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
When you stay at this vacation home in Weston, you'll be within a 10-minute drive of Wilton Historical Society and Westport Historical Society.
Historic Connecticut Home w/ Grill & Spacious Yard
Lakeside luxury: beautiful, relaxing 4 bedroom home

Lakeside luxury: beautiful, relaxing 4 bedroom home

Trumbull
With a stay at this vacation home in Trumbull, you'll be within a 10-minute drive of Northeast Medical Group and Roosevelt Forest.
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
Located in Danbury, this vacation home is on the waterfront, a 1-minute drive from Candlewood Lake and 7 minutes from Candlewood Plaza Shopping Center.
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 AU$218 per night from 7 Apr to 8 Apr
AU$218
includes taxes & fees
7 Apr - 8 Apr
Located in Stratford, this vacation home is within a 5-minute drive of Perry House and Stratford Historical Society Capt David Judson House.
Business or Weekend escape
Cheerful 4 bedrooms residential house.

Cheerful 4 bedrooms residential house.

Bridgeport
When you a stay at this vacation home in Bridgeport, you'll be by the sea, just steps from Bridgeport Downtown South Historic District and University of ...
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
With a stay at this vacation home in Centereach, you'll be within a 5-minute drive of Stony Brook University and Smithaven Mall.
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
With a stay at this vacation home in Stamford (North Stamford), you'll be within a 10-minute drive of Yale New Haven Health Long Ridge Medical Center and Hoyt ...
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
Located in Westport, this vacation home is within a 5-minute drive of Westport Historical Society and Levitt Pavilion.
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
With a stay at this vacation home in New Haven (West New Haven), you'll be within a 15-minute drive of Yale University and Quinnipiac University.
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
432 Holiday Homes
Lowest Price
AU$185
Highest Price
AU$499
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 refundable
The price is AU$230 per night from 16 Apr to 17 Apr
AU$230
includes taxes & fees
16 Apr - 17 Apr
Located in Fairfield, The Circle Hotel Fairfield is in a shopping district, within a 5-minute drive of Fairfield University and Fairfield Museum and History ...
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 AU$185 per night from 9 Apr to 10 Apr
AU$185
includes taxes & fees
9 Apr - 10 Apr
With a stay at Hotel Hi-Ho - Contactless Check-In in Fairfield, you'll be within a 5-minute drive of Lake Mohegan and Sacred Heart University.
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 AU$273 per night from 6 Apr to 7 Apr
AU$273
includes taxes & fees
6 Apr - 7 Apr
A stay at Best Western Plus Fairfield Hotel places you in the heart of Fairfield, within a 5-minute drive of Fairfield University and Longfellow Park.
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 AU$499 per night from 10 Apr to 11 Apr
AU$499
includes taxes & fees
10 Apr - 11 Apr
Located in Fairfield, DUNE Fairfield Beach is near the beach, within a 5-minute walk of Fairfield Beach and Penfield Beach.
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.