Sugar Loaf Vacations

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Find the Best Sugar Loaf Vacation Packages

Sugar Loaf Hotel Deals

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
The price is AED 428 per night from Apr 22 to Apr 23
AED 428
AED 485 total
includes taxes & fees
22 Apr - 23 Apr
8.2/10 Very Good! (1,007 reviews)
"It was great experience. Felt like I was out of NY (the city that is), which was great. Very peaceful atmosphere. Beautiful views. The Outlook Lodge is a little more than a mile walk to the main Inn which is the Bear Mountain Inn. Sometimes it’s difficult going to and fro if you don’t have a car. ..."

Reviewed on 19 April 2025

Overlook Lodge at Bear Mountain
La Quinta Inn & Suites by Wyndham Middletown
La Quinta Inn & Suites by Wyndham Middletown
2.5 out of 5
551 Route 211 E, Middletown, NY
Fully refundableReserve now, pay when you stay
The price is AED 465 per night from May 1 to May 2
AED 465
AED 550 total
includes taxes & fees
1 May - 2 May
9.2/10 Wonderful! (676 reviews)
"Very clean, staffs were pleasant, Decent breakfast and coffee Starbucks and Buffalo Wild Wings within walking distance 10min from Legoland Pool amd jacuzzi were nice We had a great time!"

Reviewed on 18 April 2025

La Quinta Inn & Suites by Wyndham Middletown
Sleep Inn & Suites Middletown - Goshen
Sleep Inn & Suites Middletown - Goshen
2.5 out of 5
3491 Route 6, Middletown, NY
Fully refundableReserve now, pay when you stay
The price is AED 455 per night from May 4 to May 5
AED 455
AED 538 total
includes taxes & fees
4 May - 5 May
8.6/10 Excellent! (1,016 reviews)
"Conveniently located, clean"

Reviewed on 17 April 2025

Sleep Inn & Suites Middletown - Goshen
See all 691 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.

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?
Plan your trip for the low season and you’re likely to find cheap Sugar Loaf vacation packages. Bear in mind that public holidays and major local events can impact prices, so do a little research before you go.
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.
How to plan a trip to Sugar Loaf?

  1. Pick the perfect time to travel: Your schedule, preferred season and the type of weather you like can all influence your decision on when to travel to Sugar Loaf.
  2. Set your budget: Factor in costs like food, flights and transportation when calculating how much to set aside for your trip to Sugar Loaf. Then, select a hotel that matches your budget, whether that’s an affordable stay or a lavish retreat.
  3. Decide your trip length: Consider how much time you want to spend discovering Sugar Loaf. Plan your days so you can get to all the activities and attractions you’re interested in at a comfortable pace.
  4. Bundle your bookings: With your travel dates in place, you can combine your hotels, flights, car rental and more into a customized Sugar Loaf vacation package.

Discover the most popular places to visit in Sugar Loaf

The Rock Sports Complex

4/5(4 reviews)

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

4/5(7 reviews)

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

5/5(1 review)

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