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Compare 528 Vacation Homes in Highland with updated reviews, rates, and availability.

Esopus Creek modern Tiny house Retreat!

9.8 out of 10, Exceptional, (23)
"Great little house for the holidays. We were looking for a place nearby or family where we could have our own space but still be close by. "
The price is AED 569
AED 830 total
includes taxes & fees
20 Jan - 21 Jan
Esopus Creek modern Tiny house Retreat!

Riverfront modern house with beautiful views

2.0 star property
10.0 out of 10, Exceptional, (1)
"My husband and I had an amazing time. Absolutely beautiful home, great location, and overall amazing experience. "
The price is AED 1,088
AED 1,735 total
includes taxes & fees
20 Jan - 21 Jan
Riverfront modern house with beautiful views

Charming 3-bedroom house with WiFi, AC in marvelous Hudson Valley.

Charming 3-bedroom house with WiFi, AC in marvelous Hudson Valley.

Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo

10.0 out of 10, Exceptional, (2)
"Communication was easy, location and parking was great! Very clean and cozy!"
The price is AED 951
AED 1,069 total
includes taxes & fees
19 Jan - 20 Jan
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo

HOT TUB w/ POOL, STREAM on 7 Acres, JUST 2 MINUTES FROM TOWN

10.0 out of 10, Exceptional, (88)
"The house and property were great. Very comfortable house that felt like home with a well equipped kitchen, two living rooms, great beds, fireplace, and spa. Pool was closed since it was winter. The property is wooded and feels like being in your own private park but is only a few minutes from downtown. Highly recommended!"
HOT TUB w/ POOL, STREAM on 7 Acres, JUST 2 MINUTES FROM TOWN

Luxurious & Enchanting Log House in Heart of Hudson Valley/Catskills, Upstate NY

10.0 out of 10, Exceptional, (36)
"We rented this house for ourselves and our friends for our wedding weekend around the corner. It was the best decision, large group and we had plenty of places to sleep, the yard gave ample space for activities, the sound system kept us entertained, and the kitchen made hosting a large group a breeze. Yuri was amazing in making himself available and our stay memorable. Can’t wait to visit again!"
Luxurious & Enchanting Log House in Heart of Hudson Valley/Catskills, Upstate NY

Pet-Friendly ‘Pond View Loft' w/ Private Pool!

9.6 out of 10, Exceptional, (11)
"Overall, it seemed like the property manager was not ready for guests. The toilet instantly broke, the pool hadn’t been cleaned in probably weeks, and the apartment had stained sheets. It’s a nice place but really not worth the money."
Pet-Friendly ‘Pond View Loft' w/ Private Pool!

Kingston Crawfish Cottage Near Catskills!

9.8 out of 10, Exceptional, (10)
"We enjoyed our stay at the crawfish cottage. It was clean and had everything we needed. The host, Diane, was great, friendly and very responsive. "
Kingston Crawfish Cottage Near Catskills!

1 HR NYC Getaway Awesome Newly Renovated Home on 4 Acres, Stunning Views

9.0 out of 10, Wonderful, (32)
"We enjoyed our stay however, the listing states all the beds are king sized and only 2 are. The other 2 are queen. Also (note for host) we forgot a pair of sunglasses and would like to have them mailed back if they are found, could you contact me if possible."
1 HR NYC Getaway Awesome Newly Renovated Home on 4 Acres, Stunning Views

Hiking/Climbing Paradise- walking distance to Mohonk/Gunks/Minnewaska

9.8 out of 10, Exceptional, (92)
"This property was spectacular. Immaculately clean and every detail done well. From a fully stocked and ready to go kitchen, to comfortable beds, sheets and towels. I’ll be back to stay here again and the host Michelle couldn’t have done more. Having had a few disappointing stays in other properties of late, this was a welcome game changer!!!"
Hiking/Climbing Paradise- walking distance to Mohonk/Gunks/Minnewaska

Spacious New Luxurious holiday house in lovely Hudson Valley

9.8 out of 10, Exceptional, (8)
"The house had room for all of us, spacious and comfortable with modern amenities. We enjoyed the large open kitchen, well equipped for making big meals, and especially loved the walk in pantry with sink, oven and coffee bar. The beds were comfy, the bathrooms deluxe. Large couch and huge TV in living room with cozy gas fireplace for us to gather and relax. Located on a quiet cul de sac, easy to get to local attractions. We enjoyed every minute of our stay."
Spacious New Luxurious holiday house in lovely Hudson Valley

NEW LISTING! Cozy Country Farmhouse with Hot Tub

9.4 out of 10, Exceptional, (3)
"Perfect property for a quiet weekend. Dogs had plenty of room to run free"
NEW LISTING! Cozy Country Farmhouse with Hot Tub

Amenity Packed Waterfront Retreat w/ Hot Tub & Wood Burning Stove!

