Pine Plains Vacation Rentals

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Vacation Rentals in Pine Plains

Micosta Leisure Inn
3.0 star property
9.0 out of 10, Wonderful, 74 reviews
"Expedia said they have a Sunday buffet, but they didn't."
The price is CA $172
CA $193 total
includes taxes & fees
Jun 23 - Jun 24
Micosta Leisure Inn
The Farm at Hyde Park
9.8 out of 10, Exceptional, 50 reviews
"Had a wonderful time, got to see family in the area, were welcomed by the trio of chix, enjoyed learning about the history of the area from our knowledgeable host and are looking forward to getting back in 2025"
The Farm at Hyde Park
'A Place in the Woods' - Cabin on Chloe's Lake on 23 acres near Woodstock, NY
8.4 out of 10, Very good, 37 reviews
"Our trip was amazing. We do it again again and again"
The price is CA $171
CA $171 total
includes taxes & fees
Jun 23 - Jun 24
'A Place in the Woods' - Cabin on Chloe's Lake on 23 acres near Woodstock, NY
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Beautiful cottage with HOT TUB in Kingston/Woodstock Catskills, Hudson Valley
8.0 out of 10, Very good, 4 reviews
"A quick drive to the village of Woodstock, this unit has a great location and was super clean and comfortable. Beautiful new squeaky clean hot tub, comfy bed, and well-equipped. It was perfect for our Woodstock weekend!"
The price is CA $171
CA $248 total
includes taxes & fees
Jul 7 - Jul 8
Beautiful cottage with HOT TUB in Kingston/Woodstock Catskills, Hudson Valley
The Freeman - Newly Renovated 14K SF Estate on 40 Acres
10.0 out of 10, Exceptional, 29 reviews
"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
Riverfront property in the beautiful Hudson Valley with many outdoor activities.
9.4 out of 10, Exceptional, 41 reviews
"The house is decorated beautifully, and the view of the river is great. The beds and linens were soo comfortable. Would love to return in warmer weather to enjoy the outdoors 😀"
Riverfront property in the beautiful Hudson Valley with many outdoor activities.
Studio near Millbrook, Poughkeepsie. Close to Polo Club w/ mini farm!
9.0 out of 10, Wonderful, 30 reviews
"Very charming one room apartment with bathroom and kitchen area. Beautiful surrounding you with very pleasant hosts"
Studio near Millbrook, Poughkeepsie. Close to Polo Club w/ mini farm!
Charming Artist's Retreat
10.0 out of 10, Exceptional, 115 reviews
"It's our second time staying at the "retreat". Aptly named. Beautiful location and perfect for us celebrating my wife's retirement. Maureen has been a gem both times. Hope to visit again! And OH, the sunsets and the birds and the deer and the house with a history on the hill with a view!"
Charming Artist's Retreat
Campfire Cottage: Fireplace, fire pit & no chores!
10.0 out of 10, Exceptional, 16 reviews
"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 CA $177
CA $361 total
includes taxes & fees
Jun 23 - Jun 24
Campfire Cottage: Fireplace, fire pit & no chores!
Hamptons on the Hudson in South Saugerties
9.8 out of 10, Exceptional, 7 reviews
"Really cute interior. Perfect for our stay while at the horse show "
Hamptons on the Hudson in South Saugerties
Spectacular Short Term Vacation Rental in Kent
9.6 out of 10, Exceptional, 74 reviews
"For the groomsman it was perfect crazy fun."
Spectacular Short Term Vacation Rental in Kent
Private Estate, Heated YEARROUND Outdoor Pool
10.0 out of 10, Exceptional, 8 reviews
"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
Cozy Relaxing Retreat in Saugerties, NY
10.0 out of 10, Exceptional, 33 reviews
"Pictures can fool anyone but as my son and I entered this property on our first day, he raised his hand with a genuine smile of joy, uttering that in renting this house, I made a very good choice. He was visiting me from Germany for his birthday, and I wanted to spend some days away from NYC, in quiet, conversation, and cooking. Being there for five days provided for us a wonderful framework to spend time together, and the house is as inviting as the pictures suggest. Our only criticism is a...
Cozy Relaxing Retreat in Saugerties, NY
Spacious restored Victorian w/ wraparound porch
9.4 out of 10, Exceptional, 10 reviews
"The property was gorgeous, the house large enough to accommodate our group. The kitchen was well stocked. We used the pool, hot tub, fire pit, and pool table. The indoor and outdoor speakers were a nice touch. I would definitely recommend this home I had to reach out to our host 2 days before check in to find out how to get in- usually that is communicated earlier than that. I had informed the host that we were going to have a luncheon for 10 additional people after the memorial service and was...
Spacious restored Victorian w/ wraparound porch
COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!
9.8 out of 10, Exceptional, 7 reviews
"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 CA $218
CA $458 total
includes taxes & fees
Jul 2 - Jul 3
COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!
Sexiest Lil Cabin in Saugerties, NY
8.4 out of 10, Very good, 6 reviews
"We loved our stay here, it was the perfect short getaway. Thanks Alexandria!"
The price is CA $171
CA $171 total
includes taxes & fees
Jun 23 - Jun 24
Sexiest Lil Cabin in Saugerties, NY
Romantic Log Cabin on Privately-Owned Lake with Fireplace
9.8 out of 10, Exceptional, 71 reviews
"The cabin is really cute & has wind chimes & garden art all around it that integrates so perfectly with the natural oasis it is set in. This is a great place for a nature loving couple to enjoy. Singing birds, frogs, turtles chipmunks & fish in the lake, are the only neighbors you will notice o this beautiful property. Karen is a lovely gracious host and both she and the cabin are very welcoming & charming. Its a perfect spot go to with your soulmate & reconnect with nature."
Romantic Log Cabin on Privately-Owned Lake with Fireplace
River House by AvantStay | Historic & Secluded Estate on the Hudson River w/Pool
9.8 out of 10, Exceptional, 10 reviews
"The number of bedrooms and bathrooms was great for the 13 of us. The big kitchen, pantry and long dining tables made for fun interaction. The game room with pool table and ping pong table were perfect for after dinner fun. Beautiful property on the river. We plan to go back. Historic homes are tough to maintain and our hope is that it is as nice in the future as it was this week."
River House by AvantStay | Historic & Secluded Estate on the Hudson River w/Pool
Charming Cottage in Private Lake Community (Pet-Friendly!)
9.6 out of 10, Exceptional, 14 reviews
"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!)
4-bedrooms with gym+spa access in the Village of Saugerties 1/4 mile from HITS!
9.0 out of 10, Wonderful, 11 reviews
"Loved the location! Very quiet and clean. Will stay here again!"
4-bedrooms with gym+spa access in the Village of Saugerties 1/4 mile from HITS!
Don't see what you're looking for?
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

