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Poughkeepsie Holiday Rentals

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Check prices for these dates

In two weeks
23 Oct - 25 Oct
In two months
4 Dec - 6 Dec
In three months
1 Jan - 3 Jan
In four months
29 Jan - 31 Jan

Our top choices for Poughkeepsie holiday rentals

A modern living room with a sectional sofa, a coffee table, and a bar area with stools.

1. Private, Cozy, Clean apartment in lovely Hyde Park

Private, Cozy, Clean apartment in lovely Hyde Park
Hyde Park
10.0 out of 10, Exceptional, (2 reviews)
"The host was great, the place was really nice and cozy. I would definitely stay here again!!! "
United States
Janet M.
The price is HK$989
HK$1,527 total
includes taxes & fees
12 Oct - 13 Oct
Private, Cozy, Clean apartment in lovely Hyde Park
A modern kitchen with a granite countertop, a built-in stove, and a dining area with a glass table and chairs.

2. 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)
"Beautiful property with ample space for parking. Host was super nice and met all of our needs!"
United States
Nicole Y.
The price is HK$1,261
HK$3,379 total
includes taxes & fees
7 Oct - 8 Oct
Stunning 5-bedroom house with AC / Heat in charming Poughkeepsie NY
A modern kitchen with white cabinets, a central island, and a view to the outside.

3. Pleasant 1-bedroom apartment in Staatsburg perfect for your getaway,

Pleasant 1-bedroom apartment in Staatsburg perfect for your getaway,
Staatsburg
9.4 out of 10, Exceptional, (10 reviews)
"Nice stay for our quick overnight Comfortable space "
United States
jay c.
The price is HK$883
HK$1,638 total
includes taxes & fees
19 Oct - 20 Oct
Pleasant 1-bedroom apartment in Staatsburg perfect for your getaway,
A hotel lobby with a reception desk, seating area, and a fire extinguisher on the wall.

4. 1 King Bed | Non-Smoking, Kitchen, Shower

1 King Bed | Non-Smoking, Kitchen, Shower
Fishkill
9.6 out of 10, Exceptional, (19 reviews)
"Great rooms and service,"
United States
Anonymous traveller
1 King Bed | Non-Smoking, Kitchen, Shower
A brick building with a sign reading 'Lobby' in front.

5. 2 Full Beds | Non-Smoking, Kitchen

2 Full Beds | Non-Smoking, Kitchen
Fishkill
9.2 out of 10, Wonderful, (21 reviews)
"great place tostay"
United States
Anonymous traveller
The price is HK$685
HK$792 total
includes taxes & fees
3 Nov - 4 Nov
2 Full Beds | Non-Smoking, Kitchen
A deck with a red umbrella, wooden chairs, and a table with potted plants.

6. Mid-Century DJ’s Dream

Mid-Century DJ’s Dream
Staatsburg
10.0 out of 10, Exceptional, (60 reviews)
"Quiet clean accommodations in a central location for exploring the Hudson Valley."
United States
Alexandra R.
The price is HK$1,562
HK$2,424 total
includes taxes & fees
5 Nov - 6 Nov
Mid-Century DJ’s Dream
A close-up of a red bench with a metal frame, set against a blurred background.

7. Hibiscus Suite - Private Studio Apartment in Rhinebeck Village

Hibiscus Suite - Private Studio Apartment in Rhinebeck Village
Rhinebeck Village
10.0 out of 10, Exceptional, (33 reviews)
"Beautiful place has a great stay!"
United States
Heather O.
The price is HK$897
HK$2,160 total
includes taxes & fees
6 Oct - 7 Oct
Hibiscus Suite - Private Studio Apartment in Rhinebeck Village
A porch with white railings and multiple chairs.

8. Step into history & unwind at Spring apt a charming 🏡 at the❤️of NYHudson Valley

Step into history & unwind at Spring apt a charming 🏡 at the❤️of NYHudson Valley
Highland
10.0 out of 10, Exceptional, (2 reviews)
"Everyone was just right! The home is perfect for a photo shoot. We weren't there for that, but we thought the setting was unique and beautiful! Everything we needed!!"
United States
Rebecca D.
The price is HK$1,334
HK$3,076 total
includes taxes & fees
6 Oct - 7 Oct
Step into history & unwind at Spring apt a charming 🏡 at the❤️of NYHudson Valley
A wooden porch with white rocking chairs and a hanging flower basket.

9. Step into history & unwind at Elixir apt a charming 🏡 at the❤️of NYHudson Valley

Step into history & unwind at Elixir apt a charming 🏡 at the❤️of NYHudson Valley
Highland
9.6 out of 10, Exceptional, (11 reviews)
"Would definitely stay again"
United States
Laurie G.
The price is HK$1,570
HK$3,366 total
includes taxes & fees
12 Oct - 13 Oct
Step into history & unwind at Elixir apt a charming 🏡 at the❤️of NYHudson Valley
A spacious living area with a staircase, a dining table, and a sofa.

10. 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)
"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 HK$1,907
HK$5,695 total
includes taxes & fees
6 Oct - 7 Oct
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.

11. 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.
Chilly Days Hiking, Quiet Yard, an Easy Escape Near New Paltz
A wooden deck with outdoor furniture, surrounded by lush greenery and a small garden.

12. SUPERB VILLAGE LOCATION!! SWEET APARTMENT w/PRIVATE DECK in historic district

SUPERB VILLAGE LOCATION!! SWEET APARTMENT w/PRIVATE DECK in historic district
New Paltz
9.8 out of 10, Exceptional, (6 reviews)
"The stay was great! Cozy, quirky and quaint. Gabriela was super nice and accommodating."
United States
Jehiah B.
The price is HK$1,907
HK$2,760 total
includes taxes & fees
6 Oct - 7 Oct
SUPERB VILLAGE LOCATION!! SWEET APARTMENT w/PRIVATE DECK in historic district
An outdoor patio area with a covered seating area, a pool, and potted plants.

