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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, (960 reviews)
"Was a great stay! "
United States
Alane
$76 nightly
The price is $85
Feb 12 - Feb 13
Total with taxes and fees
SureStay Plus Hotel by Best Western Highland Poughkeepsie

Wildflower Farms, Auberge Collection

Wildflower Farms, Auberge Collection
5.0 star property
Gardiner
9.4 out of 10, Exceptional, (61 reviews)
"Everything was ok, except for the fact that we couldn’t do late check out or that we payed a bit more for a standard room. But everything else was perfect "
United States
Sandra N
$1,102 nightly
The price is $1,235
Feb 11 - Feb 12
Total with taxes and fees
Wildflower Farms, Auberge Collection

Mirbeau Inn & Spa

Mirbeau Inn & Spa
4.0 star property
Rhinebeck Village
9.6 out of 10, Exceptional, (312 reviews)
"My wife and I have stayed there for 3 straight years during December. The rooms are always clean, the staff is extremely helpful, and the spa is always top notch. The town of Rhinebeck is beautiful, especially during the Christmas season, and the restaurants are incredible. We look forward to our next stay at Mirbeau Rhinebeck. "
United States
christian
$428 nightly
The price is $484
Feb 8 - Feb 9
Total with taxes and fees
Mirbeau Inn & Spa

Buttermilk Falls Inn

Buttermilk Falls Inn
3.0 star property
Milton
9.4 out of 10, Exceptional, (41 reviews)
"Excellent "
United States
Carlos
$494 nightly
The price is $553
Feb 8 - Feb 9
Total with taxes and fees
Buttermilk Falls Inn

Millbrook Country House Bed & Breakfast

Millbrook Country House Bed & Breakfast
4.0 star property
Millbrook
9.0 out of 10, Wonderful, (81 reviews)
"Great staff and stay for work"
United States
Paul
$225 nightly
The price is $255
Feb 8 - Feb 9
Total with taxes and fees
Millbrook Country House Bed & Breakfast

Moondance Ridge Bed & Breakfast

Moondance Ridge Bed & Breakfast
3.0 star property
New Paltz
9.4 out of 10, Exceptional, (80 reviews)
"Great place: Clean, romantic, fresh continental breakfast available all day. Room had a hot tub. "
United States
Marina
$264 nightly
The price is $296
Feb 11 - Feb 12
Total with taxes and fees
Moondance Ridge Bed & Breakfast

Cold Spring Hotel

Cold Spring Hotel
3.0 star property
Cold Spring
8.6 out of 10, Excellent, (155 reviews)
"The owner is so warm and kind. The room was clean. Great place to stay for the weekend! "
United States
Wydayessi
$229 nightly
The price is $247
Feb 9 - Feb 10
Total with taxes and fees
Cold Spring Hotel

Kingston Carriage House

Kingston Carriage House
4.0 star property
Rondout
9.0 out of 10, Wonderful, (30 reviews)
"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
Feb 9 - Feb 10
Total with taxes and fees
Kingston Carriage House

The Wiltwyck

The Wiltwyck
3.5 star property
Kingston
9.4 out of 10, Exceptional, (169 reviews)
"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
$144 nightly
The price is $161
Feb 8 - Feb 9
Total with taxes and fees
The Wiltwyck

Cromwell Manor Inn

Cromwell Manor Inn
4.0 star property
Cornwall
9.4 out of 10, Exceptional, (95 reviews)
"Great stay!"
United States
Amrita
$266 nightly
The price is $314
Feb 22 - Feb 23
Total with taxes and fees
Cromwell Manor Inn

The Factory

The Factory
2.0 star property
Beacon
9.8 out of 10, Exceptional, (72 reviews)
"Gorgeous little Hotel. Would 100% stay there again."
United States
Edward
$265 nightly
The price is $305
Feb 8 - Feb 9
Total with taxes and fees
The Factory

