A suspension bridge over a river, surrounded by autumn-colored trees.

Cottages in Orange County

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Check prices for these dates

In two weeks
13 Nov - 15 Nov
In two months
25 Dec - 27 Dec
In three months
22 Jan - 24 Jan
In four months
19 Feb - 21 Feb

Top Cities in Orange County

A lake surrounded by autumn-colored trees reflecting on the water.
CottagesCottages

Middletown

Middletown

Our top choices for Orange County cottages

A house with a view of a bridge and mountains.

1. 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, (149 reviews)
"We had a great stay!!"
United States
Jasmine
The price is AED 727
AED 1,215 total
includes taxes & fees
28 Oct - 29 Oct
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
A deck with a colorful striped cushion, overlooking a lake with a rainbow and forested hills in the background.

2. A romantic cottage and artist's retreat looking down over an enchanted lake

A romantic cottage and artist's retreat looking down over an enchanted lake
Greenwood Lake
9.4 out of 10, Exceptional, (105 reviews)
"It was an awesome stay we loved the couple days we got to spend there!!"
United States
Vincent G.
A romantic cottage and artist's retreat looking down over an enchanted lake
A rustic cabin with a stone exterior, wooden deck, and a small porch.

3. Hello Small Stone

Hello Small Stone
Middletown
9.8 out of 10, Exceptional, (7 reviews)
"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 AED 462
AED 1,362 total
includes taxes & fees
28 Oct - 29 Oct
Hello Small Stone
A grey sectional sofa with patterned cushions, a round wooden coffee table with a green plant, and a window with a view of trees.

4. Relaxing Farm Cottage Escape, 10 Min from LEGOLAND

Relaxing Farm Cottage Escape, 10 Min from LEGOLAND
Goshen
9.4 out of 10, Exceptional, (17 reviews)
"Great place to stay when visiting Legoland. Convenient location and comfortable and clean."
United States
Jessica C.
The price is AED 545
AED 1,082 total
includes taxes & fees
1 Nov - 2 Nov
Relaxing Farm Cottage Escape, 10 Min from LEGOLAND
A white single-story house with a stone pathway leading to the front door, surrounded by trees and a well-maintained lawn.

5. Historic 1800s Cornwall-on-hudson Cottage!

Historic 1800s Cornwall-on-hudson Cottage!
3.0 star property
Cornwall
10.0 out of 10, Exceptional, (2 reviews)
"We loved everything about this property. The host was easy to connect with. The cottage was well stocked and spotless. The cottage and yard were absolutely beautiful. Would definitely book again."
United States
Anthony
Historic 1800s Cornwall-on-hudson Cottage!
A two-story wooden house with a gravel driveway and a small front yard.

6. NEW Spacious 5 bedrooms with Public Lake & Beach Access and Kayak!

NEW Spacious 5 bedrooms with Public Lake & Beach Access and Kayak!
Greenwood Lake
10.0 out of 10, Exceptional, (8 reviews)
"We enjoyed! A little too mosquito-ey, but otherwise a great stay."
United States
Ayala R.
NEW Spacious 5 bedrooms with Public Lake & Beach Access and Kayak!
A white single-story house with a stone pathway leading to the front door, surrounded by trees and a well-maintained lawn.

7. Historic 1800s Cornwall-On-Hudson Cottage!

Historic 1800s Cornwall-On-Hudson Cottage!
Cornwall-On-Hudson
10.0 out of 10, Exceptional, (43 reviews)
"The place was beautiful and the neighborhood clean. The hosts also provided a well stocked kitchen."
United States
Rachel L.
Historic 1800s Cornwall-On-Hudson Cottage!
A wooden deck with a 'COME IN' mat, white siding, and a view of dense green trees.

8. Hudson Valley Retreat w/ Pool Near Greenwood Lake

Hudson Valley Retreat w/ Pool Near Greenwood Lake
3.0 star property
Monroe
10.0 out of 10, Exceptional, (4 reviews)
"The house was very quiet and exactly as advertised. Would stay again!"
United States
Scott
The price is AED 779
AED 1,897 total
includes taxes & fees
8 Nov - 9 Nov
Hudson Valley Retreat w/ Pool Near Greenwood Lake
A rustic cabin with a wooden deck and stairs leading to a second-story balcony, surrounded by a forest.

9. Magical, all season, multilevel treehouse on beautiful 120 acre property.

Magical, all season, multilevel treehouse on beautiful 120 acre property.
Sparrow Bush
10.0 out of 10, Exceptional, (3 reviews)
"Our two young children absolutely loved our stay at the treehouse! Such a unique and fun way to spend a few days in the woods!"
United States
Maggie Z.
Magical, all season, multilevel treehouse on beautiful 120 acre property.
A wooden deck with a barbecue grill and a trash can.