13. 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)
"It’s was nice, clean and the outdoor out area was really nice."
United States
Roger S.
The price is HK$2,050
HK$2,679 total
includes taxes & fees
8 Oct - 9 Oct
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
A house with a covered patio, a large window, and a small porch area.

14. perfect studio, few minutes away to the heart of new Paltz & Mohonk Mountain

perfect studio, few minutes away to the heart of new Paltz & Mohonk Mountain
New Paltz
2.0 out of 10, (1 review)
"When we arrived at the house, we unpacked and within a few minutes, we smelled something that smelled like sewer gas in the bathroom. The owners came over and accused us of pouring something down the drain to get out of paying them. We could not stay in the house it smelled so bad and they would not refund our money. VRBO took their side! This was a horrific experience. I hope they get the sewer smell figured out. I just wanted to visit my daughter and this turned into a nightmare. I understand...
United States
Susannah R.
The price is HK$1,236
HK$3,538 total
includes taxes & fees
7 Oct - 8 Oct
perfect studio, few minutes away to the heart of new Paltz & Mohonk Mountain
A covered outdoor area with a barbecue grill and a hot tub.

15. 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)
"Exactly as listed, great property and host."
United Kingdom
Neil C.
Scenic New Paltz Escape: River Views, Hot Tub & Deck | Dream House in the Gunks
An aerial view of a lakeside property with a dock, a small building, and several outdoor seating areas.

16. Rustic Cabin in Fishkill!

Rustic Cabin in Fishkill!
Fishkill
10.0 out of 10, Exceptional, (5 reviews)
"Ideal cabin getaway. "
United States
Nadja E.
The price is HK$2,158
HK$3,282 total
includes taxes & fees
1 Nov - 2 Nov
Rustic Cabin in Fishkill!
A brick building with a sign reading 'Lobby' in front.

17. Cozy Queen Suite, Nsmk Kitchen|Studio 6 Fishkill

Cozy Queen Suite, Nsmk Kitchen|Studio 6 Fishkill
Fishkill
9.2 out of 10, Wonderful, (20 reviews)
"Great place to stay,"
United States
Anonymous traveller
The price is HK$623
HK$720 total
includes taxes & fees
3 Nov - 4 Nov
Cozy Queen Suite, Nsmk Kitchen|Studio 6 Fishkill
A brick building with a sign reading 'Lobby' in front.

18. 1 Queen Bed | Non-Smoking, Kitchen

1 Queen Bed | Non-Smoking, Kitchen
Fishkill
8.4 out of 10, Very good, (23 reviews)
"Nice place to stay"
United States
Anonymous traveller
The price is HK$623
HK$720 total
includes taxes & fees
3 Nov - 4 Nov
1 Queen Bed | Non-Smoking, Kitchen
Bedroom

19. 2 Queen Beds | Non-Smoking, Kitchen

2 Queen Beds | Non-Smoking, Kitchen
Fishkill
8.4 out of 10, Very good, (25 reviews)
"Arrived with paid reservation -no rooms available......not a legit business. The sister hotel in the area had same issue earlier this year. I will not return."
United States
Cheryl
2 Queen Beds | Non-Smoking, Kitchen
A stone house with a steeply pitched roof, surrounded by a well-maintained lawn and trees.

20. 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 HK$3,021
HK$4,297 total
includes taxes & fees
1 Nov - 2 Nov
Hickory on Willow Lake
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 Poughkeepsie Hotel Reviews

The Heartwood

The Heartwood

10/10 Excellent
"Great location, walking distance to Vassar College, very unique hotel"
Babak 1-night trip
Posted 1 hour ago
The Heartwood

Find out more about Poughkeepsie

Search for holiday rentals in Poughkeepsie on Expedia! You can easily find your home rentals, villas, holiday apartments in Poughkeepsie using one of the methods below:

  • View our selection of featured holiday rentals in Poughkeepsie
  • Use the map to find apartments and other holiday homes in the Poughkeepsie neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Poughkeepsie while they last

Look no further and take a look at our great range of rental properties in Poughkeepsie!

Frequently asked questions

Are there holiday rentals in Poughkeepsie?

Yes, there are holiday rentals in Poughkeepsie close to Mid-Hudson Civic Center, or you can select a more secluded option if you're looking for a relaxing stay. Visitors like the university campus and scenic riverfront in Poughkeepsie. While you're in the area, you can also enjoy the top-notch restaurants and entertainment venues.

What are some of the best holiday rentals that Poughkeepsie has to offer?

Stunning 5-bedroom house with AC / Heat in charming Poughkeepsie NY: This highly rated holiday home rental in Poughkeepsie offers a fireplace, a patio and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a stovetop and a microwave, so that you can cook with friends or family. Make the most of garden in this rental home to help you unwind.

How many holiday rentals are there in Poughkeepsie?

Expedia has 16 holiday rentals for your stay in Poughkeepsie.

What can I see and do in Poughkeepsie?

Mid-Hudson Civic Center and McCann Ice Arena are a couple of the family-friendly sights, whereas cultural attractions include Bardavon 1869 Opera House and Locust Grove. Other places in town to visit include Mid-Hudson Bridge and Poughkeepsie Bridge.

What are holiday rentals like in Poughkeepsie?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Poughkeepsie. Holiday rentals offer extras such as kitchens and laundry facilities so you'll be comfy for your stay. If you're concerned about cleanliness, a holiday rental can provide a sense of safety away from public hotel lifts and busy reception areas while still allowing you a great travel experience. You'll also have more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a popular choice for a family getaway.