Pine Plains Holiday Rentals

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Holiday Rentals in Pine Plains

Balcony
Micosta Leisure Inn
3.0 star property
9.0 out of 10, Wonderful, (72)
"Expedia said they have a Sunday buffet, but they didn't."
The price is NZ$222
per night
26 May - 27 May
Micosta Leisure Inn
Exterior
The Farm at Hyde Park
9.8 out of 10, Exceptional, (48)
"We thoroughly enjoyed our stay. It was a unique setting. Glen was very accommodating for our check in & out needs. Great location & central to everything we wanted to do & see. Definitely would come back."
The Farm at Hyde Park
Property grounds
'A Place in the Woods' - Cabin on Chloe's Lake on 23 acres near Woodstock, NY
8.4 out of 10, Very good, (37)
"Our trip was amazing. We do it again again and again"
The price is NZ$238
per night
29 May - 30 May
'A Place in the Woods' - Cabin on Chloe's Lake on 23 acres near Woodstock, NY
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7 bedrooms, iron/ironing board, cots/infant beds, travel cot
The Freeman - Newly Renovated 14K SF Estate on 40 Acres
10.0 out of 10, Exceptional, (29)
"We had a great time at The Freeman! The little touches like fresh fruit and a welcome basket made it even more special for our family getaway."
The Freeman - Newly Renovated 14K SF Estate on 40 Acres
Fridge, microwave, oven, stovetop
Charming Artist's Retreat
10.0 out of 10, Exceptional, (113)
"From beginning to end a pleasant stay. Owner was on contact to make sure everything was in order. Fresh cut flowers, plenty of clean white fluffy towels, comfortable bedding and the view through sparkling clear windows. What a wonderful way to spend the mother's day weekend with my daughter and spend some time outdoors exploring little Hudson river towns. 10 thumbs up!!!!"
Charming Artist's Retreat
Property grounds
Woodstock Design-Waterfront, Deck, Private Dock Kayak, Swim
10.0 out of 10, Exceptional, (65)
"Very relaxing and enjoyable with excellent views and tranquility!"
Woodstock Design-Waterfront, Deck, Private Dock Kayak, Swim
Exterior
Studio near Millbrook, Poughkeepsie. Close to Polo Club w/ mini farm!
9.0 out of 10, Wonderful, (28)
"For a woodsy getaway close to real highways, here’s your spot. A good home base for local activities. Cute not chic, clean and functional. Chickens and goats on the property added a great farm with no work charm."
Studio near Millbrook, Poughkeepsie. Close to Polo Club w/ mini farm!
Exterior
Beautiful cottage with HOT TUB in Kingston/Woodstock Catskills, Hudson Valley
6.0 out of 10, (2)
"we where on tour with our band. we like to stay a few minutes from the venue. This was the perfect place only a few minutes to downtown woodstock. We would definitely book again, and the host the host are very awesome. That you again Stacey"
The price is NZ$251
per night
2 Jun - 3 Jun
Beautiful cottage with HOT TUB in Kingston/Woodstock Catskills, Hudson Valley
Fridge, microwave, oven, stovetop
Charming Cottage in Private Lake Community (Pet-Friendly!)
9.6 out of 10, Exceptional, (14)
"Clean and comfortable. We had a great time visiting with friends and family at my daughters baby shower!"
Charming Cottage in Private Lake Community (Pet-Friendly!)
Fridge, microwave, oven, stovetop
Campfire Cottage: Fireplace, fire pit & no chores!
10.0 out of 10, Exceptional, (16)
"An unassuming setting belies the well-appointed interior and thoughtful extras you’ll find within. Parking is tight but it is off-street and the location offers come-and-go convenience for exploring the area."
The price is NZ$379
per night
27 May - 28 May
Campfire Cottage: Fireplace, fire pit & no chores!
Fridge, microwave, oven, stovetop
Private Estate, Heated YEARROUND Outdoor Pool
10.0 out of 10, Exceptional, (8)
"The pictures simply do not do this place justice, it’s an incredible home. Our friend group was cozy all weekend! We loved the hot tub/pool, the really interesting artwork, the driving range mat and basketball hoop. Plenty of towels and kitchen supplies. The in law apartment (which we didn’t use as sadly part of our group was unable to join us) is attached to the main home and is so cute. We had a small issue upon arrival and the hosts were immediately responsive with us troubleshooting and...
Private Estate, Heated YEARROUND Outdoor Pool
Property grounds
Hamptons on the Hudson in South Saugerties
9.8 out of 10, Exceptional, (6)
"Rainy but had a great time at the Wool and Sheep Festival.The fall colors were beautiful."
Hamptons on the Hudson in South Saugerties
Property grounds
Dog-Friendly Hudson Valley Escape with Hot Tub & Jacuzzi
10.0 out of 10, Exceptional, (11)
"Perfect spot to visit grandkids Lots to do"
The price is NZ$413
per night
28 May - 29 May
Dog-Friendly Hudson Valley Escape with Hot Tub & Jacuzzi
Exterior
Spectacular Short Term Vacation Rental in Kent
9.6 out of 10, Exceptional, (74)
"For the groomsman it was perfect crazy fun."
Spectacular Short Term Vacation Rental in Kent
Property grounds
Mid-Century DJ’s Dream
10.0 out of 10, Exceptional, (13)
"Our stay was quite nice, the place looked as the pictures showed it to be which is just amazing. everything was music themed and our host had an amazing selection of vinyls. The only complaints I would say I had was the small flying bugs near the Tv and we weren’t provided paper towels. Overall it was a nice place for the night and the property itself was beautiful."
The price is NZ$343
per night
27 May - 28 May
Mid-Century DJ’s Dream
Property grounds
Cozy Relaxing Retreat in Saugerties, NY
10.0 out of 10, Exceptional, (31)
"It was a nice location to spend time with family."
Cozy Relaxing Retreat in Saugerties, NY
Bar (on property)
Romantic Log Cabin on Privately-Owned Lake with Fireplace
9.8 out of 10, Exceptional, (70)
"We love the place it was even more beautiful and peaceful than we expected .It was home away from home with the most gorgeous view . Ms.Karen was wonderful very welcoming . It was all my partner and I need to get away from stressful week . Thanks again Ms.Karen and p.s we love the ice cream Sunday . We are not only highly recommended but soon we will be back . All the best we are very grateful for this staying ."
Romantic Log Cabin on Privately-Owned Lake with Fireplace
Exterior
5-Star New Barn Home - Music Studio, Views & Hot Tub
10.0 out of 10, Exceptional, (18)
"The house is amazing, it delivers on everything stated in the listing and then some. This was our second time staying at Stephen's place and it just keeps getting better. Can't wait for the next one. If you love to listen and play music, its a must."
5-Star New Barn Home - Music Studio, Views & Hot Tub
Fridge, microwave, oven, stovetop
Oversized Country house, Quiet Retreat & Gathering space ~NEW !!!
10.0 out of 10, Exceptional, (13)
"We really enjoyed our stay! We had a large group of 24 friends, and the house met all of our needs. It was very clean, had enough bedrooms for everyone, and a large dining table that accommodated everyone for big dinners. We spent a lot of time throughout the weekend outside playing lawn games and sitting by the fire. The place was close enough to grab amenities or go to a grocery store, but off the beaten path and quiet. It was exactly what was listed and made for a where enjoyable time....
Oversized Country house, Quiet Retreat & Gathering space ~NEW !!!
Exterior
COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!
9.8 out of 10, Exceptional, (7)
"We had a great stay while skiing for 2 days at nearby Catamount ski resort. The kitchen and house were fully stocked with all essentials. Netflix access enabled us to enjoy a family movie after a long day of skiing. Cozy house and quiet area.......nice to wake up to hear birds chirping!!"
The price is NZ$537
per night
27 May - 28 May
COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!
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See all available properties in Pine Plains
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.

