A suspension bridge over a river with autumn foliage and distant hills.

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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 £71
includes taxes & fees
1 Jul - 2 Jul
SureStay Plus Hotel by Best Western Highland Poughkeepsie

Tin Brook Bed & Breakfast

Tin Brook Bed & Breakfast
3.0 star property
Walden
9.4 out of 10, Exceptional, (123 reviews)
"Very nice accommodations & staff."
United States
Laurie
The price is £89
includes taxes & fees
28 Jun - 29 Jun
Tin Brook Bed & Breakfast

The Harlow House

The Harlow House
2.0 star property
Rhinebeck
10.0 out of 10, Exceptional, (5 reviews)
"Carrie the owner was a star 10 out of 10. the property, the house and the suite were amazing, beautiful and the surrounding woods so tranquil. already looking forward to coming back for another stay."
United States
Robert
The price is £175
includes taxes & fees
29 Jun - 30 Jun
The Harlow House

Stonehill's Farmhouse

Stonehill's Farmhouse
3.5 star property
Accord
9.2 out of 10, Wonderful, (57 reviews)
"Really lovely place, we stayed in the deluxe cabin "
United States
etgar
The price is £126
includes taxes & fees
28 Jun - 29 Jun
Stonehill's Farmhouse

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 £96
includes taxes & fees
29 Jun - 30 Jun
Borland House Inn

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 £99
includes taxes & fees
8 Jul - 9 Jul
Americas Best Value Inn New Paltz

Rhinecliff Hotel

Rhinecliff Hotel
2.0 star property
Rhinecliff
10.0 out of 10, Exceptional, (8 reviews)
"Hotel reopened two days prior to our stay. Barry, the property owner, greeted us upon our arrival and explained that there was everything we may need in the lobby: coffee, tea, water, snacks etc. Our room and king sized bed was very comfortable. Loved the bathroom with free standing soaking tub. The view of the Hudson River from our balcony was spectacular. Wish we had a clearer night to see sunset over the Hudson. We would definitely stay there again and would highly recommend to friends and...
United States
Diane
The price is £135
includes taxes & fees
29 Jun - 30 Jun
Rhinecliff Hotel

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 £66
includes taxes & fees
29 Jun - 30 Jun
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 £97
includes taxes & fees
5 Jul - 6 Jul
Best Western Plus The Inn & Suites At The Falls

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 £89
includes taxes & fees
26 Jul - 27 Jul
Holiday Inn Express & Suites Montgomery by IHG

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 £89
includes taxes & fees
26 Jul - 27 Jul
Quality Inn & Suites Fishkill South near I-84

Cadet Motel

Cadet Motel
2.0 star property
Cornwall
6.4 out of 10, (311 reviews)
"great stay !"
United States
reagan
The price is £76
includes taxes & fees
30 Jun - 1 Jul
Cadet Motel

The Wiltwyck

The Wiltwyck
3.5 star property
Kingston
9.4 out of 10, Exceptional, (199 reviews)
"Beautiful property"
United States
Scott
The price is £157
includes taxes & fees
30 Jun - 1 Jul
The Wiltwyck

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 £88
includes taxes & fees
19 Jul - 20 Jul
Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point

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 £64
includes taxes & fees
30 Jun - 1 Jul
Ramada by Wyndham Newburgh/West Point

Jenny's Country Manor

Jenny's Country Manor
2.0 star property
Red Hook
7.6 out of 10, Good, (133 reviews)
"Very nice staff! Large rooms, convenient location."
United States
Georgi
The price is £120
includes taxes & fees
28 Jun - 29 Jun
Jenny's Country Manor

The Lagrange Inn & Extended Stay

The Lagrange Inn & Extended Stay
2.0 star property
Pleasant Valley
9.2 out of 10, Wonderful, (15 reviews)
"Room was clean, spacious, and staff was amazing. "
United States
Greg
The price is £98
includes taxes & fees
28 Jun - 29 Jun
The Lagrange Inn & Extended Stay

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 £79
includes taxes & fees
12 Jul - 13 Jul
Super 8 by Wyndham Kingston

Village Motel

Village Motel
2.0 star property
Ellenville
6.8 out of 10, (218 reviews)
"Great staff, clean. "
United States
Joline
The price is £72
includes taxes & fees
28 Jun - 29 Jun
Village Motel

West Point Motel

West Point Motel
2.5 star property
Highland Falls
8.6 out of 10, Excellent, (716 reviews)
The price is £112
includes taxes & fees
13 Jul - 14 Jul
West Point Motel
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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

