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
13 Nov - 15 Nov
In two months
25 Dec - 27 Dec
In three months
22 Jan - 24 Jan
In four months
19 Feb - 21 Feb

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)
"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 NZ$1,190
includes taxes & fees
17 Nov - 18 Nov
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)
"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 NZ$2,475
includes taxes & fees
31 Oct - 1 Nov
A Country Lodge Straight Out of the Pages of a Great Novel
A large wooden dining table surrounded by chairs, with a stone fireplace and large windows in the background.

3. 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, (13 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 NZ$2,170
includes taxes & fees
9 Nov - 10 Nov
The George is an elegant restored home in the Hudson Valley
A covered outdoor deck with wicker furniture, a grill, and a view of a lake.

4. Chic Lakeside Oasis|Near Rhinebeck & Millbrook

Chic Lakeside Oasis|Near Rhinebeck & Millbrook
Stanfordville
The price is NZ$1,193
includes taxes & fees
2 Nov - 3 Nov
Chic Lakeside Oasis|Near Rhinebeck & Millbrook
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 NZ$442
includes taxes & fees
28 Oct - 29 Oct
Campfire Cottage: Fireplace, fire pit & no chores!
A compact kitchen with blue cabinets, a white stove, and yellow chairs.

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!"
United States
Brendan B.
The price is NZ$445
includes taxes & fees
2 Nov - 3 Nov
Retro Retreat: 1br home w/ WFH desk, livingroom, fire pit and no chores!
A neatly made bed with white bedding and a few colorful pillows, a wooden headboard, and a wall-mounted light fixture.

7. 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 NZ$525
includes taxes & fees
18 Nov - 19 Nov
Retro Retreat: renovated 2BR, desk, no chore list!
A living room with a white armchair, a grey sofa, a large green plant, and a wooden coffee table. A staircase with white railings leads to an upper floor.

8. 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 NZ$906
includes taxes & fees
28 Oct - 29 Oct
Hot Tub; Big Kitchen; 2 Blocks to Downtown Saugerties
A kitchen with a stove, cabinets, and a microwave.

9. Butterfly Bungalow Studio · Saugerties/Woodstock

Butterfly Bungalow Studio · Saugerties/Woodstock
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 NZ$406
includes taxes & fees
2 Nov - 3 Nov
Butterfly Bungalow Studio · Saugerties/Woodstock
A kitchen with a white refrigerator, a wooden table, a green chair, and a wall-mounted TV.

10. 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 NZ$384
includes taxes & fees
28 Oct - 29 Oct
Sage Sojourn Studio · Saugerties/Woodstock
A wooden deck with a staircase leading to a covered porch area.

11. 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 NZ$248
includes taxes & fees
9 Nov - 10 Nov
All the comforts of home
A dining area with a chandelier, wooden chairs, a table, and a view through a glass door.

12. 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 NZ$1,109
includes taxes & fees
28 Oct - 29 Oct
Creek Views * Chef’s Kitchen * Walk To Lighthouse
A room with a dining table, two chairs, a window with curtains, a wall-mounted air conditioner, and framed botanical prints.

13. Butterfly and Sage: 2 Studios, Shared Yard

Butterfly and Sage: 2 Studios, Shared Yard
Saugerties
The price is NZ$690
includes taxes & fees
1 Nov - 2 Nov
Butterfly and Sage: 2 Studios, Shared Yard
A spacious living room with a large wooden dining table, a comfortable sofa, and a bookshelf filled with books and decorative items.

14. 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, (7 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 NZ$1,435
includes taxes & fees
2 Nov - 3 Nov
Steps to the Delightful Village of Millbrook ☆ Fun Family Getaway
A hot tub with a view of a lake and a dock.

15. 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 NZ$1,388
includes taxes & fees
2 Nov - 3 Nov
Hot tub on water, 5min HITS, 20mi to Hunter skiing
A modern kitchen with dark cabinets, a wooden island, stainless steel appliances, and a large window.

16. Peaceful Riverfront Cottage with Private Hot tub

Peaceful Riverfront Cottage with Private Hot tub
Lake Katrine
10.0 out of 10, Exceptional, (17 reviews)
"A nice relaxing spot."
United States
Darren F.
The price is NZ$700
includes taxes & fees
28 Oct - 29 Oct
Peaceful Riverfront Cottage with Private Hot tub
A staircase with a metal handrail and a bench with a striped cushion.

17. 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 NZ$866
includes taxes & fees
3 Nov - 4 Nov
3BR Farmhouse in the Village of Saugerties - Hike Upstate - Walk to it all!
A view from a room with a sliding glass door leading to an outdoor deck with a wooden fence, a chair, and a bench.

18. 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, (109 reviews)
"Wonderful stay. Lovely tiny house in a beautiful wooded setting. Woke to the sounds of birds singing. Would stay again"
United States
Nan
The price is NZ$431
includes taxes & fees
9 Nov - 10 Nov
Esopus Creek modern Tiny house Retreat in Woodstock &Kingston Catskill area!
An outdoor seating area with wicker furniture and a glass table, surrounded by lush greenery.

19. 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 NZ$726
includes taxes & fees
2 Nov - 3 Nov
Cheerful 3-bedroom cottage with woodstove
A living room with a grey sofa, patterned cushions, a side table with a lamp, and large windows offering a view of a snowy landscape.

20. Escape to a stunning two-story home nestled on serene Esopus Creek in Saugerties

Escape to a stunning two-story home nestled on serene Esopus Creek in Saugerties
Saugerties
10.0 out of 10, Exceptional, (3 reviews)
"Lovely, clean, quiet house. Exactly what we needed for a place to stay while we were showing at HITS. Would definitely stay here again!"
United States
Charlotte J.
The price is NZ$1,051
includes taxes & fees
1 Nov - 2 Nov
Escape to a stunning two-story home nestled on serene Esopus Creek in Saugerties
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

Quality Inn Great Barrington

Quality Inn Great Barrington

10/10 Excellent
"Room was clean and comfortably appointed. Parking was not an issue even though the hotel was full. Easy walking to restaurants and shops. Staff were very pleasant and welcoming."
Janice 1-night trip
Posted 15 hours ago
Quality Inn Great Barrington

Find out more about Pine Plains

Pine Plains Holiday Homes information

Number of reviews
327
Accommodation
546 Holiday Homes
Lowest Price
NZ$248
Highest Price
NZ$2,475