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Our top choices for Highland hotels

Courtyard by Marriott Poughkeepsie

Courtyard by Marriott Poughkeepsie
3.0 star property
Poughkeepsie
8.8 out of 10, Excellent, (1,000 reviews)
"Our room was spotless, and the beds were very comfortable. The staff was very friendly, and the lobby area was beautiful. We’d definitely book again!"
United States
Kayla
The price is CA $176
CA $200 total
includes taxes & fees
May 17 - May 18
Courtyard by Marriott Poughkeepsie

Inn at Bellefield / Hyde Park, Residence Inn by Marriott

Inn at Bellefield / Hyde Park, Residence Inn by Marriott
3.0 star property
Hyde Park
9.6 out of 10, Exceptional, (513 reviews)
"Definitely worth the stay, "
United States
DAVID
The price is CA $259
CA $292 total
includes taxes & fees
May 10 - May 11
Inn at Bellefield / Hyde Park, Residence Inn by Marriott

DoubleTree by Hilton Poughkeepsie Convention Center

DoubleTree by Hilton Poughkeepsie Convention Center
4.0 star property
Downtown Poughkeepsie
8.6 out of 10, Excellent, (1,003 reviews)
"We enjoyed our short stay. Rooms were bice, clean, parking is free and staff is excellent!"
United States
Deanna
The price is CA $144
CA $169 total
includes taxes & fees
May 5 - May 6
DoubleTree by Hilton Poughkeepsie Convention Center

Quality Inn Hyde Park Poughkeepsie North

Quality Inn Hyde Park Poughkeepsie North
2.5 star property
Hyde Park
8.0 out of 10, Very good, (1,008 reviews)
"Room was clean, staff was accommodating and very nice. Parking was convenient, I would stay here again."
United States
Dawn
The price is CA $149
CA $169 total
includes taxes & fees
May 3 - May 4
Quality Inn Hyde Park Poughkeepsie North

The Heartwood

The Heartwood
3.5 star property
Arlington
9.8 out of 10, Exceptional, (262 reviews)
"Great hotel, friendly helpful staff! "
United States
ASHLEY
The price is CA $211
CA $245 total
includes taxes & fees
May 5 - May 6
The Heartwood

Home2 Suites By Hilton Poughkeepsie

Home2 Suites By Hilton Poughkeepsie
3.0 star property
Poughkeepsie
9.4 out of 10, Exceptional, (463 reviews)
"Beautiful spacious rooms and the best gym."
United States
Jane
The price is CA $188
CA $218 total
includes taxes & fees
May 10 - May 11
Home2 Suites By Hilton Poughkeepsie

AutoCamp Catskills

AutoCamp Catskills
5.0 star property
Saugerties
9.0 out of 10, Wonderful, (486 reviews)
"Great stay"
United States
Hitesh
The price is CA $185
CA $261 total
includes taxes & fees
May 14 - May 15
AutoCamp Catskills

Homewood Suites by Hilton Poughkeepsie

Homewood Suites by Hilton Poughkeepsie
3.0 star property
Poughkeepsie
9.6 out of 10, Exceptional, (1,000 reviews)
"Convenient location, safe parking, quiet room with all the comforts. "
United States
Carole
The price is CA $185
CA $215 total
includes taxes & fees
May 25 - May 26
Homewood Suites by Hilton Poughkeepsie

Residence Inn by Marriott Poughkeepsie

Residence Inn by Marriott Poughkeepsie
3.0 star property
Poughkeepsie
8.8 out of 10, Excellent, (653 reviews)
"Spacious suite, all the amenities of a kitchen, lounge area, work space, sleep area and bathroom. Excellent floor plan. Terrific breakfast. I used the gym, but saw many in the pool and hot tub daily. "
United States
Lucia
The price is CA $204
CA $237 total
includes taxes & fees
May 25 - May 26
Residence Inn by Marriott Poughkeepsie

