Highland Holiday Rentals, New York: Private House Rentals

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

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Our top choices for Highland hotels

A hotel room with two beds, a desk, a chair, a lamp, and a window with curtains.

A hotel reception area with a wooden reception desk, a clock on the wall, and a coffee machine in the background.

A room with a dark blue wall, a round wooden table with a plant, and four patterned chairs.

A modern living room with a dark blue accent wall, a flat-screen TV mounted on the wall, a blue sofa, a coffee table, and a lamp.

1. SureStay Plus Hotel by Best Western Highland Poughkeepsie

Highland

Jamie

฿2,949

฿3,303 total

includes taxes & fees

20 Sept - 21 Sept

A modern hotel with a prominent 'Hyatt Place' sign, outdoor seating area, and a covered entrance.

A reception area with a geometric patterned wall, a reception desk, a sofa, and a dining area with chairs and a table.

A modern bar area with round tables and patterned chairs, a bar counter with a TV, and shelves with bottles.

A modern bar area with round tables and chairs, a bar counter with a variety of bottles, and a large screen mounted on the wall.

2. Hyatt Place Poughkeepsie / Hudson Valley

Crown Heights

Katlin

฿3,338

฿3,876 total

includes taxes & fees

22 Sept - 23 Sept

A hotel room with a bed, a TV on a wooden stand, a dining area with chairs, and a patterned carpet.

A lobby with a wooden bench, a reception desk, and a colorful artwork on the wall.

A spacious conference room with multiple tables and chairs, large windows, and a carpeted floor.

A modern living room with a dining area, a TV mounted on the wall, and a patterned carpet.

3. Holiday Inn Express Poughkeepsie by IHG

Poughkeepsie

John

฿3,206

฿3,723 total

includes taxes & fees

4 Oct - 5 Oct

A modern hotel lobby with wooden flooring, yellow chairs, a long dining table, and pendant lighting.

A reception area with a wooden floor, a reception desk, and a wall with a welcome sign.

A snack display area with shelves stocked with various snacks and a large wall advertisement for treats.

An indoor swimming pool with clear water, a lifeguard chair, and a sunlit area with lounge chairs.

4. Hampton Inn & Suites Poughkeepsie

Crown Heights

Sanford

฿3,090

฿3,588 total

includes taxes & fees

28 Sept - 29 Sept

A multi-story hotel with a central entrance, stone pillars, and a brick facade.

A spacious bar area with a high ceiling and large windows, surrounded by comfortable seating and a rustic wooden ceiling.

A spacious living area with stone pillars, leather sofas, a fireplace, and a kitchen in the background.

A kitchen counter with various baked goods displayed on shelves and a wooden stand.

5. Inn at Bellefield / Hyde Park, Residence Inn by Marriott

Hyde Park

Sanjiv

฿6,048

฿6,842 total

includes taxes & fees

12 Oct - 13 Oct

An outdoor seating area with stone walls, a fire feature, and yellow chairs.

A modern indoor seating area with a sofa, tables, and chairs, featuring large windows and a clean, contemporary design.

An indoor swimming pool with clear water, surrounded by green and red chairs, and a tiled floor.

A multi-story hotel with a modern design, featuring a covered outdoor seating area and a parking lot.

6. Home2 Suites By Hilton Poughkeepsie

Poughkeepsie

Sandra

฿4,038

฿4,689 total

includes taxes & fees

28 Sept - 29 Sept

A modern gym with treadmills, elliptical machines, and weightlifting equipment.

A conference room with multiple tables and chairs, chandeliers, a whiteboard, and an exit sign.

A spacious lobby with a reception desk, seating area, and a large window.

A hotel reception area with a modern design, featuring a reception desk, a large mirror, and a chandelier.

7. DoubleTree by Hilton Poughkeepsie Convention Center

Downtown Poughkeepsie

Amanda

฿3,361

฿3,936 total

includes taxes & fees

27 Sept - 28 Sept

A dining area with round tables and chairs, a large window with curtains, a flat-screen TV, and a potted plant.

A gym with a treadmill, weight bench, and various exercise machines.

A hotel lobby with a reception desk, a seating area with two leather chairs and a small table, and a framed artwork on the wall.

