A rustic barn surrounded by autumn foliage on a hillside.

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Our top choices for Pine Plains vacation homes

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 ¥23,794
¥94,436 total
includes taxes & fees
Nov 4 - Nov 5
Chic Barn Style * Fireplace * Near Stissing House

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)
"Stayed with a group for Millbrook Horse Trials, we had an amazing weekend at this calm and relaxing home with plenty of beds and amenities! What a treat!"
United States
Marianne R.
The price is ¥140,228
¥220,662 total
includes taxes & fees
Nov 15 - Nov 16
A Country Lodge Straight Out of the Pages of a Great Novel

3. rural, serene + sophisticated space

rural, serene + sophisticated space
Red Hook
10.0 out of 10, Exceptional, (9 reviews)
"Beautiful property with unique accommodations in the Hudson Valley"
United States
BRIAN PATRICK M.
The price is ¥50,367
¥60,832 total
includes taxes & fees
Dec 1 - Dec 2
rural, serene + sophisticated space

4. 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, (14 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 ¥139,259
¥200,047 total
includes taxes & fees
Nov 5 - Nov 6
The George is an elegant restored home in the Hudson Valley

5. Chic Lakeside Oasis|Near Rhinebeck & Millbrook

Chic Lakeside Oasis|Near Rhinebeck & Millbrook
Stanfordville
The price is ¥71,051
¥102,883 total
includes taxes & fees
Nov 4 - Nov 5
Chic Lakeside Oasis|Near Rhinebeck & Millbrook

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 ¥12,000
¥38,374 total
includes taxes & fees
Nov 17 - Nov 18
Campfire Cottage: Fireplace, fire pit & no chores!

7. 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, (7 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 ¥11,842
¥38,197 total
includes taxes & fees
Nov 4 - Nov 5
Retro Retreat: 1br home w/ WFH desk, livingroom, fire pit and no chores!

8. 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 ¥22,057
¥92,313 total
includes taxes & fees
Nov 30 - Dec 1
Creek Views * Chef’s Kitchen * Walk To Lighthouse

9. Butterfly Bungalow Studio · Saugerties/Woodstock

Butterfly Bungalow Studio · Saugerties/Woodstock
Saugerties
10.0 out of 10, Exceptional, (2 reviews)
"Great location, had everything needed for a comfortable stay."
United States
Michael W.
The price is ¥7,895
¥33,423 total
includes taxes & fees
Nov 4 - Nov 5
Butterfly Bungalow Studio · Saugerties/Woodstock

10. 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 ¥13,579
¥44,917 total
includes taxes & fees
Nov 17 - Nov 18
Retro Retreat: renovated 2BR, desk, no chore list!

11. Sage Sojourn Studio · Saugerties/Woodstock

Sage Sojourn Studio · Saugerties/Woodstock
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 ¥9,158
¥35,014 total
includes taxes & fees
Nov 17 - Nov 18
Sage Sojourn Studio · Saugerties/Woodstock

12. Butterfly and Sage: 2 Studios, Shared Yard

Butterfly and Sage: 2 Studios, Shared Yard
Saugerties
The price is ¥15,773
¥60,109 total
includes taxes & fees
Nov 4 - Nov 5
Butterfly and Sage: 2 Studios, Shared Yard

13. Hot Tub; Big Kitchen; 2 Blocks to Downtown Saugerties

Hot Tub; Big Kitchen; 2 Blocks to Downtown Saugerties
Saugerties
10.0 out of 10, Exceptional, (5 reviews)
"Very comfortable accommodation, beds and pillows are wonderful!"
United States
Danita K.
The price is ¥24,067
¥79,300 total
includes taxes & fees
Nov 8 - Nov 9
Hot Tub; Big Kitchen; 2 Blocks to Downtown Saugerties

14. All the comforts of home

All the comforts of home
Hudson
9.2 out of 10, Wonderful, (38 reviews)
"No frills, very clean and peaceful, beautiful setting"
United States
Lori M.
The price is ¥16,768
¥20,903 total
includes taxes & fees
Nov 4 - Nov 5
All the comforts of home

15. 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, (8 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 ¥63,156
¥126,102 total
includes taxes & fees
Nov 8 - Nov 9
Steps to the Delightful Village of Millbrook ☆ Fun Family Getaway

16. 3BR Farmhouse in the Village of Saugerties - Hike Upstate - Walk to it all!

3BR Farmhouse in the Village of Saugerties - Hike Upstate - Walk to it all!
Saugerties
10.0 out of 10, Exceptional, (3 reviews)
"Great location, very well-stocked. Would absolutely stay here again."
United States
Kristen R.
The price is ¥34,321
¥76,103 total
includes taxes & fees
Nov 10 - Nov 11
3BR Farmhouse in the Village of Saugerties - Hike Upstate - Walk to it all!

17. Hot tub on water, 5min HITS, 20mi to Hunter skiing

Hot tub on water, 5min HITS, 20mi to Hunter skiing
Malden
10.0 out of 10, Exceptional, (8 reviews)
"The house was very comfortable and clean. Kitchen was well appointed. Drawers and cabinets are well stocked w general utensils."
United States
Penny R.
The price is ¥41,536
¥123,148 total
includes taxes & fees
Nov 16 - Nov 17
Hot tub on water, 5min HITS, 20mi to Hunter skiing

18. Private Catskills Waterfront Mountain Views• Hot Tub • Sauna • Kayaks • Fire Pit

Private Catskills Waterfront Mountain Views• Hot Tub • Sauna • Kayaks • Fire Pit
Saugerties
9.8 out of 10, Exceptional, (16 reviews)
"This place was perfect for our family of 10 in town for a wedding. Walkable to town. Comfortable, spotless and spacious with fun touches like retro video games, kayaks and outdoor space. Host was responsive and helpful. Would definitely return!"
United States
Kate s.
The price is ¥138,683
¥223,936 total
includes taxes & fees
Nov 4 - Nov 5
Private Catskills Waterfront Mountain Views• Hot Tub • Sauna • Kayaks • Fire Pit

19. Modern cabin retreat

Modern cabin retreat
Catskill
The price is ¥20,849
¥38,918 total
includes taxes & fees
Nov 4 - Nov 5
Modern cabin retreat

20. Cheerful 3-bedroom cottage with woodstove

Cheerful 3-bedroom cottage with woodstove
Sheffield
10.0 out of 10, Exceptional, (46 reviews)
"The property was centrally located for skiing, and was a comfortable stay."
United States
Kelly R.
The price is ¥27,935
¥64,116 total
includes taxes & fees
Nov 23 - Nov 24
Cheerful 3-bedroom cottage with woodstove
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

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Pine Plains Vacation Homes information

Number of reviews
227
Accommodation
546 Vacation Homes
Lowest Price
¥20,903
Highest Price
¥223,936