Washingtonville Holiday Rentals

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Our top choices for Washingtonville holiday rentals

Cozy 1-bedroom retreat minutes from West Point!

Cozy 1-bedroom retreat minutes from West Point!
Highland Falls
10.0 out of 10, Exceptional, (1)
"Easy check in , good comms, very nice and convenient while visiting West Point (order your Uber early!) "
United States
Zack C.
The price is HK$734
HK$1,474 total
includes taxes & fees
26 Jan - 27 Jan 2026
Cozy 1-bedroom retreat minutes from West Point!

Modern Zen Chalet at the Foot of Gunks w Mt. View and barrel outside sauna

Modern Zen Chalet at the Foot of Gunks w Mt. View and barrel outside sauna
2.0 star property
Gardiner
10.0 out of 10, Exceptional, (7)
"Great weekend getaway to reconnect with old friends!"
United States
Lisa D.
The price is HK$874
HK$1,761 total
includes taxes & fees
4 Jan - 5 Jan 2026
Modern Zen Chalet at the Foot of Gunks w Mt. View and barrel outside sauna

Quiet Apt with Coffee Bar, 1/2 Mile to West Point!

Quiet Apt with Coffee Bar, 1/2 Mile to West Point!
Highland Falls
9.8 out of 10, Exceptional, (14)
"Great Unit."
United States
Rudy R.
The price is HK$699
HK$2,067 total
includes taxes & fees
20 Jan - 21 Jan 2026
Quiet Apt with Coffee Bar, 1/2 Mile to West Point!

House on the Babbling Brook- Quiet 2BR + King Bed!

House on the Babbling Brook- Quiet 2BR + King Bed!
Highland Falls
10.0 out of 10, Exceptional, (5)
"A clean and convenient place to stay for visiting our cadet at West Point. Our hosts were very communicative and helpful. The home and parking situation was just as described. Nice quiet neighborhood, well maintained home. Hearing the babbling broom outside the living room window was very relaxing. Plan on staying here again!"
United States
Maria L.
The price is HK$863
HK$2,829 total
includes taxes & fees
20 Jan - 21 Jan 2026
House on the Babbling Brook- Quiet 2BR + King Bed!

Dream getaway apartment in the foot of Gunks Ridge

Dream getaway apartment in the foot of Gunks Ridge
Wallkill
9.6 out of 10, Exceptional, (24)
"Over all the property was clean and staff was very cooperative. Only problems were the beds were very hard which made it hard for us to get a good nights sleep. The larger room had bugs but the owner took care of it right away. We enjoyed our stay."
United States
Harriet
The price is HK$455
HK$1,289 total
includes taxes & fees
4 Jan - 5 Jan 2026
Dream getaway apartment in the foot of Gunks Ridge

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 HK$685
HK$1,197 total
includes taxes & fees
5 Jan - 6 Jan 2026
Room 1 at The Warwick Inn – Cozy Elegance in the Heart of Town

Nature Escape - studio in the forest

Nature Escape - studio in the forest
Middletown
The price is HK$2,324
HK$3,755 total
includes taxes & fees
31 Dec - 1 Jan 2026
Nature Escape - studio in the forest

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 HK$1,154
HK$2,274 total
includes taxes & fees
29 Dec - 30 Dec
Relaxing Farm Cottage Escape, 10 Min from LEGOLAND

Sleek Escape: Modern 3 BR- 4 Min from West Point !

Sleek Escape: Modern 3 BR- 4 Min from West Point !
Highland Falls
10.0 out of 10, Exceptional, (3)
"The host was prompt and attentive to any questions that arose. The home appeared exactly as depicted in the pictures and was perfect for a weekend stay close to family and The city!"
United States
Julio J.
The price is HK$1,088
HK$3,518 total
includes taxes & fees
14 Jan - 15 Jan 2026
Sleek Escape: Modern 3 BR- 4 Min from West Point !

Luxe Studio 2 on Main Street- Luxury Steam Shower, Kitchen

Luxe Studio 2 on Main Street- Luxury Steam Shower, Kitchen
Beacon
10.0 out of 10, Exceptional, (32)
"Great time and great place to stay "
United States
S S.
The price is HK$855
HK$1,870 total
includes taxes & fees
4 Jan - 5 Jan 2026
Luxe Studio 2 on Main Street- Luxury Steam Shower, Kitchen

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 HK$1,220
HK$2,251 total
includes taxes & fees
1 Jan - 2 Jan 2026
Villa Verde B&B, bsm, Greenwood Lake NY

Bright Contemporary Near The Best Hiking Trails

Bright Contemporary Near The Best Hiking Trails
Pine Bush
10.0 out of 10, Exceptional, (3)
"Nice property, very close to Sam’s Point trailheads. We were there to hike, so this was perfect. We would definitely book again."
United States
Amy L.
The price is HK$1,020
HK$4,010 total
includes taxes & fees
21 Jan - 22 Jan 2026
Bright Contemporary Near The Best Hiking Trails

