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Holiday Rentals in Orange County

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Top Cities in Orange County

Newburgh showing a marina and boating
Holiday RentalsHoliday Rentals

Newburgh

Newburgh

Our top choices for Orange County holiday rentals

Interior
Large,Cozy,Bright Apartment, Business Themed.

Large,Cozy,Bright Apartment, Business Themed.

Large,Cozy,Bright Apartment, Business Themed.
Newburgh
9.0 out of 10, Wonderful, (15)
"Very cozy stay with responsive host"
United States
Adhith P.
The price is €416
includes taxes & fees
16 Dec - 17 Dec
Large,Cozy,Bright Apartment, Business Themed.
Property grounds
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Fort Montgomery
9.8 out of 10, Exceptional, (129)
"It has an incredible mountain and water view. "
United States
MIHYUN
The price is €268
includes taxes & fees
16 Dec - 17 Dec
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Microwave, oven, stovetop, dishwasher
The Eagle Nest 2bd, Newburgh near DIA:Beacon and Storm King

The Eagle Nest 2bd, Newburgh near DIA:Beacon and Storm King

The Eagle Nest 2bd, Newburgh near DIA:Beacon and Storm King
Newburgh
The Eagle Nest 2bd, Newburgh near DIA:Beacon and Storm King
Exterior
Modern penthouse suite in a restored grain tower with private roof deck.

Modern penthouse suite in a restored grain tower with private roof deck.

Modern penthouse suite in a restored grain tower with private roof deck.
Warwick
10.0 out of 10, Exceptional, (27)
"Wonderful stay!"
United States
Lisi M.
The price is €468
includes taxes & fees
16 Dec - 17 Dec
Modern penthouse suite in a restored grain tower with private roof deck.
Dining
Renovated House w/Hot Tub, Deck, Grill & Fire Pit

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, (58)
"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 €412
includes taxes & fees
4 Jan - 5 Jan 2026
Renovated House w/Hot Tub, Deck, Grill & Fire Pit
Terrace/patio
Ann Creek: Charming 2 BR fully renovated house at Greenwood Lake. Dog friendly.

Ann Creek: Charming 2 BR fully renovated house at Greenwood Lake. Dog friendly.

Ann Creek: Charming 2 BR fully renovated house at Greenwood Lake. Dog friendly.
Greenwood Lake
9.8 out of 10, Exceptional, (8)
"Awesome place. Cozy and great communication with owners. "
United States
Dominick P.
Ann Creek: Charming 2 BR fully renovated house at Greenwood Lake. Dog friendly.
Exterior
3 Bedroom Dream: Hudson Valley views, Woodbury Commons, West Point & Storm King

3 Bedroom Dream: Hudson Valley views, Woodbury Commons, West Point & Storm King

3 Bedroom Dream: Hudson Valley views, Woodbury Commons, West Point & Storm King
2.0 star property
Cornwall
3 Bedroom Dream: Hudson Valley views, Woodbury Commons, West Point & Storm King
TV, fireplace
Cozy Haven: A Romantic Retreat in our Tiny House!

Cozy Haven: A Romantic Retreat in our Tiny House!

Cozy Haven: A Romantic Retreat in our Tiny House!
Middletown
6.8 out of 10, (11)
"we enjoyed the cozy home it is a nice place to get away"
United States
Yidel
Cozy Haven: A Romantic Retreat in our Tiny House!
Outdoor dining
Cozy Easy Access to the Best of the Hudson Valley!

Cozy Easy Access to the Best of the Hudson Valley!

Cozy Easy Access to the Best of the Hudson Valley!
Cornwall
10.0 out of 10, Exceptional, (6)
"Very nice, quaint property. The location was great for us. It was spot on to the description and pictures. 👍"
United States
Heather M.
Cozy Easy Access to the Best of the Hudson Valley!
Interior
Luxury 9BR Retreat w/Pool & Hot Tub

Luxury 9BR Retreat w/Pool & Hot Tub

Luxury 9BR Retreat w/Pool & Hot Tub
Chester
7.0 out of 10, Good, (2)
"Pool was not open or usable but we were not interested in doing that "
United States
John D.
Luxury 9BR Retreat w/Pool & Hot Tub
Terrace/patio
Ultimate Lakeside Getaway on 5 Acres - Private Dock, Kayaks, Fire Pit - Sleeps 9

Ultimate Lakeside Getaway on 5 Acres - Private Dock, Kayaks, Fire Pit - Sleeps 9

Ultimate Lakeside Getaway on 5 Acres - Private Dock, Kayaks, Fire Pit - Sleeps 9
Newburgh
10.0 out of 10, Exceptional, (22)
"Great host, amazing area, perfect get away!"
United States
Gianna W.
Ultimate Lakeside Getaway on 5 Acres - Private Dock, Kayaks, Fire Pit - Sleeps 9
Outdoor spa tub
Waterfront Home with Hot Tub, Kayaks, and Fast Wifi

