Pine Plains, NY Vacation Homes from AED 519

A rustic barn surrounded by autumn foliage on a hillside.

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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

Pine Plains

Estefany G.

AED 2,810 total

includes taxes & fees

29 Oct - 30 Oct

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

Pine Plains

stephen r.

AED 4,961 total

includes taxes & fees

16 Oct - 17 Oct

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

Stanfordville

Polly J.

AED 4,101 total

includes taxes & fees

14 Oct - 15 Oct

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

Stanfordville

AED 2,518 total

includes taxes & fees

14 Oct - 15 Oct

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!

Kingston

Brendan B.

AED 901 total

includes taxes & fees

2 Nov - 3 Nov

A modern kitchen with a granite countertop, stainless steel appliances, and a built-in oven.

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

Kingston

Jim R.

AED 938 total

includes taxes & fees

3 Nov - 4 Nov

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!

Kingston

Kelley Marie

AED 1,111 total

includes taxes & fees

2 Nov - 3 Nov

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

Saugerties

molly f.

AED 2,193 total

includes taxes & fees

9 Nov - 10 Nov

A sectional sofa with matching ottomans, a small table with a lamp, and a patterned rug on a wooden floor.

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

Saugerties

kristen d.

AED 1,271 total

includes taxes & fees

26 Oct - 27 Oct

A room with a dark blue wall, two wooden chairs with yellow cushions, a round wooden table, and three framed botanical illustrations.

10. Butterfly and Sage: 2 Studios, Shared Yard

Saugerties

AED 1,436 total

includes taxes & fees

2 Nov - 3 Nov

A modern kitchen with a gas stove, white cabinets, a microwave, and a decorative wall piece.

11. Sage Sojourn Studio · Saugerties/Woodstock

Saugerties

"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...

Cathy H.

AED 880 total

includes taxes & fees

2 Nov - 3 Nov

A kitchen with a stove, cabinets, and a microwave.

12. Butterfly Bungalow Studio · Saugerties/Woodstock

Saugerties

Matias

AED 823 total

includes taxes & fees

2 Nov - 3 Nov

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.

13. Hot Tub; Big Kitchen; 2 Blocks to Downtown Saugerties

Saugerties

Danita K.

AED 2,106 total

includes taxes & fees

28 Oct - 29 Oct

A wooden deck with a staircase leading to a covered porch area.

14. All the comforts of home

Hudson

Lori M.

AED 519 total

includes taxes & fees

19 Oct - 20 Oct

A spacious living room with a large wooden dining table, a comfortable sofa, and a bookshelf filled with books and decorative items.

15. Steps to the Delightful Village of Millbrook ☆ Fun Family Getaway

Millbrook

Beth E.

AED 3,087 total

includes taxes & fees

18 Oct - 19 Oct

A hot tub with a view of a lake and a dock.

16. Hot tub on water, 5min HITS, 20mi to Hunter skiing

Malden

Penny R.

AED 3,125 total

includes taxes & fees

19 Oct - 20 Oct

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!

Saugerties

Kristen R.

AED 1,814 total

includes taxes & fees

28 Oct - 29 Oct

An outdoor seating area with wicker furniture and a glass table, surrounded by lush greenery.

18. Cheerful 3-bedroom cottage with woodstove

Sheffield

Kelly R.

AED 1,577 total

includes taxes & fees

2 Nov - 3 Nov

A wooden deck leading to a cabin with a window and a door, surrounded by trees.

19. Modern cabin retreat

Catskill

AED 1,057 total

includes taxes & fees

19 Oct - 20 Oct

A hot tub in a natural setting with a tree and a body of water.

20. Peaceful Riverfront Cottage with Private Hot tub

Lake Katrine

AED 1,494 total

includes taxes & fees

14 Oct - 15 Oct

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Top Pine Plains Hotel Reviews

Super 8 by Wyndham Kingston

8/10 Good

"Josh was super helpful at Check-in. Very accommodating and super polite. The property was heavily used by semi-permanent guests and needed a bit of cleaning. I was there to close out a storage unit, so the accommodation was very adequate with close proximity to good eateries and downtown Kingston. My room was quiet and had everything I needed. All good."

AutoCamp Catskills

8/10 Good

"Our stay was great , we really enjoyed the clubhouse the boardgames, a small hike on the property and the airstream was nicely equipped with outside grill, smart tv, and very nice outdoor space. Cleaning wise it was okay, we found hair in the shower drain, futon cover felt unwashed and I wish they had coffee in the clubhouse throughout the day. Would definitely recommend it!"

Mirbeau Inn & Spa

10/10 Excellent

"We had an exceptional stay here! The room was huge, clean, and the amenities top notch! Staff were friendly, engaging, and they could not have been more welcoming! Our spa experiences were more than wonderful, and the spa itself is one to experience for sure! An evening at the bar for dinner was heightened by exceptional service provided by Bella! We undoubtedly look forward to returning soon!"

Hotel Kinsley

8/10 Good

"Check in staff only provided information on parking and the address our room was located. It would have been extremely helpful to inform us of the free breakfast, restaurant coupon and the use of the outdoor patio as we bought breakfast out and paid for dessert at the Hotel Kinsey restaurant. The room was very clean."

Room 1

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Pine Plains vacation homes

1. Chic Barn Style * Fireplace * Near Stissing House

2. A Country Lodge Straight Out of the Pages of a Great Novel

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

4. Chic Lakeside Oasis|Near Rhinebeck & Millbrook

5. Retro Retreat: 1br home w/ WFH desk, livingroom, fire pit and no chores!

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

7. Retro Retreat: renovated 2BR, desk, no chore list!

8. Creek Views * Chef’s Kitchen * Walk To Lighthouse

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

10. Butterfly and Sage: 2 Studios, Shared Yard

11. Sage Sojourn Studio · Saugerties/Woodstock

12. Butterfly Bungalow Studio · Saugerties/Woodstock