A hotel entrance with a covered walkway, a sign indicating low clearance, and a flag.

8. Americas Best Value Inn New Paltz

New Paltz

Evan

฿3,863

฿4,326 total

includes taxes & fees

20 Sept - 21 Sept

A lobby with a stone fireplace, patterned armchairs, and a large rug.

An indoor swimming pool with clear blue water, surrounded by windows and potted plants.

A snack display area with various packaged snacks and a refrigerated section.

A spacious hotel lobby with a central bar area, seating arrangements, and a television mounted on the wall.

9. Hampton Inn by Hilton New Paltz

New Paltz

Hilda

฿4,309

฿4,826 total

includes taxes & fees

21 Sept - 22 Sept

A spacious living area with a stone fireplace, comfortable seating, a kitchen with bar seating, and large windows.

An indoor swimming pool with tiled flooring, a pool ladder, and multiple seating areas with chairs.

A sign for Residence Inn by Marriott with a landscaped flower bed in front.

An outdoor seating area with a fire feature, wicker chairs, and a grill in the background.

10. Residence Inn by Marriott Poughkeepsie

Poughkeepsie

Chandra

฿4,726

฿5,488 total

includes taxes & fees

27 Sept - 28 Sept

A Courtyard by Marriott hotel with a modern design, large windows, and a well-maintained lawn.

A modern hotel lobby with seating areas, a bar, and a staircase.

A modern hotel room with a sofa, armchair, ottoman, flat-screen TV, and large windows with sheer curtains.

A reception area with two wooden reception desks, a wall-mounted screen, and a vending machine labeled "market".

11. Courtyard by Marriott Poughkeepsie

Poughkeepsie

Celine

฿3,636

฿4,113 total

includes taxes & fees

4 Oct - 5 Oct

A courtyard with a fire pit, outdoor seating, and a covered area with string lights.

A gym with exercise equipment, dumbbells, treadmills, and a bench.

A spacious hotel lobby with a high ceiling, wooden beams, and a large seating area with sofas and round tables.

A hotel lobby with a reception desk, seating area, and a stone fireplace.

12. Homewood Suites by Hilton Poughkeepsie

Poughkeepsie

Kayleigh

฿4,580

฿5,319 total

includes taxes & fees

21 Sept - 22 Sept

A building entrance with a covered porch, stone pillars, and a mailbox.

A gym with exercise equipment, a mirror, and a door leading to a room.

A hotel room with a flat-screen TV, a mini-fridge, a microwave, a desk with a lamp, and a chair.

A hotel dining area with wooden tables and chairs, a kitchen counter, a refrigerator, and a television on the wall.

13. Quality Inn Hyde Park Poughkeepsie North

Hyde Park

Joshua

฿2,804

฿3,172 total

includes taxes & fees

12 Oct - 13 Oct

A modern bar area with a long counter, multiple bar stools, and a variety of liquor bottles.

A well-organized snack and beverage area with refrigerated sections and shelves stocked with various snacks and drinks.

A modern restaurant with a long counter, multiple seating areas, and a visible kitchen in the background.

14. Holiday Inn Poughkeepsie by IHG

Poughkeepsie

Valerie

฿3,470

฿4,030 total

includes taxes & fees

28 Sept - 29 Sept

A hotel reception area with a reception desk, a waiting area with sofas, and a glass door entrance.

A hotel corridor with a vending machine, a refrigerator, and a door.

An indoor swimming pool with clear pool rules, a lifeguard chair, and a poolside area with lounge chairs.

A modern kitchen with a central island, a dining area with chairs, and a refrigerator.

15. Quality Inn Poughkeepsie

Arlington

Dawn

฿3,203

฿3,719 total

includes taxes & fees

11 Oct - 12 Oct

A covered outdoor seating area with brick flooring and metal railings, overlooking a river.

A hotel entrance with a covered walkway, large windows, and a clear sign indicating a 10-foot clearance.

A spacious living area with a sofa, coffee table, and a view of the outdoors through large windows.

A hotel lobby with a striped sofa, a reception desk, and a check-in counter.

16. Best Western Plus The Inn & Suites At The Falls

Red Oaks Mill

Aixa

฿4,362

฿4,935 total

includes taxes & fees

20 Sept - 21 Sept

A long dining table set for a meal with chairs, large windows, and a view of a park.

