Holiday Homes in Poughkeepsie

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Cabins
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Apartments
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Check prices for these dates

Next weekend
20 Nov - 22 Nov
In two weeks
27 Nov - 29 Nov
In one month
11 Dec - 13 Dec
In two months
8 Jan - 10 Jan

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

Stunning 5-bedroom house with AC / Heat in charming Poughkeepsie NY
Poughkeepsie
9.8 out of 10, Exceptional, (6 reviews)
"Beautiful property with ample space for parking. Host was super nice and met all of our needs!"
United States
Nicole Y.
The price is AU$619
includes taxes & fees
16 Nov - 17 Nov
Stunning 5-bedroom house with AC / Heat in charming Poughkeepsie NY
A modern living room with a fireplace, a sofa, a coffee table, and a chair.

2. Beautiful Modern Villa with Pool

Beautiful Modern Villa with Pool
Clintondale
The price is AU$902
includes taxes & fees
15 Nov - 16 Nov
Beautiful Modern Villa with Pool
A spacious living area with a staircase, a dining table, and a sofa.

3. 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, (14 reviews)
"We had was great time and the host Mary was amazing and excellent at communicating. Everything was perfect in the home. Thank you"
United States
Pinal
The price is AU$976
includes taxes & fees
14 Nov - 15 Nov
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.

4. 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)
"Superb property - comfortable, spotless, all the amenities you could need, and lots of space. "
United States
Thomas B.
The price is AU$891
includes taxes & fees
15 Nov - 16 Nov
Chilly Days Hiking, Quiet Yard, an Easy Escape Near New Paltz
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

Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
Fishkill
9.2 out of 10, Wonderful, (81 reviews)
"The property was as advertised and met our needs for our trip."
United States
Sara
The price is AU$469
includes taxes & fees
15 Nov - 16 Nov
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
A lakeside seating area with Adirondack chairs arranged around a central fire pit.

6. Red Cottage - Lakeside Property!

Red Cottage - Lakeside Property!
Fishkill
The price is AU$573
includes taxes & fees
15 Nov - 16 Nov
Red Cottage - Lakeside Property!
A covered outdoor area with a barbecue grill and a hot tub.

7. 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, (42 reviews)
"Really nice, house. Location was great. There were 8 of us there for a girls weekend. Plenty of room for all.Clean, attentive host, kitchen was well stocked for our needs. Hot tub was great."
United States
Shirley A.
The price is AU$763
includes taxes & fees
13 Dec - 14 Dec
Scenic New Paltz Escape: River Views, Hot Tub & Deck | Dream House in the Gunks
A stone house with a steeply pitched roof, surrounded by a well-maintained lawn and trees.

8. Hickory on Willow Lake

Hickory on Willow Lake
Fishkill
9.8 out of 10, Exceptional, (6 reviews)
"Clean, quiet and great location. Beautiful property."
United States
Sheila B.
The price is AU$769
includes taxes & fees
15 Nov - 16 Nov
Hickory on Willow Lake
A stone house with a steeply pitched roof, surrounded by a well-maintained lawn and trees.

9. Chestnut on Willow Lake

Chestnut on Willow Lake
Fishkill
9.8 out of 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!"
United States
Quintina R.
The price is AU$751
includes taxes & fees
13 Nov - 14 Nov
Chestnut on Willow Lake
A rural landscape with a barn, a silo, and a bridge with rocks and purple flowers in the foreground.

10. A Cozy Private Suite in a Country Home near New Paltz

A Cozy Private Suite in a Country Home near New Paltz
Wallkill
9.2 out of 10, Wonderful, (20 reviews)
"The room was super cute and clean. It had everything that I needed."
United States
Carrie
The price is AU$182
includes taxes & fees
17 Nov - 18 Nov
A Cozy Private Suite in a Country Home near New Paltz
A living room with a sofa, a coffee table, a wooden chair, a striped rug, and a wall-mounted wreath.

11. The DeVita House Est. 1900

The DeVita House Est. 1900
Gardiner
10.0 out of 10, Exceptional, (46 reviews)
"The house was in a perfect location! Host was very easy to communicate with!"
United States
Matthew
The price is AU$636
includes taxes & fees
17 Nov - 18 Nov
The DeVita House Est. 1900
A modern kitchen with a granite countertop, stainless steel appliances, and a built-in oven.

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

Campfire Cottage: Fireplace, fire pit & no chores!
Kingston
10.0 out of 10, Exceptional, (33 reviews)
"Great multi-week stay! Would certainly stay again. "
United States
Jim R.
The price is AU$339
includes taxes & fees
16 Nov - 17 Nov
Campfire Cottage: Fireplace, fire pit & no chores!
A rustic cabin with a chimney, surrounded by dense autumn foliage and a narrow road.

