A row of houses with a mountain in the background.

Search Vacation Homes in Pleasant Valley

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

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

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Oct 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

Our top choices for Pleasant Valley vacation homes

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

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

Stunning 5-bedroom house with AC / Heat in charming Poughkeepsie NY
Poughkeepsie
9.6 out of 10, Exceptional, (5 reviews)
"Beautiful property with ample space for parking. Host was super nice and met all of our needs!"
United States
Nicole Y.
The price is ￥25,294
￥67,983 total
includes taxes & fees
Sep 28 - Sep 29
Stunning 5-bedroom house with AC / Heat in charming Poughkeepsie NY
A modern kitchen with a granite countertop, stainless steel appliances, and a built-in oven.

2. Campfire Cottage: Fireplace, fire pit & no chores!

Campfire Cottage: Fireplace, fire pit & no chores!
Kingston
10.0 out of 10, Exceptional, (33 reviews)
"Great multi-week stay! Would certainly stay again. "
United States
Jim R.
The price is ￥13,698
￥41,970 total
includes taxes & fees
Sep 28 - Sep 29
Campfire Cottage: Fireplace, fire pit & no chores!
A rural landscape with a barn, a silo, and a bridge with rocks and purple flowers in the foreground.

3. A Cozy Private Suite Near New Paltz: Farms, Nature, Hiking & Bike the rail trail

A Cozy Private Suite Near New Paltz: Farms, Nature, Hiking & Bike the rail trail
Wallkill
9.2 out of 10, Wonderful, (15 reviews)
"The room was super cute and clean. It had everything that I needed."
United States
Carrie
The price is ￥10,770
￥21,763 total
includes taxes & fees
Sep 29 - Sep 30
A Cozy Private Suite Near New Paltz: Farms, Nature, Hiking & Bike the rail trail
A modern kitchen with white cabinets, a built-in toaster, a blender, and a window with a view of trees.

4. Amazing 3-bedroom house with AC in adorable Highland

Amazing 3-bedroom house with AC in adorable Highland
Highland
The price is ￥41,803
￥84,028 total
includes taxes & fees
Sep 29 - Sep 30
Amazing 3-bedroom house with AC in adorable Highland
A compact kitchen with blue cabinets, a white stove, and yellow chairs.

5. 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 ￥12,911
￥41,265 total
includes taxes & fees
Oct 14 - Oct 15
Retro Retreat: 1br home w/ WFH desk, livingroom, fire pit and no chores!
A bedroom with a bed, a TV mounted on the wall, a window with a view of greenery, and a small seating area with a table and chairs.

6. 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, (46 reviews)
"The pictures are misleading"
United States
Jia
The price is ￥17,713
￥42,587 total
includes taxes & fees
Sep 27 - Sep 28
The Studio at the Inn at High Falls
A rustic cabin with a chimney, surrounded by dense autumn foliage and a narrow road.

7. Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park

Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park
Hopewell Junction
9.4 out of 10, Exceptional, (13 reviews)
"Lovely space and situation, unique. Close to the AT, as well."
United States
Peter W.
The price is ￥26,609
￥43,995 total
includes taxes & fees
Sep 27 - Sep 28
Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park
A spacious living room with a large wooden dining table, a comfortable sofa, and a bookshelf filled with books and decorative items.

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

Steps to the Delightful Village of Millbrook ☆ Fun Family Getaway
Millbrook
10.0 out of 10, Exceptional, (6 reviews)
"This is a charming, historic, well-maintained home on a beautifully landscaped lot. The updates in the home balance a respect for tradition while also providing modernization. The village of Millbrook is a quintessential twee New England village. The house felt very comfortable and homey and the caretaker was attentive and accommodating. We enjoyed our stay!"
United States
Beth E.
The price is ￥62,980
￥131,984 total
includes taxes & fees
Sep 29 - Sep 30
Steps to the Delightful Village of Millbrook ☆ Fun Family Getaway
A wooden deck with a wood-burning stove and a door leading to an outdoor area with chairs.

9. Historic Hudson Valley Farmhouse w/ Sauna in Stone Ridge Hamlet

Historic Hudson Valley Farmhouse w/ Sauna in Stone Ridge Hamlet
Stone Ridge
10.0 out of 10, Exceptional, (3 reviews)
"Great tastefully kept property. Our family including the 8 year felt we should have stayed here longer."
United States
Tarun
The price is ￥11,501
￥30,082 total
includes taxes & fees
Sep 28 - Sep 29
Historic Hudson Valley Farmhouse w/ Sauna in Stone Ridge Hamlet
A spacious living area with a staircase, a dining table, and a sofa.

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

Our home is perfect for relaxing and having lots of fun, with near by activity’s
Highland
9.6 out of 10, Exceptional, (13 reviews)
"We had was great time and the host Mary was amazing and excellent at communicating. Everything was perfect in the home. Thank you"
United States
Pinal
The price is ￥38,175
￥114,548 total
includes taxes & fees
Sep 29 - Sep 30
Our home is perfect for relaxing and having lots of fun, with near by activity’s
A living room with a fireplace, a glass coffee table, a red sofa, and a large window with a view of a brick wall.

