Photo by louann ohora

Pleasant Valley Vacation Rentals

Start date: Check-in selected.
To Date
End date: Check-out

    Change your mind

    Book hotels with free cancellation

    Treat yourself

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

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
Oct 29 - Oct 30
Tomorrow
Oct 30 - Oct 31
This weekend
Oct 31 - Nov 2
Next weekend
Nov 7 - Nov 9

Vacation Rentals in Pleasant Valley

Outdoor dining
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
9.6 out of 10, Exceptional, (42)
"Plenty of seating & comfortable beds were a plus! The theatre room was really fun for grandkids!"
United States
Lisa B.
The price is ￥39,412
￥50,265 total
includes taxes & fees
Nov 3 - Nov 4
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
Outdoor dining
Lakehouse Boat Dock, Kayaks, Fire-Pit, Pool Table, Air Hockey, Hammock, King Bed
Lakehouse Boat Dock, Kayaks, Fire-Pit, Pool Table, Air Hockey, Hammock, King Bed
9.4 out of 10, Exceptional, (30)
"Loved it. "
United States
Mike P.
Lakehouse Boat Dock, Kayaks, Fire-Pit, Pool Table, Air Hockey, Hammock, King Bed
Terrace/patio
Hamptons on the Hudson in South Saugerties
Hamptons on the Hudson in South Saugerties
10.0 out of 10, Exceptional, (33)
"Beautiful home and fantastic pool. Responsive and friendly host. Our whole family had a great time! "
United States
Courtney W.
Hamptons on the Hudson in South Saugerties
Property grounds
Cabin in the heart of the Hudson Valley, Cabin 2
Cabin in the heart of the Hudson Valley, Cabin 2
9.4 out of 10, Exceptional, (27)
"We stayed here a few years ago and loved the convenience of this property. When we returned to the area, we immediately started by looking for this property again. It’s clean, no fuss, easy check in, and precisely what we needed!"
United States
Erika S.
The price is ￥16,587
￥26,784 total
includes taxes & fees
Nov 2 - Nov 3
Cabin in the heart of the Hudson Valley, Cabin 2
Exterior
The Farm at Hyde Park
The Farm at Hyde Park
9.8 out of 10, Exceptional, (83)
"Great place to stay. Glen was a great host and give us different items from the area to try from local farms"
United States
Keith M.
The Farm at Hyde Park
Interior
Large,Cozy,Bright Apartment, Business Themed.
Large,Cozy,Bright Apartment, Business Themed.
9.0 out of 10, Wonderful, (15)
"Very cozy stay with responsive host"
United States
Adhith P.
The price is ￥65,737
￥105,154 total
includes taxes & fees
Oct 30 - Oct 31
Large,Cozy,Bright Apartment, Business Themed.
Outdoor dining
Esopus Creek modern Tiny house Retreat!
Esopus Creek modern Tiny house Retreat!
9.8 out of 10, Exceptional, (59)
"The property was beautiful. Quiet area but close enough to all the places we wanted to go. Our hosts were very gracious, attentive and friendly. Enjoyed our weekend retreat. "
United States
Rebecca
The price is ￥22,597
￥36,728 total
includes taxes & fees
Nov 12 - Nov 13
Esopus Creek modern Tiny house Retreat!
Children's area
Hickory on Willow Lake
Hickory on Willow Lake
9.6 out of 10, Exceptional, (4)
"Cute cottage on nice grounds with a small lake. Kayaks and life jackets available for use was a big plus"
United States
Rachel C.
The price is ￥64,672
￥92,883 total
includes taxes & fees
Oct 30 - Oct 31
Hickory on Willow Lake
Terrace/patio
Ultimate Lakeside Getaway on 5 Acres - Private Dock, Kayaks, Fire Pit - Sleeps 9
Ultimate Lakeside Getaway on 5 Acres - Private Dock, Kayaks, Fire Pit - Sleeps 9
9.8 out of 10, Exceptional, (19)
"Great host, amazing area, perfect get away!"
United States
Gianna W.
Ultimate Lakeside Getaway on 5 Acres - Private Dock, Kayaks, Fire Pit - Sleeps 9
Terrace/patio
Hot Tub - Fire Pit - BBQ - Hammock - Colonial
Hot Tub - Fire Pit - BBQ - Hammock - Colonial
9.6 out of 10, Exceptional, (21)
"This was a great stay away, just for a couple of quiet days. Inside the house was excellent. "
United States
Dennis M.
The price is ￥15,065
￥37,665 total
includes taxes & fees
Nov 5 - Nov 6
Hot Tub - Fire Pit - BBQ - Hammock - Colonial
Exterior
The Studio at the Inn at High Falls
The Studio at the Inn at High Falls
8.2 out of 10, Very Good, (31)
"Place is exactly how it looks! Great location between New Paltz, Kingston, Woodstock. We unfortunately had inconsiderate neighbors that forced us leave early, but Frank was incredibly gracious and made it up to us. Would stay again. "
United States
Harrison W.
The price is ￥17,119
￥41,329 total
includes taxes & fees
Oct 30 - Oct 31
The Studio at the Inn at High Falls
Outdoor pool
NEW Spectacular Views & Private space on a Scenic Mountain 40ft Salt Water Pool
NEW Spectacular Views & Private space on a Scenic Mountain 40ft Salt Water Pool
10.0 out of 10, Exceptional, (132)
"Great for a quiet weekend update. New Paltz and Stone Ridge are both close by and have great little main streets. House was very nice and accommodated our group well "
United States
Alex S.
NEW Spectacular Views & Private space on a Scenic Mountain 40ft Salt Water Pool
Exterior
Rustic Cabin in Fishkill!
Rustic Cabin in Fishkill!
10.0 out of 10, Exceptional, (2)
"The place was very nice, we met the owner and he was also bery accommodating. This is definitely a family friendly spot. "
United States
Arron T.
The price is ￥41,847
￥63,478 total
includes taxes & fees
Oct 30 - Oct 31
Rustic Cabin in Fishkill!
Terrace/patio
Dog-Friendly Hudson Valley Escape with Hot Tub & Jacuzzi
Dog-Friendly Hudson Valley Escape with Hot Tub & Jacuzzi
9.6 out of 10, Exceptional, (25)
"A lovely place and Seth is always so helpful."
United States
Lynn L.
The price is ￥13,695
￥36,301 total
includes taxes & fees
Oct 30 - Oct 31
Dog-Friendly Hudson Valley Escape with Hot Tub & Jacuzzi
Fridge, microwave, oven, stovetop
Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.
Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.
10.0 out of 10, Exceptional, (92)
"My family and I loved this property! We enjoyed walking around the woods and exploring. The house was well equipped and was really charming. We also loved sightseeing around the near by towns. Definitely a place to come back to stay again. "
United States
Hector L.
Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.
Smart TV, books
Be in Nature at this Gorgeous Riverfront Cabin
Be in Nature at this Gorgeous Riverfront Cabin
10.0 out of 10, Exceptional, (21)
"We had a wonderful stay. The Cabin is ideally situated in a very tranquil spot. Perfectly appointed, we couldn't have been happier with our stay."
United States
Phoebe J.
Be in Nature at this Gorgeous Riverfront Cabin
Exterior
Spacious A-Frame w/ Game Room, Fire Pit & Modern Comforts in Hudson Valley
Spacious A-Frame w/ Game Room, Fire Pit & Modern Comforts in Hudson Valley
10.0 out of 10, Exceptional, (8)
"Absolutely stunning A-frame! Super spacious, very clean/tidy, lots of room to hang inside, downstairs or have a fire outdoors. Beautiful area not far from New Paltz. We had such a fantastic time and would recommend this place to any group staying in the area! "
United States
Danielle O.
The price is ￥78,748
￥149,382 total
includes taxes & fees
Nov 10 - Nov 11
Spacious A-Frame w/ Game Room, Fire Pit & Modern Comforts in Hudson Valley
Outdoor dining
Cabin in the heart of the Hudson Valley, Cabin 4
Cabin in the heart of the Hudson Valley, Cabin 4
9.2 out of 10, Wonderful, (25)
"Enjoyable "
United States
Lisa M.
The price is ￥16,587
￥26,784 total
includes taxes & fees
Nov 4 - Nov 5
Cabin in the heart of the Hudson Valley, Cabin 4
Private kitchen
Charming 2-bedroom house in fabulous Kingston close to everything
Charming 2-bedroom house in fabulous Kingston close to everything
10.0 out of 10, Exceptional, (1)
"House was spotless. Hosts were very responsive and helpful. "
United States
Lawrence R.
Charming 2-bedroom house in fabulous Kingston close to everything
Outdoor dining
Cozy Lakefront Home - 278 FIVE STAR Reviews - Kayaks, Sunsets & Panoramic Views
Cozy Lakefront Home - 278 FIVE STAR Reviews - Kayaks, Sunsets & Panoramic Views
10.0 out of 10, Exceptional, (311)
"Excellent communication with great host. Pleasant, peaceful stay."
United States
Frank D.
Cozy Lakefront Home - 278 FIVE STAR Reviews - Kayaks, Sunsets & Panoramic Views
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.
View all properties
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

