Fairfield County holiday rentals

We found 1,491 holiday rentals — enter your dates for availability
Select from 392 houses, 243 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:13 Nov - 20 Nov

Balcony
Living area
Interior
Dining
Exceptional
(8 reviews)

Nature & Luxury @Lavender Lake Est (Kosher optional)

Roxbury

8% off
AU$13,369
for 7 nights, 1 home
AU$1,910 per night
includes taxes & fees
Nature & Luxury @Lavender Lake Est (Kosher optional)
Stairs leading to third floor
View of back of house
Living room
Kitchen
Exceptional
(7 reviews)

Fairfield Beach Modern Colonial

Fairfield

8% off
AU$12,384
for 7 nights, 1 home
AU$1,769 per night
includes taxes & fees
Fairfield Beach Modern Colonial
Movie room with 85" 4k screen and surround sound Sonos System
Gorgeous sunsets every night
Steam shower
Private kitchen
Exceptional
(55 reviews)

Litchfield County Four Season Country Paradise

Roxbury

8% off
AU$11,620
for 7 nights, 1 home
AU$1,660 per night
includes taxes & fees
Litchfield County Four Season Country Paradise
Living Room
Sunset
Bedroom 1: King
Kitchen
Exceptional
(9 reviews)

6-Acre Luxurious Country Home with Goddess Point Lookout

Woodbury

8% off
AU$17,996
for 7 nights, 1 home
AU$2,571 per night
includes taxes & fees
6-Acre Luxurious Country Home with Goddess Point Lookout
Property grounds
Interior
Interior
Interior
Exceptional
(20 reviews)

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

Brookfield

17% off
AU$17,815
for 7 nights, 1 home
AU$2,545 per night
includes taxes & fees
Beautiful, Fun Lakefront Retreat -- Perfect for family reunions / groups
Property grounds
Terrace/patio
Dining
Pool
Exceptional
(5 reviews)

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

Trumbull

8% off
AU$14,476
for 7 nights, 1 home
AU$2,068 per night
includes taxes & fees
Lake house cozy to relax with a family. 6 bedroom very spacious house.
Pool
Living area
Terrace/patio
Living area
Exceptional
(5 reviews)

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

Fairfield

8% off
AU$26,103
for 7 nights, 1 home
AU$3,729 per night
includes taxes & fees
2 Beautiful Homes, 1 Stunning Retreat: Pool HotTub Pizza Oven + Near Beach & NYC
Interior
Living area
Private kitchen
Property grounds
Exceptional
(9 reviews)

Renovated Milford Beach home by Charles Island/Silver Sands Pk

Milford

8% off
AU$3,989
for 7 nights, 1 cottage
AU$570 per night
includes taxes & fees
Renovated Milford Beach home by Charles Island/Silver Sands Pk
Fully stocked kitchen with stainless steel appliances and breakfast counter
Enjoy lounging after a long beach day on the sectional looking out at the water
Exterior
Large comfortable sectional with a 70" smart tv
Exceptional
(10 reviews)

Luxury Beach Oasis with Amazing Panoramic Ocean Views

Milford

8% off
AU$8,303
for 7 nights, 1 home
AU$1,186 per night
includes taxes & fees
Luxury Beach Oasis with Amazing Panoramic Ocean Views
Dining
Outdoor dining
Interior
Property grounds
Exceptional
(5 reviews)

On the Water Spacious Comfortable Historic Home

West Haven

8% off
AU$9,717
for 7 nights, 1 home
AU$1,388 per night
includes taxes & fees
On the Water Spacious Comfortable Historic Home
Bar (on property)
Dining
Property grounds
Golf
Exceptional
(71 reviews)

Northport quaint restored Boathouse with sunset views!

Northport

8% off
AU$4,204
for 7 nights, 1 cottage
AU$601 per night
includes taxes & fees
Northport quaint restored Boathouse with sunset views!
Room
Outdoor dining
Interior
Property grounds
Exceptional
(20 reviews)

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

Holmes

8% off
AU$6,850
for 7 nights, 1 home
AU$979 per night
includes taxes & fees
Beautiful lake view home on Whaley Lake in Holmes, NY.
Private kitchen
Interior
Property grounds
Property grounds
Exceptional
(30 reviews)

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

Danbury

8% off
AU$10,992
for 7 nights, 1 home
AU$1,570 per night
includes taxes & fees
Candlewood Lake - Family Getaway with direct lake access. 3775 sqft home.
Bedroom 2
Outdoor dining
Living area
Living area
Exceptional
(6 reviews)

Silver Sands Beach Getaway

Milford

16% off
AU$4,393
for 7 nights, 1 home
AU$628 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
AU$17,682
for 7 nights, 1 home
AU$2,526 per night
includes taxes & fees
Entertainers Dream, Candlewood Lake, Hot Tub,Disco,Theatre,Music studio..more!
Guests love spending quality time together in the living room
Property grounds
Lovely outdoor area and screened in porch to enjoy nature (without the bugs!)
Seating area in kitchen close to the screened in porch
Exceptional
(84 reviews)

Historic Warren/Kent Home

Cornwall Bridge

8% off
AU$3,693
for 7 nights, 1 home
AU$528 per night
includes taxes & fees
Historic Warren/Kent Home
Living area
Children’s area
Interior
Private kitchen
Exceptional
(49 reviews)

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

Greenwich

7% off
AU$3,291
for 7 nights, 1 home
AU$470 per night
includes taxes & fees
Quaint duplex with private yard. Walk to beach, dining, & shopping!
Room
Private kitchen
Interior
Dining
Exceptional
(6 reviews)

Darien family home on a Cul de Sac with pond.

Darien

8% off
AU$8,920
for 7 nights, 1 home
AU$1,274 per night
includes taxes & fees
Darien family home on a Cul de Sac with pond.
Dining
Property grounds
Interior
Private kitchen
Exceptional
(7 reviews)

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

Holmes

8% off
AU$3,999
for 7 nights, 1 home
AU$571 per night
includes taxes & fees
A Peaceful Bucolic Retreat by the Water at the Gateway of Hudson Valley
Exterior
Well stocked newly renovated kitchen. Prepare quick breakfast or a holiday meal.
Dining room seats 6 and expands for 8 with leaf.
Comfortable Living Room with 42" Smart TV.
Exceptional
(14 reviews)

Quiet suburban home close to Fairfield beaches and universities

Fairfield

8% off
AU$3,085
for 7 nights, 1 home
AU$441 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.
The pool and the lounge area available from May- September.
Spiral staircase leading to the mezzanine where the bedroom is located.
Exceptional
(16 reviews)

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

Brewster

25% off
AU$2,384
for 7 nights, 1 room
AU$341 per night
includes taxes & fees
The Cottage by the Lake: Hudson Valley Indulgence/1 hr. from NYC/welcome pets!.
Outdoor dining
Marina
Exterior
Interior
Exceptional
(14 reviews)

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

Stamford

7% off
AU$1,891
for 7 nights, 1 apartment
AU$270 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!
Interior
Living area
Exceptional
(46 reviews)

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

Milford

8% off
AU$3,339
for 7 nights, 1 apartment
AU$477 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
AU$3,138
for 7 nights, 1 apartment
AU$448 per night
includes taxes & fees
Beach Apartment in Woodmont Milford

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)
  • 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. 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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