Photo by Allison Alano Flores

Highland 4 Stars Hotels

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Check availability on Highland 4 Star Hotels

Tonight
23 Dec - 24 Dec
Tomorrow
24 Dec - 25 Dec
This weekend
26 Dec - 28 Dec
Next weekend
2 Jan - 4 Jan

Our top choices for Highland 4-star hotels

Ballroom
DoubleTree by Hilton Poughkeepsie Convention Center

DoubleTree by Hilton Poughkeepsie Convention Center

DoubleTree by Hilton Poughkeepsie Convention Center
4.0 star property
Downtown Poughkeepsie
8.4 out of 10, Very good, (1000)
"Great place to stay a"
United States
Nicole
The price is HK$727
HK$852 total
includes taxes & fees
28 Dec - 29 Dec
DoubleTree by Hilton Poughkeepsie Convention Center
View from room
Woodstock Way Hotel

Woodstock Way Hotel

Woodstock Way Hotel
4.0 star property
Woodstock
9.6 out of 10, Exceptional, (217)
"The room and views were lovely, and we loved the Tannery cafe!"
United States
Katherine
Woodstock Way Hotel
Exterior
Mirbeau Inn & Spa

Mirbeau Inn & Spa

Mirbeau Inn & Spa
4.0 star property
Rhinebeck Village
9.6 out of 10, Exceptional, (309)
"The inn was lovely with attentive staff!"
United States
Karen
The price is HK$3,336
HK$4,060 total
includes taxes & fees
12 Jan - 13 Jan 2026
Mirbeau Inn & Spa
Terrace/patio
Cromwell Manor Inn

Cromwell Manor Inn

Cromwell Manor Inn
4.0 star property
Cornwall
9.4 out of 10, Exceptional, (94)
"Great stay!"
United States
Amrita
The price is HK$1,996
HK$2,358 total
includes taxes & fees
29 Dec - 30 Dec
Cromwell Manor Inn
Front of property
Hasbrouck House

Hasbrouck House

Hasbrouck House
4.0 star property
Stone Ridge
9.0 out of 10, Wonderful, (51)
"Cute place, staff very helpful"
United States
Rhonda
Hasbrouck House
Front of property
it's a good thing

it's a good thing

it's a good thing
4.5 star property
Clinton Corners
8.2 out of 10, Very good, (25)
"Lynn was a wonderful & accommodating host. Tje"
United States
Julie-Anne
it's a good thing
Terrace/patio
Kingston Carriage House

Kingston Carriage House

Kingston Carriage House
4.0 star property
Rondout
9.0 out of 10, Wonderful, (28)
"Amazing stay! Just make sure you get a lesson in how to turn the heat on... beautiful property walking distance from sights, shops, and cafes. Will absolutely stay there next time we are in Kingston!"
United States
Andrew
The price is HK$1,504
HK$1,752 total
includes taxes & fees
7 Jan - 8 Jan 2026
Kingston Carriage House
Outdoor spa tub
The Herwood Inn

The Herwood Inn

The Herwood Inn
4.5 star property
Woodstock
9.8 out of 10, Exceptional, (93)
"Quaint, quirky, very environmentally conscious, fun old vinyls, and a cedar fragrant hot tub!"
United States
Dietlinde
The price is HK$1,207
HK$1,352 total
includes taxes & fees
20 Jan - 21 Jan 2026
The Herwood Inn
Aerial view
Millbrook Country House Bed & Breakfast

Millbrook Country House Bed & Breakfast

Millbrook Country House Bed & Breakfast
4.0 star property
Millbrook
9.0 out of 10, Wonderful, (81)
"Gracious host and great breakfast "
United States
Gerald
The price is HK$1,478
HK$1,672 total
includes taxes & fees
18 Jan - 19 Jan 2026
Millbrook Country House Bed & Breakfast
Hiking
Journey Inn Bed & Breakfast

