A rustic barn surrounded by autumn foliage on a hillside.

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Check prices for these dates

In two weeks
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 Feb

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.
The price is AED 1,337
AED 3,403 total
includes taxes & fees
11 Nov - 12 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)
"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 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, (12 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 4,105 total
includes taxes & fees
24 Oct - 25 Oct
The George is an elegant restored home in the Hudson Valley
A living room with a television, a cabinet, a glass coffee table, and a framed picture on the wall.

4. Chic Lakeside Oasis|Near Rhinebeck & Millbrook

Chic Lakeside Oasis|Near Rhinebeck & Millbrook
Stanfordville
The price is AED 1,653
AED 2,518 total
includes taxes & fees
25 Oct - 26 Oct
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 AED 279
AED 934 total
includes taxes & fees
3 Nov - 4 Nov
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 901 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 331
AED 1,115 total
includes taxes & fees
2 Nov - 3 Nov
Retro Retreat: renovated 2BR, desk, no chore list!
A dining area with a chandelier, wooden chairs, a table, and a view through a glass door.

8. 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 493
AED 2,187 total
includes taxes & fees
9 Nov - 10 Nov
Creek Views * Chef’s Kitchen * Walk To Lighthouse
A view from a room with a sliding glass door leading to an outdoor deck with a wooden fence, a chair, and a bench.

9. 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, (105 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 AED 541
AED 878 total
includes taxes & fees
30 Oct - 31 Oct
Esopus Creek modern Tiny house Retreat in Woodstock &Kingston Catskill area!
A modern kitchen with a gas stove, white cabinets, a microwave, and a decorative wall piece.

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 AED 309
AED 971 total
includes taxes & fees
15 Nov - 16 Nov
Sage Sojourn 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.

11. Butterfly and Sage: 2 Studios, Shared Yard

Butterfly and Sage: 2 Studios, Shared Yard
Saugerties
The price is AED 331
AED 1,436 total
includes taxes & fees
8 Nov - 9 Nov
Butterfly and Sage: 2 Studios, Shared Yard
A sectional sofa with matching ottomans, a small table with a lamp, and a patterned rug on a wooden floor.

12. Country House offers 2 bedrooms and a den, lots of parking.

Country House offers 2 bedrooms and a den, lots of parking.
Saugerties
10.0 out of 10, Exceptional, (2 reviews)
"Great house for a last minute getaway. Super clean house!!! Such a cute house with a lovely porch and view. We loved looking at the vintage books on the bookshelf! House had everything we needed, towels, and even shampoo. Would stay again. Location was great too. Centrally located near many attractions but rural enough to relax!"
United States
kristen d.
The price is AED 496
AED 1,275 total
includes taxes & fees
22 Oct - 23 Oct
Country House offers 2 bedrooms and a den, lots of parking.
A kitchen with a stove, cabinets, and a microwave.

13. 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 165
AED 794 total
includes taxes & fees
20 Oct - 21 Oct
Butterfly Bungalow Studio · Saugerties/Woodstock
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.

14. 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 AED 647
AED 2,057 total
includes taxes & fees
28 Oct - 29 Oct
Hot Tub; Big Kitchen; 2 Blocks to Downtown Saugerties
A wooden deck with a staircase leading to a covered porch area.

15. 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 AED 390
AED 519 total
includes taxes & fees
19 Oct - 20 Oct
All the comforts of home
A spacious living room with a large wooden dining table, a comfortable sofa, and a bookshelf filled with books and decorative items.

16. 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 AED 1,469
AED 3,087 total
includes taxes & fees
20 Oct - 21 Oct
Steps to the Delightful Village of Millbrook ☆ Fun Family Getaway
A hot tub with a view of a lake and a dock.

17. 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 950
AED 2,999 total
includes taxes & fees
20 Oct - 21 Oct
Hot tub on water, 5min HITS, 20mi to Hunter skiing
A staircase with a metal handrail and a bench with a striped cushion.

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."
United States
Kristen R.
The price is AED 798
AED 1,857 total
includes taxes & fees
29 Oct - 30 Oct
3BR Farmhouse in the Village of Saugerties - Hike Upstate - Walk to it all!
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 AED 651
AED 1,577 total
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, (2 reviews)
"Perfect for our group of 6"
United States
Patricia S.
The price is AED 1,010
AED 2,221 total
includes taxes & fees
20 Oct - 21 Oct
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

Beekman Arms and Delamater Inn

Beekman Arms and Delamater Inn

10/10 Excellent
"A Wonderful Stay at the Beekman Arms and Delamater Inn! We loved our stay at the Beekman Arms. The location is perfect, with plenty of shopping and restaurants within easy reach. The inn also has a lovely restaurant, and our room was clean, spacious, and comfortable. We stayed in the Courtyard Suite and especially enjoyed the king-size bed and cozy fireplace, which made our stay extra special. The one thing I would mention to future guests is that the Courtyard Suite did not have an elevator. If you have difficulty climbing stairs or carrying luggage upstairs, be sure to ask about the room's location when making your reservation, as we were unaware that our room was on the second floor. Overall, we thoroughly enjoyed our stay and would definitely recommend the Beekman Arms to anyone looking for a charming place to stay in a wonderful location!"
Regina 3-night trip
Posted 10 hours ago
Beekman Arms and Delamater Inn