Fairfield Vacations from $453

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Your Fairfield Vacation

With every last detail planned before you take off, our Fairfield vacation packages mean you can simply focus on enjoying your getaway. Whether you're based in the neighborhood of Black Rock Historic District, which is good for history, or another area, this exciting city promises a world of discoveries. Ready to explore your surroundings? Fairfield University, Sacred Heart University and Total Mortgage Arena are among the top places to visit during a trip to Fairfield. Don't put off your visit to this destination any longer. The perfect Fairfield vacation is a few clicks away with Expedia.

The Latest Fairfield vacation packages

Price found within the past 48 hours. Click for updated prices.
The Circle Hotel Fairfield

The Circle Hotel Fairfield

3 out of 5
Save 100% on your flight
Price was $585, price is now $453 per person
$453
per person
Sep 26 - Sep 28
found 24 hours ago
Roundtrip flight included
Miami (MIA) to New York (LGA)
9/10 Wonderful! (1,391 reviews)
You should add variety to your breakfasts.

Reviewed on Aug 13, 2025

The Sagaponack

The Sagaponack

3 out of 5
Price was $932, price is now $787 per person
$787
per person
Nov 13 - Nov 17
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to New York (LGA)
8.8/10 Excellent! (165 reviews)
Great experience. Comfortable beds pool was heated to the perfect temperature. Overall atmosphere is great.

Reviewed on Jul 5, 2025

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Discover the most popular places to visit in Fairfield

Jennings Beach

Why not spend a carefree afternoon at Jennings Beach during your travels in Fairfield? Visit the shops in this family-friendly area, or simply enjoy its restaurants.

Jennings Beach

Penfield Beach

If a restful vacation is part of your travel plans, Penfield Beach might be the perfect place to seek out during your trip to Fairfield. Visit the shops in this family-friendly area, or simply enjoy its restaurants.

Penfield Beach

Fairchild Wheeler Golf Course

Enjoy a round of golf in Fairfield at Fairchild Wheeler Golf Course. Stroll along the beautiful beaches or attend a sporting event in this family-friendly area.

Fairchild Wheeler Golf Course

Fairfield Hotel Deals

The Circle Hotel Fairfield

The Circle Hotel Fairfield

3 out of 5
417 Post Road, Fairfield, CT
Fully refundableReserve now, pay when you stay
$169 nightly
The price is $194 total per night from Aug 26 to Aug 27
$194 total
Aug 26 - Aug 27
Total includes taxes and fees
8.8/10 Excellent! (1,384 reviews)
"Service is great at Circle Hotel, a clean, nice, excellent location hotel. People make the difference here."

Reviewed on Aug 19, 2025

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
$149 nightly
The price is $171 total per night from Sep 1 to Sep 2
$171 total
Sep 1 - Sep 2
Total includes taxes and fees
7.8/10 Good! (1,000 reviews)
"This property was just fine. We were on the first floor corner, right next to the parking. It was a little loud. The bed comfort was about a 6.5/10. The room was clean, but that cleaning product had a funky smell. Overall, I would probably stay there again if there was no other option."

Reviewed on Aug 18, 2025

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
$150 nightly
The price is $172 total per night from Aug 24 to Aug 25
$172 total
Aug 24 - Aug 25
Total includes taxes and fees
7.8/10 Good! (1,002 reviews)
"Great place and convince"

Reviewed on Aug 9, 2025

Best Western Plus Fairfield Hotel
See all 1,301 properties in Fairfield
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 Beach Vacation

There's nothing like a Fairfield vacation to give yourself a little boost. The soothing melody of rolling surf and the smell of clean ocean air are sure to rejuvenate your mind, body and soul. To be close to the city center on your trip to Fairfield, base yourself around Jennings Beach (1 mile away). If you're intending to hang around a while, consider securing one of our Fairfield packages. Not only will you save some money, you'll also have other stunning beaches around you to explore, like South Pine Creek Beach and Sasco Hill Beach. Now that's a win-win!

Things You Should Know About Fairfield

  • If ocean breezes and strolls along the shore are your idea of a dream vacation, why not opt for one of our Fairfield beach hotels? Staying by the water is the perfect cure for life's daily stresses.
  • Alternatively, browse our range of private vacation homes. They're a hit with travelers planning a stay in Fairfield. Consider Best Western Plus Fairfield Hotel and The Circle Hotel Fairfield.
  • Fairfield has a population of roughly 59,100 people. Why not get out and have a conversation with one or two of them? It's an excellent way to get some inside intel on the place! Also look up our Fairfield things to do page.
  • After you've made some great savings by booking a Fairfield vacation package, you can splurge on unforgettable travel experiences. Sacred Heart University, Fairfield University and Jennings Beach are a few attractions that should be on your must-see list.

Things to do in and around Fairfield

Fairfield, Connecticut, offers a delightful mix of city-themed and outdoor activities perfect for a vacation. Visitors can indulge in relaxing spa packages, explore educational and recreational areas, and enjoy family day trips. The shopping scene is vibrant, making it ideal for weekend getaways from nearby Westport. Don't miss the chance to experience exciting dive shows and unwind at a tranquil spa, ensuring a memorable stay in this charming coastal town.

