Poughkeepsie Holiday House Rentals from AU$182: Search Holiday Homes

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Our top choices for Poughkeepsie holiday homes

A modern kitchen with a granite countertop, a built-in stove, and a dining area with a glass table and chairs.

A wooden staircase with a black railing leading to a door with a decorative glass panel.

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

A room with large windows, a black leather sofa, and wooden flooring.

1. Stunning 5-bedroom house with AC / Heat in charming Poughkeepsie NY

Stunning 5-bedroom house with AC / Heat in charming Poughkeepsie NY

Poughkeepsie

9.6 out of 10, Exceptional, (5 reviews)

9.6/10

Exceptional

(5 reviews)

"Beautiful property with ample space for parking. Host was super nice and met all of our needs!"

Nicole Y.

The price is AU$608

AU$608

includes taxes & fees

28 Sept - 29 Sept

Stunning 5-bedroom house with AC / Heat in charming Poughkeepsie NY

A spacious living area with a staircase, a dining table, and a sofa.

A spacious living room with a grey sofa, a black ottoman, and a wooden piano.

A covered porch with wooden flooring, a white railing, and a door with glass panels.

2. Our home is perfect for relaxing and having lots of fun, with near by activity’s

Our home is perfect for relaxing and having lots of fun, with near by activity’s

Highland

9.6 out of 10, Exceptional, (13 reviews)

9.6/10

Exceptional

(13 reviews)

"We had was great time and the host Mary was amazing and excellent at communicating. Everything was perfect in the home. Thank you"

Pinal

The price is AU$1,027

AU$1,027

includes taxes & fees

29 Sept - 30 Sept

Our home is perfect for relaxing and having lots of fun, with near by activity’s

A staircase leading to a second floor, a sofa with a throw blanket, a floor lamp, a small table with a vase of sunflowers, and a kitchen area visible through an archway.

A living room with a sofa, a round wooden coffee table, a fireplace, and a bookshelf.

An outdoor deck with a table set for dining, a barbecue grill, and a large umbrella providing shade.

3. Chilly Days Hiking, Quiet Yard, an Easy Escape Near New Paltz

Chilly Days Hiking, Quiet Yard, an Easy Escape Near New Paltz

New Paltz

10.0 out of 10, Exceptional, (8 reviews)

10/10

Exceptional

(8 reviews)

"Superb property - comfortable, spotless, all the amenities you could need, and lots of space. "

Thomas B.

Chilly Days Hiking, Quiet Yard, an Easy Escape Near New Paltz

A modern kitchen with white cabinets, a built-in toaster, a blender, and a window with a view of trees.

A wooden deck with a table and chairs, a sofa, and a railing.

A kitchen with white cabinets, a countertop, a toaster, and a blender.

A bedroom with a bed, bedside table, lamp, and a view through a window.

4. Amazing 3-bedroom house with AC in adorable Highland

Amazing 3-bedroom house with AC in adorable Highland

Highland

The price is AU$771

AU$771

includes taxes & fees

29 Sept - 30 Sept

Amazing 3-bedroom house with AC in adorable Highland

A covered outdoor area with a barbecue grill and a hot tub.

A dining area with a wooden table, chairs, and vases with pampas grass.

A dining area with a long wooden table, three black vases with dried pampas grass, and a woven placemat.

A spacious living area with a high ceiling, a staircase, a dining area, and a large window providing natural light.

5. Scenic New Paltz Escape: River Views, Hot Tub & Deck | Dream House in the Gunks

Scenic New Paltz Escape: River Views, Hot Tub & Deck | Dream House in the Gunks

New Paltz

9.6 out of 10, Exceptional, (40 reviews)

9.6/10

Exceptional

(40 reviews)

"Exactly as listed, great property and host."

Neil C.

Scenic New Paltz Escape: River Views, Hot Tub & Deck | Dream House in the Gunks

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

A bedroom with a bed, a desk, a chair, a television, and a wardrobe.

