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Check prices for these dates

Next weekend
Aug 15 - Aug 17
In two weeks
Aug 22 - Aug 24
In one month
Sep 5 - Sep 7
In two months
Oct 3 - Oct 5

Browse Select Highland Vacation Homes

The Farm at Hyde Park
Exterior

The Farm at Hyde Park

9.8 out of 10, Exceptional, (75)
"We were visiting the Culinary Institute highly recommend it."
The Farm at Hyde Park
Cozy Lakefront Home - 278 FIVE STAR Reviews - Kayaks, Sunsets & Panoramic Views
Outdoor dining

Cozy Lakefront Home - 278 FIVE STAR Reviews - Kayaks, Sunsets & Panoramic Views

10.0 out of 10, Exceptional, (301)
"The lake views at this house are absolutely worth the trip and the money. It's a beautiful spot. And the host, Don, is super responsive, thoughtful and accommodating. Highly recommend!"
The price is CA $618
CA $818 total
includes taxes & fees
Aug 24 - Aug 25
Cozy Lakefront Home - 278 FIVE STAR Reviews - Kayaks, Sunsets & Panoramic Views
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
Outdoor dining

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

9.8 out of 10, Exceptional, (27)
"Perfect for small family stay over for a wedding ! "
The price is CA $356
CA $461 total
includes taxes & fees
Aug 31 - Sep 1
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.
Fridge, microwave, oven, stovetop

Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.

10.0 out of 10, Exceptional, (86)
"We loved our stay. It was great for a family Thanksgiving"
Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.
Where the Broadway Stars Vacation! Private Woodstock getaway & walk to town!
3 bedrooms, iron/ironing board, WiFi, bed sheets

Where the Broadway Stars Vacation! Private Woodstock getaway & walk to town!

10.0 out of 10, Exceptional, (176)
"Loved our stay and the house. Everything was wonderful. I will say it was a little farther than 'a walk into town' and we did Uber everywhere. Everything at the house was great - nice relaxing spot!!"
Where the Broadway Stars Vacation! Private Woodstock getaway & walk to town!
Esopus Creek modern Tiny house Retreat!
Outdoor dining

Esopus Creek modern Tiny house Retreat!

9.6 out of 10, Exceptional, (45)
"4 of us stayed for a fishing trip and had a blast. Nice place at a reasonable price. Would stay again. "
The price is CA $204
CA $332 total
includes taxes & fees
Aug 17 - Aug 18
Esopus Creek modern Tiny house Retreat!
Scenic New Paltz Escape: River Views, Hot Tub & Deck | Dream House in the Gunks
Fridge, microwave, oven, stovetop

Scenic New Paltz Escape: River Views, Hot Tub & Deck | Dream House in the Gunks

2.0 star property
9.8 out of 10, Exceptional, (12)
"A group of girlfriends stayed for a 2 night visit. Everything was just as listed, the home was in the perfect location, well stocked, and beautiful inside. We would definitely return again. "
The price is CA $550
CA $814 total
includes taxes & fees
Aug 13 - Aug 14
Scenic New Paltz Escape: River Views, Hot Tub & Deck | Dream House in the Gunks
Red Barn Retreat - Shawangunk Mountains Getaway
Outdoor dining

Red Barn Retreat - Shawangunk Mountains Getaway

10.0 out of 10, Exceptional, (50)
"The property is close to Minawaska State Park where we went hiking. We enjoyed the hot tub and had a nice stay. There are a number of nice restaurants nearby too."
Red Barn Retreat - Shawangunk Mountains Getaway
Ultimate Lakeside Getaway on 5 Acres - Private Dock, Kayaks, Fire Pit - Sleeps 9
Terrace/patio

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

9.6 out of 10, Exceptional, (8)
Ultimate Lakeside Getaway on 5 Acres - Private Dock, Kayaks, Fire Pit - Sleeps 9
New Breathtaking Catskill Retreat with Views and Hot Tub, The Nest Retreat in Woodstock Catskill
2 bedrooms, iron/ironing board, WiFi, bed sheets

New Breathtaking Catskill Retreat with Views and Hot Tub, The Nest Retreat in Woodstock Catskill

