Photo by louann ohora

Pleasant Valley Holiday Rentals

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
19 Jul - 20 Jul
Tomorrow
20 Jul - 21 Jul
Next weekend
25 Jul - 27 Jul
In two weeks
1 Aug - 3 Aug

Holiday Rentals in Pleasant Valley

Mid Century Modern Studio w/ Full Kitchen - Newly Built
Fridge, microwave, oven, stovetop

Mid Century Modern Studio w/ Full Kitchen - Newly Built

8.0 out of 10, Very good, (1)
"Super cute, clean, and convenient for our quick trip to The Millbrook School."
The price is HK$1,530
HK$1,956 total
includes taxes & fees
20 Jul - 21 Jul
Mid Century Modern Studio w/ Full Kitchen - Newly Built
Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.
Living area

Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.

9.8 out of 10, Exceptional, (7)
"Great spot, wonderful host. Would recommend to anyone!"
The price is HK$1,589
HK$3,134 total
includes taxes & fees
22 Jul - 23 Jul
Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.
Beautiful Escape! Hudson Valley LakeHouse. 90min from NYC & 30min from Beacon.
Fridge, microwave, oven, stovetop

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

10.0 out of 10, Exceptional, (15)
"We had a great stay and had everything we needed!"
The price is HK$3,079
HK$6,246 total
includes taxes & fees
22 Jul - 23 Jul
Beautiful Escape! Hudson Valley LakeHouse. 90min from NYC & 30min from Beacon.
Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park
Exterior

Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park

9.0 out of 10, Wonderful, (9)
"Truly a hidden gem. The property and home were nothing short of extraordinary. For those looking for a great location with access to hiking and a one of a kind experience this is the place."
The price is HK$1,194
HK$2,025 total
includes taxes & fees
20 Jul - 21 Jul
Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park
The George is an elegant restored home in the Hudson Valley
Interior

The George is an elegant restored home in the Hudson Valley

9.0 out of 10, Wonderful, (4)
"Nice big house in a quiet location. "
The price is HK$4,520
HK$7,173 total
includes taxes & fees
28 Jul - 29 Jul
The George is an elegant restored home in the Hudson Valley
rural, serene + sophisticated space
Interior

rural, serene + sophisticated space

10.0 out of 10, Exceptional, (7)
"Beautiful property with unique accommodations in the Hudson Valley"
The price is HK$2,346
HK$2,899 total
includes taxes & fees
23 Jul - 24 Jul
rural, serene + sophisticated space
Rustic Cabin in Fishkill!
Exterior

Rustic Cabin in Fishkill!

10.0 out of 10, Exceptional, (1)
"Beautiful property with many different areas to explore. We originally intended to spend more time in beacon but decided it was more fun hanging out here. "
The price is HK$2,158
HK$3,291 total
includes taxes & fees
21 Jul - 22 Jul
Rustic Cabin in Fishkill!
Chestnut on Willow Lake
Private kitchen

Chestnut on Willow Lake

9.0 out of 10, Wonderful, (2)
"We absolutely loved our stay in Chestnut—the home was spotless and comfortable, the property was terrific (the lake was perfect for swimming, boating, and fishing), and the owners/management were all very friendly and helpful. We definitely plan to return!"
The price is HK$3,139
HK$4,565 total
includes taxes & fees
21 Jul - 22 Jul
Chestnut on Willow Lake
Hickory on Willow Lake
Children’s area

Hickory on Willow Lake

9.0 out of 10, Wonderful, (2)
"Cute cottage on nice grounds with a small lake. Kayaks and life jackets available for use was a big plus"
The price is HK$3,335
HK$4,826 total
includes taxes & fees
23 Jul - 24 Jul
Hickory on Willow Lake
Charming 2-bedroom Guest Suite with Pool Access and Fitness Room
Pool

