New Fairfield Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*

  • Find the right fit

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

  • Rest easy

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

Your New Fairfield Vacation

When you choose a New Fairfield vacation package, you can really enjoy your escape to the fullest. Uncover the sights and sounds of this exciting city knowing that all the travel planning has been taken care of in advance. If a sightseeing tour is on the agenda during your trip to New Fairfield, look around popular attractions like Candlewood Lake, Danbury Fair Mall and Danbury Ice Arena. Check out Expedia's wide range of travel options and begin planning your dream vacation to New Fairfield now.

Top New Fairfield Vacation Deals

Price found within the past 48 hours. Click for updated prices.
JW Marriott Essex House New York

JW Marriott Essex House New York

4.5 out of 5
Manhattan
Price was CA $1,692, price is now CA $984 per person
CA $984
per person
Jan 13 - Jan 16
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
8.8/10 Excellent! (1,001 reviews)

The St. Regis New York

The St. Regis New York

5 out of 5
Manhattan
Save 100% on your flight
Price was CA $8,770, price is now CA $4,580 per person
CA $4,580
per person
Jan 23 - Jan 30
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to New York (JFK)
9.2/10 Wonderful! (293 reviews)
The managers need complete retraining or higher managers that are way more capable in dealing with customers and not fighting and arguing with them and telling them they’re wrong

Reviewed on Nov 6, 2026

The Langham, New York, Fifth Avenue

The Langham, New York, Fifth Avenue

5 out of 5
Manhattan
Price was CA $3,716, price is now CA $2,105 per person
CA $2,105
per person
Feb 4 - Feb 7
found 7 hours ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9.6/10 Exceptional! (1,006 reviews)

Eurostars The Chemists’ Club Hotel

Eurostars The Chemists’ Club Hotel

4 out of 5
Manhattan
Price was CA $2,329, price is now CA $1,362 per person
CA $1,362
per person
Dec 21 - Dec 24
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9.4/10 Exceptional! (555 reviews)
Noise in my room and toilet didn’t work

Reviewed on Nov 11, 2026

Loews Regency New York Hotel

Loews Regency New York Hotel

5 out of 5
Manhattan
Price was CA $3,057, price is now CA $1,864 per person
CA $1,864
per person
Jan 22 - Jan 27
found 3 hours ago
Roundtrip flight included
Toronto (YYZ) to New York (JFK)
9.2/10 Wonderful! (1,002 reviews)
Our servis was excellent. Maria is the best staff, so helpfully and really nice so I could take she with me home 😊

Reviewed on Nov 11, 2026

Ready to book your vacation to New Fairfield?

 

Choose your dates

New Fairfield Hotel Deals

Escape to a Luxury Lakehouse Retreat- Chefs Indoor Outdoor Kitchen Hot Tub Steam

Escape to a Luxury Lakehouse Retreat- Chefs Indoor Outdoor Kitchen Hot Tub Steam

New Fairfield CT
9.8/10 Exceptional! (20 reviews)
"This house does not disappoint…. If you’re on the fence just rent it - you won’t regret it. We were a group of 8 adults. The weather was perfect for fall and we enjoyed the pizza oven, the outside ping pong table, the several decks and the hot tub. It was big enough that we never felt on top of each ..."

Reviewed on Oct 28, 2026

Get rates
Escape to a Luxury Lakehouse Retreat- Chefs Indoor Outdoor Kitchen Hot Tub Steam
Worth Every Step to Lake's Edge Direct Lakefront-Private Docks, Fire Pit, EV Chg

Worth Every Step to Lake's Edge Direct Lakefront-Private Docks, Fire Pit, EV Chg

New Fairfield CT
9.8/10 Exceptional! (44 reviews)
"Property is great!"

Reviewed on Sep 21, 2026

Get rates
Worth Every Step to Lake's Edge Direct Lakefront-Private Docks, Fire Pit, EV Chg
Lakehouse Boat Dock, Kayaks, Fire-Pit, Pool Table, Air Hockey, Hammock, King Bed

Lakehouse Boat Dock, Kayaks, Fire-Pit, Pool Table, Air Hockey, Hammock, King Bed

New Fairfield CT
9/10 Wonderful! (62 reviews)
"The house was clean and cozy! Loved the views. Check-in was smooth and easy. Would definitely stay again."

Reviewed on Oct 21, 2026

Get rates
Lakehouse Boat Dock, Kayaks, Fire-Pit, Pool Table, Air Hockey, Hammock, King Bed
See all 672 properties in New 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Stay near popular New Fairfield attractions

Squantz Pond State Park

You can take time to visit Squantz Pond State Park during your travels to New Fairfield. Savor the top-notch restaurants and charming coffeehouses while in town.
See properties

Frequently asked questions

How much does a New Fairfield vacation package cost?
You can grab a vacation package to this destination from CA $984 on Expedia. But how much your vacation to New Fairfield costs will depend on factors like your hotel choice, length of stay and season.
What are the cheapest months to go to New Fairfield?
The off-season is the best time to travel to New Fairfield if you're hoping to keep costs down. Another tip for scoring cheap New Fairfield vacation packages? Avoid visiting during public holidays and any major festivals or events.
How many days is enough for New Fairfield?
The ideal length for your New Fairfield vacation depends on what you'd like to see and do. Generally, a few days to a week will give you enough time to tick off all the leading sights and explore some hidden gems along the way.
How to find the best New Fairfield package deals?
Use Expedia's handy filters to help you find some terrific New Fairfield package deals. When you start your search, simply set your maximum budget and then sort the results by "Price: low to high." If you want to save, plan your adventure for midweek, or look for New Fairfield package deals in the low season. Play around with your travel dates and you may land even bigger discounts. As a rule of thumb, it's typically best to lock in your vacation package as soon as possible.
Is it cheaper to book a New Fairfield vacation as a package?
Expedia vacation packages are designed to help you keep more money in your pocket. Bundle your hotel, car rental and flight into one great-value price and enjoy significant savings. You'll typically get a better deal than booking each component separately. And you'll still have the flexibility to create a tailored New Fairfield vacation by choosing your favourite accommodation type, airline and car class.
When to book a vacation package to New Fairfield?
If you have your New Fairfield travel dates confirmed, book as early as you can to grab some incredible deals. With Expedia, you can generally reserve some flights up to one year ahead of time. Prefer spur-of-the-moment getaways? Our last-minute deals are great for travelling on a whim.
How to plan a trip to New Fairfield?

  1. Choose your travel dates: What you want to do in New Fairfield and your preferred season will help you decide when to get away.
  2. Budget wisely: On top of the price of your stay, you should factor in other expenses. These include food, flights and transportation. Also, set aside some extra funds for unexpected costs that may crop up during your trip to New Fairfield.
  3. Determine how many days away: Start by compiling a list of the attractions and activities you'd like to get to in New Fairfield. Then, estimate how long you'll need for each, along with any travel time.
  4. Bundle your hotel and flights: Awesome destination, check. Length of stay, check. Now all that's left is to choose a New Fairfield vacation package that brings all your bookings together.

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