Best Western Plus Kingston Hotel And Conference Center
2.5 star property
8.0 out of 10, Very good, 1,001 reviews
"token machine was broken, arcade games were iffy and vending machine was out of soda. But we still had a great time in the pool and the breakfast was great and the rooms comfy and clean. Didn't know how to turn on fan in bathroom.Love the courtyard!"
The price is CA $192
CA $215 total
includes taxes & fees
Jul 7 - Jul 8
Best Western Plus Kingston Hotel And Conference Center
AutoCamp Catskills
3.5 star property
9.0 out of 10, Wonderful, 284 reviews
"Beautiful"
The price is CA $306
CA $391 total
includes taxes & fees
Jul 22 - Jul 23
AutoCamp Catskills
Howard Johnson by Wyndham Saugerties
2.0 star property
7.6 out of 10, Good, 1,004 reviews
"Excellent place all around"
The price is CA $167
CA $187 total
includes taxes & fees
Jun 23 - Jun 24
Howard Johnson by Wyndham 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.

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation 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 or room. 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 vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . 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 . 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 vacation rental 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 vacation 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 short-term rentals, that won’t be hard to do.

Frequently asked questions

Are there vacation rentals in Pine Plains?

Yes, there are vacation rentals close to well known local attractions in Pine Plains, or you can go with a more remote option if you're looking for a relaxing stay.

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

The Farm at Hyde Park: You might want to consider this vacation rental near Pine Plains, which is located in a rural location and has a fireplace, a patio, and a barbecue grill 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 vacation rentals will I find in Pine Plains?

With 29 Expedia vacation rentals, you're sure 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 vacation rentals like in Pine Plains?

Vacation rentals are privately owned accommodations you can stay in for a couple days or more in Pine Plains. Vacation rentals feature amenities like kitchens and laundry facilities so you'll have everything you need. If you're concerned about a clean environment, a vacation rental can offer a sense of security away from shared hotel elevators and lobbies bustling with people while still allowing you to travel. You'll also get more space in a vacation rental than in a hotel, which makes a vacation rental an attractive choice for small groups.

Recent reviews of Pine Plains properties
Expedia verified reviews