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
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 holiday homes

A modern living room with a grey sofa, a wooden coffee table, and a staircase leading to an upper floor.

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)
The price is €582
includes taxes & fees
29 Sept - 30 Sept
Chic Barn Style * Fireplace * Near Stissing House
A modern kitchen with white cabinets, a large island, and a skylight.

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 €1,182
includes taxes & fees
16 Oct - 17 Oct
A Country Lodge Straight Out of the Pages of a Great Novel
A covered outdoor deck with a grill, a chair, and a view of a lake and forest.

3. Chic Lakeside Oasis|Near Rhinebeck & Millbrook

Chic Lakeside Oasis|Near Rhinebeck & Millbrook
Stanfordville
The price is €599
includes taxes & fees
1 Oct - 2 Oct
Chic Lakeside Oasis|Near Rhinebeck & Millbrook
A large wooden dining table surrounded by chairs, with a stone fireplace and large windows in the background.

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

The George is an elegant restored home in the Hudson Valley
Stanfordville
9.6 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 €974
includes taxes & fees
25 Sept - 26 Sept
The George is an elegant restored home in the Hudson Valley
A modern kitchen with a granite countertop, stainless steel appliances, and a built-in oven.

5. 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 €243
includes taxes & fees
28 Sept - 29 Sept
Campfire Cottage: Fireplace, fire pit & no chores!
A modern interior with a staircase, wooden flooring, a dining area, and a brick wall.

6. 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 €151
includes taxes & fees
28 Sept - 29 Sept
Catskill Cottage Walk to Downtown & River Views
A compact kitchen with blue cabinets, a white stove, and yellow chairs.

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, (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 €237
includes taxes & fees
14 Oct - 15 Oct
Retro Retreat: 1br home w/ WFH desk, livingroom, fire pit and no chores!
A view from a room with a sliding glass door leading to an outdoor deck with a wooden fence, a chair, and a bench.

8. 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, (101 reviews)
"Wonderful stay. "
United States
Chris L.
The price is €241
includes taxes & fees
27 Sept - 28 Sept
Esopus Creek modern Tiny house Retreat in Woodstock &Kingston Catskill area!
A two-story house with a front porch, surrounded by lush greenery and trees.

9. Perfect House In Hillsdale, Brings Friends & Fam

Perfect House In Hillsdale, Brings Friends & Fam
Hillsdale
8.4 out of 10, Very good, (5 reviews)
"Overall a very pleasant stay. It is a cool old house with all its charm and quirks. Very spacious, comfortable. Decent kitchen. Location very accessible for mountains and tooling around. Just right for a getaway"
United States
Annetta D.
The price is €462
includes taxes & fees
27 Sept - 28 Sept
Perfect House In Hillsdale, Brings Friends & Fam
An outdoor seating area with wicker furniture and a glass table, surrounded by lush greenery.

10. 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 €416
includes taxes & fees
7 Oct - 8 Oct
Cheerful 3-bedroom cottage with woodstove
A bedroom with a bed, a dresser, a vintage-style radio, and a wall-mounted TV.

11. 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 €186
includes taxes & fees
29 Sept - 30 Sept
Soft Launch Deal: Butterfly Bungalow Studio
A modern kitchen with a central island, wooden beams, and a view to the outdoors.

12. Home in Great Barrington

Home in Great Barrington
Great Barrington
9.8 out of 10, Exceptional, (39 reviews)
"Perfect location to walk into town - clean, light, airy and neat space. Enjoyable visit!"
United States
HEATHER G.
The price is €301
includes taxes & fees
27 Sept - 28 Sept
Home in Great Barrington
A kitchen with a gas stove, a sink, a coffee maker, a toaster, and a microwave.

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.
Soft Launch Deal: Sage Sojourn Studio
A wooden deck with a staircase leading to a covered porch area.

14. 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 €128
includes taxes & fees
1 Oct - 2 Oct
All the comforts of home
A kitchen with a gas stove, a coffee maker, and a vintage radio.

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

Soft Launch Deal: Butterfly and Sage, Two Studios
Saugerties
The price is €332
includes taxes & fees
27 Sept - 28 Sept
Soft Launch Deal: Butterfly and Sage, Two Studios
A hot tub in a natural setting with a tree and a body of water in the background.

16. 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.
Peaceful Riverfront Cottage with Private Hot tub
A kitchen with a central island, bar stools, and pendant lighting.

17. 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 €237
includes taxes & fees
28 Sept - 29 Sept
Cozy Catskill Escape
A single-story house with a porch, a chimney, and a clear sky.

18. 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 €304
includes taxes & fees
1 Oct - 2 Oct
Country House offers 2 bedrooms and a den, lots of parking.
A dining area with a chandelier, wooden chairs, a table, and a view through a glass door.

19. 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 €543
includes taxes & fees
29 Sept - 30 Sept
Creek Views * Chef’s Kitchen * Walk To Lighthouse
A neatly made bed with white bedding and a few colorful pillows, a wooden headboard, and a wall-mounted light fixture.

20. 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 €315
includes taxes & fees
21 Oct - 22 Oct
Retro Retreat: renovated 2BR, desk, no chore list!
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

Hampton Inn Kingston

Hampton Inn Kingston

10/10 Excellent
"Excellent property. Clean and nice rooms and pool. Really nice breakfast and coffee areas. Nice staff"
Richard 1-night trip
Posted 11 hours ago
Hampton Inn Kingston

Find out more about Pine Plains

Pine Plains Holiday Homes information

Number of reviews
362
Accommodation
466 Holiday Homes
Lowest Price
€128
Highest Price
€1,182