
Vacation Homes in Orange County
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Top Cities in Orange County

Middletown
Our top choices for Orange County vacation homes

1. Room 2 at The Warwick Inn – Cozy Elegance in the Heart of Town
Room 2 at The Warwick Inn – Cozy Elegance in the Heart of TownWarwick
8.8 out of 10, Excellent, (23 reviews)
The price is AED 327
AED 566 total
includes taxes & fees
16 Nov - 17 Nov

2. Cozy Lakefront Home - 278 FIVE STAR Reviews - Kayaks, Sunsets & Panoramic Views
Cozy Lakefront Home - 278 FIVE STAR Reviews - Kayaks, Sunsets & Panoramic ViewsNewburgh
10.0 out of 10, Exceptional, (335 reviews)

3. 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 TownWarwick
8.8 out of 10, Excellent, (28 reviews)
The price is AED 317
AED 542 total
includes taxes & fees
17 Nov - 18 Nov

4. New Farmhouse-Hot Tub, King Beds, Game Room, Pro Golf Sim & Amazing Valley View!
New Farmhouse-Hot Tub, King Beds, Game Room, Pro Golf Sim & Amazing Valley View!Montgomery
10.0 out of 10, Exceptional, (20 reviews)
The price is AED 2,578
AED 4,464 total
includes taxes & fees
30 Nov - 1 Dec

5. Cozy 3bedroom home in Highland Falls, only a five-minute walk from West Point NY
Cozy 3bedroom home in Highland Falls, only a five-minute walk from West Point NYHighland Falls
9.8 out of 10, Exceptional, (6 reviews)

6. 3BR Home with Fireplace & Hudson Valley views near Woodbury Commons, West Point
3BR Home with Fireplace & Hudson Valley views near Woodbury Commons, West PointCornwall
10.0 out of 10, Exceptional, (16 reviews)

7. 5 bdrm Victorian, built in 1881-With 21 rooms, on a hill on 4 VERY private acres
5 bdrm Victorian, built in 1881-With 21 rooms, on a hill on 4 VERY private acresNew Windsor
9.6 out of 10, Exceptional, (9 reviews)

8. 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 9Newburgh
9.8 out of 10, Exceptional, (53 reviews)

9. Updated Home w/ Patio Half Mile to West Point
Updated Home w/ Patio Half Mile to West PointHighland Falls
10.0 out of 10, Exceptional, (40 reviews)

10. Lakefront • 7BR Retreat • Sleeps 12 • Massage Chair
Lakefront • 7BR Retreat • Sleeps 12 • Massage ChairMonroe
10.0 out of 10, Exceptional, (5 reviews)
The price is AED 2,167
AED 4,043 total
includes taxes & fees
15 Nov - 16 Nov

11. Charming 3-bedroom house in Greenwood Lake walking distance to the Lake!
Charming 3-bedroom house in Greenwood Lake walking distance to the Lake!Greenwood Lake
10.0 out of 10, Exceptional, (9 reviews)

12. Walk to Hudson River Waterfront: Newburgh Home
Walk to Hudson River Waterfront: Newburgh HomeNewburgh
8.8 out of 10, Excellent, (3 reviews)

13. 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 reviews)

14. House on the Babbling Brook- Quiet 2BR + King Bed!
House on the Babbling Brook- Quiet 2BR + King Bed!Highland Falls
9.8 out of 10, Exceptional, (16 reviews)

15. The Cozy Goshen Home, 5mins from LEGOLAND and near skiing!
The Cozy Goshen Home, 5mins from LEGOLAND and near skiing!Goshen
10.0 out of 10, Exceptional, (26 reviews)

16. 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, (83 reviews)

17. Lakefront/Legoland/West Point Retreat Under 1 Hour From NYC! Heated pool & Spa!
Lakefront/Legoland/West Point Retreat Under 1 Hour From NYC! Heated pool & Spa!Monroe
10.0 out of 10, Exceptional, (56 reviews)

18. Fabulous 3bdrm Home w/parking!
Fabulous 3bdrm Home w/parking!Highland Falls
9.4 out of 10, Exceptional, (12 reviews)
The price is AED 775
AED 1,324 total
includes taxes & fees
8 Dec - 9 Dec

19. Lakefront Cove | Dock • Kayaks • Paddleboards
Lakefront Cove | Dock • Kayaks • PaddleboardsGreenwood Lake
10.0 out of 10, Exceptional, (5 reviews)

20. Cozy Chic Lakehouse Retreat – The Perfect Base for Year-Round Getaways
Cozy Chic Lakehouse Retreat – The Perfect Base for Year-Round GetawaysGreenwood Lake
8.0 out of 10, Very good, (2 reviews)
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

Overlook Lodge at Bear Mountain
10/10 Excellent
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