
House holiday rentals in Poughkeepsie
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Top-rated house rentals in Poughkeepsie
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Popular amenities for house rentals in Poughkeepsie
House rentals with a pool

Private Hudson Valley Country Retreat
This beautiful property has a special place in our hearts. We stayed in the A frame during COVID and we always wanted to come back. This time we stayed in the main house and it was phenomenal. Wish the weather was better for us to use the pool, but next time! It well worth the price. Only an hr from the city and it feels like a full vacation. Wonderful way to lose time time for a few days. We will be back!

Scenic River View Escape | New Paltz
I spent my birthday at this beautiful house and couldn’t have asked for a better experience. The place was spotless and full of natural light, with lovely views that made the stay even more special. The atmosphere was peaceful and clean, and the house had everything we needed for cooking and relaxing. I truly felt at home and appreciated all the thoughtful touches. Highly recommend for anyone looking for a cozy, well-equipped getaway!

Little owl Japanese teahouse: pool is OPEN
The teahouse and surroundings were relaxing and peaceful. We saw groundhogs, deer, and chipmunks from the porch and our 2 dogs loved exploring the field and wandering in the nearby woods. The pool was amazing and warm despite the rain and the natural landscaping couldn’t have been more beautiful. We really enjoyed our stay!

Midcentury Modern ZenHouse Sculptor Studio
Truly one of a kind property. Relaxing, calm, extremely responsive and helpful host. If you are looking to get out of the city or just need some time away to think, look no further. 10/10.

Harrison Field Pool Bike2Town FirePit 10AcreViews
We had a great stay at Nathan’s place. The playroom was great for our kids and we all enjoyed the pool. The view was also beautiful. We will definitely be back!

Upstate Modern Scandinavian Barn in the Catskills
We truly enjoyed our stay at Wilderkill Barn. Maria Cristina and William were exceptional hosts—warm, attentive, and genuinely committed to making our visit special. They went above and beyond to make us feel welcome. The home was a haven, with a hot tub, sauna, pool, fire pit, pool table, and immersive sound and movie systems—all of which made our stay delightful despite the cold, dreary May weather. We can't thank them enough. ***That said, we feel it's necessary to address a serious issue with Airbnb itself that arose while booking this property, unrelated to the property itself. An unexpected tax was added after booking, and Airbnb has yet to provide a clear explanation. After years of loyalty, we were disappointed by their evasive and unhelpful customer support. This experience has made us reconsider using the platform in the future. We urge potential users to scrutinize all fees carefully and be aware that Airbnb’s support may be difficult to navigate if problems arise.***

Cozy & Spacious Country Home - All Seasons
This house absolutely reminded me of home and my childhood ! So lovely and clean. Absolutely love the heated pool ! This was the perfect house for our wedding at the Mohonk mountain house . Close and such a comfortable stay . We really enjoyed the outdoor porch sitting room . Thank you for a comfortable and wonderful stay .

Beacon Beauty 4/2, Hot Tub,Pool,Wifi,1.5m to Town
We had a great stay at Tiffany’s place! Everything was exactly as described and she was great at communicating throughout the stay.
Weekly house rentals

Ideal for students and those who travel for work.
Overall a perfect place to crash for a night or two when in the area. It was quiet and clean. Our only issue was the bed- it’s very soft so of that’s not for you, you may not get a good night’s rest. But mainly the sides are somewhat sloped so I would start to fall toward the floor unless I pushed myself way back into the center. This may not be an issue for a single person, but for two it was. Otherwise a great spot!

Honeybug Snug near Omega Institute!
we stayed at Garrett's while attending a retreat at Omega. it's a beautiful little home on a gorgeous property. very comfortable and clean, it is a very charming space.

Spectacular Lake Views from Every Room & Garden
Lovely place with lake views. 100% happy with this choice vs other offerings in the area. House is set on a hill so you are viewing the lake from a higher spot than if you were literally on the lake. Very majestic. There are binoculars on the window sill to check out boats/things going on. I enjoyed the decor/sense of style the host has. Lots of interesting books, art, turntable, board games, cards, etc. The gardens, koi pond are well maintained. Rooms and bath upstairs do have lower ceiling but this info is disclosed in the ad. It didn’t detract from the experience. Went hiking but we were not avid hikers so learning to read the trail markers was new for us. The town is very small but we found nice spots to eat/visit nearby. We did use kitchen and coffee maker. Appliances are very new. Plenty of kitchen utensils. Cool hairdryer. Host def. appreciates design. Thank you for letting us stay a few extra hours past check out. Wonderful time! Felt like I really got away from the stress.

Hudson Valley Boutique Airb&b
It was a great stay and beautiful home. Really appreciated the ease of entry and amazing scenery.

The Wildflower House
Loved every part of our stay with Kristine. Perfect for a romantic weekend away - gorgeous cabin, well appointed, and great kitchen for cooking-in. Her recommendations for local spots were also so thoughtful. Thank you again!