Overlook Lodge at Bear Mountain

Overlook Lodge at Bear Mountain
2.5 star property
Bear Mountain
8.4 out of 10, Very good, (1,000 reviews)
"Beautiful setting and helpful staff. The room was clean and we enjoyed the outdoor activities."
United States
Jen
The price is CA $176
CA $217 total
includes taxes & fees
May 11 - May 12
Overlook Lodge at Bear Mountain

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, (1,002 reviews)
"The place was very clean and the staff was wonderful. Also a very nice breakfast choice included. Would stay there again."
United States
Joanne
The price is CA $127
CA $142 total
includes taxes & fees
May 7 - May 8
SureStay Plus Hotel by Best Western Highland Poughkeepsie

Buttermilk Falls Inn

Buttermilk Falls Inn
3.0 star property
Milton
9.0 out of 10, Wonderful, (44 reviews)
"The room was lovely, clean and comfortable. The resort premises are cute. Breakfast which was included was decent. However, a day before our arrival we have learned that Henry’s restaurant where we had a birthday dinner reservation was closed which was disappointing as it was meant to be part of the overall experience. Tried to reach the property several times, left a voicemail and couple messages through Expedia, no one reached back or acknowledged our outreach. During our stay no one was ever...
United States
Dagmar
The price is CA $548
CA $676 total
includes taxes & fees
May 16 - May 17
Buttermilk Falls Inn

Hampton Inn Harriman Woodbury

Hampton Inn Harriman Woodbury
2.5 star property
Central Valley
9.2 out of 10, Wonderful, (1,095 reviews)
"Clean room, friendly staff, good breakfast!"
United States
Sarah
The price is CA $175
CA $215 total
includes taxes & fees
May 10 - May 11
Hampton Inn Harriman Woodbury

Wildflower Farms, Auberge Collection

Wildflower Farms, Auberge Collection
5.0 star property
Gardiner
9.4 out of 10, Exceptional, (64 reviews)
"This is a beautiful property with a very attentive staff. We enjoyed a wonderful family Christmas trip. Hope to go back soon!"
United States
Blake
The price is CA $1,694
CA $1,971 total
includes taxes & fees
May 26 - May 27
Wildflower Farms, Auberge Collection

Hampton Inn & Suites Poughkeepsie

Hampton Inn & Suites Poughkeepsie
2.5 star property
Crown Heights
9.0 out of 10, Wonderful, (1,004 reviews)
"Great location "
United States
Carla
The price is CA $173
CA $201 total
includes taxes & fees
May 17 - May 18
Hampton Inn & Suites Poughkeepsie

Hampton Inn by Hilton New Paltz

Hampton Inn by Hilton New Paltz
2.5 star property
New Paltz
9.4 out of 10, Exceptional, (1,002 reviews)
"Room was immaculately clean. Staff was very friendly. Just a great stay all around!"
United States
Brigid
The price is CA $201
CA $225 total
includes taxes & fees
May 7 - May 8
Hampton Inn by Hilton New Paltz

Hyatt Place Poughkeepsie / Hudson Valley

Hyatt Place Poughkeepsie / Hudson Valley
3.0 star property
Crown Heights
9.0 out of 10, Wonderful, (1,001 reviews)
"This hotel is very nice. The staff has great customer service. The pool was a little cloudy, but overall our our stay was was enjoyable."
United States
Yanieka
The price is CA $187
CA $218 total
includes taxes & fees
May 18 - May 19
Hyatt Place Poughkeepsie / Hudson Valley

Emerson Resort & Spa

Emerson Resort & Spa
3.5 star property
Mount Tremper
9.2 out of 10, Wonderful, (66 reviews)
"Everything was fantastic!"
United States
Dragana
The price is CA $267
CA $299 total
includes taxes & fees
May 6 - May 7
Emerson Resort & Spa

Woodstock Way Hotel

Woodstock Way Hotel
4.0 star property
Woodstock
9.6 out of 10, Exceptional, (268 reviews)
"Excellent staff and easy check in , parking is very accessible and very close to everything, shops, restaurants and walking trails "
United States
Eladia
The price is CA $367
CA $464 total
includes taxes & fees
May 18 - May 19
Woodstock Way Hotel

Journey Inn Bed & Breakfast

Journey Inn Bed & Breakfast
4.0 star property
Hyde Park
9.6 out of 10, Exceptional, (343 reviews)
"Breakfast was especially delicious and attractive. Very comfortable and hospitable"
United States
Tall
The price is CA $338
CA $383 total
includes taxes & fees
May 3 - May 4
Journey Inn Bed & Breakfast
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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.

