
Pet-friendly holiday rentals in New Windsor
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Top-rated pet-friendly home rentals in New Windsor
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Popular amenities for New Windsor pet-friendly home rentals
Pet-friendly house rentals

Stunning Modern Barn minutes from Woodstock 21N195
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.

Private, Elegant Chalet w/ A Breathtaking View
Incredible home! We spent the weekend here with our dog. The large fenced yard was amazing for her. The house is tastefully furnished and very comfortable. The view is wonderful. The town is less than a 5-min drive, with wonderful cafes, restaurants, a grocery store and some cool shops. Great place all around and a good size for a larger family or small group of friends too. Thanks for a great weekend!

Balmville Mid-Century Gem & Work From Home Retreat
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

Modern Upstate Gem Surrounded by Trees | Hot Tub
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!

Welcome to Malden Manor, in a prime location!
Lovely place in Saugerties, close to lots of great hiking and restaurants.

Dazzling Design, Hot Tub, Huge Rooms, Privacy
The place was well stocked and clean upon arrival. We had a bit of trouble with the lock at first, but then everything got sorted, Leah was quick to respond and check in with us to make sure everything was going well! The area is quiet and about a 20-30 minute drive away from most things. There was a lot of open communal space for our group to hang out. Kitchen and bathrooms were perfect.

Welcome to The Boathouse! Waterfront/Boats/Hot tub
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 :)

1834 Farm House
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!
Pet-friendly home rentals with a pool

Stunning Sullivan County Cabin w/HotTub/Spa &Pool
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.

Seclusion and Romance - Hot Tub is hot hot hot
Nice little getaway during the cold season. The hot tub was excellent and about 100 degrees so perfect even with the cold temperature. It was still possible to put together a meal with the propane grill and warm things up in the microwave or store them away in the fridge. The heat was excellent in the space. Seems like it would be a great place to stay in the summer as well!

Renovated Forest Oasis with Pool & Fire-pit
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.

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

On The Rocks In The Hot Tub
I had an absolutely wonderful stay at Marcela's Airbnb! I was in town for the Spartan Race and needed a comfortable place to relax after the event, and Marcela's place was the perfect spot. The house is spacious and inviting, offering plenty of room to unwind. After pushing myself during the race, the hot tub was an absolute dream—perfectly maintained, spacious, and the ideal place to soak in and let the stress melt away. Marcela herself was incredibly polite, responsive, and thoughtful, making sure I had everything I needed for a relaxing stay. She really went out of her way to ensure I was comfortable. If you're looking for a peaceful and rejuvenating retreat, especially after a big event, I highly recommend Marcela's place!

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

Secluded Woodstock Retreat with Pool and Sauna
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.

4BR Cabin w/ Hot Tub, Fire pit, Hiking, Pool (5/8)
Really enjoyable stay in Caitlin’s place. Perfectly laid out with everything you need for a nice relaxing trip to the mountains. Highly recommend, already looking forward to returning!
Private, pet-friendly home rentals

Nicks Place
We thoroughly enjoyed our stay, the house was neat, clean and well stocked with everything we needed. The location was absolutely beautiful and check in and our procedures were very easy.

Pet Friendly Cabin Doh-Ray up at 1450 ft
Beautiful location...nice and quiet. 7 or 8 mins to woodstock. Decorated seemingly professionally. All the appointments (convennces) you could ask for.

Catskills Country Cottage
"This feels like home already." That was my 8-year-old's response to this sweet Kerhonkson cottage, just one hour after we arrived. I could end my five-star review there but I'll add some perks listed and not listed, which we really enjoyed. Prime location. The cottage is within a 20-minute radius of so many wonderful spots. We come for the Bonticue Crag rock scramble but stay for Saunderskill Farm, Upstate Taco, Bluebird Wine and Spirits and so much more. The creek. My kids walked there barefoot and sunned on the rocks. If you're lucky: farm fresh eggs are sold on the honor system on the main road just past the creek. The shower. You'll see. Smaller perks: The back deck gets great sun. So much closet/drawer space to organize your stuff. Lighting options galore, and almost all of them on dimmers. Sonos sound system and a charging station. The cozy office space, in case you have to "check in" or if you just want some alone time. Thank you, Consuelo! We'll be back.

2 bedroom / Office - HEPA Air Purifier
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.

Get Away to "Hygge" Tiny House on 75 Private Acres
Staying at this Tiny House was a wonderful experience. The hosts are incredibly responsive and kind, and the tiny house itself has excellent privacy. The location is a few minutes drive from multiple charming towns. The hosts' dog Ziggy and Fjord horse Spunky are lovely, and the tiny house is pet friendly! I brought my dog, and she had a delightful grooming experience on premises. We will return!

5 Acre Nature Escape · Rockpine Cabin
Maria and Max’s place was everything we dreamed of! It was a nice seclude, a cabin with a large backyard and a wonderful fire pit. We loved the decor inside the house, the beds were extremely comfortable, and everything was as described. It’s in a great location approximately 20 to 30 minute drive to multiple cute small towns in Catskills. We can’t wait to bring our friends back next time!

Enthusiastic Spirits. Close to Parks W/Cliff Views
Great place with lovely views!!! Beds were very comfy. I felt very refreshed after sleeping which I rarely feel at hotels/ airbnbs. Carl was very friendly and passionate about hospitality.

Hot Tub Bliss 5mi to Kingston on 3 acres
Kim was a wonderful host!! She was active in terms of replying and very much helpful when needed. The Airbnb was amazing and matched the pictures perfectly. I had a very relaxing stay, away from the city. Very much recommended to anyone who would like a private and quiet place to unwind. I would love to visit soon🥰
Quick stats about holiday rentals that are pet-friendly in New Windsor
Total rentals
10 properties
Nightly prices starting at
£60 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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- Radio City Music Hall
- Times Square
- Hunter Mountain
- Columbia University
- Fairfield Beach
- Riverside Park
- Rye Beach
- Mountain Creek Resort
- Apollo Theater
- St. Nicholas Park
- Yankee Stadium
- Rye Playland Beach
- MetLife Stadium
- Inwood Hill Park
- Bronx Zoo
- Bethel Woods Center for the Arts
- Rockefeller Center
- The Metropolitan Museum of Art
- Central Park Zoo
- Minnewaska State Park Preserve
- The Kartrite Resort & Indoor Waterpark
- Rye Town Beach
- Seaside Beach
- Resorts World Catskills