Grant - A Tranquil One Bedroom Steps from River

Grant - A Tranquil One Bedroom Steps from River
Newburgh
9.6 out of 10, Exceptional, (41)
"Wonderful place! Beautifully decorated, high ceilings, yard, and easy access to the river and cafes. Perfect getaway from the city. Will stay again!"
United States
Emily G.
The price is HK$839
HK$2,013 total
includes taxes & fees
30 Dec - 31 Dec
Grant - A Tranquil One Bedroom Steps from River

Local Artist Inspired | Walk to WestPoint + King Bed

Local Artist Inspired | Walk to WestPoint + King Bed
Highland Falls
9.2 out of 10, Wonderful, (9)
"Great place to stay if you have a West Point student - super close to all West Point related activities. The place itself needs some work but it’s functional."
United States
Jesse C.
The price is HK$909
HK$3,177 total
includes taxes & fees
14 Jan - 15 Jan 2026
Local Artist Inspired | Walk to WestPoint + King Bed

Mondrian Manor - Cottage in the lower Catskills near Ellenville and Wurtsboro

Mondrian Manor - Cottage in the lower Catskills near Ellenville and Wurtsboro
Bloomingburg
10.0 out of 10, Exceptional, (1)
"The place was as described, quaint, clean, no issues with communication or check in"
United States
Stephen H.
The price is HK$1,088
HK$1,661 total
includes taxes & fees
29 Dec - 30 Dec
Mondrian Manor - Cottage in the lower Catskills near Ellenville and Wurtsboro

Cabin in the heart of the Hudson Valley, Cabin 4

Cabin in the heart of the Hudson Valley, Cabin 4
Newburgh
9.2 out of 10, Wonderful, (25)
"We LOVE this place and have stayed here twice."
United States
jennifer w.
The price is HK$1,003
HK$1,551 total
includes taxes & fees
29 Dec - 30 Dec
Cabin in the heart of the Hudson Valley, Cabin 4

Luxe Studio #3 on Main Street- Amazing Steam Shower! Washer/Dryer, Kitchen

Luxe Studio #3 on Main Street- Amazing Steam Shower! Washer/Dryer, Kitchen
Beacon
9.8 out of 10, Exceptional, (42)
"Adorable place to stay in an adorable town! "
United States
Mary L.
The price is HK$855
HK$1,807 total
includes taxes & fees
6 Jan - 7 Jan 2026
Luxe Studio #3 on Main Street- Amazing Steam Shower! Washer/Dryer, Kitchen

Create Memories at our Modern Waterfront 1 BR Apartment: Hike, Sip Wine, Relax!

Create Memories at our Modern Waterfront 1 BR Apartment: Hike, Sip Wine, Relax!
Wallkill
10.0 out of 10, Exceptional, (72)
"Everything was great nexactly as advertised. Terrific stargazing at night by the fire pit. Will definitely come back."
United States
David C.
The price is HK$895
HK$1,803 total
includes taxes & fees
29 Dec - 30 Dec
Create Memories at our Modern Waterfront 1 BR Apartment: Hike, Sip Wine, Relax!

Cozy Modern Stay - Walk to West Point & Main St!

Cozy Modern Stay - Walk to West Point & Main St!
2.0 star property
Highland Falls
The price is HK$544
HK$2,803 total
includes taxes & fees
29 Dec - 30 Dec
Cozy Modern Stay - Walk to West Point & Main St!

Beautiful First Flr, 2-Bedroom Apt w/ Free Parking

Beautiful First Flr, 2-Bedroom Apt w/ Free Parking
Highland Falls
10.0 out of 10, Exceptional, (5)
"Very nice property. We have a son at West Point and approximately an hour from New York City. Host was quick to respond to questions and provided excellent information. We will stay here again. "
United States
Mark V.
The price is HK$1,273
HK$2,180 total
includes taxes & fees
7 Jan - 8 Jan 2026
Beautiful First Flr, 2-Bedroom Apt w/ Free Parking
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 Washingtonville Hotel Reviews

Find out more about Washingtonville

Search for holiday rentals in Washingtonville on Expedia! You can easily find your home rentals, villas, holiday apartments in Washingtonville using one of the methods below:

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Look no further and take a look at our great range of rental properties in Washingtonville!

Frequently asked questions

Are there holiday rentals in Washingtonville?

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

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

Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo: This holiday home rental outside of Washingtonville offers a fireplace, a patio and air conditioning to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms, as well as a kitchen with an oven, a microwave and kitchenware, so that you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games.

How many holiday rentals are there in Washingtonville?

With 3 Expedia holiday rentals, you're guaranteed to find just the right place for your Washingtonville stay.

What can I see and do in Washingtonville?

Explore the area and family-friendly sights such as Ice Time Sports Complex, or get out into nature at a spot like Storm King Art Center. In the wider area, you’ll find Brotherhood Winery and National Purple Heart Hall of Honor.

What are holiday rentals like in Washingtonville?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Washingtonville. Holiday rentals offer extras like WiFi and washers and dryers so you'll be comfy for your stay. If you're concerned about a sanitised environment, a holiday rental can offer a sense of privacy away from shared hotel lifts and lobbies bustling with people while still allowing you the enjoyment of travel. You'll also have more space in a holiday rental than in a standard hotel, which makes a holiday rental a popular choice for family gatherings.