Photo by Allison Alano Flores
Open Photo by Allison Alano Flores

Top Highland Hotel Reviews

Recent Reviews in Highland

More cheap stays in Highland

Hotels in Highland with star rating

Find out more about Highland

Top reasons to visit Highland

  • Outdoor Adventures: Highland offers a plethora of activities like skiing and hiking in the stunning Shawangunk Mountains, perfect for adventure seekers.
  • Scenic Beauty: Enjoy picturesque views and serene parks ideal for sunset picnics, showcasing the natural charm of the Hudson Valley.
  • Cultural Experiences: Explore historic bridges and local art galleries that reflect Highland's rich history and vibrant culture.
  • Charming Wineries: Visit local wineries in the renowned wine country for delightful tastings and relaxation.
  • Welcoming Accommodations: Choose from a variety of hotel options, including pet-friendly stays and comfortable rooms for all travellers.

Find great hotels near Highland

Discover an array of hotel accommodations in Highland, New York, tailored to meet diverse needs. From pet-friendly options to comfortable guest rooms ideal for business travel or adventurous getaways, Highland has something for everyone. Popular choices include well-regarded establishments like the Hampton Inn, ensuring a pleasant stay while you explore the scenic beauty of the Hudson Valley.

  • Best Western Fishkill Inn & Suites: A 3.5-star hotel with a commendable guest rating of 8.8, Best Western Fishkill Inn & Suites offers a welcoming and family-friendly atmosphere, making it an ideal choice for travellers seeking both leisure and business accommodations. Located 22.5km from Highland, this hotel features amenities suited for families, including complimentary cribs. Its pet-friendly policy ensures that furry companions are welcome, with specific provisions for pets. The hotel is designed to cater to the needs of diverse guests, providing a comfortable and convenient stay.
  • HYATT house Fishkill/Poughkeepsie: A 3-star hotel that also boasts a guest rating of 8.8, HYATT house Fishkill/Poughkeepsie, situated 22.5km from Highland, is perfect for families and business travellers alike. This hotel promotes a homely experience with its spacious suites, designed to accommodate both relaxation and productivity. Families will appreciate the child-friendly amenities such as cribs and window guards, ensuring safety for younger guests. Pets are welcome, with flexible policies that cater to dog owners, making this an excellent choice for those travelling with animals.
  • Quality Inn & Suites Fishkill South near I-84: A budget-friendly option, the Quality Inn & Suites Fishkill South near I-84 shines with a guest rating of 9.0. Located 22.5km from Highland, this hotel is tailored for family and business travellers with its affordable yet comfortable accommodations. The property includes amenities like complimentary cribs and window guards for children, ensuring a safe environment for families. This hotel prioritizes guest satisfaction while providing great value, making it a wise choice for budget-conscious visitors.

Where to stay near Highland

Highland, New York, offers a delightful mix of outdoor adventures and scenic beauty, perfect for a memorable vacation. Explore the breathtaking Shawangunk Mountains for hiking and stunning views, or unwind in the charming local wineries of the renowned wine country. With its family-friendly atmosphere and friendly locals, Highland is an ideal destination for relaxation and exploration. Don’t miss the nearby shops and vibrant communities that add to the delightful experience of upstate New York.

