Pleasant Valley Holiday Rentals

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Check prices for these dates

In two weeks
22 May - 24 May
In two months
3 Jul - 5 Jul
In three months
31 Jul - 2 Aug
In four months
28 Aug - 30 Aug

Our top choices for Pleasant Valley holiday rentals

Property grounds

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, (7 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 HK$627
HK$1,046 total
includes taxes & fees
11 May - 12 May
Rare, peaceful glamping, hot shower, mini golf near appalachian trail
Outdoor dining

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)
"We LOVE this place and have stayed here twice."
United States
jennifer w.
The price is HK$1,010
HK$1,563 total
includes taxes & fees
11 May - 12 May
Cabin in the heart of the Hudson Valley, Cabin 4
TV, fireplace

Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.

Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.
Carmel Hamlet
9.8 out of 10, Exceptional, (13 reviews)
"Beautiful house. Great location and awesome hosts!"
United States
Robert T.
The price is HK$1,585
HK$3,084 total
includes taxes & fees
11 May - 12 May
Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.
1 bedroom, iron/ironing board, free WiFi, bed sheets

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, (32 reviews)
"Cute, clean and perfect for our needs"
United States
Richard H.
The price is HK$1,323
HK$2,201 total
includes taxes & fees
11 May - 12 May
Cabin in the Heart of the Hudson Valley, Cabin 1
Outdoor dining

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

Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
Fishkill
9.2 out of 10, Wonderful, (65 reviews)
"Great spot! Very unique, has lots of charm!"
United States
Brian
The price is HK$2,153
HK$2,852 total
includes taxes & fees
25 May - 26 May
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
Property grounds

Hoppy Hill Farm House

Hoppy Hill Farm House
Dover Plains
9.8 out of 10, Exceptional, (6 reviews)
"Location was great. Accommodations were clean and comfortable. Host was accessible and responsive. Will stay here again if in the area again."
United States
Ken K.
The price is HK$861
HK$1,603 total
includes taxes & fees
11 May - 12 May
Hoppy Hill Farm House
Private kitchen

Pleasant 1-bedroom apartment in Staatsburg perfect for your getaway,

Pleasant 1-bedroom apartment in Staatsburg perfect for your getaway,
Staatsburg
9.0 out of 10, Wonderful, (2 reviews)
"Nice stay for our quick overnight Comfortable space "
United States
jay c.
The price is HK$740
HK$1,457 total
includes taxes & fees
11 May - 12 May
Pleasant 1-bedroom apartment in Staatsburg perfect for your getaway,
Property grounds

Hibiscus Suite - Private Studio Apartment in Rhinebeck Village

Hibiscus Suite - Private Studio Apartment in Rhinebeck Village
Rhinebeck Village
9.8 out of 10, Exceptional, (30 reviews)
"Beautiful place has a great stay!"
United States
Heather O.
The price is HK$1,339
HK$2,746 total
includes taxes & fees
25 May - 26 May
Hibiscus Suite - Private Studio Apartment in Rhinebeck Village
Exterior

Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park

Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park
Hopewell Junction
9.2 out of 10, Wonderful, (11 reviews)
"The chapel was just as it was pictured. It has been beautifully restored. It was a very unique experience."
United States
Stella
The price is HK$1,191
HK$2,020 total
includes taxes & fees
11 May - 12 May
Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park
1 bedroom, free WiFi, bed sheets

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, (35 reviews)
"Instructions were clear. Accommodations were comfortable and clean. Lovely grounds. "
United States
Julia
The price is HK$881
HK$2,126 total
includes taxes & fees
11 May - 12 May
The Studio at the Inn at High Falls
Interior

Esopus Creek modern Tiny house Retreat!

