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Pleasant Valley Holiday Rentals

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Holiday Rentals in Pleasant Valley

Hamptons on the Hudson in South Saugerties

10.0 out of 10, Exceptional, (14)
"We had an absolutely wonderful stay at this Vrbo! From the moment we arrived, everything was spotless, beautifully decorated, and thoughtfully equipped with everything we needed. The hosts went above and beyond to ensure a comfortable and seamless experience, providing clear instructions and even thoughtful touches that made us feel right at home.The location was perfect—close enough to attractions and restaurants but still peaceful and private. The beds were incredibly comfortable, the kitchen...
Hamptons on the Hudson in South Saugerties

Esopus Creek modern Tiny house Retreat!

9.8 out of 10, Exceptional, (23)
"Great little house for the holidays. We were looking for a place nearby or family where we could have our own space but still be close by. "
The price is NZ$389
includes taxes & fees
6 Mar - 7 Mar
Esopus Creek modern Tiny house Retreat!

The Philip Johnson Wolfhouse

10.0 out of 10, Exceptional, (3)
"This house is an architectural gem with great views to the Hudson river and very close to Dia Beacon and really nice hikes. We were a group of 7 and really enjoyed our time together during our stay. Jeremy was really nice and accommodating. I highly recommend this house."
The Philip Johnson Wolfhouse

Spacious New Luxurious holiday house in lovely Hudson Valley

9.8 out of 10, Exceptional, (8)
"The house had room for all of us, spacious and comfortable with modern amenities. We enjoyed the large open kitchen, well equipped for making big meals, and especially loved the walk in pantry with sink, oven and coffee bar. The beds were comfy, the bathrooms deluxe. Large couch and huge TV in living room with cozy gas fireplace for us to gather and relax. Located on a quiet cul de sac, easy to get to local attractions. We enjoyed every minute of our stay."
Spacious New Luxurious holiday house in lovely Hudson Valley

Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo

10.0 out of 10, Exceptional, (2)
"Communication was easy, location and parking was great! Very clean and cozy!"
The price is NZ$509
includes taxes & fees
13 Mar - 14 Mar
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo

Lakehouse; Kayaks, Grill, FirePit, Gym, Movie Room, Pool Table, Air Hockey etc!

9.6 out of 10, Exceptional, (83)
"No complaints. Stayed during the winter so ne er got the full experience with the lake but it was a great home."
Lakehouse; Kayaks, Grill, FirePit, Gym, Movie Room, Pool Table, Air Hockey etc!

Brand New House with Huge patio overlooks Esopus Creek at Lake Katrine

10.0 out of 10, Exceptional, (8)
"My family and I had a lovely stay! The home is beautiful and comfortable with all the amenities that we needed, including a crib as we were traveling with a newborn. Not much in the immediate vicinity but a short drive to Kingston. Smooth communication and easy checkin/checkout process."
The price is NZ$588
includes taxes & fees
3 Mar - 4 Mar
Brand New House with Huge patio overlooks Esopus Creek at Lake Katrine

Hidden Charm in Hudson Valley In Dutchess County

2.0 star property
10.0 out of 10, Exceptional, (13)
"thank you to the host, she was responsive, the home was amazing, clean, secluded, perfect size for our family and the property was beautiful. we loved having 2 beds on the main floor, as my mom is elderly, so no stairs was incredibly convenient. house had all the supplies we needed to cook/clean, so it was just terrific!! Thank you!"
Hidden Charm in Hudson Valley In Dutchess County

Lakehouse, Boat Dock, Kayaks, Fire-Pit, King Bed, 1 Hour & 15 Min from NYC etc!

9.4 out of 10, Exceptional, (9)
"We stayed here for work event and the location was perfect. Not too close, not too far away. Its snowed one evening but the driveway was not slippery at all. The house was very clean and kept in order. Plenty of room in the bedrooms and bathroom. The operational fireplace was also an added bonus. "
Lakehouse, Boat Dock, Kayaks, Fire-Pit, King Bed, 1 Hour & 15 Min from NYC etc!

Mid-Century DJ’s Dream

10.0 out of 10, Exceptional, (27)
"When I found the place online, it was just the right place for us, peace and quiet. The place was just like the pictures and if I have to described it in one word (COZY) Kevin, the owner met us and helped us and walked us through the place and has a Washer/Dryer. The weekend was perfect, we got snowed in which was perfect in which we order in and Netflix and chilled, PERFECT Timing.Thank you Kevin, we will see you again!"
The price is NZ$309
includes taxes & fees
1 Mar - 2 Mar
Mid-Century DJ’s Dream

Private Lakefront Home With Kayaks * Stunning Sunsets * Panoramic View

10.0 out of 10, Exceptional, (281)
"Beautiful, quiet property that was a great getaway from the city. A pair of bald eagles were circling the lake which was a really amazing surprise! "
The price is NZ$469
includes taxes & fees
11 Mar - 12 Mar
Private Lakefront Home With Kayaks * Stunning Sunsets * Panoramic View