  • Poughkeepsie: Located a mere 3.2km from Highland, Poughkeepsie is a vibrant city that offers a variety of outdoor and family-friendly adventures. The city sees a steady stream of visitors year-round, with peak times in the summer months of July and August, as well as October. Here, you can explore educational institutions, shopping areas, and recreational facilities. Notable landmarks include a modern college university and a picturesque lake, making it a perfect spot for both relaxation and exploration.
  • New Paltz: Just 11.3km from Highland, New Paltz is a charming city known for its stunning natural beauty and adventurous spirit. Visitors flock here, particularly in April and during the late summer to fall months. Outdoor enthusiasts will love the recreational areas and ski fields that surround the town. Key attractions include serene lakes, a nature reserve, and majestic mountains, creating an idyllic backdrop for hiking and outdoor activities.
  • Hudson Valley: Situated 16.1km from Highland, Hudson Valley is a picturesque region celebrated for its breathtaking scenery and adventurous offerings. The area garners attention from travellers during the summer and fall, with popular activities including skiing at local resorts. Visitors can enjoy beautiful lakes, towering mountains, and even a beach, making it a versatile destination for anyone seeking outdoor fun and relaxation in a stunning setting.

Things to do in Highland

Highland, New York, is perfect for outdoor enthusiasts seeking adventure and stunning scenery. Enjoy a variety of activities, including skiing and exploring local ski fields. For a more relaxed experience, partake in sunset picnics at serene parks, visit art galleries, or explore the vibrant nightlife and entertainment options that showcase the area's charm. Whether you're seeking thrills or tranquility, Highland offers something for everyone.

Shopping

In Highland, you can explore local shops and boutiques for unique gifts and souvenirs. If you're up for a drive, visit the Poughkeepsie Galleria, about 22.5km away, featuring a mix of popular retailers and dining options for a full shopping experience.

Recreation

In Highland, the Mohonk Mountain House offers rejuvenating spa treatments surrounded by breathtaking views. Nearby, you can explore the tranquil grounds and partake in yoga sessions, while the nearby Hudson Valley boasts hiking trails that invigorate both body and mind, perfect for reconnecting with nature.

Adventure

Experience the stunning trails of the Walkway Over the Hudson, a scenic bridge offering breathtaking views of the Hudson River. For more thrill, explore the nearby Minnewaska State Park Preserve, where you can hike, rock climb, and discover beautiful waterfalls amidst the captivating landscapes.

Nightlife

Highland offers a charming nightlife with cozy spots like The Hudson Valley Brewery, where you can enjoy craft brews, or the lively atmosphere at The Country Club, perfect for unwinding with friends over a drink. Don't miss the local music scene for a taste of local talent.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Booking tips and Expedia advantages for Highland

  • The most and least expensive months on average to stay in a hotel: The cheapest months to stay in Highland are January to March, where the prices are slightly lower. This is in comparison to August to October, where prices are slightly higher.
  • The most and least expensive days on average to stay in a hotel: The least expensive day to stay in Highland is Tuesday. The most expensive day to stay in Highland is Saturday.
  • Find cheap hotels on Expedia: Utilize Expedia’s search tool to refine your preferences such as budget, desired location, and type of accommodation. For instance, selecting the Eco-certified filter will showcase sustainable and environmentally friendly hotels that are currently available. To find the best prices and offers, arrange the price filter from lowest to highest.
  • Consider bundling your trip: You can save money by combining your hotel stay in the Highlands with your flights and activities through an Expedia package deal.

Find the best attractions in and around Highland

Highland, New York, is perfect for outdoor and adventure seekers, offering stunning scenery and cultural experiences. Visitors can explore historic bridges, sites, and houses that reflect the region's rich history. Additionally, the nearby Hudson Valley enhances the experience with beautiful landscapes and recreational activities, making it an ideal destination for those looking to immerse themselves in nature and local culture.

