Search Holiday Rentals in Poughkeepsie

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Save instantly and earn perks with One Key
    Learn about One Key

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
20 Nov - 22 Nov
In two months
1 Jan - 3 Jan
In three months
29 Jan - 31 Jan
In four months
26 Feb - 28 Feb

Our top choices for Poughkeepsie holiday rentals

A hotel lobby with a reception desk, seating area, and a fire extinguisher on the wall.

1. 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
The price is £60
includes taxes & fees
22 Nov - 23 Nov
1 King Bed | Non-Smoking, Kitchen, Shower
A brick building with a sign reading 'Lobby' in front.

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

Cozy Queen Suite, Nsmk Kitchen|Studio 6 Fishkill
Fishkill
9.0 out of 10, Wonderful, (21 reviews)
"Great place to stay,"
United States
Anonymous traveller
The price is £68
includes taxes & fees
25 Nov - 26 Nov
Cozy Queen Suite, Nsmk Kitchen|Studio 6 Fishkill
A modern kitchen with a granite countertop, a built-in stove, and a dining area with a glass table and chairs.

3. 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 £360
includes taxes & fees
9 Nov - 10 Nov
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.

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

Pleasant 1-bedroom apartment in Staatsburg perfect for your getaway,
Staatsburg
9.6 out of 10, Exceptional, (13 reviews)
"We thoroughly enjoyed our stay. We would definitely come back! A fantastic location. And very good communication with the host, Alexander."
United States
elizabeth
The price is £153
includes taxes & fees
10 Nov - 11 Nov
Pleasant 1-bedroom apartment in Staatsburg perfect for your getaway,
A room with a large bookshelf filled with books and DVDs, a bed, a small table with a lamp, and a window with blinds.

5. Mid-Century DJ’s Dream

Mid-Century DJ’s Dream
Staatsburg
10.0 out of 10, Exceptional, (61 reviews)
"Quiet clean accommodations in a central location for exploring the Hudson Valley."
United States
Alexandra R.
The price is £175
includes taxes & fees
11 Nov - 12 Nov
Mid-Century DJ’s Dream
A neatly made bed with a white pillow, a red pillow, and a white blanket. There is a small bedside table with a lamp.

6. 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 £191
includes taxes & fees
10 Nov - 11 Nov
Hibiscus Suite - Private Studio Apartment in Rhinebeck Village
A porch with white railings and multiple chairs.

7. 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 £322
includes taxes & fees
8 Nov - 9 Nov
Step into history & unwind at Spring apt a charming 🏡 at the❤️of NYHudson Valley
A spacious living area with a staircase, a dining table, and a sofa.

8. 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 £491
includes taxes & fees
8 Nov - 9 Nov
Our home is perfect for relaxing and having lots of fun, with near by activity’s
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 £324
includes taxes & fees
8 Nov - 9 Nov
Step into history & unwind at Elixir apt a charming 🏡 at the❤️of NYHudson Valley
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.

10. 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 £429
includes taxes & fees
9 Nov - 10 Nov
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.

11. 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 £255
includes taxes & fees
8 Nov - 9 Nov
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.

12. 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 £236
includes taxes & fees
15 Nov - 16 Nov
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
A covered outdoor area with a barbecue grill and a hot tub.

13. 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 £300
includes taxes & fees
15 Nov - 16 Nov
Scenic New Paltz Escape: River Views, Hot Tub & Deck | Dream House in the Gunks
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 £329
includes taxes & fees
10 Nov - 11 Nov
perfect studio, few minutes away to the heart of new Paltz & Mohonk Mountain
An aerial view of a lakeside property with a dock, a small building, and several outdoor seating areas.

15. Rustic Cabin in Fishkill!

Rustic Cabin in Fishkill!
Fishkill
9.8 out of 10, Exceptional, (6 reviews)
"Clean rooms, Diner down the block, family friendly, communication was prompt and clear"
United States
Joseph
The price is £279
includes taxes & fees
13 Nov - 14 Nov
Rustic Cabin in Fishkill!
A lakeside seating area with Adirondack chairs arranged around a central fire pit.

16. Red Cottage - Lakeside Property!

Red Cottage - Lakeside Property!
Fishkill
The price is £302
includes taxes & fees
11 Nov - 12 Nov
Red Cottage - Lakeside Property!
A stone house with a steeply pitched roof, surrounded by a well-maintained lawn and trees.

17. 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 £395
includes taxes & fees
11 Nov - 12 Nov
Chestnut on Willow Lake
A brick building with a sign reading 'Lobby' in front.

18. 2 Full Beds | Non-Smoking, Kitchen

2 Full Beds | Non-Smoking, Kitchen
Fishkill
9.0 out of 10, Wonderful, (22 reviews)
"great place tostay"
United States
Anonymous traveller
The price is £75
includes taxes & fees
24 Nov - 25 Nov
2 Full Beds | Non-Smoking, Kitchen
A hotel room with a sofa, armchairs, a coffee table, a chandelier, framed pictures on the wall, and a large window with blinds.

19. 1 Queen Bed | Non-Smoking, Kitchen

1 Queen Bed | Non-Smoking, Kitchen
Fishkill
7.6 out of 10, Good, (27 reviews)
"The property was clean and pet friendly. However, the small extended stay room with a kitchen had no glasses or bowls or flat ware. You can't expect any additional accomodations beyond the room."
United States
Ray
The price is £68
includes taxes & fees
25 Nov - 26 Nov
1 Queen Bed | Non-Smoking, Kitchen
A hotel room with a sofa, armchairs, a coffee table, a chandelier, framed pictures on the wall, and a large window with blinds.

20. Studio 6 Fishkill|King bed|Hearing Access|Kitchen

Studio 6 Fishkill|King bed|Hearing Access|Kitchen
Fishkill
10.0 out of 10, Exceptional, (18 reviews)
"great place to stay"
United States
Anonymous traveller
The price is £70
includes taxes & fees
3 Dec - 4 Dec
Studio 6 Fishkill|King bed|Hearing Access|Kitchen
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.
View all properties

Find holiday rentals that suit your style

cabin image
Cabins
Cabins
Apartment image
Apartments
Apartments

Top Poughkeepsie Hotel Reviews

A modern lobby with a blue sofa, marble coffee table, and a reception desk with a blackboard.
The Heartwood

The Heartwood

The Heartwood
Arlington

10/10 Excellent

Lovely hotel in a great location. Staff were excellent and very friendly. We really enjoyed the happy hour in the bar and the live music outside which was excellent!! Highly recommended!
United Kingdom
Graham
Reviewed September 11, 2026
The Heartwood

Find out more about Poughkeepsie

Everything you need to know about Poughkeepsie holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Poughkeepsie holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Poughkeepsie holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Poughkeepsie holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Poughkeepsie. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Poughkeepsie holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Poughkeepsie holiday rentals we have selected for you start as low as £59 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Poughkeepsie rentals

At Expedia, we put the best Poughkeepsie holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Poughkeepsie rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Poughkeepsie holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Poughkeepsie. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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.