Minnewaska Lodge

Minnewaska Lodge
3.0 star property
Gardiner
9.0 out of 10, Wonderful, (542 reviews)
"Superb lodge resort situated in a State Park near New Paltz. Great staff, beautiful rooms, amazing vreakfast"
United States
Allan
$172 nightly
The price is $192
Feb 12 - Feb 13
Total with taxes and fees
Minnewaska Lodge

Twin Gables of Woodstock

Twin Gables of Woodstock
3.0 star property
Woodstock
9.8 out of 10, Exceptional, (196 reviews)
"Staff very accommodating, great vibe and location. "
United States
Lynn
$149 nightly
The price is $167
Feb 8 - Feb 9
Total with taxes and fees
Twin Gables of Woodstock

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
$102 nightly
The price is $115
Feb 11 - Feb 12
Total with taxes and fees
Rhinebeck Village Inn

The Gables of Rhinebeck Inn

The Gables of Rhinebeck Inn
3.0 star property
Rhinebeck Village
9.2 out of 10, Wonderful, (115 reviews)
" Convenient to walking around town"
United States
Terence
$270 nightly
The price is $305
Feb 22 - Feb 23
Total with taxes and fees
The Gables of Rhinebeck Inn

The Herwood Inn

The Herwood Inn
4.5 star property
Woodstock
9.8 out of 10, Exceptional, (99 reviews)
"Great property, room, location & staff."
United States
Joseph
$172 nightly
The price is $193
Feb 9 - Feb 10
Total with taxes and fees
The Herwood Inn

Inness

Inness
5.0 star property
Accord
9.2 out of 10, Wonderful, (92 reviews)
"Pros: Beautiful cabins, great restaurant (food and ambiance), lovely fitness class, dreamy massage. Cons: Staff "
United States
Joanne
$642 nightly
The price is $719
Mar 1 - Mar 2
Total with taxes and fees
Inness

Journey Inn Bed & Breakfast

Journey Inn Bed & Breakfast
4.0 star property
Hyde Park
9.6 out of 10, Exceptional, (338 reviews)
"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
Feb 8 - Feb 9
Total with taxes and fees
Journey Inn Bed & Breakfast

The Dutchess Inn and Spa at Beacon

The Dutchess Inn and Spa at Beacon
3.5 star property
Beacon
9.2 out of 10, Wonderful, (171 reviews)
"Great room, great location and super friendly staff. "
United States
Victor
$303 nightly
The price is $349
Feb 18 - Feb 19
Total with taxes and fees
The Dutchess Inn and Spa at Beacon

Woodstock Way Hotel

Woodstock Way Hotel
4.0 star property
Woodstock
9.6 out of 10, Exceptional, (230 reviews)
"The room and views were lovely, and we loved the Tannery cafe!"
United States
Katherine
$258 nightly
The price is $285
Feb 9 - Feb 10
Total with taxes and fees
Woodstock Way Hotel
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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.

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 stays in Highland

Hotels in Highland with star-rating

Find out more about Highland

Top reasons to visit Highland

  • Outdoor Adventures: Highland offers a variety of outdoor activities, including skiing and exploring local parks, perfect for adventure seekers.
  • Family-Friendly Activities: The area is packed with attractions suitable for families, providing entertainment for all ages.
  • Scenic Landscapes: Enjoy picturesque views and tranquil spots for relaxation and romantic getaways.
  • Cultural Experiences: Visit historic sites and local galleries to appreciate the rich culture and creative scene.
  • Diverse Accommodations: Choose from a range of lodging options, including pet-friendly hotels and agritourism properties.

Find great hotels near Highland

Discover the charm of Highland, New York, with a variety of hotel accommodations tailored to meet the needs of every traveler. From pet-friendly options to business-themed stays, Highland offers a range of lodging types, including hotels and agritourism properties. Whether you're seeking adventure or relaxation, you'll find the best hotels in the area, complete with positive reviews to guide your choice for a memorable getaway.

