House vacation rentals in Dutchess County

Find and book unique houses on Airbnb

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Popular amenities for Dutchess County house rentals

House rentals with a pool

Guest favorite
A private heated pool area is surrounded by a spacious patio, featuring lounge chairs and a shaded table. The red two-story cabin is visible in the background, with large windows and step access to the pool area. Lush greenery completes the inviting outdoor space.
Home in Stanfordville
4.96 out of 5 average rating, 48 reviews

Charming lakeside cabin with private heated pool

JustinRating, 5 stars7 months ago
My family and I stayed for a long weekend and were so glad that we did! It’s a beautiful cabin, with all the things you need. Kitchen is stocked with essentials, enough bathrooms, beds are super comfortable, hooks to actually hang things like towels, jackets… but we loved the outdoors even more! We walked to the lake, spent way too many hours in the pool, grilled, lounged, made s’mores by the fire pit and watched the beautiful stars at night. Couldn’t ask for more. Paula and her lovely family are SO welcoming it’s crazy. 😂. Hope to be back next summer!
Guest favorite
A charming house with large windows is framed by lush, landscaped gardens featuring various flowering plants. Tall trees provide shade to the front yard, while a pathway leads towards the inviting entrance, enhancing the peaceful and natural setting.
Home in Stormville
4.94 out of 5 average rating, 178 reviews

Private Hudson Valley Country Retreat

MarkRating, 5 stars4 months ago
Place was perfect! Clean & made our Holiday stay in the beautiful Hudson Valley a wonderful experience. We loved the personal touches the house offered and we will be back
Superhost
A spacious backyard area is surrounded by lush greenery, featuring a well-maintained lawn. An above-ground pool with a deck is positioned among the trees, creating a private and inviting outdoor space. A few steps lead up to the pool area, adding accessibility.
Home in Millerton
4.88 out of 5 average rating, 24 reviews

Farmhouse with a view, hot tub, pool, and fire pit

JakeRating, 5 stars5 months ago
Property was good could be a bit cheaper for the value of it . Host is very good at communicating and house was clean . It did the job
Guest favorite
A light-filled living room features a large television mounted on a white wall. Colorful artwork adorns the surrounding walls, complemented by a comfortable sectional sofa. A wooden coffee table sits on a textured rug, and magazines are neatly arranged on the table.
Home in Hopewell Junction
5 out of 5 average rating, 18 reviews

MCM in the Hudson Valley

AlbaRating, 5 stars7 months ago
Beautiful home. Great vibes with cool art and decorations. Nearby the Fishill Farm, and the Beacon metro north. Highly recommended to stay here.
Guest favorite
A spacious two-story house is adorned with winter decorations, featuring dark siding and white trim. Snow coats the ground and branches, adding a serene touch. The entrance is highlighted by a front porch with white railings, surrounded by large windows fitted with seasonal wreaths.
Home in Saugerties
4.98 out of 5 average rating, 60 reviews

Upstate Family-Friendly House w/ Pool Pets Allowed

NasimRating, 5 stars3 months ago
We had a great time at Natalia house, a very big house with a lot to do for my three years old daughter. Will definitely stay here again.
Guest favorite
The spacious backyard features a well-maintained in-ground pool surrounded by lush green grass. Comfortable lounge chairs are positioned on the deck and by the pool. A slide is present for added fun, while the home is partially visible with an elevated deck overlooking the area.
Home in Beacon
4.92 out of 5 average rating, 127 reviews

Beacon Beauty 4/2, Hot Tub,Pool,Wifi,1.5m to Town

GabrielRating, 5 stars1 month ago
Wonderful place to stay in Beacon!
Guest favorite
A two-story house with a light exterior features a spacious front porch lined with railings. Symmetrical windows on the upper level complement the three dormer windows, while a chimney adds a classic touch. A well-maintained lawn surrounds the property.
Home in Clinton Corners
5 out of 5 average rating, 8 reviews