A modern lounge area with seating, tables, and a large vase.

A modern lobby with a blue sofa, marble coffee table, and a reception desk with a blackboard.

A modern building with large glass windows, a covered walkway, and outdoor seating.

17. The Heartwood

Arlington

Graham

฿4,263

฿4,951 total

includes taxes & fees

4 Oct - 5 Oct

A modern kitchen with dark cabinets, a stainless steel microwave, and a white countertop.

A spacious lobby with a reception desk, seating area, and a chandelier.

A stone fireplace with a fire, a painting above it, and a sofa with a plant in front.

A bar area with wooden cabinets, a flat-screen TV, and blue upholstered chairs.

18. HYATT house Fishkill/Poughkeepsie

Fishkill

Myles

฿4,330

฿5,006 total

includes taxes & fees

4 Oct - 5 Oct

A hotel room with two beds, a desk, a television, and a microwave.

A gym with exercise equipment, a mirror, and a rack of dumbbells.

A reception area with a desk, a bench, a staircase, and a fire extinguisher.

A laundry room with two front-loading washing machines and a countertop with a coffee maker.

19. Red Roof Inn PLUS+ Poughkeepsie

Crown Heights

Lee

฿2,809

฿3,262 total

includes taxes & fees

14 Sept - 15 Sept

An outdoor patio area with a stone fire pit, seating, and a Marriott sign in the background.

A modern hotel room with a large bed, a desk, and a chair. There is a window with curtains, a wall-mounted lamp, and a mirror.

A hotel with multiple buildings, a parking lot, and a body of water in the foreground.

A spacious lobby with a fireplace, comfortable seating, and a high ceiling with skylights.

20. SpringHill Suites by Marriott Fishkill

Fishkill

Aleksandar

฿5,731

฿6,626 total

includes taxes & fees

27 Sept - 28 Sept

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Stay near popular Highland attractions

Franny Reese State Park

Traverse historic carriage roads and discover 19th-century mansion ruins at this serene riverside park. Hike through lush forests to reach stunning Hudson River overlooks and panoramic views of the Mid-Hudson Bridge.

See properties

Apple Greens Golf Course

8.8/10 (3 reviews)

This 27-hole Hudson Valley course offers challenging play amid stunning Catskill and Shawangunk Mountain views. Arrive early to enjoy the driving range and putting greens before your round.

See properties

Berean Park Beach

Berean Park Beach offers a serene sandy shoreline with picnic facilities and hiking trails in Highland, New York. Families can enjoy swimming, tennis courts, and the playground during summer months.

See properties

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.

See all hotels in Highland

A suspension bridge over a river with hills in the background.

Top Highland Hotel Reviews

SureStay Plus Hotel by Best Western Highland Poughkeepsie

8/10 Good

"Fairly new, fairly clean Convenient location."

Residence Inn by Marriott Kingston

10/10 Excellent

"Nice"

Hyatt Place Poughkeepsie / Hudson Valley

10/10 Excellent

"Very nice property. Only downside is that you cannot walk anywhere. There are no sidewalks on the main road."

Courtyard by Marriott Kingston

10/10 Excellent

"Loved everything about this hotel. Exceeded my expectations. Would stay again."

Ramada by Wyndham Newburgh/West Point

10/10 Excellent

"Non"

The Thayer Hotel at West Point

10/10 Excellent

"Wonderful!"

Quality Inn Hyde Park Poughkeepsie North

8/10 Good

"The staff was always very helpful when needed. The breakfast was good. And the location could not be beat for all the attractions you would want to visit in the area."

Hampton Inn by Hilton New Paltz

8/10 Good

"We had a beautiful time at Hampton Inn. The only trouble we had, was whoever was staying in the room above us was terribly loud. It had nothing to do with the hotel though. The staff were kind and friendly and accommodating. The pool was nice, wish it was a bit warmer, but that's just me. Wonderful time! This was our 4th time staying at this hotel. Close to shops, restaurants, and Minnewaska State Park for hiking. We will be back soon!"

Holiday Inn Express Poughkeepsie by IHG

8/10 Good

"Parking was super easy with plenty of spaces available at the entrances. The room was clean and relatively quiet. Because the hotel is off the highway there wasn't a lot of road noise. The hallways show a lot of wear and tear but if you get past this aspect and into your room all is acceptable."

