Top Cottages in Orange County in 2026

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West Point Cadet Chapel, in upstate NY - open to the public daily - tours offered - beautiful!!

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Top Cities in Orange County

Middletown

West Point

Our top choices for Orange County cottages

1 bedroom, desk, iron/ironing board, free WiFi

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

Fort Montgomery

9.8 out of 10, Exceptional, (131 reviews)

9.8/10

Exceptional

(131 reviews)

"It has an incredible mountain and water view. "

MIHYUN

The price is HK$1,466

HK$1,466

HK$2,373 total

includes taxes & fees

5 Feb - 6 Feb

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

Cozy Haven: A Romantic Retreat in our Tiny House!

Middletown

6.8 out of 10, (11 reviews)

6.8/10

(11 reviews)

"we enjoyed the cozy home it is a nice place to get away"

Yidel

Cozy Haven: A Romantic Retreat in our Tiny House!

Hike & Fish: Outdoor Retreat Near Trails

3.0 star property

Westbrookville

Hike & Fish: Outdoor Retreat Near Trails

Hello Small Stone

Middletown

9.6 out of 10, Exceptional, (5 reviews)

9.6/10

Exceptional

(5 reviews)

"The house was great. It was nice to sit and relax by the small pond in the back."

John H.

Hello Small Stone

Luxe Family Home on Orange Lake w/ Private Dock!

3.0 star property

Newburgh

Luxe Family Home on Orange Lake w/ Private Dock!

Hudson Valley Retreat w/ Pool Near Greenwood Lake

3.0 star property

Monroe

10.0 out of 10, Exceptional, (2 reviews)

10/10

Exceptional

(2 reviews)

"fantastic accommodations"

David

Hudson Valley Retreat w/ Pool Near Greenwood Lake

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

Greenwood Lake

9.4 out of 10, Exceptional, (101 reviews)

9.4/10

Exceptional

(101 reviews)

"Cute, small and comfortable cabin overlooking Greenwood Lake. Spent a lot of time on the deck overlooking the lake. Even made a Sunday trip driving into NYC, no problem, not much traffic early. Location convenient to small towns, everyone friendly. A great place to stay. "

Andrew M.

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

Relaxing Farm Cottage Escape, 10 Min from LEGOLAND

Goshen

9.8 out of 10, Exceptional, (13 reviews)

9.8/10

Exceptional

(13 reviews)

"Beautiful location. We really enjoyed seeing the deer in the field every morning. "

Aaron M.

The price is HK$1,158

HK$1,158

HK$2,297 total

includes taxes & fees

22 Jan - 23 Jan

Relaxing Farm Cottage Escape, 10 Min from LEGOLAND

Charming Victorian Retreat w/ Hudson River Views

3.0 star property

Newburgh

Charming Victorian Retreat w/ Hudson River Views

Bright Cornwall-on-hudson Vacation Rental!

3.0 star property

Cornwall

10.0 out of 10, Exceptional, (1 review)

10/10

Exceptional

(1 review)

"Very nice property, very comfortable, close to multiple sightseeing location including bear mountain."

Poyuk

Bright Cornwall-on-hudson Vacation Rental!

Game Room, Yard & Fire Pit: Spacious Catskills Gem

3.0 star property

Sparrow Bush

10.0 out of 10, Exceptional, (1 review)

10/10

Exceptional

(1 review)

"We had stay a great stay in Sparrow Bush! The house was clean and spacious and had everything we needed. The host was incredibly helpful. Communication was great and he was quick to respond to any of our questions. Would definitely recommend to anyone looking to stay in Sparrow Bush! "

Annabelle

Game Room, Yard & Fire Pit: Spacious Catskills Gem

1 bedroom, iron/ironing board, WiFi, bed sheets

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

Sparrow Bush

9.4 out of 10, Exceptional, (11 reviews)

9.4/10

Exceptional

(11 reviews)

"A little off the beaten path, but a lovely Vrbo with excellent amenities with a nice natural surrounding."

Nicholas G.

The price is HK$682

HK$682

HK$2,174 total

includes taxes & fees

22 Jan - 23 Jan

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

Updated Home w/ Patio Half Mile to West Point

3.0 star property

Highland Falls

Updated Home w/ Patio Half Mile to West Point

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

Sparrow Bush

10.0 out of 10, Exceptional, (3 reviews)

10/10

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!"

Maggie Z.

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

Charming 2-bedroom cottage in delightful Greenwood Lake with WiFi, AC

Greenwood Lake

Charming 2-bedroom cottage in delightful Greenwood Lake with WiFi, AC

Warwick Vacation Rental w/ Private Yard & Fire Pit

3.0 star property

Warwick

10.0 out of 10, Exceptional, (1 review)

10/10

Exceptional

(1 review)

"I was relieved to find that the property looks just like and even better than the pictures online. "

Saudia

Warwick Vacation Rental w/ Private Yard & Fire Pit

Waterfall Cottage - Romantic Luxury Escape - nearby hiking, wineries and skiing

Warwick

10.0 out of 10, Exceptional, (155 reviews)

10/10

Exceptional

(155 reviews)

"Our stay was wonderful! Very comfortable, clean, and amazing view of waterfall!"

Anonymous traveller

Waterfall Cottage - Romantic Luxury Escape - nearby hiking, wineries and skiing

4 Mi to Hudson River: Cozy Newburgh Home!

3.0 star property

Newburgh

8.0 out of 10, Very good, (1 review)

8.0/10

Very good

(1 review)

4 Mi to Hudson River: Cozy Newburgh Home!

Family Home Close to Warwick, 5 Mi to Lake!

3.0 star property

Monroe

Family Home Close to Warwick, 5 Mi to Lake!

Charming Highland Falls Home < 2 Mi to West Point!

3.0 star property

Highland Falls

10.0 out of 10, Exceptional, (1 review)

10/10

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!!"

Mia

Charming Highland Falls Home < 2 Mi to West Point!

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

La Quinta Inn & Suites by Wyndham Middletown-Goshen

10/10 Excellent

"friendly staff"

thomas 1-night trip

Posted 1 day ago

La Quinta Inn & Suites by Wyndham Middletown-Goshen

Hampton Inn & Suites Newburgh Stewart Airport

10/10 Excellent

"There was a little bit of an awkward wait to actually check in that night, but still enjoyed my stay. May be a good idea to have more than one night front desk associate available going forward to avoid awkward waits to check in. "

Felicia 1-night trip

Posted 2 days ago

Hampton Inn & Suites Newburgh Stewart Airport