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Our top choices for Highland hotels

SureStay Plus Hotel by Best Western Highland Poughkeepsie

SureStay Plus Hotel by Best Western Highland Poughkeepsie
2.5 star property
Highland
7.8 out of 10, Good, (1,000 reviews)
"A good spot for a good price"
United States
Brittany
The price is ᅣ13,585
ᅣ15,217 total
includes taxes & fees
Jul 1 - Jul 2
SureStay Plus Hotel by Best Western Highland Poughkeepsie

Hyatt Place Poughkeepsie / Hudson Valley

Hyatt Place Poughkeepsie / Hudson Valley
3.0 star property
Crown Heights
9.0 out of 10, Wonderful, (1,004 reviews)
"This was a great location, the staff were very helpful and friendly, and the breakfast was great."
United States
Shannon
The price is ᅣ18,778
ᅣ21,806 total
includes taxes & fees
Jul 19 - Jul 20
Hyatt Place Poughkeepsie / Hudson Valley

Americas Best Value Inn New Paltz

Americas Best Value Inn New Paltz
2.0 star property
New Paltz
9.0 out of 10, Wonderful, (1,000 reviews)
"The location was perfect for us."
United States
Eleanor
The price is ᅣ18,903
ᅣ21,171 total
includes taxes & fees
Jul 23 - Jul 24
Americas Best Value Inn New Paltz

Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point

Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point
2.0 star property
New Windsor
8.4 out of 10, Very Good, (1,002 reviews)
"We stopped here for the night and it was perfect. Clean room and courteous staff."
United States
Kathleen
The price is ᅣ15,865
ᅣ18,741 total
includes taxes & fees
Jul 19 - Jul 20
Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point

The Crossroads Hotel, Newburgh

The Crossroads Hotel, Newburgh
3.0 star property
Newburgh
7.2 out of 10, Good, (793 reviews)
"Very clean room parking was safe and easy and the staff was helpful"
United States
Michael
The Crossroads Hotel, Newburgh

Quality Inn & Suites Fishkill South near I-84

Quality Inn & Suites Fishkill South near I-84
2.5 star property
Fishkill
9.0 out of 10, Wonderful, (1,003 reviews)
"Our room was clean and comfortable. It was just what we wanted for a short overnight stay. The staff were very friendly and accommodating. I would definitely stay there again."
United States
ANNE
The price is ᅣ15,514
ᅣ17,938 total
includes taxes & fees
Jul 19 - Jul 20
Quality Inn & Suites Fishkill South near I-84

Holiday Inn Express Poughkeepsie by IHG

Holiday Inn Express Poughkeepsie by IHG
2.5 star property
Poughkeepsie
8.8 out of 10, Excellent, (1,003 reviews)
"Great breakfast, clean place and convenient location"
United States
Jesus
The price is ᅣ15,689
ᅣ18,221 total
includes taxes & fees
Jul 5 - Jul 6
Holiday Inn Express Poughkeepsie by IHG

Super 8 by Wyndham Montgomery Maybrook

Super 8 by Wyndham Montgomery Maybrook
2.5 star property
Montgomery
6.4 out of 10, (1,001 reviews)
"Simple and easy quiet stay for overnight"
United States
Jose
The price is ᅣ12,422
ᅣ14,052 total
includes taxes & fees
Jun 29 - Jun 30
Super 8 by Wyndham Montgomery Maybrook

Best Western Plus The Inn & Suites At The Falls

Best Western Plus The Inn & Suites At The Falls
2.5 star property
Red Oaks Mill
7.6 out of 10, Good, (479 reviews)
"This place was excellent, especially for the price. Lovely setting and unique."
United States
Randall
The price is ᅣ18,361
ᅣ20,770 total
includes taxes & fees
Jul 9 - Jul 10
Best Western Plus The Inn & Suites At The Falls

Ramada by Wyndham Newburgh/West Point

Ramada by Wyndham Newburgh/West Point
2.0 star property
Newburgh
5.0 out of 10, (1,002 reviews)
"It’s close to Dennys, this place needs serious update and cleaning."
United States
Albert
The price is ᅣ11,645
ᅣ13,757 total
includes taxes & fees
Jun 29 - Jun 30
Ramada by Wyndham Newburgh/West Point

