Book Holiday Homes in Fairfield

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Featured Holiday Homes in Fairfield

Business or Weekend escape

Business or Weekend escape

Stratford
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
Lower Lvl Private 2BR/1BA Family/Pet Friendly

Lower Lvl Private 2BR/1BA Family/Pet Friendly

Stamford
Stay at this vacation home in Stamford. Enjoy free WiFi, a fitness center, and a garden. Popular attractions E. Gaynor Brennan Golf Course and Hand & Stone Massage ...
Lower Lvl Private 2BR/1BA Family/Pet Friendly
Beautiful historic home in Stony Brook!

Beautiful historic home in Stony Brook!

2 out of 5
Stony Brook
Stay at this vacation home in Stony Brook. Enjoy air conditioning. Popular attractions Stony Brook Grist Mill and Long Island Museum of American Art, History, ...
Beautiful historic home in Stony Brook!
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Lakeview Estate - Chef's Kitchen - NYC Getaway

Lakeview Estate - Chef's Kitchen - NYC Getaway

Danbury
Stay at this vacation home in Danbury. Enjoy a garden, patios, and in-room jetted tubs. Popular attractions Danbury Duckpin Lanes and Hatters Park are located ...
Lakeview Estate - Chef's Kitchen - NYC Getaway
Beautiful, Spacious, Beachfront Home - Perfect for Entertaining Family & Friends

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

West Haven
Book a stay at this beach vacation home in West Haven. Enjoy free WiFi, a beach locale, and patios. Popular attractions Seabluff Beach and Bradley Point Beach ...
Beautiful, Spacious, Beachfront Home - Perfect for Entertaining Family & Friends
Cozy Modern Home

Cozy Modern Home

West Haven
Stay at this vacation home in West Haven. Enjoy free WiFi, a garden, and an in-room coffeemaker. Popular attractions Savin Rock Conference Center and Oak Street ...
Cozy Modern Home
Private French Country Estate-New Canaan CT-Pool-Film Set-Dec avail

Private French Country Estate-New Canaan CT-Pool-Film Set-Dec avail

New Canaan
Stay at this vacation home in Fairfield County. Enjoy private pools, a water park, and a fitness center. Popular attractions Silvermine Arts Center and Caldor ...
Private French Country Estate-New Canaan CT-Pool-Film Set-Dec avail
Milford Oasis: 2BR, Wi-Fi, Near Walnut Beach

Milford Oasis: 2BR, Wi-Fi, Near Walnut Beach

Milford
Stay at this vacation home in Milford. Enjoy a garden, patios, and an in-room coffeemaker. Popular attractions Walnut Beach and The Coastal Center at Milford ...
Milford Oasis: 2BR, Wi-Fi, Near Walnut Beach
Stylish Beach Home near Stamford Downtown/Beach

Stylish Beach Home near Stamford Downtown/Beach

Stamford
Book a stay at this family-friendly vacation home in Stamford. Enjoy a garden, patios, and an in-room coffeemaker. Popular attractions Cove Island Park and Chelsea ...
Stylish Beach Home near Stamford Downtown/Beach
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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
331 Holiday Homes
Lowest Price
NZ$219
Highest Price
NZ$296
Popular accommodation
Business or Weekend escape, Lower Lvl Private 2BR/1BA Family/Pet Friendly, Beautiful historic home in Stony Brook!, Lakeview Estate - Chef's Kitchen - NYC Getaway, Beautiful, Spacious, Beachfront Home - Perfect for Entertaining Family & Friends, Cozy Modern Home, Private French Country Estate-New Canaan CT-Pool-Film Set-Dec avail, Milford Oasis: 2BR, Wi-Fi, Near Walnut Beach, Stylish Beach Home near Stamford Downtown/Beach

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$259 per night from 25 Nov to 26 Nov
NZ$259
includes taxes & fees
25 Nov - 26 Nov
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$219 per night from 5 Dec to 6 Dec
NZ$219
includes taxes & fees
5 Dec - 6 Dec
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$296 per night from 25 Nov to 26 Nov
NZ$296
includes taxes & fees
25 Nov - 26 Nov
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
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DUNE Fairfield Beach

DUNE Fairfield Beach

3 out of 5
1160 Reef Rd, Fairfield, CT
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?
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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.

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