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Pleasant Valley Holiday Rentals

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Check prices for these dates

In two weeks
25 Sept - 27 Sept
In two months
6 Nov - 8 Nov
In three months
4 Dec - 6 Dec
In four months
1 Jan - 3 Jan

Our top choices for Pleasant Valley holiday 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, (8 reviews)
"Great location not too far from the CIA."
United States
alexandra a.
The price is AU$311
includes taxes & fees
8 Sept - 9 Sept
Hudson Valley Farm Getaway- West/Llama Lover Lane
A deck with a red umbrella, wooden chairs, and a table with potted plants.

2. Mid-Century DJ’s Dream

Mid-Century DJ’s Dream
Staatsburg
10.0 out of 10, Exceptional, (58 reviews)
"Quiet clean accommodations in a central location for exploring the Hudson Valley."
United States
Alexandra R.
The price is AU$362
includes taxes & fees
13 Sept - 14 Sept
Mid-Century DJ’s Dream
A modern living room with a sectional sofa, a coffee table, and a bar area with stools.

3. Private, Cozy, Clean apartment in lovely Hyde Park

Private, Cozy, Clean apartment in lovely Hyde Park
Hyde Park
10.0 out of 10, Exceptional, (2 reviews)
"The host was great, the place was really nice and cozy. I would definitely stay here again!!! "
United States
Janet M.
The price is AU$303
includes taxes & fees
15 Sept - 16 Sept
Private, Cozy, Clean apartment in lovely Hyde Park
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
9.8 out of 10, Exceptional, (7 reviews)
"Nice stay for our quick overnight Comfortable space "
United States
jay c.
The price is AU$290
includes taxes & fees
16 Sept - 17 Sept
Pleasant 1-bedroom apartment in Staatsburg perfect for your getaway,
A modern kitchen with a granite countertop, a built-in stove, and a dining area with a glass table and chairs.

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

Stunning 5-bedroom house with AC / Heat in charming Poughkeepsie NY
Poughkeepsie
9.6 out of 10, Exceptional, (5 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 AU$675
includes taxes & fees
8 Sept - 9 Sept
Stunning 5-bedroom house with AC / Heat in charming Poughkeepsie NY
Two camping tents set up in a forest with chairs and a wooden platform nearby.

6. Rare, peaceful glamping, hot shower, mini golf near appalachian trail

Rare, peaceful glamping, hot shower, mini golf near appalachian trail
Dover Plains
10.0 out of 10, Exceptional, (11 reviews)
"We thoroughly enjoyed our stay at this property, clean and spacious tents, impressive shower facility, and all the fun amenities you never thought you needed like an 18 hole putt putt course!"
United States
JoAnna S.
Rare, peaceful glamping, hot shower, mini golf near appalachian trail
A covered outdoor area with a wooden deck and a view of a grassy landscape with trees and a distant white building.

7. Hoppy Hill Farm House

Hoppy Hill Farm House
Dover Plains
9.8 out of 10, Exceptional, (6 reviews)
"The accommodations were wonderful and comfortable."
United States
Chuck S.
The price is AU$287
includes taxes & fees
13 Sept - 14 Sept
Hoppy Hill Farm House
A white house with a steeply pitched roof and a small tower-like structure.

8. 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, (6 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 AU$670
includes taxes & fees
9 Sept - 10 Sept
Charming 2-bedroom apartment on 2nd floor in Millbrook NY, right in the village
A farm sign for Clover Brooke Farm in Hyde Park, NY, with a barn and a building in the background.

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

Hudson Valley Farm Getaway-East/Alpaca Lane-Apt 1
Hyde Park
8.0 out of 10, Very good, (3 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 AU$311
includes taxes & fees
8 Sept - 9 Sept
Hudson Valley Farm Getaway-East/Alpaca Lane-Apt 1
A small, two-story house with a red and gray exterior, a front porch with blue chairs, and a table.

10. 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, (28 reviews)
"Pet-friendly and easily accessible."
United States
Brigitte
The price is AU$320
includes taxes & fees
8 Sept - 9 Sept
Cabin in the heart of the Hudson Valley, Cabin 4
A modern kitchen with white cabinets, a built-in toaster, a blender, and a window with a view of trees.

11. Amazing 3-bedroom house with AC in adorable Highland

Amazing 3-bedroom house with AC in adorable Highland
Highland
The price is AU$739
includes taxes & fees
9 Sept - 10 Sept
Amazing 3-bedroom house with AC in adorable Highland
A spacious living room with a large wooden dining table, a comfortable sofa, and a bookshelf filled with books and decorative items.

