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Our top choices for Pine Plains holiday homes
1. NEW: Chic Modern Barn Style Home in Fun Area
NEW: Chic Modern Barn Style Home in Fun AreaPine 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!"
Estefany G.
The price is AU$1,034
includes taxes & fees
9 Nov - 10 Nov
2. A Country Lodge Straight Out of the Pages of a Great Novel
A Country Lodge Straight Out of the Pages of a Great NovelPine 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!"
Marianne R.
The price is AU$1,973
includes taxes & fees
9 Nov - 10 Nov
3. rural, serene + sophisticated space
rural, serene + sophisticated spaceRed Hook
10.0 out of 10, Exceptional, (9 reviews)
"Beautiful property with unique accommodations in the Hudson Valley"
BRIAN PATRICK M.
The price is AU$558
includes taxes & fees
1 Dec - 2 Dec
4. The George is an elegant restored home in the Hudson Valley
The George is an elegant restored home in the Hudson ValleyStanfordville
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."
Polly J.
The price is AU$1,775
includes taxes & fees
9 Nov - 10 Nov
5. Chic Lakeside Oasis|Near Rhinebeck & Millbrook
Chic Lakeside Oasis|Near Rhinebeck & MillbrookStanfordville
The price is AU$956
includes taxes & fees
9 Nov - 10 Nov
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, (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!"
Brendan B.
The price is AU$351
includes taxes & fees
10 Nov - 11 Nov
7. 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. "
Jim R.
The price is AU$339
includes taxes & fees
18 Nov - 19 Nov
8. Butterfly Bungalow Studio · Saugerties/Woodstock
Butterfly Bungalow Studio · Saugerties/WoodstockSaugerties
10.0 out of 10, Exceptional, (2 reviews)
"Great location, had everything needed for a comfortable stay."
Michael W.
The price is AU$312
includes taxes & fees
9 Nov - 10 Nov
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! "
Kelley Marie
The price is AU$399
includes taxes & fees
18 Nov - 19 Nov
10. Creek Views * Chef’s Kitchen * Walk To Lighthouse
Creek Views * Chef’s Kitchen * Walk To LighthouseSaugerties
9.8 out of 10, Exceptional, (7 reviews)
"this house was very comfortable and convenient to Saugerties"
molly f.
The price is AU$988
includes taxes & fees
9 Nov - 10 Nov
11. Lockwood Manor: Autumn Escape on Six Private Acres with Heated Pool
Lockwood Manor: Autumn Escape on Six Private Acres with Heated PoolHillsdale
The price is AU$2,128
includes taxes & fees
15 Nov - 16 Nov
12. Hot Tub; Big Kitchen; 2 Blocks to Downtown Saugerties
Hot Tub; Big Kitchen; 2 Blocks to Downtown SaugertiesSaugerties
10.0 out of 10, Exceptional, (5 reviews)
"Very comfortable accommodation, beds and pillows are wonderful!"
Danita K.
The price is AU$706
includes taxes & fees
11 Nov - 12 Nov
13. Butterfly and Sage: 2 Studios, Shared Yard
Butterfly and Sage: 2 Studios, Shared YardSaugerties
The price is AU$571
includes taxes & fees
19 Nov - 20 Nov
14. Sage Sojourn Studio · Saugerties/Woodstock
Sage Sojourn Studio · Saugerties/WoodstockSaugerties
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...
Cathy H.
The price is AU$332
includes taxes & fees
7 Dec - 8 Dec
15. All the comforts of home
All the comforts of homeHudson
9.2 out of 10, Wonderful, (38 reviews)
"Great location and super welcoming "
Julie B.
The price is AU$195
includes taxes & fees
9 Nov - 10 Nov
16. Steps to the Delightful Village of Millbrook ☆ Fun Family Getaway
Steps to the Delightful Village of Millbrook ☆ Fun Family GetawayMillbrook
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!"
Beth E.
The price is AU$1,112
includes taxes & fees
12 Nov - 13 Nov
17. Hot tub on water, 5min HITS, 20mi to Hunter skiing
Hot tub on water, 5min HITS, 20mi to Hunter skiingMalden
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."
Penny R.
The price is AU$1,051
includes taxes & fees
16 Nov - 17 Nov
18. 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."
Kristen R.
The price is AU$693
includes taxes & fees
7 Dec - 8 Dec
19. Hudson Landing - Fireplace & Catskills Retreat
Hudson Landing - Fireplace & Catskills RetreatSaugerties
The price is AU$900
includes taxes & fees
11 Nov - 12 Nov
20. Cheerful 3-bedroom cottage with woodstove
Cheerful 3-bedroom cottage with woodstoveSheffield
10.0 out of 10, Exceptional, (46 reviews)
"The property was centrally located for skiing, and was a comfortable stay."
Kelly R.
The price is AU$588
includes taxes & fees
18 Nov - 19 Nov
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.
Learn more about Pine Plains
Hike the trails of Stissing Mountain for panoramic views of this charming Hudson Valley town and its surrounding countryside. Spend afternoons exploring local farm stands or enjoying the peaceful waters of Stissing Lake with a picnic from Main Street businesses.
