
House holiday rentals in Millbrook
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Top-rated house rentals in Millbrook
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Popular amenities for Millbrook house rentals
House rentals with a pool

Private Hudson Valley Country Retreat
This beautiful property has a special place in our hearts. We stayed in the A frame during COVID and we always wanted to come back. This time we stayed in the main house and it was phenomenal. Wish the weather was better for us to use the pool, but next time! It well worth the price. Only an hr from the city and it feels like a full vacation. Wonderful way to lose time time for a few days. We will be back!

midcentury mod * POOL * walk out trail to mohonk
The house met all expectations everything is stylishly done, and the host is incredibly responsive and helpful 🤍

Hudson Getaway w/ Hot Tub + Fireplace on 20 Acres
Very enjoyable time here! Instructions, accommodations, and overall experience was perfect!

Scenic River View Escape | New Paltz
I spent my birthday at this beautiful house and couldn’t have asked for a better experience. The place was spotless and full of natural light, with lovely views that made the stay even more special. The atmosphere was peaceful and clean, and the house had everything we needed for cooking and relaxing. I truly felt at home and appreciated all the thoughtful touches. Highly recommend for anyone looking for a cozy, well-equipped getaway!

Little owl Japanese teahouse: pool is OPEN
My husband and I had a wonderfully relaxing time at the Little Owl Teahouse. It’s a cozy and well-outfitted cabin with a super comfy bed and a great leather reading chair. Drank lots of the delicious mountain well water. Made breakfast in kitchen — love the pans and electric cooktop. Short drive to Woodstock for dinner. And oh the beauty of the surroundings - scenic views everywhere. Our two little doggies were happy to romp in the fenced in yard. Little too chilly when we were there but pool looks so appealing. Lisa is a proactive and super responsive host.

Modern Barn on 12 acres w Sauna, FirePit+swimming
Cozy home, on a beautiful property. The natural pool is really special, and we loved staying here. Hope to be back.

Harrison Field Pool SummerUpstate GetAway Hiking
We had a great stay at Nathan’s place. The playroom was great for our kids and we all enjoyed the pool. The view was also beautiful. We will definitely be back!

Peace & Privacy - High Falls (hot tub & salt pool)
Amy & Sean's place was perfect. We choose it for its proximity to our wedding venue and couldn't be happier. The HOT Tub was just what we needed after a long day of preparing for our wedding. 100% recommend and will definitely consider staying again.
Weekly house rentals

Roam the 10 Acres of This Charming Country Retreat
We were visiting Poughkeepsie for our daughter’s graduation and wanted a hassle free place to stay so we could focus on the momentous occasion. Anne and Tosso’s place was perfect - away from the city and yet connected to salons and local restaurants - and self-sufficient. In no time, we found ourselves enjoying the tall trees, the walkways, the hammock, the friendly deer visits and the various nooks and corners of their extremely spacious and comfortable home. Moreover, since the hosts don’t live too far from the house, it’s easy to reach out to them if and when needed. We are truly grateful for your gracious hosting, Anne & Tosso

Hillside Grove
We had a wonderful stay! The place was clean, comfortable, and exactly as described. It was perfect for the whole family. The host was very responsive and helpful throughout our stay. Highly recommend—would definitely stay here again!

Beautiful sun filled cottage in the woods
We hosted a Friendsgiving here and it was so lovely. From the falling snow to the open concept, it was a wonderful gathering abode for the holiday. Thank you!

Enjoy the Hudson Valley at our quiet Farmhouse!
We stayed at Stephen’s place for our daughter’s graduation from Vassar. Our group of seven felt very comfortable there. The house was so comfortable, and we were all were able to relax and hang out together. Thanks again!

Nature lover’s retreat in NWCT, breathtaking views
Kellen and Samantha's home and property are very special--a wonderful location for a restful retreat in nature that is also a short drive to several charming towns in northwest Connecticut. The hilltop site offers breathtaking views of surrounding mountains, valleys, and forest. The residence sits atop a long driveway off a gravel road so is serenely quiet and private. Inside, the space was immaculate, thoughtfully designed, and very comfortably furnished. The shower, bed, towels, and linens were all particularly fantastic, as was the full kitchen which allowed us to cook nightly. The area is exceptional for hiking, culinary delights, and all sorts of shops. And our hosts were proactive, helpful, and clear in all of their communications. We really loved staying here, as did our dog, and we hope to return. Highly recommended!

Hidden Country Escape - 1.5 HRS From NYC
This was our first stay but will not be our last. Excellent host! Everything was as stated in the description. Comfortable bedding and all the amenities needed. Very clean and organized. Highly recommend.

