
Places to stay in Millbrook
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Top-rated places to stay in Millbrook
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Other great vacation rentals in Millbrook

Vacation Home In Millerton
We had a wonderful week at Corina's house while out for a family event! The house was spotless and the kitchen was stocked with everything we could need. The outside space was just as amazing. We had a great campfire one night, enjoyed using the grill, and our dog loved being able to run around the large yard. I'm sure we'll be back next year!

THE LAKEFRONT CHALET - SKI, RIDE, GOLF, BIKE, HIKE
The house was well stocked, neat and clean. The property has lots of great outdoor space to relax in. Nataliya was very responsive. Thank you.

Summer & Leaf Season Rental!
What a lovely home! It’s in the residential neighborhood above Great Barrington, which means it’s walkable to Lake Mansfield and the trails there and also either a short drive or a nice walk to everything downtown GB has to offer. The house is squeaky clean with nice kitchen amenities, a yard, and a beautiful detached screen porch for warmer months. Perfect size for a small family and very cozy. We will be back!

Private Mountain Lodge, 10mins to Hunter & Windham
My family's second visit to this beautiful gem overlooking the mountains and frozen pond. Our hosts are highly communicative and helpful. The description is accurate. Considering our 2nd visit and rebooked for 3rd in 2026 - this speaks volumes -- more than meets our needs, well stocked. We're looking forward to visiting during the summer months to further appreciate the views. Grateful to them for sharing their home with us.

Little Bear’s Cottage Great location, cozy & cute
We had an amazing stay and we will come back 😊

Mountain View Cottage - Sauna, Jacuzzi, Fire Place
fantastic host and super helpful whenever we had questions. my wife left her iPad there and they mailed it back. verry appreciative of that. first time using a wood fired sauna- I was skittish at first, but it was a great amenity. hot tub was clean and worked well as well. would definitely recommend if you're eyeing a rustic retreat.

Lake house with arcade games
Rosane and Daniel's place was great. Very clean and comfortable. It was well stocked with everything we needed.

A Place Called Home in The Catskill
We just finished a two month rental of John’s wonderful home. Our family of 5 used the home primarily on the weekends when we were enjoying ski season at Belleayre Mountain. I can’t say enough great things about this home. Our family felt totally at home - every aspect was perfectly maintained and the home maximized comfort. Our favorite part of the home was the great room where we would watch movies on the huge family sofa in front of a crackling fire. It was the perfect way to end a day of skiing. Our kids loved the downstairs family room with the foosball table and there were lots of games to play and keep everyone busy and entertained. And the kitchen is huge and very well stocked with all the appliances you will ever need. So it was a fantastic 2 months and we look forward to renting this property again!
Your guide to Millbrook
All About Millbrook
The village of Millbrook sits squarely within New York’s Hudson Valley, filled with lush deciduous forests, gently bubbling streams, and small lakes. The area has long been an upscale retreat but is also well known for its agriculture. You can spend days visiting maple syrup farms, family-owned vineyards, dairy farms with award-winning cheeses, and horse ranches where you can take long rides through wooded trails.
Millbrook itself is less than 20 miles from Poughkeepsie, but its tidy main streets, populated by cozy local storefronts and grand homes dating from the 18th century, make this destination feel a world away from the modern day. Comforting and inviting in that distinctly New England way, this is the kind of village where residents greet each other at the hardware store, host bake sale fundraisers, and lean into a slower pace of life.
The best time to stay in a vacation rental in Millbrook
Each season in the temperate Hudson Valley is quite distinct, making this a popular destination year round. However, it’s always a good idea to pack warm layers regardless of the month. Spring is mild and brings blooms, but temperatures can be cold at night. From May through the end of October, you can visit the local farmers’ market every Saturday morning, which is a great place to shop for artisanal goods or grab a hot coffee. The hot and humid summer weather is great for lake activities, and the Millbrook Literary Festival in May and Summer Carnival in July are popular attractions. The autumn season is great for hiking through forests filled with eye-popping foliage. Winter brings below-freezing temperatures, plenty of snow, and December festivals like the Parade of Lights.
Top things to do in Millbrook
Franklin Avenue
Starting at Tribute Gardens in the center of town, walk east along Franklin Avenue, one of the town’s main streets, to browse Millbrook’s local businesses. Here, you’ll find a three-story antique mall, boutiques selling home decor and handmade souvenirs, a 1950s diner that looks frozen in time, quaint cafes with baked goods, art galleries, and restaurants serving up classic American fare.
Innisfree Garden
This 185-acre garden, just to the southwest of town, is open from May to October. Innisfree takes its cues from traditional Chinese and Japanese gardens and is designed for slow-paced exploration. Each view around Tyrrel Lake has been carefully planned to show the water to best effect, with stone structures, water features, or wooden bridges around every corner. Almost half of the flowering plants here are native wildflowers, but the many varieties of trees are equally spectacular.
Dutchess Wine Trail
You can spend a whole day exploring several vineyards and wineries along this trail; each destination is only about 15 minutes apart by car. The drive itself is incredibly scenic, and you’ll pass orchards, horse farms, small lakes, and wooded streams on your way. Some wineries encourage visitors to bring picnics, while others host food trucks or offer their own menus.
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- Belleayre Mountain Ski Center
- Windham Mountain
- Catamount Mountain Ski Resort
- Minnewaska State Park Preserve
- The Kartrite Resort & Indoor Waterpark
- Taconic State Park
- Thunder Ridge Ski Area
- Rockland Lake State Park
- Walkway Over the Hudson State Historic Park
- Mohawk Mountain Ski Area
- Zoom Flume
- Brotherhood, America's Oldest Winery
- Hook Mountain State Park
- Tamarack Country Club
- Hudson Highlands State Park
- Sherwood Island State Park
- The Connecticut Golf Club
- Sleeping Giant State Park
- Bash Bish Falls State Park
- Norman Rockwell Museum
- Opus 40
- Hartford Golf Club
- Kent Falls State Park
- Bousquet Mountain Ski Area