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Pleasant Valley Holiday Rentals

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Holiday Rentals in Pleasant Valley

Studio near Millbrook, Poughkeepsie. Close to Polo Club w/ mini farm!

9.2 out of 10, Wonderful, (35)
"I loved the location surrounded by mostly woods and the quiet atmosphere. The hosts are very nice and were very helpful. Everything I needed was inside. I may be back!"
Studio near Millbrook, Poughkeepsie. Close to Polo Club w/ mini farm!

Lakehouse, Private Beach, Kayaks, FirePit, Gym, Movie Room, Pool Table, Air Hock

9.6 out of 10, Exceptional, (74)
"The house is as advertised. Good amount of room. The host was pretty communicative. No complaints from the property. Just wish they had a bigger table for group dinners"
Lakehouse, Private Beach, Kayaks, FirePit, Gym, Movie Room, Pool Table, Air Hock

The Scenic Mansion With Breathtaking View

9.6 out of 10, Exceptional, (11)
"So nice we keep coming back. Can't recommend highly enough and will be back in the spring. "
The Scenic Mansion With Breathtaking View

The Farm at Hyde Park

9.8 out of 10, Exceptional, (63)
"Quiet spot out of the city but not too far from Hudson Valley sites. Large vaulted space, fresh eggs from the hen house next door, sky full of stars at night. Great host!"
The Farm at Hyde Park

NEW! Gated 31 Acre Modern Luxury Estate Heated Pool Hot Tub Gym Movie Theater.

9.6 out of 10, Exceptional, (50)
"Our family enjoyed our time at the property- it was a great place for us all to gather. The property managers were incredibly helpful and responsive to the few things that needed attention during our stay. The pool area is the shining star of this home. You can expect the house/ furnishings to be in mostly good shape and as photographed-. The layout of the bedrooms/ shared bathrooms did surprise us a bit despite careful review of photos and listing video tour. Overall great stay!"
NEW! Gated 31 Acre Modern Luxury Estate Heated Pool Hot Tub Gym Movie Theater.

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

9.4 out of 10, Exceptional, (15)
"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

Mid-Century DJ’s Dream

10.0 out of 10, Exceptional, (23)
"Every thing was good! Thank you for quickly responding to my request to add an additional night. Thank you for being pet friendly."
The price is NZ$272
includes taxes & fees
30 Nov - 1 Dec
Mid-Century DJ’s Dream

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

10.0 out of 10, Exceptional, (74)
"This place was a great place for us to stay on our vacation. Secluded outside of the city, and a short drive down a gravel road, it really feels that you're lost in the woods, but in a good way. If you're up to visit the Gunks, Angry Orchard, the Hudson river, love the beauty of the outdoors, and have other family or friends to visit in the area, definitely consider this home. Host was very responsive and had everything ready for us."
Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.

Esopus Escape: Pool, Hot Tub & Media Room

9.6 out of 10, Exceptional, (19)
"We were in the area for a wedding. The house was great. Hot tub was fabulous. Beautiful couple of days. Just one note for safety: the metal railing on the left side of the steps from the driveway heading up to the house is coming loose or rather, is very, very loose so as to not be useable. Just could be a bit dangerous particularly at night. Otherwise, was absolutely lovely."
Esopus Escape: Pool, Hot Tub & Media Room

Kingston Crawfish Cottage Near Catskills!

9.8 out of 10, Exceptional, (10)
"We enjoyed our stay at the crawfish cottage. It was clean and had everything we needed. The host, Diane, was great, friendly and very responsive. "
Kingston Crawfish Cottage Near Catskills!

1 HR NYC Getaway Awesome Newly Renovated Home on 4 Acres, Stunning Views

9.0 out of 10, Wonderful, (32)
"We enjoyed our stay however, the listing states all the beds are king sized and only 2 are. The other 2 are queen. Also (note for host) we forgot a pair of sunglasses and would like to have them mailed back if they are found, could you contact me if possible."
1 HR NYC Getaway Awesome Newly Renovated Home on 4 Acres, Stunning Views

The Studio at the Inn at High Falls

7.8 out of 10, Good, (22)
"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 Studio at the Inn at High Falls

Mountain View escape

10.0 out of 10, Exceptional, (43)
"Charming. Peaceful. Beautiful. Well-designed. Well-stocked. I cannot recommend this place enough. It is the ideal getaway for an individual or couple. Hope to have a reason to return soon! "
Mountain View escape

Hamptons on the Hudson in South Saugerties

10.0 out of 10, Exceptional, (12)
"Our group of 7 women had a great time in the house. Beautiful property. Nice view of the Hudson. Lots of amenities. Well stocked kitchen. Cozy and comfortable. We enjoyed the Nespresso machine. Lots of room for us to spread out and to hang out together in the living room and enjoy a meal in the dining room. We would definitely stay again. "
Hamptons on the Hudson in South Saugerties

Hilltop A-frame chalet, skyline views, heated pool and hot tub, expansive...

