Pine Plains Vacation Rentals

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Vacation Rentals in Pine Plains

Micosta Leisure Inn

3.0 star property
Hudson
9.2 out of 10, Wonderful, (130)
"Clean, pet friendly , just an overall super nice place to stay "
United States
Gail
$131 nightly
The price is $147
Nov 21 - Nov 22
Total with taxes and fees
Micosta Leisure Inn

'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.
$145 nightly
The price is $162
Nov 12 - Nov 13
Total with taxes and fees
'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, (33)
"The entire process and stay were flawless. We had a rush booking and every request we had was accommodated. I give the highest recommendation and will hopefully being staying here again."
United States
Gordon V.
Hamptons on the Hudson in South Saugerties

The Farm at Hyde Park

Staatsburg
9.8 out of 10, Exceptional, (84)
"We enjoyed our stay...lots to do in the area. Glen was very friendly and accommodating. "
United States
Robert W.
The Farm at Hyde Park

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

Saugerties
9.8 out of 10, Exceptional, (95)
"Had my mother in law and sister in law in town and booked them this adorable place with an amazing view close to town. "
United States
Emily K.
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, (60)
"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
$216 nightly
The price is $241
Nov 19 - Nov 20
Total with taxes and fees
Esopus Creek modern Tiny house Retreat!

Mid-Century DJ’s Dream

Staatsburg
10.0 out of 10, Exceptional, (42)
"Great place to stay! Close to many attractions by car - most 10-15 minutes. Clean and comfortable. Kevin has lots of great suggestions on places to go and restaurants."
United States
Anonymous traveler
$173 nightly
The price is $196
Nov 18 - Nov 19
Total with taxes and fees
Mid-Century DJ’s Dream

Sexiest Lil Cabin in Saugerties, NY

Saugerties
9.0 out of 10, Wonderful, (13)
"We loved our stay here, it was the perfect short getaway. Thanks Alexandria!"
United States
Julie L.
Sexiest Lil Cabin in Saugerties, NY

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
$130 nightly
The price is $146
Nov 16 - Nov 17
Total with taxes and fees
Sioux Tipi on Chloe's Lake

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

Catskill
9.8 out of 10, Exceptional, (33)
"Great location "
United States
steve p.
$305 nightly
The price is $330
Nov 11 - Nov 12
Total with taxes and fees
Cozy Catskill Cabin w/ 10-minute Walk to Downtown Catskill

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.
$202 nightly
The price is $226
Nov 11 - Nov 12
Total with taxes and fees
Dog-Friendly Hudson Valley Escape with Hot Tub & Jacuzzi

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

Lakeville
9.4 out of 10, Exceptional, (84)
"Wonderful lake retreat 🥾"
United States
Elizabeth B.
Summer Lake Cottage, private beach, Berkshire Hills, small village

The Blue Elm - A Historic Berkshire Cottage

Sheffield
10.0 out of 10, Exceptional, (14)
"If I could have given it more than 5 stars I would have. Beautiful, quiet area and the place is stunning. The gas fireplace in the dining area was great, has pretty much everything you could need and incredibly stylish (the retro fridge and microwave were very cool). Can’t speak to the pullout but the king in the master might have been the most comfortable bed I’ve ever slept in and the double shower is awesome. The hosts were friendly and responsive. Went to hike and the number of trails within...
United States
Marc R.
The Blue Elm - A Historic Berkshire Cottage

Hot Tub - Fire Pit - BBQ - Hammock - Colonial

Kingston
9.4 out of 10, Exceptional, (22)
"We came down with our dog. We work a lot and needed a break. The place is cozy and comfy and the outdoor space is so lovely. Good mix of sunny space and shaded space.Our dog very much enjoyed the backyard and we loved the small businesses within walking distance "
United States
Heather H.
$198 nightly
The price is $222
Nov 11 - Nov 12
Total with taxes and fees
Hot Tub - Fire Pit - BBQ - Hammock - Colonial

Charming 2-bedroom house in fabulous Kingston close to everything

Kingston
10.0 out of 10, Exceptional, (1)
"House was spotless. Hosts were very responsive and helpful. "
United States
Lawrence R.
Charming 2-bedroom house in fabulous Kingston close to everything

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

Ulster Park
10.0 out of 10, Exceptional, (132)
"The house was comfortable for a large group, beautiful setting, private, clean, etc. We enjoyed our stay."
United States
mary r.
NEW Spectacular Views & Private space on a Scenic Mountain 40ft Salt Water Pool

Secluded family retreat within minutes of Woodstock village

Woodstock
10.0 out of 10, Exceptional, (47)
"A beautiful, clean house that came as advertised. We spent a lot of time out and about but enjoyed whenever we were at the house."
United States
Patrick F.
Secluded family retreat within minutes of Woodstock village

Country Cottage with beautiful views and easy access to Catskills activities.

Saugerties
10.0 out of 10, Exceptional, (12)
"Cozy little spot for a quick getaway. Very clean, quiet location. Easy check-in. "
United States
Mariclare C.
$159 nightly
The price is $178
Nov 11 - Nov 12
Total with taxes and fees
Country Cottage with beautiful views and easy access to Catskills activities.

Private Yacht on Catskill Creek

Catskill
9.8 out of 10, Exceptional, (28)
"It was great!"
United States
Chaya S.
Private Yacht on Catskill Creek

Cozy Modern Studio Apt in Glasco

Saugerties
2.0 out of 10, (3)
"Wish I could, however host cancelled the day off our arrival after I reached out several times for access information!!!"
United States
Helene D.
$196 nightly
The price is $220
Nov 11 - Nov 12
Total with taxes and fees
Cozy Modern Studio Apt in Glasco
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 vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Pine Plains vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Pine Plains vacation 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 low season months. For more hustle and bustle, you may prefer to visit Pine Plains in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $146 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Pine Plains rentals

At Expedia, we put the best Pine Plains vacation 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 vacation.

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 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?

Esopus Creek modern Tiny house Retreat!: You might want to consider this vacation home rental near Pine Plains, which is located on a river and has a fireplace, a barbecue grill, 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 you can cook with friends or family.

How many vacation rentals will I find in Pine Plains?

With 27 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?

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 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.