Highland hotels

Compare 100s of travel sites at once to find the right place at the right price.

Unlock up to 30% off with Member Rates and Private Deals.

Filter searches by price, freebies and more to find your best hotels.

Best Highland hotels

Discover the best hotels in Highland and compare prices, ratings, and locations to find the right stay for your trip.
These are the best prices for 19-20 Aug.
Holiday Inn Express Poughkeepsie By IHG - Poughkeepsie - Building
Holiday Inn Express Poughkeepsie By IHG - Poughkeepsie - Building
Holiday Inn Express Poughkeepsie By IHG
Poughkeepsie, NY, United States
8.3Very Good(577)
Parking
Free Wi-Fi
Air conditioning
R2 301+
Check availability
Best Western Plus The Inn & Suites at the Falls - Poughkeepsie - Living room
Best Western Plus The Inn & Suites at the Falls - Poughkeepsie - Living room
Best Western Plus The Inn & Suites at the Falls
Poughkeepsie, NY, United States
7.5Good(807)
Parking
Free Wi-Fi
Pet-friendly
Air conditioning
R2 414+
Check availability
Red Roof Plus+ Poughkeepsie - Poughkeepsie - Building
Red Roof Plus+ Poughkeepsie - Poughkeepsie - Building
Red Roof Plus+ Poughkeepsie
Poughkeepsie, NY, United States
5.8Fair(669)
Parking
Free Wi-Fi
Pet-friendly
Air conditioning
R2 430+
Check availability
Hampton Inn & Suites Poughkeepsie - Poughkeepsie - Lounge
Hampton Inn & Suites Poughkeepsie - Poughkeepsie - Lounge
Hampton Inn & Suites Poughkeepsie
Poughkeepsie, NY, United States
8.6Very Good(428)
Parking
Free Wi-Fi
Pool
Pet-friendly
R2 704+
Check availability
Courtyard by Marriott Poughkeepsie - Poughkeepsie - Lounge
Courtyard by Marriott Poughkeepsie - Poughkeepsie - Lounge
Courtyard by Marriott Poughkeepsie
Poughkeepsie, NY, United States
8.4Very Good(365)
Parking
Free Wi-Fi
Pet-friendly
Air conditioning
R3 290+
Check availability
Residence Inn by Marriott Poughkeepsie - Poughkeepsie - Lobby
Residence Inn by Marriott Poughkeepsie - Poughkeepsie - Lobby
Residence Inn by Marriott Poughkeepsie
Poughkeepsie, NY, United States
7.7Good(152)
Free Wi-Fi
Pool
Pet-friendly
Air conditioning
R4 704+
Check availability
SureStay Plus by Best Western Highland Poughkeepsie - Highland - Bedroom
SureStay Plus by Best Western Highland Poughkeepsie - Highland - Bedroom
SureStay Plus by Best Western Highland Poughkeepsie
Highland, NY, United States
7.8Good(451)
Parking
Free Wi-Fi
Pet-friendly
Air conditioning
R2 284+
Check availability

Cheap hotels in Highland

These are the cheapest hotels for 19-20 Aug.
Sams Cottage Bed and Breakfast on the Greens - Highland - Living room
Sams Cottage Bed and Breakfast on the Greens
Highland, NY, United States
10Wonderful(2)
Free Wi-Fi
R2 916+
Check availability
The Heartwood - Poughkeepsie - Bedroom
The Heartwood
Poughkeepsie, NY, United States
9.5Wonderful(130)
Parking
Free Wi-Fi
Pet-friendly
Air conditioning
R3 686+
Check availability
Black Creek Bed and Breakfast - Highland
Black Creek Bed and Breakfast
Highland, NY, United States
9.6Wonderful(46)
Free Wi-Fi
R4 715+
Check availability
Idyllic Home on the Hudson w/ Updated Interior! - Highland
Idyllic Home on the Hudson w/ Updated Interior!
Highland, NY, United States
6.4Okay(9)
House
R5 039+
Check availability
Secluded Country Getaway - Highland - Living room
Secluded Country Getaway
Highland, NY, United States
8.6Very Good(28)
House
Parking
Free Wi-Fi
Pool
Air conditioning
R5 233+
Check availability
5 miles from New Paltz, close to Vassar, SUNY ideal for weddings and graduations - Clintondale - Balcony
5 miles from New Paltz, close to Vassar, SUNY ideal for weddings and graduations
Clintondale, NY, United States
10Wonderful(7)
Air conditioning
R7 987+
Check availability

