Seven Spectacular
Hudson Valley Rentals


Summer at one of these pastoral retreats in
New York’s Dutchess and Columbia counties.

A summer in the country is one you’ll never forget. Enjoy your morning coffee while watching the sun rise over the Catskills, then spend the afternoon taking a dip in a secret swimming hole, and finally, end the day with a dinner at one of the local celebrated farm-to-table restaurants.

Consider spending yours at one of these luxe Hudson Valley rental properties.

Pine Plains

The House: This relaxed, stylishly rustic hilltop estate with five bedrooms and five full bathrooms (plus one half bath) boasts a heated 20 x 45-foot pool, a tennis court, a fully stocked pond, and beautiful gardens with an array of gently meandering paths, all spread out on nearly 30 acres. There’s a cathedral-ceiling living room with a stone fireplace, a library, and a formal dining room. Plus, the eat-in kitchen and family room open directly to a terrace with a fireplace and an Argentinian-style grill. All five bedrooms are on the second floor — the primary suite has a balcony with views of Stissing Mountain  while the lower level has a home office and laundry room. There’s also a pool house, with its own loft bedroom, bathroom, kitchen, and a well-equipped gym with a sauna.

The Place: A small town with plenty to do, Pine Plains is a destination worth visiting even from far away. You’ll find eclectic shopping, serious hiking, and a thriving equestrian scene, along with a small but mighty smattering of high-quality eateries — Stissing House is a “Best New Restaurant” contender for this year’s James Beard Awards. It’s also striking distance from Connecticut’s Litchfield County and the Berkshires in Massachusetts, making it a short drive to all the great farms, eateries, and hikes in all three states. 

Represented By: Paula Redmond of Corcoran Country Living.

Available: May 26, 2023 to July 31, 2023


The House: There’s room for everyone in these two luxurious farmhouses set on more than 43 country acres. The primary 4,500-square-foot house, built in 1880 and completely renovated in 2010, has four en suite bedrooms and two half-bathrooms. The 3,000+ square-foot guest house is a modern take on the traditional farmhouse, with an expansive living space topped by a vaulted, beamed ceiling, located right next to the pool — perfect for summer parties. (The guest house also has a kitchen, two bathrooms and a bedroom with two beds.) In addition to the heated pool, there are also two ponds, trails throughout, a pergola, and extensive lawns. 

The Place: Considered the horse capital of Dutchess County, picturesque Millbrook is an idyllic Hudson Valley town. Its charming village teems with antique shops and exciting eateries — there’s a classic diner with tabletop jukeboxes. The surrounding area, or “hunt country” as it’s known locally, is home to top-shelf organic farms and vineyards that supply the kitchens of the plentiful farm-to-table restaurants nearby, as well as in New York City.

Represented By: Paula Redmond of Corcoran Country Living.

Available: May 29, 2023 (Memorial Day) to September 4, 2023 (Labor Day)


The House: A stylish retreat near the center of Woodstock, composed of three structures that offer a total of five bedrooms and five-and-half bathrooms. The main residence, decorated with a modern, sophisticated sensibility, features three bedrooms and three-and-a-half baths. The pool house has a kitchenette, full bath, and a living room with a sofa bed, while the studio cottage has a fireplace, a sofa bed, galley kitchen, full bathroom, and a private outdoor courtyard with a fire pit and grill.  Outside, there’s a pool with a waterfall and hot tub. The primary suite also has its own balcony, complete with mountain views.

The Place: Located a short drive from Kingston within the boundaries of Catskill Park, the Ulster County village of Woodstock ranks among the most charming communities in the region, its bohemian reputation complemented with a ton of cool restaurants and shops. You’ll find waterfalls and swimming holes just about everywhere, and it’s just a quick drive to oft-photographed Kaaterskill Falls.

Represented By: Rich Vizzini and Michelle Bergkamp of Corcoran Country Living.