Journey Inn Bed & Breakfast

Journey Inn Bed & Breakfast
4.0 star property
Hyde Park
9.6 out of 10, Exceptional, (338)
"Great staff, the breakfast was amazing, location to surrounding attractions was great! I would stay again!"
United States
Shawn
The price is HK$1,742
HK$1,971 total
includes taxes & fees
18 Jan - 19 Jan 2026
Journey Inn Bed & Breakfast
Free daily local cuisine breakfast
The Millbrook Inn

The Millbrook Inn

The Millbrook Inn
4.0 star property
Millbrook
10.0 out of 10, Exceptional, (5)
"Love it! beautiful inn and amazing food!"
United States
Yasmin
The Millbrook Inn
45-inch Smart TV with cable channels, TV, fireplace
Dome House Retreat

Dome House Retreat

Dome House Retreat
4.0 star property
New Paltz
Dome House Retreat
Porch
Brinckerhoff Inn

Brinckerhoff Inn

Brinckerhoff Inn
4.0 star property
Fishkill
9.6 out of 10, Exceptional, (60)
"We had a great stay at the Brinckerhoff Inn. The property is beautiful and it was obvious how much work went into the restoration. The decor was very "Presidential" and definitely felt like you were back in the 18th Century. My husband and I had a lovely stay. The en suite bathroom was spacious and Molton brown amenities added a nice touch. We even snuck in a few games of pool in the downstairs game room. Bob was a terrific host and made us a delicious breakfast with a beautiful...
United States
Stacey
Brinckerhoff Inn
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Explore similar 5-star hotels

Many 5-star hotels have the same amenities as 4-star hotels. See all 5-star hotels in Highland.
Wildflower Farms, Auberge Collection

Wildflower Farms, Auberge Collection

2702 Main St Gardiner NY
The price is HK$9,400 per night from 7 Jan to 8 Jan
HK$9,400
HK$10,864 total
7 Jan - 8 Jan 2026
includes taxes & fees
9.4/10 Exceptional! (58 reviews)
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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.

Learn more about Highland

Perched above the Hudson River, this charming town offers stunning views from the Walkway Over the Hudson. Explore local wineries, pick your own apples at nearby orchards, or hike the scenic trails in Minnewaska State Park Preserve.

See all hotels in Highland
Walking across the walkway over the Hudson, get there early to avoid parking issues. Great place to walk your dog!
Photo by Allison Alano Flores
Open Photo by Allison Alano Flores

Top Highland Hotel Reviews

DoubleTree by Hilton Poughkeepsie Convention Center

DoubleTree by Hilton Poughkeepsie Convention Center

10/10 Excellent
"Clean rooms, very nice staff"
Shivani 1-night trip
Posted 8 days ago
DoubleTree by Hilton Poughkeepsie Convention Center

Frequently asked questions

How much does it cost to stay in a 4-star hotel in Highland?
To lock in a 4-star hotel in Highland that's within your budget, take advantage of Expedia's handy search filters. Browse the availability during your chosen dates and use our pricing filter to set your maximum rate. You can also list your results by the most budget-friendly stay first.

  • Search for the lowest price from HK$5,384

What's the difference between 5-star and 4-star hotels in Highland?
Offering a friendly guest experience and upmarket décor, 4-star hotels are a fabulous option for your Highland break. These kinds of stays generally come with lots of handy amenities that make it easy to kick back and relax — think large beds, bathrobes, restaurants and pools. Or enjoy even more lavishness at a 5-star hotel designed to indulge you in luxury perks and amenities. 24-hour front desk, oversized bathrooms and world-class dining are typically featured at these plush properties.
Does Highland have any 4-star all-inclusive resorts?
Enjoy a relaxing holiday experience where almost everything is included in the one upfront rate by using our "All inclusive" filter. Sticking to your budget is a piece of cake when your accommodation, meals and many activities are already taken care of. Want more options? Browse the amazing offers on Expedia's standard 4-star options in and around Highland.

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