Pine Plains Vacation Rentals from $89: Search Short-Term Rentals

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Our top choices for Pine Plains vacation rentals

A spacious living area with a sofa, ottoman, and a dining table with chairs. A staircase leads to an upper level.

1. NEW: Chic Modern Barn Style Home in Fun Area

Pine Plains

Estefany G.

$664 nightly

Dec 13 - Dec 14

Total with taxes and fees

A modern kitchen with white cabinets, a large island, and a skylight.

2. A Country Lodge Straight Out of the Pages of a Great Novel

Pine Plains

Marianne R.

$1,180 nightly

Nov 13 - Nov 14

Total with taxes and fees

A covered outdoor deck with wicker furniture, a grill, and a view of a lake.

3. Chic Lakeside Oasis|Near Rhinebeck & Millbrook

Stanfordville

$580 nightly

Nov 15 - Nov 16

Total with taxes and fees

A rustic interior with wooden beams, multiple windows, and a kitchen area with dishes and a coffee maker.

4. rural, serene + sophisticated space

Red Hook

BRIAN PATRICK M.

$344 nightly

Dec 1 - Dec 2

Total with taxes and fees

A large, two-story house with a covered porch and a stone foundation, surrounded by snow-covered trees.

5. The George is an elegant restored home in the Hudson Valley

Stanfordville

Polly J.

$1,120 nightly

Nov 14 - Nov 15

Total with taxes and fees

A rustic cabin with a dining area set up outside, a bicycle, and a sign indicating the name 'Vangelis'.

6. Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

Catskill

Mike

$209 nightly

Dec 13 - Dec 14

Total with taxes and fees

A tented area with two wooden folding chairs and a table, a patterned rug, and a view of greenery and a white tent in the background.

7. Gatherwild Ranch

Germantown

AYANO

$361 nightly

Nov 13 - Nov 14

Total with taxes and fees

A wooden deck with a lattice railing, surrounded by lush greenery and a gravel path.

8. Micosta Leisure Inn

Hudson

George

$79 nightly

Nov 16 - Nov 17

Total with taxes and fees

A neatly made bed with a white pillow, a red pillow, and a white blanket. There is a small bedside table with a lamp.

9. Hibiscus Suite - Private Studio Apartment in Rhinebeck Village

Rhinebeck Village

Heather O.

$212 nightly

Nov 29 - Nov 30

Total with taxes and fees

A residential property with a well-maintained lawn, a small house with a front porch, and a garage.

10. Sharon Retreat w/ Private Yard

Sharon

Heidi F.

$392 nightly

Nov 13 - Nov 14

Total with taxes and fees

A cozy living room with a sofa, armchair, wooden coffee table, and a dining area with a table and chairs.

11. Ideal location for summer and winter activities with plenty of outdoor space.

Hillsdale

Richard M.

$307 nightly

Nov 15 - Nov 16

Total with taxes and fees

A kitchen with white cabinetry, granite countertops, and a window with blinds.

12. Charming loft cottage in tranquil Germantown with WiFi, AC

Germantown

Kanna S.

$217 nightly

Nov 16 - Nov 17

Total with taxes and fees

A white house with a steeply pitched roof and a small tower-like structure.

13. Charming 2-bedroom apartment on 2nd floor in Millbrook NY, right in the village

Millbrook

Laurie F.

$414 nightly

Nov 13 - Nov 14

Total with taxes and fees

A spacious loft with a high ceiling, exposed wooden beams, a staircase, a flat-screen TV, and a round wooden coffee table with a plant.

14. Stunning and Cozy loft apartment in kingston .

Kingston

Robin H.

$226 nightly

Nov 15 - Nov 16

Total with taxes and fees

A modern kitchen with white cabinets, a central island, and a view to the outside.

15. Pleasant 1-bedroom apartment in Staatsburg perfect for your getaway,

Staatsburg

elizabeth

$176 nightly

Dec 1 - Dec 2

Total with taxes and fees

16. Hudson Valley Farm Getaway- West/Llama Lover Lane

Hyde Park

alexandra a.

$201 nightly

Dec 1 - Dec 2

Total with taxes and fees

An outdoor patio with a striped rug, seating, a fire pit, and string lights.

