Photo by louann ohora

Pleasant Valley Holiday Rentals

Save an average of 15% on thousands of properties with Expedia Rewards

Most properties are fully refundable. Because flexibility matters.

Search over 2.9 million properties and 550 airlines worldwide

Find properties with these dates

Holiday Rentals in Pleasant Valley

Studio near Millbrook, Poughkeepsie. Close to Polo Club w/ mini farm!
9.2 out of 10, Wonderful, (27)
"For a woodsy getaway close to real highways, here’s your spot. A good home base for local activities. Cute not chic, clean and functional. Chickens and goats on the property added a great farm with no work charm."
Studio near Millbrook, Poughkeepsie. Close to Polo Club w/ mini farm!
The Farm at Hyde Park
9.8 out of 10, Exceptional, (47)
"Very unusual, appealing proportions, well stocked, perfect location"
The Farm at Hyde Park
Cozy Countryside Barn with Spa/Fireplace/Enclosed YardFire Pits
9.8 out of 10, Exceptional, (35)
"This is a cozy property in a very rural setting. The host is extremely responsive and very thorough. It is quiet and private. The furniture and bed are very comfortable. The wood burning stove is a pellet stove which provides enough heat to take the edge off. The hot tub could comfortably fit 4 people. The Village of Cold Spring is less than 10 minutes away, as is the Interstate 84 bridge across the Hudson. If you want to make your own food, bring it. There is no grocery store nearby."
Cozy Countryside Barn with Spa/Fireplace/Enclosed YardFire Pits
Save an average of 15% on thousands of hotels when you're signed in
Lakeview Home 3 Private Beaches w/ Kayaks, on Squantz Pond
9.6 out of 10, Exceptional, (58)
"Property manager was very kind and responsive. Greatly enjoyed the views of the pond and the basement pool and ping pong tables. Great time playing these games with mybson as the weather wasn't conducive for water activities."
Lakeview Home 3 Private Beaches w/ Kayaks, on Squantz Pond
Hudson River View Suite-idyllic getaway with fireplace & private deck-75 min NYC
10.0 out of 10, Exceptional, (35)
"Very nice property, immaculately clean and very close to the Riverside Art Venue. Both quiet and convenient for my time in Newburgh. I would definitely stay here again."
The price is NZ$296
includes taxes & fees
27 May - 28 May
Hudson River View Suite-idyllic getaway with fireplace & private deck-75 min NYC
Exquisite Mtn Chalet 5 min to Woodstock's Best Scenic Walks, we have generator.
10.0 out of 10, Exceptional, (81)
"We enjoyed our stay at this property. The location is very private and comfortable. The kitchen is well stocked with amenities."
The price is NZ$446
includes taxes & fees
21 May - 22 May
Exquisite Mtn Chalet 5 min to Woodstock's Best Scenic Walks, we have generator.
Mid-Century DJ’s Dream
10.0 out of 10, Exceptional, (13)
"Our stay was quite nice, the place looked as the pictures showed it to be which is just amazing. everything was music themed and our host had an amazing selection of vinyls. The only complaints I would say I had was the small flying bugs near the Tv and we weren’t provided paper towels. Overall it was a nice place for the night and the property itself was beautiful."
The price is NZ$353
includes taxes & fees
27 May - 28 May
Mid-Century DJ’s Dream
@iHeartNYState 4BR. Hot Tub Jacuzzi Fireplace
7.0 out of 10, Good, (4)
"Our group were in town for a wedding nearby in Garrison. The stay here was ideal in terms of space and proximity to the wedding venue. Wished we could stay longer! The host was accommodating by letting us check-in earlier."
The price is NZ$982
includes taxes & fees
21 May - 22 May
@iHeartNYState 4BR. Hot Tub Jacuzzi Fireplace
Mountain View escape
10.0 out of 10, Exceptional, (24)
"We've stayed in a number of VRBOs and none have been as well-appointed and welcoming as this Mountain View Escape home. Privacy and space, while close to wonderful towns and places to explore. Highly recommend!"
Mountain View escape
The Higashi- comfy mountain home in New Paltz
9.4 out of 10, Exceptional, (6)
"We enjoyed our stay. The home is comfortable. It is stocked with better supplies than any rental we have ever stayed in. It is in a nice location. Not far from the small town restaurants and shopping. We are JW's and felt this was in a great location to visit all the bethel locations and there is a Kingdom Hall a few minutes away with a warm and friendly congregation."
The price is NZ$435
includes taxes & fees
20 May - 21 May
The Higashi- comfy mountain home in New Paltz
Luxury retreat w/ private deck, garden, firepit on organic farm
10.0 out of 10, Exceptional, (10)
"The property and the yurt were absolutely beautiful. And if you're looking to get AWAY, this is the place. It rained most of the weekend, and we still had an amazing time. Communication was terrific. Thank you so much, John."
Luxury retreat w/ private deck, garden, firepit on organic farm
