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Pleasant Valley Vacation Rentals

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Check prices for these dates

In two weeks
Nov 6 - Nov 8
In two months
Dec 18 - Dec 20
In three months
Jan 15 - Jan 17
In four months
Feb 12 - Feb 14

Our top choices for Pleasant Valley vacation rentals

A modern kitchen with a granite countertop, a built-in stove, and a dining area with a glass table and chairs.

1. Stunning 5-bedroom house with AC / Heat in charming Poughkeepsie NY

Stunning 5-bedroom house with AC / Heat in charming Poughkeepsie NY
Poughkeepsie
9.8 out of 10, Exceptional, (6 reviews)
"Beautiful property with ample space for parking. Host was super nice and met all of our needs!"
United States
Nicole Y.
The price is ￥25,428
￥68,159 total
includes taxes & fees
Oct 22 - Oct 23
Stunning 5-bedroom house with AC / Heat in charming Poughkeepsie NY
A farm sign for Clover Brooke Farm in Hyde Park, NY, with a barn and a building in the background.

2. Hudson Valley Farm Getaway- West/Llama Lover Lane

Hudson Valley Farm Getaway- West/Llama Lover Lane
Hyde Park
9.8 out of 10, Exceptional, (9 reviews)
"Great location not too far from the CIA."
United States
alexandra a.
The price is ￥28,704
￥37,223 total
includes taxes & fees
Oct 25 - Oct 26
Hudson Valley Farm Getaway- West/Llama Lover Lane
A deck with a red umbrella, wooden chairs, and a table with potted plants.

3. Mid-Century DJ’s Dream

Mid-Century DJ’s Dream
Staatsburg
10.0 out of 10, Exceptional, (61 reviews)
"Quiet clean accommodations in a central location for exploring the Hudson Valley."
United States
Alexandra R.
The price is ￥24,692
￥41,004 total
includes taxes & fees
Oct 26 - Oct 27
Mid-Century DJ’s Dream
A modern kitchen with white cabinets, a central island, and a view to the outside.

4. Pleasant 1-bedroom apartment in Staatsburg perfect for your getaway,

Pleasant 1-bedroom apartment in Staatsburg perfect for your getaway,
Staatsburg
9.6 out of 10, Exceptional, (12 reviews)
"We thoroughly enjoyed our stay. We would definitely come back! A fantastic location. And very good communication with the host, Alexander."
United States
elizabeth
The price is ￥17,807
￥32,858 total
includes taxes & fees
Nov 2 - Nov 3
Pleasant 1-bedroom apartment in Staatsburg perfect for your getaway,
A white house with a steeply pitched roof and a small tower-like structure.

5. Charming 2-bedroom apartment on 2nd floor in Millbrook NY, right in the village

Charming 2-bedroom apartment on 2nd floor in Millbrook NY, right in the village
Millbrook
9.8 out of 10, Exceptional, (8 reviews)
"We had a wonderful time at this property. It was quaint and clean and right in the middle of town near everything. Thank you, Tanya."
United States
Laurie F.
The price is ￥50,650
￥78,248 total
includes taxes & fees
Oct 25 - Oct 26
Charming 2-bedroom apartment on 2nd floor in Millbrook NY, right in the village
A spacious living room with a large wooden dining table, a comfortable sofa, and a bookshelf filled with books and decorative items.

6. Steps to the Delightful Village of Millbrook ☆ Fun Family Getaway

Steps to the Delightful Village of Millbrook ☆ Fun Family Getaway
Millbrook
10.0 out of 10, Exceptional, (7 reviews)
"This is a charming, historic, well-maintained home on a beautifully landscaped lot. The updates in the home balance a respect for tradition while also providing modernization. The village of Millbrook is a quintessential twee New England village. The house felt very comfortable and homey and the caretaker was attentive and accommodating. We enjoyed our stay!"
United States
Beth E.
The price is ￥63,312
￥131,607 total
includes taxes & fees
Oct 26 - Oct 27
Steps to the Delightful Village of Millbrook ☆ Fun Family Getaway
A farm sign for Clover Brooke Farm in Hyde Park, NY, with a barn and a building in the background.

