Book Holiday Homes in Pleasant Valley

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Featured Holiday Homes in Pleasant Valley

Esopus Creek modern Tiny house Retreat!

Esopus Creek modern Tiny house Retreat!

Kingston
The price is AU$380 per night from 29 Apr to 30 Apr
AU$380
includes taxes & fees
29 Apr - 30 Apr
With a stay at this vacation home in Kingston, you'll be on a river, just steps from Catskill State Park and a 4-minute drive from Thorn Preserve - Catskill ...
Esopus Creek modern Tiny house Retreat!
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
The price is AU$526 per night from 28 Apr to 29 Apr
AU$526
includes taxes & fees
28 Apr - 29 Apr
When you stay at this vacation home in Fishkill, you'll be within a 10-minute drive of Northeast Regional Epilepsy Group and SplashDown Beach.
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
Hiking & Climbing Paradise- walking distance to Mohonk,Gunks,Minnewaska

Hiking & Climbing Paradise- walking distance to Mohonk,Gunks,Minnewaska

New Paltz
A stay at this vacation home places you in the heart of New Paltz, a 5-minute drive from Mohonk Preserve Visitor Center and 6 minutes from Testimonial ...
Hiking & Climbing Paradise- walking distance to Mohonk,Gunks,Minnewaska
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Spacious New Luxurious holiday house in lovely Hudson Valley

Spacious New Luxurious holiday house in lovely Hudson Valley

Poughkeepsie
The price is AU$1,457 per night from 1 May to 2 May
AU$1,457
includes taxes & fees
1 May - 2 May
With a stay at this vacation home in Poughkeepsie, you'll be within a 15-minute drive of Vassar College and Marist College.
Spacious New Luxurious holiday house in lovely Hudson Valley
Hamptons on the Hudson in South Saugerties

Hamptons on the Hudson in South Saugerties

Glasco
With a stay at this vacation home, you'll be centrally located in Glasco, just a 3-minute walk from Hudson River and 11 minutes by foot from Falling Waters ...
Hamptons on the Hudson in South Saugerties
1 HR NYC Getaway Awesome Newly Renovated Home on 4 Acres, Stunning Views

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

Hopewell Junction
Located in Hopewell Junction, this vacation home is in the mountains, within a 10-minute drive of Clarence Fahnestock State Park and Hudson Valley Research ...
1 HR NYC Getaway Awesome Newly Renovated Home on 4 Acres, Stunning Views
Cozy cottage w/hot tub, game room & backyard. Close to West Point and Bethel.

Cozy cottage w/hot tub, game room & backyard. Close to West Point and Bethel.

New Windsor
With a stay at this vacation home in New Windsor, you'll be on a river, within a 10-minute drive of United States Military Academy and Hudson River.
Cozy cottage w/hot tub, game room & backyard. Close to West Point and Bethel.
Hidden Charm in Hudson Valley In Dutchess County

Hidden Charm in Hudson Valley In Dutchess County

2 out of 5
Salt Point
Located in Salt Point, this vacation home is in the mountains, within a 15-minute drive of Clinton Vineyards and Institute of Ecosystem Studies.
Hidden Charm in Hudson Valley In Dutchess County
Private Lakefront Home With Kayaks * Stunning Sunsets * Panoramic View

Private Lakefront Home With Kayaks * Stunning Sunsets * Panoramic View

Newburgh
The price is AU$819 per night from 28 Apr to 29 Apr
AU$819
includes taxes & fees
28 Apr - 29 Apr
When you stay at this vacation home in Newburgh, you'll be on the waterfront, within a 5-minute drive of Ice Time Sports Complex and Algonquin Park.
Private Lakefront Home With Kayaks * Stunning Sunsets * Panoramic View
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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.

Pleasant Valley Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Pleasant Valley vacation homes are the perfect way for you to wing it.

Holiday houses in Pleasant Valley let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Pleasant Valley in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Pleasant Valley adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Pleasant Valley with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Pleasant Valley vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Top trending hotels in Pleasant Valley

Best Western Plus Kingston Hotel And Conference Center

Best Western Plus Kingston Hotel And Conference Center

2.5 out of 5
503 Washington Ave, Kingston, NY
Fully refundableReserve now, pay when you stay
The price is AU$199 per night from 4 May to 5 May
AU$199
includes taxes & fees
4 May - 5 May
Located in Kingston, Best Western Plus Kingston Hotel And Conference Center is in the historical district, a 5-minute walk from Dietz Stadium and 10 minutes ...
Best Western Plus Kingston Hotel And Conference Center
HYATT house Fishkill/Poughkeepsie

HYATT house Fishkill/Poughkeepsie

3 out of 5
100 Westage Business Center Dr., Fishkill, NY
Fully refundableReserve now, pay when you stay
The price is AU$186 per night from 30 Apr to 1 May
AU$186
includes taxes & fees
30 Apr - 1 May
Located in Fishkill, HYATT house Fishkill/Poughkeepsie is a 4-minute drive from SplashDown Beach and 10 minutes from Dia Beacon.
HYATT house Fishkill/Poughkeepsie
Inn at Bellefield / Hyde Park, Residence Inn by Marriott

Inn at Bellefield / Hyde Park, Residence Inn by Marriott

3 out of 5
25 OLD VINEYARD PLACE, Hyde Park, NY
Fully refundableReserve now, pay when you stay
The price is AU$285 per night from 18 May to 19 May
AU$285
includes taxes & fees
18 May - 19 May
Located in Hyde Park, Inn at Bellefield / Hyde Park, Residence Inn by Marriott is a 3-minute drive from Hudson River and 9 minutes from Vassar College.
Inn at Bellefield / Hyde Park, Residence Inn by Marriott
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DoubleTree by Hilton Poughkeepsie

DoubleTree by Hilton Poughkeepsie

4 out of 5
40 Civic Center Plz, Poughkeepsie, NY
Fully refundableReserve now, pay when you stay
The price is AU$216 per night from 11 May to 12 May
AU$216
includes taxes & fees
11 May - 12 May
With a stay at DoubleTree by Hilton Poughkeepsie, you'll be centrally located in Poughkeepsie, within a 5-minute drive of Marist College and Vassar College.
DoubleTree by Hilton Poughkeepsie
Don't see what you're looking for?
See all available properties in Pleasant Valley
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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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^Subject to availability and chosen travel dates.