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Pleasant Valley Vacation Rentals

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Check prices for these dates

In two weeks
Aug 21 - Aug 23
In two months
Oct 2 - Oct 4
In three months
Oct 30 - Nov 1
In four months
Nov 27 - Nov 29

Our top choices for Pleasant Valley vacation rentals

Property grounds

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 ￥27,175
￥35,371 total
includes taxes & fees
Aug 6 - Aug 7
Hudson Valley Farm Getaway- West/Llama Lover Lane
Property grounds

2. Mid-Century DJ’s Dream

Mid-Century DJ’s Dream
Staatsburg
10.0 out of 10, Exceptional, (56 reviews)
"Quiet clean accommodations in a central location for exploring the Hudson Valley."
United States
Alexandra R.
The price is ￥22,588
￥37,509 total
includes taxes & fees
Aug 6 - Aug 7
Mid-Century DJ’s Dream
Coffee/tea maker, fridge, oven, stovetop

3. 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, (5 reviews)
"Nice stay for our quick overnight Comfortable space "
United States
jay c.
The price is ￥17,036
￥31,764 total
includes taxes & fees
Sep 2 - Sep 3
Pleasant 1-bedroom apartment in Staatsburg perfect for your getaway,
Property grounds

4. 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, (8 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.
The price is ￥12,635
￥21,076 total
includes taxes & fees
Aug 10 - Aug 11
Rare, peaceful glamping, hot shower, mini golf near appalachian trail
Smart TV, fireplace

5. 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 ￥27,447
￥40,328 total
includes taxes & fees
Aug 17 - Aug 18
Private, Cozy, Clean apartment in lovely Hyde Park
Property grounds

6. 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 ￥17,351
￥32,298 total
includes taxes & fees
Aug 10 - Aug 11
Hoppy Hill Farm House
Paper towels

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

Amazing 3-bedroom house with AC in adorable Highland
Highland
The price is ￥40,034
￥86,001 total
includes taxes & fees
Aug 11 - Aug 12
Amazing 3-bedroom house with AC in adorable Highland
Property grounds

8. 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 ￥28,606
￥36,739 total
includes taxes & fees
Aug 9 - Aug 10
Hudson Valley Farm Getaway-East/Alpaca Lane-Apt 1
Outdoor dining

9. 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 ￥20,339
￥31,663 total
includes taxes & fees
Aug 12 - Aug 13
Cabin in the heart of the Hudson Valley, Cabin 4
Interior

10. 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, (4 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 ￥56,179
￥108,662 total
includes taxes & fees
Aug 6 - Aug 7
Stunning 5-bedroom house with AC / Heat in charming Poughkeepsie NY
Coffee/tea maker, fridge, microwave, oven

11. 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, (6 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 ￥11,200
￥38,868 total
includes taxes & fees
Aug 10 - Aug 11
Retro Retreat: 1br home w/ WFH desk, livingroom, fire pit and no chores!
Interior

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

Campfire Cottage: Fireplace, fire pit & no chores!
Kingston
10.0 out of 10, Exceptional, (31 reviews)
"The place was amazing! Very easy check in/out process and the host is very responsive. "
United States
Samuel M.
The price is ￥17,351
￥47,170 total
includes taxes & fees
Aug 19 - Aug 20
Campfire Cottage: Fireplace, fire pit & no chores!
1 bedroom, WiFi (free)

13. 2 Queen Beds | Non-Smoking, Kitchen

2 Queen Beds | Non-Smoking, Kitchen
Fishkill
9.8 out of 10, Exceptional, (20 reviews)
"Schöne Zimmer, Internet war kostenpflichtig, funktionierte aber nicht. Das Personal war jedoch nett."
Germany
Anonymous traveler
The price is ￥15,838
￥17,915 total
includes taxes & fees
Sep 1 - Sep 2
2 Queen Beds | Non-Smoking, Kitchen
Terrace/patio

14. Dog-Friendly Hudson Valley Escape with Hot Tub & Jacuzzi

Dog-Friendly Hudson Valley Escape with Hot Tub & Jacuzzi
Kingston
9.4 out of 10, Exceptional, (33 reviews)
"The beds were especially comfortable! "
United States
josh p.
The price is ￥19,165
￥43,902 total
includes taxes & fees
Aug 10 - Aug 11
Dog-Friendly Hudson Valley Escape with Hot Tub & Jacuzzi
Exterior

15. 2 Full Beds | Non-Smoking, Kitchen

2 Full Beds | Non-Smoking, Kitchen
Fishkill
9.4 out of 10, Exceptional, (20 reviews)
"great place tostay"
United States
Anonymous traveler
The price is ￥13,462
￥15,565 total
includes taxes & fees
Aug 30 - Aug 31
2 Full Beds | Non-Smoking, Kitchen
Exterior

16. 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
9.6 out of 10, Exceptional, (4 reviews)
"Lovely home in the heart of Millbrook."
United States
Marianne A S.
The price is ￥50,477
￥77,444 total
includes taxes & fees
Aug 6 - Aug 7
Charming 2-bedroom apartment on 2nd floor in Millbrook NY, right in the village
Terrace/patio

17. Hudson Valley Apartment in a Historic Farmhouse w/ Sauna Near Stone Ridge Hamlet

Hudson Valley Apartment in a Historic Farmhouse w/ Sauna Near Stone Ridge Hamlet
Stone Ridge
8.6 out of 10, Excellent, (17 reviews)
"Clean cozy will be staying again"
United States
Michael C.
The price is ￥12,272
￥24,481 total
includes taxes & fees
Aug 9 - Aug 10
Hudson Valley Apartment in a Historic Farmhouse w/ Sauna Near Stone Ridge Hamlet
1 bedroom, WiFi (free), bed sheets

18. The Studio at the Inn at High Falls

The Studio at the Inn at High Falls
High Falls
8.0 out of 10, Very Good, (41 reviews)
"I had a great stay here, it’s just as listed; simple but has everything that I needed, check in was easy, communication was good, and bed was comfortable!"
United States
Jamie M.
The price is ￥17,746
￥42,312 total
includes taxes & fees
Aug 9 - Aug 10
The Studio at the Inn at High Falls
1 bedroom, iron/ironing board, WiFi (free), bed sheets

19. 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 overnight spot, especially with a dog."
United States
Ed C.
The price is ￥26,646
￥44,327 total
includes taxes & fees
Aug 12 - Aug 13
Cabin in the Heart of the Hudson Valley, Cabin 1
Outdoor dining

20. Glamping, family fun, pet friendly

Glamping, family fun, pet friendly
Dover Plains
10.0 out of 10, Exceptional, (4 reviews)
"Great Glamping spot. The hosts were very responsive and the place provided many activities. "
United States
Gui
The price is ￥12,635
￥21,076 total
includes taxes & fees
Aug 10 - Aug 11
Glamping, family fun, pet friendly
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 by Hilton New Paltz

Hampton Inn by Hilton New Paltz

10/10 Excellent
"It was our first time in New York and the staff was so very helpful and friendly. A great stay!"
Audrey 2-night trip
Posted less than an hour ago
Hampton Inn by Hilton 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
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  • 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?

The Studio at the Inn at High Falls: This vacation home near Pleasant Valley is located in a rural location and offers a garden, air-conditioning, and a Smart TV to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a microwave, and a coffee maker.

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.