Photo by louann ohora

Pleasant Valley Holiday Rentals

Start date: Check-in selected.
To Date
End date: Check-out
  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Holiday Rentals in Pleasant Valley

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

Kingston
9.6 out of 10, Exceptional, (14)
"Great little space. Perfect for two adults. Chill living room and well appointed kitchen. It’s a perfect alternative to a hotel, and reasonably priced for what you get. "
United States
Chris S.
The price is AU$437
includes taxes & fees
10 Dec - 11 Dec
Retro Retreat: renovated 2BR, desk, no chore list!

Cabin in the heart of the Hudson Valley, Cabin 3

Newburgh
9.8 out of 10, Exceptional, (14)
"We are moving to the area and found this cute place. Loved it and will stay here again. "
United States
Nicole G.
The price is AU$434
includes taxes & fees
30 Nov - 1 Dec
Cabin in the heart of the Hudson Valley, Cabin 3

Luxe Studio 2 on Main Street- Luxury Steam Shower, Kitchen

Beacon
10.0 out of 10, Exceptional, (32)
"Great time and great place to stay "
United States
S S.
The price is AU$376
includes taxes & fees
14 Dec - 15 Dec
Luxe Studio 2 on Main Street- Luxury Steam Shower, Kitchen

Campfire Cottage: Fireplace, fire pit & no chores!

Kingston
10.0 out of 10, Exceptional, (29)
"Great multi-week stay! Would certainly stay again. "
United States
Jim R.
The price is AU$375
includes taxes & fees
2 Dec - 3 Dec
Campfire Cottage: Fireplace, fire pit & no chores!

Mid-Century DJ’s Dream

Staatsburg
10.0 out of 10, Exceptional, (43)
"Location is well furnished and near many attractionHost versatile and well versed"
United States
Alberto M.
The price is AU$302
includes taxes & fees
30 Nov - 1 Dec
Mid-Century DJ’s Dream

Cabin in the Heart of the Hudson Valley, Cabin 1

Newburgh
10.0 out of 10, Exceptional, (31)
"Great overnight spot, especially with a dog."
United States
Ed C.
The price is AU$430
includes taxes & fees
1 Dec - 2 Dec
Cabin in the Heart of the Hudson Valley, Cabin 1

Private Studio Close to Downtown Rhinebeck

RHINEBECK
10.0 out of 10, Exceptional, (25)
"This a an adorable, well designed, spotless space which was perfect for our over night stay in Rhinebeck. Property a quick walk away from the fairgrounds and downtown was also walkable…the host was absolutely amazing with great communication and detailed instructions! "
United States
Kathy
Private Studio Close to Downtown Rhinebeck

Secluded Mountaintop Retreat – Rustic Luxury & Panoramic Views at Freedom Farm

1.0 star property
New Milford
8.0 out of 10, Very good, (1)
"We camped at Freedom Farm and enjoyed the secluded woods setting for our tent. Everything was clean and well prepared for our stay, and the hosts were friendly and helpful. It is beautifully situated and is a short drive from some excellent hiking and biking in nearby state parks. I think a couple of things, though, could be improved. The tent was set up on an incline, which made sleeping a bit less comfortable than it might have been. I would recommend that the hosts build a level platform...
United States
Eric
The price is AU$297
includes taxes & fees
30 Nov - 1 Dec
Secluded Mountaintop Retreat – Rustic Luxury & Panoramic Views at Freedom Farm

Romantic Apartment in Historic Stone Ridge

Stone Ridge
9.4 out of 10, Exceptional, (18)
"Very quiet and immaculate. Hosts were very easy to communicate with and gracious. "
United States
Myra D.
The price is AU$251
includes taxes & fees
3 Dec - 4 Dec
Romantic Apartment in Historic Stone Ridge

Retro Retreat: 1br home w/ WFH desk, livingroom, fire pit and no chores!

Kingston
10.0 out of 10, Exceptional, (4)
"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 AU$342
includes taxes & fees
10 Dec - 11 Dec
Retro Retreat: 1br home w/ WFH desk, livingroom, fire pit and no chores!

