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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 Boat Dock, Kayaks, Fire-Pit, Pool Table, Air Hockey, Hammock, King Bed
9.4 out of 10, Exceptional, (12)
"Such a beautiful property! And easy communication with the host. I will definitely be referring family and friends for the future "
Lakehouse Boat Dock, Kayaks, Fire-Pit, Pool Table, Air Hockey, Hammock, King Bed
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
Mid-Century DJ’s Dream
10.0 out of 10, Exceptional, (21)
"Kevin was great with being flexible about check in time! My sister and I didn't get in until past 9pm and it was no problem! And it's a plus that he's very pet friendly as I had my dog and cat with me!"
The price is NZ$266
includes taxes & fees
20 Nov - 21 Nov
Mid-Century DJ’s Dream
Lakehouse, Private Beach, Kayaks, FirePit, Gym, Movie Room, Pool Table, Air Hock
9.6 out of 10, Exceptional, (72)
"Awesome stay!"
Lakehouse, Private Beach, Kayaks, FirePit, Gym, Movie Room, Pool Table, Air Hock
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
Lake Cottage, Private Beach, Kayaks, FirePit, Grill, 1 hour & 15 Minutes to NYC!
9.4 out of 10, Exceptional, (84)
"Well appointed cabin was perfect for a quick weekend up to visit friends. Would love to come back in warm weather to take advantage of the proximity to the beautiful lake. Thanks!"
Lake Cottage, Private Beach, Kayaks, FirePit, Grill, 1 hour & 15 Minutes to NYC!
Romantic Log Cabin on Privately-Owned Lake with Fireplace
9.8 out of 10, Exceptional, (80)
"Amazing location on a completely private small lake just a few minutes off the Taconic Parkway. Host is very helpful, and very artistic. Sleeping on a pull out couch was initially off-putting, but it is very high quality and fairly comfortable, and works for the space. So many birds to see and hear! Nice hiking trails on the large property, which has adjacent preserved land. "
Romantic Log Cabin on Privately-Owned Lake with Fireplace
Campfire Cottage: Fireplace, fire pit & no chores!
10.0 out of 10, Exceptional, (20)
"Cute Clean Comfy bed "
The price is NZ$307
includes taxes & fees
6 Nov - 7 Nov
Campfire Cottage: Fireplace, fire pit & no chores!
Beautiful Escape! Hudson Valley LakeHouse. 90min from NYC & 30min from Beacon.
10.0 out of 10, Exceptional, (10)
"We wanted to spend a night in cold spring after a hike but couldn't find anything last minute in the area, so ended up booking this lovely property a little bit away. At first I was skeptical because of the drive (about 40-45 mins if I remember correctly). But I'm so glad we ended up doing this. Cold spring was just so busy and crowded, we couldn't even get lunch easily. The property is located right across a lake and is on a rather quite street. We reached the property around 5pm just in time...
The price is NZ$1,333
includes taxes & fees
12 Nov - 13 Nov
Beautiful Escape! Hudson Valley LakeHouse. 90min from NYC & 30min from Beacon.
Mountain View escape
10.0 out of 10, Exceptional, (41)
"Very comfortable, clean, quiet cottage where the host's attention to detail and provision of many small extras make for a very pleasant stay."
Mountain View escape
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
Esopus Escape: Pool, Hot Tub & Media Room
9.6 out of 10, Exceptional, (17)
"Beautiful wooded lot, very private and quiet. "
Esopus Escape: Pool, Hot Tub & Media Room
Spectacular Short Term Vacation Rental in Kent
9.6 out of 10, Exceptional, (76)
"Hosts were great and very responsive and the property was fantastic and really peaceful. Highly recommend staying there!"
Spectacular Short Term Vacation Rental in Kent
Hudson River View Suite-idyllic getaway with fireplace & private deck-75 min NYC
10.0 out of 10, Exceptional, (49)
"Everything was great...except the smell...moldy? Old house smell? "
Hudson River View Suite-idyllic getaway with fireplace & private deck-75 min NYC
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!
Oversized Country house, Quiet Retreat & Gathering space ~NEW !!!
9.8 out of 10, Exceptional, (19)
"Very comfortable and clean house that accommodated the 20 of us well. Upstairs rooms all have adjoining bathrooms. However there is no bathroom in the basement or in the bedroom above the game room. Since the closest available bathroom was on the first floor these bedrooms were somewhat inconvenient. Otherwise we had a very enjoyable stay with lovely outdoor space and comfortable accommodations."
Oversized Country house, Quiet Retreat & Gathering space ~NEW !!!
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.
Cabin in the heart of the Hudson Valley, Cabin 4
8.8 out of 10, Excellent, (17)
"The description of the property was accurate; however, a few things surprised me that would have affected my decision to book or not. First, the house is located beside a busy road where traffic is moving all hours of the day and night at 35-55 mph. For some, this isn't a big deal. For others, it's not as quiet as described. Thankfully, I was delighted to see the room provided a noise machine. Secondly, there is no fan. Only the A/C and heater provided any air movement if you didn't want the...
The price is NZ$273
includes taxes & fees
6 Nov - 7 Nov
Cabin in the heart of the Hudson Valley, Cabin 4
Gardiner Modern Farm House.
8.6 out of 10, Excellent, (8)
"Very nice area near plenty of nice things to do and see. Comfortable and clean as well."
The price is NZ$788
includes taxes & fees
11 Nov - 12 Nov
Gardiner Modern Farm House.
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, (1000)
"Good and convenient"
The price is NZ$246
includes taxes & fees
17 Nov - 18 Nov
Best Western Plus Kingston Hotel And Conference Center
DoubleTree by Hilton Poughkeepsie
4.0 star property
8.2 out of 10, Very good, (1000)
"The surrounding neighborhood is the ghetto but the hotel and staff were great!"
The price is NZ$213
includes taxes & fees
2 Dec - 3 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.

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.