17. Dog-Friendly Hudson Valley Escape with Hot Tub & Jacuzzi

Kingston

Erin H.

$226 nightly

Nov 16 - Nov 17

Total with taxes and fees

A dining area with a chandelier, wooden chairs, a table, and a view through a glass door.

18. Creek Views * Chef’s Kitchen * Walk To Lighthouse

Saugerties

molly f.

$607 nightly

Nov 15 - Nov 16

Total with taxes and fees

A spacious living room with a large wooden dining table, a comfortable sofa, and a bookshelf filled with books and decorative items.

19. Steps to the Delightful Village of Millbrook ☆ Fun Family Getaway

Millbrook

Beth E.

$706 nightly

Nov 16 - Nov 17

Total with taxes and fees

A restaurant with outdoor seating, a sign for 'The New York Restaurant', and a nearby antique shop.

20. Charming Cottage in the Heart of Catskill & Pet Friendly

Catskill

Dave P.

$313 nightly

Nov 15 - Nov 16

Total with taxes and fees

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Top Pine Plains Hotel Reviews

Residence Inn by Marriott Kingston

10/10 Excellent

"Everything was great.staff was very helpful and room was excellent. Only drawback was that the bed was very low to the floor."

Kingston Regency Inn

10/10 Excellent

"I recently attended a roundtable meeting on New York folklore and stayed at the Kingston Regency Inn for two nights. Overall, I had a very pleasant experience. The staff were warm, welcoming, and always willing to help. The conference facilities were excellent. The meeting room was spacious, well organized, and quiet, which created a comfortable environment for discussion and learning. The hotel was also very clean and well maintained. Throughout my stay, I felt safe and relaxed. The surrounding area was peaceful and convenient, with several dining options within just a short walk. There was a particularly nice restaurant nearby that made meals easy and enjoyable after a full day of meetings. For visitors interested in arts and culture, the Kingston area is also a great place to explore. The region has a vibrant artistic atmosphere, with local galleries, cultural events, and historic sites that reflect the rich heritage of the Hudson Valley. This added an extra layer of enjoyment to my trip. I would gladly stay here again and would recommend this hotel to both business travelers and conference attendees looking for a comfortable, quiet, and convenient place to stay"

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 $89 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.

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Things to do in Rhinebeck

Frequently asked questions

Are there vacation rentals in Pine Plains?

Yes, there are vacation rentals in Pine Plains close to The Stissing Center, or you can choose a more remote option if you'd like a relaxing place to stay.

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

Esopus Creek modern Tiny house Retreat in Woodstock &Kingston Catskill area!: You might want to consider this vacation rental near Pine Plains, which is located on a river and has a fireplace, a patio, and a barbecue grill 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 23 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.

Pine Plains Vacation Rentals

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Check prices for these dates

Our top choices for Pine Plains vacation rentals

1. NEW: Chic Modern Barn Style Home in Fun Area

2. A Country Lodge Straight Out of the Pages of a Great Novel

3. Chic Lakeside Oasis|Near Rhinebeck & Millbrook

4. rural, serene + sophisticated space

5. The George is an elegant restored home in the Hudson Valley

6. Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

7. Gatherwild Ranch

8. Micosta Leisure Inn

9. Hibiscus Suite - Private Studio Apartment in Rhinebeck Village

10. Sharon Retreat w/ Private Yard

11. Ideal location for summer and winter activities with plenty of outdoor space.

12. Charming loft cottage in tranquil Germantown with WiFi, AC

13. Charming 2-bedroom apartment on 2nd floor in Millbrook NY, right in the village

14. Stunning and Cozy loft apartment in kingston .

15. Pleasant 1-bedroom apartment in Staatsburg perfect for your getaway,

16. Hudson Valley Farm Getaway- West/Llama Lover Lane

17. Dog-Friendly Hudson Valley Escape with Hot Tub & Jacuzzi

18. Creek Views * Chef’s Kitchen * Walk To Lighthouse

19. Steps to the Delightful Village of Millbrook ☆ Fun Family Getaway

20. Charming Cottage in the Heart of Catskill & Pet Friendly

Find vacation rentals that suit your style

Top Pine Plains Hotel Reviews

Residence Inn by Marriott Kingston

Find out more about Pine Plains

Explore a world of travel with Expedia

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