Family home in the country

CeciliaRating, 5 stars6 months ago
We loved staying at Craig’s house. Very warm and inviting with everything you need. Very quiet and peaceful wooded area which we enjoyed very much at the end of the day.
Guest favorite
An open-concept kitchen features sleek countertops and modern appliances, with ample natural light flooding in from large windows. The dining area is visible in the distance, highlighted by a stylish chandelier over a long table, creating a spacious and airy environment.
Home in Rhinebeck
4.95 out of 5 average rating, 189 reviews

On The Hill in Rhinebeck

JenniferRating, 5 stars1 week ago
We had the most amazing and peaceful few days here. Thank you so much for sharing your space and being so accommodating; we absolutely loved your property. I will never forget this special trip- or the amazing memories we made! We are so looking forward to returning ano staying here again soon!!

Weekly house rentals

Superhost
A winter scene is visible through a window, showcasing a snow-covered landscape. Green shrubs peek through the snow, and tall trees are blanketed in white. Soft yellow lights from nearby decorations create a warm glow against the chilly blue tones of the evening sky.
Home in Wappingers Falls
4.76 out of 5 average rating, 110 reviews

Ideal for students and those who travel for work.

JessicaRating, 5 stars3 weeks ago
Overall a perfect place to crash for a night or two when in the area. It was quiet and clean. Our only issue was the bed- it’s very soft so of that’s not for you, you may not get a good night’s rest. But mainly the sides are somewhat sloped so I would start to fall toward the floor unless I pushed myself way back into the center. This may not be an issue for a single person, but for two it was. Otherwise a great spot!
Top guest favorite
The rustic cabin is nestled among trees, with a stone foundation and wooden siding. A screened-in porch extends from the front, surrounded by natural greenery. A stone pathway leads towards the entrance, emphasizing the cabin's serene and secluded setting.
Home in Cold Spring
4.89 out of 5 average rating, 45 reviews

Cabin with a View

TerriRating, 5 stars1 week ago
Ellen’s place was beautiful and cozy. The kitchen worked perfectly and even though it was April it was still a bit chilly so the wood stove was a welcome amenity. The shower was great and there was a soaking tub. It was quiet and beautiful. We like all the art and it was very homey.
Guest favorite
A modern kitchen features stainless steel appliances and gray cabinetry, creating a stylish workspace. A large island with a marble countertop offers ample prep space. Natural light floods the area through a glass door, which leads to the outdoor space. A vase of flowers decorates the dining table.
Home in Beacon
4.93 out of 5 average rating, 40 reviews

Modern home w/creek view, steps to town & mountain

JudiRating, 5 stars3 months ago
We talked my Pop into his first vk in 10 years. He’s 85 now and doesn’t like to leave the comforts of his home. He also has no idea what an Airbnb is. So this will be a review from his quotes : “Oh so it’s a house?” “This is a really nice kitchen”. “They keep it clean. It feels like a hotel”. “ “I love this en-suite” “I love they let dogs here. I get to be with my grandson” ( grandson= our golden doodle). “This fridge is smarter than me” (it beeps if you leave it open). “Huh. This is so close to everything. That makes everything so easy”. In all my we had a wonderful stay. It felt homey and comfortable. Thank you
Superhost
The exterior of a modern home is shown, surrounded by a lush, green lawn and trees in the background. The structure exhibits a mix of large windows and unique architectural elements, including a cylindrical section. A stone path leads to the entrance, adding character to the landscape.
Home in Wappingers Falls
4.89 out of 5 average rating, 113 reviews

LivingUPstation

MichelleRating, 5 stars3 months ago
Ari’s home was cozy and quiet. We had all we needed for a relaxing writing retreat. Spearate spqces to focus and a table big enough to gather at for meals. The whole space had a peaceful and serene vibe and was a great escape from the city. Would def recommend.
Superhost
An open-plan dining area features a dark table surrounded by four chairs, all set on a checkered rug. Exposed brick walls and wooden ceiling beams are visible, while a sleek kitchen with modern appliances can be seen in the background.
Home in Kingston
4.87 out of 5 average rating, 115 reviews

