A row of houses with a mountain in the background.

Pleasant Valley Vacation Rentals

  • 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

In two weeks
20 Nov - 22 Nov
In two months
1 Jan - 3 Jan
In three months
29 Jan - 31 Jan
In four months
26 Feb - 28 Feb

Our top choices for Pleasant Valley vacation rentals

A farm sign for Clover Brooke Farm in Hyde Park, NY, with a barn and a building in the background.

1. 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 AED 633
AED 782 total
includes taxes & fees
9 Nov - 10 Nov
Hudson Valley Farm Getaway- West/Llama Lover Lane
A modern kitchen with white cabinets, a central island, and a view to the outside.

2. 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, (13 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 AED 420
AED 737 total
includes taxes & fees
10 Nov - 11 Nov
Pleasant 1-bedroom apartment in Staatsburg perfect for your getaway,
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 AED 650
AED 1,001 total
includes taxes & fees
18 Nov - 19 Nov
Mid-Century DJ’s Dream
A modern kitchen with a granite countertop, a built-in stove, and a dining area with a glass table and chairs.

4. 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 AED 1,359
AED 2,478 total
includes taxes & fees
8 Dec - 9 Dec
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.

5. 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 AED 633
AED 782 total
includes taxes & fees
8 Nov - 9 Nov
Hudson Valley Farm Getaway-East/Alpaca Lane-Apt 1
A white house with a steeply pitched roof and a small tower-like structure.

6. 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, (9 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 AED 1,175
AED 1,724 total
includes taxes & fees
8 Nov - 9 Nov
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.

7. 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, (8 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 AED 1,469
AED 2,796 total
includes taxes & fees
12 Nov - 13 Nov
Steps to the Delightful Village of Millbrook ☆ Fun Family Getaway
A brick building with a sign reading 'Lobby' in front.

8. 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 AED 289
AED 334 total
includes taxes & fees
24 Nov - 25 Nov
Cozy Queen Suite, Nsmk Kitchen|Studio 6 Fishkill
A neatly made bed with a white pillow, a red pillow, and a white blanket. There is a small bedside table with a lamp.

9. 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 AED 390
AED 923 total
includes taxes & fees
10 Nov - 11 Nov
Hibiscus Suite - Private Studio Apartment in Rhinebeck Village
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, (14 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 AED 826
AED 2,452 total
includes taxes & fees
8 Nov - 9 Nov
Our home is perfect for relaxing and having lots of fun, with near by activity’s
A porch with white railings and multiple chairs.

11. 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 AED 918
AED 1,662 total
includes taxes & fees
21 Nov - 22 Nov
Step into history & unwind at Spring apt a charming 🏡 at the❤️of NYHudson Valley
A hotel lobby with a reception desk, seating area, and a fire extinguisher on the wall.

12. 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 AED 260
AED 294 total
includes taxes & fees
7 Dec - 8 Dec
1 King Bed | Non-Smoking, Kitchen, Shower
A wooden porch with white rocking chairs and a hanging flower basket.

13. 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 AED 808
AED 1,596 total
includes taxes & fees
8 Nov - 9 Nov
Step into history & unwind at Elixir apt a charming 🏡 at the❤️of NYHudson Valley
A living room with a fireplace, two armchairs, a sofa, and a TV.

14. Mid Century Modern Studio w/ Full Kitchen - Newly Built

Mid Century Modern Studio w/ Full Kitchen - Newly Built
Kent
9.8 out of 10, Exceptional, (26 reviews)
"Very private, rural spot. Immaculate, thoughtfully furnished, lacking nothing"
United States
benjamin
The price is AED 546
AED 672 total
includes taxes & fees
9 Nov - 10 Nov
Mid Century Modern Studio w/ Full Kitchen - Newly Built
A compact kitchen with blue cabinets, a white stove, and yellow chairs.

15. Retro Retreat: 1br home w/ WFH desk, livingroom, fire pit and no chores!

Retro Retreat: 1br home w/ WFH desk, livingroom, fire pit and no chores!
Kingston
10.0 out of 10, Exceptional, (7 reviews)
"Beautiful house to stay in, convenient to numerous restaurants and hikes. Our host was very communicative and had great recommendations for the area!"
United States
Brendan B.
The price is AED 275
AED 897 total
includes taxes & fees
10 Nov - 11 Nov
Retro Retreat: 1br home w/ WFH desk, livingroom, fire pit and no chores!
A small, two-story house with a red and gray exterior, a front porch with blue chairs, and a table.

16. Cabin in the heart of the Hudson Valley, Cabin 4

Cabin in the heart of the Hudson Valley, Cabin 4
Newburgh
9.2 out of 10, Wonderful, (31 reviews)
"Everything was just as it was in our past stays. The place was clean, neat and organized very well. Communication with the host was very easy and almost immediate reply."
United States
Albert
The price is AED 547
AED 820 total
includes taxes & fees
8 Nov - 9 Nov
Cabin in the heart of the Hudson Valley, Cabin 4
A modern kitchen with a granite countertop, stainless steel appliances, and a built-in oven.

17. Campfire Cottage: Fireplace, fire pit & no chores!

Campfire Cottage: Fireplace, fire pit & no chores!
Kingston
10.0 out of 10, Exceptional, (33 reviews)
"Great multi-week stay! Would certainly stay again. "
United States
Jim R.
The price is AED 275
AED 852 total
includes taxes & fees
18 Nov - 19 Nov
Campfire Cottage: Fireplace, fire pit & no chores!
A rural landscape with a barn, a silo, and a bridge with rocks and purple flowers in the foreground.

18. A Cozy Private Suite in a Country Home near New Paltz

A Cozy Private Suite in a Country Home near New Paltz
Wallkill
9.2 out of 10, Wonderful, (20 reviews)
"The room was super cute and clean. It had everything that I needed."
United States
Carrie
The price is AED 264
AED 490 total
includes taxes & fees
8 Nov - 9 Nov
A Cozy Private Suite in a Country Home near New Paltz
A compact living space with a kitchenette, a sofa, a coffee table, and a patterned rug.

19. Charming & Quaint 1 bed in Historic Uptown!

Charming & Quaint 1 bed in Historic Uptown!
Kingston
The price is AED 364
AED 749 total
includes taxes & fees
9 Nov - 10 Nov
Charming & Quaint 1 bed in Historic Uptown!
A compact living space with a kitchenette, a sofa, a bed, and a colorful rug.

20. 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 AED 621
AED 1,007 total
includes taxes & fees
8 Nov - 9 Nov
Cabin in the Heart of the Hudson Valley, Cabin 1
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

Beekman Arms and Delamater Inn

Beekman Arms and Delamater Inn

10/10 Excellent
"great place to stay"
Julia 1-night trip
Posted 2 hours ago
Beekman Arms and Delamater Inn

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.