Caldwell Vacations from $567

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to $2,000 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 Caldwell Vacation

With plenty of highlights as well as some hidden gems, this city is best experienced with a Caldwell vacation package. Look for places to stay in Newark Central Business District, which is good for shopping, nightlife and history. Like to explore your surroundings? Livingston Mall, Jumpnasium Kids Parties & More and Monster Mini Golf are among the most popular places to visit during your trip to Caldwell. Whoever you're heading away with and whatever your bank balance, your ultimate Caldwell vacation is just clicks away with Expedia.

The Latest Caldwell vacation packages

Price found within the past 48 hours. Click for updated prices.
Windrose On Hudson

Windrose On Hudson

3 out of 5
Save 100% on your flight
Price was $848, price is now $567 per person
$567
per person
Jun 19 - Jun 23
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Newark Liberty Intl. Airport (EWR)
8.4/10 Very Good! (133 reviews)
It’s a beautiful setting, our room was clean, quiet and spacious. The staff quickly dealt with a very minor key issue, everyone was friendly. We will absolutely stay again when return to visit Family in Ossining.

Reviewed on May 10, 2026

Paradise Stream Resort

Paradise Stream Resort

3.5 out of 5
Save 100% on your flight
Price was $1,967, price is now $1,330 per person
$1,330
per person
Aug 3 - Aug 10
found 1 day ago
Roundtrip flight included
San Juan (SJU) to Newark Liberty Intl. Airport (EWR)
8/10 Very Good! (1,102 reviews)
Clean and beautiful!! Fireplace log lasted longer than expected! Hot tub was great!!

Reviewed on May 11, 2026

Casa Francesca 6BR Villa & Heated Pool

Casa Francesca 6BR Villa & Heated Pool

3.5 out of 5
Save 100% on your flight
Price was $4,038, price is now $2,735 per person
$2,735
per person
Jun 14 - Jun 19
found 7 hours ago
Roundtrip flight included
Atlanta (ATL) to Newark Liberty Intl. Airport (EWR)
No reviews
Dome House Retreat

Dome House Retreat

4.5 out of 5
Save 100% on your flight
Price was $2,522, price is now $1,725 per person
$1,725
per person
Jun 14 - Jun 19
found 24 hours ago
Roundtrip flight included
Atlanta (ATL) to Newark Liberty Intl. Airport (EWR)
No reviews
Echo Valley Cottages

Echo Valley Cottages

3 out of 5
Save 100% on your flight
Price was $1,258, price is now $861 per person
$861
per person
Aug 3 - Aug 10
found 1 day ago
Roundtrip flight included
San Juan (SJU) to Newark Liberty Intl. Airport (EWR)
8.6/10 Excellent! (60 reviews)
The cottage was very clean and decorated festivity. Communication was great. I worked like to go back for another visit

Reviewed on Jan 9, 2026

Don't see what you're looking for?
See all available trips from Columbus to Caldwell
View all trips

Caldwell Hotel Deals

Hyatt Grand Central New York

Hyatt Grand Central New York

4 out of 5
109 East 42nd Street New York NY
Fully refundableReserve now, pay when you stay
$239 nightly
The price is $278 total per night from May 25 to May 26
$278 total
May 25 - May 26
Total with taxes and fees
8.4/10 Very Good! (6,909 reviews)
The moment I walked in staff informed me that they never offered valet services, and two minutes later a valet showed up. Our room smelled like mold and the bathroom had a strong urine odor. Ohhh not to mention the clogged tub! We had a terrible experience at the Hyatt Hotel.

Reviewed on May 15, 2026

Hyatt Grand Central New York
Sheraton New York Times Square Hotel

Sheraton New York Times Square Hotel

4 out of 5
811 7th Ave New York NY
Fully refundableReserve now, pay when you stay
$194 nightly
The price is $226 total per night from May 25 to May 26
$226 total
May 25 - May 26
Total with taxes and fees
7.4/10 Good! (7,938 reviews)
The hotel is in a perfect spot in the city

Reviewed on May 15, 2026

Sheraton New York Times Square Hotel
NEW YORKER BY LOTTE HOTELS

NEW YORKER BY LOTTE HOTELS

4 out of 5
481 Eighth Ave. New York NY
Fully refundableReserve now, pay when you stay
$189 nightly
The price is $220 total per night from May 25 to May 26
$220 total
May 25 - May 26
Total with taxes and fees
8.2/10 Very Good! (6,735 reviews)
Just a very old run down hotel

Reviewed on May 15, 2026

NEW YORKER BY LOTTE HOTELS
See all 11,220 properties in Caldwell
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 Caldwell Vacation Packages

Caldwell Essential Information

Language
English
Currency
U.S dollars
Closest Airport
John F. Kennedy Intl. Airport (JFK)
Population
7,900
Max Temp Winter
35ºF
Max Temp Summer
80ºF
Top Sights
Cricket Hill Brewing Co, Funtime Junction and Grover Cleveland Birthplace

More vacations you might like

All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Frequently asked questions

How much does a Caldwell vacation package cost?
You'll find cheap prices from $567 on Expedia for your Caldwell break. However, factors like the length of stay, hotel choice and season will influence how much your vacation to Caldwell costs.
What are the cheapest months to go to Caldwell?
December, January and February are the best times to look for cheap Caldwell vacation packages. Choosing to travel in quieter months means you can usually find reduced prices on accommodations and flights.
How many days is enough for Caldwell?
With a well-planned itinerary, you can easily tick off the top Caldwell attractions in a few days. But if you prefer to discover hidden gems or go on day tours, think about booking your Caldwell vacation for longer.
How to find the best Caldwell package deals?
Use Expedia's filters to find some of the best Caldwell package deals. When you begin your search, just set your maximum budget and then order the results by "Price: low to high." If you want to save, plan your trip for midweek, or browse for Caldwell package deals in the off-season. Switch up your travel dates and you may land even better discounts. As a rule of thumb, it's usually best to lock in your vacation package well in advance.
Is it cheaper to book a Caldwell vacation as a package?
An Expedia vacation package could land you significant savings when compared to arranging flights and hotels separately. Better still, you can personalize your Caldwell escape to match your exact needs. Pick your preferred flight time, select the hotel type and add a car rental. Browse our bundle deals and find out how much you can save.
When to book a vacation package to Caldwell?
Land incredible bargains by booking your flights early with Expedia. If spontaneity is more your style, take advantage of our last-minute deals for a spur-of-the-moment Caldwell vacation.
Does Expedia offer Book Now, Pay Later Caldwell vacation packages?
Set off on your ideal getaway to Caldwell with Expedia's Book Now, Pay Later vacations. No need to scrimp and save or wait for your next paycheck — we've joined forces with online lender Affirm to offer you flexibility with your finances. Our vacation packages with payment plans allow you to spread the total cost across 3, 6 or 12 months. With no late payment fees or hidden charges, you can easily budget for your trip and snap up bargains before they disappear.

Explore a world of travel with Expedia

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