Dog-Friendly Hudson Valley Escape with Hot Tub & Jacuzzi
10.0 out of 10, Exceptional, (11)
"Perfect spot to visit grandkids Lots to do"
The price is NZ$396
includes taxes & fees
21 May - 22 May
Dog-Friendly Hudson Valley Escape with Hot Tub & Jacuzzi
Cabin in the heart of the Hudson Valley, Cabin 4
8.4 out of 10, Very good, (11)
"Everything was as it says it was. Place was spotless. In the evening and morning you didn’t hear any traffic noise at all. Was quiet and peaceful. Communication with the property owner was outstanding."
The price is NZ$270
includes taxes & fees
19 May - 20 May
Cabin in the heart of the Hudson Valley, Cabin 4
The Studio at the Inn at High Falls
8.4 out of 10, Very good, (17)
"Love staying at The Studio at the Inn at High Falls. It truly is my new home away from home. Soo Clean, Comfortable and incredible friendly helpful people who own and work there. Again Thank you Frank and too a New Year. Patricia"
The price is NZ$428
includes taxes & fees
16 May - 17 May
The Studio at the Inn at High Falls
Cozy country efficiency in the Hudson Valley
9.8 out of 10, Exceptional, (39)
"Quiet, clean and very comfortable. Beautiful property located just minutes from town. Will definitely stay here again."
The price is NZ$356
includes taxes & fees
4 Jun - 5 Jun
Cozy country efficiency in the Hudson Valley
Enjoy a cozy, quiet spot off the main roads but close to hiking/biking trails!
9.6 out of 10, Exceptional, (18)
"Wow Ryan, the owner was really nice guy just a great place to relax and enjoy firepit,.mountain views, outdoor sitting with tv, very private!!! I'll give this one 10+ review!!!!!"
The price is NZ$470
includes taxes & fees
16 May - 17 May
Enjoy a cozy, quiet spot off the main roads but close to hiking/biking trails!
Campfire Cottage: Fireplace, fire pit & no chores!
10.0 out of 10, Exceptional, (15)
"Matt is a wonderful host! I was very impressed by the cleanliness of the 1 bedroom cabin and how much thought went into providing guests with everything they need. I stayed for four nights and was very comfortable. The bed was so comfortable I slept great. Kingston is a city so some noise is expected. The neighborhood is very quiet at night and you can hear a little noise occasionally in the distance. Matt provides an adjustable sound machine. I put it on low and slept like a baby. Matt is very...
The price is NZ$349
includes taxes & fees
21 May - 22 May
Campfire Cottage: Fireplace, fire pit & no chores!
Restored Farm House in quaint Hudson Valley Town of Red Hook, Dutchess County
10.0 out of 10, Exceptional, (10)
"We had a lovely weekend at this updated farm house. The house is a great combination of old comfortable farm house and updated and clean kitchens and bathrooms. We loved having Artie, the kitty, as our welcoming party."
Restored Farm House in quaint Hudson Valley Town of Red Hook, Dutchess County
Cozy Countryside Cottage with Spa/Fireplace//Enclosed Yard/Fire Pits
9.6 out of 10, Exceptional, (35)
"Three nights here as we toured the area. Check in was easy. We were able to access the VRBO app 30 minutes prior to our arrival. By the time we reached the driveway, Ruben had sent the access code.The road to the house is gravel and only wide enough for one car. We were glad we had arrived during the day.The house has an antique store vibe. Lots of books for a rainy day activity. FYI, the photos on the listing are a bit different from what we saw in the rooms. The dining table is larger with...
Cozy Countryside Cottage with Spa/Fireplace//Enclosed Yard/Fire Pits
Cabin in the heart of the Hudson Valley, Cabin 2
9.4 out of 10, Exceptional, (3)
"Great tiny house for a stay upstate. Check in was easy and the place is clean!"
The price is NZ$270
includes taxes & fees
19 May - 20 May
Cabin in the heart of the Hudson Valley, Cabin 2
Don't see what you're looking for?
See all available properties in Pleasant Valley
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.

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, (27)
"For a woodsy getaway close to real highways, here’s your spot. A good home base for local activities. Cute not chic, clean and functional. Chickens and goats on the property added a great farm with no work charm."
Studio near Millbrook, Poughkeepsie. Close to Polo Club w/ mini farm!
Best Western Plus Kingston Hotel And Conference Center
2.5 star property
8.0 out of 10, Very good, (1001)
"All of the staff was super friendly and helpful. The building is a little tricky to navigate. Great food in the dining area, and overall all great stay. "
The price is NZ$259
includes taxes & fees
2 Jun - 3 Jun
Best Western Plus Kingston Hotel And Conference Center
HYATT house Fishkill/Poughkeepsie
3.0 star property
8.6 out of 10, Excellent, (1000)
"Great"
The price is NZ$263
includes taxes & fees
29 May - 30 May
HYATT house Fishkill/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 8 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.