Places to stay in Millbrook

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Top-rated places to stay in Millbrook

Guests agree: these places to stay are highly rated for location, cleanliness, and more.

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Top guest favorite

An outdoor space features a barbecue grill, a circular firepit surrounded by four chairs, and a coffee table. Scattered trees provide shade, while a deck is visible in the background. A shed is seen in the distance, adding a functional element to the setting.

Home in Wappingers Falls

4.96 out of 5 average rating, 26 reviews

Caroline House Beacon Getaway

Set just outside Beacon in a beautiful, quaint neighborhood, this is the perfect retreat for family and friends after a fun day at all of the local attractions. Enjoy the large outdoor space with firepit, grill, hammock and deck or any of the close by farms, breweries, downtown Beacon and the many Hudson River adventures. Just 7 minutes from the Beacon MTA train and I84 with all the excitement at your fingertips set in a beautiful neighborhood where you may spot our neighbors horses roaming.

Guest favorite

A winter scene depicts a charming town square with snow-covered ground, featuring a building adorned with a glowing Christmas tree in its window. Vintage cars are parked in front, while small groups of people are visible, creating a festive atmosphere against a twilight sky.

Apartment in Stockbridge

4.96 out of 5 average rating, 104 reviews

Historic,Famous,Iconic, Unforgettable Berks Escape

PICTURE IT...You can put yourself in the "famed" Norman Rockwell Main Street at Christmas Painting! That's Right,Cozy, Intimate,Magical and all to yourself.Fully equipped with all the comforts of home. Small Town Charm,Big time Historic setting in the heart of Downtown Stockbridge! Spend your afternoon sipping Tea or Wine looking out the iconic picture window Norman Rockwell installed himself. The one where the Christmas Tree Glows in a room that was Norman Rockwell's Studio from 1953-1957

Superhost

A brick fireplace serves as a focal point, with several white candles arranged on the hearth. Natural light filters through a nearby window adorned with sheer curtains, illuminating the seating area with cozy cushions beside a built-in bookshelf.

Apartment in Kingston

4.77 out of 5 average rating, 115 reviews

In the Heart of Kingston

Pet friendly. A comfortable apartment in the heart of midtown Kingston. Enjoy a cup of coffee in the garden, or curl up with a book in the window seat in the living room. This apartment is a great spot to relax from a day of exploring Kingston. You will be close to everything when you stay at this centrally-located place. Note: located near a train; so if you are a light sleeper, it might not be a good fit. Garden area is still in winter mode (until May 15th), so please excuse the mess.

Guest favorite

A well-lit bedroom features a black wooden bed with a plush blanket layered over crisp white linens. A small bedside table holds a lamp, and framed photos adorn the walls. A window with a blackout shade allows natural light while a wooden chair adds a touch of warmth.

Home in Sheffield

4.91 out of 5 average rating, 117 reviews

Wow! Best BERKSHIRE SnowHome #1 Private SuperClean

"238 Main" has two rentals. Only one rental is rented at a time. Rental #1 has 2 bedrooms, FULLY EQUIPPED KITCHEN and is SUPERCLEAN! (SEE THE 1 BEDROOM LISTING #2!) We are conveniently located between Butternut and Catamount ski stations. Fully renovated, large garden, private entrance, terrace and parking space. Queen size beds. High Speed WiFi. Bathroom has radiant floor heat, towel warmer, plush bathrobes, hairdryer and toiletries. We are in the heart of the Berkshires come visit!

Top guest favorite

The kitchen features white cabinetry with open shelves displaying an assortment of glassware and dinnerware. A light blue backsplash adds a calming touch behind the stainless-steel appliances. A wooden tray holds a bottle of sparkling water and a wooden spoon on the countertop.

Guesthouse in Bethel

5 out of 5 average rating, 16 reviews

Tranquil getaway cottage in charming neighborhood

Escape the city bustle and unwind in the tranquility of The Red Cedar Cottage nestled between Bethel and Newtown, just a short drive from Danbury, CT. Tucked away in a peaceful neighborhood, this fully renovated cottage offers a serene getaway for couples seeking relaxation. Unwind in style on a high-end king-sized mattress in a whimsically curated space designed to rejuvenate your senses. Discover the Red Cedar Cottage and immerse yourself in a tranquil escape from the ordinary.

Guest favorite

An outdoor deck is shown, featuring wooden flooring and a black railing. Lush green trees and a grassy area create a serene backdrop, while a clear blue sky is visible above. A white chair is positioned on the deck, inviting relaxation.

Condo in Hunter

4.9 out of 5 average rating, 89 reviews

Cozy Slope Side Retreat

Hunter Mountain Retreat nestled in the Trailside complex is steps from the slopes. During the ski season, you can walk through parking lot & ski down to get your lift ticket. The Kaatskill Mountain Club is on the opposite side of the trails where you can go for dinner or a drink at the bar. Activities include Zipline, Skyride, Disc Golf, Horseback Riding. Trailside is by far the best & most luxurious place to stay in Hunter. Our rates are very reasonable for the luxury & location.

