Fairfield County Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

Photo by Litchfield Hills Visitors Bureau

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to CA $1,096 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon

    Rest easy

    Plan, book, and manage your trip all in one place

Your Fairfield County Vacation

With a Fairfield County vacation package, you can forget about planning stresses and simply focus on experiencing all this exciting destination has to offer. With so much to do and see on a trip to Fairfield County, it can be tricky to know where to start. Kick off your travels in Stamford at Rye Playland and Norwalk Maritime Aquarium — two popular attractions here. Another top city to add to your itinerary is Shelton. Be sure not to miss Silver Sands State Park and Walnut Beach. Find some travel buddies and start packing, because your Fairfield County vacation is only a few clicks away with Expedia.

Top vacation destinations in Fairfield County

FlightsFlightsHotelsHotels

Stamford

Stamford

Top Fairfield County Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Hotel St. James

Hotel St. James

2.5 out of 5
Manhattan
Price was CA $1,290, price is now CA $816 per person
CA $816
per person
Nov 14 - Nov 17
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
8.8/10 Excellent! (6,263 reviews)
Very pleasant stay! We'd stay again.

Reviewed on Aug. 24, 2025

Outsite Chelsea

Outsite Chelsea

2 out of 5
Manhattan
Price was CA $1,710, price is now CA $1,017 per person
CA $1,017
per person
Oct 31 - Nov 3
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9.6/10 Exceptional! (10 reviews)
Nice stay. Very low bed and little room to get in and out. Great location. If booking through Expedia, be careful to check for shared/private bathroom as the description is misleading.

Reviewed on Aug. 22, 2025

The Shoreham Hotel

The Shoreham Hotel

4 out of 5
Manhattan
Price was CA $3,408, price is now CA $2,044 per person
CA $2,044
per person
Nov 7 - Nov 16
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
7.6/10 Good! (1,250 reviews)
Great hotel, conveniently located to metro and sites in Midtown Manhattan

Reviewed on Aug. 23, 2025

1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
Price was CA $2,776, price is now CA $1,669 per person
CA $1,669
per person
Oct 10 - Oct 12
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
8.8/10 Excellent! (1,009 reviews)
Wonderful room and staff. The Brooklyn Bridge view was amazing.

Reviewed on Aug. 21, 2025

The Fifth Avenue Hotel

The Fifth Avenue Hotel

5 out of 5
Manhattan
Price was CA $3,020, price is now CA $1,895 per person
CA $1,895
per person
Oct 2 - Oct 5
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9.6/10 Exceptional! (129 reviews)
Love the hotel especially the design and decor. Staff is so nice and professional. Room service food is excellent. The only negative is the lack of an in-house gym. Would stay again.

Reviewed on Aug. 22, 2025

Fairfield County Hotel Deals

Trumbull Marriott Shelton

Trumbull Marriott Shelton

3.5 out of 5
180 Hawley Ln, Trumbull, CT
Fully refundableReserve now, pay when you stay
The price is CA $199 per night from Sep 4 to Sep 5
CA $199
CA $229 total
Sep 4 - Sep 5
includes taxes & fees
8/10 Very Good! (1,004 reviews)
"Excellent stay."

Reviewed on Aug. 22, 2025

Trumbull Marriott Shelton
Amsterdam Hotel

Amsterdam Hotel

2 out of 5
19 Clarks Hill Ave, Stamford, CT
Fully refundableReserve now, pay when you stay
The price is CA $115 per night from Sep 8 to Sep 9
CA $115
CA $134 total
Sep 8 - Sep 9
includes taxes & fees
8.4/10 Very Good! (1,643 reviews)
"Hotel rooms are very big but outdated. Beds were comfortable atleast and close to freeway!"

Reviewed on Aug. 23, 2025

Amsterdam Hotel
Norwalk Inn & Conference Center

Norwalk Inn & Conference Center

4 out of 5
99 East Avenue, Norwalk, CT
Fully refundableReserve now, pay when you stay
The price is CA $158 per night from Sep 7 to Sep 8
CA $158
CA $182 total
Sep 7 - Sep 8
includes taxes & fees
8.6/10 Excellent! (1,290 reviews)
"Super nice hotel. The staff were friendly, the rooms were so clean, we would stay there again."

Reviewed on Aug. 22, 2025

Norwalk Inn & Conference Center
See all 817 properties in Fairfield County
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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Frequently asked questions

How much does a Fairfield County vacation package cost?
Explore the best of Fairfield County from just CA $816. Choose from a wonderful selection of flights, hotels and rental cars to suit your budget. Pick up even better deals when you add a couple of tours or activities to your package.
How do I get a cheap travel package to Fairfield County?
Bundle your bookings with Expedia to save big bucks on your next big adventure. With over 550 partner airlines and 1,000,000 hotels across the globe, your Fairfield County vacation package can be tailored exactly to suit your budget. With all that extra money, why not add one or two interesting tours and experiences? It's an easy way to unlock even more savings. Your dream vacation in Fairfield County is closer than you thought!
What are the top hotels in Fairfield County?
Check out The Stamford Hotel and Amsterdam Hotel. They're the first choice for many travelers headed to Stamford. If Norwalk is on your itinerary, Norwalk Inn & Conference Center and La Quinta Inn & Suites by Wyndham Stamford / New York City are both welcoming options.
How far in advance should I book my Fairfield County vacation?
Savvy travelers always book early. Airlines typically release flight tickets nearly 12 months prior to departure, and this is a perfect opportunity to land some of the lowest prices. Just been told you need to take your vacation time next month? That's alright! Expedia are never short of fantastic bargains to help you have the getaway of your dreams, at a price you can afford.
What does an Expedia Fairfield County travel package include?
It comes down to what you want. If you're traveling by yourself, you might decide to combine hotels and flights. Bringing the entire family to Fairfield County? A travel package including hotels, flights and rental cars might be a better fit. Expedia gives you the freedom and flexibility to customize your travel package.
What should I know before booking a Fairfield County travel package?
Our prices are already low. However, you'll score even more savings when you book your flights, hotels and car rentals together. With an Expedia package, you'll get transparent pricing and lots of choice.
Can I choose my airline with a Fairfield County Expedia vacation package?
Yes, so take your pick! We offer more than 550 airlines worldwide, so you can customize your Fairfield County vacation according to your budget and travel needs.
If I'm not able to travel, can I cancel my Fairfield County vacation package?
Don't worry if you're rethinking your Fairfield County vacation package — you can cancel or change your booking. And if you've booked it within the last 24 hours, you may be able to do it at no cost. However, bookings made more than 24 hours ago may incur fees from your airline, hotel or car rental company. We know life can throw the occasional spanner in the works, so head to our Customer Service Portal if that happens. When you're ready to make changes, we'll be here to help.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.