Poughkeepsie Holiday Rentals

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Check prices for these dates

In two weeks
28 Nov - 30 Nov
In two months
9 Jan - 11 Jan
In three months
6 Feb - 8 Feb
In four months
6 Mar - 8 Mar

Holiday Rentals in Poughkeepsie

Outdoor dining
Mid-Century DJ’s Dream

Mid-Century DJ’s Dream

Staatsburg
10.0 out of 10, Exceptional, (43)
"Great place to stay! Close to many attractions by car - most 10-15 minutes. Clean and comfortable. Kevin has lots of great suggestions on places to go and restaurants."
United States
Anonymous traveller
The price is HK$863
HK$1,521 total
includes taxes & fees
18 Nov - 19 Nov
Mid-Century DJ’s Dream
Property grounds
Private Studio Close to Downtown Rhinebeck

Private Studio Close to Downtown Rhinebeck

RHINEBECK
10.0 out of 10, Exceptional, (25)
"This a an adorable, well designed, spotless space which was perfect for our over night stay in Rhinebeck. Property a quick walk away from the fairgrounds and downtown was also walkable…the host was absolutely amazing with great communication and detailed instructions! "
United States
Kathy
The price is HK$762
HK$1,969 total
includes taxes & fees
1 Dec - 2 Dec
Private Studio Close to Downtown Rhinebeck
Fridge, microwave, oven, stovetop
Lux APT Your home away from home.

Lux APT Your home away from home.

Beacon
10.0 out of 10, Exceptional, (2)
"Omar was great at communicating and it was pet friendly. "
United States
Henry C.
The price is HK$1,166
HK$2,180 total
includes taxes & fees
16 Nov - 17 Nov
Lux APT Your home away from home.
Fridge, microwave, oven, stovetop
Cozy Escape -Strong Wi-Fi -Prime Location

Cozy Escape -Strong Wi-Fi -Prime Location

Poughkeepsie
6.8 out of 10, (5)
"It is in a dangerous neighborhood with unsafe conditions there was a street person sleeping on back porch there were bed bugs wings under beds the bed frame was unsafe the stairs are not legal with a handrail at 24" that neither reaches the top nor the bottom of the staircase, the main bathroom is not in the apartment and you have to go on stairs to get to it everyone in our group was in their 70s and we were unable to access the apartment. We have been unable to even get a dime back even tho...
United States
Kimberly C.
The price is HK$692
HK$2,440 total
includes taxes & fees
8 Dec - 9 Dec
Cozy Escape -Strong Wi-Fi -Prime Location
King Bed Private Parking Fast Internet

King Bed Private Parking Fast Internet

Poughkeepsie
The price is HK$667
HK$2,319 total
includes taxes & fees
23 Nov - 24 Nov
King Bed Private Parking Fast Internet
Private kitchen
Welcome to New Paltz. Charming 3-bedroom house with AC, WIFI,

Welcome to New Paltz. Charming 3-bedroom house with AC, WIFI,

new paltz
9.6 out of 10, Exceptional, (4)
"Very clean Good communication with host Close to town & hiking Recommend! "
United States
Jennifer E.
The price is HK$1,554
HK$5,718 total
includes taxes & fees
15 Nov - 16 Nov
Welcome to New Paltz. Charming 3-bedroom house with AC, WIFI,
Interior
Stunning 5-bedroom house with AC / Heat in charming Poughkeepsie NY

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

Poughkeepsie
10.0 out of 10, Exceptional, (2)
"House worked perfectly for our needs. Newly renovated home. Parking was plentiful behind the home. "
United States
Wayne S.
The price is HK$1,287
HK$4,520 total
includes taxes & fees
16 Nov - 17 Nov
Stunning 5-bedroom house with AC / Heat in charming Poughkeepsie NY
Exterior
2Br Private Victorian Apartment in City Location on Half Acre Sleeps 5

2Br Private Victorian Apartment in City Location on Half Acre Sleeps 5

2.0 star property
Poughkeepsie
10.0 out of 10, Exceptional, (5)
"My friends and I rented this property for a long girls weekend to attend an event in the area. We liked the historical aspect of the property and Gary was an excellent host. His banana bread was amazing! We would definitely stay again. "
United States
Sara
The price is HK$1,805
HK$2,114 total
includes taxes & fees
15 Dec - 16 Dec
2Br Private Victorian Apartment in City Location on Half Acre Sleeps 5
TV, fireplace
1 Br Private Victorian Apt in convenient City location on half acre sleeps 4

1 Br Private Victorian Apt in convenient City location on half acre sleeps 4

Poughkeepsie
10.0 out of 10, Exceptional, (3)
"The host was gracious and the apartment had everything I could want to feel comfortable. The location was very convenient to the colleges and in a gorgeous neighborhood. I will definitely be coming back again. "
United States
Sarah D.
The price is HK$1,659
HK$1,792 total
includes taxes & fees
16 Nov - 17 Nov
1 Br Private Victorian Apt in convenient City location on half acre sleeps 4
Exterior
2Br Private Victorian Apartment in City location on half acre Sleeps 5

