A rustic barn surrounded by autumn foliage on a hillside.

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Check prices for these dates

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

Our top choices for Pine Plains vacation homes

Living area

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 ￥28,502
￥103,836 total
includes taxes & fees
Sep 22 - Sep 23
NEW: Chic Modern Barn Style Home in Fun Area
Private kitchen

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 ￥136,455
￥225,825 total
includes taxes & fees
Sep 13 - Sep 14
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 ￥68,994
￥104,587 total
includes taxes & fees
Sep 17 - Sep 18
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 ￥12,572
￥40,182 total
includes taxes & fees
Sep 13 - Sep 14
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 ￥110,390
￥164,598 total
includes taxes & fees
Sep 23 - Sep 24
The George is an elegant restored home in the Hudson Valley
Private kitchen

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 ￥10,579
￥37,950 total
includes taxes & fees
Sep 23 - Sep 24
Retro Retreat: 1br home w/ WFH desk, livingroom, fire pit and no chores!
Room

7. Soft Launch Deal: Butterfly Bungalow Studio

Soft Launch Deal: Butterfly Bungalow Studio
Saugerties
The price is ￥6,209
￥32,368 total
includes taxes & fees
Sep 14 - Sep 15
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)
"Very comfortable home, everything that’s needed is there "
United States
gianni g.
The price is ￥26,141
￥100,069 total
includes taxes & fees
Sep 14 - Sep 15
Super Comfortable Water-view Home in Saugerties
Room

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 ￥16,674
￥50,665 total
includes taxes & fees
Sep 22 - Sep 23
Retro Retreat: renovated 2BR, desk, no chore list!
Private kitchen

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 ￥18,705
￥40,182 total
includes taxes & fees
Sep 13 - Sep 14
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 ￥26,218
￥41,213 total
includes taxes & fees
Sep 14 - Sep 15
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 ￥16,283
￥21,672 total
includes taxes & fees
Sep 14 - Sep 15
All the comforts of home
Private kitchen

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 ￥6,531
￥33,078 total
includes taxes & fees
Sep 22 - Sep 23
Soft Launch Deal: Sage Sojourn Studio
Private kitchen

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

Soft Launch Deal: Butterfly and Sage, Two Studios
Saugerties
The price is ￥12,419
￥60,102 total
includes taxes & fees
Sep 20 - Sep 21
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 ￥36,636
￥67,650 total
includes taxes & fees
Sep 13 - Sep 14
Peaceful Riverfront Cottage with Private Hot tub
Exterior

16. Modern cabin retreat

Modern cabin retreat
Catskill
The price is ￥21,460
￥41,463 total
includes taxes & fees
Sep 14 - Sep 15
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 ￥27,184
￥63,076 total
includes taxes & fees
Sep 28 - Sep 29
Cheerful 3-bedroom cottage with woodstove
Living area

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 ￥35,319
￥81,455 total
includes taxes & fees
Sep 13 - Sep 14
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 ￥61,328
￥128,522 total
includes taxes & fees
Sep 17 - Sep 18
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 ￥36,092
￥141,754 total
includes taxes & fees
Sep 29 - Sep 30
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

Beekman Arms and Delamater Inn

Beekman Arms and Delamater Inn

10/10 Excellent
"My husband and I enjoyed our brief one nights stay at the Beekman arms. Our room was spacious and clean. The hotel was in a great location, very walkable. The included breakfast was just what we needed to start our day of activities. Thank you."
Barb 1-night trip
Posted 6 hours ago
Beekman Arms and Delamater Inn

Find out more about Pine Plains

Pine Plains Vacation Homes information

Number of reviews
311
Accommodation
546 Vacation Homes
Lowest Price
￥21,672
Highest Price
￥225,825