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Pleasant Valley Vacation Rentals

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Check prices for these dates

Next weekend
Aug 15 - Aug 17
In two weeks
Aug 22 - Aug 24
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Sep 5 - Sep 7
In two months
Oct 3 - Oct 5

Browse Select Pleasant Valley Vacation Homes

The Farm at Hyde Park
Set amidst lush greenery and mature trees, this charming building features a steeply pitched roof and a brick facade.

The Farm at Hyde Park

9.8 out of 10, Exceptional, (75)
"We were visiting the Culinary Institute highly recommend it."
The Farm at Hyde Park
Cozy Lakefront Home - 278 FIVE STAR Reviews - Kayaks, Sunsets & Panoramic Views
Relax on the serene deck, surrounded by bare trees and a frozen lake.

Cozy Lakefront Home - 278 FIVE STAR Reviews - Kayaks, Sunsets & Panoramic Views

10.0 out of 10, Exceptional, (301)
"The lake views at this house are absolutely worth the trip and the money. It's a beautiful spot. And the host, Don, is super responsive, thoughtful and accommodating. Highly recommend!"
The price is CA $618
CA $818 total
includes taxes & fees
Aug 24 - Aug 25
Cozy Lakefront Home - 278 FIVE STAR Reviews - Kayaks, Sunsets & Panoramic Views
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
Relax in this serene outdoor seating area with a covered patio overlooking a lush garden.

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

9.8 out of 10, Exceptional, (27)
"Perfect for small family stay over for a wedding ! "
The price is CA $356
CA $461 total
includes taxes & fees
Aug 31 - Sep 1
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.
Enjoy cooking in this well-equipped kitchen with a central island, stainless steel stove, and ample counter space.

Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.

10.0 out of 10, Exceptional, (86)
"We loved our stay. It was great for a family Thanksgiving"
Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.
Esopus Creek modern Tiny house Retreat!
Enjoy a romantic dinner for two on this deck with a beautiful floral arrangement and a bottle of wine.

Esopus Creek modern Tiny house Retreat!

9.6 out of 10, Exceptional, (45)
"4 of us stayed for a fishing trip and had a blast. Nice place at a reasonable price. Would stay again. "
The price is CA $204
CA $332 total
includes taxes & fees
Aug 17 - Aug 18
Esopus Creek modern Tiny house Retreat!
Scenic New Paltz Escape: River Views, Hot Tub & Deck | Dream House in the Gunks
Enjoy cooking in this well-equipped kitchen with a large island, oven, and stainless steel range hood.

Scenic New Paltz Escape: River Views, Hot Tub & Deck | Dream House in the Gunks

2.0 star property
9.8 out of 10, Exceptional, (12)
"A group of girlfriends stayed for a 2 night visit. Everything was just as listed, the home was in the perfect location, well stocked, and beautiful inside. We would definitely return again. "
The price is CA $550
CA $814 total
includes taxes & fees
Aug 13 - Aug 14
Scenic New Paltz Escape: River Views, Hot Tub & Deck | Dream House in the Gunks
Charming cottage with lake access, wood burning fire place, and WiFi
Relax in this inviting living room with a sofa, dresser, and small table.

Charming cottage with lake access, wood burning fire place, and WiFi

2.0 star property
9.0 out of 10, Wonderful, (7)
"Oriana was awesome and I look forward to staying there again."
Charming cottage with lake access, wood burning fire place, and WiFi
Walk to Putnam Lake: Updated Home w/ Deck
TV, stereo

Walk to Putnam Lake: Updated Home w/ Deck

Walk to Putnam Lake: Updated Home w/ Deck
Lakehouse, Boat Dock, Kayaks, Fire-Pit, King Bed, 1 Hour & 15 Min from NYC etc!
Enjoy a peaceful lakeside retreat with a barbecue grill and comfortable seating area.

Lakehouse, Boat Dock, Kayaks, Fire-Pit, King Bed, 1 Hour & 15 Min from NYC etc!

9.0 out of 10, Wonderful, (18)
"We really enjoyed our stay. The house is walking distance from the lake and a good break for anyone trying to escape the bustle of NYC. The house was very clean and we felt safe and comfortable here’s the outdoor fire pit was a very nice touch."
Lakehouse, Boat Dock, Kayaks, Fire-Pit, King Bed, 1 Hour & 15 Min from NYC etc!
Ultimate Lakeside Getaway on 5 Acres - Private Dock, Kayaks, Fire Pit - Sleeps 9
Terrace/patio

Ultimate Lakeside Getaway on 5 Acres - Private Dock, Kayaks, Fire Pit - Sleeps 9

9.6 out of 10, Exceptional, (8)
Ultimate Lakeside Getaway on 5 Acres - Private Dock, Kayaks, Fire Pit - Sleeps 9
1 HR NYC Getaway Awesome Newly Renovated Home on 4 Acres, Stunning Views
Cozy living room with a fireplace, flat-screen TV, and comfortable seating area.

