Pleasant Valley Holiday Rentals from NZ$143: Search Short-Term Rentals

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Our top choices for Pleasant Valley holiday rentals

A compact kitchen with white cabinets, a black refrigerator, and a microwave. There is a wooden dining table with a chair, and a sofa with a decorative pillow.

1. Hudson Valley Farm Getaway- West/Llama Lover Lane

Hyde Park

alexandra a.

includes taxes & fees

11 Nov - 12 Nov

A modern kitchen with a granite countertop, a built-in stove, and a dining area with a glass table and chairs.

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

Poughkeepsie

Nicole Y.

includes taxes & fees

16 Nov - 17 Nov

A white house with a steeply pitched roof and a small tower-like structure.

3. Charming 2-bedroom apartment on 2nd floor in Millbrook NY, right in the village

Millbrook

Laurie F.

includes taxes & fees

11 Nov - 12 Nov

A modern kitchen with white cabinets, a central island, and a view to the outside.

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

Staatsburg

elizabeth

includes taxes & fees

9 Dec - 10 Dec

A spacious living room with a large wooden dining table, a comfortable sofa, and a bookshelf filled with books and decorative items.

5. Steps to the Delightful Village of Millbrook ☆ Fun Family Getaway

Millbrook

Beth E.

includes taxes & fees

15 Nov - 16 Nov

6. Hudson Valley Farm Getaway-East/Alpaca Lane-Apt 1

Hyde Park

Meg H.

includes taxes & fees

11 Nov - 12 Nov

A spacious living area with a staircase, a dining table, and a sofa.

7. Our home is perfect for relaxing and having lots of fun, with near by activity’s

Highland

Pinal

includes taxes & fees

11 Nov - 12 Nov

A neatly made bed with a white pillow, a red pillow, and a white blanket. There is a small bedside table with a lamp.

8. Hibiscus Suite - Private Studio Apartment in Rhinebeck Village

Rhinebeck Village

Heather O.

includes taxes & fees

6 Dec - 7 Dec

A wooden porch with white rocking chairs and a hanging flower basket.

9. Step into history & unwind at Elixir apt a charming 🏡 at the❤️of NYHudson Valley

Highland

Laurie G.

includes taxes & fees

11 Nov - 12 Nov

A porch with white railings and multiple chairs.

10. Step into history & unwind at Spring apt a charming 🏡 at the❤️of NYHudson Valley

Highland

Rebecca D.

includes taxes & fees

11 Nov - 12 Nov

A wooden deck with outdoor furniture, surrounded by lush greenery and a small garden.

11. SUPERB VILLAGE LOCATION!! SWEET APARTMENT w/PRIVATE DECK in historic district

New Paltz

Jehiah B.

includes taxes & fees

11 Nov - 12 Nov

A small, two-story house with a red and gray exterior, a front porch with blue chairs, and a table.

12. Cabin in the heart of the Hudson Valley, Cabin 4

Newburgh

Albert

includes taxes & fees

11 Nov - 12 Nov

A covered outdoor deck with wicker furniture, a grill, and a view of a lake.

13. Chic Lakeside Oasis|Near Rhinebeck & Millbrook

Stanfordville

includes taxes & fees

11 Nov - 12 Nov

A living room with a fireplace, two armchairs, a sofa, and a TV.

14. Mid Century Modern Studio w/ Full Kitchen - Newly Built

Kent

benjamin

includes taxes & fees

11 Nov - 12 Nov

A wooden gate leading to a driveway with a stone pathway, surrounded by greenery and a house in the background.

15. Maple Ridge Modern Rustic Retreat where Modern comfort meets Rustic Charm

Ulster Park

Emily F.

includes taxes & fees

15 Nov - 16 Nov

A hot tub on a wooden deck with a view of a river and trees.

16. Welcome to The Boathouse! Waterfront/Boats/Hot tub

New Paltz

Thomas S.

includes taxes & fees

17 Nov - 18 Nov

A compact living space with a kitchenette, a sofa, a bed, and a colorful rug.

17. Cabin in the Heart of the Hudson Valley, Cabin 1

Newburgh

Tim G.

includes taxes & fees

11 Nov - 12 Nov

An outdoor patio area with a covered seating area, a pool, and potted plants.

