Book Holiday Homes in Fairfield

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Featured Holiday Homes in Fairfield

Cozy Room in charming New Haven near Yale/Hospitals!

Cozy Room in charming New Haven near Yale/Hospitals!

New Haven CT
The price is AU$216 per night from 31 May to 1 June
AU$216
31 May - 1 June
includes taxes & fees
With a stay at this vacation home in New Haven (The Hill), you'll be within a 5-minute drive of Yale University and Yale-New Haven Hospital.
Opens in a new windowCozy Room in charming New Haven near Yale/Hospitals!
Beautiful, Spacious, Beachfront Home - Perfect for Entertaining Family & Friends

Beautiful, Spacious, Beachfront Home - Perfect for Entertaining Family & Friends

West Haven CT
When you stay at this vacation home in West Haven, you'll be on the beach, within a 10-minute drive of Yale University and Yale-New Haven Hospital.
Opens in a new windowBeautiful, Spacious, Beachfront Home - Perfect for Entertaining Family & Friends
Beautiful Renovated Direct Waterfront Candlewood Lake Home~Views~Weekly Discount

Beautiful Renovated Direct Waterfront Candlewood Lake Home~Views~Weekly Discount

Danbury CT
Located in Danbury, this vacation home is on the waterfront, a 2-minute drive from Candlewood Lake and 7 minutes from Candlewood Plaza Shopping Center.
Opens in a new windowBeautiful Renovated Direct Waterfront Candlewood Lake Home~Views~Weekly Discount
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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 NY
With a stay at this vacation home in Centereach, you'll be within a 5-minute drive of Stony Brook University and Smithaven Mall.
Opens in a new windowCozy 4-bedroom house with AC and WiFi in Centereach, New York.
Charming Home in Seaside

Charming Home in Seaside

Bridgeport CT
With a stay at this vacation home in Bridgeport (South End), you'll be within a 10-minute walk of Hartford HealthCare Amphitheater and University of ...
Opens in a new windowCharming Home in Seaside
Beautiful Fairfield Beach Area home, 5 minute walk to beach, town & train

Beautiful Fairfield Beach Area home, 5 minute walk to beach, town & train

Fairfield CT
With a stay at this vacation home in Fairfield (Fairfield Beach), you'll be within a 10-minute drive of Hartford HealthCare Amphitheater and Fairfield ...
Opens in a new windowBeautiful Fairfield Beach Area home, 5 minute walk to beach, town & train
2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.

2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.

Greenwich CT
The price is AU$449 per night from 20 May to 21 May
AU$449
20 May - 21 May
includes taxes & fees
Located in Greenwich, this vacation home is a 3-minute drive from Houston Preserve and 9 minutes from Caldwell Sanctuary.
Opens in a new window2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.
Beach Bungalow, walk to beach, private backyard

Beach Bungalow, walk to beach, private backyard

West Haven CT
When you stay at this vacation home in West Haven, you'll be near the beach, within a 10-minute drive of Yale University and Yale-New Haven Hospital.
Opens in a new windowBeach Bungalow, walk to beach, private backyard
Dog-Friendly Oceanfront Getaway - Walk to Dining - Private Beach Access

Dog-Friendly Oceanfront Getaway - Walk to Dining - Private Beach Access

Milford CT
When you stay at this vacation home in Milford, you'll be on the beach, within a 15-minute drive of Yale University and Yale-New Haven Hospital.
Opens in a new windowDog-Friendly Oceanfront Getaway - Walk to Dining - Private Beach Access
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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
399 Holiday Homes
Lowest Price
AU$185
Highest Price
AU$449
Popular accommodation
Cozy Room in charming New Haven near Yale/Hospitals!, Beautiful, Spacious, Beachfront Home - Perfect for Entertaining Family & Friends, Beautiful Renovated Direct Waterfront Candlewood Lake Home~Views~Weekly Discount, Cozy 4-bedroom house with AC and WiFi in Centereach, New York. , Charming Home in Seaside, Beautiful Fairfield Beach Area home, 5 minute walk to beach, town & train , 2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich., Beach Bungalow, walk to beach, private backyard, Dog-Friendly Oceanfront Getaway - Walk to Dining - Private Beach Access

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$204 per night from 25 May to 26 May
AU$204
25 May - 26 May
includes taxes & fees
Located in Fairfield (Grasmere), The Circle Hotel Fairfield is within a 5-minute drive of Fairfield University and Fairfield Museum and History Center.
Opens in a new windowThe 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 19 May to 20 May
AU$185
19 May - 20 May
includes taxes & fees
Located in Fairfield (Greenfield Hill), Hotel Hi-Ho - Contactless Check-In is within a 5-minute drive of Lake Mohegan and Sacred Heart University.
Opens in a new windowHotel 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$238 per night from 26 May to 27 May
AU$238
26 May - 27 May
includes taxes & fees
With a stay at Best Western Plus Fairfield Hotel, you'll be centrally located in Fairfield, within a 5-minute drive of Hartford HealthCare Amphitheater and Fairfield ...
Opens in a new windowBest Western Plus Fairfield Hotel
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DUNE Fairfield Beach

DUNE Fairfield Beach

3 out of 5
1160 Reef Rd Fairfield CT
The price is AU$364 per night from 26 May to 27 May
AU$364
26 May - 27 May
includes taxes & fees
With a stay at DUNE Fairfield Beach in Fairfield (Fairfield Beach), you'll be within a 10-minute drive of Hartford HealthCare Amphitheater and Fairfield ...
Opens in a new windowDUNE Fairfield Beach
Don't see what you're looking for?
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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.

Top Picks

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^Subject to availability and chosen travel dates.