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Pleasant Valley Vacation Rentals

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Check prices for these dates

In two weeks
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

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 CA $227
CA $617 total
includes taxes & fees
Oct 19 - Oct 20
Stunning 5-bedroom house with AC / Heat in charming Poughkeepsie NY
A spacious living room with a large wooden dining table, a comfortable sofa, and a bookshelf filled with books and decorative items.

2. 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, (7 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 CA $566
CA $1,189 total
includes taxes & fees
Oct 22 - Oct 23
Steps to the Delightful Village of Millbrook ☆ Fun Family Getaway
A spacious living area with a staircase, a dining table, and a sofa.

3. 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 CA $354
CA $1,023 total
includes taxes & fees
Nov 17 - Nov 18
Our home is perfect for relaxing and having lots of fun, with near by activity’s
A modern kitchen with a granite countertop, stainless steel appliances, and a built-in oven.

4. 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 CA $105
CA $361 total
includes taxes & fees
Nov 3 - Nov 4
Campfire Cottage: Fireplace, fire pit & no chores!
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 CA $98
CA $347 total
includes taxes & fees
Nov 2 - Nov 3
Retro Retreat: 1br home w/ WFH desk, livingroom, fire pit and no chores!
A rural landscape with a barn, a silo, and a bridge with rocks and purple flowers in the foreground.

6. 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, (18 reviews)
"The room was super cute and clean. It had everything that I needed."
United States
Carrie
The price is CA $85
CA $183 total
includes taxes & fees
Oct 20 - Oct 21
A Cozy Private Suite Near New Paltz: Farms, Nature, Hiking & Bike the rail trail
A neatly made bed with white bedding and a few colorful pillows, a wooden headboard, and a wall-mounted light fixture.

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

Retro Retreat: renovated 2BR, desk, no chore list!
Kingston
9.6 out of 10, Exceptional, (15 reviews)
"Great, easy, full of everything you’d need. Stayed with 2 others for a work trip and it was perfect! "
United States
Kelley Marie
The price is CA $126
CA $428 total
includes taxes & fees
Nov 2 - Nov 3
Retro Retreat: renovated 2BR, desk, no chore list!
A rustic cabin with a chimney, surrounded by dense autumn foliage and a narrow road.

8. 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 CA $239
CA $402 total
includes taxes & fees
Oct 25 - Oct 26
Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park
A wooden gate leading to a driveway with a stone pathway, surrounded by greenery and a house in the background.

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

Maple Ridge Modern Rustic Retreat where Modern comfort meets Rustic Charm
Ulster Park
9.8 out of 10, Exceptional, (20 reviews)
"Easy access and checkout, extremely clean, accurate pictures, comfy beds, well stocked kitchen. Great for groups. Would gladly stay again!"
United States
Emily F.
The price is CA $411
CA $1,154 total
includes taxes & fees
Oct 25 - Oct 26
Maple Ridge Modern Rustic Retreat where Modern comfort meets Rustic Charm
A hot tub on a wooden deck with a view of a river and trees.

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

Welcome to The Boathouse! Waterfront/Boats/Hot tub
New Paltz
9.6 out of 10, Exceptional, (12 reviews)
"We enjoyed our stay very much! Everything was as described, inside was very clean, host was excellent with communication. Scenic, serene spot!"
United States
Jessica B.
The price is CA $354
CA $586 total
includes taxes & fees
Nov 5 - Nov 6
Welcome to The Boathouse! Waterfront/Boats/Hot tub
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.

11. 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)
"Great property in a serene setting. We enjoyed it very much!"
United States
John M.
The price is CA $159
CA $384 total
includes taxes & fees
Oct 20 - Oct 21
The Studio at the Inn at High Falls
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, (80 reviews)
"It’s was nice, clean and the outdoor out area was really nice."
United States
Roger S.
The price is CA $389
CA $515 total
includes taxes & fees
Oct 28 - Oct 29
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
A large wooden dining table surrounded by chairs, with a stone fireplace and large windows in the background.

13. The George is an elegant restored home in the Hudson Valley

The George is an elegant restored home in the Hudson Valley
Stanfordville
9.8 out of 10, Exceptional, (12 reviews)
"Clean, comfortable, private, and plenty of room. Hosts went above and beyond to make our stay easy and memorable."
United States
Polly J.
The price is CA $1,018
CA $1,563 total
includes taxes & fees
Oct 19 - Oct 20
The George is an elegant restored home in the Hudson Valley
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, (106 reviews)
"Wonderful stay. Lovely tiny house in a beautiful wooded setting. Woke to the sounds of birds singing. Would stay again"
United States
Nan
The price is CA $222
CA $350 total
includes taxes & fees
Nov 9 - Nov 10
Esopus Creek modern Tiny house Retreat in Woodstock &Kingston Catskill area!
A modern living room with a sofa, a coffee table, and a dining table. There are two doors, one black and one white, and a window with blinds.

15. Hot Tub - Hammock- Games - Grill - Large Colonial

Hot Tub - Hammock- Games - Grill - Large Colonial
Kingston
10.0 out of 10, Exceptional, (12 reviews)
"We had a great stay! Great location and was clean and comfortable for all of our friends."
United States
Amanda R.
The price is CA $326
CA $761 total
includes taxes & fees
Oct 20 - Oct 21
Hot Tub - Hammock- Games - Grill - Large Colonial
A wooden deck with a wood-burning stove and a door leading to an outdoor area with chairs.

16. 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, (5 reviews)
"Great tastefully kept property. Our family including the 8 year felt we should have stayed here longer."
United States
Tarun
The price is CA $245
CA $441 total
includes taxes & fees
Nov 1 - Nov 2
Historic Hudson Valley Farmhouse w/ Sauna in Stone Ridge Hamlet
A kitchen with grey cabinets, a stone floor, and a view of a garden through an open door.

17. 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 CA $216
CA $716 total
includes taxes & fees
Nov 18 - Nov 19
Historic Cottage * Steam Shower * Chef’s Kitchen
A bedroom with a large bed, multiple windows, a ceiling fan, and a view of trees.

18. The New Paltz Moondance Ridge

The New Paltz Moondance Ridge
New Paltz
The price is CA $2,721
CA $3,974 total
includes taxes & fees
Oct 29 - Oct 30
The New Paltz Moondance Ridge
A living room with a sofa, a coffee table, a wooden chair, a striped rug, and a wall-mounted wreath.

19. The DeVita House Est. 1900

The DeVita House Est. 1900
Gardiner
10.0 out of 10, Exceptional, (42 reviews)
"Great house, well equipped, very accommodating hosts!"
United States
Christopher T.
The price is CA $212
CA $630 total
includes taxes & fees
Oct 26 - Oct 27
The DeVita House Est. 1900
A kitchen with wooden cabinets, a black countertop, a sink, and a window with a view of trees.

20. "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 CA $283
CA $822 total
includes taxes & fees
Oct 21 - Oct 22
"Country outside the city " 3 bedrooms 2 full bathrooms
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

Holiday Inn Express Poughkeepsie by IHG

Holiday Inn Express Poughkeepsie by IHG

8/10 Good
"Definitely book ahead for better rates and to get your room of choice"
Anthony 1-night trip
Posted less than an hour ago
Holiday Inn Express Poughkeepsie by IHG

Find out more about Pleasant Valley

Pleasant Valley Vacation Homes information

Number of reviews
425
Accommodation
376 Vacation Homes
Lowest Price
CA $183
Highest Price
CA $3,974

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