  • Best Western Fishkill Inn & Suites: Embracing a warm and welcoming theme, Best Western Fishkill Inn & Suites is ideal for families and pet lovers alike. Located 14 miles from Highland, this 3.5-star hotel offers an inclusive environment, proudly affiliated with LGBTQIA travel guides. Families can enjoy complimentary amenities such as cribs, while furry friends are also accommodated with a pet-friendly policy. With a focus on comfort and accessibility, this property ensures that all guests, including children, feel at home during their stay.
  • HYATT house Fishkill/Poughkeepsie: Designed with the modern traveler in mind, HYATT house Fishkill/Poughkeepsie combines business and leisure seamlessly. Situated 14 miles from Highland, this 3-star hotel provides a range of amenities catering to both families and business professionals. Guests will appreciate the multiple meeting rooms and business center, along with child-friendly services like cribs and window guards. The hotel also welcomes pets, making it a versatile choice for all types of travelers looking for convenience and comfort.
  • Quality Inn & Suites Fishkill South near I-84: Offering a blend of professionalism and family-friendly features, Quality Inn & Suites is perfect for business travelers and families. Located 14 miles from Highland, this property is noted for its supportive atmosphere for LGBTQIA guests. Facilities include a business center and meeting rooms, ensuring that work needs are met without sacrificing comfort. Families will find cribs and window guards available, creating a safe environment for children while enjoying their stay.

Where to stay near Highland

Highland, New York, offers an exciting vacation experience for outdoor enthusiasts and families alike. With its scenic landscapes and sunny weather, visitors can explore local parks and enjoy various activities. The nearby areas provide a friendly atmosphere perfect for weekend getaways, where you can relax and connect with nature. Whether you're seeking adventure or a tranquil retreat, Highland and its surroundings have something special for every traveler.

  • Poughkeepsie: Located 2 miles from Highland, Poughkeepsie is a vibrant city that offers a blend of outdoor fun and urban conveniences. Known for its educational institutions and shopping areas, Poughkeepsie draws visitors throughout the year, peaking in the summer and fall months. Enjoy activities like exploring local parks, shopping in bustling centers, and visiting landmarks such as the scenic views along the Hudson River. With a mix of family-friendly attractions and city-themed experiences, Poughkeepsie is perfect for those seeking a dynamic travel experience.
  • New Paltz: Just 7 miles from Highland, New Paltz is an adventure lover’s paradise, renowned for its breathtaking scenery and outdoor activities. The city experiences peak travel in the spring and late summer, making it an ideal destination for hiking, skiing, and exploring nature reserves. Visitors can also enjoy the vibrant local arts scene and charming shops that add to the town’s appeal. With easy access to beautiful lakes and mountains, New Paltz promises a delightful escape for those looking to immerse themselves in nature.
  • Hyde Park: Located 4 miles from Highland, Hyde Park is an enchanting city steeped in history and culture. Popular for its outdoor activities and family-oriented attractions, it sees a surge in visitors during the summer and early fall. Visitors can explore historic landmarks, enjoy recreational activities, and shop in local areas. With notable sites such as the Franklin D. Roosevelt Presidential Library and Museum and beautiful lakes, Hyde Park offers a rich cultural experience combined with opportunities for relaxation and adventure.

Things to do in and around Highland

Highland, New York, offers a delightful mix of outdoor adventures and family-friendly activities. Visitors can enjoy skiing, explore recreational areas, and engage in educational experiences. For those seeking romance, the picturesque landscapes provide perfect getaway spots. Additionally, sports enthusiasts can find facilities for various sports, while art lovers can visit local galleries to appreciate the creative scene. Highland truly has something for everyone, making it an ideal vacation destination.

Shopping

For shopping in Highland, visit the Poughkeepsie Galleria, a vibrant mall 7 miles away offering various stores and entertainment. If you're up for a drive, check out the Hudson Valley Mall 17 miles away for more shopping options and family-friendly vibes.