Scenic New Paltz Escape: River Views, Hot Tub & Deck | Dream House in the Gunks

2.0 star property
10.0 out of 10, Exceptional, (1)
"My husband and I had an amazing time. Absolutely beautiful home, great location, and overall amazing experience. "
The price is NZ$704
includes taxes & fees
10 Mar - 11 Mar
Scenic New Paltz Escape: River Views, Hot Tub & Deck | Dream House in the Gunks

The Farm at Hyde Park

9.8 out of 10, Exceptional, (65)
"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

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

9.4 out of 10, Exceptional, (18)
"We had a friend group boardgaming weekend and this was perfect for our purposes. The table was large enough for our biggest games and the pool table doubled as a backup playing space. The race cars are a nice touch of whimsy too :-) Our only suggestion would be to replace the oversized, too-low chandelier over the table but really only a minor thing."
Lakehouse Boat Dock, Kayaks, Fire-Pit, Pool Table, Air Hockey, Hammock, King Bed

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

10.0 out of 10, Exceptional, (75)
"We loved our stay. It was great for a family Thanksgiving"
Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.

Mountain View escape

10.0 out of 10, Exceptional, (46)
"Can’t wait to go back, if I could move this home to Myrtle Beach I would. Fantastic communication with homeowner, great location. Homeowner keeps the home stocked with goodies, extra plus! Very cozy and Quiet it’s a 10 Star "
Mountain View escape

NEW! LAKE FRONT, Private Dock, Fire Pit, Paddle Boards, Kayaks & Rec Room!

10.0 out of 10, Exceptional, (3)
"First time booking and the place was perfect, beautiful views, real cozy vibes, and the host did a great job to attend at anything we needed "
NEW! LAKE FRONT, Private Dock, Fire Pit, Paddle Boards, Kayaks & Rec Room!

Luxe Studio 4 On Main Street -Luxury Steam Shower, Views! Kitchen, Washer/ Dryer

10.0 out of 10, Exceptional, (32)
"Nice."
The price is NZ$402
includes taxes & fees
4 Mar - 5 Mar
Luxe Studio 4 On Main Street -Luxury Steam Shower, Views! Kitchen, Washer/ Dryer

Luxurious & Enchanting Log House in Heart of Hudson Valley/Catskills, Upstate NY

10.0 out of 10, Exceptional, (36)
"We rented this house for ourselves and our friends for our wedding weekend around the corner. It was the best decision, large group and we had plenty of places to sleep, the yard gave ample space for activities, the sound system kept us entertained, and the kitchen made hosting a large group a breeze. Yuri was amazing in making himself available and our stay memorable. Can’t wait to visit again!"
Luxurious & Enchanting Log House in Heart of Hudson Valley/Catskills, Upstate NY

NEW! Gated 21 Acre Modern Luxury Estate Heated Pool Hot Tub Gym Movie Theater.

9.6 out of 10, Exceptional, (51)
"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 21 Acre Modern Luxury Estate Heated Pool Hot Tub Gym Movie Theater.
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

Best Western Plus Kingston Hotel And Conference Center

2.5 star property
8.0 out of 10, Very good, (1001)
"Quiet, clean and breakfast."
The price is NZ$240
includes taxes & fees
16 Mar - 17 Mar
Best Western Plus Kingston Hotel And Conference Center

HYATT house Fishkill/Poughkeepsie

3.0 star property
8.8 out of 10, Excellent, (1005)
"Had a good one day stay at HYATT Place Fishkill. Service counter people were friendly and welcoming. The room was spacious, clean and well appointed with amenities: microwave, fridge, coffee machine & suppliies. Breakfast served was good and plentiful. Good value!"
The price is NZ$204
includes taxes & fees
12 Mar - 13 Mar
HYATT house Fishkill/Poughkeepsie

Wildflower Farms, Auberge Resorts Collection

5.0 star property
9.4 out of 10, Exceptional, (46)
"Every aspect of this resort is top notch. We had a magical stay. "
The price is NZ$1,489
includes taxes & fees
16 Mar - 17 Mar
Wildflower Farms, Auberge Resorts Collection
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?

Hamptons on the Hudson in South Saugerties: This holiday home rental outside of Pleasant Valley is located on a river, and has an outdoor pool, a fireplace and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a balcony, a garden and a selection of games so that you can immerse yourself in your holiday.

How many holiday rentals are there in Pleasant Valley?

Choose from 6 Expedia holiday rentals in Pleasant Valley for a memorable holiday.

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

While exploring the area, visit family-friendly sights like Mid-Hudson Civic Center, or get outside and enjoy nature at Innisfree Garden. In the wider area, you’ll find James Baird State Park and Eleanor Roosevelt National Historic Site.

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.