Available: May 29, 2023 (Memorial Day) to September 4, 2023 (Labor Day)


The House: This pretty four-bedroom, two-and-a-half bathroom country house on 2.5 acres in Staatsburg was built in 1900 and has been lovingly restored to honor the home’s original character. The first floor has a breakfast nook, formal dining and living rooms, and a library or home office. Upstairs, you’ll find all four bedrooms (with the primary suite including an en suite bathroom), and a laundry room. There are also two large screened-in porches, with one on each floor, both facing west and overlooking the Catskill Mountains. 

The Place: Staatsburg is a hamlet in Hyde Park and home to River and Post, a popular restaurant serving craft beer and cocktails and farm-fresh American cuisine. It’s also less than a 10-minute drive to Rhinebeck, with an Amtrak station, or a 20-minute drive south to the Metro-North station in Poughkeepsie. Staatsburg is surrounded by verdant hiking trails and is just across the river from Kingston

Represented By: Kyle Elizabeth Irwin of Corcoran Country Living.

Available: May 29, 2023 (Memorial Day) to September 4, 2023 (Labor Day)


The House: A storybook log cabin with three bedrooms and two bathrooms sits on 8.2 acres, overlooking the Webatuck Creek and a waterfall. The primary bedroom has its own fireplace and overlooks the waterfall and the garden. The other bedrooms include one with a queen bed facing the creek and another with two twin sleigh beds that’s accessed by its own staircase. The house, built in 1933, has plenty of room to spread out, including a great room with a fireplace, a sun room, and a soaking tub in its very own room. 

The Place: Set on the eastern border of Dutchess County, Amenia’s landscape has remained remarkably unchanged for centuries, still boasting the gorgeous views that inspired its name, as “amoena” meaning “pleasing to the eye” in Latin. Amenia is home to Silo Ridge Field Club as well as the luxury retreat Troutbeck, which has a popular restaurant on-site, as well as a membership option with access to its pool and tennis courts. It’s also just a short drive over state lines to Sharon and Lakeville, Connecticut.

Represented By: Paula Redmond of Corcoran Country Living.

Available: June, July, and August 2023

The House: A three-bedroom, two-bathroom country house set on Webatuck Creek is decorated with country-chic interiors. The first floor has the kitchen, dining room, living room, a full bathroom, and an enclosed porch  perfect for reading a book. Upstairs, there are three dormer bedrooms (one with a queen bed, one with a full bed, and one with two twin beds), plus an additional bathroom.  

The Place: This house lies in easy distance to the villages of Amenia and Wassaic (both technically part of the township of Amenia), Millbrook, and the quaint towns of Connecticut’s Litchfield County. It’s a five-minute drive to Metro-North’s Harlem Line for an easy trip into the city, and it’s also close to the Harlem Valley Rail Trail. The Millbrook Hunt Club is also nearby.

Represented By: Paula Redmond of Corcoran Country Living.

Available: Full-time, seasonal, or school-year rental, 


The House: Relax in a four-bedroom European-style farmhouse set on 65+ acres on the hilltops of Ancram, with sweeping views of the Berkshires. The house is a mix of old-world details, like reclaimed beams and shutters, with modern conveniences, including heated slate floors, top-of-the-line appliances, and new mechanicals. There’s an enormous great room with 18′ beamed ceilings and a stone fireplace, and two home offices. Outside, there’s a covered porch and patio, rolling hills, a fire pit, and a 60′ x 20′ gunite pool.

The Place: Ancram is rural and bucolic, and home to some excellent dairy, meat, and pick-your-own fruit farms. It’s also home to the Ancram Opera House, which hosts lively performances, and Hillrock Estate Distillery, which grows all the grains for its exquisite whiskeys on site. It’s also a short drive to Pine PlainsMillerton, Hudson, or Rhinebeck, and about two hours to New York City,

Represented By: Paula Redmond and Karolina Czekaj of Corcoran Country Living.

Available: May 6, 2023 to September 4, 2023. 

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