Cottage holiday rentals in Dutchess County

Find and book unique cottages on Airbnb

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Popular amenities for cottage rentals in Dutchess County

Cottage rentals with a hot tub

Guest favourite
Cottage in Kingston
4.95 out of 5 average rating, 57 reviews

Charming Cottage in Kingston - License #002740

LarsRating, 5 stars2 months ago
Wonderful space to spend time in.. Extra cozy and quiet. Easy walk to several stores/resaurants.. Appreciate the large Televisions as it was March Madness/Basketball time, so that was a nice plus that you dont find in some places. Overall it was extremely pleasant stay for myself and my Girlfriend for a long weekend..
Superhost
Cottage in Cold Spring
4.78 out of 5 average rating, 230 reviews

Cozy Countryside Cabin Spa/Fireplace/Enclosed Yard

EdgarRating, 5 stars4 days ago
Very nice peaceful places and very good service i will definitely be back soon, thank you
Guest favourite
Cottage in Red Hook
4.9 out of 5 average rating, 348 reviews

Goose Landing Cottage by the lake with NEW Hot Tub

LeahRating, 5 stars1 week ago
Ellen's cottage was the perfect place for me to unwind and enjoy a peaceful vacation. The surrounding area was serene and the lake was such a bonus! The cottage had everything I needed and more and the bed was so comfortable which isn't always the case with airbnbs so I was thrilled. Ellen was always very sweet and responsive and all around a great host. 10/10 recommend this spot to anyone! Thanks for a great stay!
Top guest favourite
Cottage in Hyde Park
5 out of 5 average rating, 64 reviews

Peaceful Hudson Valley Retreat with Hot Tub

CindyRating, 5 stars2 weeks ago
Beautiful, well-appointed home in a great location - close to all historical sites and the Culinary Institute of America in Hyde Park. We enjoyed the home's fire pit and peaceful location. Lots of room for 8 adults for a family get-together.
Superhost
Cottage in Red Hook
4.9 out of 5 average rating, 206 reviews

LAKE COTTAGE WITH HOT TUB - PAINTED TURTLE

JenniferRating, 5 stars3 weeks ago
Thank you Ellen for the easeful stay at your cottage with clear instructions. The surroundings are beautiful. We saw an eagle at the lake!

Pet-friendly cottage rentals

Guest favourite
Cottage in Esopus
4.96 out of 5 average rating, 24 reviews

West Park/ Esopus Cottage - 2 King /1 Queen bed

MeghanRating, 5 stars2 weeks ago
My friends and I stayed at Onora’s home for a wedding at Red Maple Vineyard. It was a perfect location and beautiful home, and plenty of space for my group of 5. I’d highly recommend!
Guest favourite
Cottage in Esopus
4.94 out of 5 average rating, 90 reviews

West Park Cottage | Hiker's Paradise

AnneRating, 5 stars5 days ago
Great place. Very clean and pretty. Good location. Not as tucked into woods as I imagined but not in main road and near hiking and restaurants. Would stay again
Guest favourite
Cottage in New Fairfield
4.97 out of 5 average rating, 36 reviews

Sunset Cabin Modern Home Kayak FirePit Lake Access

AlendaRating, 5 stars2 weeks ago
Great place that looked just like the pictures! We would definitely rent again. Brad always responded right away to my messages.
Top guest favourite
Cottage in Ulster Park
5 out of 5 average rating, 53 reviews

Nestled in Hudson River nature park near Kingston

AndreaRating, 5 stars2 weeks ago
We had the most beautiful stayed at Toby’s Airbnb. We go upstate every other weekend to explore new towns and so far this has been the best Airbnb we have stayed at. We were traveling with my mom and the two room home was perfect for us to spend a cozy rainy day cooking, waking up in the morning for a hike by the river. The house is beautifully designed, super organized and exceptionally clean. Will definitely stay again next time we are upstate :)
Superhost
Cottage in Pleasant Valley
4.86 out of 5 average rating, 29 reviews

Red House in the woods

ReneeRating, 5 stars3 weeks ago
Helene was a great hostess. Perfect location just outside Arlington. We went to be close to Vassar and it was close enough. Yet also far enough to get out of the fray. The little town had everything we needed. Grocery and Dollar General nearby. Photos and descriptions are spot on. You are in the country! Peaceful and beautiful. Good Wi-Fi ! Home is clean with updates. Would definitely recommend and stay again. We appreciated the special touches of coffee pods and laundry available! We saw baby woodchucks! Helene was very communicative and I appreciate that! Thanks for sharing your home, Helene.
Top guest favourite
Cottage in Kingston
5 out of 5 average rating, 27 reviews