Courtyard by Marriott Kingston

Courtyard by Marriott Kingston
3.0 star property
Kingston
8.8 out of 10, Excellent, (1,001 reviews)
"It was great will definitely be back!!"
United States
Latisha
The price is ᅣ22,482
ᅣ25,179 total
includes taxes & fees
Jul 12 - Jul 13
Courtyard by Marriott Kingston

Hampton Inn & Suites Newburgh Stewart Airport

Hampton Inn & Suites Newburgh Stewart Airport
2.5 star property
Newburgh
9.2 out of 10, Wonderful, (1,000 reviews)
"Good location for our visit to West Point. Good size rooms with a nice breakfast"
United States
Margaret
The price is ᅣ19,761
ᅣ23,343 total
includes taxes & fees
Jul 12 - Jul 13
Hampton Inn & Suites Newburgh Stewart Airport

Spark by Hilton Fishkill

Spark by Hilton Fishkill
3.0 star property
Fishkill
8.2 out of 10, Very Good, (144 reviews)
"Great affordable stay overall."
United States
Caroline
The price is ᅣ14,985
ᅣ17,327 total
includes taxes & fees
Jul 19 - Jul 20
Spark by Hilton Fishkill

Hampton Inn & Suites Poughkeepsie

Hampton Inn & Suites Poughkeepsie
2.5 star property
Crown Heights
9.2 out of 10, Wonderful, (1,005 reviews)
"The beds were super comfy!"
United States
Debra
The price is ᅣ17,109
ᅣ19,867 total
includes taxes & fees
Jul 15 - Jul 16
Hampton Inn & Suites Poughkeepsie

Comfort Suites Fishkill near Interstate 84

Comfort Suites Fishkill near Interstate 84
2.5 star property
Fishkill
9.0 out of 10, Wonderful, (1,001 reviews)
"I just experienced a lovely stay at Comfort suites, the room was very comfortable, the bed was like floating on a cloud, the staff were very friendly accommodating, the breakfast buffet was excellent. Highly recommend staying there, also close to Rt 84 easy access"
United States
Marlene
The price is ᅣ15,990
ᅣ18,490 total
includes taxes & fees
Jul 27 - Jul 28
Comfort Suites Fishkill near Interstate 84

Quality Inn Hyde Park Poughkeepsie North

Quality Inn Hyde Park Poughkeepsie North
2.5 star property
Hyde Park
8.2 out of 10, Very Good, (1,000 reviews)
"Clean room, breakfast, easy access, parking"
United States
Diane
The price is ᅣ16,748
ᅣ18,947 total
includes taxes & fees
Jul 19 - Jul 20
Quality Inn Hyde Park Poughkeepsie North

Holiday Inn Express & Suites Montgomery by IHG

Holiday Inn Express & Suites Montgomery by IHG
2.5 star property
Montgomery
8.8 out of 10, Excellent, (875 reviews)
"Our stay for a day was great."
United States
Chime
The price is ᅣ16,821
ᅣ19,029 total
includes taxes & fees
Jul 26 - Jul 27
Holiday Inn Express & Suites Montgomery by IHG

Super 8 by Wyndham Kingston

Super 8 by Wyndham Kingston
2.5 star property
Kingston
6.2 out of 10, (1,001 reviews)
"Room was very clean and comfortable."
United States
Jose
The price is ᅣ14,993
ᅣ16,793 total
includes taxes & fees
Jul 12 - Jul 13
Super 8 by Wyndham Kingston

Borland House Inn

Borland House Inn
3.0 star property
Montgomery
9.2 out of 10, Wonderful, (169 reviews)
"Did you ever want to experience what it would be like to stay at a bed in breakfast? Well this is the place to go! So quaint and cute! Located right in the heart of the town of Montgomery. Plenty of things to walk to and see in the area. Brianna the manager was wonderful. Very helpful and informative. The breakfast choices were delicious. Would definitely stay here again and recommend it to others."
United States
roxanne
The price is ᅣ17,576
ᅣ20,481 total
includes taxes & fees
Jul 1 - Jul 2
Borland House Inn

Howard Johnson by Wyndham Newburgh/West Point

Howard Johnson by Wyndham Newburgh/West Point
2.0 star property
Newburgh
6.2 out of 10, (1,003 reviews)
"Rooms are clean everything was good"
United States
Nancy
The price is ᅣ14,104
ᅣ16,661 total
includes taxes & fees
Jun 28 - Jun 29
Howard Johnson by Wyndham Newburgh/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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Stay near popular Highland attractions

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.

