Search Highland hotels

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Filter by

Guest rating
Guest rating
Star rating

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, (960 reviews)
  • cleanliness
    Stay near Vassar College with complimentary breakfast and self-parking.
"Super clean! Hotel manager along with all other employees were pleasant and helpful. "
United States
Ana
The price is NZ$132
includes taxes & fees
19 Feb - 20 Feb
SureStay Plus Hotel by Best Western Highland Poughkeepsie

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)
  • cleanliness
    Stay close to campus in New Paltz, where trails meet modern comfort and convenience.
"Very kind and courteous staff, very clean rooms. "
United States
John
The price is NZ$160
includes taxes & fees
16 Feb - 17 Feb
Americas Best Value Inn New Paltz

Borland House Inn

Borland House Inn
3.0 star property
Montgomery
9.2 out of 10, Wonderful, (150 reviews)
  • cleanliness
    Experience Victorian elegance at a B&B with facials and garden dining options.
"Breakfast was hot and tasty. Staff were all pleasant and accommodating. "
United States
wendy
Borland House Inn

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, (444 reviews)
"Nice and quaint hotel with beautiful creek behind surrounded by a dorest"
United States
Hiram
The price is NZ$163
includes taxes & fees
15 Feb - 16 Feb
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, (823 reviews)
  • cleanliness
    Unwind near City Winery in Montgomery with a complimentary hot breakfast.
"The staff was great! The room was clean and the breakfast was excellent."
Canada
Joey
The price is NZ$165
includes taxes & fees
22 Feb - 23 Feb
Holiday Inn Express & Suites Montgomery by IHG

West Point Motel

West Point Motel
2.5 star property
Highland Falls
8.6 out of 10, Excellent, (672 reviews)
  • cleanliness
    Just minutes from Bear Mountain State Park and US Military Academy attractions.
"Always a great stay. Easy access to West Point. Clean. It’s a great simple stay for your cadet to get off base for a day or two. "
United States
Stephanie
The price is NZ$187
includes taxes & fees
1 Mar - 2 Mar
West Point Motel

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, (1,003 reviews)
  • cleanliness
    Unwind near Stewart Airport with a complimentary shuttle and indoor pool.
"Clean room, friendly staff"
United States
KAREN
The price is NZ$180
includes taxes & fees
15 Feb - 16 Feb
Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point

Spark by Hilton Fishkill

Spark by Hilton Fishkill
3.0 star property
Fishkill
7.6 out of 10, Good, (25 reviews)
"Room was clean, check-in was easy."
United States
Maureen
The price is NZ$168
includes taxes & fees
20 Feb - 21 Feb
Spark by Hilton Fishkill

Hampton Inn & Suites Poughkeepsie

Hampton Inn & Suites Poughkeepsie
2.5 star property
Crown Heights
9.0 out of 10, Wonderful, (1,004 reviews)
  • cleanliness
    Convenient Poughkeepsie hotel near Vassar College with complimentary amenities.
"Best staff ever great location."
United States
Rafael
The price is NZ$172
includes taxes & fees
28 Feb - 1 Mar
Hampton Inn & Suites Poughkeepsie

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, (1,002 reviews)
  • cleanliness
    Enjoy a complimentary breakfast and fitness centre at this Fishkill train station hotel.
"Room was cleaned and staff was friendly. "
United States
Giovanni
The price is NZ$164
includes taxes & fees
1 Mar - 2 Mar
Quality Inn & Suites Fishkill South near I-84

The Wiltwyck

The Wiltwyck
3.5 star property
Kingston
9.4 out of 10, Exceptional, (171 reviews)
  • cleanliness
    Unwind in charming Kingston guesthouse near historic sites and outdoor trails.
"Great stay! Well decorated and a beautiful building walking distance from shops restos and the beautiful downtown. The host was waiting to greet us even though we were quite late to check in. Would stay again!"
United States
Ema
The Wiltwyck

Peaceful Lakeside Studio Fast Wifi Great WFH

Peaceful Lakeside Studio Fast Wifi Great WFH
2.0 star property
Monroe
The price is NZ$577
includes taxes & fees
16 Feb - 17 Feb
Peaceful Lakeside Studio Fast Wifi Great WFH

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, (467 reviews)
  • cleanliness
    Modern Hyde Park hotel with free breakfast and convenient location near attractions.
"Clean room, comfy bed, amazing breakfast buffet. "
United States
Mimi
The price is NZ$270
includes taxes & fees
23 Feb - 24 Feb
Inn at Bellefield / Hyde Park, Residence Inn by Marriott