10. Hike & Fish: Outdoor Retreat Near Trails

Hike & Fish: Outdoor Retreat Near Trails
3.0 star property
Westbrookville
The price is AED 779
AED 1,262 total
includes taxes & fees
28 Oct - 29 Oct
Hike & Fish: Outdoor Retreat Near Trails
A wooden deck with a 'COME IN' mat, white siding, and a view of dense green trees.

11. Hudson Valley Retreat w/ Pool Near Greenwood Lake

Hudson Valley Retreat w/ Pool Near Greenwood Lake
Monroe
10.0 out of 10, Exceptional, (9 reviews)
"We loved our stay! It was the perfect size for our small family. The property was extremely well maintained and there was a lot to do near by. We would definitely book here again!"
United States
Marc
The price is AED 606
AED 2,000 total
includes taxes & fees
8 Nov - 9 Nov
Hudson Valley Retreat w/ Pool Near Greenwood Lake
A wooden deck with outdoor seating, a view of the lake, and a building with large windows.

12. Cozy Cottage on the Lake

Cozy Cottage on the Lake
Port Jervis
10.0 out of 10, Exceptional, (1 review)
"This is a beautiful home on a quiet lake. We thoroughly relaxed and enjoyed our time here."
United States
Shannon F.
Cozy Cottage on the Lake
A cabin with a front porch, a staircase, and a large window.

13. Huguenot Retreat w/ Screened Porch & Lake Access!

Huguenot Retreat w/ Screened Porch & Lake Access!
Huguenot
9.6 out of 10, Exceptional, (5 reviews)
"Nice and relaxing and we will return! Would include directions on getting into the actual area as its so secluded it rock roads and can be confusing. Also include directions on how to get to the lake/access. But definitely would recommend to anyone. Out back firepit/grill is perfect spot!"
United States
Dave H.
Huguenot Retreat w/ Screened Porch & Lake Access!
Interior

14. Charming Highland Falls Home < 2 Mi to West Point!

Charming Highland Falls Home < 2 Mi to West Point!
3.0 star property
Highland Falls
10.0 out of 10, Exceptional, (1 review)
"Fabulous place - great for our family weekend at West Point. Plenty of room, lovely kitchen, and lots of seating - whole group of us could watch the baseball playoffs. Terrific - not a single problem or complaint!!"
United States
Mia
Charming Highland Falls Home < 2 Mi to West Point!
A covered porch with wooden flooring, a green sofa, and a table with a green vase.

15. Luxe Family Home on Orange Lake w/ Private Dock!

Luxe Family Home on Orange Lake w/ Private Dock!
3.0 star property
Newburgh
Luxe Family Home on Orange Lake w/ Private Dock!
A cabin with a front porch, a staircase, and a large window.

16. Huguenot Retreat w/ Screened Porch & Lake Access!

Huguenot Retreat w/ Screened Porch & Lake Access!
3.0 star property
Huguenot
Huguenot Retreat w/ Screened Porch & Lake Access!
A two-story house with a red front door, a small porch, and a garden with a stone pathway.

17. 4 Mi to Hudson River: Cozy Newburgh Home!

4 Mi to Hudson River: Cozy Newburgh Home!
3.0 star property
Newburgh
8.0 out of 10, Very good, (1 review)
4 Mi to Hudson River: Cozy Newburgh Home!
An outdoor patio with a stone wall, a wooden fence, and a table with chairs.

18. Updated Home w/ Patio Half Mile to West Point

Updated Home w/ Patio Half Mile to West Point
3.0 star property
Highland Falls
Updated Home w/ Patio Half Mile to West Point
A wooden deck with yellow chairs and a wooden railing.

19. Port Jervis Home ~ 8 Acres w/ Mountain View!

Port Jervis Home ~ 8 Acres w/ Mountain View!
3.0 star property
Port Jervis
Port Jervis Home ~ 8 Acres w/ Mountain View!
Exterior

20. Luxe Montgomery Home w/ Hot Tub Near Angry Orchard

Luxe Montgomery Home w/ Hot Tub Near Angry Orchard
3.0 star property
Montgomery
Luxe Montgomery Home w/ Hot Tub Near Angry Orchard
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

The Thayer Hotel at West Point

The Thayer Hotel at West Point

10/10 Excellent
"Exquisite hotel."
Christine 1-night trip
Posted 12 hours ago
The Thayer Hotel at West Point

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