New Windsor Vacation Homes

New Windsor Vacation Homes
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Our top choices for New Windsor holiday homes

A modern kitchen with white cabinets, a marble countertop, and a built-in oven.

A living room with a flat-screen TV mounted on the wall, a wooden cabinet below, a potted plant, and a wicker basket.

A dark wooden cabinet with woven doors, a welcome sign, a framed sketch, and a small vase with dried flowers.

A minimalist bedroom with a bed, a wall-mounted TV, a potted plant, and a window.

1. Hudson View Hot Tub · Walk to Waterfront

Hudson View Hot Tub · Walk to Waterfront

Newburgh

10.0 out of 10, Exceptional, (1 review)

10/10

Exceptional

(1 review)

"The home has recently been renovated and it is very well presented with luxury furnishings and an excellently stocked kitchen. Views are amazing over the Hudson towards Beacon."

Rachel M.

The price is HK$2,854

HK$2,854

HK$6,821 total

includes taxes & fees

25 Oct - 26 Oct

Hudson View Hot Tub · Walk to Waterfront

A modern kitchen with white cabinets, a central island, bar stools, and a stainless steel dishwasher.

A kitchen with wooden cabinets, a stainless steel refrigerator, and a coffee maker.

A sofa with three pillows, a plant, and a framed artwork on the wall.

A bedroom with a bed, bedside table, lamp, and a painting on the wall.

2. House + Suite · Hudson View Hot Tub

House + Suite · Hudson View Hot Tub

Newburgh

10.0 out of 10, Exceptional, (1 review)

10/10

Exceptional

(1 review)

House + Suite · Hudson View Hot Tub

3. Luxury Hudson Valley Retreat near West Point, Storm King & Beacon

Luxury Hudson Valley Retreat near West Point, Storm King & Beacon

Cornwall

9.0 out of 10, Wonderful, (2 reviews)

9.0/10

Wonderful

(2 reviews)

"Great House, less than 15 mins to front gate at West Point, convenient location for visiting and enjoying activities at West Point, e.g. football games, cadet events for family members, etc. Hope to be able to stay there again on another visit to the "Rockbound Highland Home"!!! "

Jeff M.

The price is HK$3,644

HK$3,644

HK$7,563 total

includes taxes & fees

27 Oct - 28 Oct

Luxury Hudson Valley Retreat near West Point, Storm King & Beacon

A bed in a tent-like room with a view of trees through a window.

A staircase with red carpeted steps, wooden handrails, and string lights.

A room with a large window overlooking a forested area.

A kitchen with wooden cabinets, a stainless steel refrigerator, and a window above the sink.

4. Large,Cozy,Bright Apartment, Business Themed.

Large,Cozy,Bright Apartment, Business Themed.

Newburgh

9.0 out of 10, Wonderful, (17 reviews)

9.0/10

Wonderful

(17 reviews)

"Very cozy stay with responsive host"

Adhith P.

The price is HK$3,605

HK$3,605

HK$4,832 total

includes taxes & fees

13 Nov - 14 Nov

Large,Cozy,Bright Apartment, Business Themed.

A two-story house with a porch, a red door, and a small outdoor seating area with chairs and a table.

A bed with a quilted headboard and a stack of folded towels.

A staircase with carpeted steps and wooden handrails, leading to a door with glass panels.

A living room with a ceiling fan, a flat-screen TV, a coffee table, a sofa, and a window with a view.

5. House on the Babbling Brook- Quiet 2BR + King Bed!

House on the Babbling Brook- Quiet 2BR + King Bed!

Highland Falls

9.8 out of 10, Exceptional, (14 reviews)

9.8/10

Exceptional

(14 reviews)

"We had a very comfortable stay. Nice quaint village. Area was quiet and easy to get to."

Leann M.

The price is HK$1,011

HK$1,011

HK$3,243 total

includes taxes & fees

27 Oct - 28 Oct

House on the Babbling Brook- Quiet 2BR + King Bed!

A deck with Adirondack chairs, a fire pit, and a grill.

A modern kitchen with white cabinets, a dishwasher, a stove, and a window overlooking a wooded area.

A wooden staircase with a handrail, leading to a room with a bench and a table.

A two-story house with a stone pathway leading to the front door, surrounded by autumn foliage.

6. 3BR Home with Fireplace & Hudson Valley views near Woodbury Commons, West Point

3BR Home with Fireplace & Hudson Valley views near Woodbury Commons, West Point

Cornwall

10.0 out of 10, Exceptional, (16 reviews)

10/10

Exceptional

(16 reviews)

"Everything you could ask for!!"

