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Pleasant Valley Vacation Rentals

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Check prices for these dates

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

Our top choices for Pleasant Valley vacation rentals

A compact kitchen with white cabinets, a black refrigerator, and a microwave. There is a wooden dining table with a chair, and a sofa with a decorative pillow.

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 ￥27,303
￥33,745 total
includes taxes & fees
Nov 9 - Nov 10
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 ￥18,114
￥31,788 total
includes taxes & fees
Nov 10 - Nov 11
Pleasant 1-bedroom apartment in Staatsburg perfect for your getaway,
A room with a large bookshelf filled with books and DVDs, a bed, a small table with a lamp, and a window with blinds.

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 ￥22,187
￥36,035 total
includes taxes & fees
Nov 11 - Nov 12
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 ￥34,081
￥76,298 total
includes taxes & fees
Nov 9 - Nov 10
Stunning 5-bedroom house with AC / Heat in charming Poughkeepsie NY
Terrace/patio

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 ￥27,303
￥33,745 total
includes taxes & fees
Nov 9 - Nov 10
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 ￥50,714
￥71,534 total
includes taxes & fees
Nov 9 - Nov 10
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 ￥63,392
￥120,657 total
includes taxes & fees
Nov 15 - Nov 16
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 ￥12,454
￥14,400 total
includes taxes & fees
Nov 25 - Nov 26
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 ￥16,403
￥39,352 total
includes taxes & fees
Nov 10 - Nov 11
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 ￥35,658
￥105,789 total
includes taxes & fees
Nov 9 - Nov 10
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 ￥33,677
￥67,715 total
includes taxes & fees
Nov 9 - Nov 10
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 ￥11,207
￥12,678 total
includes taxes & fees
Nov 22 - Nov 23
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 ￥34,866
￥69,224 total
includes taxes & fees
Nov 9 - Nov 10
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 ￥23,574
￥29,011 total
includes taxes & fees
Nov 9 - Nov 10
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 ￥11,886
￥38,694 total
includes taxes & fees
Nov 10 - Nov 11
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 ￥23,614
￥35,570 total
includes taxes & fees
Nov 9 - Nov 10
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 ￥11,886
￥36,742 total
includes taxes & fees
Nov 18 - Nov 19
Campfire Cottage: Fireplace, fire pit & no chores!
A two-story house with a front porch and a landscaped garden.

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 ￥11,411
￥21,123 total
includes taxes & fees
Nov 9 - Nov 10
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 ￥15,690
￥32,318 total
includes taxes & fees
Nov 9 - Nov 10
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 ￥26,783
￥43,620 total
includes taxes & fees
Nov 9 - Nov 10
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.
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Top Pleasant Valley Hotel Reviews

Residence Inn by Marriott Kingston

Residence Inn by Marriott Kingston

10/10 Excellent
"It is close to everything and a well maintained property."
Wendy 2-night trip
Posted 2 hours ago
Residence Inn by Marriott Kingston

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.