Country Cottage: Hudson Valley - Millbrook Area
This is a lovely stay nestled in the heart of Dutchess County. It is a short drive to Millbrook and not too far to Poughkeepsie and other surrounding towns. The home was clean and well kept. It has all the items you may need. The yard and spacious and surrounded by mature nature on a quiet road. An alpaca farm is just up the road and Zoe's Ice Cream Barn is around the corner. We would surely stay here again.

Salvato Mill-designer escape w/ private waterfall
we had a wonderful stay at Salvato Mill, a truly unique and special place. it was exactly as described, so peaceful and rustic. we really enjoyed it!
Private house rentals

Private retreat on 12 acres w hot tub and bbq
The LaGrange Farmhouse is lovely! The grounds are beautiful and well-maintained. The house itself is charming and well appointed. The photos do not do justice to beautiful home and property! Brandon is a very responsive, respectful host.

Historic Cottage w Brand New Hot Tub and Game Room
We had a great time! Loved the dear old house with modern amenities. Host was very responsive. We look forward to going back! ❤️

Stunningly Designed Historical Icon w/ Hot Tub
Still gleaming from an unforgettable stay at Willow Vale which is hands down a 5-star gem! The design of the house is one-of-kind where every detail piques curiosity and wonder. The library stole our hearts from the start, brimming with an extensive book collection and unique treasures. We sat by the fire here every night. The sunroom was the perfect daytime spot where we napped, worked, ate and played games. It’s impossible not to fall in love with the kitchen…we cooked almost every meal. Enjoying the hot tub under the stars was a highlight. We loved that there was a telescope and took advantage of it. The river was serene with a perfect swimming hole…and cold plunge! The house is secluded and there is so much to do nearby. It’s truly the land of hidden gems. Stissing House for dinner is a MUST. As their home might suggest, Matt and Whitney go above and beyond as hosts. They made this family vacation special for us in every possible way. We cannot wait to return!!!

Creekside Couple's Retreat w/Hot tub, Sauna & More
My husband and I were blown away by the beauty and thought that was put into this private destination. The moment you step on property, the freshness of the air and sounds of the creek are immediately calming. Diana was incredibly nice and very communicative before and during the entire stay. Activities: The sauna, creek, hot tub, pizza oven, grill, fire place/pits, hammocks- the amenities are amazing and unlike any other Airbnb I have ever been in before. So much that besides a quick dinner out one night (12 min away) and a nice walk around the Mountain Top Arboretum with our dog, we wanted to spend our time at the property. We called it our personal sanctuary spa!! The home: The home style is minimalistic but homey and every single item is top notch quality. There are no shortcuts- the entire place is a work of art. The bedroom and bathroom inspired me to reanalyze my own bedroom style. Thank you for upping the Airbnb game!! Can’t wait to come back to this magical spot! ✨

Contemporary Hudson Valley home
The house was awesome! We loved the decor and everything we could possibly need was provided. It was great dealing with Evan. He was responsive and helpful.

Hudson Riverfront Mid-Century Modern Home
A beautiful, comfortable house right on the Hudson with stunning views. We loved watching all the life on the river, herons and loons and ducks, as well as boats from tiny crafts to massive barges. There are great hikes just a short distance away. It is a perfect place to rest, write, draw, and make music.

Hidden Charm in Hudson Valley
Totally recommend this Airbnb as a weekend retreat from NYC. Fairly priced, great host, spacious house and surroundings, only 1.5hrs away from NYC. First off, it sits on a 40 acre lot with a gated driveway - perfect for privacy and a sense of seclusion. The house itself is a bit dated, but spacious and well equipped with kitchen amenities and games/activities. The real winner is the outdoor space, with a large mowed backyard (and grill, fire pit, picnic bench, etc.). The house also sits on top of a hill with beautiful views of sunsets and the neighboring hills. The host was great, very responsive, allowed us to check in early. All in all, happy to recommend it.

Rhinebeck Retreat w/ Lake Views near Omega
Heather‘s place was absolutely immaculate! Beautifully decorated, the most comfortable beds, linens and towels imaginable. Peaceful tranquil I especially enjoyed the yoga room. I will definitely go back again and I highly recommend this place to anyone looking for something peaceful and beautiful.
Destinations to explore
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- Hunter Mountain
- Belleayre Mountain Ski Center
- Minnewaska State Park Preserve
- Thunder Ridge Ski Area
- The Kartrite Resort & Indoor Waterpark
- Taconic State Park
- Catamount Mountain Ski Resort
- Zoom Flume
- Windham Mountain
- Kent Falls State Park
- Rockland Lake State Park
- Walkway Over the Hudson State Historic Park
- Bash Bish Falls State Park
- Sherwood Island State Park
- Hudson Highlands State Park
- Brotherhood, America's Oldest Winery
- Sterling Forest State Park
- The Stanwich Club
- The Connecticut Golf Club
- Norman Rockwell Museum
- Sleeping Giant State Park
- Mohawk Mountain Ski Area
- Beartown State Forest
- Yale Golf Course