Hyatt Place Poughkeepsie / Hudson Valley

Hyatt Place Poughkeepsie / Hudson Valley
3.0 star property
Crown Heights
9.0 out of 10, Wonderful, (1,002 reviews)
"Room was very clean and the staff was very nice!"
United States
Kareem
The price is NZ$194
includes taxes & fees
23 Feb - 24 Feb
Hyatt Place Poughkeepsie / Hudson Valley

Rhinebeck Village Inn

Rhinebeck Village Inn
2.0 star property
Rhinebeck Village
7.6 out of 10, Good, (394 reviews)
"Wonderful destination!"
United States
candice
The price is NZ$197
includes taxes & fees
20 Feb - 21 Feb
Rhinebeck Village Inn

Cadet Motel

Cadet Motel
2.0 star property
Cornwall
6.4 out of 10, (306 reviews)
"Easy to spot on the road and helpful friendly staff"
United States
Alex
The price is NZ$155
includes taxes & fees
19 Feb - 20 Feb
Cadet Motel

Hudson Valley 9w Motel

Hudson Valley 9w Motel
2.0 star property
Lake Katrine
8.2 out of 10, Very good, (68 reviews)
  • cleanliness
    Relax by scenic Hudson Valley with nearby shopping and park attractions.
"easy check in, great location. perfect for a couple going away overnight just needing a place to crash "
United States
donna
The price is NZ$259
includes taxes & fees
23 Feb - 24 Feb
Hudson Valley 9w Motel

Jenny's Country Manor

Jenny's Country Manor
2.0 star property
Red Hook
7.6 out of 10, Good, (133 reviews)
  • cleanliness
    Cosy retreat in Red Hook with free WiFi and parking near Lake Carvel.
"Very nice staff! Large rooms, convenient location."
United States
Georgi
The price is NZ$262
includes taxes & fees
11 Mar - 12 Mar
Jenny's Country Manor

Village Motel

Village Motel
2.0 star property
Ellenville
6.6 out of 10, (208 reviews)
  • cleanliness
    Tranquil Ellenville retreat near Shadowland Theatre with free parking and WiFi.
"Check in process was fine, staff was pleasant. Room was in worse shape than the pictures & smelled like stale cigarette smoke. I get that it was an inexpensive room, but won’t be back. "
United States
Matthew
The price is NZ$147
includes taxes & fees
18 Feb - 19 Feb
Village Motel

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, (1,000 reviews)
  • cleanliness
    Step away from ordinary stays at this Hudson Valley hotel near FDR's library.
"Comfortable hotel and staff very welcoming "
United States
Sunil
The price is NZ$150
includes taxes & fees
1 Mar - 2 Mar
Quality Inn Hyde Park Poughkeepsie North
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.

The Annual Holiday Sale

Members save up to 40% on hotels and homes. Plan this year’s big trip and save.
Save an average of 15% on thousands of hotels when you're signed in

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.

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

More cheap accommodation in Highland

Find out more about Highland

Top reasons to visit Highland

  • Outdoor Adventures: Highland provides ample opportunities for hill walking and exploring scenic trails, perfect for nature lovers.
  • Wine Tastings: Enjoy local vineyards and experience delightful wine tastings in the beautiful Hudson Valley.
  • Rich Scottish Heritage: Discover the area's unique Scottish influence, showcased in local culture and attractions.
  • Family-Friendly Activities: Visit nearby theme parks and charming spots for enjoyable family outings.
  • Diverse Accommodation: Find a variety of lodging options, from pet-friendly hotels to agritourism experiences.

Find great hotels near Highland

Discover a range of accommodation options in Highland, New York, perfect for every type of traveller. Whether you're seeking a pet-friendly hotel, an agritourism experience, or a business-themed stay, Highland offers a variety of choices to suit your needs. Enjoy the unique adventure vacation experiences available while relaxing in comfortable lodgings that make your visit memorable.