1 HR NYC Getaway Awesome Newly Renovated Home on 4 Acres, Stunning Views

9.0 out of 10, Wonderful, (37)
"Perfect spot for a get together with friends... kitchen, dining room and living room all connected so you're always together and not missing out on the fun. Comfy couches and plenty of space for large board games."
1 HR NYC Getaway Awesome Newly Renovated Home on 4 Acres, Stunning Views
Dog friendly private 3-bedroom house bordering the Mohonk Preserve
Escape to a secluded cabin nestled among the trees, with a charming front porch and staircase leading to the upper level.

Dog friendly private 3-bedroom house bordering the Mohonk Preserve

10.0 out of 10, Exceptional, (7)
Dog friendly private 3-bedroom house bordering the Mohonk Preserve
Lake Oasis with Firepit, Game room and Kayaks
Smart TV, table tennis

Lake Oasis with Firepit, Game room and Kayaks

10.0 out of 10, Exceptional, (1)
"This was our family's first time to Candlewood Lake/Squantz Pond. The area is picturesque and the location of this property is perfect. The porch off of the living area directly overlooks Squantz Pond and mountains. The basement was ideal for teenagers with a projector screen, air hockey/pool, and exercise equipment. The bedroom were spacious and beds comfortable. The kitchen/living area are open concept and the whole family could be together. The owner and his daughter are incredibly kind and...
Lake Oasis with Firepit, Game room and Kayaks
The Studio at the Inn at High Falls
Situated in a lush forest, this cabin offers a serene retreat with a symmetrical facade and a well-manicured lawn.

The Studio at the Inn at High Falls

8.0 out of 10, Very good, (26)
"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!"
The price is CA $155
CA $372 total
includes taxes & fees
Aug 11 - Aug 12
The Studio at the Inn at High Falls
Welcome to New Paltz. Charming 3-bedroom house with AC, WIFI,
Private kitchen

Welcome to New Paltz. Charming 3-bedroom house with AC, WIFI,

The price is CA $276
CA $702 total
includes taxes & fees
Aug 11 - Aug 12
Welcome to New Paltz. Charming 3-bedroom house with AC, WIFI,
The Loft At The Inn At High Falls
Cozy attic bedroom with a large bed, bedside table, and window.

The Loft At The Inn At High Falls

9.2 out of 10, Wonderful, (16)
"this was just a lovely stay all around!! Will absolutely stay there again!"
The price is CA $248
CA $492 total
includes taxes & fees
Aug 11 - Aug 12
The Loft At The Inn At High Falls
Modern NY Home w/ Views By Hudson Valley Hiking!
Relax in this stylish living space with a large sofa, matching ottoman, and modern light fixture.

Modern NY Home w/ Views By Hudson Valley Hiking!

9.8 out of 10, Exceptional, (25)
"Lovely home and great proximity to Taconic Parkway for all points north and south. Owner very accomodating"
Modern NY Home w/ Views By Hudson Valley Hiking!
Stylish Pine Plains Home Near Parks & Hiking!
Enjoy cooking in this fully equipped kitchen with a range, oven, microwave, and sink.

Stylish Pine Plains Home Near Parks & Hiking!

9.8 out of 10, Exceptional, (15)
"Place looked great in pictures and turned out to be even better! Will definitely stay there again."
Stylish Pine Plains Home Near Parks & Hiking!
Woodland A-Frame
Spacious living area with a high ceiling, stone accent wall, and kitchen island.

Woodland A-Frame

10.0 out of 10, Exceptional, (1)
"Nice, clean place out in the woods. Enjoyed our stay and had no issues. Host responded quickly and check-in/out was refreshingly simple. Our kid enjoyed the supply of children’s books. "
Woodland A-Frame
Hamptons on the Hudson in South Saugerties
Relax in a cozy outdoor space with a fireplace, wicker furniture, and a scenic view.

Hamptons on the Hudson in South Saugerties

10.0 out of 10, Exceptional, (24)
"Beautiful home and great location . "
Hamptons on the Hudson in South Saugerties
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
"You may want to check the thermometer in 529. It was set on 68 but was more like 78 in the room. Other than that, we had a great stay!"
Kevin 1-night trip
Posted 1 day ago
Hampton Inn & Suites Poughkeepsie