Photo by Karen Wirtz

Find 4 Star Hotels in Highland, NY from $109

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Check availability on Highland 4 Star Hotels

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

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
$93 nightly
The price is $109
Dec 28 - Dec 29
Total with taxes and fees
DoubleTree by Hilton Poughkeepsie Convention Center
Superior Room, Fireplace, River View | 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
$277 nightly
The price is $305
Jan 5 - Jan 6, 2026
Total with taxes and fees
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
$462 nightly
The price is $522
Jan 12 - Jan 13, 2026
Total with taxes and fees
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
$263 nightly
The price is $311
Jan 15 - Jan 16, 2026
Total with taxes and fees
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
$424 nightly
The price is $475
Jan 1 - Jan 2, 2026
Total with taxes and fees
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
$141 nightly
The price is $160
Jan 1 - Jan 2, 2026
Total with taxes and fees
it's a good thing
Design House | 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
$224 nightly
The price is $250
Jan 6 - Jan 7, 2026
Total with taxes and fees
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
$144 nightly
The price is $162
Jan 20 - Jan 21, 2026
Total with taxes and fees
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
$190 nightly
The price is $215
Jan 18 - Jan 19, 2026
Total with taxes and fees
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
$224 nightly
The price is $253
Jan 18 - Jan 19, 2026
Total with taxes and fees
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
$576 nightly
The price is $652
Jan 4 - Jan 5, 2026
Total with taxes and fees
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
$1,238 nightly
The price is $1,387 total per night from Jan 5 to Jan 6
$1,387 total
Jan 5 - Jan 6, 2026
Total with taxes and 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 9 days ago
DoubleTree by Hilton Poughkeepsie Convention Center

Find out more about Highland

Highland Four Star Hotel Information

When you need to book a room with luxurious amazing amenities and the best rates, the 4 star hotels in Highland, New York are incredible options. Known for their extra perks, first-rate service, and fantastic locations, each of the Highland 4 star hotels offers the ultimate experience for globe-trotting travelers. Relax in your expertly designed room. Kick back with around-the-clock room service.

Get a good night’s sleep with the ultra-plush bedding, and freshen up in the morning with designer-inspired body products. It’s all available when you stay at one of the top book a four star hotels in Highland. What’s more, thanks to Expedia you might even score a cheap great deal on a 4 star hotel in Highland, New York, areas near the hottest attractions, so you can plan a sightseeing adventure and take advantage of unbeatable discounts in one fell swoop.

Whether you’re putting together a serene getaway or want to revel in the most vibrant entertainment district, 4 star Highland hotels offer everything your heart desires.

Frequently asked questions

How much does it cost to stay in a 4-star hotel in Highland?
To book a 4-star hotel in Highland that fits your budget, use Expedia's filters. Check out the availability during your travel dates and use our pricing filter to set your maximum rate. You can also sort your results by the most affordable stay first.

  • Search for the lowest price from $700

What's the difference between 5-star and 4-star hotels in Highland?
Offering an inviting traveler experience and upmarket surroundings, 4-star hotels are an excellent option for your Highland vacation. These kinds of accommodations generally feature loads of handy amenities that make it a breeze to unpack and unwind — think 24-hour room service, restaurants and gyms. Or live in the lap of luxury at a 5-star hotel designed to spoil you with exclusive perks and amenities. 24-hour front desk, premium toiletries and fine dining are typically featured at these deluxe retreats.
Does Highland have any 4-star all-inclusive resorts?
Enjoy a relaxing vacation experience where everything is included in the one upfront price by using our "All inclusive" filter. Budgeting is a cinch when your accommodations, food and many activities are already taken care of. Eager for more options? Browse the incredible offers on our standard 4-star options in and around Highland too.

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