10.0 out of 10, Exceptional, (7)
"Lovely home and well equipped would love to stay again. Great service and communication from stay marquis. Thanks again!"
Hilltop A-frame chalet, skyline views, heated pool and hot tub, expansive...

Esopus Creek modern Tiny house Retreat!

9.6 out of 10, Exceptional, (18)
"Nice little place to crash after a show at Bearsville."
The price is NZ$384
includes taxes & fees
24 Nov - 25 Nov
Esopus Creek modern Tiny house Retreat!

Hiking/Climbing Paradise- walking distance to Mohonk/Gunks/Minnewaska

9.8 out of 10, Exceptional, (90)
"Very close to hiking and biking trails! Beds were comfortable "
Hiking/Climbing Paradise- walking distance to Mohonk/Gunks/Minnewaska

Sexiest Lil Cabin in Saugerties, NY

8.6 out of 10, Excellent, (7)
"We loved our stay here, it was the perfect short getaway. Thanks Alexandria!"
Sexiest Lil Cabin in Saugerties, NY

Beautiful Escape! Hudson Valley LakeHouse. 90min from NYC & 30min from Beacon.

10.0 out of 10, Exceptional, (11)
"This property was even more beautiful than it appeared in the photos. The wooded backyard was also spacious and lovely. We were so happy with the view of the lake and how peaceful the space was. The owners are easy to communicate with and prompt to respond. We will absolutely be going back. "
The price is NZ$1,424
includes taxes & fees
25 Nov - 26 Nov
Beautiful Escape! Hudson Valley LakeHouse. 90min from NYC & 30min from Beacon.

Lake Cottage, Private Beach, Kayaks, FirePit, Grill, 1 hour & 15 Minutes to NYC!

9.4 out of 10, Exceptional, (86)
"Perfectly adorable house that was ideal for our brief getaway. I wish we had been able to use the kayak/canoe but time was tight. The only issue was the driveway which had me holding my breath a bit but luckily we were careful and managed without incident."
Lake Cottage, Private Beach, Kayaks, FirePit, Grill, 1 hour & 15 Minutes to NYC!
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 types of properties in Pleasant Valley you may be interested in

Studio near Millbrook, Poughkeepsie. Close to Polo Club w/ mini farm!

9.2 out of 10, Wonderful, (35)
"I loved the location surrounded by mostly woods and the quiet atmosphere. The hosts are very nice and were very helpful. Everything I needed was inside. I may be back!"
Studio near Millbrook, Poughkeepsie. Close to Polo Club w/ mini farm!

Best Western Plus Kingston Hotel And Conference Center

2.5 star property
7.8 out of 10, Good, (1008)
"Excellent thread "
The price is NZ$268
includes taxes & fees
1 Dec - 2 Dec
Best Western Plus Kingston Hotel And Conference Center

DoubleTree by Hilton Poughkeepsie

4.0 star property
8.2 out of 10, Very good, (1015)
"N/A"
The price is NZ$209
includes taxes & fees
1 Dec - 2 Dec
DoubleTree by Hilton Poughkeepsie
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.
Beautiful view of the beach with palm trees

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Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.

Frequently asked questions

Are there holiday rentals in Pleasant Valley?

Yes, there are holiday rentals in Pleasant Valley close to Innisfree Garden, or you can select a more secluded option if you're looking for a relaxing stay. Pleasant Valley is known for its shopping and restaurants. Make sure you have time to check out the parks while you're in the area.

What are some of the best holiday rentals that Pleasant Valley has to offer?

The Farm at Hyde Park: This holiday home rental outside of Pleasant Valley is located in a rural location, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. Kick off your shoes and enjoy yourself with a garden and a selection of games.

How many holiday rentals are there in Pleasant Valley?

Choose from 7 Expedia holiday rentals in Pleasant Valley for a memorable holiday.

What’s there to see and do in Pleasant Valley?

Innisfree Garden and James Baird State Park are a couple of lovely local spots to get outside and enjoy nature. In the wider area, you’ll find Eleanor Roosevelt National Historic Site and Vassar College.

What are holiday rentals like in Pleasant Valley?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Pleasant Valley. Holiday rentals offer extras like kitchens and laundry facilities so you'll feel just like you're at home. If you're concerned about a clean environment, a holiday rental can provide a sense of seclusion away from public hotel lifts and bustling concierge desks while still allowing you to travel. 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 option for a small group gathering.