7. Hudson Valley Farm Getaway-East/Alpaca Lane-Apt 1

Hudson Valley Farm Getaway-East/Alpaca Lane-Apt 1
Hyde Park
8.6 out of 10, Excellent, (4 reviews)
"Great spot if you’re looking for a quiet rural area ! Seeing the llamas made the stay more fun. We weren’t there when the store was open so it was a bit disappointing we couldn’t see more of what the farm offers. We’d definitely go again."
United States
Meg H.
The price is ￥28,704
￥37,403 total
includes taxes & fees
Oct 27 - Oct 28
Hudson Valley Farm Getaway-East/Alpaca Lane-Apt 1
A wooden porch with white rocking chairs and a hanging flower basket.

8. Step into history & unwind at Elixir apt a charming 🏡 at the❤️of NYHudson Valley

Step into history & unwind at Elixir apt a charming 🏡 at the❤️of NYHudson Valley
Highland
9.6 out of 10, Exceptional, (11 reviews)
"Would definitely stay again"
United States
Laurie G.
The price is ￥26,908
￥62,578 total
includes taxes & fees
Oct 22 - Oct 23
Step into history & unwind at Elixir apt a charming 🏡 at the❤️of NYHudson Valley
A porch with white railings and multiple chairs.

9. Step into history & unwind at Spring apt a charming 🏡 at the❤️of NYHudson Valley

Step into history & unwind at Spring apt a charming 🏡 at the❤️of NYHudson Valley
Highland
10.0 out of 10, Exceptional, (2 reviews)
"Everyone was just right! The home is perfect for a photo shoot. We weren't there for that, but we thought the setting was unique and beautiful! Everything we needed!!"
United States
Rebecca D.
The price is ￥31,656
￥68,605 total
includes taxes & fees
Oct 22 - Oct 23
Step into history & unwind at Spring apt a charming 🏡 at the❤️of NYHudson Valley
A spacious living area with a staircase, a dining table, and a sofa.

10. Our home is perfect for relaxing and having lots of fun, with near by activity’s

Our home is perfect for relaxing and having lots of fun, with near by activity’s
Highland
9.6 out of 10, Exceptional, (13 reviews)
"We had was great time and the host Mary was amazing and excellent at communicating. Everything was perfect in the home. Thank you"
United States
Pinal
The price is ￥35,613
￥111,151 total
includes taxes & fees
Oct 27 - Oct 28
Our home is perfect for relaxing and having lots of fun, with near by activity’s
A neatly made bed with a white pillow, a red pillow, and a white blanket. There is a small bedside table with a lamp.

11. Hibiscus Suite - Private Studio Apartment in Rhinebeck Village

Hibiscus Suite - Private Studio Apartment in Rhinebeck Village
Rhinebeck Village
10.0 out of 10, Exceptional, (33 reviews)
"Beautiful place has a great stay!"
United States
Heather O.
The price is ￥19,468
￥45,659 total
includes taxes & fees
Nov 17 - Nov 18
Hibiscus Suite - Private Studio Apartment in Rhinebeck Village
A brick building with a sign reading 'Lobby' in front.

12. Cozy Queen Suite, Nsmk Kitchen|Studio 6 Fishkill

Cozy Queen Suite, Nsmk Kitchen|Studio 6 Fishkill
Fishkill
9.0 out of 10, Wonderful, (21 reviews)
"Great place to stay,"
United States
Anonymous traveler
The price is ￥12,533
￥14,492 total
includes taxes & fees
Nov 1 - Nov 2
Cozy Queen Suite, Nsmk Kitchen|Studio 6 Fishkill
A hotel lobby with a reception desk, seating area, and a fire extinguisher on the wall.

13. 1 King Bed | Non-Smoking, Kitchen, Shower

1 King Bed | Non-Smoking, Kitchen, Shower
Fishkill
9.6 out of 10, Exceptional, (19 reviews)
"Great rooms and service,"
United States
Anonymous traveler
The price is ￥12,533
￥14,177 total
includes taxes & fees
Oct 25 - Oct 26
1 King Bed | Non-Smoking, Kitchen, Shower
A compact living space with a kitchenette, a sofa, a bed, and a colorful rug.