Other types of properties in Pine Plains you may be interested in

Free daily continental breakfast
Inn at Pine Plains
3.5 star property
9.8 out of 10, Exceptional, (258)
"Lovely overnight stay. Room was beautiful and very comfortable. Breakfast consisted of a nice selection of homemade bread and muffins - and humus (so yummy). Staff is super friendly and made sure to engage with everyone. Would definitely stay here again. "
The price is NZ$405
per night
4 Jun - 5 Jun
Inn at Pine Plains
Lobby
Best Western Plus Kingston Hotel And Conference Center
2.5 star property
8.0 out of 10, Very good, (1002)
"Always accommodating "
The price is NZ$257
per night
9 Jun - 10 Jun
Best Western Plus Kingston Hotel And Conference Center
Premium bedding, down duvets, Tempur-Pedic beds, laptop workspace
AutoCamp Catskills
3.5 star property
9.2 out of 10, Wonderful, (271)
"Can fishing. "
The price is NZ$370
per night
27 May - 28 May
AutoCamp Catskills
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.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Pine Plains holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Pine Plains. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Pine Plains. Seeing all the best attractions is bound to make you fall in love with Pine Plains. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Pine Plains short-term rentals, that won’t be hard to do.

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 28 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.

Recent reviews of Pine Plains properties
Expedia verified reviews