Find out more about Highland

Top reasons to visit Highland

  • Outdoor Adventures: Highland is an excellent destination for outdoor enthusiasts, offering activities like hiking, skiing, and exploring scenic landscapes.
  • Rich Local Culture: Visitors can discover historical sites and modern colleges that showcase the unique culture of the area.
  • Family-Friendly Atmosphere: With various attractions and recreational areas, Highland is perfect for family holidays.
  • Charming Accommodations: A range of delightful lodging options, from pet-friendly stays to agritourism properties, cater to all travellers.
  • Scenic Hudson Valley: Nestled in the picturesque Hudson Valley, Highland offers a relaxing vibe and beautiful surroundings.

Find great hotels near Highland

Discover a range of delightful hotel accommodations in Highland, New York, catering to every type of traveller. Whether you're seeking a pet-friendly retreat, a business-focused stay, or an adventure-filled getaway, you'll find a variety of options to suit your needs. From charming agritourism properties to top-rated hotels, Highland promises a memorable experience for all visitors.

  • Best Western Fishkill Inn & Suites: This 3.5-star hotel offers a welcoming atmosphere ideal for families and business travellers alike, located 8.7km from Highland. Best Western Fishkill Inn & Suites is particularly beloved for its pet-friendly policy, making it a great choice for those travelling with furry companions. The hotel features comprehensive business amenities, including a 24-hour business centre, meeting rooms, and conference space, ensuring a productive stay. Families can enjoy conveniences such as free cribs for little ones, while pets are accommodated with specific restrictions. With its blend of comfort and practicality, it’s perfect for a diverse range of guests.
  • HYATT house Fishkill/Poughkeepsie: Situated also 8.7km from Highland, the 3-star HYATT house Fishkill/Poughkeepsie is designed for both family vacations and business trips. This hotel prides itself on being pet-friendly, welcoming both dogs and cats with certain fees. Business travellers will find multiple meeting rooms and conference spaces, alongside a fully equipped business centre. Families are catered for with free cribs, window guards, and a first-aid kit for peace of mind. With a focus on comfort and functionality, this hotel ensures a relaxing stay for all types of travellers.
  • Quality Inn & Suites Fishkill South near I-84: This hotel, located 8.7km from Highland, stands out for its commitment to inclusivity, being LGBTQIA welcoming and affiliated with LGBTQI travel guides. It offers essential business amenities such as meeting rooms and conference space, making it suitable for corporate stays. Families will appreciate the provision of free cribs and window guards to ensure safety for children. With a friendly atmosphere and a focus on diverse needs, Quality Inn & Suites provides a welcoming retreat for all visitors.

Where to stay near Highland

Highland, New York, offers a delightful blend of outdoor adventures and family-friendly experiences. Nestled in the scenic Hudson Valley, this charming town serves as a convenient base to explore the beauty of New England. Visitors can immerse themselves in the sunny weather while enjoying the warm atmosphere created by friendly locals. With picturesque landscapes and a relaxing vibe, Highland is perfect for those seeking both adventure and tranquillity during their vacation.

  • Poughkeepsie: Located a mere 1.2km from Highland, Poughkeepsie is a vibrant city that attracts visitors year-round. While the peak seasons are July to August and October, the city boasts a wealth of outdoor and family-friendly activities. Notable highlights include a charming shopping area and a picturesque lake surrounded by mountains. The presence of a modern college university adds an educational flair, making Poughkeepsie a perfect blend of urban and natural experiences.
  • New Paltz: Situated 4.3km from Highland, New Paltz is a haven for outdoor enthusiasts and adventure seekers. With its peak visitor numbers in April and from August to September, this city is renowned for its stunning scenery and recreational areas. Popular activities include skiing at local ski fields, while nearby lakes and nature reserves offer breathtaking views and ample opportunities for exploration. New Paltz is an ideal destination for those looking to immerse themselves in nature’s beauty.
  • Hyde Park: Just 2.5km from Highland, Hyde Park is a culturally rich city that thrives on outdoor family experiences. It welcomes tourists predominantly in June to July and September. Visitors can enjoy educational attractions, shopping areas, and skiing opportunities. The city is home to significant landmarks, including historic and modern college universities, as well as peaceful lakes. Hyde Park is a delightful mix of culture and nature, making it a must-visit destination.