Shopping

For a delightful shopping experience in Fairfield, visit the Westport Farmers Market, just 5 miles away, for local goods and city vibes. The Caldor Shopping Center, located 8 miles away, offers a mix of business and family-friendly options. If you're up for a drive, check out The SoNo Collection, 9 miles away, for an upscale shopping experience.

Recreation

Experience exhilarating concerts at the Hartford HealthCare Amphitheater, just 4 miles away, where sports and music unite. Unwind at Seaside Park, also 4 miles from Fairfield, offering serene walks and relaxation. Enjoy cultural performances at the Fairfield Theater Company, a hub of entertainment and family fun right in town.

Adventure

Experience thrilling ziplining and ropes courses at The Adventure Park at Discovery Museum, located 5 miles from Fairfield. Enjoy water sports at Waterski Connecticut, 16 miles away, or challenge yourself at Wolfe Park Tennis Center, 12 miles from town, where adventure awaits at every turn.

Nightlife

Fairfield's nightlife buzzes with energy, featuring cozy bars and vibrant music scenes. Visit The Warehouse on Black Rock Turnpike for craft cocktails and DJs, or check out The Fairfield Theatre Company for live performances and events. Enjoy a lively atmosphere and great company throughout the night.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Find the best attractions in and around Fairfield

Fairfield, Connecticut offers a delightful mix of city-themed and outdoor adventures, perfect for cultural and family experiences. Explore beautiful beaches, urban parks, and modern colleges while enjoying the area's vibrant atmosphere. Don't miss out on relaxing at Fairfield Beach, and consider nearby hotels for a comfortable stay. Whether you're seeking adventure or a peaceful retreat, Fairfield has something for everyone.

  • Fairfield University: Experience the vibrant atmosphere of this modern university, known for its beautiful campus and dynamic student life. Stroll through the grounds, enjoy art installations, and perhaps catch a cultural event or lecture.
  • Jennings Beach: Relax at this picturesque beach, perfect for sunbathing, swimming, or a leisurely walk along the shore. With its inviting sand and stunning views, Jennings Beach is an ideal spot for families and beach lovers alike.
  • Bridgeport Downtown South Historic District: Immerse yourself in the rich history and culture of this charming district. Explore its historic architecture, visit local shops, and enjoy art galleries that showcase the area’s unique heritage, just 5 miles from Fairfield.

Tips to save on your trip to Fairfield

  • Combine your flights, hotels and car rentals on Expedia—bundling can result in significant savings.
  • Consider traveling during the off-peak season (typically January to March) for more affordable package holidays to Fairfield.
  • Use the Price per traveler filter on Expedia to find a package deal that suits your budget.
  • Check the VIP Access properties filter to discover outstanding hotels with added member perks at select properties.

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Frequently asked questions

How much does a Fairfield vacation package cost?
You can grab a vacation package to this destination from $453 on Expedia. However, how much your vacation to Fairfield costs will depend on factors like the season, hotel choice and length of stay.
What are the cheapest months to go to Fairfield?
If you'd like to snag a cheap Fairfield vacation package, consider visiting in November, December and January. You'll usually find better rates on flights and hotels during these quieter months — perfect for a budget-friendly getaway.
How many days is enough for Fairfield?
We recommend planning a Fairfield vacation for at least 2 days. This will give you enough time to visit key attractions including South Pine Creek Beach and Sasco Hill Beach, and check out neighborhoods like Black Rock Gardens Historic District and Black Rock Historic District. You could even fit in a day trip from Fairfield.
Is it worth booking a vacation package to Fairfield?
Fairfield is a good vacation destination with attractions like Jennings Beach among the many things to keep you busy. Whether you're heading away with the family or getting away with friends, a Fairfield vacation promises fun for everyone.
How to find the best Fairfield package deals?
Finding a cheap Fairfield package deal is a cinch with Expedia. Once you've entered your preferred dates and destination under our "Packages" tab, set your maximum budget, apply a couple of filters and see what's available. You can customize your search by "Amenities," "Property type," "Popular locations" and more. Order the results by "Price: low to high" to discover the most affordable Fairfield package deals. Want a simple trick to score the biggest savings? Have some flexibility with your departure dates and consider going away on a weekday, when prices are typically lower.
Is it cheaper to book a Fairfield vacation as a package?
You can enjoy significant savings on your Fairfield getaway by booking a tailored vacation package. Click on the "Package" heading, then select your travel dates and destination to see some great flight and hotel prices. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a car rental and you may land a better deal.
When to book a vacation package to Fairfield?
If you're planning a spur-of-the-moment Fairfield trip, check out our last-minute deals that can be booked up to one week before you take off. Prefer not to wait until the last minute? You can land terrific deals on your hotels and flights by booking ahead.
Does Expedia offer Book Now, Pay Later Fairfield vacation packages?
Secure your dream trip to Fairfield with our Book Now, Pay Later vacations. There's no need to save up or wait for your next payday — we've joined forces with online lender Affirm to give you more flexibility and choice. Our vacation packages with payment plans let you spread the cost over 3, 6 or 12 months. With no late payment fees or extra charges, it's a breeze to stay on budget and snap up cheap deals while they last.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.