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)
"Lovely space and situation, unique. Close to the AT, as well."
United States
Peter W.
The price is AU$391
includes taxes & fees
25 Nov - 26 Nov
Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park
A wooden deck with a wood-burning stove and a door leading to an outdoor area with chairs.

14. 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, (6 reviews)
"Great tastefully kept property. Our family including the 8 year felt we should have stayed here longer."
United States
Tarun
The price is AU$294
includes taxes & fees
1 Dec - 2 Dec
Historic Hudson Valley Farmhouse w/ Sauna in Stone Ridge Hamlet
A compact kitchen with blue cabinets, a white stove, and yellow chairs.

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

Retro Retreat: 1br home w/ WFH desk, livingroom, fire pit and no chores!
Kingston
10.0 out of 10, Exceptional, (7 reviews)
"Beautiful house to stay in, convenient to numerous restaurants and hikes. Our host was very communicative and had great recommendations for the area!"
United States
Brendan B.
The price is AU$339
includes taxes & fees
16 Nov - 17 Nov
Retro Retreat: 1br home w/ WFH desk, livingroom, fire pit and no chores!
A modern living room with a fireplace, a dining area with a wooden table, and a large window with curtains.

16. Zen House at the Mountain Ridge

Zen House at the Mountain Ridge
Gardiner
10.0 out of 10, Exceptional, (13 reviews)
"The house was perfect and really well decorated. The area it was in, proximity to everything. Couldn't have asked for a better spot."
United States
Theresa
The price is AU$332
includes taxes & fees
19 Nov - 20 Nov
Zen House at the Mountain Ridge
A modern kitchen with a central island, built-in appliances, and a stone accent wall.

17. 3BR Hudson Valley home perfect for families!

3BR Hudson Valley home perfect for families!
Wallkill
10.0 out of 10, Exceptional, (6 reviews)
"This property was lovely and peaceful! We enjoyed the stay in the area! Very clean and neat. Easy to use technology and check-in/out."
United States
Cheryl N.
The price is AU$745
includes taxes & fees
22 Nov - 23 Nov
3BR Hudson Valley home perfect for families!
A hot tub on a wooden deck with a view of a river and trees.

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

Welcome to The Boathouse! Waterfront/Boats/Hot tub
New Paltz
9.6 out of 10, Exceptional, (14 reviews)
"Seth was great and the property was really nice. Never did see any fitness center, not sure where that was, but it was a really nice place and I would definetly stay there again."
United States
Thomas S.
The price is AU$612
includes taxes & fees
17 Nov - 18 Nov
Welcome to The Boathouse! Waterfront/Boats/Hot tub
A neatly made bed with white bedding and a few colorful pillows, a wooden headboard, and a wall-mounted light fixture.

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

Retro Retreat: renovated 2BR, desk, no chore list!
Kingston
9.6 out of 10, Exceptional, (15 reviews)
"Great, easy, full of everything you’d need. Stayed with 2 others for a work trip and it was perfect! "
United States
Kelley Marie
The price is AU$399
includes taxes & fees
17 Nov - 18 Nov
Retro Retreat: renovated 2BR, desk, no chore list!
A spacious living area with a high ceiling, wooden beams, two leather sofas, a central rug, and a staircase leading to an upper level.

20. The Loft At The Inn At High Falls

The Loft At The Inn At High Falls
High Falls
8.6 out of 10, Excellent, (25 reviews)
"this was just a lovely stay all around!! Will absolutely stay there again!"
United States
Inez
The price is AU$487
includes taxes & fees
13 Nov - 14 Nov
The Loft At The Inn At High Falls
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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Poughkeepsie and related destinations

Stroll along the elevated Walkway Over the Hudson for spectacular river views and a glimpse of the Catskill Mountains. Vassar College's art museum and the historic Bardavon Opera House offer cultural experiences worth planning your visit around.

See all hotels in Poughkeepsie
A large steel bridge spanning a wide river, with a cityscape and hills in the background.

Top reviews in Poughkeepsie

A multi-story hotel with a central entrance, stone pillars, and a brick facade.
Inn at Bellefield / Hyde Park, Residence Inn by Marriott

Inn at Bellefield / Hyde Park, Residence Inn by Marriott

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

10/10 Excellent

Very good well recommended
Australia
Stephen
Reviewed November 11, 2026
Inn at Bellefield / Hyde Park, Residence Inn by Marriott