Things to do in and around Highland

Highland offers a delightful blend of outdoor and adventure activities perfect for family holidays. Visitors can explore educational attractions, enjoy skiing opportunities, and unwind in recreational areas. With its scenic landscapes and various activities, Highland is an excellent destination for those seeking both relaxation and adventure.

Shopping

For a delightful shopping experience in Highland, visit the Poughkeepsie Galleria, just 4.3km away, offering a variety of shops and entertainment. If you're up for a drive, the Hudson Valley Mall (14.3km away) and Stormville Airport Antique Show & Flea Market (9.3km away) provide unique finds and local charm.

Recreation

Apple Greens Golf Course offers an invigorating outdoor experience with its scenic fairways, perfect for a relaxing day of golf. For a tranquil vibe, visit Richard L. Skimin Memorial Baseball Field, where you can unwind in a peaceful park setting. Enjoy laughter and family fun at Bananas Comedy Club, a delightful entertainment venue.

Adventure

At Paintball Sports, located 4.3km from Highland, unleash your competitive spirit in an exhilarating paintball battle. North Landing Beach, also 4.3km away, offers a family-friendly campground perfect for adventurous outdoor activities. For breathtaking scenery, trek the Labyrinth Trailhead, situated 6.8km from Highland.

Nightlife

A vibrant evening in Highland awaits with a visit to the Chance Theater for a dose of culture and entertainment, just 1.2km away. Alternatively, enjoy a nostalgic film at the Overlook Drive-In Theater, 3.1km from town, or unleash your inner child at Fun Central, 5.6km away.

Booking tips and Expedia advantages for Highland

To save money on your trip to Highland, visit between January and March for lower accommodation rates, avoiding the pricier August to October period. Booking a stay on a Tuesday will also help you find better deals compared to Saturdays. Utilise Expedia to filter hotels by budget and location, and consider eco-certified options for sustainable stays. Combine your hotel, flights, and activities for potential savings with package deals. Don't forget to explore free local activities to enhance your experience without breaking the bank.

  • 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: Utilise Expedia's search tool to refine your preferences, such as budget, preferred location, and the type of hotel you desire. For instance, selecting the Eco-certified filter will showcase sustainable and environmentally friendly hotels currently available. To discover the most affordable prices and offers, arrange the price filter from lowest to highest.
  • Consider bundling your trip: You can potentially save money by combining your Highland hotel reservation with your flights and activities through an Expedia package.

Find the best attractions near Highland

Highland, New York, is an ideal destination for outdoor enthusiasts and families seeking adventure. Visitors can explore a variety of attractions, including modern colleges, historic bridges, and significant sites that showcase the local culture. Whether you're after thrilling outdoor experiences or enriching historical insights, Highland offers a diverse range of points of interest to make your holiday memorable.

  • Culinary Institute of America: Located a mere 1.2km from Highland, this esteemed institution offers a unique blend of culinary excellence and rich history. Visitors can enjoy exquisite dining experiences prepared by students and explore the vibrant atmosphere of culinary arts.
  • Vassar College: Situated 2.5km away, this modern college boasts stunning architecture and beautiful grounds. Known for its vibrant campus life, Vassar offers a refreshing city vibe, making it a great spot to stroll and soak in the academic environment.
  • Home of Franklin D. Roosevelt National Historic Site: Also 2.5km from Highland, this historic site provides an insightful glimpse into the life of America’s 32nd president. The picturesque grounds and museum evoke a deep cultural appreciation and historical significance.

Best time to go to Highland

The best time to visit Highland is dependant on what kind of holiday you are seeking. July is its hottest month on average. At this time, visitor numbers are moderately high and weather is mostly sunny with light rain. January is its coolest month on average. At this time, 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 SunnyAverageSlightly High
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 SunnyAverageAverage
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 visit to Highland, New York, you have several airport options. White Plains, NY (HPN-Westchester County) is 29.2km away, with nearby hotels such as The Opus Westchester and Sonesta White Plains, both 2.5km from the airport, offering complimentary airport transfers. Newburgh, NY (SWF-Stewart Intl.) is only 10.6km from Highland, with good options like The Dutchess Inn and Spa at Beacon, located 3.7km away. Lastly, Danbury, CT (DXR-Danbury Municipal) is 32.5km away, featuring hotels like Hotel Zero Degrees Danbury, just 1.2km from the airport. Each airport is accessible from these hotels, making your travel convenient.

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.
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.
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.
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.
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 £64 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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