Elisabeth

The price is HK$1,708

HK$1,708

HK$3,416 total

includes taxes & fees

3 Nov - 4 Nov

3BR Home with Fireplace & Hudson Valley views near Woodbury Commons, West Point

A house with a white front door, a small porch with a white railing, and a window with a green curtain.

A house with a wooden deck, a white railing, and a front door.

A wooden staircase with a white handrail, leading upwards.

A kitchen with dark cabinets, a white tiled backsplash, a blue microwave, a stainless steel faucet, and a coffee maker.

7. Fabulous 3bdrm Home w/parking!

Fabulous 3bdrm Home w/parking!

Highland Falls

9.4 out of 10, Exceptional, (12 reviews)

9.4/10

Exceptional

(12 reviews)

"House was exactly as described. Would stay again."

Beth M.

The price is HK$1,810

HK$1,810

HK$3,177 total

includes taxes & fees

17 Nov - 18 Nov

Fabulous 3bdrm Home w/parking!

An outdoor patio area with a covered seating area, a pool, and potted plants.

A dimly lit interior with a large TV screen displaying a video, a small table with a chair, and a fireplace.

A cozy living room with a large screen, comfortable seating, and a fireplace.

A compact kitchen with a dining area, featuring a stove, pots, and a sink.

8. Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo

Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo

Fishkill

9.2 out of 10, Wonderful, (81 reviews)

9.2/10

Wonderful

(81 reviews)

"The property was as advertised and met our needs for our trip."

Sara

The price is HK$2,050

HK$2,050

HK$2,688 total

includes taxes & fees

28 Oct - 29 Oct

Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo

A bedroom with a bed, a ceiling fan, a nightstand, a window with curtains, and a wall with framed pictures.

A walk-in closet with open shelves, hanging space, and a bench.

A living room with a sofa, coffee table, and a dining area with chairs and a table.

A modern kitchen with a wooden table and chairs, a stainless steel refrigerator, and a white cabinet.

9. Sleek Escape: Modern 3 BR- 4 Min from West Point !

Sleek Escape: Modern 3 BR- 4 Min from West Point !

Highland Falls

9.4 out of 10, Exceptional, (8 reviews)

9.4/10

Exceptional

(8 reviews)

"Great location and super host. "

James U.

The price is HK$1,411

HK$1,411

HK$3,949 total

includes taxes & fees

1 Nov - 2 Nov

Sleek Escape: Modern 3 BR- 4 Min from West Point !

A blue house with a white porch, a welcome sign, and a mailbox.

A traditional wood-burning stove with intricate carvings, a decorative tiled base, and a stone wall backdrop.

A kitchen with wooden cabinets, a granite countertop, a stove, and a window with a plant.

A blue house with a white porch, a welcome sign, and a covered window.

10. 3BR West Point Retreat-3min to Back Gate+ King Bed

3BR West Point Retreat-3min to Back Gate+ King Bed

Highland Falls

8.4 out of 10, Very good, (7 reviews)

8.4/10

Very good

(7 reviews)

"Space was excellent, the multiple bedrooms with the extra bathroom was great. Kitchen was stocked with utensils, bathrooms were clean, living space was comfortable and cozy."

Christine T.

The price is HK$1,318

HK$1,318

HK$4,153 total

includes taxes & fees

27 Oct - 28 Oct

3BR West Point Retreat-3min to Back Gate+ King Bed

A room with a wooden floor, a white door with a number, and a window with blinds.

A wooden deck with white railings, leading to a white building with a brown roof.

A wooden staircase with a handrail, leading upwards.

A modern kitchen with wooden cabinets, a stainless steel refrigerator, a dishwasher, a microwave, and a coffee maker.

11. Lovely 3BR Home with parking-Walk to WP Gate!

Lovely 3BR Home with parking-Walk to WP Gate!

Highland Falls

10.0 out of 10, Exceptional, (7 reviews)

10/10

Exceptional

(7 reviews)

"Lovely home, great location and space for my family to have privacy. Enjoyed the deck for morning coffee. Would book again. "

Briana T.

The price is HK$1,679

HK$1,679

HK$3,091 total

includes taxes & fees

17 Nov - 18 Nov

Lovely 3BR Home with parking-Walk to WP Gate!

A two-story house with a front porch and a landscaped garden.

