A rustic barn surrounded by autumn foliage on a hillside.

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Check prices for these dates

In two weeks
23 Oct - 25 Oct
In two months
4 Dec - 6 Dec
In three months
1 Jan - 3 Jan
In four months
29 Jan - 31 Jan

Our top choices for Pine Plains vacation 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.
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)
"We loved the house and it really added to our upstate experience!!"
United States
stephen r.
The price is AED 2,920
AED 4,961 total
includes taxes & fees
16 Oct - 17 Oct
A Country Lodge Straight Out of the Pages of a Great Novel
A living room with a television, a cabinet, a glass coffee table, and a framed picture on the wall.

3. Chic Lakeside Oasis|Near Rhinebeck & Millbrook

Chic Lakeside Oasis|Near Rhinebeck & Millbrook
Stanfordville
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 AED 2,645
AED 4,076 total
includes taxes & fees
18 Oct - 19 Oct
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 AED 375
AED 1,053 total
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, (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 AED 253
AED 909 total
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 AED 345
AED 1,144 total
includes taxes & fees
2 Nov - 3 Nov
Retro Retreat: renovated 2BR, desk, no chore list!
A sectional sofa with matching ottomans, a small table with a lamp, and a patterned rug on a wooden floor.

8. 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 AED 496
AED 1,275 total
includes taxes & fees
27 Oct - 28 Oct
Country House offers 2 bedrooms and a den, lots of parking.
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.

9. 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, (3 reviews)
"Very comfortable accommodation, beds and pillows are wonderful!"
United States
Danita K.
Hot Tub; Big Kitchen; 2 Blocks to Downtown Saugerties
A dining area with a chandelier, wooden chairs, a table, and a view through a glass door.

10. 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 AED 566
AED 2,314 total
includes taxes & fees
3 Nov - 4 Nov
Creek Views * Chef’s Kitchen * Walk To Lighthouse
A kitchen with a stove, cabinets, and a microwave.

11. 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 AED 209
AED 831 total
includes taxes & fees
2 Nov - 3 Nov
Butterfly Bungalow Studio · Saugerties/Woodstock
A room with a dark blue wall, two wooden chairs with yellow cushions, a round wooden table, and three framed botanical illustrations.

12. Butterfly and Sage: 2 Studios, Shared Yard

Butterfly and Sage: 2 Studios, Shared Yard
Saugerties
The price is AED 331
AED 1,427 total
includes taxes & fees
2 Nov - 3 Nov
Butterfly and Sage: 2 Studios, Shared Yard
A modern kitchen with a gas stove, white cabinets, a microwave, and a decorative wall piece.

13. 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 AED 217
AED 839 total
includes taxes & fees
2 Nov - 3 Nov
Sage Sojourn Studio · Saugerties/Woodstock
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 AED 390
AED 519 total
includes taxes & fees
7 Oct - 8 Oct
All the comforts of home
A white building with a sign reading "Elm Drive 43".

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, (6 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 AED 1,469
AED 3,087 total
includes taxes & fees
11 Oct - 12 Oct
Steps to the Delightful Village of Millbrook ☆ Fun Family Getaway
An outdoor seating area with wicker furniture and a glass table, surrounded by lush greenery.

16. 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 AED 684
AED 1,610 total
includes taxes & fees
1 Nov - 2 Nov
Cheerful 3-bedroom cottage with woodstove
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 AED 764
AED 1,801 total
includes taxes & fees
26 Oct - 27 Oct
3BR Farmhouse in the Village of Saugerties - Hike Upstate - Walk to it all!
A hot tub with a view of a lake and a dock.

18. 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, (7 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 AED 1,226
AED 3,343 total
includes taxes & fees
6 Oct - 7 Oct
Hot tub on water, 5min HITS, 20mi to Hunter skiing
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 AED 580
AED 1,087 total
includes taxes & fees
7 Oct - 8 Oct
Cabin Oasis near Town
A wooden deck leading to a cabin with a window and a door, surrounded by trees.

20. Modern cabin retreat

Modern cabin retreat
Catskill
The price is AED 536
AED 1,016 total
includes taxes & fees
6 Oct - 7 Oct
Modern cabin retreat
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

Prospect Berkshires

Prospect Berkshires

10/10 Excellent
"Absolutely spectacular resort! Could not have enjoyed more."
Alexis 1-night trip
Posted 6 hours ago
Prospect Berkshires