Highland hotels

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Booking Insights

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 9-10 Sep.
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
7.7Good(454)
Parking
Free Wi-Fi
Pet-friendly
Air conditioning
£69+
Check availability
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
8.2Very Good(597)
Parking
Free Wi-Fi
Air conditioning
£124+
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(430)
Parking
Free Wi-Fi
Pool
Pet-friendly
£155+
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(368)
Parking
Free Wi-Fi
Pet-friendly
Air conditioning
£189+
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(811)
Parking
Free Wi-Fi
Pet-friendly
Air conditioning
£133+
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
£96+
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
7.8Good(150)
Free Wi-Fi
Pool
Pet-friendly
Air conditioning
£273+
Check availability

Cheap hotels in Highland

These are the cheapest hotels for 9-10 Sep.
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
£133+
Check availability
The Heartwood - Poughkeepsie - Bedroom
The Heartwood
Poughkeepsie, NY, United States
9.5Wonderful(130)
Parking
Free Wi-Fi
Pet-friendly
Air conditioning
£165+
Check availability
Black Creek Bed and Breakfast - Highland
Black Creek Bed and Breakfast
Highland, NY, United States
9.6Wonderful(46)
Free Wi-Fi
£215+
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
£230+
Check availability
Secluded Country Getaway - Highland - Living room
Secluded Country Getaway
Highland, NY, United States
8.8Very Good(28)
House
£239+
Check availability
Alumnae House, the Inn at Vassar College - Poughkeepsie
Alumnae House, the Inn at Vassar College
Poughkeepsie, NY, United States
10Wonderful(1)
Parking
Free Wi-Fi
Air conditioning
£292+
Check availability

Hotel deals for next week

Some of our guests’ favourite hotels with availability next week 9-10 Sep.
DoubleTree by Hilton Poughkeepsie Convention Center - Poughkeepsie - Lounge
DoubleTree by Hilton Poughkeepsie Convention Center
Poughkeepsie, NY, United States
8.0Very Good(639)
Free Wi-Fi
Air conditioning
£149+
Check availability
Holiday Inn Poughkeepsie By IHG - Poughkeepsie - Bedroom
Holiday Inn Poughkeepsie By IHG
Poughkeepsie, NY, United States
7.2Good(713)
Parking
Free Wi-Fi
Pool
Pet-friendly
£114+
Check availability
Hyatt Place Poughkeepsie - Poughkeepsie - Bedroom
Hyatt Place Poughkeepsie
Poughkeepsie, NY, United States
8.4Very Good(1170)
Parking
Free Wi-Fi
Pool
Pet-friendly
£179+
Check availability
Inn at Bellefield / Hyde Park - Hyde Park - Lounge
Inn at Bellefield / Hyde Park
Hyde Park, NY, United States
9.2Wonderful(127)
Free Wi-Fi
Pet-friendly
Air conditioning
£251+
Check availability
Homewood Suites by Hilton Poughkeepsie - Poughkeepsie - Building
Homewood Suites by Hilton Poughkeepsie
Poughkeepsie, NY, United States
8.9Very Good(430)
Parking
Free Wi-Fi
Pool
Pet-friendly
£166+
Check availability
Home2 Suites by Hilton Poughkeepsie - Poughkeepsie - Patio
Home2 Suites by Hilton Poughkeepsie
Poughkeepsie, NY, United States
8.8Very Good(168)
Parking
Free Wi-Fi
Pool
Pet-friendly
£160+
Check availability

Top-rated hotels

Stay at the hotels that our users loved the most 9-10 Sep.
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
£524+
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
£1,679+
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
£525+
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(20)
House
Parking
Free Wi-Fi
Air conditioning
£394+
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
£649+
Check availability

Popular filters in Highland hotels

Hotels with parking
SureStay Plus by Best Western Highland Poughkeepsie, Holiday Inn Express Poughkeepsie By IHG 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
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Booking Insights

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 £54/night. The highest prices are found on Wednesday, with average rates at £248/night.

Find deals

Good to know

Low season

High season

Average price (weeknight)

Average price (weekend night)

April
August
£92
£168
Cheapest month to stay with an average 45% drop in price.
Most expensive month to stay with an average 71% 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 SureStay Plus by Best Western Highland Poughkeepsie, Holiday Inn Express Poughkeepsie By IHG and Hampton Inn & Suites 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