10.0 out of 10, Exceptional, (18)
"Really enjoyed this place . Very clean , beautiful views, close to Woodstock town !"
New Breathtaking Catskill Retreat with Views and Hot Tub, The Nest Retreat in Woodstock Catskill
1 HR NYC Getaway Awesome Newly Renovated Home on 4 Acres, Stunning Views
Smart TV, fireplace

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

9.0 out of 10, Wonderful, (37)
"Perfect spot for a get together with friends... kitchen, dining room and living room all connected so you're always together and not missing out on the fun. Comfy couches and plenty of space for large board games."
1 HR NYC Getaway Awesome Newly Renovated Home on 4 Acres, Stunning Views
Dog friendly private 3-bedroom house bordering the Mohonk Preserve
Exterior

Dog friendly private 3-bedroom house bordering the Mohonk Preserve

10.0 out of 10, Exceptional, (7)
Dog friendly private 3-bedroom house bordering the Mohonk Preserve
Secluded family retreat within minutes of Woodstock village
Outdoor dining

Secluded family retreat within minutes of Woodstock village

10.0 out of 10, Exceptional, (41)
"My wife and I came for just the weekend and enjoyed the house as always! Comfortable, clean, spacious, and convenient to everything yet quiet as can be. "
Secluded family retreat within minutes of Woodstock village
The Studio at the Inn at High Falls
Exterior

The Studio at the Inn at High Falls

8.0 out of 10, Very good, (26)
"I had a great stay here, it’s just as listed; simple but has everything that I needed, check in was easy, communication was good, and bed was comfortable!"
The price is CA $155
CA $372 total
includes taxes & fees
Aug 11 - Aug 12
The Studio at the Inn at High Falls
Welcome to New Paltz. Charming 3-bedroom house with AC, WIFI,
Private kitchen

Welcome to New Paltz. Charming 3-bedroom house with AC, WIFI,

The price is CA $276
CA $702 total
includes taxes & fees
Aug 11 - Aug 12
Welcome to New Paltz. Charming 3-bedroom house with AC, WIFI,
The Loft At The Inn At High Falls
1 bedroom, free WiFi, bed sheets

The Loft At The Inn At High Falls

9.2 out of 10, Wonderful, (16)
"this was just a lovely stay all around!! Will absolutely stay there again!"
The price is CA $248
CA $492 total
includes taxes & fees
Aug 11 - Aug 12
The Loft At The Inn At High Falls
Modern NY Home w/ Views By Hudson Valley Hiking!
TV, fireplace, books, video library

Modern NY Home w/ Views By Hudson Valley Hiking!

9.8 out of 10, Exceptional, (25)
"Lovely home and great proximity to Taconic Parkway for all points north and south. Owner very accomodating"
Modern NY Home w/ Views By Hudson Valley Hiking!
Heart of Woodstock — Unique Arts-and-Crafts Home: Outdoor Room and Heated Pool!
A heated pool

Heart of Woodstock — Unique Arts-and-Crafts Home: Outdoor Room and Heated Pool!

10.0 out of 10, Exceptional, (63)
"This was an excellent place to stay in such a beautiful area."
Heart of Woodstock — Unique Arts-and-Crafts Home: Outdoor Room and Heated Pool!
Stylish Cozy Home with Gorgeous Views!
Fridge, microwave, oven, stovetop

Stylish Cozy Home with Gorgeous Views!

10.0 out of 10, Exceptional, (25)
"Second time staying here; check in and out is super easy. Place is beautiful and comfortable. Perfect place to relax."
Stylish Cozy Home with Gorgeous Views!
Pet-Friendly ‘Pond View Loft' w/ Private Pool!
Dining

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

9.6 out of 10, Exceptional, (11)
"We loved the new furniture and sheets and blankets. Everything was spotless and felt super comfortable and homey. Big space as well! "
Pet-Friendly ‘Pond View Loft' w/ Private Pool!
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 Highland Hotel Reviews

Hampton Inn & Suites Poughkeepsie

Hampton Inn & Suites Poughkeepsie

10/10 Excellent
"You may want to check the thermometer in 529. It was set on 68 but was more like 78 in the room. Other than that, we had a great stay!"
Kevin 1-night trip
Posted 2 days ago
Hampton Inn & Suites Poughkeepsie