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A rustic barn surrounded by autumn foliage on a hillside.

Find hotels in Pine Plains, NY from $74

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Check prices for these dates, December 14 – 15, 2026

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Our top choices for Pine Plains hotels

1. AutoCamp Catskills

A modern house with a sloped roof, large windows, and a well-maintained lawn.

2. Beekman Arms and Delamater Inn

A large white building with a central entrance, surrounded by well-maintained gardens and multiple American flags.

3. Inn at Pine Plains

A dining area with a table set for breakfast, a chalkboard menu, and various kitchen utensils hanging on the wall.

4. Hyatt Place Poughkeepsie / Hudson Valley

A modern hotel with a prominent 'Hyatt Place' sign, outdoor seating area, and a covered entrance.

5. Hampton Inn & Suites Poughkeepsie

A modern hotel lobby with wooden flooring, yellow chairs, a long dining table, and pendant lighting.

6. Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires

A tranquil stream with rocks and trees, a building with balconies and a red railing, and a clear sky.

7. The Red Lion Inn

An aerial view of a residential area with a prominent white building with a dark roof, surrounded by autumn-colored trees.

8. Jenny's Country Manor

A vintage black car parked on a road with a white fence and trees in the background.

9. the Alander

A modern building with a dark exterior, outdoor seating area with wooden chairs, and string lights.

10. DoubleTree by Hilton Poughkeepsie Convention Center

A modern hotel lobby with seating areas, large windows, and contemporary lighting fixtures.

11. Mirbeau Inn & Spa

A large, multi-story hotel with a symmetrical facade, multiple balconies with flower boxes, and a central entrance with a fountain.

12. the suite @ barn & bike - private, bucolic, serene setting

A kitchen with wooden shelves, a sink, and a dining area with a table and chairs.

13. Residence Inn by Marriott Kingston

A spacious lobby with a fireplace, comfortable seating, and large windows.

14. Holiday Inn Express Poughkeepsie by IHG

A lobby with a wooden bench, a reception desk, and a colorful artwork on the wall.

15. Hampton Inn by Hilton New Paltz

A lobby with a stone fireplace, patterned armchairs, and a large rug.

16. Inn at Bellefield / Hyde Park, Residence Inn by Marriott

A spacious living area with stone pillars, leather sofas, a fireplace, and a kitchen in the background.

17. SureStay Plus Hotel by Best Western Highland Poughkeepsie

A hotel room with two beds, a desk, a chair, a lamp, and a window with curtains.

18. voco James Newbury Hudson Valley by IHG

A lakeside property with a glass conservatory, a pathway leading to a building, and a sunset view.

19. Little Cat Lodge

A wooden fire pit surrounded by six Adirondack chairs in a forested area.

20. Courtyard by Marriott Kingston

An outdoor patio with a fire pit, seating, and a building in the background.

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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Hotels recommended for families in Pine Plains

Inn at Pine Plains

A dining area with a table set for breakfast, a chalkboard menu, and various kitchen utensils hanging on the wall.

NEW: Chic Modern Barn Style Home in Fun Area

An outdoor patio with wooden furniture, a grill, and a fire pit.

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

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

Rhinecliff Hotel

A white picket fence, a grassy lawn, and a body of water in the background.

Courtyard by Marriott Kingston

An outdoor patio with a fire pit, seating, and a building in the background.

Holiday Inn Express & Suites Kingston-Ulster by IHG

A hotel with a covered entrance, stone facade, and a sign indicating it is a Holiday Inn Express & Suites.

Gatherwild Ranch

An outdoor covered patio with a wooden table and chairs, a hanging light fixture, and a view of the surrounding greenery.

Changing Times Boutique Country Lodging

A fire pit with two Adirondack chairs, a table with drinks, and a house in the background.

Where to stay near Pine Plains

Pine Plains offers a serene escape with its lovely grounds and breathtaking scenery. Explore the picturesque Hudson Valley, venture to nearby Glens Falls for adventure, or relax in the charming Wyoming Plains. For a unique day trip, consider the coastal vibes of Pismo Beach. Your outdoor, romantic getaway awaits!

A church with a steeple, a bell tower, and a large arched window.

An aerial view of a dense forest with a variety of trees displaying autumn colors.

A colorful storefront with a sign for 'EB's Hudson Valley Finds Gallery' and 'Bread Alone'.