THE ARTIST’S LOFT- Peaceful 1-bedroom apartment in lovely Red Hook with AC, WiFi

Red Hook
9.4 out of 10, Exceptional, (11)
"The loft was easy to find and the perfect location for attending events at Bard and beery picking.Well stocked kitchen and spacious loving room."
United States
Nancy K.
The price is AU$333
includes taxes & fees
30 Nov - 1 Dec
THE ARTIST’S LOFT- Peaceful 1-bedroom apartment in lovely Red Hook with AC, WiFi

Modern Hudson Valley Retreat Near Mohonk

2.0 star property
Plattekill
10.0 out of 10, Exceptional, (2)
"Beautiful location and great stay! Would come here again in a heartbeat. "
United States
Gavin
The price is AU$404
includes taxes & fees
30 Nov - 1 Dec
Modern Hudson Valley Retreat Near Mohonk

Grant - A Tranquil One Bedroom Steps from River

Newburgh
9.6 out of 10, Exceptional, (38)
"Stan is really nice and helpful. The apartment is really well designed, spacious and clean, very well equipped with a nice porch. Stan is really thoughtful. Recommended!"
United States
Zohar
The price is AU$430
includes taxes & fees
29 Dec - 30 Dec
Grant - A Tranquil One Bedroom Steps from River

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

Carmel Hamlet
9.8 out of 10, Exceptional, (12)
"We loved the cleanliness, the location near the lake and the neighborhood restaurant, The Great Blue Heron."
United States
Hannah P.
The price is AU$546
includes taxes & fees
30 Nov - 1 Dec
Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.

Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park

Hopewell Junction
9.0 out of 10, Wonderful, (10)
"We had a great last minute visit to Hopewell Junction and enjoyed a lovely stay at the chapel! It’s a very unique experience and quiet and peaceful. We enjoyed the bbq and an evening fire with smores! "
United States
Esther P.
The price is AU$402
includes taxes & fees
30 Nov - 1 Dec
Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park

Mid Century Modern Studio w/ Full Kitchen - Newly Built

Kent
9.8 out of 10, Exceptional, (9)
"The studio is so fun with great amenities and a gorgeous view. "
United States
Kimberly
The price is AU$388
includes taxes & fees
9 Dec - 10 Dec
Mid Century Modern Studio w/ Full Kitchen - Newly Built

Hot Tub - Fire Pit - BBQ - Hammock - Colonial

Kingston
9.4 out of 10, Exceptional, (22)
"This was a great stay away, just for a couple of quiet days. Inside the house was excellent. "
United States
Dennis M.
The price is AU$356
includes taxes & fees
2 Dec - 3 Dec
Hot Tub - Fire Pit - BBQ - Hammock - Colonial

The Studio at the Inn at High Falls

High Falls
8.0 out of 10, Very good, (32)
"We loved our studio — it was cozy, charming, and fit our needs perfectly. Frank went above and beyond to make us feel comfortable, and his hospitality really stood out. Everything was spotless and well-kept, and we had everything we needed for a relaxing stay. The location was convenient, the space felt welcoming, and little touches made it even more enjoyable. We would definitely stay here again and highly recommend it to anyone looking for a comfortable and stress-free getaway!"
United States
Ya-elle G.
The price is AU$417
includes taxes & fees
6 Dec - 7 Dec
The Studio at the Inn at High Falls

Dog-Friendly Hudson Valley Escape with Hot Tub & Jacuzzi

Kingston
9.6 out of 10, Exceptional, (25)
"A lovely place and Seth is always so helpful."
United States
Lynn L.
The price is AU$363
includes taxes & fees
2 Dec - 3 Dec
Dog-Friendly Hudson Valley Escape with Hot Tub & Jacuzzi

Luxe Studio #3 on Main Street- Amazing Steam Shower! Washer/Dryer, Kitchen

Beacon
9.8 out of 10, Exceptional, (42)
"Adorable place to stay in an adorable town! "
United States
Mary L.
The price is AU$381
includes taxes & fees
14 Dec - 15 Dec
Luxe Studio #3 on Main Street- Amazing Steam Shower! Washer/Dryer, 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.

Black Friday Sale

Save up to 40% on select hotels
Save an average of 15% on thousands of hotels when you're signed in

Top Pleasant Valley Hotel Reviews

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$302 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?

Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo: This holiday home rental outside of Pleasant Valley offers a fireplace, a patio and air conditioning to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms, as well as a kitchen with an oven, a microwave and a coffee maker, so that you can cook with friends or family. 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 8 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.