  • Best Western Fishkill Inn & Suites: Located 22.5km from Highland, this 3.5-star hotel combines comfort and inclusivity, making it an ideal choice for families and LGBTQIA travellers. With a focus on a welcoming atmosphere, the property features amenities designed for children, including complimentary cribs. Pet-friendly policies allow for dogs with certain restrictions, ensuring that your furry friends can join the adventure. The hotel embraces a family-oriented vibe, providing a safe and enjoyable experience for all guests.
  • HYATT house Fishkill/Poughkeepsie: Also situated 22.5km from Highland, this 3-star hotel caters to business travellers and families alike. It offers a range of business amenities, including multiple meeting rooms and a fully-equipped business centre, making it a convenient choice for professionals. The hotel is also family-friendly, with features such as first aid kits and childproofing measures in place. Dogs and cats are welcome, ensuring that your pets can accompany you on your journey while you enjoy the comfortable accommodations.
  • Quality Inn & Suites Fishkill South near I-84: This hotel, located 22.5km from Highland, provides a blend of business functionality and family-friendly amenities. With facilities such as a business centre and conference space, it’s well-suited for corporate guests. The property is also LGBTQIA welcoming and features amenities for children, including window guards and cribs. Guests appreciate the inclusive atmosphere and the convenience of being close to local attractions while enjoying a comfortable stay.

Where to stay near Highland

Highland, New York, offers an idyllic escape for outdoor enthusiasts and families alike. With its stunning scenic beauty and friendly atmosphere, visitors can explore the charming city and nearby regions, basking in sunny weather and breathtaking views. Don't miss the chance to experience the local culture and the warmth of the community, making it a perfect spot for relaxation and adventure in the heart of the New York countryside.

  • Poughkeepsie: Situated a mere 3.2km from Highland, Poughkeepsie is a vibrant city that offers a delightful mix of outdoor, family, and urban experiences. The city attracts visitors year-round, with peak travel times in July to August and October. Here, you can enjoy a wealth of activities, including education and shopping at local centres. Notable landmarks such as a modern college, nearby lakes, and scenic mountains enhance the city's charm, making it an ideal stop for those looking to explore a blend of culture and nature.
  • New Paltz: Located 11.3km from Highland, New Paltz is an outdoor enthusiast's paradise, famed for its adventurous spirit and stunning scenery. The city welcomes visitors primarily in April and from August to September, making it a perfect destination for those seeking recreational pursuits. With ski fields and nature reserves in the vicinity, New Paltz is ideal for a range of activities, from skiing to hiking. Its picturesque lakes and majestic mountains provide breathtaking backdrops, ensuring an unforgettable experience for every traveller.
  • Hyde Park: Just 6.4km from Highland, Hyde Park is a family-friendly city rich in culture and outdoor activities. Visitors flock to this area from June to July and September, looking for a blend of education, shopping, and recreational opportunities. The city is home to historic and modern colleges, and its proximity to beautiful lakes adds to its appeal. Hyde Park is perfect for those wishing to immerse themselves in a community that celebrates both history and nature.

Things to do in and around Highland

Highland, New York, is perfect for outdoor and family adventures, offering activities like hill walking, wine tastings, and various itineraries for exploring the area. Visitors can enjoy scenic walks, relax in recreational areas, and visit nearby theme parks for fun-filled days. Whether you're seeking an educational experience or thrilling outdoor pursuits, Highland has something to offer for everyone.

Shopping

For shopping in Highland, visit Poughkeepsie Galleria, a vibrant centre just 11.3km away, offering a mix of entertainment and family-friendly vibes. If you're up for a drive, check out the Hudson Valley Mall, 111.3km away, for more shopping options and lively atmosphere.

Recreation

Apple Greens Golf Course offers a relaxing outdoor experience with scenic views and well-maintained greens, perfect for a round of golf. Nearby, Richard L. Skimin Memorial Baseball Field provides a tranquil park atmosphere ideal for unwinding. For a dose of laughter, visit Bananas Comedy Club, which promises family-friendly entertainment.

Adventure

North Landing Beach, a charming campground 11.3km from Highland, offers thrilling outdoor adventures and a perfect family getaway. For an adrenaline rush, Paintball Sports, also 11.3km away, provides a vibrant paintball experience. For stunning scenery, hike the Labyrinth Trailhead located 17.7km away, surrounded by nature’s beauty.

Nightlife

A night in Highland promises a delightful mix of entertainment. Catch a show at the Chance Theater for a romantic vibe, enjoy a film at the Overlook Drive-In Theater, or unleash your adventurous spirit at Fun Central, the local arcade adventure zone.