A vintage storefront with a red and white sign for Village Pizza & Restaurant, a checkered sidewalk, and pedestrians walking by.

A calm river with mountains on either side and a sunset sky.

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Rhinebeck

Discover Rhinebeck, a welcoming destination perfectly suited for travelers seeking a blend of culture and nature. With attractions like the Omega Institute, the Dutchess County Fairgrounds, and Bard College, visitors can immerse themselves in educational and outdoor experiences year-round. Just about a 16-mile drive from Pine Plains, Rhinebeck offers a scenic escape that makes it an ideal choice for your vacation stay. Enjoy the charm of this vibrant town while exploring its rich offerings.

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A wooden pier leading to a historic brick house with a tower, overlooking a calm lake.

A sunset over a calm lake with mountains in the background.

A brick building with a tower, surrounded by snow and tall grasses.

A river with a red bridge, surrounded by autumn-colored trees and houses.

A dam with multiple waterfalls, surrounded by lush greenery and rocky cliffs.

View properties in map for Saugerties

Saugerties

Experience the charm of Saugerties, an excellent hub for families and outdoor enthusiasts eager to explore the beauty of the Hudson Valley. With attractions like the historic Bard College, the equestrian center HITS-on-the-Hudson, and the Bethel Woods Museum, there's something for everyone. Nestled about 30 miles away from Pine Plains, Saugerties offers a diverse range of activities year-round, making it a smart choice for your next vacation stay.

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Ancramdale

If you are a nature enthusiast, look no further than Ancramdale, which features stunning outdoor activities, including access to Taconic State Park and recreational areas perfect for family adventures. The charming local attractions, like the Ancram Town Hall and The Stissing Center, enrich your experience during your stay. Located about 4 miles by car from Pine Plains, Ancramdale is an excellent choice for a memorable getaway filled with exploration and relaxation.

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Ancram

Ancram stands out as a prime spot for families and outdoor enthusiasts interested in a weekend getaway immersed in nature. Here, you can explore the scenic Lake Taghkanic State Park, unwind by the picturesque Lake Taghkanic, and visit the historic Bard College, all while enjoying a range of outdoor adventures. Ideally located about 5 miles by car from Pine Plains, Ancram offers easy access to both relaxation and excitement, making it a smart choice for your next vacation.

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A rural landscape with a river, green fields, and red barns.

A rural landscape with a windmill, a silo, and a barn.

A forest stream with rocks and fallen leaves.

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Millerton

Travelers visiting the area often choose Millerton, especially families and outdoor enthusiasts seeking close proximity to breathtaking scenery and adventure. This charming city offers access to attractions like the Holley-Williams House Museum and the Harney and Sons Tea Tasting Room, along with thrilling activities at nearby ski fields and scenic views from Mount Frissell. Located about 8 miles by car from Pine Plains, Millerton is a smart choice for a memorable getaway, blending relaxation and outdoor fun.

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Stay near popular Pine Plains attractions

Pine Plains offers a captivating blend of outdoor adventures and romantic scenery, perfect for those seeking a serene getaway. Explore the stunning nature reserves and nearby Litchfield Hills, and unwind in a beautiful inn while enjoying the charm of New York's countryside.

A grassy field with a brick wall and a large tree with autumn leaves.

Bard College

Rating: 8.6/10 (100 reviews)

Ideal for a quick visit and a memorable day out, Bard College offers a unique blend of historic charm and cultural vibes. Located about 20 miles by car from Pine Plains, this picturesque campus provides an enriching experience for travelers. Staying nearby makes exploring the area easy and enjoyable.

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A biplane with red and white stripes flying against a clear blue sky.

Old Rhinebeck Aerodrome

Rating: 9.4/10 (8 reviews)

Perfectly suited for aviation history lovers, Old Rhinebeck Aerodrome offers a unique glimpse into early flight with its impressive collection of vintage aircraft. Located about 17 miles by car from Pine Plains, it’s an easy trip that allows you to explore the rich culture of aviation while enjoying the scenic Hudson Valley.

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Omega Institute

Rating: 9.2/10 (31 reviews)

Set the stage for your rejuvenating retreat at the Omega Institute, perfect for wellness seekers and those looking to connect with nature. Nestled in Rhinebeck, this institute offers a unique blend of historical charm and urban vibes. It's about an 18-mile drive from Pine Plains, making it a convenient spot for your peaceful getaway.

