Book Holiday Homes in Fairfield

More Flash, Less Cash - Take advantage of our Price Pledge** (even on luxey stays)

We keep it easy with the option to pay now or later on select accommodation

Book up 'til the last second - millions of rooms to crash tonight^

Featured Holiday Homes in Fairfield

Historic Connecticut Home w/ Grill & Spacious Yard

Historic Connecticut Home w/ Grill & Spacious Yard

Weston
Stay at this vacation home in Weston. Enjoy patios, cable/satellite TV service, and an in-room coffeemaker. Popular attractions Wilton Historical Society and ...
Historic Connecticut Home w/ Grill & Spacious Yard
Lakeside luxury: beautiful, relaxing 4 bedroom home

Lakeside luxury: beautiful, relaxing 4 bedroom home

Trumbull
Stay at this vacation home in Trumbull. Enjoy a garden, patios, and an in-room coffeemaker. Popular attractions Roosevelt Forest and Beardsley Zoo are located ...
Lakeside luxury: beautiful, relaxing 4 bedroom home
Charming Direct Waterfront Home w/Panoramic Views and Hot Tub on Candlewood Lake

Charming Direct Waterfront Home w/Panoramic Views and Hot Tub on Candlewood Lake

Danbury
Stay at this vacation home in Danbury. Enjoy free WiFi, patios, and cable/satellite TV service. Popular attractions Bear Mountain Reservation and Candlewood ...
Charming Direct Waterfront Home w/Panoramic Views and Hot Tub on Candlewood Lake
Save an average of 15% on thousands of hotels when you're signed in
Business or Weekend escape

Business or Weekend escape

Stratford
The price is NZ$236 per night from 13 Apr to 14 Apr
NZ$236
includes taxes & fees
13 Apr - 14 Apr
Stay at this vacation home in Stratford. Enjoy an in-room coffeemaker and air conditioning. Our guests praise the helpful staff in our reviews. Popular attractions ...
Business or Weekend escape
Cheerful 4 bedrooms residential house.

Cheerful 4 bedrooms residential house.

Bridgeport
Stay at this vacation home in Bridgeport. Enjoy patios, an in-room coffeemaker, and air conditioning. Popular attractions Hartford HealthCare Amphitheater and ...
Cheerful 4 bedrooms residential house.
Cozy 4-bedroom house with AC and WiFi in Centereach, New York.

Cozy 4-bedroom house with AC and WiFi in Centereach, New York.

Centereach
Stay at this vacation home in Centereach. Enjoy air conditioning. Popular attractions AMF Centereach Lanes and Smithaven Mall are located nearby.
Cozy 4-bedroom house with AC and WiFi in Centereach, New York.
Bright Stylish Chic 4BR 4BA Home Pet Friendly!

Bright Stylish Chic 4BR 4BA Home Pet Friendly!

Stamford
Book a stay at this family-friendly vacation home in Stamford. Enjoy a garden, patios, and cable/satellite TV service. Popular attractions Houston Preserve and ...
Bright Stylish Chic 4BR 4BA Home Pet Friendly!
Main Street Westport, walk to shops, dining, downtown

Main Street Westport, walk to shops, dining, downtown

Westport
Stay at this vacation home in Westport. Enjoy an in-room coffeemaker and air conditioning. Popular attractions Levitt Pavilion and Westport Country Playhouse ...
Main Street Westport, walk to shops, dining, downtown
7Mins to Yale I ENTIRE HOUSE I Large fenced yard I King bed I 3BR I Group Gather

7Mins to Yale I ENTIRE HOUSE I Large fenced yard I King bed I 3BR I Group Gather

New Haven
Stay at this vacation home in New Haven. Enjoy free WiFi, a garden, and in-room jetted tubs. Popular attractions Yale Golf Course and Yale Bowl are located ...
7Mins to Yale I ENTIRE HOUSE I Large fenced yard I King bed I 3BR I Group Gather
Don't see what you're looking for?
See all available properties in Fairfield
View all properties
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Fairfield Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Fairfield vacation homes are the perfect way for you to wing it.

Holiday houses in Fairfield let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Fairfield in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Fairfield adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Fairfield with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Fairfield vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Fairfield Holiday Homes essential information

Accommodation
425 Holiday Homes
Lowest Price
NZ$203
Highest Price
NZ$549
Popular accommodation
Historic Connecticut Home w/ Grill & Spacious Yard, Lakeside luxury: beautiful, relaxing 4 bedroom home, Charming Direct Waterfront Home w/Panoramic Views and Hot Tub on Candlewood Lake, Business or Weekend escape, Cheerful 4 bedrooms residential house., Cozy 4-bedroom house with AC and WiFi in Centereach, New York. , Bright Stylish Chic 4BR 4BA Home Pet Friendly!, Main Street Westport, walk to shops, dining, downtown, 7Mins to Yale I ENTIRE HOUSE I Large fenced yard I King bed I 3BR I Group Gather

Top trending hotels in Fairfield

The Circle Hotel Fairfield

The Circle Hotel Fairfield

3 out of 5
417 Post Road, Fairfield, CT
Fully refundableReserve now, pay when you stay
The price is NZ$229 per night from 7 Apr to 8 Apr
NZ$229
includes taxes & fees
7 Apr - 8 Apr
Stay at this 3-star beach hotel in Fairfield. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our reviews. ...
The Circle Hotel Fairfield
Hotel Hi-Ho - Contactless Check-In

Hotel Hi-Ho - Contactless Check-In

3 out of 5
4180 Black Rock Turnpike, Fairfield, CT
Fully refundableReserve now, pay when you stay
The price is NZ$203 per night from 9 Apr to 10 Apr
NZ$203
includes taxes & fees
9 Apr - 10 Apr
Stay at this 3-star motel in Fairfield. Enjoy free WiFi, free parking, and room service. Our guests praise the restaurant and the clean rooms in our reviews. ...
Hotel Hi-Ho - Contactless Check-In
Best Western Plus Fairfield Hotel

Best Western Plus Fairfield Hotel

2.5 out of 5
100 Kings Highway Cutoff, Fairfield, CT
Fully refundableReserve now, pay when you stay
The price is NZ$300 per night from 6 Apr to 7 Apr
NZ$300
includes taxes & fees
6 Apr - 7 Apr
Book a stay at this business-friendly hotel in Fairfield. Enjoy free breakfast, free parking, and a 24-hour fitness center. Our guests praise the helpful staff ...
Best Western Plus Fairfield Hotel
Save an average of 15% on thousands of hotels when you're signed in
DUNE Fairfield Beach

DUNE Fairfield Beach

3 out of 5
1160 Reef Rd, Fairfield, CT
The price is NZ$549 per night from 7 Apr to 8 Apr
NZ$549
includes taxes & fees
7 Apr - 8 Apr
Stay at this 3-star beach apartment in Fairfield. Enjoy free WiFi, free parking, and free bicycles on site. Popular attractions Penfield Beach and Fairfield ...
DUNE Fairfield Beach
Don't see what you're looking for?
See all available properties in Fairfield
View all properties
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.