Glenwood Vacation Rentals

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Check prices for these dates

In two weeks
Jan 16 - Jan 18
In two months
Feb 27 - Mar 1
In three months
Mar 27 - Mar 29
In four months
Apr 24 - Apr 26

Our top choices for Glenwood vacation rentals

Deluxe Cabin, Garden View | Free WiFi
Forava Cabins - Tiny Cabin in the Woods

Cabin in Ringwood

Forava Cabins - Tiny Cabin in the Woods
3.0 star property
10.0 out of 10, Exceptional, (1)
"Very cute, well decorated, quiet, and has everything we needed for a get away."
United States
Alexis
$215 nightly
The price is $241
Jan 8 - Jan 9
Total with taxes and fees
Forava Cabins - Tiny Cabin in the Woods
Children's area
Relaxing Farm Cottage Escape, 10 Min from LEGOLAND

Cottage in Goshen

Relaxing Farm Cottage Escape, 10 Min from LEGOLAND
9.8 out of 10, Exceptional, (12)
"Beautiful location. We really enjoyed seeing the deer in the field every morning. "
United States
Aaron M.
$280 nightly
The price is $292
Jan 4 - Jan 5
Total with taxes and fees
Relaxing Farm Cottage Escape, 10 Min from LEGOLAND
Interior
Room 1 at The Warwick Inn – Cozy Elegance in the Heart of Town

Vacation Home in Warwick

Room 1 at The Warwick Inn – Cozy Elegance in the Heart of Town
9.4 out of 10, Exceptional, (8)
"I really enjoyed my stay. The room was very clean, the inn is well located in town and it is great having the restaurant below. Would stay here again! "
United States
Erin R.
$131 nightly
The price is $148
Jan 27 - Jan 28
Total with taxes and fees
Room 1 at The Warwick Inn – Cozy Elegance in the Heart of Town
Interior
Villa Verde B&B, bsm, Greenwood Lake NY

Aparthotel in Greenwood Lake

Villa Verde B&B, bsm, Greenwood Lake NY
10.0 out of 10, Exceptional, (12)
"The breakfast was lovely!"
United States
Tara
$256 nightly
The price is $290
Jan 4 - Jan 5
Total with taxes and fees
Villa Verde B&B, bsm, Greenwood Lake NY
Property grounds
Serene lakeside oasis - fast WiFi 1.5 hrs from NYC, fire-pit & nature all around

Cottage in Sparrow Bush

Serene lakeside oasis - fast WiFi 1.5 hrs from NYC, fire-pit & nature all around
9.4 out of 10, Exceptional, (11)
"A little off the beaten path, but a lovely Vrbo with excellent amenities with a nice natural surrounding."
United States
Nicholas G.
$245 nightly
The price is $277
Jan 4 - Jan 5
Total with taxes and fees
Serene lakeside oasis - fast WiFi 1.5 hrs from NYC, fire-pit & nature all around
Property grounds
Cozy 1-bedroom condo-Ski in/out/Waterpark/King Bed/WIFI/Parking

Condo in Vernon Township

Cozy 1-bedroom condo-Ski in/out/Waterpark/King Bed/WIFI/Parking
2.5 star property
9.2 out of 10, Wonderful, (7)
"We stayed in this unit and absolutely loved it. We were just a short drive away from the all the orchards in Warwick, NY. The accommodations were perfectly located with quite a few things to do in the area. We will stay again. "
United States
Jonathan O.
$220 nightly
The price is $249
Jan 4 - Jan 5
Total with taxes and fees
Cozy 1-bedroom condo-Ski in/out/Waterpark/King Bed/WIFI/Parking
Interior
5 Min to Downtown Warwick, Wineries, Breweries, Hikes, Shops, & Greenwood Lake!

Vacation Home in Warwick

5 Min to Downtown Warwick, Wineries, Breweries, Hikes, Shops, & Greenwood Lake!
2.0 star property
10.0 out of 10, Exceptional, (5)
"Had a lovely weekend in the little red barn. And the little market next door has the best breakfast egg and bacon sandwich."
United States
michelle d.
5 Min to Downtown Warwick, Wineries, Breweries, Hikes, Shops, & Greenwood Lake!
Private kitchen
Treeview - Cozy 2 BR Apartment - Fast WiFi ~ 1 hr from NYC - 5 mins to downtown

Apartment in Port Jervis

Treeview - Cozy 2 BR Apartment - Fast WiFi ~ 1 hr from NYC - 5 mins to downtown
10.0 out of 10, Exceptional, (6)
"House was clean and parking was easy! Close to downtown Port Jervis, with some great restaurants. The owners were so kind, and were so helpful!"
United States
Jen C.
$258 nightly
The price is $305
Jan 4 - Jan 5
Total with taxes and fees
Treeview - Cozy 2 BR Apartment - Fast WiFi ~ 1 hr from NYC - 5 mins to downtown
Interior
Couple's Serenity Cabin * Hot Tub *Lake

