Pine Plains Holiday Rentals

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Check prices for these dates

Tonight
11 Jul - 12 Jul
Tomorrow
12 Jul - 13 Jul
This weekend
11 Jul - 13 Jul
Next weekend
18 Jul - 20 Jul

Holiday Rentals in Pine Plains

CT Gate House Goshen CT, Gate House Goshen CT
Step into this charming cabin, featuring a spacious porch and covered seating area amidst lush surroundings.

CT Gate House Goshen CT, Gate House Goshen CT

2.5 star property
The price is HK$1,621
HK$6,056 total
includes taxes & fees
14 Jul - 15 Jul
CT Gate House Goshen CT, Gate House Goshen CT
Mid Century Modern Studio w/ Full Kitchen - Newly Built
Fridge, microwave, oven, stovetop

Mid Century Modern Studio w/ Full Kitchen - Newly Built

8.0 out of 10, Very good, (1)
"Super cute, clean, and convenient for our quick trip to The Millbrook School."
The price is HK$1,531
HK$2,410 total
includes taxes & fees
13 Jul - 14 Jul
Mid Century Modern Studio w/ Full Kitchen - Newly Built
Cheerful 3-bedroom cottage with woodstove
Relax in a serene outdoor space surrounded by lush greenery, featuring a wicker sofa set and a coffee table.

Cheerful 3-bedroom cottage with woodstove

10.0 out of 10, Exceptional, (38)
"The property was centrally located for skiing, and was a comfortable stay."
The price is HK$2,096
HK$4,217 total
includes taxes & fees
31 Jul - 1 Aug
Cheerful 3-bedroom cottage with woodstove
Home in Great Barrington
Enjoy cooking in this well-lit kitchen with a large window offering a view of the outdoors.

Home in Great Barrington

9.8 out of 10, Exceptional, (21)
"Our family had a wonderful experience and stay. "
The price is HK$1,872
HK$2,880 total
includes taxes & fees
15 Jul - 16 Jul
Home in Great Barrington
Great Barrington Get Away
Enjoy cooking in this kitchen with stainless steel appliances, a large window offering a view of the outdoors, and a convenient trash can.

Great Barrington Get Away

9.4 out of 10, Exceptional, (23)
"Nice, cozy, clean house with character. Great location as we could walk to town. Would stay again for sure."
The price is HK$3,532
HK$5,761 total
includes taxes & fees
13 Jul - 14 Jul
Great Barrington Get Away
Hillsdale Escape with Pool, Firepit, Hot Tub, Game Room
Relax in the serene outdoor patio, featuring a fire pit, round table, and comfortable seating.

Hillsdale Escape with Pool, Firepit, Hot Tub, Game Room

The price is HK$7,182
HK$12,522 total
includes taxes & fees
4 Aug - 5 Aug
Hillsdale Escape with Pool, Firepit, Hot Tub, Game Room
3 bedroom, 2 bath, Waterfall, Back Yard, Patio, Fire pit, and Grilling Station!
Exterior

3 bedroom, 2 bath, Waterfall, Back Yard, Patio, Fire pit, and Grilling Station!

The price is HK$2,559
HK$3,765 total
includes taxes & fees
1 Aug - 2 Aug
3 bedroom, 2 bath, Waterfall, Back Yard, Patio, Fire pit, and Grilling Station!
The George is an elegant restored home in the Hudson Valley
Enjoy a serene view of the rolling countryside from this room's window.

The George is an elegant restored home in the Hudson Valley

9.0 out of 10, Wonderful, (4)
"Nice big house in a quiet location. "
The price is HK$4,521
HK$7,317 total
includes taxes & fees
14 Jul - 15 Jul
The George is an elegant restored home in the Hudson Valley
rural, serene + sophisticated space
Cozy room with a chandelier, sofa, and armchair, offering a view of the outdoors.

rural, serene + sophisticated space

10.0 out of 10, Exceptional, (7)
"Beautiful property with unique accommodations in the Hudson Valley"
The price is HK$2,112
HK$2,612 total
includes taxes & fees
13 Jul - 14 Jul
rural, serene + sophisticated space
Spacious New Luxurious holiday house in lovely Hudson Valley
Enjoy expansive mountain views from this sunroom with a sofa, table, and wicker chair.

Spacious New Luxurious holiday house in lovely Hudson Valley

10.0 out of 10, Exceptional, (11)
"We loved our stay at this gorgeous home & we will definitely book it again in the future!"
The price is HK$3,356
HK$6,021 total
includes taxes & fees
14 Jul - 15 Jul
Spacious New Luxurious holiday house in lovely Hudson Valley
Rhinebeck Inn Suite with Private Deck
Set amidst lush greenery, this two-story house offers a secluded retreat with a sloped roof and surroundings.