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.

6. 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, (78 reviews)

9.2/10

Wonderful

(78 reviews)

"It’s was nice, clean and the outdoor out area was really nice."

Roger S.

The price is AU$487

AU$487

includes taxes & fees

30 Sept - 1 Oct

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

7. Hudson Escape W/ Hot Tub + Bridge View

Hudson Escape W/ Hot Tub + Bridge View

Highland

The price is AU$1,338

AU$1,338

includes taxes & fees

1 Oct - 2 Oct

Hudson Escape W/ Hot Tub + Bridge View

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

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

A spacious loft with a high ceiling, a staircase to an upper level, a dining area with a table and chairs, and a cozy seating area with a sofa and a coffee table.

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

8. Chestnut on Willow Lake

Chestnut on Willow Lake

Fishkill

9.8 out of 10, Exceptional, (6 reviews)

9.8/10

Exceptional

(6 reviews)

"We really enjoyed the privacy of the grounds, lake, dock , swimming, boats and paddle boards. The kitchen was well equipped and the beds were comfy. We had a great stay, thanks."

Doria W.

The price is AU$1,023

AU$1,023

includes taxes & fees

28 Sept - 29 Sept

Chestnut on Willow Lake

A narrow hallway with a tiled floor, a white door, a black bench, and a window leading to a kitchen area.

A gazebo with a stone base and wooden structure, surrounded by a grassy area and trees.

9. Hickory on Willow Lake

Hickory on Willow Lake

Fishkill

9.8 out of 10, Exceptional, (6 reviews)

9.8/10

Exceptional

(6 reviews)

"Clean, quiet and great location. Beautiful property."

Sheila B.

The price is AU$1,114

AU$1,114

includes taxes & fees

28 Sept - 29 Sept

Hickory on Willow Lake

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.

A bedroom with a bed, nightstands, a dresser, and a chair.

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

10. 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, (15 reviews)

9.2/10

Wonderful

(15 reviews)

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

Carrie

The price is AU$182

AU$182

includes taxes & fees

29 Sept - 30 Sept

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

A bedroom with a bed, a TV mounted on the wall, a window with a view of greenery, and a small seating area with a table and chairs.

A bathroom with a white sink, a mirror, and a window.

A wooden cabin with a red roof, surrounded by lush greenery and orange flowers.

A glass-enclosed shower with a metal handle and a white bathtub.

11. The Studio at the Inn at High Falls

The Studio at the Inn at High Falls

High Falls

8.0 out of 10, Very good, (46 reviews)

8.0/10

Very good

(46 reviews)

"The pictures are misleading"

Jia

The price is AU$388

AU$388

includes taxes & fees

28 Sept - 29 Sept

The Studio at the Inn at High Falls

A modern kitchen with a granite countertop, stainless steel appliances, and a built-in oven.

A kitchen with a dining area, wooden flooring, a ceiling fan, and a window with blinds.

A bedroom with a bed, a chair with a yellow cushion, a potted plant, and a window with curtains.

A modern kitchen with white cabinets, a built-in oven, and a dining area with a black rug and metal chairs.

12. Campfire Cottage: Fireplace, fire pit & no chores!

Campfire Cottage: Fireplace, fire pit & no chores!

Kingston

10.0 out of 10, Exceptional, (33 reviews)

10/10

Exceptional

(33 reviews)

"Great multi-week stay! Would certainly stay again. "

Jim R.

The price is AU$382

AU$382

includes taxes & fees

28 Sept - 29 Sept

Campfire Cottage: Fireplace, fire pit & no chores!

A wooden deck with a wood-burning stove and a door leading to an outdoor area with chairs.

A living room with a sofa, a small table, a fireplace, a staircase, and a painting on the wall.

A kitchen with wooden countertops, a dining table, and chairs. There are jars and cups on the counter.

