Fairfield Vacations from $445

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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.
Best Western Plus Fairfield Hotel

Best Western Plus Fairfield Hotel

2.5 out of 5
Grasmere
Price was $474, price is now $445 per person
$445
per person
Apr 2 - Apr 5
found 1 day ago
Roundtrip flight included
San Juan (SJU) to New York (LGA)
8/10 Very Good! (1,000 reviews)
Such a nice little place

Reviewed on Nov 24, 2025

Windrose On Hudson

Windrose On Hudson

3 out of 5
Price was $1,324, price is now $876 per person
$876
per person
Mar 28 - Apr 3
found 10 hours ago
Roundtrip non-stop flight included
Burbank (BUR) to New York (LGA)
7.8/10 Good! (80 reviews)
The rooms need more amenities such as a coffee maker some cups and utensils, as well as a guide to the television set.

Reviewed on Dec 28, 2025

The Sagaponack

The Sagaponack

3 out of 5
Price was $1,025, price is now $912 per person
$912
per person
Mar 16 - Mar 22
found 12 hours ago
Roundtrip flight included
Los Angeles (QLA) to New York (LGA)
8.8/10 Excellent! (205 reviews)
The property and room was clean, easily accessible, and staff were very friendly. We would stay here again!

Reviewed on Jan 3, 2026

Wainscott Woods Retreat

Wainscott Woods Retreat

2.5 out of 5
Price was $1,417, price is now $1,328 per person
$1,328
per person
Mar 16 - Mar 22
found 12 hours ago
Roundtrip flight included
Los Angeles (QLA) to New York (LGA)
7/10 Good! (9 reviews)
Newly Renovated and extremely clean, well kept, and inviting rooms. Staff could not be nicer and more accommodating. Location is ideally situated close to lots of shops, Goldbergs for bagels, East Hampton Beaches etc. Highly recommend this accommodation to anyone staying in the area.

Reviewed on Oct 15, 2025

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Where to stay in Fairfield

Find the best Fairfield areas and neighborhoods for the activities you enjoy most. Learn more about Fairfield
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Fairfield Beach

4 out of top 10 points of interest in this area

If you're spending some time in Fairfield Beach, Penfield Beach and Fairfield Beach are top sights worth seeing.

Find hotels in Fairfield Beach

Discover the most popular places to visit in Fairfield

Jennings Beach

4.5/5(3 reviews)

If a restful vacation is part of your travel plans, Jennings Beach might be the perfect place to seek out during your trip to Fairfield. Stroll along the waterfront or discover the area's sunsets.

Jennings Beach

Penfield Beach

Why not spend a carefree afternoon at Penfield Beach during your travels in Fairfield? Discover the sunsets while you're in the area.

Penfield Beach

Pine Creek Par 3 Golf Course

Enjoy a round of golf in Fairfield at Pine Creek Par 3 Golf Course. While you're in the area, stroll along the beautiful beaches.

Pine Creek Par 3 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
$134 nightly
The price is $154 total per night from Feb 8 to Feb 9
$154 total
Feb 8 - Feb 9
Total with taxes and fees
8.8/10 Excellent! (1,429 reviews)
Room was great! The bed and couch was amazing! Coming again soon

Reviewed on Jan 18, 2026

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
$109 nightly
The price is $126 total per night from Feb 8 to Feb 9
$126 total
Feb 8 - Feb 9
Total with taxes and fees
7.8/10 Good! (1,001 reviews)
Clean room. Neat place. I was trying to sleep in. Checkout is 11:00. Cleaning person knocking on my door at 10:00. So that stunk. If you stay here, request a room opposite of the road. Probably much quieter.

Reviewed on Jan 17, 2026

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
$140 nightly
The price is $161 total per night from Jan 21 to Jan 22
$161 total
Jan 21 - Jan 22
Total with taxes and fees
8/10 Very Good! (1,004 reviews)
Very courteous staff. Room was OK, but insufficient shower curtain led to water on bathroom floor after shower.

Reviewed on Dec 28, 2025

Best Western Plus Fairfield Hotel
See all 1,351 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.

Find the Best Fairfield Vacation Packages

Things to do near Fairfield

Fairfield, Connecticut, offers a perfect blend of city and outdoor activities, making it ideal for cultural vacations. You can enjoy spa packages, family day trips, and relaxing weekends, while also exploring recreational areas and golf courses. Dive shows add to the excitement, making it a great destination for both relaxation and fun-filled adventures.

Shopping

The Westport Farmers Market, located 5 miles away, offers a vibrant public market experience with a local flair. For more extensive shopping, the Caldor Shopping Center is 8 miles away with a mix of businesses and family vibes. If you're up for a drive, the Westfield Connecticut Post Mall is 13 miles away, featuring entertainment and a variety of shops for all ages.

Recreation

Experience live events at the Hartford HealthCare Amphitheater, just 4 miles away, where the energetic atmosphere elevates your spirit. For a serene escape, visit Seaside Park, also 4 miles away, to enjoy nature walks and tranquil beachfront relaxation amidst lush greenery.

Adventure

At The Adventure Park at Discovery Museum, located 5 miles from Fairfield, experience thrilling zipline courses among the trees. Wolfe Park Tennis Center, 12 miles away, offers exciting tennis activities. For water sports enthusiasts, Waterski Connecticut, 16 miles from Fairfield, provides an exhilarating aquatic adventure.

Nightlife

Fairfield's nightlife offers a vibrant blend of bars and restaurants. Enjoy cocktails at The Black Rock Tavern or unwind at the casual atmosphere of The Acoustic Café. For live music and a lively crowd, check out The Fairfield Theatre Company.

*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, is perfect for a variety of vacations, whether you're seeking city vibes, outdoor adventures, or cultural experiences. Explore popular attractions like the beautiful beaches, urban parks, and modern universities that cater to families and culture enthusiasts alike. Don't forget to check out Fairfield beach hotels for a comfortable stay while you enjoy all that this charming town has to offer.

  • Jennings Beach: Enjoy the sun and sand at Jennings Beach, a local favorite for its relaxing beach vibes. This scenic spot is perfect for swimming, sunbathing, and picnicking, making it an ideal destination for families and friends looking to unwind by the water.
  • Bridgeport Downtown South Historic District: Immerse yourself in the rich culture of the Bridgeport Downtown South Historic District, located a mere 5 miles from Fairfield. Explore its charming streets, historic architecture, and vibrant local art scene, offering a glimpse into the area's storied past.
  • Total Mortgage Arena: Experience thrilling entertainment at Total Mortgage Arena, just 4 miles from Fairfield. This versatile venue hosts a variety of events, from concerts to sports, providing fun for the entire family and creating unforgettable memories.

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.

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.

Fairfield Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Westchester County Airport (HPN)
Population
59,100
Max Temp Winter
35ºF
Max Temp Summer
80ºF
Top Sights
Jennings Beach, Norwalk Maritime Aquarium and Compo Beach

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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 $445 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.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.