Guest favorite

The exterior of a two-story house is captured in twilight, showcasing a welcoming entrance with a bright turquoise door. Soft string lights illuminate the path, and two white chairs invite relaxation among seasonal decor, including pumpkins on the steps.

Home in Phoenicia

4.93 out of 5 average rating, 163 reviews

Heart of Phoenicia: Serene. Cozy. Close to all.

"Such a cute place with cabin-in-the-woods vibes but all the conveniences of being in town." What Shannon said in a 5 star review after her stay. I couldn't put it better. Relax and reconnect in this calm and quiet little house nestled in the center of our cool village. You're on the doorstep of hiking trails with BREATHTAKING VIEWS and gorgeous trout streams. Lounge AROUND A GLOWING CAMPFIRE in the back yard with S’mores or SPIN VINYL. On NYC bus route and ski shuttle.

Guest favorite

Farm stay in Kent

4.87 out of 5 average rating, 310 reviews

(°) The Wandering Peacock (°)

The Wandering Peacock is a unique lodging experience. Outdoor spa, with a cedar hot tub and views of the Appalachian Trail, wood-burning sauna with herbs from the garden. The house showcases vintage machinery, a library, an outdoor kitchen with a pizza oven, and much more. Nestled within the forest foothills of the Appalachia trails, this converted barn is minutes away from downtown Kent and just walking distance from Bulls Bridge, the local river, and waterfalls.

Top guest favorite

A welcoming entrance is framed by a decorative sign reading 'WELCOME.' A planter with vibrant flowers adds a colorful touch, while natural stone and gravel pathways lead toward a lush garden filled with greenery and colorful decorative elements.

Guest suite in Newburgh

4.92 out of 5 average rating, 168 reviews

Cozy Country Efficency in Hudson Valley

Spacious and cozy one bedroom efficiency Warm and welcoming, sparkling clean nestled in The Hudson Valley all the amenities of a hotel stay, but the comfort of your own space Farm markets, Wineries, Craft beer through out the area. Historic sights to visit or outdoor activities all around ( hiking, skiing, kayaking, bike riding,etc) Stay in and cook in well appointed kitchenette or sample the large variety of excellent restaurants throughout the region

Superhost

Apartment in Saugerties

5 out of 5 average rating, 3 reviews

Creekfront I Hot Tub I Sauna I Fire Pit I Kayaks

Welcome to Upstate Waterfronts! Looking for a restorative Upstate getaway? This Creekside gem has you covered. - HOT TUB - SAUNA - 3 bedrooms/ 1 full bathroom - Fully equipped kitchen & high-end amenities - Private creek access - including kayaks/vests/paddles - Stunning creek views - including a water facing balcony - 3,000 Arcade games, 75'' Smart TV, endless board games - High-speed WiFi - Prime location - walkable to town/restaurants/shops/beach

Top guest favorite

A serene outdoor deck features a centrally placed Solo Stove surrounded by five wooden Adirondack chairs. The scene captures a tranquil sunset with soft pink and orange hues reflecting off distant mountains and lush greenery.

Chalet in Craryville

5 out of 5 average rating, 13 reviews

Lockwood Lodge Mountaintop

Welcome to our slice of paradise in the Hudson Valley! Enjoy a secluded hilltop home with beautiful mountain and valley views, surrounded by 18 acres of woods. The open floor plan is perfect for cooking or relaxing in front of the fire, and enjoy grilling and the pool when the weather is right. The location is minutes from Hillsdale, and a 15-20 minute drive from Hudson and Great Barrington, with amazing restaurants and activities for every season.

Guest favorite

Home in Tannersville

5 out of 5 average rating, 44 reviews

Luxury Custom Home With Hot Tub Minutes From Town

Just minutes from Hunter Mountain, scenic hikes, and breathtaking Catskill views, our custom home is ideally located—only a block from the best restaurants and shopping in town. With high-end amenities, including a chef’s kitchen, heated floors, fireplace, pool table, entertainment system, and an outdoor kitchen with BBQ, pizza oven, fire pit, and hot tub. Perfect for friends and family, just 2.5 hours from Manhattan—your ideal mountain escape!

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What guests are saying

Heart of Catskills:Pond Views,Backyard Dining+BBQ.

4.95 out of 5 average rating, 20 reviews3 days ago

Came back for another lovely stay! This is the perfect location for outdoor activities and still close to our favs like Hudson & Woodstock. House had everything we needed to stay with two young kids and the backyard can’t be beat! Host is fast to reply and accommodating. Would absolutely recommend!

Home in Round Top

What guests are saying

Garden Retreat Theme

4.8 out of 5 average rating, 108 reviews2 months ago

Everything about this place was wonderful. It was centrally located to Poughkeepsie and was with 15 minutes of everything we hoped to do. The apartment was very clean, well stocked, and private with lots of homey touches that made it extra comfortable. We particularly loved the robes that were provided and the comfortable king sized bed. Delia was extremely responsive and proactive in communicating with us prior to and during our stay. We highly recommend this place for a cozy getaway in the Hudson Valley.

