Choose from 19 vacation rentals located in Pine Plains, New York. Top filters in Pine Plains include Internet / Wifi, Kitchen / Kitchenette, and TV. Prices range from $71 to $1,040 per night. Our most popular vacation rental types near Pine Plains are Hotel and RV.

Top vacation rentals in Pine Plains

View of Stissing Mountain from Twin Island Lake
4.7
Outstanding(64 Reviews)
Cabin
 in Pine Plains
Vintage 50's lake cabin featured in Fresh Cottage Magazine's 'dream retreats'
4 guests · 2 bedrooms · 2 baths
Garden · Pets allowed · Kitchen / Kitchenette

Nestled in Pine Plains, this Cabin is perfect for your next vacation. Enjoy Vintage 50's lake cabin featured in Fresh Cottage Magazine's 'dream retreats''s top-rated amenities, including Fireplace, Internet / Wifi and Pets allowed, and more.

$$$$
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Exterior in Spring
5.0
Outstanding(119 Reviews)
House
 in Pine Plains
Elegant Historic Hudson Valley Gilded Age Mansion On 4+ Parklike Acres
22 guests · 9 bedrooms · 10 baths
Garden · Kitchen / Kitchenette · Air conditioner

Nestled in Pine Plains, this House is perfect for your next vacation. Enjoy Elegant Historic Hudson Valley Gilded Age Mansion On 4+ Parklike Acres's top-rated amenities, including Air conditioner, Dishwasher and Internet / Wifi, and more.

$$$$
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Exterior
4.9
Outstanding(26 Reviews)
House
 in Pine Plains
Lakefront Home in Hudson Valley Dutchess County, Pine Plains, New York
8 guests · 4 bedrooms · 3 baths
Garden · Kitchen / Kitchenette · Air conditioner

Indulge in a peaceful retreat at Lakefront Home in Hudson Valley Dutchess County, Pine Plains, New York, our elegant House in Pine Plains. Enjoy amenities including Air conditioner, Dishwasher and Fireplace, and more.

$$$$
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Enjoy cooking on a Bertazzoni gas range.
4.9
Outstanding(34 Reviews)
House
 in Pine Plains
Hudson Valley Farmhouse on an Idyllic Country Lane
4 guests · 2 bedrooms · 2 baths
Garden · Pets allowed · Kitchen / Kitchenette

Enjoy the best of Pine Plains in our House, Hudson Valley Farmhouse on an Idyllic Country Lane. A stunning property with amenities including Air conditioner, Dishwasher and Fireplace, and more.

$$$$
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Search by amenity

Vacation rentals with internet & wifi in Pine Plains

Exterior
5.0
Outstanding(7 Reviews)
House
 in Pine Plains
Mid-Century Home Surrounded by Meadows
6 guests · 3 bedrooms · 2 baths
Garden · Pets allowed · Kitchen / Kitchenette

The best choice in Pine Plains for House, for $575 per night for your (business stay, family stay, couples stay, getaway vacation, etc.)

$$$$
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Exterior
5.0
Outstanding(12 Reviews)
House
 in Pine Plains
Twin Island Lake House • Hot Tub
6 guests · 3 bedrooms · 2 baths
Garden · Kitchen / Kitchenette · Air conditioner

Looking for a memorable stay in Pine Plains? Our House might just be what you're looking for. Enjoy amenities including Air conditioner, Dishwasher and Fireplace, and more during your stay.

$$$$
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Property view
Condo
 in Pine Plains
Twin Island Lake Private Island
2 guests · 1 bedroom · 1 bath
Garden · Kitchen / Kitchenette · Air conditioner

Looking for the perfect place to call home during your trip to Pine Plains? This Condo offers a comfort and style with top-notch amenities, including Air conditioner, Internet / Wifi and Balcony / Patio, and more.

$$$$
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Outdoor dining
5.0
Outstanding(2 Reviews)
House
 in Pine Plains
Lakefront property at its finest. Nearby fantastic skiing slopes.
6 guests · 2 bedrooms · 1 bath
Ski in / Ski out · Garden · Kitchen / Kitchenette

Indulge in a peaceful retreat at Lakefront property at its finest. Nearby fantastic skiing slopes., our elegant House in Pine Plains. Enjoy amenities including Air conditioner, Internet / Wifi and Laundry, and more.

$$$$
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Pine Plains

Pine Plains travel guide

Let us help you plan your perfect Pine Plains vacation. Our travel guide highlights things to do, places to see, favorite vacation rental amenities in Pine Plains, and more.

Frequently asked questions

What do I need to know before visiting Pine Plains, NY?