Esopus Creek modern Tiny house Retreat!
Kingston
9.8 out of 10, Exceptional, (76 reviews)
"Beautiful tiny home with a very responsive host! "
United States
Vicky E.
The price is HK$1,339
HK$2,087 total
includes taxes & fees
11 May - 12 May
Esopus Creek modern Tiny house Retreat!
Fridge, microwave, oven, stovetop

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 HK$548
HK$1,912 total
includes taxes & fees
12 May - 13 May
Retro Retreat: 1br home w/ WFH desk, livingroom, fire pit and no chores!
Property grounds

Hudson Valley Farm Getaway- West/Llama Lover Lane

Hudson Valley Farm Getaway- West/Llama Lover Lane
Hyde Park
9.8 out of 10, Exceptional, (7 reviews)
"The stay was great! The listing is very accurate to what the property is, so we very much enjoyed staying in the newly renovated barn. We loved the location, which felt very out-of-the-way but was also only twenty minutes from town. Seeing all of the farm animals and the very friendly barn cat was a plus!"
United States
Marissa S.
The price is HK$1,349
HK$1,738 total
includes taxes & fees
11 May - 12 May
Hudson Valley Farm Getaway- West/Llama Lover Lane
Fridge, microwave, oven, stovetop

"Country outside the city " 3 bedrooms 2 full bathrooms

"Country outside the city " 3 bedrooms 2 full bathrooms
Holmes
9.6 out of 10, Exceptional, (4 reviews)
"Great house! We had a fantastic weekend!! Thank you so much "
United States
pamela w.
The price is HK$1,762
HK$4,650 total
includes taxes & fees
9 Jun - 10 Jun
"Country outside the city " 3 bedrooms 2 full bathrooms
2 bedrooms, desk, free WiFi, bed sheets

Retro Retreat: renovated 2BR, desk, no chore list!

Retro Retreat: renovated 2BR, desk, no chore list!
Kingston
9.6 out of 10, Exceptional, (15 reviews)
"Great, easy, full of everything you’d need. Stayed with 2 others for a work trip and it was perfect! "
United States
Kelley Marie
The price is HK$783
HK$2,473 total
includes taxes & fees
12 May - 13 May
Retro Retreat: renovated 2BR, desk, no chore list!
1 bedroom, iron/ironing board, free WiFi, bed sheets

Cozy country efficiency in the Hudson Valley

Cozy country efficiency in the Hudson Valley
Newburgh
9.8 out of 10, Exceptional, (68 reviews)
"Such a cute place to stay"
United States
Melissa
The price is HK$1,174
HK$2,321 total
includes taxes & fees
11 May - 12 May
Cozy country efficiency in the Hudson Valley
Exterior detail

Luxe Studio 4 On Main Street -Luxury Steam Shower, Views! Kitchen, Washer/ Dryer

Luxe Studio 4 On Main Street -Luxury Steam Shower, Views! Kitchen, Washer/ Dryer
Beacon
10.0 out of 10, Exceptional, (56 reviews)
"Great location and quiet just like we like it. Unit was very charming."
Canada
Thomas
The price is HK$940
HK$1,974 total
includes taxes & fees
3 Jun - 4 Jun
Luxe Studio 4 On Main Street -Luxury Steam Shower, Views! Kitchen, Washer/ Dryer
Terrace/patio

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, (28 reviews)
"The beds were especially comfortable! "
United States
josh p.
The price is HK$705
HK$1,850 total
includes taxes & fees
11 May - 12 May
Dog-Friendly Hudson Valley Escape with Hot Tub & Jacuzzi
Smart TV

Hot Tub - Fire Pit - BBQ - Hammock - Colonial

Hot Tub - Fire Pit - BBQ - Hammock - Colonial
Kingston
9.6 out of 10, Exceptional, (26 reviews)
"The rental was very clean & Beds were very comfortable. "
United States
R.A.G. Time A.
The price is HK$1,018
HK$2,254 total
includes taxes & fees
25 May - 26 May
Hot Tub - Fire Pit - BBQ - Hammock - Colonial
Outdoor dining

Woods Cabin-Kingston/Woodstock, NY.

Woods Cabin-Kingston/Woodstock, NY.
Kingston
The price is HK$1,096
HK$1,587 total
includes taxes & fees
11 May - 12 May
Woods Cabin-Kingston/Woodstock, NY.
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
"Good overall"
Sohail 1-night trip
Posted 10 hours ago
Hampton Inn & Suites Poughkeepsie

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 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 Farm at Hyde Park: This holiday home rental outside of Pleasant Valley is located in a rural location, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. Kick off your shoes and enjoy yourself with a garden and a selection of games.

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.