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Thompson Pond

Rating: 8.0/10 (1 review)

Ideal for travelers seeking a serene escape, Thompson Pond offers a relaxing and romantic atmosphere amidst its tranquil waters. Located within Pine Plains, this secluded spot is perfect for leisurely strolls or quiet reflection. Staying nearby grants easy access to this peaceful haven, enhancing your visit to the area.

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Wing's Castle

No trip is complete without a visit to Wing's Castle, a charming spot for couples seeking a blend of romance and culture. Located about 15 miles by car from Pine Plains, this enchanting castle offers a unique experience amidst stunning architecture and beautiful grounds, making it a convenient and memorable stop on your journey.

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Dutchess County Fairgrounds

Rating: 8.8/10 (66 reviews)

Discover the appeal of Dutchess County Fairgrounds, a vibrant destination perfect for families looking to enjoy outdoor events and activities. Located about 21 miles by car from Pine Plains, this fairground offers a variety of experiences that make it a great place to relax and have fun during your visit.

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Lake Taghkanic State Park

Rating: 10.0/10 (1 review)

Enjoy the simplicity of nature at Lake Taghkanic State Park, perfect for outdoor lovers seeking adventure and stunning scenery. Located about 11 miles by car from Pine Plains, this park offers a refreshing escape with its inviting landscapes and recreational opportunities, making it an ideal spot for a relaxing getaway.

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Taconic State Park

Rating: 9.8/10 (11 reviews)

A must-see for outdoor enthusiasts, Taconic State Park offers stunning scenery and a wealth of adventure. Located about 13 miles by car from Pine Plains, this park's natural beauty and outdoor activities make it a perfect spot to explore and unwind. Staying nearby provides easy access to its trails and vistas.

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Learn more about Pine Plains

Hike the trails of Stissing Mountain for panoramic views of this charming Hudson Valley town and its surrounding countryside. Spend afternoons exploring local farm stands or enjoying the peaceful waters of Stissing Lake with a picnic from Main Street businesses.

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A rustic barn surrounded by autumn foliage on a hillside.

Top Pine Plains Hotel Reviews

Inn at Pine Plains

A dining area with a table set for breakfast, a chalkboard menu, and various kitchen utensils hanging on the wall.

Holiday Inn Express & Suites Kingston-Ulster by IHG

A hotel with a covered entrance, stone facade, and a sign indicating it is a Holiday Inn Express & Suites.

Changing Times Boutique Country Lodging

A fire pit with two Adirondack chairs, a table with drinks, and a house in the background.

Rhinecliff Hotel

A white picket fence, a grassy lawn, and a body of water in the background.

The White Hart

A large, two-story house with a porch and multiple windows, surrounded by a well-maintained lawn.

Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

A cabin with a fire pit, picnic table, and Adirondack chairs in a forest setting.

Hampton Inn Kingston

A spacious living area with a fireplace, a dining table with chairs, and a television mounted on the wall.

Little Cat Lodge

A wooden fire pit surrounded by six Adirondack chairs in a forested area.

AutoCamp Catskills

A modern house with a sloped roof, large windows, and a well-maintained lawn.

Howard Hotel

A hallway with a staircase, a framed painting, a mirror, and a potted plant.

Holiday Inn Express & Suites Saugerties - Hudson Valley by IHG

A swimming pool with clear water, surrounded by walls with emergency contact information and pool rules.

Residence Inn by Marriott Kingston

A spacious lobby with a fireplace, comfortable seating, and large windows.

Monument Mountain Motel

A neatly made bed with white linens, two bedside lamps, a nightstand with a telephone, and a painting on the wall.

Holiday Inn Express Hotel & Suites Great Barrington by IHG

An indoor swimming pool with a 6 feet 18 meters depth, surrounded by chairs and tables, with large windows offering views of trees.

The Nest Hudson

A window with a gold-framed shelf containing a potted plant, a white bowl, and two gold pitchers.

Prospect Berkshires

A wooden house with a porch, surrounded by trees and a body of water.

Wilder House Berkshires

A room with a wooden floor, two red armchairs, a small table, and a window with a view of trees.

Find out more about Pine Plains

Top reasons to visit Pine Plains

Find great hotels near Pine Plains

Pine Plains, New York, offers a charming selection of accommodations, including inviting agritourism properties and cozy bed & breakfasts. Whether you're seeking a pet-friendly retreat, a family-friendly adventure, or a peaceful getaway, you'll find great options to enhance your stay. Explore hotels near Pine Plains and discover the best inns and lodgings that cater to all types of travelers looking to enjoy the beauty and hospitality of this lovely area.