Cabin in Milford

Couple's Serenity Cabin * Hot Tub *Lake
10.0 out of 10, Exceptional, (4)
"Lovely quaint stay!"
United States
Kelly G.
$382 nightly
The price is $385
Jan 12 - Jan 13
Total with taxes and fees
Couple's Serenity Cabin * Hot Tub *Lake
Dining
Renovated House w/Hot Tub, Deck, Grill & Fire Pit

Vacation Home in Goshen

Renovated House w/Hot Tub, Deck, Grill & Fire Pit
10.0 out of 10, Exceptional, (59)
"Clean and comfortable accommodations, very close to Legoland and Castle Fun Center! The kids loved the room with bunk beds, and it had a big selection of children's books and some toys, which was a nice bonus!"
United States
Jennifer K.
$456 nightly
The price is $477
Jan 4 - Jan 5
Total with taxes and fees
Renovated House w/Hot Tub, Deck, Grill & Fire Pit
Outdoor dining
Luxe 10 guest Cottage Ski/Golf/Fire Pit/Lakes/Hike

Cottage in Vernon Township

Luxe 10 guest Cottage Ski/Golf/Fire Pit/Lakes/Hike
2.0 star property
8.8 out of 10, Excellent, (3)
"House was beautiful! Airy, cool and bedrooms were comfortable! Such a cute cottage and outdoor fire pit was amazing."
United States
Cherlyn I.
$426 nightly
The price is $481
Jan 5 - Jan 6
Total with taxes and fees
Luxe 10 guest Cottage Ski/Golf/Fire Pit/Lakes/Hike
Fridge, microwave, oven, stovetop
2 bedroom cozy condo with parking on premises

Condo in Vernon Township

2 bedroom cozy condo with parking on premises
10.0 out of 10, Exceptional, (33)
"The place was beautiful. Would highly recommended staying here. "
United States
Ranada
$261 nightly
The price is $295
Jan 5 - Jan 6
Total with taxes and fees
2 bedroom cozy condo with parking on premises
Exterior
Hello Small Stone

Cottage in Middletown

Hello Small Stone
9.6 out of 10, Exceptional, (5)
"The house was great. It was nice to sit and relax by the small pond in the back."
United States
John H.
$388 nightly
The price is $439
Feb 1 - Feb 2
Total with taxes and fees
Hello Small Stone
Outdoor pool, a heated pool
Luxury School House Retreat With Sauna & Pool- 1HR from NYC

Villa in New Hampton

Luxury School House Retreat With Sauna & Pool- 1HR from NYC
10.0 out of 10, Exceptional, (18)
"The best was relaxing by the pool. The house had everything we needed. We would definitely go back if we were ever in the area"
United States
Erin L.
$1,123 nightly
The price is $1,327
Jan 6 - Jan 7
Total with taxes and fees
Luxury School House Retreat With Sauna & Pool- 1HR from NYC
Fridge, microwave, oven, stovetop
Two Full Baths in Newly Renovated ski golf Condo! New on Market!!

Condo in Vernon Township

Two Full Baths in Newly Renovated ski golf Condo! New on Market!!
10.0 out of 10, Exceptional, (29)
"Great time great location"
United States
R J.
$301 nightly
The price is $340
Jan 6 - Jan 7
Total with taxes and fees
Two Full Baths in Newly Renovated ski golf Condo! New on Market!!
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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Top Glenwood Hotel Reviews

Sleep Inn & Suites Middletown - Goshen

Sleep Inn & Suites Middletown - Goshen

10/10 Excellent
"clean super safe lady at front desk was very helpful "
guadalupe 1-night trip
Posted 1 day ago
Sleep Inn & Suites Middletown - Goshen

Find out more about Glenwood

Everything you need to know about Glenwood vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Glenwood vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Glenwood vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Glenwood vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Glenwood. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Glenwood in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $148 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Glenwood rentals

At Expedia, we put the best Glenwood vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Glenwood rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Glenwood vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Glenwood. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

Frequently asked questions

Are there vacation rentals in Glenwood?

Yes, you can find vacation rentals close to popular local attractions in Glenwood, or you can choose a secluded option if you'd like a relaxing place to stay.

What are some of the best vacation rentals that Glenwood has to offer?

Luxe Retreat with Fireplace/WiFi/Pool near Water Parks, Golf Course, Wineries: This vacation home rental near Glenwood offers a fireplace, a garden, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a selection of games.

What’s there to see and do in Glenwood?

While exploring the area, visit family-friendly sights like Mountain Creek Waterpark, or get outside and enjoy nature at Upper Greenwood Lake. Wawayanda State Park and Warwick Valley Winery and Distillery are a couple of places you'll find in the larger area.

What’s a vacation rental in Glenwood like?

Vacation rentals are privately owned properties where you can stay for a few weeks or just a few days in Glenwood. Vacation rentals offer amenities such as laundry facilities and kitchens so you'll feel just like you're at home. If you're concerned about cleanliness, vacation rentals can provide a sense of privacy away from public hotel elevators and bustling concierge desks while still allowing you to travel. You'll also find more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a great choice for a family trip.