Holiday rentals in Dutchess County

4.97 out of 5 average rating, 63 reviews

Chalet in Carmel Hamlet

Secluded Lakefront Chalet-Firepit&yard Dogfriendly

ElizabethRating, 5 stars2 weeks ago

THE best Airbnb rental in the area, hands-down. I was fortunate enough to stay here a little bit over a week, and had such a great experience. Going through a turbulent time in my life and Wylda’s home brought me much-needed peace and comfort. The location of her house (last one on the street) makes it very private, the views were so beautiful, love the layout of the house (a few steps up from the main living area as a smaller entertainment area with a couch, TV and desk overlooking the lake) that it gave me a beautiful backdrop as I did work, everything is very clean, very comfortable bed, and absolutely love the decor (you can tell the host as well traveled). I will be recommending this house to any friends or family that come to visit the area. And I’ve already booked another stay very soon!

5 out of 5 average rating, 3 reviews

Flat in Saugerties

Esopus Creekfront I Family I Fire Pit I Kayaks

JulietteRating, 5 stars5 months ago

We had a great time staying in this beautiful and comfortable space. It had everything we could hope for and was perfectly clean. The air felt and smelled fresh as we walked in the door. It was spacious and well appointed with extras like condiments, games and puzzles. There was a dog gate and potty bags in case we brought our pets. We didn’t bring ours this time but might in the future because we definitely want to stay here again. There were plenty of clean linens and the shampoo, conditioner and body wash were great. The coffee was delicious and there was tea too. We didn’t use the air fryer, but it was nice to have that and the gas stove in case we wanted to cook. Thank you for a great stay!

4.76 out of 5 average rating, 125 reviews

Home in Poughkeepsie

Newly Renovated & Comfortable Home-Vassar/Marist

GeneRating, 5 stars2 months ago

Charlotte’s place was clean, cozy and comfortable. The bed was comfortable and there were plenty of towels. Lots of widows to let in the daylight; with curtains to close at night. We stayed during some cold snowy weather and the house was warm and not drafty. The snow was shoveled away first thing in the morning. The keyless entry (electronic keyboard) sometimes requires multiple attempts. Would likely stay there again.

4.95 out of 5 average rating, 111 reviews

Home in Lake Katrine

Waterfront 3BR Home in Hudson Valley, Catskills

NathanRating, 5 stars3 months ago

This place was a breath of fresh air. I've noticed a trend on AirBNB of rentals that are obviously flipped investment properties with no character and no evidence of life: this place is the opposite! Charming, comfortable, with hosts who actually know the area and live in the area. This is a great family option when visiting the surrounding Hudson Valley towns. I hope I can get back here soon!

4.93 out of 5 average rating, 360 reviews

Guest suite in Millerton

Romantic Sunset-50 mile view of Hudson Valley!

AnkithaRating, 5 stars1 week ago

Juliana and Paul were very friendly and their response is very quick so it was very helpful if we were unclear about anything ! The place is exactly as they have described, so glad they were specific in their instructions about toiletries so we were able to pack everything beforehand . Definitely recommend this place if you’re looking for a peaceful gateway:)

4.98 out of 5 average rating, 117 reviews

Cottage in Pawling

Twin Lakes Designer A-frame Stone Cottage

AsiaRating, 5 stars2 weeks ago

I had the most amazing stay at this cabin! The interiors were absolutely gorgeous—so thoughtfully put together, and everything was spotless and perfectly organized. You could really tell a lot of love went into every detail. The hosts were incredibly kind and provided clear, detailed instructions, making everything super easy and stress-free. The setting was beautiful and so peaceful. My favorite part was sleeping in the loft under the stars! The huge windows made the space feel so open and airy, with tons of natural light during the day. It was such a dreamy and relaxing getaway, and I honestly can’t wait to come back!

4.77 out of 5 average rating, 107 reviews

Flat in Kingston

In the Heart of Kingston

ScottRating, 5 stars1 week ago

I was worried based on others reviews but the place was fantastic. Toasty with freezing temperatures outside. The bed was quite comfortable. The Internet was fast enough for my work calls. There were some great restaurants that were walkable. Carin had great suggestions — I’d add Monkey Joe Roasting company for a coffee shop rec

Holiday rentals for every style

Get the amount of space that is right for you

Cabins

Kick off your hiking boots at these rustic lodgings

Flats

Convenient locations with everyday essentials

Cottages

Quaint homes, peaceful surroundings

Popular amenities for Dutchess County holiday rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in Dutchess County

4.97 out of 5 average rating, 174 reviews

Home in Millerton

Vacation Home In Millerton

MichaelRating, 5 stars1 week ago

Nice home. Comfortable, spacious and has the needed amenities. Recommended and would gladly stay again.

5 out of 5 average rating, 111 reviews

Home in Saugerties

Saugerties Log Home W/ Game Room

YllRating, 5 stars1 week ago

I stayed at Vince’s place with a group of my 6 best friends for my bachelor weekend. The home was the perfect place for the occasion - super nice and clean AirBnB, tons of comfortable beds, the entire downstairs was an awesome game room, speakers in every room. We had an unforgettable weekend - would definitely recommend this place to others and we are even considering a return trip in the future! Cheers!

4.88 out of 5 average rating, 24 reviews

Home in Millerton

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

JakeRating, 5 stars4 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

Place to stay in Saugerties

4.94 out of 5 average rating, 69 reviews

211 Main, located in the center of the village.

SarahRating, 5 stars6 months ago

Wonderful stay, very nice, clean, comfortable, large apartment. I've stayed in a lot of local air bnb's, and this place is one of the top for sure. No issues, communicative host, had the a/c on for us so apartment was cool when we arrived. Cold bottles of water in the fridge. Would definitely stay again if it were available.

4.92 out of 5 average rating, 12 reviews

Home in Putnam Valley

Lakehouse Woodland Retreat

MildredRating, 5 stars5 months ago

My family and I really enjoyed Elizabeth property very comfortable and quiet, we definitely thinking about coming back soon.

4.92 out of 5 average rating, 95 reviews

Home in Beacon

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

HeatherRating, 5 stars1 week ago

This was a great location and great stay for my weekend getaway with friends for my birthday. The layout was not what I expected but overall worked for our purposes. Location was most important and this definitely delivered! Overall really great stay and Eva was very responsive!

4.84 out of 5 average rating, 103 reviews

Flat in Beacon

Lovely 2 bed, 2 full bath. & private yard getaway

BrynaRating, 5 stars2 months ago

Lil's place was very nice and in a great part of Beacon. It was close to some great hiking trails, and just a 5 minute drive from the downtown area. Lil was very responsive to any questions and we would definitely stay there again.