A suspension bridge over a river with hills in the background.
Photo by Allison Alano Flores
Open Photo by Allison Alano Flores

Top Highland Hotel Reviews

More cheap stays in Highland

Frequently asked questions

What's the best place to stay in Highland?
SureStay Plus Hotel by Best Western Highland Poughkeepsie is one of the top choices for your stay based on our traveler data. This hotel offers free breakfast and free parking. Other good options for your stay in the area are Hyatt Place Poughkeepsie / Hudson Valley and Best Western Plus Kingston Hotel And Conference Center. See all available top hotels, or vacation rentals in Highland.
What are some of the best vacation home rentals that Highland has to offer?
The Farm at Hyde Park: This vacation home rental outside of Highland is located in a rural location and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. Kick off your shoes and enjoy yourself with a garden and a selection of games. See all vacation rentals in Highland.
If I need to cancel my hotel reservation in Highland, will I receive a refund?
Yes, the majority of hotel reservations are fully refundable provided that you cancel prior to the accommodation's cancellation deadline, which is often 24 or 48 hours before your scheduled arrival. If you have a reservation that's non-refundable, it may still be possible to cancel it and be given a refund within 24 hours of your booking. Filter your search by fully refundable to find flexible hotel deals in Highland.
Where can I learn more about changing or cancelling my trip to Highland?
For more details about updating your trip to Highland or cancelling it, click here.
What's the best pet-friendly accommodation in Highland?
SureStay Plus Hotel by Best Western Highland Poughkeepsie is a top dog-friendly hotel, and offers laundry facilities along with WiFi for its human guests. See more pet-friendly hotel accommodations in Highland.
Where is the best hotel to stay with easy access to West Park Winery?
Journey Inn Bed & Breakfast is one of the top choices for your stay based on our traveler data, and this 4-star B&B offers free breakfast and free parking. It's located 1.8 mi (2.9 km) from West Park Winery. Other good choices within a few miles include Inn the Woods B&B and Roosevelt Inn of Hyde Park.
What about the best place to stay close to Apple Greens Golf Course?
One of the top choices for your stay is Hampton Inn by Hilton New Paltz, located 1.8 mi (3 km) from Apple Greens Golf Course, and this hotel offers free breakfast and an indoor pool. Rodeway Inn & Suites New Paltz - Hudson Valley and Americas Best Value Inn New Paltz are a couple of other good options within a few miles.
What are some accommodations with pools in Highland?
Hyatt Place Poughkeepsie / Hudson Valley: Offers a snack bar/deli, an indoor pool, and free self parking. Best Western Plus Kingston Hotel And Conference Center and Wildflower Farms, Auberge Collection are a couple of other choices with an onsite pool. View all hotels with pools in Highland.
What's the best hotel for staying near Westchester County Airport (HPN)?
Doral Arrowwood is one of the top choices for your stay and is a popular 4-star hotel featuring a golf course and 2 restaurants. It's located 2 mi (3.3 km) from Westchester County Airport. Other good choices near the airport include Crowne Plaza White Plains - Downtown and La Quinta Inn & Suites by Wyndham Armonk Westchester.
How is it to stay in Highland?
Families enjoy visiting Highland though all visitors are sure to find something to appreciate. Tourists can also enjoy the city's riverfront and mountain views. In Highland, there are 39 hotels and other accommodations to choose from. Find out more about Highland.
What should I see while I'm in Highland?
The picturesque setting of Walkway Over the Hudson State Historic Park and Berean Park Beach exemplify the area's natural beauty. A couple of additional sights to add to your agenda are Franklin D Roosevelt Library & Museum and Apple Greens Golf Course. Check out what more to see and do in Expedia's Highland guide.
What's the seasonal weather like in Highland?
The hottest months are usually July and August with an average temp of 69°F, while the coldest months are January and February with an average of 31°F. The snowiest months in Highland are January, February, March, and April, with each month seeing an average of 7 inches of snowfall.

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