  • Franklin D Roosevelt Library & Museum: Immerse yourself in the rich history and legacy of Franklin D. Roosevelt at this library and museum. With its cultural exhibits and family-friendly atmosphere, it's a great spot to learn about the life and presidency of one of America's most significant leaders.
  • Mohonk Lake: Just 17.7km from Highland, Mohonk Lake offers stunning outdoor activities, romantic settings, and picturesque scenery. Enjoy a relaxing day at the beach or explore hiking trails that wind through the beautiful landscape.
  • Walkway Over the Hudson State Historic Park: Located only 1.4km from Highland, this historic bridge provides breathtaking views of the Hudson River. Stroll along the elevated walkway and take in the cultural significance of this remarkable landmark.

Best time to go to Highland

The best time to visit Highland can depend on the weather and when visitor numbers rise and fall. The hottest average temperature in Highland falls in July, when visitor numbers are moderately high and weather is mostly sunny with light rain. The coolest average temperature in Highland falls in January, visitor numbers are moderately low and weather is mostly sunny with light rain.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January26.8°F (-2.9°C)Light RainMostly SunnyModerately LowSlightly Low
February28.6°F (-1.9°C)Light RainMostly SunnyAverageSlightly Low
March36.3°F (2.4°C)Light RainMostly SunnyModerately HighSlightly Low
April48.0°F (8.9°C)Light RainMostly SunnyModerately HighAverage
May59.2°F (15.1°C)Light RainMostly SunnyAverageAverage
June67.1°F (19.5°C)Light RainMostly SunnyAverageAverage
July73.2°F (22.9°C)Light RainMostly SunnyModerately HighAverage
August71.1°F (21.7°C)Light RainMostly SunnyAverageSlightly High
September64.0°F (17.8°C)Light RainMostly SunnyAverageSlightly High
October52.9°F (11.6°C)Light RainMostly SunnyAverageSlightly High
November40.6°F (4.8°C)Light RainMostly SunnyModerately LowAverage
December32.7°F (0.4°C)Light RainMostly SunnyModerately LowAverage

The nearest major airports for your trip to Highland

For your trip to Highland, New York, the closest major airports are New York's JFK, Newark Liberty Intl. (EWR), and LaGuardia (LGA). JFK is approximately 120.7km away and offers luxurious accommodations like Arlo Williamsburg and The William Vale, both 17.7km from the airport. Newark Liberty Intl. is about 115.9km from Highland, with top hotels such as The Dominick and Four Seasons Hotel New York Downtown, both 14.5km from the airport. LaGuardia is around 106.2km away, featuring elegant options like The Plaza and The Pierre, both just 8.0km from the airport, providing scheduled transportation services for convenience.

Frequently asked questions

What is the best area to stay in Highland?
The best area to stay in Highland is near the Walkway Over the Hudson, particularly along the eastern bank of the Hudson River.

This area is Highland's main attraction, offering direct access to the Walkway, a pedestrian bridge spanning the Hudson River. You'll find a selection of hotels and B&Bs in close proximity, making it easy to start your day with a scenic walk or cycle. The streets here are generally quiet, with some local eateries and shops dotted along Route 9W as it passes through the town.

For couples, staying near the Walkway Over the Hudson is ideal. You can enjoy romantic strolls with panoramic river views, especially at sunrise or sunset. Many accommodations in this area offer comfortable settings, some with views of the river, superb for a relaxing getaway.

Solo travellers will also appreciate the convenience of this location. It provides easy access to the Walkway for outdoor activities, and there are a few local cafes and restaurants where you can enjoy a meal or a coffee.
What are the best hotels in Highland that travellers recommend?
For a highly recommended hotel in Highland, consider the SureStay Plus Hotel by Best Western Highland Poughkeepsie.

This hotel, rated 7.8, offers comfortable and clean rooms with air conditioning. Guests often praise the great and amazing staff, and the comfortable beds. It provides a complimentary continental breakfast and has kitchen facilities in some rooms, which is convenient for longer stays. The hotel also offers early check-in for an additional charge.
What are the best family hotels in Highland?
When looking for family-friendly accommodation in Highland, the SureStay Plus Hotel by Best Western Highland Poughkeepsie is a good option.