A bathroom with a patterned tile wall, a shower curtain, and a shelf with toiletries.

A rural landscape with a barn, a silo, and a bridge with rocks and purple flowers in the foreground.

A rural landscape with a barn, a silo, and a field of purple flowers.

12. A Cozy Private Suite Near New Paltz: Farms, Nature, Hiking & Bike the rail trail

A Cozy Private Suite Near New Paltz: Farms, Nature, Hiking & Bike the rail trail

Wallkill

9.2 out of 10, Wonderful, (18 reviews)

9.2/10

Wonderful

(18 reviews)

"The room was super cute and clean. It had everything that I needed."

Carrie

The price is HK$564

HK$564

HK$1,115 total

includes taxes & fees

28 Oct - 29 Oct

A Cozy Private Suite Near New Paltz: Farms, Nature, Hiking & Bike the rail trail

A rustic cabin with a chimney, surrounded by dense autumn foliage and a narrow road.

A cozy room with wicker furniture, a bench, and a window with a view of greenery.

A grand piano in a room with a window, a small stool, and a wooden bench.

A cemetery with stone headstones and a stone wall, surrounded by trees with autumn leaves.

13. Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park

Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park

Hopewell Junction

9.4 out of 10, Exceptional, (13 reviews)

9.4/10

Exceptional

(13 reviews)

"Lovely space and situation, unique. Close to the AT, as well."

Peter W.

The price is HK$1,324

HK$1,324

HK$2,207 total

includes taxes & fees

25 Oct - 26 Oct

Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park

A stone house with a steeply pitched roof, surrounded by a well-maintained lawn and trees.

A small, sloped ceiling room with a bed, a chair, a dresser, and a skylight.

A lakeside seating area with Adirondack chairs arranged around a central fire pit.

A kitchen with wooden cabinets, a refrigerator, a stove, and a microwave.

14. Chestnut on Willow Lake

Chestnut on Willow Lake

Fishkill

9.8 out of 10, Exceptional, (6 reviews)

9.8/10

Exceptional

(6 reviews)

"Our family enjoyed a relaxing weekend before R-day at West Point and it was perfect! A beautiful property and we hope to be back another time!"

Quintina R.

The price is HK$3,017

HK$3,017

HK$4,210 total

includes taxes & fees

22 Nov - 23 Nov

Chestnut on Willow Lake

A compact kitchen with dark wooden cabinets, a white stove, a white refrigerator, and a built-in washer and dryer.

A red cabin with a gravel path leading to it, surrounded by greenery and trees.

15. Red Cottage - Lakeside Property!

Red Cottage - Lakeside Property!

Fishkill

The price is HK$2,155

HK$2,155

HK$3,305 total

includes taxes & fees

22 Nov - 23 Nov

Red Cottage - Lakeside Property!

A modern living room with a grey sofa, a coffee table, and a TV mounted on a stone wall.

A dimly lit room with a bed, a nightstand, and a wall-mounted light fixture.

A living room with a stone wall, a mounted guitar, a flat-screen TV, and two grey sofas.

16. complete privacy vacation home [private pool]

complete privacy vacation home [private pool]

Newburgh

9.0 out of 10, Wonderful, (17 reviews)

9.0/10

Wonderful

(17 reviews)

"oh my god the best place it feels like home"

Phelicia G.

The price is HK$5,325

HK$5,325

HK$9,299 total

includes taxes & fees

27 Oct - 28 Oct

complete privacy vacation home [private pool]

A modern kitchen with white cabinets, a marble countertop, and a stainless steel range hood.

A living room with a large artificial tree, several potted plants, and a dining area with chairs and a table.

A modern living room with a flat-screen TV mounted above a fireplace, two grey sofas with cushions, a glass coffee table with decorative items, and a potted plant.

A neatly arranged bedroom with a large bed, a bedside table with a lamp, and a chair.

17. Contemporary Cozy Cottage

Contemporary Cozy Cottage

Lake Peekskill

9.8 out of 10, Exceptional, (41 reviews)

9.8/10

Exceptional

(41 reviews)

"Our stay was very nice and described as listed! We recommend anyone who is interested to stay! "

Aj L.

The price is HK$1,763

HK$1,763

HK$3,316 total

includes taxes & fees

25 Oct - 26 Oct

Contemporary Cozy Cottage

A tent with a central pole, a view of the forest through the entrance, and a bed with patterned bedding.

A forest campsite with a tent, a fire pit, and a bench.

