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, (122)
"Great stay!"
The price is NZ$250
includes taxes & fees
5 Oct - 6 Oct
Micosta Leisure Inn

'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 NZ$279
includes taxes & fees
29 Oct - 30 Oct
'A Place in the Woods' - Cabin on Chloe's Lake on 23 acres near Woodstock, NY

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 NZ$250
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, (30)
"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)
"Had an absolutely fantastic time. Beautiful property and the owners are incredibly kind and welcoming "
A Spectacular 50 Mile View of the Hudson Valley in all seasons

Esopus Creek modern Tiny house Retreat!

9.8 out of 10, Exceptional, (55)
"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 NZ$413
includes taxes & fees
14 Oct - 15 Oct
Esopus Creek modern Tiny house Retreat!

The Farm at Hyde Park

9.8 out of 10, Exceptional, (79)
"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

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 NZ$256
includes taxes & fees
5 Oct - 6 Oct
Sexiest Lil Cabin in Saugerties, NY

Minutes to Saugerties & HITS Horse show. Above garage w/ own private entrance.

2.0 star property
The price is NZ$387
includes taxes & fees
14 Oct - 15 Oct
Minutes to Saugerties & HITS Horse show. Above garage w/ own private entrance.

Charming Yacht on Catskill Creek

8.8 out of 10, Excellent, (10)
"Melisa, the owner, couldn't have made more pleasant and been more available. Without be intrusive. Can only add " if your looking for a different experience. This is it" "
The price is NZ$381
includes taxes & fees
14 Oct - 15 Oct
Charming Yacht on Catskill Creek

Lakefront Fall Foliage in New England Just 2 Hours From NYC

10.0 out of 10, Exceptional, (82)
"Great location and fully equipped cabin! I hope to return sometime soon Everything was perfect!"
Lakefront Fall Foliage in New England Just 2 Hours From NYC

NEW Spectacular Views & Private space on a Scenic Mountain 40ft Salt Water Pool

10.0 out of 10, Exceptional, (131)
"Stunning views, lovely house and pool, large kitchen, well equipped. Very responsive owner. Strongly recommend for family. "
NEW Spectacular Views & Private space on a Scenic Mountain 40ft Salt Water Pool

Rose Cottage

9.2 out of 10, Wonderful, (9)
"It's so peaceful there. It was lovely."
Rose Cottage

Cozy Catskill Cabin w/ 10-minute Walk to Downtown Catskill

9.8 out of 10, Exceptional, (30)
"Great location "
The price is NZ$594
includes taxes & fees
28 Oct - 29 Oct
Cozy Catskill Cabin w/ 10-minute Walk to Downtown Catskill

Summer Lake Cottage, private beach, Berkshire Hills, small village

9.4 out of 10, Exceptional, (82)
"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

‘A Quiet Place’ 3-bedrm house. Mid-Hudson Valley.

10.0 out of 10, Exceptional, (17)
"Our stay was great."
‘A Quiet Place’ 3-bedrm house. Mid-Hudson Valley.

Dog-Friendly Hudson Valley Escape with Hot Tub & Jacuzzi

9.4 out of 10, Exceptional, (23)
"Perfect spot to visit grandkids Lots to do"
The price is NZ$456
includes taxes & fees
29 Oct - 30 Oct
Dog-Friendly Hudson Valley Escape with Hot Tub & Jacuzzi

The Blue Elm - A Historic Berkshire Cottage

10.0 out of 10, Exceptional, (10)
"Everything was great...and beautiful!"
The price is NZ$695
includes taxes & fees
29 Oct - 30 Oct
The Blue Elm - A Historic Berkshire Cottage

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.

Private Yacht on Catskill Creek

9.8 out of 10, Exceptional, (26)
"We had a wonderful time on the boat. Melissa and AJ were wonderful hosts, very responsive. The boat tour was a highlight of a great, very relaxing weekend."
The price is NZ$420
includes taxes & fees
13 Oct - 14 Oct
Private Yacht on Catskill Creek
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

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 favorite 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 depends 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 NZ$250 per night. Entering your travel dates in the search wizard you might find 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?

Esopus Creek modern Tiny house Retreat!: This holiday home rental outside Pine Plains is located on a river, and has a fireplace, a BBQ and air conditioning to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a fridge, a stovetop and a microwave, so that you can cook with friends or family.

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?

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.