Rhinebeck Inn Suite with Private Deck

2.0 star property
The price is HK$2,004
HK$2,570 total
includes taxes & fees
29 Jul - 30 Jul
Rhinebeck Inn Suite with Private Deck
Cozy Rhinebeck Inn Suite
Set amidst lush greenery, this two-story house offers a serene retreat with a covered porch and a beautifully maintained lawn.

Cozy Rhinebeck Inn Suite

10.0 out of 10, Exceptional, (2)
The price is HK$1,823
HK$2,340 total
includes taxes & fees
29 Jul - 30 Jul
Cozy Rhinebeck Inn Suite
Rhinebeck Inn Suite with Private Deck and Fire Pit
Set amidst lush greenery, this two-story house offers a secluded retreat with a well-maintained lawn and trees.

Rhinebeck Inn Suite with Private Deck and Fire Pit

The price is HK$2,058
HK$2,658 total
includes taxes & fees
14 Jul - 15 Jul
Rhinebeck Inn Suite with Private Deck and Fire Pit
Rhinebeck Inn Suite with a Private Deck
Relax on the deck with comfortable seating and a charming lantern, surrounded by the serene forest.

Rhinebeck Inn Suite with a Private Deck

The price is HK$2,185
HK$2,801 total
includes taxes & fees
29 Jul - 30 Jul
Rhinebeck Inn Suite with a Private Deck
Historic Hudson Valley Estate
Cozy retreat with a large bed, bedside table, and kitchenette area, offering a view of the outside.

Historic Hudson Valley Estate

The price is HK$7,842
HK$12,161 total
includes taxes & fees
14 Jul - 15 Jul
Historic Hudson Valley Estate
Modern Converted Barn with Hot Tub!
Cozy living room with a fireplace, large window, and dining area.

Modern Converted Barn with Hot Tub!

10.0 out of 10, Exceptional, (4)
"The house has a big open floor plan with extra large windows letting light and views in. The bedrooms are comfortable and the kitchen is well equipped. Big playroom was heaven for our toddler. Highly recommend.this property."
The price is HK$4,121
HK$6,741 total
includes taxes & fees
14 Jul - 15 Jul
Modern Converted Barn with Hot Tub!
All the comforts of home
Surrounded by lush greenery, this deck features a spiral staircase leading to an upper level.

All the comforts of home

9.0 out of 10, Wonderful, (23)
"Really liked staying at Steven’s place! The hot tub was a great touch. Stayed in Unit 1 - it’s small but perfect for what we needed it for! "
The price is HK$834
HK$1,070 total
includes taxes & fees
13 Jul - 14 Jul
All the comforts of home
Beautiful, Spacious, 5 Acre Hudson Valley Family Retreat
Relax on the patio with a round table and two chairs, surrounded by a white railing and overlooking a serene grassy area with trees.

Beautiful, Spacious, 5 Acre Hudson Valley Family Retreat

10.0 out of 10, Exceptional, (4)
"Our stay was only a couple nights but it was what we expected. I would recommend this property. Had a great stay."
The price is HK$2,551
HK$4,913 total
includes taxes & fees
27 Jul - 28 Jul
Beautiful, Spacious, 5 Acre Hudson Valley Family Retreat
Modern Creekside Stay with Hot Tub 10 mins to Downtown Hudson
Relax in this stylish living room with a flat-screen TV, comfortable sofa, and two armchairs.

Modern Creekside Stay with Hot Tub 10 mins to Downtown Hudson

9.8 out of 10, Exceptional, (7)
"Great space for our family of four and dog. Lots of room to spread out and relax. Nice local events going on and great location to stores and short drive to hiking spots and many restaurants. Host had great communication with us and answered all of our questions in a really timely manner. Definitely recommend this spot!"
The price is HK$2,669
HK$5,197 total
includes taxes & fees
11 Aug - 12 Aug
Modern Creekside Stay with Hot Tub 10 mins to Downtown Hudson
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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Frequently asked questions

Are there holiday rentals in Pine Plains?

Yes, there are holiday rentals close to the most popular sights in Pine Plains, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Pine Plains has to offer?

The Farm at Hyde Park: This holiday home rental outside of Pine Plains is located in a rural location, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. Kick off your shoes and enjoy yourself with a garden and a selection of games.

How many holiday rentals will I find in Pine Plains?

With 30 Expedia holiday rentals, you're guaranteed to find just the right place for your Pine Plains stay.

What can I see and do in Pine Plains?

Thompson Pond and Stissing Lake Park are a couple of scenic spots to enjoy the outdoors, whereas The Stissing Center is one of the cultural attractions. While here, Pine Plains Library and Gallatin Town Hall are other places worth a visit.

What are holiday rentals like in Pine Plains?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Pine Plains. Holiday rentals feature extras like laundry facilities and kitchens so you'll have a home away from home. If you're concerned about cleanliness, a holiday rental can offer a sense of seclusion away from shared hotel lifts and busy front desks while still allowing you the excitement and enjoyment of travel. You'll also have more space in a holiday rental than in a traditional hotel, which makes a holiday rental an attractive option for a family trip.