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Pleasant Valley Holiday Rentals

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Holiday Rentals in Pleasant Valley

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

Fishkill
9.6 out of 10, Exceptional, (45)
"Plenty of seating & comfortable beds were a plus! The theatre room was really fun for grandkids!"
United States
Lisa B.
The price is NZ$591
includes taxes & fees
30 Nov - 1 Dec
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo

Esopus Creek modern Tiny house Retreat!

Kingston
9.8 out of 10, Exceptional, (60)
"The property was beautiful. Quiet area but close enough to all the places we wanted to go. Our hosts were very gracious, attentive and friendly. Enjoyed our weekend retreat. "
United States
Rebecca
The price is NZ$460
includes taxes & fees
13 Nov - 14 Nov
Esopus Creek modern Tiny house Retreat!

Hamptons on the Hudson in South Saugerties

Glasco
10.0 out of 10, Exceptional, (33)
"The entire process and stay were flawless. We had a rush booking and every request we had was accommodated. I give the highest recommendation and will hopefully being staying here again."
United States
Gordon V.
Hamptons on the Hudson in South Saugerties

Lakehouse Boat Dock, Kayaks, Fire-Pit, Pool Table, Air Hockey, Hammock, King Bed

New Fairfield
9.4 out of 10, Exceptional, (31)
"I stayed here for three nights with my elderly mom. The home is lovely and very comfortable, with lovely linens, updated bathrooms, and luxurious beds. The kitchen is wonderfully equipped for anything you might want to prepare. This would be an excellent spot for a family with children. The hosts were very responsive and gracious. Above all else, the view is absolutely spectacular. I wish i could wake up to it every day. I hope to go back in the fall when the leaves are changing. Highly...
United States
Virginia F.
Lakehouse Boat Dock, Kayaks, Fire-Pit, Pool Table, Air Hockey, Hammock, King Bed

The Farm at Hyde Park

Staatsburg
9.8 out of 10, Exceptional, (84)
"We enjoyed our stay...lots to do in the area. Glen was very friendly and accommodating. "
United States
Robert W.
The Farm at Hyde Park

Cabin in the heart of the Hudson Valley, Cabin 2

Newburgh
9.4 out of 10, Exceptional, (27)
"My partner and I stayed at the cabin for a writing retreat/getaway. It served us well and was perfect for our short trip. The host, Julie was very kind and helpful throughout our stay!"
United States
Thani B.
The price is NZ$312
includes taxes & fees
13 Nov - 14 Nov
Cabin in the heart of the Hudson Valley, Cabin 2

Large,Cozy,Bright Apartment, Business Themed.

Newburgh
9.0 out of 10, Wonderful, (15)
"Very cozy stay with responsive host"
United States
Adhith P.
The price is NZ$1,225
includes taxes & fees
13 Nov - 14 Nov
Large,Cozy,Bright Apartment, Business Themed.

Mid-Century DJ’s Dream

Staatsburg
10.0 out of 10, Exceptional, (43)
"Great place to stay! Close to many attractions by car - most 10-15 minutes. Clean and comfortable. Kevin has lots of great suggestions on places to go and restaurants."
United States
Anonymous traveller
The price is NZ$346
includes taxes & fees
18 Nov - 19 Nov
Mid-Century DJ’s Dream

Grant - A Tranquil One Bedroom Steps from River

Newburgh
9.6 out of 10, Exceptional, (37)
"Was great. A Beautiful place!"
United States
Bryan S.
The price is NZ$459
includes taxes & fees
17 Nov - 18 Nov
Grant - A Tranquil One Bedroom Steps from River

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

Newburgh
10.0 out of 10, Exceptional, (311)
"Beautiful location- owner was very responsive to any questions we had."
United States
Richard K.
Cozy Lakefront Home - 278 FIVE STAR Reviews - Kayaks, Sunsets & Panoramic Views

Rustic Cabin in Fishkill!

Fishkill
10.0 out of 10, Exceptional, (3)
"Ideal cabin getaway. "
United States
Nadja E.
The price is NZ$801
includes taxes & fees
13 Nov - 14 Nov
Rustic Cabin in Fishkill!

Hot Tub - Fire Pit - BBQ - Hammock - Colonial

Kingston
9.4 out of 10, Exceptional, (22)
"We came down with our dog. We work a lot and needed a break. The place is cozy and comfy and the outdoor space is so lovely. Good mix of sunny space and shaded space.Our dog very much enjoyed the backyard and we loved the small businesses within walking distance "
United States
Heather H.
The price is NZ$413
includes taxes & fees
18 Nov - 19 Nov
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)
"Lovely!"
United States
Julia H.
The price is NZ$475
includes taxes & fees
13 Nov - 14 Nov
The Studio at the Inn at High Falls

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

Carmel Hamlet
10.0 out of 10, Exceptional, (93)
"We loved our stay. It was great for a family Thanksgiving"
United States
Edmund F.
Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.

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 NZ$432
includes taxes & fees
18 Nov - 19 Nov
Dog-Friendly Hudson Valley Escape with Hot Tub & Jacuzzi

Spacious A-Frame w/ Game Room, Fire Pit & Modern Comforts in Hudson Valley

New Paltz
10.0 out of 10, Exceptional, (9)
"The house exceeded expectations. Extremely clean especially considering small dogs are allowed. The bedrooms are spacious. Everything is furnished beautifully, and the basement game room was a winner. Although there was snow, the kids still loved playing in the yard and morning coffee on the deck cannot be beat. The only thing that caused us trouble was the stove but I’m not used to a convection rangtop. "
United States
Mary M.
The price is NZ$1,740
includes taxes & fees
13 Nov - 14 Nov
Spacious A-Frame w/ Game Room, Fire Pit & Modern Comforts in Hudson Valley

Totally secluded Yurt surrounded by waterfalls, brooks, cliffs and forest

Ulster Park
10.0 out of 10, Exceptional, (95)
"We loved this stay! The yurt was absolutely charming! Such an amazing location within easy distance of hiking and the Empire State Trail bicycle path, plus great dining in New Paltz and Kingston."
United States
David W.
Totally secluded Yurt surrounded by waterfalls, brooks, cliffs and forest

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

Newburgh
9.8 out of 10, Exceptional, (20)
"The house was beautiful inside and out. Owners were so nice and made sure we had everything we needed for our weekend getaway."
United States
Cindy B.
Ultimate Lakeside Getaway on 5 Acres - Private Dock, Kayaks, Fire Pit - Sleeps 9

Sexiest Lil Cabin in Saugerties, NY

Saugerties
9.0 out of 10, Wonderful, (13)
"We loved our stay here, it was the perfect short getaway. Thanks Alexandria!"
United States
Julie L.
Sexiest Lil Cabin in Saugerties, NY

Stunning 5-bedroom house with AC / Heat in charming Poughkeepsie NY

Poughkeepsie
10.0 out of 10, Exceptional, (2)
"House worked perfectly for our needs. Newly renovated home. Parking was plentiful behind the home. "
United States
Wayne S.
The price is NZ$1,031
includes taxes & fees
16 Nov - 17 Nov
Stunning 5-bedroom house with AC / Heat in charming Poughkeepsie 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

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 favorite 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 depends 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 NZ$312 per night. Entering your travel dates in the search wizard you might find 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.