Empire Bicycle Lodge

MarciaRating, 5 stars2 weeks ago
Samantha’s place was great and I would stay there again. It’s clean and comfortable with two separate sleeping spaces, so great to share with a friend or family members. Proximity to the different zones of town is very convenient. The neighborhood is walkable / residential with some local amenities right nearby. The outdoor eating zone is a bonus !
Top guest favourite
Cottage in Red Hook
4.99 out of 5 average rating, 78 reviews

Creekside Cottage | The Fitz House Red Hook NY

SpeedRating, 5 stars2 weeks ago
This house is perfect; it feels bigger than it is because it's so beautifully appointed and decorated. Lots of thought in the small details. Comfortable, cozy and relaxing.
Top guest favourite
Cottage in Saugerties
4.97 out of 5 average rating, 126 reviews

Cottage on the creek with wonderful waterfall view

CynthiaRating, 5 stars1 week ago
R’s place restored our faith in beautiful and affordable air bnbs! We said numerous times during our stay that we would definitely be back. The setting was so beautiful and the outdoor spaces were incredibly enjoyable, especially with our dog. R’s kitchen is the best and super well stocked so we enjoyed many meals in. This place did not disappoint and we cannot wait to go back!

Private cottage rentals

Top guest favourite
Cottage in Rhinebeck
5 out of 5 average rating, 47 reviews

Luxury Cottage w/ Amenities Galore 1 Mile to Town

AnnetteRating, 5 stars2 weeks ago
Gretchen's house was a lovely getaway for our annual girl's weekend. It is conveniently located near the downtown area of Rhinebeck, which made it super convenient to great restaurants, eclectic shops, and more. The house was cozy and well appointed. It was a rainy weekend, so we spent more time inside the house than planned, and we were glad that we opted for renting a house rather than a hotel. Gretchen was a great communicator with clear instructions. Thank you, Gretchen for being a wonderful host and entrusting your lovely home to us for the weekend!
Guest favourite
Cottage in Amenia
5 out of 5 average rating, 5 reviews

Quaint Country Cottage

RubyRating, 5 stars7 months ago
Wakeitha’s place was perfect for our family. It had everything we needed and the location was super convenient. We appreciate her hospitality and responsiveness.
Guest favourite
Cottage in Millbrook
4.97 out of 5 average rating, 63 reviews

Millbrook Cottage Originally a 1927 Sears Kit House

BryanRating, 5 stars8 months ago
Holly met us despite a late check-in. Friendly and responsive. Well equipped kitchen for cooking, which is important to us.
Guest favourite
Cottage in Pleasant Valley
4.84 out of 5 average rating, 25 reviews

The Lucky Goat Farm

KevinRating, 5 stars2 weeks ago
It was very relaxing and peaceful experience. The pool was an absolute plus(and the coffee was really good)!! Sara and her family are very kind.
Top guest favourite
Cottage in Saugerties
5 out of 5 average rating, 5 reviews

Cottage w/ Creek Views: Newly Renovated:HITS

LilyRating, 5 stars5 days ago
What a beautiful space!! Stayed here with my partner for a weekend getaway and had a wonderful time! Michael’s place is clean, warm, and cozy. We loved the kitchen and everything was just so beautiful and brand new! Will definitely come back and recommend to friends.
Cottage in Kingston
4.89 out of 5 average rating, 137 reviews

Modern, Lakeside Cottage

CaelyRating, 5 stars8 months ago
We had a very peaceful and pleasant visit at Daniel's home! The beds were very comfortable, plenty of extra sheets and blankets if needed, beautiful art on the walls, and in a beautiful setting. There were also plenty of appliances, so it was a very convenient and comfortable stay. We had a little trouble finding it, but Daniel is extremely responsive and friendly and gave great directions. I recommend this home for your next peaceful getaway!
Guest favourite
Cottage in Sherman
5 out of 5 average rating, 5 reviews

Candlewood Cottage

MattRating, 5 stars8 months ago
Dana's house was absolutely beautiful and immaculate. It was an older house that had been totally redone with high quality amenities, furniture and appliances. There was everything you needed and most of it felt brand new! Dana was extremely responsive and provided a really nice welcome booklet with a lot of information about that area that was very helpful. This house was well worth the cost and I would for sure stay again!
Guest favourite
Cottage in Pine Plains
4.91 out of 5 average rating, 22 reviews

Peacock Garden Cottage

AnnieRating, 5 stars3 weeks ago
Jeanne was a phenomenal host. Not only are there little notes around the house to best orient you, she also leaves a detailed guide to the surrounding area (hikes, restaurants, galleries, even a list of birds you might see!). The house itself is wonderful - cozy and rustic in all the right ways, but still extremely comfortable and top notch. If we ever end up in the area again, we’d absolutely return. Thank you!

Destinations to explore