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Millbrook vacation rentals

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Top-rated vacation rentals in Millbrook

Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.

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Leonardo Lane The Bennett Cabin

Serene setting....private cabin, part of a duplex with upstairs bedroom and bathroom and living area on first floor. Situated on creek, part of 5 acre estate, walk to Orvis Sandanona, right next door, 2 miles to Millbrook Village, 3 miles to Millbrook Vineyards, and close to many Hudson Valley historic sites. Fall asleep to the flowing stream.

$150 per night
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Sweet Village Cottage, garden views, private patio

Inviting Garden Cottage within walking distance to the Village of Millbrook, private entrance/parking with patio and view of the garden. Millbrook is less than 2 hours from NY City and close to the Taconic State Parkway. Perfect for 1 or 2 people with a 2 night minimum stay and 3 night for holiday weekends. Contact us directly for week/month/ shorter stays and for any other questions.

$189 per night
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Leonardo Lane Cottage

The Cottage is the most private of the cabins on Leonardo Lane. It sits above the creek with a deck overlooking the waterfall. There are often herons, ducks and deer seen behind the Cottage. The neighboring property is Orvis Sandanona, world renowned hunting and fishing property. We do hear the sounds of the skeet shooters mostly on the weekends. It doesn’t bother most guests.

$200 per night

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Other great vacation rentals in Millbrook

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The Beech House - Light and Open, Stunning Views
$241 per night
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Village of Millbrook - Spacious Yet Cozy Home
$321 per night
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Leonardo cabin
$200 per night
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Quaint Cottage near Millbrook Village
$135 per night
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Cottage on Coddington Lane
$243 per night
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Charming Cottage + Modern Amenities + Office + Spa
$350 per night
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Quarter House Millbrook
$629 per night
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Millbrook Village Bennett Suite - In the Village
$278 per night
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Serene Waterfront Mill House, Stroll to Village
$323 per night
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Relaxing country getaway at the Millstone Cottage
$275 per night
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Millbrook Cottage Originally a 1927 Sears Kit House
$400 per night
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  2. Millbrook
Classic Country Farmhouse in Millbrook
$850 per night

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.


When is 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.


What are the 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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