Glenwood Vacations from $433

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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.

The Latest Glenwood vacation packages

Price found within the past 48 hours. Click for updated prices.
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Glenwood Hotel Deals

Sleep Inn & Suites Middletown - Goshen

Sleep Inn & Suites Middletown - Goshen

2.5 out of 5
3491 Route 6 Middletown NY
Fully refundable
$112 nightly
The price is $133 total per night from Jul 26 to Jul 27
$133 total
Jul 26 - Jul 27
Total with taxes and fees
8.8/10 Excellent! (1,049 reviews)
"I will never ever stay at this sleeps inn the house keeping service is horrible and the staff hang out at night with their friends. Also a couple of people were outside smoking pot"

Reviewed on Jul 2, 2026

Sleep Inn & Suites Middletown - Goshen
Best Western Hunt's Landing Hotel Matamoras/Milford

Best Western Hunt's Landing Hotel Matamoras/Milford

3 out of 5
120 Rtes 6 & 209 Matamoras PA
Fully refundableReserve now, pay when you stay
$118 nightly
The price is $128 total per night from Jul 5 to Jul 6
$128 total
Jul 5 - Jul 6
Total with taxes and fees
8.6/10 Excellent! (1,000 reviews)
"Room was comfortable for our one night stay. We are seniors and need more issues to be handled. Would have been nice to have a recliner in the room also a walk in shower."

Reviewed on Jun 30, 2026

Best Western Hunt's Landing Hotel Matamoras/Milford
La Quinta Inn & Suites by Wyndham Middletown-Goshen

La Quinta Inn & Suites by Wyndham Middletown-Goshen

3 out of 5
551 Route 211 E Middletown NY
Fully refundableReserve now, pay when you stay
$123 nightly
The price is $146 total per night from Jul 26 to Jul 27
$146 total
Jul 26 - Jul 27
Total with taxes and fees
9.4/10 Exceptional! (1,001 reviews)
"Rooms were clean and A/C worked well. Lots of water pressure in the shower. Friendly staff."

Reviewed on Jul 2, 2026

La Quinta Inn & Suites by Wyndham Middletown-Goshen
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 from $433 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.