Holiday Rentals in Poughkeepsie

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Holiday Rentals in Poughkeepsie

1 Br Private Victorian Apt in Convenient City Location on Half Acre Sleeps 4

2.0 star property
9.0 out of 10, Wonderful, (8)
"Gary is a great host and provides a wonderful experience. He is the best and it was a very nice stay. Best host I have had before."
The price is €174
includes taxes & fees
2 Oct - 3 Oct
1 Br Private Victorian Apt in Convenient City Location on Half Acre Sleeps 4

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

9.8 out of 10, Exceptional, (122)
"It has an incredible mountain and water view. "
The price is €268
includes taxes & fees
13 Oct - 14 Oct
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.

10.0 out of 10, Exceptional, (90)
"My family and I loved this property! We enjoyed walking around the woods and exploring. The house was well equipped and was really charming. We also loved sightseeing around the near by towns. Definitely a place to come back to stay again. "
Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.

'A Place in the Woods' - Cabin on Chloe's Lake on 23 acres near Woodstock, NY

8.2 out of 10, Very good, (46)
"A quirky tiny cabin off the beaten path but in need of some upkeep, e.g. toilet not fully attached to the floor in the Tipi room, water has sulphur smell. We were only there for an overnight stay, and I sent a note once we were home, so hopefully the owners get a chance to fix things up! Pricey for its current condition."
The price is €142
includes taxes & fees
15 Oct - 16 Oct
'A Place in the Woods' - Cabin on Chloe's Lake on 23 acres near Woodstock, NY

Log Cabin On A Lake With Private Dock & Beach! One Hour from NYC! No Pet Fees!

10.0 out of 10, Exceptional, (194)
"Wonderful place to rest and recharge."
Log Cabin On A Lake With Private Dock & Beach! One Hour from NYC! No Pet Fees!

Fall Colors HQs. Stunning views of Croton River Gorge, a birder haven

9.6 out of 10, Exceptional, (10)
"Easy check in and check out! Has all the bare minimums and a nicely upgraded bathroom. Didn’t feel super clean (the bathroom) when we got there but kitchen was clean and they kindly stocked a few groceries. Could not get the water hot for a shower which was bummer. Nice enough depending on what you are looking for! We had some sensory needs and so this ended up not being the best fit but the location was great. Thanks for having us. "
Fall Colors HQs. Stunning views of Croton River Gorge, a birder haven

Esopus Creek modern Tiny house Retreat!

9.8 out of 10, Exceptional, (55)
"The property was beautiful. Quiet area but close enough to all the places we wanted to go. Our hosts were very gracious, attentive and friendly. Enjoyed our weekend retreat. "
The price is €209
includes taxes & fees
2 Oct - 3 Oct
Esopus Creek modern Tiny house Retreat!

Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream

9.2 out of 10, Wonderful, (44)
"This is a great place to stay. Really loved the fire pit by the creek for evening cocktails and conversation."
The price is €271
includes taxes & fees
5 Oct - 6 Oct
Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream

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

9.6 out of 10, Exceptional, (36)
"Great place for a quiet stay"
The price is €290
includes taxes & fees
1 Nov - 2 Nov
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo

Scenic New Paltz Escape: River Views, Hot Tub & Deck | Dream House in the Gunks

2.0 star property
9.8 out of 10, Exceptional, (17)
"The property was perfectly secluded while being close to town. We observed lots of wildlife including deer, a woodchuck family, and a turtle laying eggs! The house was roomy and comfortable with just enough upscale elegance that made us feel pampered."
The price is €483
includes taxes & fees
2 Oct - 3 Oct
Scenic New Paltz Escape: River Views, Hot Tub & Deck | Dream House in the Gunks

Hamptons on the Hudson in South Saugerties

10.0 out of 10, Exceptional, (30)
"Lovely property, well-maintained, clean and comfortable, and the host was especially responsive to all communications. Highly recommend."
Hamptons on the Hudson in South Saugerties

Minutes to Saugerties & HITS Horse show. Above garage w/ own private entrance.

2.0 star property
The price is €198
includes taxes & fees
2 Oct - 3 Oct
Minutes to Saugerties & HITS Horse show. Above garage w/ own private entrance.

Chestnut on Willow Lake

9.4 out of 10, Exceptional, (3)
"We really enjoyed the privacy of the grounds, lake, dock , swimming, boats and paddle boards. The kitchen was well equipped and the beds were comfy. We had a great stay, thanks."
The price is €511
includes taxes & fees
30 Oct - 31 Oct
Chestnut on Willow Lake

Tiny Cat Tiny House

10.0 out of 10, Exceptional, (4)
"An ideal place to forget about the city, perfect for a long weekend"
The price is €205
includes taxes & fees
2 Oct - 3 Oct
Tiny Cat Tiny House

Lakehouse Boat Dock, Kayaks, Fire-Pit, Pool Table, Air Hockey, Hammock, King Bed

9.4 out of 10, Exceptional, (30)
"Stayed here to visit family and it was perfect for what we needed. Would recommend staying here. "
Lakehouse Boat Dock, Kayaks, Fire-Pit, Pool Table, Air Hockey, Hammock, King Bed

Sioux Tipi on Chloe's Lake

9.8 out of 10, Exceptional, (6)
"This was such a cool experience Id love to go back! "
The price is €128
includes taxes & fees
12 Oct - 13 Oct
Sioux Tipi on Chloe's Lake

Catskill Retreat: Cozy Cabin with Cedar Hot Tub & Pet-Friendly

9.2 out of 10, Wonderful, (31)
"Loved this place host was very helpful and placed was well taken care of"
Catskill Retreat: Cozy Cabin with Cedar Hot Tub & Pet-Friendly

Cozy Lakefront Home - 278 FIVE STAR Reviews - Kayaks, Sunsets & Panoramic Views

10.0 out of 10, Exceptional, (308)
"We had the most relaxing 3 night stay at Don's vacation home. It is spacious and comfortable. Orange Lake right out the back door was a beautiful backdrop all throughout the day. Don gave us great recommendations for local restaurants too.It was the perfect weekend."
Cozy Lakefront Home - 278 FIVE STAR Reviews - Kayaks, Sunsets & Panoramic Views

Cozy Catskill Cabin w/ 10-minute Walk to Downtown Catskill

9.8 out of 10, Exceptional, (30)
"Great location "
The price is €299
includes taxes & fees
28 Oct - 29 Oct
Cozy Catskill Cabin w/ 10-minute Walk to Downtown Catskill

A Spectacular 50 Mile View of the Hudson Valley in all seasons

9.8 out of 10, Exceptional, (92)
"Had an absolutely fantastic time. Beautiful property and the owners are incredibly kind and welcoming "
A Spectacular 50 Mile View of the Hudson Valley in all seasons
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

Find out more about Poughkeepsie

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 €128 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?

Tiny Cat Tiny House: This holiday home rental outside of Poughkeepsie comes with air conditioning so that you can feel at home during your trip.

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.