13. Historic Hudson Valley Farmhouse w/ Sauna in Stone Ridge Hamlet

Historic Hudson Valley Farmhouse w/ Sauna in Stone Ridge Hamlet

Stone Ridge

10.0 out of 10, Exceptional, (4 reviews)

10/10

Exceptional

(4 reviews)

"Very convenient and welcoming. Perfect place for a quick stop over."

Jenna H.

The price is AU$382

AU$382

includes taxes & fees

19 Oct - 20 Oct

Historic Hudson Valley Farmhouse w/ Sauna in Stone Ridge Hamlet

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

A two-story house with a porch, a flag, and a fenced yard.

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

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

14. 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, (12 reviews)

9.8/10

Exceptional

(12 reviews)

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

Leann M.

The price is AU$565

AU$565

includes taxes & fees

28 Sept - 29 Sept

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

A living room with a sofa, a coffee table, a wooden chair, a striped rug, and a wall-mounted wreath.

A bedroom with a bed, a dresser, and a door.

A white house with a porch, a stone pathway, and a grassy yard.

A living room with a sofa, a coffee table, an orange chair, a potted plant, and a painting on the wall.

15. The DeVita House Est. 1900

The DeVita House Est. 1900

Gardiner

10.0 out of 10, Exceptional, (41 reviews)

10/10

Exceptional

(41 reviews)

"Great house, well equipped, very accommodating hosts!"

Christopher T.

The price is AU$622

AU$622

includes taxes & fees

5 Oct - 6 Oct

The DeVita House Est. 1900

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

A rustic cabin with a stone pathway leading to a red chair outside.

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

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

16. 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 AU$398

AU$398

includes taxes & fees

28 Sept - 29 Sept

Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park

A modern living room with a fireplace, a dining area with a wooden table, and a large window with curtains.

A cabin in a forest with snow on the ground.

A hotel room with a bed, a wall-mounted decorative piece, and a view into the dining area.

A modern living room with a stone fireplace, a wooden bench with a plant, and a large window with a view of trees.

17. Zen House at the Mountain Ridge

Zen House at the Mountain Ridge

Gardiner

9.8 out of 10, Exceptional, (9 reviews)

9.8/10

Exceptional

(9 reviews)

"Great space! Very nicely decorated. Host was very responsive and answered questions quickly. Also close to a great bakery and coffee shop!"

Julie

The price is AU$397

AU$397

includes taxes & fees

1 Oct - 2 Oct

Zen House at the Mountain Ridge

A view from a room with a sliding glass door leading to an outdoor deck with a wooden fence, a chair, and a bench.

A bedroom with a bed, a TV on a white dresser, a window with blinds, and a ceiling light fixture.

A kitchen with white cabinets, a granite countertop, a stainless steel sink, and a window with a view of trees.

A compact kitchen with a stainless steel refrigerator, a bar stool, and a dining area with a red rug.

18. Esopus Creek modern Tiny house Retreat in Woodstock &Kingston Catskill area!

Esopus Creek modern Tiny house Retreat in Woodstock &Kingston Catskill area!

Kingston

9.6 out of 10, Exceptional, (103 reviews)

9.6/10

Exceptional

(103 reviews)

"Wonderful stay. "

Chris L.

The price is AU$383

AU$383

includes taxes & fees

28 Sept - 29 Sept

Esopus Creek modern Tiny house Retreat in Woodstock &Kingston Catskill area!

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

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

A modern kitchen with white cabinets, stainless steel appliances, and a window providing natural light.

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

19. 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, (60 reviews)

9.8/10

Exceptional

(60 reviews)

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

Debbie M.

The price is AU$565

AU$565

includes taxes & fees

29 Sept - 30 Sept

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

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

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

A waterfall cascading into a calm pool surrounded by rocky cliffs and dense greenery.

20. 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 AU$219

AU$219

includes taxes & fees

7 Oct - 8 Oct

Glamping Tent & Campsite by Minnewaska State Park

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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