Waterfront Home with Hot Tub, Kayaks, and Fast Wifi

Waterfront Home with Hot Tub, Kayaks, and Fast Wifi
Greenwood Lake
10.0 out of 10, Exceptional, (30)
"We loved the house. It was a perfect and much needed short getaway for my husband and I. We brought our little dog Lenny and he loved it too! "
United States
Chelsea D.
The price is €399
includes taxes & fees
17 Dec - 18 Dec
Waterfront Home with Hot Tub, Kayaks, and Fast Wifi
House (1 Bedroom) | Interior
Hike & Fish: Outdoor Retreat Near Trails

Hike & Fish: Outdoor Retreat Near Trails

Hike & Fish: Outdoor Retreat Near Trails
3.0 star property
Westbrookville
The price is €262
includes taxes & fees
30 Dec - 31 Dec
Hike & Fish: Outdoor Retreat Near Trails
Fridge, microwave, oven, stovetop
Cozy country efficiency in the Hudson Valley

Cozy country efficiency in the Hudson Valley

Cozy country efficiency in the Hudson Valley
Newburgh
9.8 out of 10, Exceptional, (66)
"Such a cute place to stay"
United States
Melissa
The price is €271
includes taxes & fees
16 Dec - 17 Dec
Cozy country efficiency in the Hudson Valley
Smart TV, fireplace, books, computer monitors
Entire Lakeview House ~ Hot Tub ~ Firepit ~ Stunning View ~ Spacious Deck

Entire Lakeview House ~ Hot Tub ~ Firepit ~ Stunning View ~ Spacious Deck

Entire Lakeview House ~ Hot Tub ~ Firepit ~ Stunning View ~ Spacious Deck
Greenwood Lake
10.0 out of 10, Exceptional, (5)
"We had an amazing stay at this beautiful home! The views overlooking the lake and mountains are absolutely breathtaking—better than I could have imagined. The house itself is gorgeous, well-maintained, and equipped with everything needed for a comfortable stay. On top of that, the host was incredibly responsive and made sure everything was perfect. If you’re looking for a peaceful retreat with unbeatable scenery and top-notch hospitality, this is the place to be. I can't wait to return!"
United States
Sol K.
The price is €620
includes taxes & fees
16 Dec - 17 Dec
Entire Lakeview House ~ Hot Tub ~ Firepit ~ Stunning View ~ Spacious Deck
Fridge, microwave, oven, stovetop
New Farmhouse-Hot Tub, King Beds, Game Room & View

New Farmhouse-Hot Tub, King Beds, Game Room & View

New Farmhouse-Hot Tub, King Beds, Game Room & View
Montgomery
10.0 out of 10, Exceptional, (15)
"We loved our stay here! The property is gorgeous and the hosts were helpful and communicative. The house was clean and had everything we needed."
United States
Emily B.
New Farmhouse-Hot Tub, King Beds, Game Room & View
Fridge, microwave, oven, stovetop
Cozy cottage w/hot tub, game room & backyard. Close to West Point and Bethel.

Cozy cottage w/hot tub, game room & backyard. Close to West Point and Bethel.

Cozy cottage w/hot tub, game room & backyard. Close to West Point and Bethel.
New Windsor
10.0 out of 10, Exceptional, (63)
"Beautiful home - just as pictured. Many nice touches that made it a great stay. Would definitely stay at this home again. "
United States
Stacey H.
Cozy cottage w/hot tub, game room & backyard. Close to West Point and Bethel.
Interior
Our Rockbound Highland Home - 2 Blocks from Thayer Gate - 1/2 Block to Main St.

Our Rockbound Highland Home - 2 Blocks from Thayer Gate - 1/2 Block to Main St.

Our Rockbound Highland Home - 2 Blocks from Thayer Gate - 1/2 Block to Main St.
Highland Falls
10.0 out of 10, Exceptional, (39)
"Everything was good. Heather was very attentive."
United States
Jeannette P.
Our Rockbound Highland Home - 2 Blocks from Thayer Gate - 1/2 Block to Main St.
Exterior
West Point Family Retreat, 5 min walk to Thayer!

West Point Family Retreat, 5 min walk to Thayer!

West Point Family Retreat, 5 min walk to Thayer!
2.0 star property
Highland Falls
9.8 out of 10, Exceptional, (7)
"Nice houseAwesome kitchen Granddaughter loved the bunk bed and the many games"
United States
Randall T.
West Point Family Retreat, 5 min walk to Thayer!
Interior
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

Room 1 at The Warwick Inn – Cozy Elegance in the Heart of Town
Warwick
9.4 out of 10, Exceptional, (8)
"Nice to have top notch bar/restaurant downstairs!"
United States
John E
The price is €130
includes taxes & fees
18 Dec - 19 Dec
Room 1 at The Warwick Inn – Cozy Elegance in the Heart of Town
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 Orange County Hotel Reviews

Sleep Inn & Suites Middletown - Goshen

Sleep Inn & Suites Middletown - Goshen

10/10 Excellent
"Very nice and cleab"
Barry 2-night trip
Posted 7 hours ago
Sleep Inn & Suites Middletown - Goshen

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Holiday Homes in Orange County

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