A rustic barn surrounded by autumn foliage on a hillside.

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Check prices for these dates

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

Our top choices for Pine Plains vacation homes

TV, fireplace, books

1. 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 AED 816
AED 2,530 total
includes taxes & fees
28 Oct - 29 Oct
Chic Barn Style * Fireplace * Near Stissing House
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)
"We loved the house and it really added to our upstate experience!!"
United States
stephen r.
The price is AED 3,269
AED 5,115 total
includes taxes & fees
6 Oct - 7 Oct
A Country Lodge Straight Out of the Pages of a Great Novel
Coffee/tea maker, fridge, microwave, oven

3. 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 AED 253
AED 880 total
includes taxes & fees
30 Sep - 1 Oct
Retro Retreat: 1br home w/ WFH desk, livingroom, fire pit and no chores!
Smart TV, foosball, books

4. Chic Lakeside Oasis|Near Rhinebeck & Millbrook

Chic Lakeside Oasis|Near Rhinebeck & Millbrook
Stanfordville
The price is AED 1,653
AED 2,402 total
includes taxes & fees
1 Oct - 2 Oct
Chic Lakeside Oasis|Near Rhinebeck & Millbrook
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, (10 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 AED 2,645
AED 3,856 total
includes taxes & fees
28 Sep - 29 Sep
The George is an elegant restored home in the Hudson Valley
Interior

6. 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 AED 316
AED 950 total
includes taxes & fees
28 Sep - 29 Sep
Campfire Cottage: Fireplace, fire pit & no chores!
Dining

7. Country House offers 2 bedrooms and a den, lots of parking.

Country House offers 2 bedrooms and a den, lots of parking.
Saugerties
The price is AED 496
AED 1,255 total
includes taxes & fees
28 Sep - 29 Sep
Country House offers 2 bedrooms and a den, lots of parking.
Interior

8. Catskill Cottage Walk to Downtown & River Views

Catskill Cottage Walk to Downtown & River Views
Catskill
10.0 out of 10, Exceptional, (30 reviews)
"Great little place to stay at right in downtown!!"
United States
Bryan S.
The price is AED 290
AED 613 total
includes taxes & fees
28 Sep - 29 Sep
Catskill Cottage Walk to Downtown & River Views
Coffee/tea maker, fridge, microwave, oven

9. Soft Launch Deal: Butterfly Bungalow Studio

Soft Launch Deal: Butterfly Bungalow Studio
Saugerties
10.0 out of 10, Exceptional, (1 review)
"Both the house and host were great. The house was in great shape, clean, comfy and with anything we might needed. 100% recommend!!"
United States
Matias
The price is AED 149
AED 763 total
includes taxes & fees
29 Sep - 30 Sep
Soft Launch Deal: Butterfly Bungalow Studio
Dining

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

Soft Launch Deal: Butterfly and Sage, Two Studios
Saugerties
The price is AED 417
AED 1,474 total
includes taxes & fees
25 Oct - 26 Oct
Soft Launch Deal: Butterfly and Sage, Two Studios
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, (103 reviews)
"Wonderful stay. "
United States
Chris L.
The price is AED 628
AED 950 total
includes taxes & fees
28 Sep - 29 Sep
Esopus Creek modern Tiny house Retreat in Woodstock &Kingston Catskill area!
Coffee/tea maker, fridge, microwave, oven

12. 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 AED 149
AED 763 total
includes taxes & fees
30 Sep - 1 Oct
Soft Launch Deal: Sage Sojourn Studio
Dining

13. Creek Views * Chef’s Kitchen * Walk To Lighthouse

Creek Views * Chef’s Kitchen * Walk To Lighthouse
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 AED 590
AED 2,250 total
includes taxes & fees
29 Sep - 30 Sep
Creek Views * Chef’s Kitchen * Walk To Lighthouse
Exterior

14. Modern cabin retreat

Modern cabin retreat
Catskill
The price is AED 536
AED 965 total
includes taxes & fees
5 Oct - 6 Oct
Modern cabin retreat
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 AED 878
AED 1,534 total
includes taxes & fees
28 Sep - 29 Sep
Peaceful Riverfront Cottage with Private Hot tub
Property grounds

16. All the comforts of home

All the comforts of home
Hudson
9.2 out of 10, Wonderful, (37 reviews)
"Great location and super welcoming "
United States
Julie B.
The price is AED 390
AED 519 total
includes taxes & fees
1 Oct - 2 Oct
All the comforts of home
2 bedrooms, desk, WiFi (free), bed sheets

17. 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
Retro Retreat: renovated 2BR, desk, no chore list!
Property grounds

18. Cheerful 3-bedroom cottage with woodstove

Cheerful 3-bedroom cottage with woodstove
Sheffield
10.0 out of 10, Exceptional, (45 reviews)
"The property was centrally located for skiing, and was a comfortable stay."
United States
Kelly R.
The price is AED 684
AED 1,519 total
includes taxes & fees
12 Oct - 13 Oct
Cheerful 3-bedroom cottage with woodstove
Terrace/patio

19. 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 AED 1,099
AED 3,559 total
includes taxes & fees
28 Sep - 29 Sep
Chic Waterfront w/ Hot Tub, Sauna and Sky Deck!
Coffee/tea maker, fridge, microwave, oven

20. Catskill * Screened Porch * Chef’s Kitchen

Catskill * Screened Porch * Chef’s Kitchen
Catskill
10.0 out of 10, Exceptional, (1 review)
"As described."
United States
kimberly j.
The price is AED 582
AED 2,454 total
includes taxes & fees
29 Sep - 30 Sep
Catskill * Screened Porch * Chef’s Kitchen
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
"The bartender she is excellent"
vera alice 1-night trip
Posted 17 hours ago
Beekman Arms and Delamater Inn