Home in Poughkeepsie

What guests are saying

The Serendipity Spot

4.95 out of 5 average rating, 40 reviews2 months ago

Their place was perfect for a couples weekend getaway. It was very clean, convenient, and we loved our stay there. The overall location and the town itself were perfect for our romantic ski weekend plans. Andrew and Susanne were very kind and inviting and were excellent hosts!

Guest suite in Great Barrington

What guests are saying

Creekside Cottage Retreat: Light, Cozy, Getaway

4.92 out of 5 average rating, 24 reviews6 months ago

Cooper’s airbnb was excellent for the price. It was quiet, clean and cozy. Not the most updated home, but again great for the price. Amazing location. Centrally located and had a gorgeous yard and backyard creek. Cooper was very responsive and helpful! Highly suggest for a casual trip (:

Cottage in Saugerties

What guests are saying

King Bed, Wi-Fi, 2m Ski Resort

4.94 out of 5 average rating, 72 reviews1 week ago

Great find! My husband and I were visiting friends in GB and out dog sitting fell through, we searched around and found this great spot and were able to bring our furry friend with us. We are so glad we found this place! It was quiet and our anxious dog settled in so well - it felt like home to all of us.

Apartment in Great Barrington

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Popular amenities for Millbrook places to stay

Self check-in

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Stay near Millbrook's top sights

Orvis Sandanona Shooting Grounds35 locals recommend

Millbrook Diner34 locals recommend

Canoe Hill32 locals recommend

Babette's Kitchen28 locals recommend

Cafe Les Baux25 locals recommend

Barbaro25 locals recommend

Other great vacation rentals in Millbrook

Top guest favorite

An outdoor deck area is shown featuring several light-colored Adirondack chairs arranged around a stone fire pit. A neatly stacked pile of firewood is positioned against a backdrop of trees, creating a natural setting for relaxation and gatherings.

Home in Millerton

4.97 out of 5 average rating, 181 reviews

Vacation Home In Millerton

Guest favorite

An outdoor deck is shown with a relaxing lounge area, featuring wooden chairs and a grill. A hot tub is positioned to one side, while a fire pit sits in the center. The serene lake view is framed by trees, creating a peaceful setting.

Chalet in Hunter

4.98 out of 5 average rating, 152 reviews

THE LAKEFRONT CHALET - SKI, RIDE, GOLF, BIKE, HIKE

Top guest favorite

A bright dining area features a round white table with metal chairs, positioned near large glass doors that open to a snowy outdoor view. Natural light fills the space, complemented by light-colored walls and a modern pendant light overhead.

Home in Great Barrington

5 out of 5 average rating, 6 reviews

Summer & Leaf Season Rental!

Guest favorite

A glass-top table is set on a wooden deck, accompanied by two wine glasses and a bottle of red wine. Surrounding greenery and distant mountains create a serene backdrop under a partly cloudy sky.

Home in Hunter Mountain, Hunter

4.96 out of 5 average rating, 104 reviews

Private Mountain Lodge, 10mins to Hunter & Windham

Guest favorite

Lush green mountains rise gently against a light blue sky, reflecting softly on the calm waters of a nearby lake. Dense trees line the shore, providing a natural border and a sense of serenity in the landscape.

Guesthouse in Windham

4.97 out of 5 average rating, 100 reviews

Little Bear’s Cottage Great location, cozy & cute

Guest favorite

A spacious wooden deck features a seating area with cozy chairs, a dining table, and an umbrella for shade. Potted plants adorn the space, and a grill is positioned nearby, creating an inviting area for outdoor gatherings.

Home in Woodstock

4.92 out of 5 average rating, 468 reviews

Mountain View Cottage - Sauna, Jacuzzi, Fire Place

Top guest favorite

A spacious outdoor deck features black lounge chairs set beside a low wooden table. A contemporary black chiminea stands as a focal point, surrounded by trees and open land, creating a relaxing atmosphere for outdoor gatherings.

Home in Athens

5 out of 5 average rating, 16 reviews

Lake house with arcade games

Guest favorite

Cabin in Shandaken

4.99 out of 5 average rating, 104 reviews

A Place Called Home in The Catskill

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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.

Places to stay in Millbrook

Top-rated places to stay in Millbrook

NEW - Tranquil Paloma Apartment

Glamping Getaway

Luxury Get-A-Way Beacon/Fishkill

Heart of Catskills:Pond Views,Backyard Dining+BBQ.

Garden Retreat Theme

The Serendipity Spot

Creekside Cottage Retreat: Light, Cozy, Getaway

The Purling Perch

Beacon Creek House

King Bed, Wi-Fi, 2m Ski Resort

Lovely Apt Plus Studio / Half Duplex

Hidden Charm in Hudson Valley

Vacation rentals for every style

Popular amenities for Millbrook places to stay

Stay near Millbrook's top sights

Other great vacation rentals in Millbrook

Your guide to Millbrook

All About Millbrook

The best time to stay in a vacation rental in Millbrook

Top things to do in Millbrook

Franklin Avenue

Innisfree Garden

Dutchess Wine Trail

Destinations to explore