Holiday Homes in Poughkeepsie

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Featured Holiday Homes in Poughkeepsie

Luxury Upstate NY Home on 5 Acres w/ Hot Tub. Great for Families & Groups
Fridge, microwave, oven, stovetop
Luxury Upstate NY Home on 5 Acres w/ Hot Tub. Great for Families & Groups
10.0 out of 10, Exceptional, (87)
"Very nice property. Very nice owner. No problems noted."
Luxury Upstate NY Home on 5 Acres w/ Hot Tub. Great for Families & Groups
Lakehouse, Private Beach, Kayaks, FirePit, Gym, Movie Room, Pool Table, Air Hock
On the beach, sun-loungers
Lakehouse, Private Beach, Kayaks, FirePit, Gym, Movie Room, Pool Table, Air Hock
9.6 out of 10, Exceptional, (64)
"The good: We had a great time staying here. The first and second floor are beautiful and very well maintained. Both bathrooms and three bedrooms are very clean and have more than enough bath and beach towels. The fire pit and kayaks are also a great touch. The water is just steps away and the view is excellent. Just be sure to bring your own propane and firewood. What could be better? Communication with the host left a lot to be desired. I’m still not sure who runs the property. There are two...
Lakehouse, Private Beach, Kayaks, FirePit, Gym, Movie Room, Pool Table, Air Hock
1 HR NYC Getaway Awesome Newly Renovated Home on 4 Acres, Stunning Views
Smart TV
1 HR NYC Getaway Awesome Newly Renovated Home on 4 Acres, Stunning Views
9.0 out of 10, Wonderful, (24)
"It was a great couple of days"
1 HR NYC Getaway Awesome Newly Renovated Home on 4 Acres, Stunning Views
Hudson River Way by Woodstock Way Hotel
Panoramic House | Private kitchen
Hudson River Way by Woodstock Way Hotel
5.0 star property
Hudson River Way by Woodstock Way Hotel
Sweet and spacious mountain view home w/fireplace!
Interior
Sweet and spacious mountain view home w/fireplace!
9.8 out of 10, Exceptional, (16)
"What a great property, the house itself has such a comfy feel, the amount of natural light and views from main room are wonderful. At the s"
The price is NZ$641
includes taxes & fees
14 Oct - 15 Oct
Sweet and spacious mountain view home w/fireplace!
Red Barn Retreat - Shawangunk Mountains Getaway
Property grounds
Red Barn Retreat - Shawangunk Mountains Getaway
10.0 out of 10, Exceptional, (28)
"Everything was amazing. Restaurant recommendations were all great. "
Red Barn Retreat - Shawangunk Mountains Getaway
The Calf Pen
Property grounds
The Calf Pen
10.0 out of 10, Exceptional, (22)
"We had a great stay! "
The Calf Pen
Lovely 2 queen size bedroom apt one block from Rough Draft and Uptown Kingston
Exterior
Lovely 2 queen size bedroom apt one block from Rough Draft and Uptown Kingston
10.0 out of 10, Exceptional, (34)
"My partner and I so enjoyed our 3 night stay in such a spacious and clean place. They even Provided eggs milk butter champagne and welcome cookies. That was a first!! Walking distance to lots of fine restaurants and sights and a private garden backyard as well. We will definitely return again Alex and Brian. Ithaca "
Lovely 2 queen size bedroom apt one block from Rough Draft and Uptown Kingston
Historic Newburgh Home w/ Hudson River Views!
Fridge, microwave, stovetop, dishwasher
Historic Newburgh Home w/ Hudson River Views!
2.0 out of 10, (1)
Historic Newburgh Home w/ Hudson River Views!
Beautiful Escape! 'Parole LakeHouse' located 90min from NYC & 30min from Beacon
3 bedrooms, iron/ironing board, WiFi, bed sheets
Beautiful Escape! 'Parole LakeHouse' located 90min from NYC & 30min from Beacon
10.0 out of 10, Exceptional, (6)
"Absolutely loved our stay! The house was cozy, comfortable, and well-equipped. The host was responsive and made sure everything was just right. Highly recommend!!"
The price is NZ$1,468
includes taxes & fees
24 Sept - 25 Sept
Beautiful Escape! 'Parole LakeHouse' located 90min from NYC & 30min from Beacon
Lakeview Estate - Chef's Kitchen - NYC Getaway
Outdoor dining
Lakeview Estate - Chef's Kitchen - NYC Getaway
10.0 out of 10, Exceptional, (21)
"Great stay for 50th birthday "
The price is NZ$1,631
includes taxes & fees
25 Sept - 26 Sept
Lakeview Estate - Chef's Kitchen - NYC Getaway
Luxury Waterfront Retreat near New Paltz & the Gunks: Hike, Bike, or Relax!
Outdoor dining
Luxury Waterfront Retreat near New Paltz & the Gunks: Hike, Bike, or Relax!
9.8 out of 10, Exceptional, (40)
"Kelly was on top of it all…from initial check in to check out! Really appreciated the prompt communication and being so accommodating! This rental was clean, great location for hiking, biking and all we needed!! We loved hanging out by the fire pit and down by the river. The view and location is perfect. Thanks for everything…we will be back! "
The price is NZ$616
includes taxes & fees
24 Sept - 25 Sept
Luxury Waterfront Retreat near New Paltz & the Gunks: Hike, Bike, or Relax!
4-bedrooms with gym+spa access steps from Garlic Festival
Spa
4-bedrooms with gym+spa access steps from Garlic Festival
9.0 out of 10, Wonderful, (12)
"We enjoyed our stay and Chris was very responsive to any questions. Would definitely stay again."
4-bedrooms with gym+spa access steps from Garlic Festival
Charming 2 Bed backyard guesthouse close to Peekskill, WestPoint, & trails.
Aerial view
Charming 2 Bed backyard guesthouse close to Peekskill, WestPoint, & trails.
9.0 out of 10, Wonderful, (22)
"Loved it!! "
Charming 2 Bed backyard guesthouse close to Peekskill, WestPoint, & trails.
Historic Saugerties Home w/ Deck: River Views!
Fridge, microwave, stovetop, dishwasher
Historic Saugerties Home w/ Deck: River Views!
10.0 out of 10, Exceptional, (13)
"Very peaceful location in our favorite Hudson Valley town, sweet Saugerties! The property manager was extremely responsive, the neighbors were very nice — one even recommended a local swimming hole — and the house was very cute and unique. We loved waking up to the sound of birds and the sunrise over the Hudson. We also loved being able to walk into the village center for dinner and ice cream. The house was clean, comfortable, and we very much enjoyed our stay. "
Historic Saugerties Home w/ Deck: River Views!
Candlewood Lakefront 3bd/ 2 bath house w/ 180 degree views!
Outdoor dining
Candlewood Lakefront 3bd/ 2 bath house w/ 180 degree views!
10.0 out of 10, Exceptional, (39)
"We had such a great time! The views are stunning and the house has everything you need to enjoy your stay. The host Kerry was so helpful; we had a small issue with the shower and she had a plumber over within the hour to resolve it. Can’t wait to come back next summer! "
Candlewood Lakefront 3bd/ 2 bath house w/ 180 degree views!
Ukihaus Hudson: Enchanting Hudson Valley A-Frame
TV, fireplace
Ukihaus Hudson: Enchanting Hudson Valley A-Frame
9.4 out of 10, Exceptional, (3)
"My wife and I enjoyed staying in this A-frame with our dog for a few days. It had some simple, yet, well-chosen furnishing and decorations. Importantly, it was clean and welcoming. We were concerned about the proximity to route 87, and indeed you can see cars through gaps in the trees and hear the traffic if you are outside. Inside, however, was very quiet and we couldn't even hear a heavy down pour of rain."
Ukihaus Hudson: Enchanting Hudson Valley A-Frame
Pet-Friendly ‘Pond View Loft' w/ Private Pool!
Interior
Pet-Friendly ‘Pond View Loft' w/ Private Pool!
9.6 out of 10, Exceptional, (11)
"Overall, it seemed like the property manager was not ready for guests. The toilet instantly broke, the pool hadn’t been cleaned in probably weeks, and the apartment had stained sheets. It’s a nice place but really not worth the money."
Pet-Friendly ‘Pond View Loft' w/ Private Pool!
‘A Gathering Den’ 3-bedroom house. HITS-on-the-Hudson.
Smart TV, books, stereo, printers
‘A Gathering Den’ 3-bedroom house. HITS-on-the-Hudson.
10.0 out of 10, Exceptional, (1)
"This property is perfectly located between Saugerties and Kingston with easy access to both. We wanted a place that was easy to explore the area from and we scored with this house. Everything was clean and we were provided with everything we could need, pots & pans, soap & shampoo, washer & dryer--all of it. We also had plenty of room to do the work we brought with us. The house stayed cool the whole time (day & night) and we really enjoyed it. "
‘A Gathering Den’ 3-bedroom house. HITS-on-the-Hudson.
The Studio at the Inn at High Falls
Exterior
The Studio at the Inn at High Falls
8.0 out of 10, Very good, (21)
"Great communication with host. Stayed one night for event at Arrowood Farms (only 10 minutes away). Clean , nicely decorated studio with plenty of light. Lovely yard. Close to all local attractions and dining. Large shower. Great towels and toiletries.TV and A/C worked well. Appreciated the drinking water.Really cozy studio. Has frig, microwave and coffee maker.(also iron and hair dryer). A fabulous stay, although water pressure was a little low, but certainly not a deal breaker. Had people...
The price is NZ$416
includes taxes & fees
24 Sept - 25 Sept
The Studio at the Inn at High Falls
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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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Other property types in Poughkeepsie

