A rustic barn surrounded by autumn foliage on a hillside.

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Check prices for these dates

In two weeks
11 Sept - 13 Sept
In two months
23 Oct - 25 Oct
In three months
20 Nov - 22 Nov
In four months
18 Dec - 20 Dec

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. 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 £564
includes taxes & fees
22 Sept - 23 Sept
NEW: Chic Modern Barn Style Home in Fun Area
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 £1,063
includes taxes & fees
7 Sept - 8 Sept
A Country Lodge Straight Out of the Pages of a Great Novel
A rustic interior with wooden beams, multiple windows, and a kitchen area with dishes and a coffee maker.

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 £256
includes taxes & fees
30 Aug - 31 Aug
rural, serene + sophisticated space

4. Chic Lakeside Oasis|Near Rhinebeck & Millbrook

Chic Lakeside Oasis|Near Rhinebeck & Millbrook
Stanfordville
The price is £502
includes taxes & fees
9 Sept - 10 Sept
Chic Lakeside Oasis|Near Rhinebeck & Millbrook
A compact kitchen with blue cabinets, a white stove, and yellow chairs.

5. 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 £185
includes taxes & fees
9 Sept - 10 Sept
Retro Retreat: 1br home w/ WFH desk, livingroom, fire pit and no chores!
A large wooden dining table surrounded by chairs, with a stone fireplace and large windows in the background.

6. 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, (8 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 £814
includes taxes & fees
9 Sept - 10 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.

7. Campfire Cottage: Fireplace, fire pit & no chores!

Campfire Cottage: Fireplace, fire pit & no chores!
Kingston
10.0 out of 10, Exceptional, (33 reviews)
"The place was amazing! Very easy check in/out process and the host is very responsive. "
United States
Samuel M.
The price is £200
includes taxes & fees
23 Sept - 24 Sept
Campfire Cottage: Fireplace, fire pit & no chores!
A neatly made bed with white bedding and a few colorful pillows, a wooden headboard, and a wall-mounted light fixture.

8. 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 £245
includes taxes & fees
15 Sept - 16 Sept
Retro Retreat: renovated 2BR, desk, no chore list!
A wooden deck with a staircase leading to a covered porch area.

9. All the comforts of home

All the comforts of home
Hudson
9.2 out of 10, Wonderful, (35 reviews)
"Great location and super welcoming "
United States
Julie B.
The price is £106
includes taxes & fees
9 Sept - 10 Sept
All the comforts of home

10. Soft Launch Deal: Butterfly Bungalow Studio

Soft Launch Deal: Butterfly Bungalow Studio
Saugerties
The price is £160
includes taxes & fees
2 Sept - 3 Sept
Soft Launch Deal: Butterfly Bungalow Studio

11. 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 £160
includes taxes & fees
2 Sept - 3 Sept
Soft Launch Deal: Sage Sojourn Studio
A view from a room with a sliding glass door leading to an outdoor deck with a wooden fence, a chair, and a bench.

12. 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, (99 reviews)
"Convenient and comfortable stay"
United States
Cathy G.
The price is £194
includes taxes & fees
31 Aug - 1 Sept
Esopus Creek modern Tiny house Retreat in Woodstock &Kingston Catskill area!
A dining area with a chandelier, wooden chairs, a table, and a view through a glass door.

13. 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 £492
includes taxes & fees
22 Sept - 23 Sept
Super Comfortable Water-view Home in Saugerties

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

Soft Launch Deal: Butterfly and Sage, Two Studios
Saugerties
The price is £284
includes taxes & fees
2 Sept - 3 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.

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)
"We loved our stay here. It was a beautiful location and central to the places we wanted to visit. It looked brand new and it was very clean. It was quiet and peaceful. The hosts even had little snacks for us which was a nice touch."
United States
Laura M.
The price is £321
includes taxes & fees
9 Sept - 10 Sept
Peaceful Riverfront Cottage with Private Hot tub
A spacious kitchen with a central island, wooden flooring, and large windows.

16. Cozy Catskill Escape

Cozy Catskill Escape
Catskill
10.0 out of 10, Exceptional, (1 review)
"Inside the cabin was fantastic! Modern, clean, well stocked with essentials. We very much enjoyed our time in the cabin. The town was so charming and fun to explore. Was not expecting the auto/junk yard atmosphere on the outside. I understand why it wasn’t part of the description of the property. That being said, the neighbors did not bother us during our stay."
United States
Vicki M.
The price is £195
includes taxes & fees
15 Sept - 16 Sept
Cozy Catskill Escape
An outdoor seating area with wicker furniture and a glass table, surrounded by lush greenery.

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 £365
includes taxes & fees
22 Sept - 23 Sept
Cheerful 3-bedroom cottage with woodstove
A wooden deck leading to a cabin with a window and a door, surrounded by trees.

18. Modern cabin retreat

Modern cabin retreat
Catskill
The price is £210
includes taxes & fees
31 Aug - 1 Sept
Modern cabin retreat
A modern living space with a kitchen area, a dining table, and a sofa.

19. Cabin Oasis near Town

Cabin Oasis near Town
Catskill
The price is £221
includes taxes & fees
9 Sept - 10 Sept
Cabin Oasis near Town
A living room with a sofa, armchairs, a coffee table, and a TV stand.

20. Catskill Stay w/ Deck & Fire Pit

Catskill Stay w/ Deck & Fire Pit
Catskill
9.0 out of 10, Wonderful, (4 reviews)
"we had a great stay at this house with a group of friends - rooms were comfortable and kitchen had a lot of things we needed for meals. "
United States
raquel p.
The price is £320
includes taxes & fees
1 Sept - 2 Sept
Catskill Stay w/ Deck & Fire Pit
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

St. Charles Hotel

St. Charles Hotel

8/10 Good
"Place was clean. Bed was comfortable. Air conditioning was very loud!!"
Jacqueline 1-night trip
Posted 2 hours ago
St. Charles Hotel

Find out more about Pine Plains

Pine Plains Holiday Homes information

Number of reviews
291
Accommodation
553 Holiday Homes
Lowest Price
£106
Highest Price
£1,063