12. 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, (6 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 AU$1,137
includes taxes & fees
13 Sept - 14 Sept
Steps to the Delightful Village of Millbrook ☆ Fun Family Getaway
A porch with white railings and multiple chairs.

13. 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 AU$532
includes taxes & fees
8 Sept - 9 Sept
Step into history & unwind at Spring apt a charming 🏡 at the❤️of NYHudson Valley
A neatly made bed with a white pillow, a red pillow, and a white blanket. There is a small bedside table with a lamp.

14. Hibiscus Suite - Private Studio Apartment in Rhinebeck Village

Hibiscus Suite - Private Studio Apartment in Rhinebeck Village
Rhinebeck Village
10.0 out of 10, Exceptional, (32 reviews)
"great place for homebase to visit Hudson Valley area and host was very communicative and helpful"
United States
Brian C.
The price is AU$444
includes taxes & fees
8 Sept - 9 Sept
Hibiscus Suite - Private Studio Apartment in Rhinebeck Village
A brick building with a sign reading 'Lobby' in front.

15. 1 Queen Bed | Non-Smoking, Kitchen

1 Queen Bed | Non-Smoking, Kitchen
Fishkill
10.0 out of 10, Exceptional, (17 reviews)
"Nice place to stay"
United States
Anonymous traveller
The price is AU$131
includes taxes & fees
30 Sept - 1 Oct
1 Queen Bed | Non-Smoking, Kitchen
A living room with a fireplace, two armchairs, a sofa, and a TV.

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

Mid Century Modern Studio w/ Full Kitchen - Newly Built
Kent
10.0 out of 10, Exceptional, (24 reviews)
"Clean, quiet, well stocked studio with everything we needed for our weekend in Kent. Very convenient to town. Highly recommend!"
United States
Joy P.
The price is AU$298
includes taxes & fees
8 Sept - 9 Sept
Mid Century Modern Studio w/ Full Kitchen - Newly Built
A compact living space with a kitchenette, a sofa, a bed, and a colorful rug.

17. 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 AU$391
includes taxes & fees
8 Sept - 9 Sept
Cabin in the Heart of the Hudson Valley, Cabin 1
A living room with a fireplace, a painting, shelves with decorative items, and a television.

18. Grant - A Tranquil One Bedroom Steps from River

Grant - A Tranquil One Bedroom Steps from River
Newburgh
9.6 out of 10, Exceptional, (48 reviews)
"We enjoyed our stay, property was as described. It's convenient to many of the Hudson Valley small towns, including West Point."
United States
Mike W.
The price is AU$412
includes taxes & fees
14 Sept - 15 Sept
Grant - A Tranquil One Bedroom Steps from River
A spacious living area with a staircase, a dining table, and a sofa.

19. 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 AU$1,006
includes taxes & fees
8 Sept - 9 Sept
Our home is perfect for relaxing and having lots of fun, with near by activity’s

20. 2 Queen Beds | Non-Smoking, Kitchen

2 Queen Beds | Non-Smoking, Kitchen
Fishkill
8.6 out of 10, Excellent, (24 reviews)
"Worst hotel experience I have ever had. Grounds were unkept. No one was at the front desk when I first arrived. Waited 20 minutes for someone to arrive and had to leave for dinner. Came back to find out that they were overbooked."
United States
Glenn
The price is AU$129
includes taxes & fees
30 Sept - 1 Oct
2 Queen Beds | Non-Smoking, Kitchen
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

Hampton Inn & Suites Poughkeepsie

Hampton Inn & Suites Poughkeepsie

10/10 Excellent
"Clean room, pleasant area, safe parking, good breakfast."
Sanford 1-night trip
Posted 6 hours ago
Hampton Inn & Suites Poughkeepsie

Find out more about Pleasant Valley

Everything you need to know about Pleasant Valley holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Pleasant Valley holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Pleasant Valley holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Pleasant Valley holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Pleasant Valley. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Pleasant Valley holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Pleasant Valley holiday rentals we have selected for you start as low as AU$131 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Pleasant Valley rentals

At Expedia, we put the best Pleasant Valley holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Pleasant Valley rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Pleasant Valley holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Pleasant Valley. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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 Chicken Coop: This holiday home rental outside of Pleasant Valley is located in a rural location, and has a patio, a garden and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop.

How many holiday rentals are there in Pleasant Valley?

Choose from 7 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.