Pet-friendly vacation rentals in New Windsor

Find and book unique pet-friendly homes on Airbnb

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Popular amenities for New Windsor pet-friendly home rentals

Pet-friendly house rentals

Guest favorite
Home in Mount Tremper
4.9 out of 5 average rating, 224 reviews

Stunning Modern Barn minutes from Woodstock 21N195

Tracy,JRating, 5 stars3 weeks ago
A beautiful and thoughtfully reconstructed house. It has everything you could need to enjoy a very chill time at the house indoors and outdoors or even cook a meal in. Kid friendly.Beautiful light. Beautiful views. Very convenient location. Kind hosts. We have stayed at a few places around town but this was by far our favorite house.
Guest favorite
Home in Newburgh
4.99 out of 5 average rating, 150 reviews

Balmville Mid-Century Gem & Work From Home Retreat

MicahRating, 5 stars1 week ago
This is a jewel of a retro-designed home —spacious, tastefully decorated, stocked kitchen, comfortable bedrooms and views of the Hudson with great access to newburgh and beacon downtowns. Great communication and flexibility on check in and out. Would definitely stay again! Thanks
Superhost
Home in Wallkill
4.86 out of 5 average rating, 121 reviews

Modern Upstate Gem Surrounded by Trees | Hot Tub

RobertoRating, 5 stars1 month ago
I had a wonderful stay at this beautiful modern home in Wallkill, NY. Tucked away on a quiet street with plenty of privacy from the surrounding trees, it felt like the perfect escape from the city. My favorite part was the open-concept kitchen and living area, with expansive windows that made it feel like I was immersed in nature while still enjoying the comfort of being indoors. It was the ideal space to rest, relax, and recharge. If you're looking for a peaceful getaway, I highly recommend this home!
Top guest favorite
Home in Saugerties
4.97 out of 5 average rating, 126 reviews

Welcome to Malden Manor, in a prime location!

OrionRating, 5 stars3 months ago
Lovely place in Saugerties, close to lots of great hiking and restaurants.
Guest favorite
Home in New Paltz
4.96 out of 5 average rating, 201 reviews

Eclectic one-bedroom house

KarinaRating, 5 stars1 week ago
It’s a really quirky place, perfectly situated for town and for trails. The kitchen is really well equipped, it feels like staying in someone else’s house, but they aren’t there! We really loved having the lights left on for us when we arrived. That made for a warm welcome.
Guest favorite
Home in New Paltz
4.94 out of 5 average rating, 271 reviews

Welcome to The Boathouse! Waterfront/Boats/Hot tub

SydneyRating, 5 starstoday
We stayed here right after our wedding in Westchester county as a "mini-moon" for a couple of days and absolutely loved it! It was the perfect place to relax especially on the patio overlooking the water and the hot tub was an added bonus. This is one of the few Airbnbs we have stayed in that we would go back to in a heartbeat. Beautiful!!! Highly recommend :)
Guest favorite
Home in Cold Spring
4.91 out of 5 average rating, 256 reviews

1834 Farm House

FrankieRating, 5 stars1 month ago
We enjoyed a beautiful early spring stay on the farm with a group of 7 ladies, gathering for a chill bachelorette weekend in Cold Springs. The farmhouse was super cozy; great for cooking, crafting, games, tea time, outdoor wine picnics, star gazing at night in the hot tub and making friends with the chickens! A great retreat spot for groups with all the amenities!
Guest favorite
Home in Marlboro Township
4.99 out of 5 average rating, 192 reviews

Historic 1873 Farmhouse Near Vineyards & Orchards

JeffRating, 5 stars1 week ago
We spent the weekend at this amazing farmhouse and didn’t want to leave—seriously, we were this close to moving in. Mark and Whitney were absolute gems of hosts, making us feel instantly at home with everything we could possibly need. The vibe? Retro charm meets cozy comfort. The kitchen counter was so long and inviting, it became my hangout spot whether we were cooking or just chatting. My daughter claimed the little lounge outside the second bedroom as her study nook, our family friend took over the artsy fashion studio room, and my wife fell in love with the living room—aka the evening chill zone. We shared family-style dinners in the dreamy dining area, melted into the comfiest beds ever, and just when we thought it couldn’t get better… enter the old-school record player. Dropping the needle on vinyl while we lounged around? Pure, unexpected magic. The whole place had this nostalgic, feel-good energy that made the weekend unforgettable.