Hotel deals for next week

Some of our guests’ favourite hotels with availability next week 19-20 Aug.
DoubleTree by Hilton Poughkeepsie Convention Center - Poughkeepsie - Lounge
DoubleTree by Hilton Poughkeepsie Convention Center
Poughkeepsie, NY, United States
7.9Good(633)
Free Wi-Fi
Air conditioning
R2 613+
Check availability
Hyatt Place Poughkeepsie - Poughkeepsie - Bedroom
Hyatt Place Poughkeepsie
Poughkeepsie, NY, United States
8.5Very Good(1151)
Parking
Free Wi-Fi
Pool
Pet-friendly
R2 499+
Check availability
Holiday Inn Poughkeepsie By IHG - Poughkeepsie - Bedroom
Holiday Inn Poughkeepsie By IHG
Poughkeepsie, NY, United States
7.1Good(711)
Parking
Free Wi-Fi
Pool
Pet-friendly
R2 187+
Check availability
Inn at Bellefield / Hyde Park - Hyde Park - Lounge
Inn at Bellefield / Hyde Park
Hyde Park, NY, United States
9.2Wonderful(125)
Free Wi-Fi
Pet-friendly
Air conditioning
R5 369+
Check availability
Homewood Suites by Hilton Poughkeepsie - Poughkeepsie - Building
Homewood Suites by Hilton Poughkeepsie
Poughkeepsie, NY, United States
8.9Very Good(428)
Parking
Free Wi-Fi
Pool
Pet-friendly
R3 453+
Check availability
Home2 Suites by Hilton Poughkeepsie - Poughkeepsie - Patio
Home2 Suites by Hilton Poughkeepsie
Poughkeepsie, NY, United States
8.8Very Good(164)
Parking
Free Wi-Fi
Pool
Pet-friendly
R3 660+
Check availability

Top-rated hotels

Stay at the hotels that our users loved the most 19-20 Aug.
Black Walnut Tree Farm: 50-Acres + Private Pond - Highland - Living room
Black Walnut Tree Farm: 50-Acres + Private Pond
Highland, NY, United States
10Wonderful(16)
House
Air conditioning
R11 487+
Check availability
Splendid Isolation: Private Luxury. Breathtaking Modern Villa On Hudson Bluffs. - Highland - Living room
Splendid Isolation: Private Luxury. Breathtaking Modern Villa On Hudson Bluffs.
Highland, NY, United States
9.9Wonderful(24)
House
Free Wi-Fi
Pool
Air conditioning
R36 810+
Check availability
Luxury Hudson Valley Retreat Perfect for Families, Friends & Weekend Escapes - Highland - Bedroom
Luxury Hudson Valley Retreat Perfect for Families, Friends & Weekend Escapes
Highland, NY, United States
9.8Wonderful(29)
House
Air conditioning
R11 244+
Check availability
Spacious 4bd Country Gem - Fire Pit & Chill Vibes - Highland - Stairs
Spacious 4bd Country Gem - Fire Pit & Chill Vibes
Highland, NY, United States
9.7Wonderful(18)
House
Parking
Free Wi-Fi
Air conditioning
R7 712+
Check availability
Historic 4 BR Family Home Near Buttermilk Falls & Hudson River, on 5 Acres - Milton - Dining room
Historic 4 BR Family Home Near Buttermilk Falls & Hudson River, on 5 Acres
Milton, NY, United States
9.7Wonderful(15)
Air conditioning
R7 193+
Check availability

Popular filters in Highland hotels

Hotels with parking
Holiday Inn Express Poughkeepsie By IHG, Best Western Plus The Inn & Suites at the Falls and others
Find stays
Hotels with free cancellation
Explore hotel deals with free cancellation in the area
Find stays
Hotels with a pool
Hampton Inn & Suites Poughkeepsie, Residence Inn by Marriott Poughkeepsie, and 5 more
Find stays

KAYAK’s insights for hotels in Highland

Discover seasonal trends, ideal booking windows, and other data-driven tips to plan your stay in Highland with confidence.

What is the cheapest day of the week to book a hotel in Highland?

Tuesday offers the lowest rates in Highland, with an average nightly price of R1 191/night. The highest prices are found on Wednesday, with average rates at R5 442/night.

Find deals

Good to know

Low season

High season

Average price (weeknight)

Average price (weekend night)

April
October
R3 014
R3 135
Cheapest month to stay with an average 55% drop in price.
Most expensive month to stay with an average 81% rise in price.
Average Sun - Thu price over the last 2 weeks.
Average Fri & Sat price over the last 2 weeks.

FAQs when booking a hotel in Highland

  • How do I find a hotel in central Highland?

    After you launch a hotel search on KAYAK, you can refine your research by neighbourhood, which allows you to pick the central Highland districts. You can also do a search using the city map to choose a specific location, like Highland city centre

  • How can I find hotels near me?

    Take a look at our extensive hotel map to find the best hotels near you.

  • Are there Highland hotels with free parking?

    There are many hotels in Highland that offer both parking and free parking. Popular choices among KAYAK users include Holiday Inn Express Poughkeepsie By IHG, Best Western Plus The Inn & Suites at the Falls and Red Roof Plus+ Poughkeepsie.

Where to stay in Highland?

Our map will help you find the perfect place to stay in Highland by showing you the exact location of each hotel.

Everything you need to know for your stay in Highland

All hotels in Highland