More cheap stays in Highland

Quality Inn Hyde Park Poughkeepsie North

4142 Albany Post Rd Hyde Park NY

฿2,804

฿3,172 total

12 Oct - 13 Oct

includes taxes & fees

8/10 Very good! (1,002 reviews)

SureStay Plus Hotel by Best Western Highland Poughkeepsie

3423 US Highway 9W Highland NY

฿2,949

฿3,303 total

20 Sept - 21 Sept

includes taxes & fees

8/10 Very good! (1,002 reviews)

Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point

915 Union Ave New Windsor NY

฿2,944

฿3,478 total

27 Sept - 28 Sept

includes taxes & fees

8.4/10 Very good! (1,002 reviews)

Holiday Inn Express Poughkeepsie by IHG

2750 South Road Poughkeepsie NY

฿3,206

฿3,723 total

4 Oct - 5 Oct

includes taxes & fees

8.8/10 Excellent! (1,003 reviews)

Comfort Suites Fishkill near Interstate 84

835 Route 52 Fishkill NY

฿3,583

฿4,143 total

14 Oct - 15 Oct

includes taxes & fees

9.2/10 Wonderful! (1,007 reviews)

Hampton Inn by Hilton New Paltz

4 South Putt Corners Road New Paltz NY

฿4,309

฿4,826 total

21 Sept - 22 Sept

includes taxes & fees

9.4/10 Exceptional! (1,002 reviews)

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 Beekman Arms and Delamater Inn and Holiday Inn Express Poughkeepsie by IHG. See all available top hotels, or 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?

Hyatt Place Poughkeepsie / Hudson Valley: Features a snack bar/deli, an indoor pool and free self parking. Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point and Wildflower Farms, Auberge Collection 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 47 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 Franny Reese State Park and Apple Greens Golf Course. 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.

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Book Hotels in Highland on Expedia.com

Find hotels in Highland, NY from ฿3,172

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in Highland

Check prices for these dates

Filter by

Star rating

Guest rating

Our top choices for Highland hotels

1. SureStay Plus Hotel by Best Western Highland Poughkeepsie

2. Hyatt Place Poughkeepsie / Hudson Valley

3. Holiday Inn Express Poughkeepsie by IHG

4. Hampton Inn & Suites Poughkeepsie

5. Inn at Bellefield / Hyde Park, Residence Inn by Marriott

6. Home2 Suites By Hilton Poughkeepsie

7. DoubleTree by Hilton Poughkeepsie Convention Center

8. Americas Best Value Inn New Paltz

9. Hampton Inn by Hilton New Paltz

10. Residence Inn by Marriott Poughkeepsie

11. Courtyard by Marriott Poughkeepsie

12. Homewood Suites by Hilton Poughkeepsie

13. Quality Inn Hyde Park Poughkeepsie North

14. Holiday Inn Poughkeepsie by IHG

15. Quality Inn Poughkeepsie

16. Best Western Plus The Inn & Suites At The Falls

17. The Heartwood

18. HYATT house Fishkill/Poughkeepsie

19. Red Roof Inn PLUS+ Poughkeepsie

20. SpringHill Suites by Marriott Fishkill

Stay near popular Highland attractions

Franny Reese State Park

Apple Greens Golf Course

Berean Park Beach

Learn more about Highland

Top Highland Hotel Reviews

SureStay Plus Hotel by Best Western Highland Poughkeepsie

Residence Inn by Marriott Kingston

Hyatt Place Poughkeepsie / Hudson Valley

Courtyard by Marriott Kingston

Ramada by Wyndham Newburgh/West Point

The Thayer Hotel at West Point

Quality Inn Hyde Park Poughkeepsie North

Hampton Inn by Hilton New Paltz

Holiday Inn Express Poughkeepsie by IHG

More cheap stays in Highland

Quality Inn Hyde Park Poughkeepsie North

SureStay Plus Hotel by Best Western Highland Poughkeepsie

Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point

Holiday Inn Express Poughkeepsie by IHG

Comfort Suites Fishkill near Interstate 84

Hampton Inn by Hilton New Paltz

Frequently asked questions

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