Pet-friendly home rentals with a pool

Guest favorite
Cottage in Clinton Corners
4.89 out of 5 average rating, 168 reviews

Tranquil Cottage in the Country

MaximilianRating, 5 stars6 months ago
Pictures don’t do justice! Craig’s place was lovely, from the amazing kitchen to the spacious living room and the outdoor patio. For a group getaway this is the perfect place. Would stay here again in a heartbeat!
Superhost
Cabin in Swan Lake
4.83 out of 5 average rating, 201 reviews

Stunning Sullivan County Cabin w/HotTub/Spa &Pool

CarolineRating, 5 stars1 month ago
Our group had a great time at Anna’s place. Spacious and comfortable with great views. Anna is very responsive and gave clear check in instructions. Little communication needed given her detailed instructions, and the little communication needed- she was very responsive.
Superhost
Chalet in Ruby
4.9 out of 5 average rating, 115 reviews

Enchanting Upstate Cabin w Pool, Firepit

ErinRating, 5 stars2 months ago
Beautiful home, even better in person! Clean and cozy. Each room was stylishly and uniquely decorated. Great for large groups.
Guest favorite
Apartment in Suffern
4.94 out of 5 average rating, 128 reviews

Renovated Forest Oasis with Pool & Fire-pit

CarolRating, 5 stars5 months ago
Lovely quiet, pet-friendly place above the garage but note that there is a steep staircase to get up to the second floor. Very friendly hosts - greeted me on arrival and had left the door unlocked so entry was easy and the key was available for my use. Comfy bed, cozy and warm rooms with remote-controlled mini-splits in both the living room and bedroom. Bathroom with tub and separate shower - the water pressure was not as strong in the shower as I would have liked, but it was nice to have the skylight in there. My GPS found it easily but a larger sign with the house number would be helpful, especially at night. I would definitely stay there again.
Guest favorite
Home in Woodstock
4.86 out of 5 average rating, 132 reviews

Gorgeous Villa Mntn Views, salt H2O pool, hot tub!

HelaRating, 5 stars1 month ago
Beautiful home with amazing views. The house was very clean and spacious, the views were amazing. Susanna was very responsive and gave clear instructions. We had a very relaxing weekend and enjoyed very much staying at the house. We would love to come back.
Guest favorite
Home in West Milford
4.98 out of 5 average rating, 149 reviews

On The Rocks In The Hot Tub

DarrenRating, 5 stars4 weeks ago
Great place. loved the pool table, darts and shall shuffleboard. lots of good wineries and cider places within 25 mins. pennings is our fav. didn't use the hot tub so couldn't comment but looked nice and private. driveway is steep but easily driveable. recommended. also didn't have coffee filters and they paid for some to be delivered same day! sweet.
Guest favorite
Guest suite in Holmes
4.98 out of 5 average rating, 192 reviews

Pool opens 5/23! Huge, Eclectic… 1.5 hr to NYC!

RachelRating, 5 stars2 months ago
The place was much bigger than the photos and we enjoyed the stay! especially the indoor fireplace and the house is beautifully decorated. Blake was a great host, she did a quick tour of the place when we arrived and gave us some flexible check out time because of the weather/road condition (thank you!) even though we left just before the check out time. Overall, it was a wonderful stay :)
Guest favorite
Chalet in Mount Tremper
4.98 out of 5 average rating, 145 reviews

Secluded Woodstock Retreat with Pool and Sauna

BarryRating, 5 stars2 months ago
My wife and I stayed at Ron’s place for five nights for a winter getaway. We had a great stay, highlights include a comfortable king bed, a quiet setting, a cozy fireplace, and the large ground floor bathroom that feels like your own spa- we thoroughly enjoyed the sauna, huge bathtub, and rain shower. Ron was a great host and was very responsive with any questions we had. We spent many hours watching TV on the screen and projector set up, we grabbed more pillows from upstairs to add some more cushion to the leather couch downstairs.