The Gatehouse in Historic Hyde Park
This was a wonderful find and stay. We are very thankful to have found it. The attention to detail in this home is beyond appreciated. From the light switches to the furnishings and beyond it was perfect for us. Thank you so much. We will definitely return when in area.

3BR/3BA Renovated Retreat w/ Firepit By Rhinebeck
This is a lovely house, which is much larger on the inside than it appears from the outside. It would be perfect for a family or a girls weekend or a few couples. Marisa was very responsive when we had any questions.

Architect's Hudson Valley Home in the Woods
Olga's beautiful modern house in Upstate New York is a real gem nestled near a wild forest. The spacious house offers plenty of room to relax and unwind after a day exploring the area. The location offers a perfect blend of tranquility and adventure, with plenty of things to do in the surrounding area. Olga was a fantastic host – incredibly responsive and flexible, which made our stay even more enjoyable. The house itself is stunning, with modern amenities and stylish decor. We had a wonderful stay and highly recommend this Airbnb!
Private house rentals

Vassar Cottage - Charming 4 br home
This was a good place for our group to stay- 4 bedrooms, a decent kitchen, and a walkable neighborhood within range of Vassar College.

Beautiful, Spacious, 5 Acre Family Retreat
Lovely place. There were 7 ladies celebrating their 40th college reunion. Spacious and clean and beds were comfortable (we did double up on two beds.) Great place for relaxing and catching up.

3000 sq ft Poughkeepsie home with chef's kitchen
Bruce was a superlative host. Communicative and flexible, and we were greeted with a thoughtful (and abundant) welcome basket. The house clearly has been updated recently and is maintained immaculately yet comfortably. It did feel like there were a lot of rules -- but having spoken with Bruce, they were eminently understandable; I only mention it because if you're someone who's not good with following directions and/or honoring rules, it might not be the most favorable conditions for a good guest-host outcome, but IMHO that would be the guest's loss. We felt it was good value. Really nice front porch conducive to lounging. Details attended to well also, such as large, absorbent bath towels. Wish all hosts had their acts together like Bruce and a comportment like him.

Poughkeepsie 3br home near Vassar college/hospital
Great home very close to Vassar. Walkable, safe , clean. Easy to check in. Very responsive host. Will plan to stay here again!

Creekside Couple's Retreat w/Hot tub, Sauna & More
My husband and I were blown away by the beauty and thought that was put into this private destination. The moment you step on property, the freshness of the air and sounds of the creek are immediately calming. Diana was incredibly nice and very communicative before and during the entire stay. Activities: The sauna, creek, hot tub, pizza oven, grill, fire place/pits, hammocks- the amenities are amazing and unlike any other Airbnb I have ever been in before. So much that besides a quick dinner out one night (12 min away) and a nice walk around the Mountain Top Arboretum with our dog, we wanted to spend our time at the property. We called it our personal sanctuary spa!! The home: The home style is minimalistic but homey and every single item is top notch quality. There are no shortcuts- the entire place is a work of art. The bedroom and bathroom inspired me to reanalyze my own bedroom style. Thank you for upping the Airbnb game!! Can’t wait to come back to this magical spot! ✨

Hudson Riverfront Mid-Century Modern Home
A beautiful, comfortable house right on the Hudson with stunning views. We loved watching all the life on the river, herons and loons and ducks, as well as boats from tiny crafts to massive barges. There are great hikes just a short distance away. It is a perfect place to rest, write, draw, and make music.

The Cherry House
Lau-Rene was a great host and very friendly! She answered all my questions before arriving and helped out with a couple of things once we got there! The house was in a great location for Vassar related activities, beautiful neighborhood. I would stay there again!

NEW: Luxe Historical Style in Stone Ridge.
Beautifully designed home with really high end furniture. Aesthetically pleasing. It is right next to a main road, so there is a lot of noise from the cars. But once we got used to it, it was ok. Loved the house though.
Quick stats about house rentals in Poughkeepsie
Total rentals
40 properties
Nightly prices starting at
$51 SGD before taxes and fees
Total number of reviews
3.1K reviews
Family-friendly rentals
20 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
20 properties have a dedicated workspace
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- Hunter Mountain
- Mountain Creek Resort
- Bethel Woods Center for the Arts
- Belleayre Mountain Ski Center
- Minnewaska State Park Preserve
- Thunder Ridge Ski Area
- The Kartrite Resort & Indoor Waterpark
- Ringwood State Park
- Taconic State Park
- Resorts World Catskills
- Catamount Mountain Ski Resort
- Zoom Flume
- Windham Mountain
- Kent Falls State Park
- Rockland Lake State Park
- Walkway Over the Hudson State Historic Park
- Bash Bish Falls State Park
- Hudson Highlands State Park
- Brotherhood, America's Oldest Winery
- Wawayanda State Park
- Sterling Forest State Park
- Tallman Mountain State Park
- The Stanwich Club
- The Connecticut Golf Club