Charming 2-bedroom Guest Suite with Pool Access and Fitness Room

6.0 out of 10, (1)
"Property was very clean and nicely decorated. There isn’t really a living room to hang out. Very difficult for 3 adults to all hang out together. When I booked I was more concerned about the sleeping area so I assumed there was a living room. The guest suite is in the basement of home in a nice neighborhood."
The price is HK$942
HK$1,953 total
includes taxes & fees
20 Jul - 21 Jul
Charming 2-bedroom Guest Suite with Pool Access and Fitness Room
Spacious New Luxurious holiday house in lovely Hudson Valley
Terrace/patio

Spacious New Luxurious holiday house in lovely Hudson Valley

10.0 out of 10, Exceptional, (11)
"We loved our stay at this gorgeous home & we will definitely book it again in the future!"
The price is HK$3,284
HK$5,828 total
includes taxes & fees
30 Jul - 31 Jul
Spacious New Luxurious holiday house in lovely Hudson Valley
Rhinebeck Inn Suite with Private Deck
Exterior

Rhinebeck Inn Suite with Private Deck

2.0 star property
The price is HK$2,003
HK$2,570 total
includes taxes & fees
29 Jul - 30 Jul
Rhinebeck Inn Suite with Private Deck
Cozy Rhinebeck Inn Suite
Exterior

Cozy Rhinebeck Inn Suite

10.0 out of 10, Exceptional, (2)
The price is HK$1,823
HK$2,340 total
includes taxes & fees
29 Jul - 30 Jul
Cozy Rhinebeck Inn Suite
Rhinebeck Inn Suite with Private Living Room
Exterior

Rhinebeck Inn Suite with Private Living Room

The price is HK$2,112
HK$2,710 total
includes taxes & fees
29 Jul - 30 Jul
Rhinebeck Inn Suite with Private Living Room
Rhinebeck Inn Suite with a Private Deck
Terrace/patio

Rhinebeck Inn Suite with a Private Deck

The price is HK$2,184
HK$2,800 total
includes taxes & fees
29 Jul - 30 Jul
Rhinebeck Inn Suite with a Private Deck
Rhinebeck Inn Suite with Private Deck and Fire Pit
Exterior

Rhinebeck Inn Suite with Private Deck and Fire Pit

The price is HK$2,202
HK$2,829 total
includes taxes & fees
29 Jul - 30 Jul
Rhinebeck Inn Suite with Private Deck and Fire Pit
Historic Hudson Valley Estate
5 bedrooms, desk, iron/ironing board, travel cot

Historic Hudson Valley Estate

The price is HK$7,840
HK$12,219 total
includes taxes & fees
28 Jul - 29 Jul
Historic Hudson Valley Estate
Modern Converted Barn with Hot Tub!
Interior

Modern Converted Barn with Hot Tub!

10.0 out of 10, Exceptional, (4)
"The house has a big open floor plan with extra large windows letting light and views in. The bedrooms are comfortable and the kitchen is well equipped. Big playroom was heaven for our toddler. Highly recommend.this property."
The price is HK$4,120
HK$6,739 total
includes taxes & fees
21 Jul - 22 Jul
Modern Converted Barn with Hot Tub!
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
Outdoor dining

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

9.8 out of 10, Exceptional, (25)
"Plenty of room for my family"
The price is HK$2,033
HK$2,628 total
includes taxes & fees
10 Aug - 11 Aug
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
Beautiful, Spacious, 5 Acre Hudson Valley Family Retreat
Outdoor dining

Beautiful, Spacious, 5 Acre Hudson Valley Family Retreat

10.0 out of 10, Exceptional, (4)
"Our stay was only a couple nights but it was what we expected. I would recommend this property. Had a great stay."
The price is HK$2,550
HK$4,930 total
includes taxes & fees
27 Jul - 28 Jul
Beautiful, Spacious, 5 Acre Hudson Valley Family Retreat
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Pleasant Valley Hotel Reviews

Hampton Inn by Hilton New Paltz

Hampton Inn by Hilton New Paltz

10/10 Excellent
"Staff was friendly and accommodating. Pool, gym and all public areas were immaculate. Was well staffed with knowledgeable employees. "
marie 2-night trip
Posted 14 hours ago
Hampton Inn by Hilton New Paltz

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?

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.