A wooden sign for Minnewaska State Park Preserve with a stone base.

18. Glamping Tent & Campsite by Minnewaska State Park

Glamping Tent & Campsite by Minnewaska State Park

Kerhonkson

9.0 out of 10, Wonderful, (4 reviews)

9.0/10

Wonderful

(4 reviews)

"This place was amazing and our hosts were as equally as awesome as their campsite. My family highly recommends this place! It's got everything you need and is close to so many beautiful hiking and swimming areas!"

Andie C.

The price is HK$670

HK$670

HK$1,189 total

includes taxes & fees

25 Oct - 26 Oct

Glamping Tent & Campsite by Minnewaska State Park

A kitchen with a coffee maker, toaster, and two mugs on a marble countertop.

A modern kitchen with stainless steel appliances, a marble countertop, and a dining area with white chairs.

A modern kitchen with white cabinets, stainless steel appliances, and a wooden floor.

A bedroom with a bed, a nightstand, a window, and a wall-mounted picture.

19. Hudson Valley/West Point Retreat w/ parking!

Hudson Valley/West Point Retreat w/ parking!

Highland Falls

The price is HK$1,785

HK$1,785

HK$3,286 total

includes taxes & fees

26 Oct - 27 Oct

Hudson Valley/West Point Retreat w/ parking!

A fire pit with four Adirondack chairs arranged around it, set on a gravel surface with a lake and trees in the background.

A modern living room with a grey sofa, a coffee table, a TV, and a lamp.

A neatly arranged bedroom with a bed, bedside lamps, a round mirror, and a framed picture on the wall.

A room with a wooden cabinet with glass doors, a patterned rug, a woven basket, and a small wooden stool.

20. Luxe Waterfront Retreat w/ Infrared Sauna & Red Light. Near New Paltz

Luxe Waterfront Retreat w/ Infrared Sauna & Red Light. Near New Paltz

wallkill

9.8 out of 10, Exceptional, (61 reviews)

9.8/10

Exceptional

(61 reviews)

"Had a wonderful time! Loved our stay at this beautiful river front property!"

Debbie M.

The price is HK$1,386

HK$1,386

HK$3,026 total

includes taxes & fees

26 Oct - 27 Oct

Luxe Waterfront Retreat w/ Infrared Sauna & Red Light. Near New Paltz

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.

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Top New Windsor Hotel Reviews

Comfort Suites Fishkill near Interstate 84

10/10 Excellent

"The room was clean The staff were helpful. My key didn’t unlock the door one night but the staff fixed it with no problems. Breakfast was good but was the exact same menu for each day The air conditioning system worked"

Dawn 2-night trip

Posted 13 hours ago

Comfort Suites Fishkill near Interstate 84

DoubleTree by Hilton Poughkeepsie Convention Center

10/10 Excellent

"Friendly accommodating staff. Very clean beautiful river-view room. Free parking. Convenient to everything."

Barbara 2-night trip

Posted 13 hours ago

DoubleTree by Hilton Poughkeepsie Convention Center

The Heartwood

10/10 Excellent

"Lovely, well appointed clean and comfortable room. Staff pleasant and helpful. The place to rest and relax in Poughkeepsie-Hyde Park area."

William 1-night trip

Posted 21 hours ago

The Heartwood

La Quinta Inn & Suites by Wyndham Middletown-Goshen

10/10 Excellent

"Nice, laid back hotel with great staff."

William 4-night trip

Posted 2 days ago

La Quinta Inn & Suites by Wyndham Middletown-Goshen

Holiday Inn Express Poughkeepsie by IHG

10/10 Excellent

"Excellent place—nice room and fine breakfast"

Norman 1-night trip

Posted 2 days ago

Holiday Inn Express Poughkeepsie by IHG

Inn on the Hudson

8/10 Good

"Slightly dated hotel walkable into the town centre have used before and would use again"

Paul 1-night trip

Posted 2 days ago

Inn on the Hudson

Ramada by Wyndham Newburgh/West Point

8/10 Good

"Was under construction, room was clean and comfortable."

Gary 4-night trip

Posted 3 days ago

Ramada by Wyndham Newburgh/West Point

The Thayer Hotel at West Point

10/10 Excellent

"It is a true honor to stay at such a magnificent hotel with such a rich history. It would be fascinating to learn the unique story behind each room."

Jane 1-night trip

Posted 5 days ago

The Thayer Hotel at West Point

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