Pine Plains Holiday Rentals

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Holiday Rentals in Pine Plains

Micosta Leisure Inn
3.0 star property
9.2 out of 10, Wonderful, (126)
"Great stay!"
The price is AU$223
includes taxes & fees
23 Oct - 24 Oct
Micosta Leisure Inn
Sioux Tipi on Chloe's Lake
9.8 out of 10, Exceptional, (6)
"This was such a cool experience Id love to go back! "
The price is AU$227
includes taxes & fees
19 Oct - 20 Oct
Sioux Tipi on Chloe's Lake
Hamptons on the Hudson in South Saugerties
10.0 out of 10, Exceptional, (32)
"Lovely property, well-maintained, clean and comfortable, and the host was especially responsive to all communications. Highly recommend."
Hamptons on the Hudson in South Saugerties
A Spectacular 50 Mile View of the Hudson Valley in all seasons
9.8 out of 10, Exceptional, (92)
"Clean and perfect for a couple. Well maintained and provisioned. Yard/view is overgrown and view is obscured mostly by trees since the dwelling is ground level. But overall a pleasant stay in a quiet treed area. Would do again"
A Spectacular 50 Mile View of the Hudson Valley in all seasons
'A Place in the Woods' - Cabin on Chloe's Lake on 23 acres near Woodstock, NY
8.2 out of 10, Very good, (46)
"A quirky tiny cabin off the beaten path but in need of some upkeep, e.g. toilet not fully attached to the floor in the Tipi room, water has sulphur smell. We were only there for an overnight stay, and I sent a note once we were home, so hopefully the owners get a chance to fix things up! Pricey for its current condition."
The price is AU$252
includes taxes & fees
26 Oct - 27 Oct
'A Place in the Woods' - Cabin on Chloe's Lake on 23 acres near Woodstock, NY
Rose Cottage
9.2 out of 10, Wonderful, (10)
"It's so peaceful there. It was lovely."
Rose Cottage
Minutes to Saugerties & HITS Horse show. Above garage w/ own private entrance.
2.0 star property
The price is AU$355
includes taxes & fees
19 Oct - 20 Oct
Minutes to Saugerties & HITS Horse show. Above garage w/ own private entrance.
Sexiest Lil Cabin in Saugerties, NY
9.0 out of 10, Wonderful, (13)
"We loved our stay here, it was the perfect short getaway. Thanks Alexandria!"
The price is AU$231
includes taxes & fees
20 Oct - 21 Oct
Sexiest Lil Cabin in Saugerties, NY
The Farm at Hyde Park
9.8 out of 10, Exceptional, (81)
"This was the perfect option for us for a nearby wedding. We ate twice at the River & Post (excellent) and went into Rhinebeck for the Sunday market. The property itself was very accommodating and had everything we needed. The kitchen was well equipped, beds comfortable, and plenty of seating options in the main room. The outside area was also a perfect place for coffee in the morning and we loved the chickens running around. Glenn could not have been nicer. Highly recommend!"
The Farm at Hyde Park
Cozy Catskill Cabin w/ 10-minute Walk to Downtown Catskill
9.8 out of 10, Exceptional, (32)
"Great location "
The price is AU$541
includes taxes & fees
4 Nov - 5 Nov
Cozy Catskill Cabin w/ 10-minute Walk to Downtown Catskill
Dog-Friendly Hudson Valley Escape with Hot Tub & Jacuzzi
9.6 out of 10, Exceptional, (25)
"This space was really cute and easy to find. The beds were comfortable, we had all of the amenities needed and even more, and I must mention that the shower in the bathroom was amazing. We all loved being there and were so grateful to be able to travel with our cat and find a pet-friendly space. "
The price is AU$450
includes taxes & fees
4 Nov - 5 Nov
Dog-Friendly Hudson Valley Escape with Hot Tub & Jacuzzi
Summer Lake Cottage, private beach, Berkshire Hills, small village
9.4 out of 10, Exceptional, (83)
"The house has rustic charm and sits right on the lake. It is a beautiful peaceful spot. "
Summer Lake Cottage, private beach, Berkshire Hills, small village
Charming 2-bedroom house in fabulous Kingston close to everything
Charming 2-bedroom house in fabulous Kingston close to everything
Esopus Creek modern Tiny house Retreat!
9.8 out of 10, Exceptional, (58)
"The property was beautiful. Quiet area but close enough to all the places we wanted to go. Our hosts were very gracious, attentive and friendly. Enjoyed our weekend retreat. "
The price is AU$373
includes taxes & fees
22 Oct - 23 Oct
Esopus Creek modern Tiny house Retreat!
Charming Catskill getaway walking distance to Main St. Pet-friendly!
10.0 out of 10, Exceptional, (11)
"We had a great stay here! The check in process was super easy and Jiyon was very communicative. The house was super comfortable and conveniently located for a weekend of hiking. Would definitely stay here again!"
Charming Catskill getaway walking distance to Main St. Pet-friendly!
NEW Spectacular Views & Private space on a Scenic Mountain 40ft Salt Water Pool
10.0 out of 10, Exceptional, (131)
"Bella Vista is a very roomy and beautiful house in a secluded area and this was the second time we have come here. The addition of the swimming pool was a big hit with my grandchildren. The kitchen is well stocked with equipment. This is a great place for chilling out and enjoying family time."
NEW Spectacular Views & Private space on a Scenic Mountain 40ft Salt Water Pool
Private Yacht on Catskill Creek
9.8 out of 10, Exceptional, (27)
"It is a fun alternative to conventional hotel/motel stays. Beautiful waking up on Catskill Creek with as much room as a small hotel room, including 2 double beds plus a dining table that can convert to a bed."
The price is AU$382
includes taxes & fees
19 Oct - 20 Oct
Private Yacht on Catskill Creek
Spacious New Luxurious holiday house in lovely Hudson Valley
9.8 out of 10, Exceptional, (19)
"We loved our stay at this gorgeous home & we will definitely book it again in the future!"
The price is AU$1,083
includes taxes & fees
29 Oct - 30 Oct
Spacious New Luxurious holiday house in lovely Hudson Valley
NEW! Gated 21 Acre Modern Luxury Estate Heated Pool Hot Tub Gym Movie Theater.
9.6 out of 10, Exceptional, (56)
"We hosted a get-away weekend with friends and the property was perfect. There was lots of privacy, which was nice. The home was well stocked. Communications with the property host and property manager was easy. Everything at the home was in working condition. We had a great time."
NEW! Gated 21 Acre Modern Luxury Estate Heated Pool Hot Tub Gym Movie Theater.
Guesthouse Cabin vacation rentals in Berkshire County
10.0 out of 10, Exceptional, (9)
"Really enjoyed the cabin. The pictures don’t do the view justice as it’s an amazing vista overlooking the Berkshires. "
The price is AU$1,110
includes taxes & fees
26 Oct - 27 Oct
Guesthouse Cabin vacation rentals in Berkshire County
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

Find out more about Pine Plains

Everything you need to know about Pine Plains holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Pine Plains holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Pine Plains holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Pine Plains holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Pine Plains. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Pine Plains holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Pine Plains holiday rentals we have selected for you start as low as AU$223 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Pine Plains rentals

At Expedia, we put the best Pine Plains holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Pine Plains rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Pine Plains holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Pine Plains. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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?

Hamptons on the Hudson in South Saugerties: This holiday home rental outside of Pine Plains is located on a river, and has an outdoor pool, a fireplace and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a balcony, a garden and a selection of games so that you can immerse yourself in your holiday.

How many holiday rentals will I find in Pine Plains?

With 29 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?

Stissing Lake Park and Thompson Pond 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.