The Farm at Hyde Park
Exterior
The Farm at Hyde Park
9.8 out of 10, Exceptional, (61)
"We came up from Brooklyn to see the hot air balloons with my parents and it was just what we needed. Our Host Glen is very gracious and helpful! We loved staying at the Farm. The church and the grounds are beautiful. Glen provided us with fresh eggs, milk and honey. We were also allowed to pick tomatoes from his garden. All very delicious. "
The Farm at Hyde Park
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Property grounds
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
9.8 out of 10, Exceptional, (99)
"Wonderful hilltop location. Beautiful view. Nice apartment. Great hosts. Wish we could have stayed longer! "
The price is NZ$410
includes taxes & fees
1 Oct - 2 Oct
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
'A Place in the Woods' - Cabin on Chloe's Lake on 23 acres near Woodstock, NY
Property grounds
'A Place in the Woods' - Cabin on Chloe's Lake on 23 acres near Woodstock, NY
8.4 out of 10, Very good, (41)
"We had a great time at the cabin! It was the perfect escape from the city. The view was gorgeous, and the cabin had everything we needed. We also tried to use the canoe but the padlock is stuck, it might be rusted/need to be replaced. Otherwise everything was perfect!"
The price is NZ$232
includes taxes & fees
25 Sept - 26 Sept
'A Place in the Woods' - Cabin on Chloe's Lake on 23 acres near Woodstock, NY
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.