11. The Quaint House: Modern Heritage in Roundout Kingston Waterfront

The Quaint House: Modern Heritage in Roundout Kingston Waterfront
Rondout
9.4 out of 10, Exceptional, (3 reviews)
"We had a wonderful toi-même in this lovely home. Everything was perfect. The town is lovely. So interesting and so much history as well. Best 2 days. We hope to come back here. Very soon "
United States
Claire A.
The Quaint House: Modern Heritage in Roundout Kingston Waterfront
An outdoor patio area with a covered seating area, a pool, and potted plants.

12. 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, (78 reviews)
"It’s was nice, clean and the outdoor out area was really nice."
United States
Roger S.
The price is ￥41,134
￥53,752 total
includes taxes & fees
Sep 27 - Sep 28
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
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.

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

Chilly Days Hiking, Quiet Yard, an Easy Escape Near New Paltz
New Paltz
10.0 out of 10, Exceptional, (8 reviews)
"Superb property - comfortable, spotless, all the amenities you could need, and lots of space. "
United States
Thomas B.
The price is ￥27,577
￥96,307 total
includes taxes & fees
Sep 29 - Sep 30
Chilly Days Hiking, Quiet Yard, an Easy Escape Near New Paltz
A view from a room with a sliding glass door leading to an outdoor deck with a wooden fence, a chair, and a bench.

14. Esopus Creek modern Tiny house Retreat in Woodstock &Kingston Catskill area!

Esopus Creek modern Tiny house Retreat in Woodstock &Kingston Catskill area!
Kingston
9.6 out of 10, Exceptional, (101 reviews)
"Wonderful stay. "
United States
Chris L.
The price is ￥26,924
￥41,088 total
includes taxes & fees
Sep 27 - Sep 28
Esopus Creek modern Tiny house Retreat in Woodstock &Kingston Catskill area!
A modern living room with a grey sofa, a wooden coffee table, and a staircase leading to an upper floor.

15. Chic Barn Style * Fireplace * Near Stissing House

Chic Barn Style * Fireplace * Near Stissing House
Pine Plains
10.0 out of 10, Exceptional, (3 reviews)
"We loved the property and everything was so welcoming! Having a pool there would be the best addition for this place!"
United States
Estefany G.
The price is ￥27,711
￥104,095 total
includes taxes & fees
Sep 29 - Sep 30
Chic Barn Style * Fireplace * Near Stissing House
A room with a bed, a couch, a desk with a computer, and various wall decorations.

16. Spacious 4-bedroom estate in adorable Carmel Hamlet with AC

Spacious 4-bedroom estate in adorable Carmel Hamlet with AC
Carmel Hamlet
The price is ￥32,750
￥44,537 total
includes taxes & fees
Sep 28 - Sep 29
Spacious 4-bedroom estate in adorable Carmel Hamlet with AC
A kitchen with wooden cabinets, a black countertop, a sink, and a window with a view of trees.

17. "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 ￥31,175
￥89,948 total
includes taxes & fees
Sep 30 - Oct 1
"Country outside the city " 3 bedrooms 2 full bathrooms
A kitchen with grey cabinets, a stone floor, and a view of a garden through an open door.

18. Historic Cottage * Steam Shower * Chef’s Kitchen

Historic Cottage * Steam Shower * Chef’s Kitchen
Kingston
10.0 out of 10, Exceptional, (1 review)
"We had a great time staying here! The house is a gorgeous historic house with modern amenities. It was a short drive to Kingston which was super convenient. We loved that we could bring our dog with us as well. It is on a main road, but we didn't find that to be a disturbance at all. I would definitely come back here again!!"
United States
Laura D.
The price is ￥21,130
￥75,269 total
includes taxes & fees
Sep 29 - Sep 30
Historic Cottage * Steam Shower * Chef’s Kitchen

19. Hudson Escape W/ Hot Tub + Bridge View

Hudson Escape W/ Hot Tub + Bridge View
Highland
The price is ￥81,480
￥143,459 total
includes taxes & fees
Oct 1 - Oct 2
Hudson Escape W/ Hot Tub + Bridge View
A spacious living room with a fireplace, a dining area with a view of a lake, and a cozy seating arrangement.

20. 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, (20 reviews)
"Beautiful house. Great location and awesome hosts!"
United States
Robert T.
The price is ￥35,143
￥66,072 total
includes taxes & fees
Oct 5 - Oct 6
Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Pleasant Valley Hotel Reviews

Hampton Inn & Suites Poughkeepsie

Hampton Inn & Suites Poughkeepsie

10/10 Excellent
"Peaceful clean good breakfast loved the front desk people. I’m so glad I chose this property. Would 10 out of 10 stay here again"
Cecilia 2-night trip
Posted 4 hours ago
Hampton Inn & Suites Poughkeepsie

Find out more about Pleasant Valley

Pleasant Valley Vacation Homes information

Number of reviews
322
Accommodation
376 Vacation Homes
Lowest Price
￥21,763
Highest Price
￥143,459