Glenwood Vacation Packages

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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.

Top Glenwood Vacation Deals

Price found within the past 48 hours. Click for updated prices.
The Ridge Hotel

The Ridge Hotel

3 out of 5
Manhattan
Price was CA $1,445, price is now CA $1,053 per person
CA $1,053
per person
Aug 21 - Aug 26
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Newark Liberty Intl. Airport (EWR)
8.2/10 Very good! (1,156 reviews)
I was able to check in a bit early and the person at the front desk was very helpful. While I waited I asked for a place to work and I was sent to the basement to wait, which was a very uninviting space. Once I was able to get into my room it was clean, but located on the first floor right off the lobby. I really only got to sleep in the hotel and when I got there later that night - being off the lobby was very loud. The door from the lobby to the hallway of rooms was slamming shut often and it was very disturbing. All I did was sleep there, but that first room was not a very comfortable place to sleep.

Reviewed on Jul 8, 2026

Hotel Riu Plaza New York Times Square

Hotel Riu Plaza New York Times Square

4 out of 5
Manhattan
Price was CA $1,942, price is now CA $1,254 per person
CA $1,254
per person
Aug 21 - Aug 25
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Newark Liberty Intl. Airport (EWR)
9/10 Wonderful! (3,130 reviews)
La mejor ubicación, desayuno, servicio y comodidades

Reviewed on Jul 8, 2026

Hotel Riu Plaza Manhattan Times Square

Hotel Riu Plaza Manhattan Times Square

4 out of 5
Manhattan
Price was CA $1,665, price is now CA $1,096 per person
CA $1,096
per person
Aug 7 - Aug 10
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Newark Liberty Intl. Airport (EWR)
9.2/10 Wonderful! (3,652 reviews)
great location. clean room. If there's a microwave it would be even better

Reviewed on Jul 8, 2026

Candlewood Suites New York City-Times Square by IHG

Candlewood Suites New York City-Times Square by IHG

2.5 out of 5
Manhattan
Price was CA $2,079, price is now CA $1,422 per person
CA $1,422
per person
Sep 27 - Oct 2
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Newark Liberty Intl. Airport (EWR)
8.6/10 Excellent! (2,026 reviews)
Love the kitchen. A plus in New York city. Dislike the carpet at the reception area. Very dirty..I couldn't seat arround. Comfy beds.

Reviewed on Jul 8, 2026

INNSiDE by Meliá New York Nomad

INNSiDE by Meliá New York Nomad

4.5 out of 5
Manhattan
Price was CA $1,511, price is now CA $1,087 per person
CA $1,087
per person
Aug 21 - Aug 25
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Newark Liberty Intl. Airport (EWR)
9.2/10 Wonderful! (2,253 reviews)
What a dream hotel this is. For the area the rooms are so clean, spacious and comfortable. The hotel staff are friendly and professional. The on site restaurant is very good if you don’t want to go out. Thoroughly recommend to anyone.

Reviewed on Jul 7, 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
The price is CA $158 per night from Jul 29 to Jul 30
CA $158
CA $187 total
Jul 29 - Jul 30
includes taxes & fees
8.8/10 Excellent! (1,071 reviews)
"The woman at the front desk was incredibly friendly, polite and helpful. I was sad to see that she appears to be so short staffed that I saw her trying to manage different areas at different times. The room was clean and comfortable. The pool was a bit ‘cloudy’ so maybe increasing the frequency of ..."

Reviewed on Jul 8, 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
The price is CA $156 per night from Jul 26 to Jul 27
CA $156
CA $170 total
Jul 26 - Jul 27
includes taxes & fees
8.6/10 Excellent! (1,010 reviews)
"1. Ordered 2 things from off the menu from the restaurant. They got the order wrong. 2. Checked in. Received room key. Room was dirty and beds not made up. 3. Received a key card for a new room. Card did not open door to the room."

Reviewed on Jul 6, 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
The price is CA $175 per night from Jul 26 to Jul 27
CA $175
CA $207 total
Jul 26 - Jul 27
includes taxes & fees
9.4/10 Exceptional! (1,007 reviews)
"the breakfast was great the staff is wonderful the rooms are nice and clean stay here all the time when we go to middle town even my fur baby loves then the pool and hot tub are nice and clean excellent hotel."

Reviewed on Jul 7, 2026

La Quinta Inn & Suites by Wyndham Middletown-Goshen
See all 629 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.
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Frequently asked questions

How much does a Glenwood vacation package cost?
Offering excellent value package deals from CA $1,053 on Expedia, you'll be thrilled with how little a vacation to Glenwood costs! Our packages make travel planning easier and your savings go further.
What are the cheapest months to go to Glenwood?
January, February and March are the best times to look for cheap Glenwood vacation packages. Travelling in less busy months means you'll typically find lower prices on flights and accommodations.
How many days is enough for Glenwood?
Dedicate around 2 days for your Glenwood vacation in order to take in all that makes this place special. Stroll around popular areas, including Vernon Valley and New Milford. Then tick off major sights like Wawayanda State Park and Highland Lakes Beach 7. With a clever itinerary, you can keep busy with room for some rest time too. Want to venture outside of Glenwood? Consider squeezing in a day trip or two.
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 apply a few filters, like "Property type" and "Popular locations," to fine-tune the results to your exact needs. You can also sort by "Package discount" and discover offers that come with big savings. If you don't find the ideal Glenwood package deal right away, just change your dates and search again. Bear in mind that deals are only available for a limited time, so book early and get your Glenwood getaway off to a flying start.
Is it cheaper to book a Glenwood vacation as a package?
Expedia vacation packages are designed to make your money go further. Bundle your car rental, flight and hotel into one great-value price and enjoy significant savings. You'll generally score a better deal than booking each component separately. And you'll still get the flexibility to create a customized Glenwood vacation by choosing your preferred type of stay, airline and car class.
When to book a vacation package to Glenwood?
If you're considering a spur-of-the-moment Glenwood adventure, check out our last-minute deals that can be booked up to a week before you take off. Don't want to leave things to the last minute? You can score awesome deals on your hotels and flights by booking ahead.
How to plan a trip to Glenwood?

  1. Choose when to go: Check your calendar and get your bags packed. Your favourite season and the type of activities on offer will also help you decide when to escape to Glenwood.
  2. Set your budget: Factor in costs like flights, meals and transportation when calculating how much to put aside for your trip to Glenwood. Then, select a hotel that suits your budget, whether that's an affordable option or a swankier getaway.
  3. Decide how long to go away for: Now that you're more familiar with Glenwood, you can figure out the ideal length of your vacation. Pull together a draft itinerary and allocate enough time for all the things you want to do.
  4. Combine your accommodations and airfare: After you've nailed down your trip dates and duration, lock in the right Glenwood vacation package for you.

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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.