Glenwood Vacations from $573

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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.
The Wayne Inn

The Wayne Inn

2 out of 5
Save 100% on your flight
Price was $1,115, price is now $573 per person
$573
per person
Jul 17 - Jul 20
found 1 day ago
Roundtrip flight included
San Juan (SJU) to Newark Liberty Intl. Airport (EWR)
6.8/10 (289 reviews)
Clean room - hot shower -

Reviewed on May 5, 2026

Seven Beach Lane

Seven Beach Lane

2 out of 5
Price was $2,750, price is now $1,491 per person
$1,491
per person
Jul 21 - Jul 25
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Newark Liberty Intl. Airport (EWR)
10/10 Exceptional! (7 reviews)
Courteous and friendly staff

Reviewed on Nov 4, 2025

Placemakr Wall Street

Placemakr Wall Street

4 out of 5
Manhattan
Save 100% on your flight
Price was $4,922, price is now $2,824 per person
$2,824
per person
Jul 18 - Jul 25
found 22 hours ago
Roundtrip flight included
Atlanta (ATL) to Newark Liberty Intl. Airport (EWR)
9.2/10 Wonderful! (912 reviews)
The place was quite, staff was friendly. Clean and cozy rooms.

Reviewed on Apr 6, 2026

The Towers at Lotte New York Palace

The Towers at Lotte New York Palace

5 out of 5
Manhattan
Save 100% on your flight
Price was $2,469, price is now $1,435 per person
$1,435
per person
Jul 10 - Jul 13
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Newark Liberty Intl. Airport (EWR)
9.2/10 Wonderful! (666 reviews)
Customer Service is outstanding

Reviewed on Apr 23, 2026

Hotel Riu Plaza Manhattan Times Square

Hotel Riu Plaza Manhattan Times Square

4 out of 5
Manhattan
Save 100% on your flight
Price was $1,963, price is now $1,152 per person
$1,152
per person
Jul 16 - Jul 19
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Newark Liberty Intl. Airport (EWR)
9.2/10 Wonderful! (3,482 reviews)
Clean and excellent location and surprisingly quiet despite being so close to time square! Only issue is that communicating with the hotel beforehand is nearly impossible.

Reviewed on May 8, 2026

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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
$119 nightly
The price is $141 total per night from May 31 to Jun 1
$141 total
May 31 - Jun 1
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
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 13 to May 14
$130 total
May 13 - May 14
Total with taxes and fees
8.4/10 Very Good! (1,004 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
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
$106 nightly
The price is $116 total per night from May 26 to May 27
$116 total
May 26 - May 27
Total with taxes and fees
8.6/10 Excellent! (1,004 reviews)
We go for the hot breakfast

Reviewed on May 5, 2026

Best Western Hunt's Landing Hotel Matamoras/Milford
See all 626 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 from $573 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.