Recreation

Apple Greens Golf Course offers a refreshing outdoor experience with its beautifully maintained greens, perfect for a relaxing day of golf. For a more laid-back vibe, the Richard L. Skimin Memorial Baseball Field provides a tranquil park atmosphere ideal for unwinding. Enjoy family-friendly entertainment at Bananas Comedy Club, where laughter reigns.

Adventure

At North Landing Beach, enjoy camping surrounded by nature, perfect for family and outdoor adventures. For adrenaline seekers, Paintball Sports offers thrilling action-packed experiences. Explore the scenic Labyrinth Trailhead, an 11-mile hike that showcases the area's beautiful landscapes and adventurous spirit.

Nightlife

In Highland, the Chance Theater offers a charming mix of culture and romance just 2 miles away, perfect for a night out. For a classic movie experience, head to the Overlook Drive-In Theater, located 5 miles from town, where entertainment meets nostalgia. Adventure awaits at Fun Central, 9 miles away, with exciting arcade games for all ages.

*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, visit between January and March for lower accommodation rates, especially on Tuesdays. Avoid Saturdays, which are pricier. Use Expedia to find sustainable hotels by applying the Eco-certified filter, and sort results from lowest to highest price for the best deals. Consider bundling your hotel, flights, and activities for additional savings, and join the One Key membership for exclusive discounts and rewards. Always compare room rates and take advantage of any great offers available to maximize your budget.

  • 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: Utilize Expedia's search tool to customize your options based on your budget, desired location, and preferred type of accommodation. For instance, selecting the Eco-certified filter will showcase sustainable and environmentally friendly hotels currently available. To find the best prices and deals, simply arrange the price filter from lowest to highest.
  • Consider bundling your trip: You can save money by combining your hotel stay in Highland with your flights and activities through an Expedia package.
  • Become a One Key member: Join Expedia's One Key membership program for exclusive discounts and deals on hotel bookings. You can also earn OneKeyCash to use on future selected hotels.

Find the best attractions near Highland

Highland, New York, offers a perfect blend of outdoor adventures and family-friendly activities. Visitors can explore a variety of attractions, including modern colleges and universities, historic bridges, and notable historic sites. Whether you’re seeking cultural experiences or outdoor fun, Highland has something to cater to every traveler's interests.

  • Culinary Institute of America: A renowned institution for culinary arts, the Culinary Institute of America offers a unique blend of education and culture. You can explore its beautiful campus, enjoy exquisite dining options at student-run restaurants, and immerse yourself in the culinary heritage that shapes American cuisine.
  • Vassar College: Known for its stunning architecture and vibrant campus life, Vassar College is a modern liberal arts college that exudes city vibes. Stroll through the picturesque grounds, visit art galleries, and enjoy the lively atmosphere created by students and faculty.
  • Walkway Over the Hudson State Historic Park: This iconic pedestrian bridge offers breathtaking views of the Hudson River and the surrounding landscape. Ideal for walking, biking, or simply taking in the scenery, it’s a cultural landmark that connects communities and provides a unique perspective on the area’s history.

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 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

If you're planning to visit Highland, New York, there are several major airports nearby. White Plains Airport (HPN) is 47 miles away, with accommodations such as The Opus Westchester and Sonesta White Plains Downtown, both 4 miles from the airport, offering convenient transportation services. Newburgh Airport (SWF) is closer at 17 miles, with options like The Dutchess Inn and Spa and The Thayer Hotel, both within 11 miles. Lastly, Danbury Municipal Airport (DXR) is located 34 miles from Highland, featuring hotels like Hotel Zero Degrees and Ethan Allen Hotel, both just a short drive away. Each airport provides nearby hotel access for a comfortable stay.

Frequently asked questions

What is the best area to stay in Highland?
For most visitors, the best area to stay in Highland, New York, is near the Walkway Over the Hudson State Historic Park, particularly along Haviland Road and the surrounding streets.

