Sugar Loaf Vacations

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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!

Discover the most popular places to visit in Sugar Loaf

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

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

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

Sleep Inn & Suites Middletown - Goshen

Sleep Inn & Suites Middletown - Goshen

2.5 out of 5
3491 Route 6 Middletown NY
Fully refundable
$117 nightly
The price is $138 total per night from Jun 9 to Jun 10
$138 total
Jun 9 - Jun 10
Total with taxes and fees
8.8/10 Excellent! (1,021 reviews)
Staff was not very professional, guests were playing music in the hallways at 1am and yelling loudly from room to room. Room was decent, however pillows were very thin and small.

Reviewed on May 8, 2026

Sleep Inn & Suites Middletown - Goshen
Overlook Lodge at Bear Mountain

Overlook Lodge at Bear Mountain

2.5 out of 5
55 Hessian Drive Bear Mountain NY
$122 nightly
The price is $150 total per night from May 11 to May 12
$150 total
May 11 - May 12
Total with taxes and fees
8.4/10 Very Good! (1,009 reviews)
The lodge needs a lot of upgrades.

Reviewed on May 7, 2026

Overlook Lodge at Bear Mountain
Courtyard by Marriott Middletown Goshen

Courtyard by Marriott Middletown Goshen

3 out of 5
24 Crystal Run Xing Middletown NY
Fully refundableReserve now, pay when you stay
$110 nightly
The price is $130 total per night from May 26 to May 27
$130 total
May 26 - May 27
Total with taxes and fees
8.4/10 Very Good! (1,005 reviews)
Courtyard Marriott is a great place to stay! Roomy rooms, clean, quiet. The website lists a restaurant, but it is more like a deli-take out restaurant. Breakfast is à la carte.

Reviewed on Apr 30, 2026

Courtyard by Marriott Middletown Goshen
See all 770 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.

Find the Best Sugar Loaf Vacation Packages

Sugar Loaf Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Stewart Intl. Airport (SWF)
Max Temp Winter
35ºF
Max Temp Summer
80ºF
Top Sights
Castle Fun Center, Goosepond Mountain State Park and The Rock Sports Complex

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Frequently asked questions

How much does a Sugar Loaf vacation package cost?
You'll find cheap prices 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.