14. Cabin in the Heart of the Hudson Valley, Cabin 1

Cabin in the Heart of the Hudson Valley, Cabin 1
Newburgh
10.0 out of 10, Exceptional, (36 reviews)
"Great place! Nicely decorated with attention to detail. My wife and I would stay again if we are back in the area."
United States
Tim G.
The price is ￥19,785
￥36,458 total
includes taxes & fees
Oct 22 - Oct 23
Cabin in the Heart of the Hudson Valley, Cabin 1
An outdoor patio area with a covered seating area, a pool, and potted plants.

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

Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
Fishkill
9.2 out of 10, Wonderful, (81 reviews)
"The property was as advertised and met our needs for our trip."
United States
Sara
The price is ￥41,351
￥54,218 total
includes taxes & fees
Oct 28 - Oct 29
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
A staircase leading to a second floor, a sofa with a throw blanket, a floor lamp, a small table with a vase of sunflowers, and a kitchen area visible through an archway.

16. Chilly Days Hiking, Quiet Yard, an Easy Escape Near New Paltz

Chilly Days Hiking, Quiet Yard, an Easy Escape Near New Paltz
New Paltz
10.0 out of 10, Exceptional, (8 reviews)
"Superb property - comfortable, spotless, all the amenities you could need, and lots of space. "
United States
Thomas B.
Chilly Days Hiking, Quiet Yard, an Easy Escape Near New Paltz
A large wooden dining table surrounded by chairs, with a stone fireplace and large windows in the background.

17. The George is an elegant restored home in the Hudson Valley

The George is an elegant restored home in the Hudson Valley
Stanfordville
9.8 out of 10, Exceptional, (12 reviews)
"Clean, comfortable, private, and plenty of room. Hosts went above and beyond to make our stay easy and memorable."
United States
Polly J.
The price is ￥113,962
￥175,474 total
includes taxes & fees
Oct 22 - Oct 23
The George is an elegant restored home in the Hudson Valley
A wooden gate leading to a driveway with a stone pathway, surrounded by greenery and a house in the background.

18. Maple Ridge Modern Rustic Retreat where Modern comfort meets Rustic Charm

Maple Ridge Modern Rustic Retreat where Modern comfort meets Rustic Charm
Ulster Park
9.8 out of 10, Exceptional, (20 reviews)
"Easy access and checkout, extremely clean, accurate pictures, comfy beds, well stocked kitchen. Great for groups. Would gladly stay again!"
United States
Emily F.
The price is ￥46,001
￥129,701 total
includes taxes & fees
Nov 1 - Nov 2
Maple Ridge Modern Rustic Retreat where Modern comfort meets Rustic Charm
A small blue house with two blue Adirondack chairs, a small table, and a potted plant.

19. Cabin in the heart of the Hudson Valley, Cabin 2

Cabin in the heart of the Hudson Valley, Cabin 2
Newburgh
9.6 out of 10, Exceptional, (41 reviews)
"This was a great place to stay with our cats for a night on our way to Vermont."
United States
George J.
The price is ￥23,584
￥37,207 total
includes taxes & fees
Oct 25 - Oct 26
Cabin in the heart of the Hudson Valley, Cabin 2
A spacious loft with a high ceiling, exposed wooden beams, a staircase, a flat-screen TV, and a round wooden coffee table with a plant.

20. Stunning and Cozy loft apartment in kingston .

Stunning and Cozy loft apartment in kingston .
Kingston
9.4 out of 10, Exceptional, (18 reviews)
"Very cute place, clean and comfortable. "
United States
Robin H.
The price is ￥23,742
￥42,368 total
includes taxes & fees
Oct 22 - Oct 23
Stunning and Cozy loft apartment in kingston .
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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Top Pleasant Valley Hotel Reviews

Hyatt Place Poughkeepsie / Hudson Valley

Hyatt Place Poughkeepsie / Hudson Valley

10/10 Excellent
"wonderful stay, exactly what we needed"
James 2-night trip
Posted less than an hour ago
Hyatt Place Poughkeepsie / Hudson Valley

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?

Lakehouse Boat Dock, Kayaks, Fire-Pit, Pool Table, Air Hockey, Hammock, King Bed: This vacation home near Pleasant Valley offers a fireplace, a patio, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, 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 7 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.