Glenwood Holiday Rentals

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Our top choices for Glenwood holiday rentals

Forava Cabins - Tiny Cabin in the Woods

Forava Cabins - Tiny Cabin in the Woods
3.0 star property
Ringwood
10.0 out of 10, Exceptional, (1)
"Very cute, well decorated, quiet, and has everything we needed for a get away."
United States
Alexis
The price is AU$351
includes taxes & fees
5 Jan - 6 Jan 2026
Forava Cabins - Tiny Cabin in the Woods

Room 1 at The Warwick Inn – Cozy Elegance in the Heart of Town

Room 1 at The Warwick Inn – Cozy Elegance in the Heart of Town
Warwick
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.
The price is AU$224
includes taxes & fees
28 Jan - 29 Jan 2026
Room 1 at The Warwick Inn – Cozy Elegance in the Heart of Town

Serene lakeside oasis - fast WiFi 1.5 hrs from NYC, fire-pit & nature all around

Serene lakeside oasis - fast WiFi 1.5 hrs from NYC, fire-pit & nature all around
Sparrow Bush
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.
The price is AU$466
includes taxes & fees
11 Jan - 12 Jan 2026
Serene lakeside oasis - fast WiFi 1.5 hrs from NYC, fire-pit & nature all around

Villa Verde B&B, bsm, Greenwood Lake NY

Villa Verde B&B, bsm, Greenwood Lake NY
Greenwood Lake
10.0 out of 10, Exceptional, (12)
"The breakfast was lovely!"
United States
Tara
The price is AU$437
includes taxes & fees
2 Jan - 3 Jan 2026
Villa Verde B&B, bsm, Greenwood Lake NY

Relaxing Farm Cottage Escape, 10 Min from LEGOLAND

Relaxing Farm Cottage Escape, 10 Min from LEGOLAND
Goshen
9.8 out of 10, Exceptional, (12)
"Beautiful location. We really enjoyed seeing the deer in the field every morning. "
United States
Aaron M.
The price is AU$442
includes taxes & fees
8 Jan - 9 Jan 2026
Relaxing Farm Cottage Escape, 10 Min from LEGOLAND

Hike & Fish: Outdoor Retreat Near Trails

Hike & Fish: Outdoor Retreat Near Trails
3.0 star property
Westbrookville
The price is AU$460
includes taxes & fees
2 Jan - 3 Jan 2026
Hike & Fish: Outdoor Retreat Near Trails

Cozy 1-bedroom condo-Ski in/out/Waterpark/King Bed/WIFI/Parking

Cozy 1-bedroom condo-Ski in/out/Waterpark/King Bed/WIFI/Parking
2.5 star property
Vernon Township
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.
The price is AU$378
includes taxes & fees
27 Jan - 28 Jan 2026
Cozy 1-bedroom condo-Ski in/out/Waterpark/King Bed/WIFI/Parking

★Chic Chalet River Views & Access★

★Chic Chalet River Views & Access★
Montague
7.4 out of 10, Good, (3)
"Dirty. Ants. Not well stocked."
United States
odette w.
The price is AU$216
includes taxes & fees
21 Jan - 22 Jan 2026
★Chic Chalet River Views & Access★

Luxe Penthouse Loft on Main St- Steam Shower, Elevator, Parking, Views, Kitchen

Luxe Penthouse Loft on Main St- Steam Shower, Elevator, Parking, Views, Kitchen
Warwick
10.0 out of 10, Exceptional, (33)
"Great location within walking distance of boutiques and restaurants. Enjoyed our stay. "
United States
Cynthia W.
The price is AU$392
includes taxes & fees
20 Jan - 21 Jan 2026
Luxe Penthouse Loft on Main St- Steam Shower, Elevator, Parking, Views, Kitchen

Charming Milford-Montague Riverway Cottage

Charming Milford-Montague Riverway Cottage
Montague
8.0 out of 10, Very good, (1)
"This location was great for our purpose of visiting family in Port Jervis and was easy to find - even in the dark. Due to the lack of reviews, I'm guessing that this is a new listing and that there are kinks still being worked out. Without going into too much detail, there was no way the space had recently been cleaned and the description provided on the listing seems to be lifted from one of their other properties as there was no fire pit, no fireplace, no dishwasher and the house is definitely...
United States
Alicia T.
The price is AU$216
includes taxes & fees
28 Jan - 29 Jan 2026
Charming Milford-Montague Riverway Cottage

★Rare River Views & Access, Cabin by Eden Islands★

★Rare River Views & Access, Cabin by Eden Islands★
Montague
9.0 out of 10, Wonderful, (13)
"Nice convenient location, near the river and town. "
United States
Steve W.
The price is AU$213
includes taxes & fees
21 Jan - 22 Jan 2026
★Rare River Views & Access, Cabin by Eden Islands★

Hello Small Stone

Hello Small Stone
Middletown
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.
The price is AU$680
includes taxes & fees
31 Jan - 1 Feb 2026
Hello Small Stone

