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Fairfield Vacations

Pack those stellar shades. We have Fairfield vacation deals for you!

If there’s one thing you should spend in this busy world, it’s your vacation days. We know it’s easy to hang onto them, but Hotwire votes for putting them to use. It’s time to let an adventure lead you away from the daily grind. Stock up on what really matters on your trip to Fairfield – great memories and a tall tale or two.

Hotwire can help you find your travel bliss with Fairfield vacation packages. Bundling your hotel, car and flight means more unexpected fun with the money you saved. We’ll cover the bases; now it’s time for you to get up and go!

Pack everything you want – then take half of it out

We mean it. It’s far too easy to over-pack. We recommend picking your essentials and washing them along the way. Then you’ll have room for that goofy souvenir you know you want – or for some new outfits from that cute boutique you discover.

Bring comfortable walking shoes on your trip to Fairfield

No one should have to endure walking tours in dress shoes or high heels. No one.

Bring photocopies of your passport or license

You flew home from a great Fairfield vacation but your most important documents stayed behind. We’ve heard that story before and recommend keeping an extra copy on hand – just in case. Hey, at least it wasn’t a family member.

Don’t underestimate the power of earplugs

Among crying babies, rowdy crowds and honking horns, take our word for it. One pair can save you from the zombie-like state of a sleepless night.

Always carry some cash

You’ll be ready for anything from an evil ATM to lost credit cards. Holding a little extra cash in your wallet and carry-on means you can breathe easy if anything unexpected pops up.

Explore like a local

Guidebooks and maps are great for getting an overview of the place, but to really dig in, go where the locals go. Pick up a newspaper or city magazine to see what restaurants and neighborhoods are hot. Check events listings and go see a band or attend a street festival. Or ask your friends for recommendations. You’d be surprised who in your circle knows Fairfield well.

Top Hotel Deals

See all 128 Hotels in Fairfield
The Circle Hotel Fairfield

The Circle Hotel Fairfield

417 Post Road, Fairfield
3.5 out of 5.0

Located in the heart of Fairfield, this hotel is 1.4 mi (2.2 km) from Regina A. Quick Center for the Arts.

$85

$85
Best Western Plus Fairfield Hotel

Best Western Plus Fairfield Hotel

100 Kings Highway Cutoff, Fairfield
2.5 out of 5.0

Located in the heart of Fairfield, this hotel is within 2 mi (3 km) of Fairfield University, Regina A. Quick Center for the Arts, and Longfellow Park. South ...

$85

$85
Hotel Hi-Ho

Hotel Hi-Ho

4180 Black Rock Turnpike, Fairfield
3.5 out of 5.0

Situated in Fairfield, this motel is 1.2 mi (1.9 km) from H. Smith Richardson Golf Course and within 3 mi (5 km) of Greenfield Hill Historic District and Fairchild ...

$85

$85
The Inn at Fairfield Beach

The Inn at Fairfield Beach

1160 Reef Road, Fairfield
3.0 out of 5.0

Situated by the ocean, this bed & breakfast is within 1 mi (2 km) of Fairfield Theater Company and Fairfield Museum and History Center. Connecticut Audubon Birdcraft ...

$108

$108
Hyatt Place Milford / New Haven

Hyatt Place Milford / New Haven

190 Old Gate Lane, Milford
3.5 out of 5.0

Just off highway I-95, Hyatt Place Milford / New Haven is a 5-minute drive from Westfield Connecticut Post shopping mall. Trains from nearby Milford Station ...

$86

$86
Danfords Hotel and Marina

Danfords Hotel and Marina

25 E Broadway, Port Jefferson
4.0 out of 5.0

Located in the heart of Port Jefferson, this spa hotel is steps from Harborfront Park, Maritime Explorium, and Port Jefferson. Theatre Three and Mather House ...

$96

$96
Motel 6 Milford

Motel 6 Milford

111 Schoolhouse Road, Milford
3.0 out of 5.0

Situated in the business district, this hotel is within 3 mi (5 km) of Silver Sands State Park, Port Milford, and Milford Plaza Shopping Center. Perry House ...

$58

$58
EVEN Hotel Norwalk

EVEN Hotel Norwalk

426 Main Ave, Norwalk
4.0 out of 5.0

Situated in the business district, this hotel is within 1 mi (2 km) of Caldor Shopping Center, Center Seven Shopping Center, and Gateway Shopping Center. Silvermine ...

$84

$84
Hyatt Regency Greenwich

Hyatt Regency Greenwich

1800 E Putnam Avenue, Old Greenwich
4.5 out of 5.0

This Hyatt Regency hotel, located on the Stamford/Greenwich border, is minutes from both the heart of downtown Stamford and shopping on Greenwich Avenue. New ...

$107

$107
Trumbull Marriott Merritt Parkway

Trumbull Marriott Merritt Parkway

180 Hawley Ln, Trumbull
4.0 out of 5.0

Situated in the suburbs, this hotel is 2.6 mi (4.2 km) from Boothe Memorial Park and Museum and 2.8 mi (4.5 km) from Beardsley Zoo. National Helicopter Museum ...

$101

$101

Top Flight Deals

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.