Pine Plains Holiday Rentals

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Holiday Rentals in Pine Plains

Micosta Leisure Inn

3.0 star property
Hudson
9.2 out of 10, Wonderful, (131)
"Clean, pet friendly , just an overall super nice place to stay "
United States
Gail
The price is AU$222
includes taxes & fees
2 Jan - 3 Jan 2026
Micosta Leisure Inn

The Farm at Hyde Park

Staatsburg
9.8 out of 10, Exceptional, (85)
"Nice stay in an interesting building in an amazing setting. "
United States
Kristen S.
The Farm at Hyde Park

'A Place in the Woods' - Cabin on Chloe's Lake on 23 acres near Woodstock, NY

Saugerties
8.2 out of 10, Very good, (46)
"We had an amazing peaceful time at this property. Check in was seamless and we got lots of great recommendations from our hosts that we really enjoyed! It was very private and cozy and really helped us relax and renew! We will definitely be returning. "
United States
Josh M.
The price is AU$251
includes taxes & fees
3 Dec - 4 Dec
'A Place in the Woods' - Cabin on Chloe's Lake on 23 acres near Woodstock, NY

Hamptons on the Hudson in South Saugerties

Glasco
10.0 out of 10, Exceptional, (34)
"Beautiful home and fantastic pool. Responsive and friendly host. Our whole family had a great time! "
United States
Courtney W.
Hamptons on the Hudson in South Saugerties

Mid-Century DJ’s Dream

Staatsburg
10.0 out of 10, Exceptional, (44)
"Location is well furnished and near many attractionHost versatile and well versed"
United States
Alberto M.
The price is AU$303
includes taxes & fees
6 Dec - 7 Dec
Mid-Century DJ’s Dream

A Spectacular 50 Mile View of the Hudson Valley in all seasons

Saugerties
9.8 out of 10, Exceptional, (95)
"Enjoyed our stay!"
United States
Mike T.
A Spectacular 50 Mile View of the Hudson Valley in all seasons

Esopus Creek modern Tiny house Retreat!

Kingston
9.8 out of 10, Exceptional, (62)
"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. "
United States
Rebecca
The price is AU$407
includes taxes & fees
3 Dec - 4 Dec
Esopus Creek modern Tiny house Retreat!

Sexiest Lil Cabin in Saugerties, NY

Saugerties
9.0 out of 10, Wonderful, (13)
"A little piece of paradise!"
United States
Christi L.
Sexiest Lil Cabin in Saugerties, NY

Dog-Friendly Hudson Valley Escape with Hot Tub & Jacuzzi

Kingston
9.6 out of 10, Exceptional, (25)
"A lovely place and Seth is always so helpful."
United States
Lynn L.
The price is AU$364
includes taxes & fees
4 Dec - 5 Dec
Dog-Friendly Hudson Valley Escape with Hot Tub & Jacuzzi

Sioux Tipi on Chloe's Lake

Saugerties
9.8 out of 10, Exceptional, (6)
"This was such a cool experience Id love to go back! "
United States
Brandon
Sioux Tipi on Chloe's Lake

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

Catskill
9.8 out of 10, Exceptional, (33)
"Very nice cabin lots of property space "
United States
Martin Z.
The price is AU$509
includes taxes & fees
3 Dec - 4 Dec
Cozy Catskill Cabin w/ 10-minute Walk to Downtown Catskill

Wappinger Cottage - Scandinavian retreat on a creek

Poughkeepsie
10.0 out of 10, Exceptional, (23)
"This was the perfect get away spot! Serene location, lovely amenities, and a gracious host."
United States
Laurie C.
Wappinger Cottage - Scandinavian retreat on a creek

Prana Residence Spa with Indoor Pool, Sauna, Jacuzzi & Solarium - near Kent

Cornwall
9.6 out of 10, Exceptional, (53)
"Great house and great stay!"
United States
Timothy P.
Prana Residence Spa with Indoor Pool, Sauna, Jacuzzi & Solarium - near Kent

Private Yacht on Catskill Creek

Catskill
9.8 out of 10, Exceptional, (28)
"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."
United States
Jay
Private Yacht on Catskill Creek

River House by AvantStay | Historic & Secluded Estate on the Hudson River w/Pool

Catskill
9.4 out of 10, Exceptional, (18)
"The house is so historic and very beautiful/interesting. We had a great time. "
United States
Berta T.
River House by AvantStay | Historic & Secluded Estate on the Hudson River w/Pool

Berkshires Family Inn – For Getaways & Big Groups! Walkable to Butternut!

Great Barrington
10.0 out of 10, Exceptional, (28)
"Wonderful old house, very comfortable space for a large family gathering. The kitchen was well-equipped, and exceptionally clean. The host was communicative and responsive, although everything was so well-thought out on his part, we didn't have much need to talk to the hosts. Excellent location, less than five minutes to Great Barrington, and twenty to Tanglewood and Lenox. "
United States
Johnathan B.
Berkshires Family Inn – For Getaways & Big Groups! Walkable to Butternut!

THE ARTIST’S LOFT- Peaceful 1-bedroom apartment in lovely Red Hook with AC, WiFi

Red Hook
9.4 out of 10, Exceptional, (11)
"The loft was easy to find and the perfect location for attending events at Bard and beery picking.Well stocked kitchen and spacious loving room."
United States
Nancy K.
The price is AU$333
includes taxes & fees
4 Dec - 5 Dec
THE ARTIST’S LOFT- Peaceful 1-bedroom apartment in lovely Red Hook with AC, WiFi

Charming 2-bedroom Waterfront home with boat access in Saugerties

Saugerties
9.4 out of 10, Exceptional, (9)
"Really enjoyed our stay. The property had all the comforts of home and was beautiful. "
United States
Sean S.
The price is AU$732
includes taxes & fees
3 Dec - 4 Dec
Charming 2-bedroom Waterfront home with boat access in Saugerties

The Great Escape Ski Cottage w/HOT TUB @ Great Barrington

Great Barrington
10.0 out of 10, Exceptional, (53)
"Great house for a large group. Lots of seating areas indoors and outdoors to accommodate kids and adults. House was very clean and kitchen was well stocked for cooking. We loved that the bedrooms were nicely separated for privacy, particularly the bunk rooms and nearby game room. Great for the late nighters in the bunch!Beautiful property and less than 10 mins to town."
United States
Carol R.
The Great Escape Ski Cottage w/HOT TUB @ Great Barrington

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

Ulster Park
10.0 out of 10, Exceptional, (133)
"Great for a quiet weekend update. New Paltz and Stone Ridge are both close by and have great little main streets. House was very nice and accommodated our group well "
United States
Alex S.
NEW Spectacular Views & Private space on a Scenic Mountain 40ft Salt Water Pool
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$219 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?

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 27 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, Gallatin Town Hall and Pine Plains Library 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.