★Scenic Views & River Access, Cozy River Home ★

★Scenic Views & River Access, Cozy River Home ★
Montague
9.0 out of 10, Wonderful, (11)
"We were visiting for our daughtets wedding and needed a place mearby that accommodates pets. Nothing to look at on the outside but the inside is very nice. Very comfortableorganized and a good selection of teas and some coffee."
United States
ADAM K.
The price is AU$215
includes taxes & fees
21 Jan - 22 Jan 2026
★Scenic Views & River Access, Cozy River Home ★

Couple's Serenity Cabin * Hot Tub *Lake

Couple's Serenity Cabin * Hot Tub *Lake
Milford
10.0 out of 10, Exceptional, (4)
"Lovely quaint stay!"
United States
Kelly G.
The price is AU$586
includes taxes & fees
20 Jan - 21 Jan 2026
Couple's Serenity Cabin * Hot Tub *Lake

Lake Glenwood A-Frame Cabin stunning views, fire pit, game room, Pet Friendly

Lake Glenwood A-Frame Cabin stunning views, fire pit, game room, Pet Friendly
Sussex
10.0 out of 10, Exceptional, (37)
"Wonderful place and cozy will book again "
United States
Alex P.
The price is AU$586
includes taxes & fees
12 Jan - 13 Jan 2026
Lake Glenwood A-Frame Cabin stunning views, fire pit, game room, Pet Friendly

5 Min to Downtown Warwick, Wineries, Breweries, Hikes, Shops, & Greenwood Lake!

5 Min to Downtown Warwick, Wineries, Breweries, Hikes, Shops, & Greenwood Lake!
2.0 star property
Warwick
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.
The price is AU$668
includes taxes & fees
3 Jan - 4 Jan 2026
5 Min to Downtown Warwick, Wineries, Breweries, Hikes, Shops, & Greenwood Lake!

Treeview - Cozy 2 BR Apartment - Fast WiFi ~ 1 hr from NYC - 5 mins to downtown

Treeview - Cozy 2 BR Apartment - Fast WiFi ~ 1 hr from NYC - 5 mins to downtown
Port Jervis
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.
The price is AU$482
includes taxes & fees
4 Jan - 5 Jan 2026
Treeview - Cozy 2 BR Apartment - Fast WiFi ~ 1 hr from NYC - 5 mins to downtown

Renovated House w/Hot Tub, Deck, Grill & Fire Pit

Renovated House w/Hot Tub, Deck, Grill & Fire Pit
Goshen
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.
The price is AU$717
includes taxes & fees
8 Jan - 9 Jan 2026
Renovated House w/Hot Tub, Deck, Grill & Fire Pit

Luxe 10 guest Cottage Ski/Golf/Fire Pit/Lakes/Hike

Luxe 10 guest Cottage Ski/Golf/Fire Pit/Lakes/Hike
2.0 star property
Vernon Township
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.
The price is AU$726
includes taxes & fees
8 Jan - 9 Jan 2026
Luxe 10 guest Cottage Ski/Golf/Fire Pit/Lakes/Hike

Luxe 10 guest Ski Chalet /Skiing/Pools/Tennis/Gym/Golf/Hiking

Luxe 10 guest Ski Chalet /Skiing/Pools/Tennis/Gym/Golf/Hiking
vernon
9.4 out of 10, Exceptional, (56)
"The house was so comfortable and had everything we needed to catch up over our girl's weekend. The porches and the living room were both excellent gathering spaces and we loved being so close to the spa. You can't beat the location and the house was lovely! The owners were also really responsive to questions we had over our stay. "
United States
Cailyn M.
The price is AU$751
includes taxes & fees
6 Jan - 7 Jan 2026
Luxe 10 guest Ski Chalet /Skiing/Pools/Tennis/Gym/Golf/Hiking
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

Find out more about Glenwood

Everything you need to know about Glenwood holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Glenwood holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Glenwood holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Glenwood holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Glenwood holiday rentals we have selected for you start as low as AU$378 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Glenwood rentals

At Expedia, we put the best Glenwood holiday 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 holiday.

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. 

Frequently asked questions

Are there holiday rentals in Glenwood?

Yes, there are holiday rentals close to the most popular sights in Glenwood, or you can select a more secluded option if you're looking for a relaxing stay.

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

Luxe Retreat with Fireplace/WiFi/Pool near Water Parks, Golf Course, Wineries: This holiday home rental outside of Glenwood offers a fireplace, a garden and a BBQ 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 that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as 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 wider area.

What’s a holiday rental in Glenwood like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Glenwood. Holiday rentals offer extras such as hot tubs, fire pits and patios so you'll feel right at home. If you're concerned about a clean environment, a holiday rental can provide a sense of security away from public hotel lifts and busy reception areas while still allowing you the experience of travel. You'll also get more space in a holiday rental than in a hotel, which is another reason why a holiday rental is an attractive choice for a family trip.