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

Fishkill

Sara

includes taxes & fees

15 Nov - 16 Nov

A staircase leading to a second floor, a sofa with a throw blanket, a floor lamp, a small table with a vase of sunflowers, and a kitchen area visible through an archway.

19. Chilly Days Hiking, Quiet Yard, an Easy Escape Near New Paltz

New Paltz

Thomas B.

includes taxes & fees

11 Nov - 12 Nov

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Find holiday rentals that suit your style

Top Pleasant Valley Hotel Reviews

An outdoor seating area with stone walls, a fire feature, and yellow chairs.

Home2 Suites By Hilton Poughkeepsie

Poughkeepsie

8/10 Good

Bridget

A courtyard with a fire pit, outdoor seating, and a covered area with string lights.

Homewood Suites by Hilton Poughkeepsie

Poughkeepsie

10/10 Excellent

Jeremy

A hotel entrance with a brick facade, a glass door entrance, and a paved walkway.

Holiday Inn Express Poughkeepsie by IHG

Poughkeepsie

10/10 Excellent

Anne

A modern hotel lobby with wooden flooring, yellow chairs, a long dining table, and pendant lighting.

Hampton Inn & Suites Poughkeepsie

Crown Heights

10/10 Excellent

Anna

A Courtyard by Marriott hotel with a modern design, large windows, and a well-maintained lawn.

Courtyard by Marriott Poughkeepsie

Poughkeepsie

10/10 Excellent

Anonymous traveller

A hotel room with a large bed, two bedside tables with lamps, a headboard with a mirror, a window with curtains, and an air conditioning unit.

Roosevelt Inn of Hyde Park

Hyde Park

10/10 Excellent

CornelisSmit

A spacious living area with a stone fireplace, comfortable seating, a kitchen with bar seating, and large windows.

Residence Inn by Marriott Poughkeepsie

Poughkeepsie

8/10 Good

Peter

A hotel reception area with a reception desk, a waiting area with sofas, and a glass door entrance.

Quality Inn Poughkeepsie

Arlington

8/10 Good

I stayed at the Quality Inn Poughkeepsie just as it was completing renovations in June, 2022, so everything was sparkling new and in perfect working order -- except, as usual, the hotel internet. I would have given the property a 5-star review, except they have farmed out their internet to a dodgy provider, and it simply doesn't work. The property is on the very edge of Poughkeepsie, a few walkable blocks from Vassar College and one block from a 24-hour diner. Strangely, the Quality Inn (with...

Anonymous traveller

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$143 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.

Pleasant Valley Holiday Rentals

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Pleasant Valley holiday rentals

1. Hudson Valley Farm Getaway- West/Llama Lover Lane

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

3. Charming 2-bedroom apartment on 2nd floor in Millbrook NY, right in the village

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

5. Steps to the Delightful Village of Millbrook ☆ Fun Family Getaway

6. Hudson Valley Farm Getaway-East/Alpaca Lane-Apt 1

7. Our home is perfect for relaxing and having lots of fun, with near by activity’s

8. Hibiscus Suite - Private Studio Apartment in Rhinebeck Village

9. Step into history & unwind at Elixir apt a charming 🏡 at the❤️of NYHudson Valley

10. Step into history & unwind at Spring apt a charming 🏡 at the❤️of NYHudson Valley

11. SUPERB VILLAGE LOCATION!! SWEET APARTMENT w/PRIVATE DECK in historic district

12. Cabin in the heart of the Hudson Valley, Cabin 4

13. Chic Lakeside Oasis|Near Rhinebeck & Millbrook

14. Mid Century Modern Studio w/ Full Kitchen - Newly Built

15. Maple Ridge Modern Rustic Retreat where Modern comfort meets Rustic Charm

16. Welcome to The Boathouse! Waterfront/Boats/Hot tub

17. Cabin in the Heart of the Hudson Valley, Cabin 1

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

19. Chilly Days Hiking, Quiet Yard, an Easy Escape Near New Paltz

Find holiday rentals that suit your style

Top Pleasant Valley Hotel Reviews

Home2 Suites By Hilton Poughkeepsie

8/10 Good

Find out more about Pleasant Valley

Pleasant Valley holiday rentals: An excellent choice for every season

How to find incredible deals on Pleasant Valley rentals

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