Before visiting Pine Plains, NY, it is important to know that the town has a small population and is located in the rural area of Dutchess County. Additionally, you should consider the following:

  • Pine Plains is a small town with a population of about 2,000 people.
  • The town is located in the rural area of Dutchess County, NY.
  • The town has a variety of outdoor activities for visitors to enjoy.

It is also important to note that there are a few local attractions in the area, such as the Noxon Rapids dam and the Roeliff Jansen Park.

What are the must-visit tourist attractions in Pine Plains, NY?

Pine Plains, NY is a great place to visit with plenty of attractions to explore. Here are the top four must-visit tourist attractions in Pine Plains, NY:

  • Stissing Mountain
  • The Pine Plains Community Center
  • The Pine Plains Library
  • The Pine Plains Platter
Visitors can enjoy a scenic hike on Stissing Mountain, explore the local community center, take advantage of the library's resources, and sample the delicious cuisine at the Pine Plains Platter. Whether you're looking for outdoor adventure or a cultural experience, there's something for everyone in Pine Plains.

How can I get around in Pine Plains, NY?

You can get around in Pine Plains, NY in the following ways:

  • By car
  • By bus
  • By bike

The Pine Plains Bus Service runs daily and offers a convenient way to get around the town. Biking is also a popular option, and many of the roads have bike lanes.

Where can I find affordable accommodation in Pine Plains, NY?

For affordable accommodation in Pine Plains, NY, consider staying at the Pine Plains Motel. It offers:

  • Clean, comfortable rooms
  • Free Wi-Fi
  • Cable TV
  • Close proximity to popular attractions

The Pine Plains Motel is a great option for those looking for a budget-friendly stay in the area. With its convenient location and friendly staff, you'll be sure to have a comfortable and enjoyable stay.

What is the culture like in Pine Plains, NY?

Pine Plains, NY is a small rural town situated in the Hudson Valley in Dutchess County. With a population of just over 2,000 people, the town is steeped in rural culture and values.

  • Friendly and helpful neighbors
  • Strong sense of community
  • Locally owned shops and small businesses
  • Outdoor activities like hiking, swimming, fishing, and skiing
  • Local festivals and community events

Is Pine Plains, NY safe to travel to?

Pine Plains, NY is generally considered a safe place to travel to. Here are a few key points to keep in mind:

  • Crime rates are low.
  • The town is small and the people are friendly.
  • It is important to be aware of your surroundings and take the necessary safety precautions.

What are the popular shopping destinations in Pine Plains, NY?

Popular shopping destinations in Pine Plains, NY include:

  • The Local Farm Stand
  • Vintage Boutique
  • Grocery Store

What are the best neighborhoods to visit in Pine Plains, NY?

The best neighborhoods to visit in Pine Plains, NY are:

  • Main Street
  • Taconic Parkway
  • Route 199

Each of these neighborhoods offer something unique to explore, from historic sites to outdoor recreational activities.

Where is Pine Plains, NY?

Pine Plains, NY is a small town located in Dutchess County, New York, about 2 hours north of New York City. It is home to about 2,500 people and is known for its rural charm, historic sites, and outdoor activities. There are a variety of parks, shops, restaurants, and galleries throughout the town, making it a popular destination for visitors and locals alike.

What are the most popular vacation rental amenities in Pine Plains, NY?

The most popular vacation rental amenities in Pine Plains, NY include:

  • On-site pool and spa
  • Fitness center
  • Complimentary breakfast
  • Free Wi-Fi
  • Air-conditioning

These amenities provide guests with the ultimate vacation experience, allowing them to stay in luxury and comfort. From the on-site pool and spa to the complimentary breakfast and free Wi-Fi, guests have access to everything they need to make their stay enjoyable and memorable.

What are the top things to do in Pine Plains, NY?

Pine Plains, NY is a great destination for outdoor enthusiasts, with plenty of activities to choose from. Here are some of the top activities to enjoy in Pine Plains:

  • Go hiking at Stissing Mountain State Park
  • Visit the local wineries
  • Take a dip at the Stewart House Pool
  • Explore the historic sites and museums
Pine Plains is a beautiful area of New York, and there's always something to do for the whole family. Whether you're looking for outdoor adventure or a leisurely day of sightseeing, Pine Plains has something for everyone.

What is the price range for rentals in Pine Plains?

Vacation rentals in Pine Plains have a price range between $71-$1,040. The average price for rentals in Pine Plains is $248 per night.

What are the most popular vacation rental amenities in Pine Plains?

  • Internet / Wifi
  • Kitchen / Kitchenette
  • TV

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