Historic 1800s Kingston Waterfront Townhouse

EvelynRating, 5 stars3 weeks ago
Perfect home for a my husband and toddler. We had the best time spending a week here. It's spacious and cozy. Walkable to a lot of great spots for any meal of the day. It's quiet and just the perfect getaway we needed upstate!
Guest favorite
Home in Marlboro Township
4.99 out of 5 average rating, 190 reviews

Historic 1873 Farmhouse Near Vineyards & Orchards

JessicaRating, 5 stars1 month ago
Mark & Whitney's place is absolutely gorgeous. It is much much bigger than it looks in the photos, but it is just as gorgeous if not more. I highly recommend staying here, I stayed for a little "staycation" and it was just perfect.
Superhost
The living area features a woodstove, complemented by comfortable seating arranged around a low coffee table. A cozy ambiance is created by the arrangement of natural materials. A glimpse of the kitchen and dining area can be seen in the background, enhancing the open layout.
Home in Rhinebeck
4.83 out of 5 average rating, 267 reviews

Private Lakefront Bungalow

JosephRating, 5 stars2 weeks ago
We loved the place! My fiancé, Gloria and I wanted a little get away for the weekend for her birthday. This place was perfect. 1-2hours drive from the city. The lake was amazing and it was very private. We had a great time. We did canoeing too. It was fun! We hope to be back again in the future. Thank you, Robin!
Superhost
A spacious living room features a large sectional sofa with a soft throw blanket and decorative pillows. Two blue accent chairs are arranged beside a wooden coffee table on a textured rug. Exposed wood beams adorn the ceiling, and a flat-screen television sits against the wall.
Home in Saugerties
4.91 out of 5 average rating, 190 reviews

New 3b House in Saugerties Village/4 mins to HITs

EvonRating, 5 stars5 days ago
Really enjoyed our stay in Saugerties! The house was super clean and in a great spot—just a short walk to town. We had fun exploring the shops and grabbing food at local restaurants, and the park nearby was perfect for the kids. Would totally stay here again!

Private house rentals

Guest favorite
An open-plan living area features original wooden beams in a minimalist design. A modern fireplace is centered against a grey wall. A sectional sofa and a dining table are positioned, with ample natural light flooding through large glass windows on two sides.
Home in Hyde Park
4.98 out of 5 average rating, 50 reviews

Modern Barn With Hot Tub + Games Room!

CemRating, 5 stars3 weeks ago
Super nice hosts. Beautiful farm house. Would recommend and stay again.
Top guest favorite
A sunlit enclosed sunroom features a curved sectional sofa adorned with decorative pillows and a central wooden table. Large windows invite natural light, offering views of the backyard. A rocking chair and potted plant add a cozy touch to the inviting space.
Home in Dover Plains
4.93 out of 5 average rating, 30 reviews

Hillside Grove

StefanieRating, 5 stars1 month ago
Jennifer’s place was amazing! The house is super clean, very neat and organized, and comfortable furniture. It is exactly as described and Jennifer is very responsive. Definitely worth a repeat trip!
Guest favorite
An aerial view captures the home nestled among vibrant autumn foliage. The white colonial cottage is surrounded by sprawling greenery and trees displaying fall colors, offering a serene setting in the countryside. The long driveway leads to the entrance, enhancing the home's secluded charm.
Home in Stanfordville
4.84 out of 5 average rating, 38 reviews

White House On The Hill w/Chickens & Duckies

DaltonRating, 5 stars12 months ago
We had the absolute best stay at Jeanie’s home! It was beautiful, spacious, and so well decorated, and the property couldn’t be more peaceful. The chickens and ducks in the backyard were so fun to watch, and really made the stay so magical. Jeanie was so helpful too, with lots of local recommendations and made our whole trip so easy! The house oozes with charm and character, and we couldn’t have loved it more!
Guest favorite
The historic family home is set on a neatly manicured hill, surrounded by lush greenery. The two-story structure features large windows and a welcoming porch, while the expansive lawn offers ample outdoor space for relaxation. Bright sunlight enhances the inviting atmosphere.
Home in Milton
4.75 out of 5 average rating, 178 reviews