Where to stay near Pine Plains

Pine Plains, New York, offers a perfect blend of outdoor adventures and romantic scenery, making it an ideal vacation spot. Visitors can explore stunning landscapes and enjoy vibrant nightlife, while nearby areas provide a family-friendly atmosphere and historical charm. Whether you seek relaxation or adventure, Pine Plains and its surroundings promise a memorable experience in upstate New York.

Things to do in Pine Plains

Pine Plains offers a charming escape for outdoor enthusiasts and couples alike, featuring activities such as skiing and educational experiences. It's an ideal weekend getaway, allowing visitors to explore the area's scenic beauty and various amenities. Whether you’re hitting the slopes or enjoying the tranquil surroundings, Pine Plains provides a perfect blend of adventure and relaxation.

Shopping

Pine Plains offers charming local shops for unique gifts and souvenirs. Check out The Pine Plains General Store for local crafts. If you're up for a drive, visit the Hudson Valley Mall in nearby Kingston, featuring a variety of stores from clothing to electronics.

Recreation

The Pine Plains Wellness Center offers yoga classes and holistic therapies in a tranquil setting. Enjoy guided meditation sessions and rejuvenating massages, all designed to refresh your spirit. For outdoor enthusiasts, the nearby Taconic State Park features hiking trails and scenic views, perfect for reconnecting with nature.

Adventure

Explore the scenic trails at the Pine Plains Nature Preserve for a day of hiking and wildlife spotting. For an adrenaline rush, try nearby Dutchess County's zip-lining experience, soaring through the treetops while enjoying panoramic views of the Hudson Valley.

Nightlife

Experience the cozy ambiance at The Pine Plains Tavern, where you can enjoy hearty pub fare and local brews. For a more vibrant scene, visit The Red Barn, offering live music and dancing on weekends, making it a perfect spot to unwind and mingle with locals.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Booking tips and Expedia advantages for Pine Plains

Find the best attractions in and around Pine Plains

Pine Plains, New York, is a charming destination perfect for outdoor lovers and those seeking a romantic getaway. Visitors can explore local attractions such as national and state parks, serene lakes, and beautiful nature reserves. Whether you're after adventure, cultural experiences, or simply stunning scenery, Pine Plains offers a variety of activities that cater to all interests, making it an ideal spot for a memorable vacation.

Best time to go to Pine Plains

The best time to visit Pine Plains can depend on the weather and when visitor numbers rise and fall. The hottest average temperature in Pine Plains falls in July, when visitor numbers are moderately high and weather is mostly sunny with light rain. The coolest average temperature in Pine Plains falls in January, visitor numbers are average and weather is mostly cloudy with light rain.

Calendar MonthTemperaturePrecipitationCloudinessOccupancyPricing
January24.4°F (-4.2°C)Light RainMostly CloudyAverageSlightly Low
February26.4°F (-3.1°C)Light RainMostly CloudyAverageAverage
March34.2°F (1.2°C)Light RainMostly CloudyAverageSlightly Low
April45.9°F (7.7°C)Light RainMostly CloudyModerately HighAverage
May57.2°F (14.0°C)Light RainMostly SunnyAverageAverage
June65.1°F (18.4°C)Light RainMostly SunnyAverageAverage
July71.4°F (21.9°C)Light RainMostly SunnyModerately HighSlightly High
August69.4°F (20.8°C)Light RainMostly SunnyModerately HighSlightly High
September62.4°F (16.9°C)Light RainMostly SunnyAverageAverage
October51.3°F (10.7°C)Light RainMostly SunnyModerately LowSlightly High
November39.0°F (3.9°C)Light RainMostly SunnyModerately LowAverage
December30.6°F (-0.8°C)Light RainMostly CloudyModerately LowSlightly Low

The nearest major airports for your trip to Pine Plains

If you're planning to visit Pine Plains, New York, you have several major airports to consider. New York, NY (JFK-John F. Kennedy Intl.) and Newark Liberty Intl. Airport (EWR) are both located 93 miles away, while New York, NY (LGA-LaGuardia) is slightly closer at 84 miles. Excellent hotel options near JFK include the 5-star Arlo Williamsburg and The William Vale, both 11 miles away. Near EWR, you can stay at The Dominick or Four Seasons Hotel New York Downtown, both 9 miles from the airport. For LGA, The Plaza and The Pierre, A Taj Hotel, are both 5 miles away, offering convenient airport transportation services.

