A rustic barn surrounded by autumn foliage on a hillside.

Holiday Homes in Pine Plains

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Check prices for these dates

In two weeks
25 Sept - 27 Sept
In two months
6 Nov - 8 Nov
In three months
4 Dec - 6 Dec
In four months
1 Jan - 3 Jan

Our top choices for Pine Plains holiday homes

TV, fireplace, books

1. NEW: Chic Modern Barn Style Home in Fun Area

NEW: Chic Modern Barn Style Home in Fun Area
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 NZ$1,169
includes taxes & fees
22 Sept - 23 Sept
NEW: Chic Modern Barn Style Home in Fun Area
Coffee/tea maker, fridge, microwave, oven

2. A Country Lodge Straight Out of the Pages of a Great Novel

A Country Lodge Straight Out of the Pages of a Great Novel
Pine Plains
10.0 out of 10, Exceptional, (15 reviews)
"Our group of parents and riders had a great stay during the Millbrook Horse Trials in July. Clean facility, ample room, responsive host. Would stay again."
United States
Hessie S.
The price is NZ$2,420
includes taxes & fees
23 Sept - 24 Sept
A Country Lodge Straight Out of the Pages of a Great Novel
Terrace/patio

3. Chic Lakeside Oasis|Near Rhinebeck & Millbrook

Chic Lakeside Oasis|Near Rhinebeck & Millbrook
Stanfordville
The price is NZ$1,183
includes taxes & fees
21 Sept - 22 Sept
Chic Lakeside Oasis|Near Rhinebeck & Millbrook
Interior

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 NZ$451
includes taxes & fees
13 Sept - 14 Sept
Campfire Cottage: Fireplace, fire pit & no chores!
Dining

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

The George is an elegant restored home in the Hudson Valley
Stanfordville
9.6 out of 10, Exceptional, (9 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 NZ$1,934
includes taxes & fees
22 Sept - 23 Sept
The George is an elegant restored home in the Hudson Valley
Coffee/tea maker, fridge, microwave, oven

6. 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 NZ$416
includes taxes & fees
23 Sept - 24 Sept
Retro Retreat: 1br home w/ WFH desk, livingroom, fire pit and no chores!
1 bedroom, free WiFi, bed sheets

7. Soft Launch Deal: Butterfly Bungalow Studio

Soft Launch Deal: Butterfly Bungalow Studio
Saugerties
The price is NZ$357
includes taxes & fees
14 Sept - 15 Sept
Soft Launch Deal: Butterfly Bungalow Studio
Dining

8. Super Comfortable Water-view Home in Saugerties

Super Comfortable Water-view Home in Saugerties
Saugerties
9.8 out of 10, Exceptional, (7 reviews)
"this house was very comfortable and convenient to Saugerties"
United States
molly f.
The price is NZ$1,162
includes taxes & fees
29 Sept - 30 Sept
Super Comfortable Water-view Home in Saugerties
2 bedrooms, desk, free WiFi, bed sheets

9. 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 NZ$558
includes taxes & fees
22 Sept - 23 Sept
Retro Retreat: renovated 2BR, desk, no chore list!
Fridge, oven, stovetop, dishwasher

10. Cozy Catskill Escape

Cozy Catskill Escape
Catskill
10.0 out of 10, Exceptional, (2 reviews)
"Very accommodating host. Great with last minute visits."
United States
Kevin P.
The price is NZ$454
includes taxes & fees
14 Sept - 15 Sept
Cozy Catskill Escape
Interior

11. 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, (100 reviews)
"Convenient and comfortable stay"
United States
Cathy G.
The price is NZ$457
includes taxes & fees
30 Sept - 1 Oct
Esopus Creek modern Tiny house Retreat in Woodstock &Kingston Catskill area!
Property grounds

12. All the comforts of home

All the comforts of home
Hudson
9.2 out of 10, Wonderful, (36 reviews)
"Great location and super welcoming "
United States
Julie B.
The price is NZ$243
includes taxes & fees
14 Sept - 15 Sept
All the comforts of home
Coffee/tea maker, fridge, microwave, oven

13. Soft Launch Deal: Sage Sojourn Studio

Soft Launch Deal: Sage Sojourn Studio
Saugerties
8.0 out of 10, Very good, (1 review)
"I had the pleasure of being the very first guest to stay at this property. The host was very helpful prior to booking providing extra details of the property since the outside area is not yet complete. The interior was very nice, everything was clean, exactly as pictured in the listing and the mini Nespresso machine was great. The location was perfect for people visiting Saugerties or Woodstock, both only a few minutes away. I visited for the night for a concert at Bearsville Theatre and it was...
United States
Cathy H.
The price is NZ$363
includes taxes & fees
22 Sept - 23 Sept
Soft Launch Deal: Sage Sojourn Studio
Coffee/tea maker, fridge, microwave, oven

14. Soft Launch Deal: Butterfly and Sage, Two Studios

Soft Launch Deal: Butterfly and Sage, Two Studios
Saugerties
The price is NZ$666
includes taxes & fees
23 Sept - 24 Sept
Soft Launch Deal: Butterfly and Sage, Two Studios
Outdoor spa tub

15. Peaceful Riverfront Cottage with Private Hot tub

Peaceful Riverfront Cottage with Private Hot tub
Lake Katrine
10.0 out of 10, Exceptional, (15 reviews)
"A nice relaxing spot."
United States
Darren F.
The price is NZ$767
includes taxes & fees
14 Sept - 15 Sept
Peaceful Riverfront Cottage with Private Hot tub
Exterior

16. Modern cabin retreat

Modern cabin retreat
Catskill
The price is NZ$464
includes taxes & fees
14 Sept - 15 Sept
Modern cabin retreat
Property grounds

17. Cheerful 3-bedroom cottage with woodstove

Cheerful 3-bedroom cottage with woodstove
Sheffield
10.0 out of 10, Exceptional, (43 reviews)
"The property was centrally located for skiing, and was a comfortable stay."
United States
Kelly R.
The price is NZ$739
includes taxes & fees
28 Sept - 29 Sept
Cheerful 3-bedroom cottage with woodstove
Smart TV

18. 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 NZ$925
includes taxes & fees
13 Sept - 14 Sept
Hot Tub - Hammock- Games - Grill - Large Colonial
Interior

19. 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 NZ$1,385
includes taxes & fees
20 Sept - 21 Sept
Steps to the Delightful Village of Millbrook ☆ Fun Family Getaway
Terrace/patio

20. Chic Waterfront w/ Hot Tub, Sauna and Sky Deck!

Chic Waterfront w/ Hot Tub, Sauna and Sky Deck!
Saugerties
10.0 out of 10, Exceptional, (18 reviews)
"Great stay! Would definitely go back!"
United States
Alexis
The price is NZ$1,544
includes taxes & fees
29 Sept - 30 Sept
Chic Waterfront w/ Hot Tub, Sauna and Sky Deck!
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 Pine Plains Hotel Reviews

Holiday Inn Express Hotel & Suites Great Barrington by IHG

Holiday Inn Express Hotel & Suites Great Barrington by IHG

10/10 Excellent
"Check-in was easy and the desk staff efficient. Breakfast was good as expected and breakfast area clean. Unusual to have to fill out a form the night in advance if you wanted the room cleaned or fresh towels. Great location with good dining options close by."
Ronald 2-night trip
Posted 8 hours ago
Holiday Inn Express Hotel & Suites Great Barrington by IHG

Find out more about Pine Plains

Pine Plains Holiday Homes information

Number of reviews
311
Accommodation
546 Holiday Homes
Lowest Price
NZ$243
Highest Price
NZ$2,420