Poughkeepsie Holiday Homes from €115: Search Top House Rentals

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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 kitchen with a marble countertop, wooden cabinets, and a dining area with a glass table and stools.

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 €368

€368

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 modern kitchen with stainless steel appliances, white cabinetry, and a wooden countertop.

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 €633

€633

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.

A spacious living area with a wooden dining table, chairs, a large rug, and a ceiling fan.

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.

The price is €512

€512

includes taxes & fees

29 Sept - 30 Sept

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

A living room with hardwood flooring, a sofa, a patterned rug, a flat-screen TV mounted on the wall, and a sliding glass door leading to a balcony.

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

Amazing 3-bedroom house with AC in adorable Highland

Highland

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

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

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

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

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 €319

€319

includes taxes & fees

28 Oct - 29 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

Hudson Escape W/ Hot Tub + Bridge View

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

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

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

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.

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.

Chestnut on Willow Lake

A staircase with wooden steps and white walls, leading to a landing with a window and two potted plants.

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.

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 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.

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 €115

€115

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 wooden cabin with a metal roof, surrounded by a grassy yard with a fire pit and red Adirondack chairs.

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 €253

€253

includes taxes & fees

22 Oct - 23 Oct

The Studio at the Inn at High Falls

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

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

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

A compact kitchen with a dining area, a TV, and a window with a view of greenery.

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 €241

€241

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 €228

€228

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

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

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

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 €355

€355

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 modern kitchen with white cabinets, a wooden dining table, and a red and white checkered window treatment.

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 €395

€395

includes taxes & fees

6 Oct - 7 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 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.

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 €253

€253

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 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.

A cabin in a forest with snow on the ground.

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 €250

€250

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 modern kitchen with white cabinets, a stainless steel refrigerator, a microwave, and a gas stove.

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

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

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 €242

€242

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

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

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 €355

€355

includes taxes & fees

28 Sept - 29 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 wooden sign for Minnewaska State Park Preserve with a stone base.

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 €137

€137

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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