Book Holiday Homes in Glenwood

More Flash, Less Cash - Take advantage of our Price Pledge** (even on luxey stays)

We keep it easy with the option to pay now or later on select accommodation

Book up 'til the last second - millions of rooms to crash tonight^

Featured Holiday Homes in Glenwood

Greenwoods of Warwick

Greenwoods of Warwick

Monroe
With a stay at this vacation home in Monroe, you'll be within a 5-minute drive of Greenwood Lake and Sterling Forest State Park.
Greenwoods of Warwick
Mountain Creek Lovely 1 Bedroom/Pool/Jacuzzi/King Bed/Ski In/Out

Mountain Creek Lovely 1 Bedroom/Pool/Jacuzzi/King Bed/Ski In/Out

Vernon Township
The price is AU$526 per night from 27 Jan to 28 Jan
AU$526
includes taxes & fees
27 Jan - 28 Jan
With a stay at this vacation home in Vernon, you'll be in the mountains, within a 10-minute drive of Crystal Springs Golf Resort and Mountain Creek Ski ...
Mountain Creek Lovely 1 Bedroom/Pool/Jacuzzi/King Bed/Ski In/Out
Delightful Home w/ Fire Pit, Walk to Lake!

Delightful Home w/ Fire Pit, Walk to Lake!

Highland Lakes
With a stay at this vacation home in Highland Lakes, you'll be a 1-minute walk from Lake Wanda and 6 minutes by foot from Wawayanda State Park.
Delightful Home w/ Fire Pit, Walk to Lake!
Save an average of 15% on thousands of hotels when you're signed in
Work from home in paradise

Work from home in paradise

Andover
Located in Andover, this vacation home is a 5-minute drive from Bryant's Island and 5 minutes from Liffy Island.
Work from home in paradise
Red Cabin Lake House with Amazing Views!

Red Cabin Lake House with Amazing Views!

Vernon Township
With a stay at this vacation home in Vernon, you'll be on the waterfront, within a 10-minute drive of Crystal Springs Golf Resort and Bear Peak Express.
Red Cabin Lake House with Amazing Views!
BillyMoe’s Bungalow, A low key 3 Bedroom house with lake view.

BillyMoe’s Bungalow, A low key 3 Bedroom house with lake view.

Greenwood Lake
Located in Greenwood Lake, this vacation home is within a 5-minute drive of Greenwood Lake and Lion's Field Park.
BillyMoe’s Bungalow, A low key 3 Bedroom house with lake view.
Very Private Large Home on 22 Acres with Outdoor Kitchen

Very Private Large Home on 22 Acres with Outdoor Kitchen

Chester
With a stay at this vacation home in Chester, you'll be within a 10-minute drive of LEGOLAND® New York and Brotherhood Winery.
Very Private Large Home on 22 Acres with Outdoor Kitchen
Vernon Cozy 2BD Pet-Friendly Mountain Creek

Vernon Cozy 2BD Pet-Friendly Mountain Creek

Vernon Township
The price is AU$1,010 per night from 30 Jan to 31 Jan
AU$1,010
includes taxes & fees
30 Jan - 31 Jan
Located in Glenwood, this vacation home is a 5-minute drive from Wawayanda State Park and 9 minutes from Surface Ski Lift.
Vernon Cozy 2BD Pet-Friendly Mountain Creek
Experience luxury shopping paradise! 4-Bedroom Home & 7 mins to Woodbury Commons

Experience luxury shopping paradise! 4-Bedroom Home & 7 mins to Woodbury Commons

2 out of 5
Monroe
Located in Monroe, this vacation home is within a 15-minute drive of Woodbury Common Premium Outlets and LEGOLAND® New York.
Experience luxury shopping paradise! 4-Bedroom Home & 7 mins to Woodbury Commons
Don't see what you're looking for?
See all available properties in Glenwood
View all properties
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.

Glenwood Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Glenwood vacation homes are the perfect way for you to wing it.

Holiday houses in Glenwood let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Glenwood in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Glenwood adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Glenwood with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Glenwood vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Glenwood Holiday Homes essential information

Accommodation
157 Holiday Homes
Lowest Price
AU$144
Highest Price
AU$1,010
Popular accommodation
Greenwoods of Warwick, Mountain Creek Lovely 1 Bedroom/Pool/Jacuzzi/King Bed/Ski In/Out, Delightful Home w/ Fire Pit, Walk to Lake!, Work from home in paradise , Red Cabin Lake House with Amazing Views!, BillyMoe’s Bungalow, A low key 3 Bedroom house with lake view., Very Private Large Home on 22 Acres with Outdoor Kitchen , Vernon Cozy 2BD Pet-Friendly Mountain Creek, Experience luxury shopping paradise! 4-Bedroom Home & 7 mins to Woodbury Commons

Top trending hotels in Glenwood

Holiday Inn Express Hotel & Suites Chester, an IHG Hotel

Holiday Inn Express Hotel & Suites Chester, an IHG Hotel

2.5 out of 5
2 Bryle Place, Chester, NY
Fully refundable
The price is AU$144 per night from 26 Jan to 27 Jan
AU$144
includes taxes & fees
26 Jan - 27 Jan
Located in Chester, Holiday Inn Express Hotel & Suites Chester, an IHG Hotel is in the business district, within a 5-minute drive of Castle Fun Center and The ...
Holiday Inn Express Hotel & Suites Chester, an IHG Hotel
Sleep Inn & Suites Monroe - Woodbury

Sleep Inn & Suites Monroe - Woodbury

2.5 out of 5
1 Sleep Way, Monroe, NY
Fully refundableReserve now, pay when you stay
The price is AU$169 per night from 29 Jan to 30 Jan
AU$169
includes taxes & fees
29 Jan - 30 Jan
With a stay at Sleep Inn & Suites Monroe - Woodbury in Monroe, you'll be within a 10-minute drive of Woodbury Common Premium Outlets and LEGOLAND® New York.
Sleep Inn & Suites Monroe - Woodbury
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 AU$158 per night from 3 Feb to 4 Feb
AU$158
includes taxes & fees
3 Feb - 4 Feb
When you stay at Best Western Hunt's Landing Hotel Matamoras/Milford in Matamoras, you'll be in the historical district, within a 15-minute walk of Delaware ...
Best Western Hunt's Landing Hotel Matamoras/Milford
Save an average of 15% on thousands of hotels when you're signed in
Hampton Inn Harriman Woodbury

Hampton Inn Harriman Woodbury

2.5 out of 5
60 Centre Dr, Central Valley, NY
Fully refundableReserve now, pay when you stay
The price is AU$215 per night from 2 Feb to 3 Feb
AU$215
includes taxes & fees
2 Feb - 3 Feb
When you stay at Hampton Inn Harriman Woodbury in Central Valley, you'll be in a shopping district, within a 15-minute drive of Woodbury Common Premium Outlets ...
Hampton Inn Harriman Woodbury
Don't see what you're looking for?
See all available properties in Glenwood
View all properties
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.

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.