This area is the focal point for visitors, offering direct access to the Walkway Over the Hudson, a converted railway bridge that provides scenic views of the Hudson River. The streets here are home to various local eateries and shops, making it a convenient and pleasant place to explore on foot.

Couples often find this location ideal for a relaxed getaway. They can enjoy leisurely strolls across the Walkway, explore the nearby Franny Reese State Park with its walking trails, and dine at local restaurants, many of which offer outdoor seating with river views. It's a nice setting for a quiet escape.

For travelers who value convenience and access to outdoor activities, staying closer to the Hudson Valley Rail Trail on the Highland side is also a good option. This allows for easy cycling and walking along the trail, connecting to other local parks and attractions.
What are the best hotels in Highland that travelers recommend?
For the best hotels in Highland that travelers recommend, consider the SureStay Plus Hotel by Best Western Highland Poughkeepsie.

This hotel, with a 7.8 rating, is frequently praised by guests for its comfortable and clean rooms, as well as its great and amazing staff. Travelers also highlight the comfortable beds and the lovely lobby. It offers convenient amenities such as air conditioning, a free continental breakfast, and some rooms include a kitchen, which can be very useful for longer stays.
What are the best family hotels in Highland?
For family-friendly hotels in Highland, the SureStay Plus Hotel by Best Western Highland Poughkeepsie is a highly-rated option.

The SureStay Plus Hotel by Best Western Highland Poughkeepsie, with a 7.8 rating, offers comfortable and clean rooms, as noted by many guests. Travelers frequently praise the great and amazing staff and comfortable beds, along with great customer service. This hotel provides convenient amenities such as connecting rooms, early check-in options, and complimentary continental breakfast, making it a practical choice for families. Find more child-friendly accommodations in Highland
What hotels in Highland offer free breakfast?
In Highland, the SureStay Plus Hotel by Best Western Highland Poughkeepsie offers free breakfast.

This hotel, with a 7.8 rating, provides both free breakfast and complimentary continental breakfast daily. Guests consistently describe the rooms as comfortable and clean, and the staff as great and amazing, providing excellent customer service. The lobby is also noted as lovely. Additionally, the hotel offers free self-parking and free RV, bus, and truck parking. 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, warmly welcomes pets, specifically dogs. Guests frequently describe the rooms as comfortable and clean, and the staff as great and amazing. Its amenities include the option for early check-in, and it is located approximately 63 miles from the Hudson River. See more pet-friendly hotels in Highland
What are the best budget hotels in Highland?
For budget hotels in Highland, the SureStay Plus Hotel by Best Western Highland Poughkeepsie is a recommended option.

This hotel, with a 7.8 rating, offers guests a comfortable and clean stay. Travelers frequently mention the great and amazing staff, along with comfortable beds. Amenities include free continental breakfast, free self-parking, and complimentary toiletries. The lobby is described as lovely, contributing to a pleasant experience. 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 between late spring (May) and early fall (October).

This period offers the most pleasant weather for outdoor activities, which is a key draw for visitors to Highland. Temperatures are generally mild to warm, making it comfortable for exploring the Walkway Over the Hudson, visiting local farms, or enjoying the scenic beauty of the Hudson Valley.

For travelers who appreciate vibrant foliage and cooler temperatures, late September through October is particularly appealing. The autumn colors throughout the Hudson Valley are spectacular, providing stunning views from the Walkway and during drives along the scenic routes. This time of year is ideal for couples seeking picturesque landscapes and a cozy getaway.

Families often find the summer months (June-August) most convenient due to school holidays.
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?
With Expedia, you earn OneKeyCash™* on eligible Highland hotel bookings for every dollar you spend – just join our One Key™ travel rewards program to get started. It's free to join, and you'll unlock our lowest Member Prices as soon as you're signed in. On top of this, you could also save significantly by bundling your hotel and flights together on Expedia.

*Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia, Hotels.com and Vrbo.
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 $80 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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