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

Booking tips and Expedia advantages for Highland

To save money on your trip to Highland, consider visiting between January and March for lower accommodation rates. Tuesdays are the cheapest days to stay, while Saturdays tend to be pricier. Use Expedia’s search tool to filter results by budget and hotel type, including eco-friendly options. Combining your hotel, flights, and activities into a package can also lead to savings. Take advantage of free activities like exploring local parks and walking trails, and utilise public transport for an economical way to get around 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 May, August and 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: Expedia’s search tool enables you to set your budget, choose your desired location, and much more. You can easily sort your search results to display prices from lowest to highest, so you can find the most affordable accommodation first. Additionally, you have the option to refine your choices by hotel type; for instance, selecting the Eco-certified filter will show you sustainable and environmentally-friendly hotels that are available for booking.
  • Consider bundling your trip: You can save some dollars by combining your Highland hotel reservation with your flights and activities through an Expedia package deal.

Find the best attractions near Highland

Highland, New York, offers a vibrant mix of outdoor adventures and cultural experiences perfect for family vacations. Visitors can explore notable attractions like historic sites, charming bridges, and nearby colleges. The area's rich Scottish heritage and picturesque Highland glens enhance the experience, making it ideal for those seeking both relaxation and exploration. Whether you’re keen on history or the great outdoors, Highland has something for everyone.

  • Culinary Institute of America: Located only 3.2km from Highland, this renowned culinary school offers a unique glimpse into the art of cooking. With its historic charm, you can enjoy exquisite dining experiences crafted by future culinary stars, making it a must-visit for food enthusiasts.
  • Vassar College: Situated 6.4km away, Vassar College boasts a modern campus with stunning architecture and vibrant city vibes. Explore its beautiful grounds, art galleries, and the rich history of this prestigious institution, perfect for a leisurely stroll.
  • Walkway Over the Hudson State Historic Park: Just 1.4km from Highland, this historic bridge offers breathtaking views of the Hudson River. Perfect for walking or cycling, it provides a serene escape with cultural significance, ideal for outdoor lovers.

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 SunnyAverageSlightly High
September64.0°F (17.8°C)Light RainMostly SunnyAverageAverage
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

When visiting Highland, New York, you have several airport options to consider. White Plains Airport (HPN) is 75.6km away, with nearby hotels like The Opus Westchester and Sonesta White Plains, both offering convenient airport shuttle services. Newburgh Airport (SWF) is closer at 27.4km, featuring hotels such as The Dutchess Inn and The Thayer Hotel, which provide transport for a fee. Lastly, Danbury Municipal Airport (DXR) is 54.7km away, with options like Hotel Zero Degrees and Crowne Plaza Danbury, both offering nearby airport access. Each airport presents various accommodation choices and transport services to ensure a smooth journey.

Frequently asked questions

What's the best place for a stay in Highland?
SureStay Plus Hotel by Best Western Highland Poughkeepsie is one of the top choices for your stay based on our traveller data. This hotel offers free breakfast and free parking. Other good options for your trip to the area are Courtyard by Marriott Poughkeepsie and Residence Inn by Marriott Kingston. See all available top hotels, or vacation rentals in Highland.
What are some of the best holiday rentals that Highland has to offer?
Our home is perfect for relaxing and having lots of fun, with near by activity's: This highly rated holiday home rental in Highland offers a fireplace, a patio and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms, as well as a kitchen with a fridge, a stovetop and a microwave, so that you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games. Another good choice for your trip to Highland is Private 37 Acre Lake Estate on 164 Acres - 11 BR. 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 room reservations are fully refundable if you cancel before the hotel's cancellation deadline, which in most cases is within 24 or 48 hours of your check-in date. If you have a reservation that's non-refundable, you might be able to still cancel and receive a refund within a 24-hour period of booking. Filter your search by fully refundable to find flexible hotel deals in Highland.
What's the best dog-friendly hotel 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.
What are some accommodation options with pools in Highland?
Wildflower Farms, Auberge Collection: Offers a full-service spa, a seasonal outdoor pool and 3 bars. Hampton Inn & Suites Poughkeepsie and Hampton Inn Kingston are a couple of other choices that feature an on-site pool. View all hotels with pools in Highland.
What's it like to stay in Highland?
Families enjoy visiting Highland, although all visitors will definitely find something to appreciate. Tourists can also enjoy the city's riverfront and mountain views. In Highland, there are 36 hotels and other accommodation options to choose from. Find out more about Highland.
What should I do while I'm visiting 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 itinerary are Apple Greens Golf Course and Franny Reese State Park. Take a look at what more there is 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 temperature of 20°C, while the coldest months are January and February, with an average of 0°C. The snowiest months in Highland are January, February, March and April, with each month seeing an average of 17 cm of snowfall.

Explore a world of travel with Expedia