The SureStay Plus Hotel by Best Western Highland Poughkeepsie, rated 7.8, offers convenient amenities such as connecting rooms, which are ideal for families. Guests appreciate the complimentary continental breakfast, making mornings easier with children. Many reviews highlight the comfortable and clean rooms, as well as the great customer service from the staff. Find more child-friendly accommodations in Highland
What hotels in Highland offer free breakfast?
For hotels in Highland that offer free breakfast, the SureStay Plus Hotel by Best Western Highland Poughkeepsie is a great choice.

This hotel, with a 7.8 rating, provides a complimentary continental breakfast daily, ensuring a convenient start to your day. Guests frequently mention the comfortable and clean rooms, as well as the great and amazing staff. Free self-parking is also available, which is a useful amenity. Find more hotels with free breakfast in Highland
What are the top pet-friendly hotels in Highland?
For a top pet-friendly hotel in Highland, consider the SureStay Plus Hotel by Best Western Highland Poughkeepsie.

This hotel, with a 7.8 rating, is a welcoming choice for travellers with pets. Guests often mention the comfortable and clean rooms, as well as the great and amazing staff. The beds are noted for being comfortable, and the customer service is consistently praised. The lobby is also described as lovely. The hotel is conveniently located approximately 102 km from the Hudson River. See more pet-friendly hotels in Highland
What are the best budget hotels in Highland?
For an excellent budget-friendly option in Highland, consider the SureStay Plus Hotel by Best Western Highland Poughkeepsie.

This hotel, with a 7.8 rating, is much-loved by guests for its comfortable and clean rooms, as well as its great and amazing staff and customer service. Travellers particularly appreciate the comfortable beds. Guests also benefit from complimentary breakfast, free toiletries, and free self-parking, including space for RVs, buses, and trucks. The hotel's lobby is known for being lovely. While the Hudson River is a bit of a drive away, the hotel provides a solid base for exploring the area. View all budget hotels in Highland
When is the best time to go to Highland?
The best time to go to Highland, New York, is generally from late spring to early autumn, specifically May through October, for pleasant weather and a wide range of outdoor activities.

During these months, the weather is typically mild and sunny, making it ideal for exploring the Walkway Over the Hudson State Historic Park, a former railway bridge converted into a pedestrian path offering panoramic views of the Hudson River. This period also allows for comfortable hiking and cycling on the various trails in the surrounding Hudson Valley.

Couples looking for a romantic getaway will find May, June, September, and October particularly appealing. The blossoming trees in spring and the vibrant foliage in autumn create a picturesque backdrop for wine tasting tours at local vineyards or leisurely strolls through charming small towns nearby. The cooler temperatures in these shoulder months are also more comfortable for outdoor dining and evening walks.

Families travelling with children will likely prefer July and August. The warmer weather is superb for enjoying water-based activities on the Hudson River, such as kayaking or boat tours.
Can I cancel my hotel reservation on Expedia?
You can cancel your hotel reservation on Expedia, though it depends on the cancellation policy of your booking. Most bookings are refundable if canceled within 24-48 hours of the scheduled arrival. Be sure to check your booking confirmation for the exact cancellation policy. If free cancellation is available, you can cancel directly through your Expedia account by logging in, going to "My Trips", and selecting your reservation. To find flexible deals, filter your search by "Fully refundable property" for hotels in Highland.
How can I save on a Highland hotel booking with Expedia?
Members always get our best prices. Find our best Highland hotel deals by joining Expedia's free travel rewards program today. As a member, you can unlock instant savings and member perks when you're logged in to your account. Another tip is to book your hotel and flights together on Expedia, where bundling can result in significant savings.
How much is the nightly rate at a Highland hotel?
Prices for hotels in Highland often vary, but you can find a great deal from CA $104 on Expedia. All sorts of factors affect price, such as the time of year or the days of the week you choose for your stay. Find the best deals by being flexible with your dates, and sort search results by "Price: low to high" for the cheapest rate.

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