Frequently Asked Questions

What is the best area to stay in Pine Plains?

The best area to stay in Pine Plains is the area around the town center, particularly along Main Street and its immediate surroundings.

This central area offers convenient access to local establishments and the village green. You'll find a selection of local shops, cafes, and eateries within walking distance, making it easy to explore the town on foot. The town center provides a pleasant, low-key atmosphere for visitors.

Couples looking for a relaxing getaway will appreciate the quiet surroundings and the ability to stroll to dinner or a local shop without needing a car.

What are the best hotels in Pine Plains that travelers recommend?

For travelers seeking highly recommended accommodations in Pine Plains, the Inn at Pine Plains is an excellent choice.

The 3.5-star Inn at Pine Plains boasts an impressive 9.8 rating from guests. This hotel is praised for its great location, being just 0.2 miles from Pine Plains Library, 0.8 miles from Thompson Pond, and 0.9 miles from Stissing Lake Park. Guests also frequently highlight the cleanliness of the suites. Amenities include air conditioning, premium bedding, and a complimentary continental breakfast.

What hotels in Pine Plains offer free breakfast?

For hotels in Pine Plains that offer complimentary breakfast, the Inn at Pine Plains is an excellent choice.

This 3.5-star hotel, boasting an impressive 9.8 rating, provides a free continental breakfast daily, ensuring a convenient start to your day. Guests appreciate the complimentary self-parking and the fact that pets can stay free. It is conveniently located near local attractions, just 0.2 miles from the Pine Plains Library, 0.8 miles from Thompson Pond, and 0.9 miles from Stissing Lake Park.

What are the top pet-friendly hotels in Pine Plains?

For a top pet-friendly hotel in Pine Plains, consider the Inn at Pine Plains.

The 3.5-star Inn at Pine Plains, with an excellent 9.8 rating, is highly recommended for travelers with pets. Pets are permitted to stay free, and this hotel specifically welcomes dogs. Guests can also enjoy a complimentary continental breakfast during their stay. The Inn at Pine Plains is conveniently located near Stissing Lake Park, the Pine Plains Library, and Thompson Pond, offering easy access to local attractions. See more pet-friendly hotels in Pine Plains

What are the best hotels in Pine Plains near Thompson Pond?

For a comfortable stay in Pine Plains near Thompson Pond, consider the Inn at Pine Plains.

This 3.5-star hotel, with an exceptional 9.8 rating, is located just 0.8 miles from Thompson Pond. It offers complimentary breakfast, including a continental option, and free toiletries, adding convenience to your stay. Guests appreciate the free self-parking and the fact that pets can stay free. Many guests have praised its great location and the cleanliness of its suites.

When is the best time to go to Pine Plains?

The best time to visit Pine Plains is during the summer and fall months, from June through October, when the weather is most favorable for outdoor activities and local events are plentiful.

Summer in Pine Plains, particularly July and August, offers warm temperatures great for enjoying Stissing Lake. Visitors can swim, kayak, or simply relax by the water. The Pine Plains Farmers Market is also in full swing during these months, providing fresh local produce and artisan goods.

For those who appreciate scenic beauty and comfortable temperatures, September and October are ideal. The changing leaves create a picturesque landscape, making it a great time for hiking or exploring the numerous trails around Stissing Mountain.

Can I cancel my hotel reservation on Expedia?

You can cancel your hotel reservation on Expedia, though it depends on the cancellation policy of your booking. Most bookings are refundable if canceled within 24-48 hours of the scheduled arrival. Be sure to check your booking confirmation for the exact cancellation policy. If free cancellation is available, you can cancel directly through your Expedia account by logging in, going to "My Trips", and selecting your reservation. To find flexible deals, filter your search by "Fully refundable property" for hotels in Pine Plains.

How much is the nightly rate at a Pine Plains hotel?

Prices for hotels in Pine Plains often vary, but you can find a great deal from $74 on Expedia. All sorts of factors affect price, such as the time of year or the days of the week you choose for your stay. Find the best deals by being flexible with your dates, and sort search results by "Price: low to high" for the cheapest rate.

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