Holiday Homes: The top choice for visitors seeking a comfortable and spacious environment during their stay in Fairfield County.
  • Apartments: A popular option offering convenience and flexibility, perfect for those looking for a home-like atmosphere.
  • Cottages: Charming and quaint, these provide a cosy retreat amidst the beautiful surroundings of the area.
  • Condos: Ideal for those who desire modern amenities and communal facilities while enjoying their holiday.
  • Villas: Luxurious spaces that offer a lavish experience, perfect for families or groups wanting extra comfort.**

Top attractions in Fairfield County

Discover the charm of Fairfield County, Connecticut, where outdoor adventures meet captivating cultural experiences. Enjoy leisurely strolls along sandy beaches, explore urban parks and serene preserves, and immerse yourself in the scenic beauty perfect for family outings or romantic escapes. Whether you fancy a relaxing day by the sea or a vibrant city park stroll, Fairfield County offers a delightful blend of nature and culture for every traveller.

  • The Glass House: A stunning architectural masterpiece designed by Philip Johnson, this museum showcases modern design amidst beautiful landscapes, offering a unique blend of art and nature.
  • Bridgeport Downtown South Historic District: This charming area is rich in history, featuring well-preserved buildings and cultural landmarks, perfect for a leisurely stroll while soaking in the local heritage.
  • Fairfield Beach: A picturesque sandy beach ideal for relaxation, swimming, and sunbathing, providing a refreshing coastal experience with scenic views of Long Island Sound.

Things to do recommended for couples

Escape to Fairfield County for a romantic retreat. Enjoy cosy walks along scenic parks and charming town centres, followed by a delightful dinner in a local bistro, creating unforgettable memories for you both.

Things to do recommended for families

Families visiting Fairfield County can have a delightful time at the Maritime Aquarium in Norwalk, where kids can explore marine life, and enjoy a fun-filled day at Beardsley Zoo in Bridgeport, featuring various animal exhibits and interactive activities perfect for young adventurers.

Things to do recommended for groups

Experience thrill and adventure at The Adventure Park at Discovery Museum in Fairfield County, Connecticut, with exhilarating zipline and ropes course activities, perfect for group travellers seeking an outdoor escapade.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

What do I need to keep in mind when booking a vacation in Fairfield County

If you’re travelling with a group, family, or pets, or if you’re seeking longer stays, be sure to apply the appropriate filters to suit your needs. Here are some helpful booking tips from Stayz.

  • Traveling to Fairfield County with a group: Consider how many bedrooms you'll require, along with amenities like a fully equipped kitchen or an outdoor area for group gatherings. Fortunately, you can apply filters for all these features, and many more, on Stayz.
  • Traveling to Fairfield County with young kids: Traveling with young children can present its challenges. It is important to prioritise their comfort and safety, ensuring they have access to appropriate facilities, such as a private swimming pool. Additionally, it is advisable to consider the location's proximity to attractions that are suitable for families.
  • Taking your pets with you to Fairfield County: For many, a family holiday is not complete without their four-legged companion. If this resonates with you, consider exploring Stayz properties that welcome pets. Most pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone feels right at home.
  • Planning for a long term stay visiting Fairfield County: If you’re in search of holiday rentals offering discounts for stays of a month or more, you’ve come to the right place. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to include preferences such as a parking space, a well-equipped kitchen, or even a private pool in your search.

Where to stay in Fairfield County

Fairfield County, Connecticut, offers a delightful blend of outdoor adventures and romantic scenery, perfect for a holiday getaway. Explore its charming towns, where family-friendly atmospheres meet historical landmarks. Experience contemporary living in vibrant neighbourhoods, each with its unique character. From scenic parks to picturesque waterfronts, Fairfield County is an ideal destination for those seeking both relaxation and exploration amidst friendly locals and stunning landscapes.

  • Stamford: Nestled in the heart of Fairfield County, Stamford offers a vibrant city-themed escape ideal for families and those seeking outdoor adventures. Visitors can enjoy an array of shopping precincts and cultural activities such as theatre performances and educational venues. The local attractions include a bustling tourist precinct and modern squares, setting the scene for a dynamic urban experience. The city’s geographical location allows travellers to explore both the lively urban centres and nearby outdoor spaces, ensuring a balanced blend of city life and nature.
  • Norwalk: Located within Fairfield County, Norwalk presents a wonderful family-friendly destination with a mix of city-themed and outdoor experiences. Explore engaging educational venues and a well-appointed shopping area, as well as a scenic golf course for leisure activities. The nearby beach and modern college university add to the town’s charm, while the family beach provides a relaxed coastal retreat. Norwalk’s geographical setting offers a seamless connection between urban exploration and tranquil seaside escapes.
  • Fairfield: Fairfield is a city that perfectly marries cultural, city-themed, and outdoor experiences. Situated in the picturesque Fairfield County, it offers enriching educational venues, a challenging golf course, and diverse recreational areas. The local attractions, including a modern college university and family beach, enhance the city’s appeal. Fairfield’s location makes it an ideal destination for travellers seeking to immerse themselves in both cultural and outdoor pursuits, with every corner offering a unique blend of historical charm and modern vibrancy.

Booking with Stayz is a breeze

Looking to cut costs on your upcoming break? Consider being flexible with your travel dates, as prices can differ, and a longer stay often translates to additional savings. To discover the ideal Stayz property that suits your budget, utilise our filters to search by price, location, and type of holiday rental.

Stayz Trips: Planning made easy

Stayz’s cutting-edge Trip Board offers you a dedicated space to craft new journeys, pick up where you previously paused, or review and organise your plans. Properties that you have saved or booked in the past can now be found under Potential, Upcoming, or Current Trips. To access Trip Boards, please visit: https://www.stayz.com.au/trips

**Based on Vrbo properties bookings.

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)
  • 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)
  • Quassy Amusement Park (23.1 mi / 37.1 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:

  • Tarrywile Park and Mansion (9.5 mi / 15.3 km)
  • Compo Beach (10.3 mi / 16.5 km)
  • Jennings Beach (11.1 mi / 17.9 km)
  • Penfield Beach (11.3 mi / 18.2 km)
  • Fairfield Beach (11.3 mi / 18.3 km)
  • Seaside Beach (11.9 mi / 19.1 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. Stayz 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 Stayz 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 Stayz 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 Stayz 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 Stayz 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.

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