Americas Best Value Inn New Paltz

Americas Best Value Inn New Paltz

10/10 Excellent
"Hotel was clean perfect for Over night stay"
Nick 1-night trip
Posted 2 days ago
Americas Best Value Inn New Paltz

Find out more about Pleasant Valley

Search for holiday rentals in Pleasant Valley on Expedia! You can easily find your home rentals, villas, holiday apartments in Pleasant Valley using one of the methods below:

  • View our selection of featured holiday rentals in Pleasant Valley
  • Use the map to find apartments and other holiday homes in the Pleasant Valley neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Pleasant Valley while they last

Look no further and take a look at our great range of rental properties in Pleasant Valley!

Frequently asked questions

Are there vacation rentals in Pleasant Valley?

Yes, there are vacation rentals in Pleasant Valley close to Innisfree Garden, or you can go with a more secluded option if you'd like a relaxing place to 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's the top vacation rental that Pleasant Valley has to offer?

Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo: This vacation home rental near Pleasant Valley offers a fireplace, a patio, and air-conditioning to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms as well as a kitchen with an oven, a microwave, and kitchenware, so you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games.

How many vacation rentals are there in Pleasant Valley?

Choose from 8 Expedia vacation rentals in Pleasant Valley for a memorable vacation.

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 larger area, you’ll find James Baird State Park and Eleanor Roosevelt National Historic Site.

What are vacation rentals like in Pleasant Valley?

Vacation rentals are private properties you can book for several days or more in Pleasant Valley. Vacation rentals provide amenities such as hot tubs, fire pits, and patios so you'll feel just like you're at home. If you're concerned about cleanliness, vacation rentals can offer a sense of privacy away from shared hotel elevators and busy lobbies while still allowing you a great travel experience. You'll also get more space in a vacation rental than in a standard hotel, which makes a vacation rental an attractive choice for family trips.