Sugar Loaf Vacations from $414

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to $1,045 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 Sugar Loaf Vacation

When a city break is calling your name, answer it with a vacation package to Sugar Loaf. With all your travel needs taken care of before you go, all you need to do here is focus on having the time of your life. You'll want to sightsee during your trip to Sugar Loaf. Carve out some time for big-name attractions such as The Rock Sports Complex, Castle Fun Center and Goosepond Mountain State Park. Expedia has what you need to escape your routine. Tailor your vacation to Sugar Loaf to suit your travel style, whatever that may be!

The Latest Sugar Loaf vacation packages

Price found within the past 48 hours. Click for updated prices.
Upstate Inn Monticello

Upstate Inn Monticello

3 out of 5
Price was $544, price is now $414 per person
$414
per person
Nov 13 - Nov 18
just found
Roundtrip flight included
San Juan (SJU) to Newburgh (SWF)
7/10 Good! (73 reviews)
Great Location. Room was absolutely immaculately clean. Comfy beds. Quiet and convenient location. Room was exactly as shown.Property is under going renovations.

Reviewed on Aug 23, 2025

YO1 Longevity & Health Resorts, Catskills

YO1 Longevity & Health Resorts, Catskills

4 out of 5
Save 100% on your flight
Price was $1,321, price is now $856 per person
$856
per person
Nov 13 - Nov 18
just found
Roundtrip flight included
San Juan (SJU) to Newburgh (SWF)
8/10 Very Good! (469 reviews)
Love the yoga love the room very clean pool and hot tub were amazing. Just wish they were open longer. Did not love the food.

Reviewed on Aug 23, 2025

Resorts World Catskills Casino

Resorts World Catskills Casino

4.5 out of 5
Save 100% on your flight
Price was $976, price is now $675 per person
$675
per person
Nov 13 - Nov 18
just found
Roundtrip flight included
San Juan (SJU) to Newburgh (SWF)
8.6/10 Excellent! (1,011 reviews)
Very clean , beautiful room

Reviewed on Aug 24, 2025

The Kartrite Resort & Indoor Waterpark

The Kartrite Resort & Indoor Waterpark

4 out of 5
Save 100% on your flight
Price was $580, price is now $420 per person
$420
per person
Oct 2 - Oct 6
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Newburgh (SWF)
8/10 Very Good! (1,657 reviews)
Staff and mananger was really friendy. Property was nice clean.

Reviewed on Aug 23, 2025

Courtyard by Marriott Newburgh Stewart Airport

Courtyard by Marriott Newburgh Stewart Airport

3 out of 5
Save 100% on your flight
Price was $659, price is now $501 per person
$501
per person
Oct 30 - Nov 4
found 2 hours ago
Roundtrip flight included
Atlanta (ATL) to Newburgh (SWF)
8.2/10 Very Good! (676 reviews)
The room and outdoor area was great The pool looks like it could use some updating. Had some friends visit and hung out in the garden area which was very nice as well. Fresh fruit and lemon water available daily in lobby.

Reviewed on Aug 15, 2025

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

Discover the most popular places to visit in Sugar Loaf

Castle Fun Center

You can take time to visit Castle Fun Center during your travels to Chester. While you're in the area, find time to visit its shops.

Castle Fun Center

The Rock Sports Complex

Explore the great outdoors at The Rock Sports Complex, a lovely green space in Chester. While you're in the area, find time to visit its shops.

The Rock Sports Complex

Museum Village

You can spend an afternoon exploring the galleries in Museum Village during your trip to Chester. While in this family-friendly area, find time to visit its shops.

Museum Village

Sugar Loaf Hotel Deals

The Crossroads Hotel, Newburgh

The Crossroads Hotel, Newburgh

3 out of 5
5 Lakeside Rd, Newburgh, NY
$109 nightly
The price is $129 total per night from Sep 2 to Sep 3
$129 total
Sep 2 - Sep 3
Total with taxes and fees
7.2/10 Good! (522 reviews)
"I enjoyed the location. The place was clean and employees were very pleasant"

Reviewed on Aug 21, 2025

The Crossroads Hotel, Newburgh
Overlook Lodge at Bear Mountain

Overlook Lodge at Bear Mountain

2.5 out of 5
55 Hessian Drive, Bear Mountain State Park, Bear Mountain, NY
Fully refundableReserve now, pay when you stay
$128 nightly
The price is $145 total per night from Aug 25 to Aug 26
$145 total
Aug 25 - Aug 26
Total with taxes and fees
8.2/10 Very Good! (1,001 reviews)
A cute bear themed hotel
"Overall our 2 nights stay at the hotel was good! It’s clean and comfortable. The lake was nice. The bear mt inn has multiple buildings around the lake. We got a room on 2Fl at the overlook lodge which was a bit far from the main building with no elevator. We didn’t bring a car so we had to walk back ..."

Reviewed on Aug 20, 2025

Overlook Lodge at Bear Mountain
Crowne Plaza Suffern - Mahwah by IHG

Crowne Plaza Suffern - Mahwah by IHG

3.5 out of 5
3 Executive Blvd, Suffern, NY
Fully refundable
$116 nightly
The price is $135 total per night from Sep 2 to Sep 3
$135 total
Sep 2 - Sep 3
Total with taxes and fees
8.8/10 Excellent! (1,003 reviews)
"Perfect"

Reviewed on Aug 20, 2025

Crowne Plaza Suffern - Mahwah by IHG
See all 698 properties in Sugar Loaf
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.

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 Sugar Loaf vacation package cost?
You'll find cheap prices from $414 on Expedia for your Sugar Loaf getaway. However, factors like your choice of hotel, the season and length of stay will influence how much your vacation to Sugar Loaf costs.
What are the cheapest months to go to Sugar Loaf?
October, November and December are the best times to search for cheap Sugar Loaf vacation packages. Choosing to travel in quieter months means you can generally find lower prices on flights and hotels.
How many days is enough for Sugar Loaf?
Usually, a handful of days is enough to visit the top sights during your Sugar Loaf vacation. But if you want to have some time to unwind or go on day tours, think about extending your trip.
How to find the best Sugar Loaf package deals?
Finding a cheap Sugar Loaf package deal is a cinch with Expedia. After you've entered your destination and preferred dates under our "Packages" tab, set your budget, apply a couple of filters and see what's available. You can tweak your search by "Property class," "Number of bedrooms," "Traveler experience" and more. Sort the results by "Price: low to high" to discover the most wallet-friendly Sugar Loaf package deals. Want a simple trick to score the biggest savings? Have some flexibility with your departure dates and consider traveling on a weekday, when prices are usually lower.
Is it cheaper to book a Sugar Loaf 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 usually snag a better deal than booking each component separately. And you'll still enjoy the freedom to create a customized Sugar Loaf vacation by choosing your preferred accommodation type, airline and car class.
When to book a vacation package to Sugar Loaf?
Land incredible discounts by reserving your flights ahead of time with Expedia. If spontaneity is more your style, take advantage of our last-minute deals for a spur-of-the-moment Sugar Loaf adventure.
Does Expedia offer Book Now, Pay Later Sugar Loaf vacation packages?
If you're like us, you love exploring new places but are not a fan of the price tag that can come with it. That's why we offer Book Now, Pay Later vacations. With the help of online lender Affirm, you can break down the total cost of your Sugar Loaf vacation over 3, 6 or 12 months. There are also no late payment fees or hidden costs, so you can snap up great vacation packages with payment plans as soon as you spot them.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.