Glenwood Vacations

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Your Glenwood Vacation

Unforgettable adventures await when you book a vacation package to Glenwood. Whether you're a foodie, history buff or just a traveler who loves to discover new places, there's something for everyone in this interesting city. If your trip to Glenwood includes some sightseeing, hit up popular attractions like Mountain Creek Ski Resort, Mountain Creek Waterpark and Warwick Valley Winery and Distillery. Don't put off exploring this city any longer. The perfect Glenwood vacation is just a few clicks away with Expedia.

Glenwood Hotel Deals

Sleep Inn & Suites Middletown - Goshen

3491 Route 6 Middletown NY

Fully refundable

$106 nightly

$126 total

Sep 8 - Sep 9

Total with taxes and fees

La Quinta Inn & Suites by Wyndham Middletown-Goshen

551 Route 211 E Middletown NY

Fully refundableReserve now, pay when you stay

$126 nightly

$149 total

Aug 23 - Aug 24

Total with taxes and fees

9.4/10 Exceptional! (1,005 reviews)

"Not my first time staying at La Quinta. The room was filthy and the mattress was dirty. Customer service was great. Housekeeping needs to do better and please get some new mattresses. It used to be a very nice hotel."

Reviewed on Aug 17, 2026

LEGOLAND Hotel NEW York

1 LEGOLAND BLVD Goshen NY

$312 nightly

$368 total

Sep 7 - Sep 8

Total with taxes and fees

8.4/10 Very Good! (95 reviews)

"Great stay with my family of 5 ! Kids had blast! One night stand , overall great experience! Thanks Legoland New York!"

Reviewed on Aug 16, 2026

See all 633 properties in Glenwood

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 Glenwood Vacation Packages

Glenwood Essential Information

Language	English
Currency	U.S dollars
Closest Airport	Stewart Intl. Airport (SWF)
Top Sights	Mountain Creek Waterpark, Mountain Creek Ski Resort and High Point State Park

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Frequently asked questions

How much does a Glenwood vacation package cost?

You can grab a vacation package to this top destination on Expedia. However, how much your vacation to Glenwood costs will depend on factors like your hotel choice, length of stay and season.

What are the cheapest months to go to Glenwood?

If you're hoping to snag a cheap Glenwood vacation package, consider visiting in December, January and February. You'll typically find lower rates on hotels and airfares during these quieter months — perfect for budget-conscious travelers.

How many days is enough for Glenwood?

Usually, a handful of days is enough to see the major sights during your Glenwood vacation. However, if you'd like to have time to chill out or take day tours, think about extending your trip.

How to find the best Glenwood package deals?

Start your search for a Glenwood package deal by entering your preferred trip dates and destination under our "Packages" tab. Then add some filters, like "Guest rating" and "Property type," to fine-tune the results to your exact needs. You can also sort by "Package discount" and browse offers that come with big savings. If you don't find the perfect Glenwood package deal straight away, simply switch up your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your Glenwood escape underway.

Is it cheaper to book a Glenwood vacation as a package?

An Expedia vacation package could score you significant savings when compared to booking accommodations and flights individually. Better still, you can customize your Glenwood trip to match your exact style. Pick your preferred flight time, select the hotel type and add a rental car. Browse our great deals to see how much you can save.

When to book a vacation package to Glenwood?

If you're planning an impromptu Glenwood adventure, browse our last-minute deals that can be booked up to one week before you go. Prefer not to wait until the last minute? You can score incredible deals on your flights and hotels by booking well in advance.

Does Expedia offer Book Now, Pay Later Glenwood vacation packages?

Your Glenwood trip is meant to be a relaxing escape from your daily routine, not a source of money-related stress. So to give you more flexibility, we've joined up with online lender Affirm to bring you our Book Now, Pay Later vacations. Pick one of our vacation packages with payment plans and break down the total cost over 3, 6 or 12 months. Plus, there aren't any hidden costs or late payment fees to worry about.

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

Glenwood Vacations

Book a Hotel + Flight or Car together to unlock savings

Room 1

Plan, book, travel with confidence

Better together

Find the right fit

Rest easy

Your Glenwood Vacation

Glenwood Hotel Deals

Sleep Inn & Suites Middletown - Goshen

La Quinta Inn & Suites by Wyndham Middletown-Goshen

LEGOLAND Hotel NEW York

Find the Best Glenwood Vacation Packages

Glenwood Essential Information

More vacations you might like

Frequently asked questions

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