Historic 1 BR Family Home Near Buttermilk Falls

DianeRating, 5 stars5 days ago
What a perfect place to stay! We were very comfortable in Hazel’s little retreat… we slept well in the king sized bed, had plenty of hot water, loved the bucolic green space and the creek nearby. Our dogs had great walks under the canopy of huge trees surrounding the property. I especially enjoyed watching and hearing the ducks, geese and swans across the street as they paddled to the pond! Thank you, Hunter for providing a perfect getaway spot for your guests!
Guest favorite
A welcoming living area features a black sectional sofa adorned with decorative pillows. A wooden coffee table is positioned in front, while a large wall clock and TV are mounted above a simple fireplace. Natural light filters through two windows, enhancing the space.
Home in Beacon
4.92 out of 5 average rating, 97 reviews

Beacon 2BR house w/ backyard, easy walk to main st

SarahRating, 5 stars1 week ago
We stayed here for our wedding weekend and couldn’t have asked for a better experience! The house was cute, clean, and comfortable - exactly what we needed during such a busy and exciting time. We especially appreciated how close it was to everything; it made it so easy for us to get around without stress. Eva was wonderfully responsive and kind, answering any questions quickly and making sure we had everything we needed. It truly felt like a home away from home. We’re so grateful to have had such a great place to stay during such a special moment in our lives!
Superhost
A spacious wooden dock extends into the shimmering water of the Esopus Creek, featuring several blue Adirondack chairs and a small table. Sunlight reflects off the water's surface, enhancing the peaceful setting surrounded by greenery.
Home in Saugerties
4.79 out of 5 average rating, 24 reviews

Stylish Waterfront Escape on the Esopus Creek

NicoleRating, 5 stars4 months ago
We had a great stay at Rupert’s house. As other reviewers have stated, there is a train that passes by the house. Each day, it passed 2-3 times but it wasn’t terribly noisy. We never saw the tenant who also lives on the property. We didn’t realize that the tenant’s home was connected to the house we rented. It didn’t bother us but thought I’d share. Rupert was very responsive when we had questions. His home was a wonderful place for us to spend Thanksgiving. There was more than enough space for my family of 5. We especially loved the dining room with the long table and views of the Esopus Creek, which runs right behind the house. Given the weather, we didn’t spend time down there but it was certainly lovely to look at. We would definitely stay there again in the future.
Top guest favorite
A modern kitchen is depicted, featuring stainless steel appliances and a large island with a wood accent. Green cabinetry complements the light countertop, while natural light filters in through the window. Wood flooring extends throughout the space, enhancing the contemporary design.
Home in Pine Plains
5 out of 5 average rating, 13 reviews

Family-Friendly by Polo + EV Chgr

VivianRating, 5 stars3 months ago
We truly enjoyed our stay at Daniele’s during a weekend ski trip! The home was exactly as described and we did not run into any major issues. The only thing I’d note is for a group of 8, we did not have enough toiletries (i.e., shampoo, body wash) or household supplies (i.e., paper towels) near the end. Aside from this minor concern, we had a wonderful stay; Daniele was extremely responsive and accommodating with our requests. Thank you so much!
Guest favorite
Home in Kingston
5 out of 5 average rating, 5 reviews

Double the Fun: Two Houses, Shared Yard & Fire Pit

HannahRating, 5 stars3 months ago
We had an easy and wonderful stay at Matt’s! We were a group of 2 couples and 1 additional adult and booked both houses. Everyone had enough space and the house was clean and welcoming. The house is located close enough to the highway so it’s easy to get to many nearby towns. We loved the two house configuration, it worked out perfectly for our group. Would highly recommend!

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