Poughkeepsie Vacation Homes

An aerial view of a town with a river, a bridge, and autumn-colored trees.

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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.

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

Poughkeepsie

Nicole Y.

HK$3,398 total

includes taxes & fees

13 Oct - 14 Oct

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

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

Highland

Pinal

HK$5,783 total

includes taxes & fees

3 Nov - 4 Nov

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.

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

New Paltz

Thomas B.

HK$5,138 total

includes taxes & fees

13 Oct - 14 Oct

A stone fireplace with a fire, a dining area with a table and chairs, and large windows with a view of trees.

4. NEW: Oaklands Near Shawangunk Mountains

New Paltz

HK$5,071 total

includes taxes & fees

3 Nov - 4 Nov

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

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

Fishkill

Roger S.

HK$2,840 total

includes taxes & fees

28 Oct - 29 Oct

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

6. Hickory on Willow Lake

Fishkill

Sheila B.

HK$4,424 total

includes taxes & fees

1 Nov - 2 Nov

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

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

Wallkill

Carrie

HK$1,046 total

includes taxes & fees

3 Nov - 4 Nov

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.

8. The Studio at the Inn at High Falls

High Falls

Jia

HK$2,140 total

includes taxes & fees

12 Oct - 13 Oct

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

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

Kingston

Jim R.

HK$2,083 total

includes taxes & fees

3 Nov - 4 Nov

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

10. The DeVita House Est. 1900

Gardiner

Christopher T.

HK$3,516 total

includes taxes & fees

13 Oct - 14 Oct

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

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

Hopewell Junction

Peter W.

HK$2,193 total

includes taxes & fees

12 Oct - 13 Oct

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

12. Glamping Tent & Campsite by Minnewaska State Park

Kerhonkson

Andie C.

HK$1,191 total

includes taxes & fees

12 Oct - 13 Oct

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

13. Zen House at the Mountain Ridge

Gardiner

Julie

HK$2,262 total

includes taxes & fees

2 Nov - 3 Nov

A compact kitchen with blue cabinets, a white stove, and yellow chairs.

14. Retro Retreat: 1br home w/ WFH desk, livingroom, fire pit and no chores!

Kingston

Brendan B.

HK$1,942 total

includes taxes & fees

14 Oct - 15 Oct

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

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

Stone Ridge

Tarun

HK$2,400 total

includes taxes & fees

1 Nov - 2 Nov

A hot tub on a wooden deck with a view of a river and trees.

16. Welcome to The Boathouse! Waterfront/Boats/Hot tub

New Paltz

Jessica B.

HK$3,270 total

includes taxes & fees

13 Oct - 14 Oct

A neatly made bed with white bedding and a few colorful pillows, a wooden headboard, and a wall-mounted light fixture.

17. Retro Retreat: renovated 2BR, desk, no chore list!

Kingston

Kelley Marie

HK$2,417 total

includes taxes & fees

2 Nov - 3 Nov

A kitchen with wooden shelves, a window with a view of trees, and a vase with flowers on the windowsill.

18. Relaxed Mountain Living Near Minnewaska | Dream House in the Gunks

Kerhonkson

Sueane

HK$1,717 total

includes taxes & fees

10 Nov - 11 Nov

A kitchen with grey cabinets, a stone floor, and a view of a garden through an open door.

19. Historic Cottage * Steam Shower * Chef’s Kitchen

Kingston

Laura D.

HK$3,909 total

includes taxes & fees

3 Nov - 4 Nov

A wooden gate leading to a driveway with a stone pathway, surrounded by greenery and a house in the background.

20. Maple Ridge Modern Rustic Retreat where Modern comfort meets Rustic Charm

Ulster Park

Emily F.

HK$6,369 total

includes taxes & fees

15 Oct - 16 Oct

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Top Poughkeepsie Hotel Reviews

Holiday Inn Express Poughkeepsie by IHG

8/10 Good

"The place was clean and the breakfast good. It was quite expensive though."

Beekman Arms and Delamater Inn

8/10 Good

"This was my first time at this property. My room was not in the Beekman Arms but in its sister property a few blocks away. The room was large and nicely decorated, it was very clean and the bed was comfortable. The bathroom was very nice and soap, shampoo and towels were supplied in abundance. Breakfast was included and consisted of all sorts of breads, fruit, yogurt, hard boiled eggs, juiced coffee and teas. This was served in a separate building near the residential building Our room was on the third floor so the lack of an elevator pushed my 94 year old body a bit. I would definitely come back to the Beeckman Arms but next time I’ll request a downstairs room."

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