2Br Private Victorian Apartment in City location on half acre Sleeps 5

Poughkeepsie
8.8 out of 10, Excellent, (3)
"Very clean place with a lot of amenities. Safe area."
United States
JESSICA
The price is HK$1,991
HK$2,150 total
includes taxes & fees
16 Nov - 17 Nov
2Br Private Victorian Apartment in City location on half acre Sleeps 5
Terrace/patio
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, (1)
"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$1,554
HK$3,290 total
includes taxes & fees
15 Dec - 16 Dec
Step into history & unwind at Spring apt a charming 🏡 at the❤️of NYHudson Valley
Exterior
Rustic Cabin in Fishkill!

Rustic Cabin in Fishkill!

Fishkill
10.0 out of 10, Exceptional, (3)
"Ideal cabin getaway. "
United States
Nadja E.
The price is HK$2,351
HK$3,513 total
includes taxes & fees
17 Nov - 18 Nov
Rustic Cabin in Fishkill!
Fridge, microwave, oven, stovetop
Sunkissed Escape Bright Sunroom + Hammock Fun

Sunkissed Escape Bright Sunroom + Hammock Fun

2.0 star property
Poughkeepsie
The price is HK$1,826
HK$2,906 total
includes taxes & fees
25 Nov - 26 Nov
Sunkissed Escape Bright Sunroom + Hammock Fun
Property grounds
Hudson Escape W/ Hot Tub + Bridge View

Hudson Escape W/ Hot Tub + Bridge View

Highland
The price is HK$2,547
HK$5,167 total
includes taxes & fees
1 Dec - 2 Dec
Hudson Escape W/ Hot Tub + Bridge View
Fridge, microwave, oven, stovetop
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

2.0 star property
New Paltz
9.4 out of 10, Exceptional, (24)
"Communication for check-in,checking out was flawless "
United States
tim m.
The price is HK$2,564
HK$4,041 total
includes taxes & fees
16 Nov - 17 Nov
Scenic New Paltz Escape: River Views, Hot Tub & Deck | Dream House in the Gunks
Exterior
Red Cottage - Lakeside Property!

Red Cottage - Lakeside Property!

Fishkill
The price is HK$4,060
HK$5,664 total
includes taxes & fees
17 Nov - 18 Nov
Red Cottage - Lakeside Property!
Fridge, oven, stovetop, coffee/tea maker
Vineyard Retreat: 3BR Home-Live Music, Wine+Hiking

Vineyard Retreat: 3BR Home-Live Music, Wine+Hiking

New Paltz
6.0 out of 10, (5)
"10 minutes to town, great view off the deck, peaceful."
United States
irv h.
Vineyard Retreat: 3BR Home-Live Music, Wine+Hiking
Outdoor dining
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
9.6 out of 10, Exceptional, (45)
"Plenty of seating & comfortable beds were a plus! The theatre room was really fun for grandkids!"
United States
Lisa B.
The price is HK$2,013
HK$2,593 total
includes taxes & fees
30 Nov - 1 Dec
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
Terrace/patio
Spacious New Luxurious holiday house in lovely Hudson Valley

Spacious New Luxurious holiday house in lovely Hudson Valley

Poughkeepsie
9.8 out of 10, Exceptional, (22)
"Huge, spacious and beautiful house with large and comfortable rooms and each one with its own bathroom, essential for privacy in large groups, large kitchen to enjoy with family and friends, children and adults enjoyed the ping pong table and other amenities, also the grill, excellent location close to markets, restaurants and boutiques, what we could recommend is to make sure that the internet always works.We are pleased to stay here, Thank you !!!!"
United States
RAFAEL U.
The price is HK$2,972
HK$5,410 total
includes taxes & fees
16 Nov - 17 Nov
Spacious New Luxurious holiday house in lovely Hudson Valley
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

Overlook Lodge at Bear Mountain

Overlook Lodge at Bear Mountain

10/10 Excellent
"Originally, we were in the Lodge. We were told that it was a 10-15 minute walk from the Inn which is the main building not only for rooms but the restaurant and lounge area. What they failed to say was that the walk between the Inn and the Lodge is not only up-and-down hilly but takes around 15-20 minutes to walk. There is a car service of which we availed ourselves. We also switched into the Inn the next day when a beautiful room opened up. It had two rooms — a living room with a sofa and lounge chairs, a gigantic TV screen on the wall and a hutch with a refrigerator. The bedroom had two double beds and an entry to the bathroom. We were more than satisfied! This “little apartment” made our stay! Ruth Dunner"
Ruth 3-night trip
Posted 2 days ago
Overlook Lodge at Bear Mountain

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
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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 BBQ and air conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a stovetop and a microwave.

How many holiday rentals are there in Poughkeepsie?

Expedia has 24 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.