10.0 out of 10, Exceptional, (5)
"I rented this house for my bridal party to stay at the weekend of my wedding. This place was absolutely stunning. It was very cozy and had a fantastic view. The check in process and communicating with the hosts was so easy. Would love to go back there again at some point. "
Amenity Packed Waterfront Retreat w/ Hot Tub & Wood Burning Stove!

The Queen City Cottage

7.4 out of 10, Good, (16)
"My wife and I, along with my two daughters and grandchildren stayed at the Queen City Cottage for 4 nights. We needed to add an extra day at the last minute and Marissa was very responsive and accommodating. The house was clean upon our arrival and entry was a breeze. It's a bedroom, 1.5 bath, with extra bathroom in basement in laundry room. Location wa great! Restaurants and shopping minutes away. Outdoor space was tranquil with table and chairs under covered back porch. Wifi was fine, TV had...
The Queen City Cottage

Bright Cornwall-On-Hudson Vacation Rental!

10.0 out of 10, Exceptional, (11)
"Excellent location in Cornwall-on-Hudson. Walking distance to coffee shop and restaurants. Happy to see Painter's Tavern has reopened. 2 Alices-a nice coffee shop to hang out. Home is bright and spacious with contemporary decor. Fully stocked. Two bathrooms a bonus for five of us. Planning to return next holiday season."
Bright Cornwall-On-Hudson Vacation Rental!

Historic Poughkeepsie Home Near Arlington & Vassar

9.8 out of 10, Exceptional, (9)
"Me and some friends came up to the area for a golf weekend and we had the BEST time! Host was extremely communicative and helpful, and the house was perfect for our needs. I'd definitely recommend a stay here! Only tip - the rooms get very bright in the morning, so bring an eye mask if you want to sleep in!"
Historic Poughkeepsie Home Near Arlington & Vassar

Special Second Day November discounts @ the River. Text host for discount

9.8 out of 10, Exceptional, (12)
"Beautiful views of the river and was close to all. Place was a bit dusty and the larger bedroom had a very hard bed. Owner was kind and communicative."
Special Second Day November discounts @ the River. Text host for discount

Updated Home w/ Patio Half Mile to West Point

10.0 out of 10, Exceptional, (23)
"Very well appointed home a short walk from the West Point gate that met all of our needs for a weekend of catching up, going for walks and attending a wedding. Property is close to Storm King Art Center which is a great way to spend a beautiful afternoon. We lost power for 17 hours (neighborhood transformer blew) and the owners could not have been more helpful. Would highly recommend this house. "
Updated Home w/ Patio Half Mile to West Point

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

10.0 out of 10, Exceptional, (37)
"Review of VRBO Home - Our Rockbound Highland Rating: ⭐⭐⭐⭐⭐ (5/5) - Exceeded Expectations I recently stayed at a VRBO home that completely surpassed my expectations! The home was not only beautiful but incredibly comfortable, offering all the amenities promised in the listing. It felt like a home away from home and matched the online photos perfectly, which made our stay even more enjoyable. The check-in process was seamless, and the communication with the property manager was top-notch. This...
Our Rockbound Highland Home - 2 Blocks from Thayer Gate - 1/2 Block to Main St.

Cozy Hudson Valley Retreat - 1950's Ranch Close to Everything

9.2 out of 10, Wonderful, (5)
"Maya's house is beautifully decorated with thoughtful touches. The living space is large and the neighborhood quiet. It's walking distance to the Kerhonkson Diner and Mill & Main, and a short drive to Minnewaska State Park Preserve and Kelder's Farms. Looking forward to coming back to this quaint oasis!"
The price is AED 569
AED 938 total
includes taxes & fees
1 Feb - 2 Feb
Cozy Hudson Valley Retreat - 1950's Ranch Close to Everything
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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Other property types in Highland

Our home is perfect for relaxing and having lots of fun, with near by activity’s

10.0 out of 10, Exceptional, (2)
"We enjoyed our stay. The host is very responsive. The location is 30 minutes from Beacon, 10 minutes from Poughkeepsie and 2 hrs from NYC. The office was a nice feature and the house has great WiFi. "
Our home is perfect for relaxing and having lots of fun, with near by activity’s

Enjoy a cozy, quiet spot off the main roads but close to hiking/biking trails!

9.8 out of 10, Exceptional, (26)
"The home was very clean. The house was great for us. Ryan was easy to communicate with. If you’re up early enough to see the sunrise, take a look from the front yard. It was beautiful."
Enjoy a cozy, quiet spot off the main roads but close to hiking/biking trails!

Mid-Century DJ’s Dream

10.0 out of 10, Exceptional, (24)
"My daughter needed a place to stay while visiting for the holiday. Kevin was easy to reach and responded quickly. The apartment is very cute and was the perfect size. Everything was clean and had some nice personal touches. Im sure a summertime stay would be lovely, when the garden is in bloom"
The price is AED 364
AED 584 total
includes taxes & fees
22 Jan - 23 Jan
Mid-Century DJ’s Dream
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.