Private, pet-friendly home rentals

Top guest favorite
Cottage in Livingston Manor
4.99 out of 5 average rating, 153 reviews

Nicks Place

Chun YeeRating, 5 stars3 months ago
We had a wonderful time at Nick’s Place. Great wood cabin with very warm heating during our stay where we had a snowstorm. Very cozy and wonderful view of the mountains.
Superhost
Chalet in Monticello
4.85 out of 5 average rating, 107 reviews

Modern Chalet with Hot Tub and Lake Access

MichaelRating, 5 stars1 month ago
Awesome place! Very peaceful, secluded, and plenty of room for our group of 6. We enjoyed the front deck that offers a great spot to enjoy the fresh air and get some nice views of the surrounding area. The kitchen was spacious and had everything we needed and more. Not necessarily a complaint, but understand there is either a $500 refundable deposit or a $70 non-refundable charge for the booking. This is not common in my experience on AirBnb, but is required for the booking, so just wanted to put that out there. Overall, this is still 5 out of 5 stars for many reasons and I would highly recommend staying here.
Superhost
Cabin in Greenwood Lake
4.86 out of 5 average rating, 219 reviews

Get some R&R at the Rustic Retreat!

SamanthaRating, 5 stars1 week ago
Such a beautiful and clean space! My doggies also loved it!! Would definitely stay here again!
Top guest favorite
Home in Woodstock
4.99 out of 5 average rating, 141 reviews

Whispering Pines: Secluded Retreat near town

VanessaRating, 5 stars3 months ago
Jason's home was lovely and accurately described & appointed - my friends and I spent a wonderful weekend with our pups and were even blessed by some snow! The fireplaces (yes - two!) were a great add-on and we were super excited to relax and enjoy all the home has to offer. Thanks so much again Jason! :)
Guest favorite
Cabin in Woodstock
4.97 out of 5 average rating, 148 reviews

Pet Friendly Cabin Doh-Ray up at 1450 ft

JosephRating, 5 stars2 months ago
Beautiful location...nice and quiet. 7 or 8 mins to woodstock. Decorated seemingly professionally. All the appointments (convennces) you could ask for.
Superhost
Apartment in Kingston
4.82 out of 5 average rating, 108 reviews

2 bedroom / Office - HEPA Air Purifier

SarahRating, 5 stars5 months ago
Orna was so welcoming and easy to communicate with. The apartment is cozy and well appointed. We were visiting our daughter and family for Thanksgiving. They recently moved to Kingston . Great location! This would not affect most people, but my 90 year “young” dad was with us, so the old fashioned tub/shower was a bit of a hazard for him. Really a gem of a place if you are traveling through or visiting loved ones in Kingston.
Top guest favorite
Cabin in Chichester
4.99 out of 5 average rating, 245 reviews

Catskill Mtn Streamside Getaway

ZacharyRating, 5 stars2 weeks ago
Jeff and Sharon were very responsive and provided us with everything we need to have a great time!
Top guest favorite
Tiny home in Wallkill
4.99 out of 5 average rating, 287 reviews

Get Away to "Hygge" Tiny House on 75 Private Acres

RipsimeRating, 5 stars1 week ago
Wonderful house in a very nice place! The accommodation is very clean and fully corresponds to the description! The owner is friendly and very attentive to his guests! Will definitely come back!

Quick stats about vacation rentals that are pet-friendly in New Windsor

  • Total rentals

    10 properties

  • Nightly prices starting at

    $80 before taxes and fees

  • Total number of reviews

    730 reviews

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wifi availability

    10 properties include access to wifi

  • Popular amenities

    Kitchen, Wifi, and Pool

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