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

Enchanted Escape | POOL, LAKE, Concierge Services
I had an incredible experience staying at Sunny's place! From the moment I arrived, everything was exactly as described – clean, comfortable, and thoughtfully set up. Sunny was an outstanding host: friendly, responsive. The location was perfect, the amenities were top-notch, and you can tell that Sunny really cares about his guests’ experience. I truly felt at home during my stay. I would absolutely stay here again and highly recommend Sunny’s Airbnb to anyone looking for a relaxing and hassle-free trip. Thank you, Sunny!

Bluestone Escape - Where everyone is at home.
Billy and Rhobin were so helpful and easy to communicate with. The house was so comfortable and peaceful. The property was lovely! 5 Stars all around! Thank you for a fantastic stay!

4Br Mountain Brook House on 130 acres w/ trails
We were 5 girlfriends staying at this property. Each one of us loved everything about it . Perfect location !

Hudson Valley Retreat w/ Pool
We had a wonderful stay at Zahra’s home. The home was just as described and was the perfect cozy sanctuary we needed. Nicely located and close to all . Appointed with all one could want for a month long stay. Zahra is truly a five star host and went well above, with quick responses and furnishing us with a tree for the holidays. Can’t recommend enough if you’re planning a trip to the Hudson Valley area.

Hudson River views with pool and hot tub
I wanted a peaceful, relaxing trip with all my girlfriends and that’s exactly what we got!! The place was beautiful with amazing amenities and an even better view of the water. The pool was the perfect size for our group (9) and the jacuzzi was also great. The house and rooms were very spacious, and finally, the host Marisa was super responsive and helpful. Overall a very lovely experience, would definitely book again!

Beacon Beauty 4/2, Hot Tub,Pool,Wifi,1.5m to Town
This place has everything we were looking for - pool, hot tub, and a yard for our dogs. This is the second time we stayed here, and it was perfect once again!

On The Hill in Rhinebeck
Loved this Airbnb! It was spacious and comfortable, this house in particular had really beautiful plants that enhanced the space even further. I love that we were able to connect to a Bluetooth speaker with ease. The location is close to really yummy restaurants and a park that we both drove and were able to catch an uber to. Also, I was able to cook a Sunday supper and I had all that I needed as far as pots and pans were concerned. I would book again for sure.

Peaceful Hudson Valley Getaway House
My family had a great stay at Veronika’s home. It was comfortable, spacious, and conveniently located. The home had everything we needed, including essentials for our toddler. Veronika was easy to communicate with and responded promptly.
Weekly house rentals

Hudson Valley Boutique Airb&b
It was a great stay and beautiful home. Really appreciated the ease of entry and amazing scenery.

3000 sq ft Poughkeepsie home with chef's kitchen
Bruce is a very friendly person, responding to my messages within in minutes

The Gatehouse in Historic Hyde Park
This was a wonderful find and stay. We are very thankful to have found it. The attention to detail in this home is beyond appreciated. From the light switches to the furnishings and beyond it was perfect for us. Thank you so much. We will definitely return when in area.

Beautiful, Spacious, 5 Acre Family Retreat
Lovely place. There were 7 ladies celebrating their 40th college reunion. Spacious and clean and beds were comfortable (we did double up on two beds.) Great place for relaxing and catching up.

Historic Cottage w Brand New Hot Tub and Game Room
Fantastic place. All the amenities were exactly what we were looking for. Would definitely stay again.

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.

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.

Mountain Top Retreat
Andre's place was a beautiful home away from home. Sparkling clean inside and surrounded by serene natural beauty outside. Bring your bug spray if you're going for a hike!
Private house rentals

Farmhouse Oasis in the Hudson Valley, Stream Views
Booked for my crew while working in the area. What a beautiful place to relax after a hard day's work! The place was spotless, grounds beautiful and picturesque, and plenty of space to relax. Kitchen was well equiped for group dinners. Hosts we're friendly and responsive. Highly recommend!

Arts Estate | Walk to Cafes and Shops
This house is amazing and the garden is breathtaking. The host was attentive and communicative and m left some very thoughtful little surprises for us. The neighborhood is quiet and easy to walk to shops, restaurants and the waterfront. My family of 6 fit comfortably and everyone had their own space. I even took a cold plunge in the claw foot tub in the yard! We are already looking into when we can come stay here again.

Hyde Away
Morgan’s place was immaculate and you felt right at home. The house was spacious yet cozy! Another bonus for us we have an electric vehicle and it was nice we were able to charge it at the house. Morgan is an exceptional host and if we are ever in the area we will stay here again! Thanks again for sharing your lovely home!

A Modern Retreat
Vik’s home was perfect for our weekend trip to the Millbrook area with our kids (aged 6 and 4). Clean, well appointed, and cozy, we enjoyed our stay!

The Cherry House
House was very clean. Beds were comfortable. Kitchen was well equiped. We did not have a chance to use outside amenities due to extreme heat and traveling with elderly parents. Definately appreciated the air conditioning. We enjoyed our 2 night stay.

Salvato Mill-designer escape w/ private waterfall
Ariana’s place is absolute magic! The mill is a truly unique property - the type you’re always looking for on Airbnb but rarely find - in the most tranquil of settings. Just wish we could’ve stayed longer. We’ll be back!

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.

Barn House Near Rhinebeck w/ Hot Tub!
Caroline was a great host, super responsive. It was snowing a lot during our stay and she let us park one of our cars in the garage. A fuse also went out when we were using a hair dryer and she was able to immediately send someone to the house to fix it right away. The house was beautiful and we would stay here again, already making potential plans for the summer. We’ve already recommended it to other friends! We had a great time cooking, using the hot tub, lounging around and exploring Rhinebeck which is not far from the house. Not far from Hudson either! Perfect location.
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- Hunter Mountain
- Belleayre Mountain Ski Center
- Minnewaska State Park Preserve
- The Kartrite Resort & Indoor Waterpark
- Thunder Ridge Ski Area
- Taconic State Park
- Resorts World Catskills
- Zoom Flume
- Hudson Highlands State Park
- Walkway Over the Hudson State Historic Park
- Bash Bish Falls State Park
- Catamount Mountain Ski Resort
- Kent Falls State Park
- Brotherhood, America's Oldest Winery
- Rockland Lake State Park
- Windham Mountain
- Sterling Forest State Park
- Norman Rockwell Museum
- Beartown State Forest
- Mohawk Mountain Ski Area
- Mount Southington Ski Area
- Hancock Shaker Village
- Mount Peter Ski Area
- Hook Mountain State Park
- Things to do Dutchess County
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